Multiple Biological Activities of Unconventional Seed Oils 0128241357, 9780128241356

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MULTIPLE BIOLOGICAL ACTIVITIES OF UNCONVENTIONAL SEED OILS

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MULTIPLE BIOLOGICAL ACTIVITIES OF UNCONVENTIONAL SEED OILS Edited by

ABDALBASIT ADAM MARIOD Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan; College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia

Academic Press is an imprint of Elsevier 125 London Wall, London EC2Y 5AS, United Kingdom 525 B Street, Suite 1650, San Diego, CA 92101, United States 50 Hampshire Street, 5th Floor, Cambridge, MA 02139, United States The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, United Kingdom Copyright © 2022 Elsevier Inc. All rights reserved. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any information storage and retrieval system, without permission in writing from the publisher. Details on how to seek permission, further information about the Publisher’s permissions policies and our arrangements with organizations such as the Copyright Clearance Center and the Copyright Licensing Agency, can be found at our website: www.elsevier.com/permissions. This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). Notices Knowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary. Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility. To the fullest extent of the law, neither the Publisher nor the authors, contributors, or editors, assume any liability for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions, or ideas contained in the material herein. British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library Library of Congress Cataloging-in-Publication Data A catalog record for this book is available from the Library of Congress ISBN: 978-0-12-824135-6 For Information on all Academic Press publications visit our website at https://www.elsevier.com/books-and-journals

Publisher: Nikki Levy Acquisitions Editor: Nina Bandeira Editorial Project Manager: Emerald Li Production Project Manager: Sujatha Thirugnana Sambandam Cover Designer: Miles Hitchen Typeset by MPS Limited, Chennai, India

Contents List of contributors xiii

3. Biological activities and therapeutic effects of Celastrus paniculatus seed oil 29

1. Unconventional oils production, utilization worldwide 1

Kim Wei Chan, Voon Kin Chin, Norsharina Ismail, Der Jiun Ooi, Nicholas M.H. Khong and Norhaizan Mohd Esa

Haroon Elrasheid Tahir, Abdalbasit Adam Mariod and Zou Xiaobo

Abbreviations 29 3.1 Botanical description, geographical distribution and traditional medicinal uses of Celastrus paniculatus 30 3.2 Chemical composition of Celastrus paniculatus seed oil 31 3.3 Biological activities and therapeutic effects of Celastrus paniculatus seed oil 33 3.3.1 Neuroprotective properties 34 3.3.2 Antifertility properties 36 3.3.3 Antioxidant, anti-inflammatory and anti-arthritic properties 36 3.3.4 Cosmeceutical and wound healing properties 38 3.3.5 Gastroprotective properties 38 3.4 Toxicological assessment of Celastrus paniculatus seed oil 39 References 40

1.1 1.2 1.3 1.4

Introduction 1 Oil production methods 3 Unconventional oil worldwide 4 Utilization of unconventional oil 6 1.4.1 Potential medicinal uses 6 1.4.2 Potential food uses 7 1.4.3 Potential cosmetic uses 8 1.4.4 Potential biodiesel fuels uses 9 1.5 Conclusion 10 References 10

2. Biological activities, definition, types and measurements 17 Abdalbasit Adam Mariod and Haroon Elrasheid Tahir

2.1 Introduction 17 2.2 Types of biological activities 18 2.2.1 Antimicrobial activity 18 2.2.2 Antibacterial and antifungal activity 19 2.2.3 Antioxidant activity 19 2.2.4 Antitubercular activity 20 2.2.5 Antiinflammatory activity 21 2.2.6 Anticancer activity 22 2.2.7 Antiaging 23 2.2.8 Antimalarial activity 24 2.2.9 Antiproliferative activity 24 2.2.10 Hypoglycaemic activity 25 2.2.11 Hypocholesterolemic activity 25 2.2.12 Antihypertensive activity 25 2.2.13 Antitumor activity 26 2.3 Conclusion 26 References 27

4. Biological activities of black cumin (Nigella sativa) seed oil 43 Merve Seyda ¸ Karac¸il Ermumcu

Abbreviations 43 4.1 Introduction 44 4.2 Nigella sativa seed and its chemical composition 44 4.3 Biological activities of Nigella sativa seed and its oil 45 4.3.1 Antioxidant properties 45 4.3.2 Antihyperlipidemic and antihypercholesteremic properties 4.3.3 Antihypertensive properties 47 4.3.4 Antidiabetic properties 47 4.3.5 Antiobesity properties 49 4.3.6 Antiinflammatory properties 49

v

45

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4.3.7 Anticancer properties 50 4.3.8 Potential toxicity of Nigella sativa Oil 50 4.4 Conclusions and suggestions 50 References 50

5. Biological activities of Moringa seeds oil 55 Yosvany Dı´az-Domı´nguez, Ramo´n Piloto-Rodrı´guez, Elina Ferna´ndez-Santan, Maylin Rondo´n-Macias and Danger Tabio-Garcı´a

Abbreviations 55 5.1 Introduction 55 5.2 Phytochemistry 56 5.3 Botanical descriptions and geographical distribution 56 5.4 Cultivation for leaves and seed production 58 5.5 Seeds of Moringa species 59 5.6 Moringa seeds oil 60 5.6.1 Fatty acid composition 60 5.6.2 Oxidative stability 62 5.6.3 Sterol and tocopherol composition 63 5.6.4 Biological activities of Moringa seeds oil 64 5.7 Conclusion 71 References 71

6. Biological activities and antioxidant properties of Guizotia abyssinica (niger) seed oil 77 W.K. Solomon and T.P. Nkambule

Abbreviations 77 6.1 Introduction 77 6.2 Chemical composition and properties of Guizotia abyssinica seed 78 6.3 Fatty acid profile of Guizotia abyssinica oil 78 6.4 Phytochemicals in Guizotia. abyssinica 80 6.5 Bioactivities of Guizotia abyssinica seed 80 6.5.1 Tocopherols 81 6.5.2 Total phenolics 81 6.5.3 Total sterols 82 6.5.4 Total carotenoids 82 6.5.5 Vitamin K1 83 6.6 Effect of extraction solvent on bioactive composition and antioxidant activity 83 6.7 Biological activities of Guizotia abyssinica 84

6.7.1 Antimicrobial activity of Guizotia abyssinica seed 84 6.7.2 Antifungal activities of Guizotia abyssinica seed 85 6.7.3 Anticancer activity of Guizotia abyssinica seed 85 6.7.4 Antiinflammatory activity of Guizotia abyssinica seed 86 6.7.5 Antioxidant activity of Guizotia abyssinica 86 6.8 Other biological activities 88 6.9 Conclusion 88 References 88

7. Antimicrobial activity of Roselle (Hibiscus sabdariffa L.) seed oil 91 Abdel Moneim Elhadi Sulieman

7.1 Introduction 91 7.2 Roselle distribution, ecology, and cultivation 93 7.3 Nutritional and phytochemical composition of Roselle 94 7.4 Uses of Roselle 95 7.5 Roselle seed oil 96 7.5.1 Physicochemical characteristics of Roselle seed oil 96 7.6 Microbiology of Roselle 96 7.7 Antimicrobial activity of Roselle 97 7.8 Conclusion 98 References 98

8. Antioxidant and antimicrobial activities of Monechma ciliatum seed oil 101 Abdalbasit Adam Mariod and Haroon Elrasheid Tahir

8.1 Introduction 101 8.2 Monchema ciliatum (black mahlab) 102 8.3 Nutritional value and chemical composition of Monchema ciliatum 102 8.4 Antioxidant activity of Monechma ciliatum 103 8.5 Antimicrobial activity of Monechma ciliatum 104 8.6 Uterotonic property of Monechma ciliatum 105 8.7 Antimalarial activity of Monechma ciliatum 106

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8.8 Anticancer activity 107 8.9 Cosmetical uses of Monechma ciliatum seeds and oil 107 8.10 Conclusion 107 References 107

9. Antioxidant and antimicrobial activity of fenugreek (Trigonella foenum-graecum) seed and seedoil 111 Sara Thamer Hadi and Abdalbasit Adam Mariod

9.1 9.2 9.3 9.4 9.5 9.6 9.7 9.8

Introduction 111 Botanical description 113 Chemical composition 113 Different uses of fenugreek 113 Fenugreek seed composition 114 Fenugreek seed oil composition 115 Fenugreek antioxidant activity 115 Antibacterial and antifungal effect of fenugreek oil 116 9.9 Conclusion 116 References 116

12. Antioxidant, antimicrobial, and antidiabetic activities of Citrullus colocynthis seed oil 139 Abdalbasit Adam Mariod and Robert L. Jarret

10. Antiinflammatory, antimicrobial, and allelopathic activities of some cucurbit seed oils 119 Ogueri Nwaiwu and Abdalbasit Adam Mariod

12.1 Introduction 139 12.2 Colocynth seed chemistry 139 12.3 Biological activity of colocynth extracts 141 12.3.1 Antioxidant activity of colocynth seed oil 141 12.3.2 Antimicrobial activity of colocynth seed oil 142 12.3.3 Antidiabetic activity of colocynth seed oil 143 12.4 Conclusion 144 References 144

13. Antioxidant and pharmacological activity of Cucumis melo var. cantaloupe 147

10.1 Introduction 119 10.2 Antiinflammatory activities of some cucurbits oil 120 10.3 Overview of antimicrobial activity of cucurbits seed oil 121 10.4 Allelopathic activities of some cucurbits oil 122 10.5 Conclusion 123 References 123

Neuza Jorge, Ana Carolina da Silva and Carolina M. Veronezi

11. Cucumis melo L. seed oil components and biological activities 125 Mafalda Alexandra Silva, Taˆnia Gonc¸alves Albuquerque, Rita Carneiro Alves, M. Beatriz P.P. Oliveira and Helena S. Costa

11.1 Introduction 125 11.2 Botanical, morphology, and cultivation 11.3 Melon seed oil composition 127 11.3.1 Fatty acids 127 11.3.2 Vitamin E 128

11.3.3 Phytosterols 128 11.3.4 Phenolic compounds 129 11.4 Biological activities 130 11.4.1 Antioxidant activity 130 11.4.2 Antiinflammatory activity 131 11.4.3 Antimicrobial activity 132 11.4.4 Antihypercholesterolemic activity 132 11.5 Conclusion 132 Acknowledgments 133 References 133

126

Abbreviations 147 13.1 Introduction 148 13.2 Botanical description, distribution, and cultivation regions of melon 148 13.2.1 Pulp 150 13.2.2 Peels 152 13.2.3 Seeds 154 13.3 Antioxidant and pharmacological properties 160 13.3.1 Leaves 161 13.3.2 Pulp 161 13.3.3 Peels 162 13.3.4 Seeds 163 13.4 Conclusions 164 References 164

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14. Pumpkin seed oil components and biological activities 171 Mohamed A. Gedi

14.1 Introduction 171 14.2 Pumpkin botany 172 14.3 Composition of pumpkin seed oil 175 14.3.1 Fatty acid profile of pumpkin seed oil 175 14.3.2 Bioactive compounds of pumpkin seed oil 176 14.4 Antimicrobial, antiinflammatory and antidiabetic properties of pumpkin seed oil 178 14.4.1 Antimicrobial property of pumpkin seed oil 178 14.4.2 Antiinflammatory property of pumpkin seed oil 179 14.4.3 Antidiabetic property of pumpkin seed oil 180 14.5 Conclusion 180 References 180

15. Antioxidant and pharmacological activity of watermelon (Citrullus lanatus) seed oil 185 Abdel Moneim Elhadi Sulieman and Salwa Elamin Ibrahim

15.1 Introduction 185 15.2 Significance of medicinal plants 186 15.3 Proximate chemical composition of watermelon 187 15.4 Minerals content 187 15.5 Fatty acids content 187 15.6 General phytochemical screening of the watermelon plant seeds 189 15.7 Antimicrobial activity of the watermelon plant 191 15.8 Conclusion 193 References 193

16. Rice bran oil main bioactive compounds and biological activities 195 Norazalina Saad, Norsharina Ismail, Siti Nurulhuda Mastuki, Sze Wei Leong, Suet Lin Chia and Che Azurahanim Che Abdullah

Abbreviations 195 16.1 Introduction 196

16.2 16.3 16.4 16.5

Rice milling and by-products 196 Rice bran 197 Rice bran oil 198 Bioactive phytochemicals in rice bran oil 200 16.6 Role of bioactive components and activities 201 16.6.1 Antioxidant potential of rice bran oil 201 16.6.2 Hypercholesterolemia 202 16.6.3 Anticancer aspects 204 16.6.4 Antidiabetic properties of rice bran oil 207 16.7 Conclusion and future perspectives 208 References 209

17. Different biological activities (antimicrobial, antitumoral, and antioxidant activities) of grape seed oil 215 Isabella Rosa da Mata, Simone Morelo Dal Bosco and Juliano Garavaglia

List of Abbreviations 215 17.1 Introduction 216 17.2 Antioxidant and antiinflammatory activity 219 17.3 Antitumoral activity 220 17.4 Antimicrobial activity 222 17.5 Other potential biological activities of grape seed oil 224 17.6 Conclusions 224 References 225

18. Citrus seeds fixed oil, composition and its biological activities 229 Rasheeda Hamid Abdalla Ahmed and Abdalbasit Adam Mariod

18.1 18.2 18.3 18.4

Introduction 229 What are fixed oils? 230 Composition of citrus seeds fixed oil 230 Biological activities of citrus fixed seed oil 231 18.4.1 Antioxidant activity 231 18.4.2 Different biological activities 233 18.5 Conclusion 234 References 234

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19. Biological activities of tea seed (Camellia oleifera Abel.) oil 237 Fong Fong Liew, Kim Wei Chan and Der Jiun Ooi

19.1 Introduction 237 19.2 Chemical composition of tea seed oil 238 19.3 Biological activities 240 19.3.1 Improve lipid profiles 240 19.3.2 Ameliorate hypercholesterolemiainduced ocular disorder 242 19.3.3 Improve physical performance and prevent fat accumulation 242 19.3.4 Mediate hepatoprotective activity 243 19.3.5 Modulate gastrointestinal protective effect 244 19.3.6 Exert antihypertension effect 245 19.3.7 Serve as potential neuroprotective agent 245 19.3.8 Mediate antimicrobial activity 246 19.3.9 Exert bone-protective role 246 19.3.10 Exhibit antioxidant and antiinflammatory properties 247 19.3.11 Suppress melanogenesis 247 19.3.12 Potential lactogenic effect 248 19.4 Concluding remarks and future trends 248 References 248

20. Biological activities of rubber (Hevea brasiliensis) oil 253 Abdalbasit Adam Mariod and Haroon Elrasheid Tahir

20.1 Introduction 253 20.2 Biological activities of rubber seed oil 254 20.3 Conclusion 255 References 256

21. Biological activities of pequi (Caryocar brasiliense Camb.) pulp oil 257 Daniele Paula (de Almeida), Arthur da Capela (Pompilio), Alisson Felipe Martins (Lima), Nataly Costa (de Almeida) and Carini Lelis (Aparecida)

21.1 21.2 21.3 21.4

Introduction 257 Pequi 258 Nutritional composition 259 Bioactive compounds of pequi 260

21.5 Pequi pulp oil 261 21.6 Biological activities of pequi pulp oil (Caryocar brasiliense Camb.) 263 21.7 Final considerations 264 21.8 Conclusion 265 References 265

22. Biological activities of Allanblackia (Allanblackia parviflora) oil 269 Siti Nurulhuda Mastuki, Siti Munirah Mohd. Faudzi, Norsharina Ismail and Norazalina Saad

Abbreviations 269 22.1 Introduction 269 22.2 Ethnobotany 270 22.2.1 Vernacular names 270 22.2.2 Botanical description 271 22.3 Nutritional and chemical compositions of Allanblackia parviflora 272 22.3.1 Nutritional and chemical compositions of Allanblackia parviflora oil 272 22.3.2 Nutritional, mineral, and chemical compositions of Allanblackia parviflora seeds 273 22.3.3 Chemical compositions of Allanblackia parviflora leaves 274 22.3.4 Chemical compositions of Allanblackia parviflora stem 274 22.4 Biological activity of Allanblackia parviflora 275 References 277

23. Biological activities of pistachio (Pistacia vera) oil 279 Norsharina Ismail, Kim Wei Chan, Siti Nurulhuda Mastuki, Norazalina Saad and Ahmad Faizal Abdull Razis

Abbreviations 279 23.1 Introduction 279 23.1.1 Pistacia vera plant description and distribution 280 23.2 Pistacia vera chemical composition 281 23.3 Uses of Pistacia vera 284 23.4 Biological activities of Pistacia vera oil 285 23.4.1 Antioxidant capacity and oxidative stability 285 23.4.2 Scolicidal activity 287 23.4.3 Antileishmanial activities 287

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23.4.4 Antiinflammatory properties 23.4.5 Anxiety and depressive-like behaviors 287 23.5 Biological activities of Pistacia vera by-products 288 23.6 Safety concern 289 23.7 Conclusion 289 References 289

287

25.2.11 Treatment against kidney disorders 326 25.2.12 Atopic eczema/dermatitis 326 25.2.13 Antineuropathic activity 327 25.2.14 Hypocholesterolemic activity 327 25.2.15 Antiretroviral activity 327 25.3 Conclusion 328 References 328

24. Biological activities of argan (Argania spinosa L.) oil: Evidences from in vivo studies 295

26. Biological activities of Sclerocarya birrea kernel oil 333

Nicholas M.H. Khong and Kim Wei Chan

26.1 Introduction 333 26.2 Marula oil uses and biological activities 334 26.2.1 Antioxidant and antibacterial activity of marula oil 335 26.2.2 Antiaging activity of marula oil 335 26.2.3 The role of marula oil in protecting against environmental damage 336 26.3 Conclusion 336 References 336

24.1 Abbreviations 295 24.2 Introduction 295 24.3 Biological effects on human health 296 24.3.1 Clinical evidences 296 24.3.2 Preclinical studies and imminent developments of argan oil 301 24.4 Biological effects on animal health 310 24.5 Bioactive compounds contributing to the biological activity of argan oil 311 24.6 Safety and allergenicity of argan oil 313 24.7 Conclusion 313 References 313

25. Biological activities of evening primrose oil 317 Haroon Elrasheid Tahir, Gustav Komla Mahunu, Abdalbasit Adam Mariod, Zou Xiaobo and Newlove A. Afoakwah

25.1 Introduction 317 25.2 Biological activities 318 25.2.1 Treatment of rheumatoid arthritis 318 25.2.2 Treatment of Mastalgia 319 25.2.3 Antiinflammatory activity 320 25.2.4 Antioxidant activity 323 25.2.5 Anticancer and antitumor activity 324 25.2.6 Preventing and treatment of pain 325 25.2.7 Antiulcerogenic effects 325 25.2.8 Thrombolytic activity 325 25.2.9 Antibacterial activity 325 25.2.10 Antidiabetic activity 325

Abdalbasit Adam Mariod and Haroon Elrasheid Tahir

27. Biological activities of Balanites aegyptiaca (Heglig) kernel oil 339 Abdalbasit Adam Mariod and Essa Mohammed AhmedIsmail

27.1 27.2 27.3 27.4

Introduction 339 Economic outlook of Balanites aegyptiaca 340 Balanites aegyptiaca different uses 341 Balanites aegyptiaca Heglig as a medicinal tree 341 27.5 Chemical composition of Balanites aegyptiaca Heglig 342 27.6 Balanites aegyptiaca seed composition 342 27.7 Balanites aegyptiaca kernel oil 342 27.8 Biological activities of Balanites aegyptiaca oil 343 27.9 Conclusion 344 References 344

28. Factors affecting the quality of produced unconventional seed oils 345 ´ Ying Qian and Magdalena Rudzinska

List of abbreviations 345 28.1 Introduction 345 28.2 Agricultural factors 347

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28.3 28.4 28.5 28.6 28.7

Processing and handling of seed oils 348 Seed oil storage conditions 349 Quality characteristics 350 Fatty acid composition 352 Bioactive compounds 354 28.7.1 Tocochromanols 354 28.7.2 Phytosterols 355 28.7.3 Other bioactive compounds 355 28.8 Frying 356 28.9 Conclusions 357 References 358

29. Chemical and compositional structures (fatty acids, sterols, and tocopherols) of unconventional seed oils and their biological activities 363 Saeid Hazrati, Saeed Mollaei and Farhad Habibzadeh

29.1 Introduction 363 29.2 Pyrus glabra and Pyrus syriaca 364 29.2.1 Tocopherol composition 365 29.2.2 Biological activity of seed oils 29.2.3 Sterols 366 29.3 Chrozophora tinctoria 366 29.3.1 Fatty acid compositions 366 29.3.2 Tocopherol and sterols composition 367 29.3.3 Biological activity of seed oils 29.4 Pistacia spp 368 29.4.1 Fatty acid composition 369 29.4.2 Biological activity of seed oils 29.4.3 Sterol composition 370 29.4.4 Tocopherols 371 29.5 Nigella sativa 371 29.5.1 Sterol composition 372 29.5.2 Tocopherols 373 29.5.3 Biological activity of seed oil 29.6 Cucurbita pepo 374 29.6.1 Fatty acid composition 374 29.6.2 Tocopherols 375 29.6.3 Sterols composition 375 29.6.4 Biological activity of seed oils 29.7 Lallemantia spp 376 29.7.1 Fatty acid composition 376 29.7.2 Tocopherols 377 29.7.3 Sterol composition 377 References 377

365

367

30. Chemistry and composition of coconut oil and its biological activities 383 Rindengan Barlina, Kun Tanti Dewandari, Ira Mulyawanti and Tjahjono Herawan

List of abbreviations 383 30.1 Introduction 384 30.2 Varieties of coconut 384 30.3 Processing of coconut oil 385 30.3.1 Wet process 385 30.3.2 Dry process 386 30.4 Physico-chemical properties of coconut oil 387 30.5 Composition of coconut oil 388 30.5.1 Fatty acids composition 388 30.5.2 Micronutrient component of coconut oil 388 30.6 Virgin coconut oil composition 390 30.6.1 Lauric acid 391 30.7 Biological activities of coconut oil 392 30.7.1 Weight development of white rats 392 30.7.2 Cholesterol profile of white rat 393 30.8 Summary 393 References 394

31. Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil 397 Serkan Selli, Gamze Guclu, Onur Sevindik and Hasim Kelebek

369

373

376

31.1 Introduction 397 31.2 Fatty acid composition of hazelnut oils 398 31.3 Volatile composition and key odorants of hazelnut oil 400 31.4 Phenolic composition of hazelnut oils 403 31.5 Antioxidant properties of hazelnut oil 405 31.6 Antimicrobial activity of hazelnut oil 408 31.7 Conclusion 408 References 409

32. Production process, methods of extraction, and refining technologies of unconventional seed oils 413 Ramo´n Piloto-Rodrı´guez and Yosvany Dı´az-Domı´nguez

32.1 Introduction 413 32.2 Production process

414

xii 32.3 Methods of extraction 414 32.3.1 Solvent extraction of oil 415 32.3.2 Mechanical extraction of oil 416 32.3.3 Microwave-assisted extraction 418 32.3.4 Ultrasonic-assisted extraction 418 32.3.5 Supercritical fluid extraction 419 32.3.6 After extraction oil conditioning 419 32.4 Refining process and related technologies 420 32.4.1 Degumming 421 32.4.2 Neutralization 423

Contents

32.4.3 Bleaching 423 32.4.4 Deodorization 424 32.4.5 Oil modification technologies 424 32.5 Issues related to unconventional seed oil production for biological applications 425 32.6 Rural vegetable oil production 426 32.7 Transesterification for biodiesel production 427 32.8 Conclusions 428 References 428

Index 431

List of contributors Ahmad Faizal Abdull Razis Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

Simone Morelo Dal Bosco Nutrition Department, Federal University of Health Sciences of Porto Alegre (UFCSPA), Porto Alegre, Brazil

Che Azurahanim Che Abdullah UPM MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia; Department of Physics, Faculty of Science, Universiti Putra Malaysia, Serdang, Malaysia; Materials Synthesis and Characterization Laboratory, Institute of Advanced Technology (ITMA), Universiti Putra Malaysia, Serdang, Malaysia

Kim Wei Chan Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia; Laboratory of Natural Medicines and Products Research, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Malaysia

Newlove A. Afoakwah Department of Food Science & Technology, University for Development studies, Tamale, Ghana

Suet Lin Chia UPM - MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia; Department of Microbiology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, Serdang, Malaysia

Rasheeda Hamid Abdalla Ahmed Tuberculosis Reference Laboratory, National Public Health Laboratory, Ministry of Health, Khartoum, Sudan

Voon Kin Chin Department of Medical Microbiology, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

Essa Mohammed AhmedIsmail Department of chemistry, College of Science, Sudan University of Science & Technology, Khartoum, Sudan

Helena S. Costa Department of Food and Nutrition, National Institute of Health Dr. Ricardo Jorge, I.P., Lisbon, Portugal; REQUIMTE-LAQV/Faculty of Pharmacy of University of Porto, Porto, Portugal

Taˆnia Gonc¸alves Albuquerque Department of Food and Nutrition, National Institute of Health Dr. Ricardo Jorge, I.P., Lisbon, Portugal; REQUIMTE-LAQV/Faculty of Pharmacy of University of Porto, Porto, Portugal; Instituto Universita´rio Egas Moniz, Lisbon, Portugal

Nataly Costa (de Almeida) Department of Food Technology, Federal University of Vic¸osa (UFV), Vic¸osa, MG, Brazil Arthur da Capela (Pompilio) Department of Food Technology, Federal University of Vic¸osa (UFV), Vic¸osa, MG, Brazil

Rita Carneiro Alves REQUIMTE-LAQV/ Faculty of Pharmacy of University of Porto, Porto, Portugal

Isabella Rosa da Mata Nutrition Department, Federal University of Health Sciences of Porto Alegre (UFCSPA), Porto Alegre, Brazil

Rindengan Barlina Indonesian Palm Crops Research Institute (IPCRI), Ministry of Agriculture, Manado, Indonesia

Ana Carolina da Silva Department of Food Engineering, Federal University of Triaˆngulo Mineiro, Uberaba, Brazil

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List of contributors

Kun Tanti Dewandari Indonesian Centre for Agriculture Postharvest Research and Development, Ministry of Agriculture, Bogor, Indonesia Yosvany Dı´az-Domı´nguez Faculty of Chemical Engineering, Technical University of Havana, Havana, Cuba Merve S¸eyda Karac¸il Ermumcu Akdeniz University Faculty of Health Sciences, Nutrition and Dietetics, Antalya, Turkey

Saeid Hazrati Department of Agronomy, Faculty of Agriculture, Azarbaijan Shahid Madani University, Tabriz, Iran Tjahjono Herawan PT Riset Perkebunan Nusantara (Indonesia Plantation Institute), Bogor, Indonesia Salwa Elamin Ibrahim Department of Home Economic, College of Home Economic, King Khalid University (KKU), Abha, Kingdom of Saudi Arabia

Norhaizan Mohd Esa Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia; Department of Nutrition, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

Norsharina Ismail Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

Siti Munirah Mohd. Faudzi Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia; Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

Neuza Jorge Department of Food Engineering and Technology, Sa˜o Paulo State University, Sa˜o Jose´ do Rio Preto, Brazil

Elina Ferna´ndez-Santan Faculty of Chemical Engineering, Technical University of Havana, Havana, Cuba Juliano Garavaglia Nutrition Department, Federal University of Health Sciences of Porto Alegre (UFCSPA), Porto Alegre, Brazil Mohamed A. Gedi Division of Food, Nutrition and Dietetics, School of Biosciences, University of Nottingham, Sutton Bonington Campus, Loughborough, United Kingdom; Faculty of Agriculture and Environmental Science, Somali National University, Mogadishu, Somalia Gamze Guclu Department of Food Engineering, Faculty of Agriculture, Cukurova University, Adana, Turkey Farhad Habibzadeh Department of Genetics and Plant Breeding, Faculty of Agriculture and Natural Resources, Imam Khomeini International University, Qazvin, Iran Sara Thamer Hadi Department of Food Science, College of Agriculture, University of Anbar, Ramadi, Iraq

Robert L. Jarret USDA/ARS, Plant Genetic Resources Unit, Griffin, Georgia, United States

Hasim Kelebek Department of Food Engineering, Faculty of Engineering, Adana Alparslan Turkes Science and Technology University, Adana, Turkey Nicholas M.H. Khong School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor, Malaysia Carini Lelis (Aparecida) Center for Food Analysis (NAL), Technological Development Support Laboratory (LADETEC), Federal University of Rio de Janeiro (UFRJ), Cidade Universita´ria, Rio de Janeiro, RJ, Brazil Sze Wei Leong UPM - MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia Fong Fong Liew Department of Oral Biology and Biomedical Sciences, Faculty of Dentistry, MAHSA University, Jenjarom, Selangor, Malaysia Gustav Komla Mahunu Department of Food Science & Technology, Faculty of Agriculture, Food and Consumer Sciences, University for Development Studies, Tamale, Ghana

List of contributors

xv

Abdalbasit Adam Mariod Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan; College of Sciences and ArtsAlkamil, University of Jeddah, Alkamil, Saudi Arabia

Ramo´n Piloto-Rodrı´guez Center for the Studies of Renewable Energies, Technical University of Havana, Havana, Cuba

Alisson Felipe Martins (Lima) Department of Food Technology, Federal University of Vic¸osa (UFV), Vic¸osa, MG, Brazil

Maylin Rondo´n-Macias Faculty of Chemical Sciences, Autonomous University of Chihuahua, Chihuahua, Mexico

Siti Nurulhuda Mastuki Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia; Department of Biological Sciences and Biotechnology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi, Selangor, Malaysia

Magdalena Rudzin´ska Poznan´ University of Life Sciences, Poznan´, Poland

Saeed Mollaei Department of Chemistry, Faculty of Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran Ira

Mulyawanti Indonesian Centre for Agriculture Postharvest Research and Development, Ministry of Agriculture, Bogor, Indonesia

T.P. Nkambule Department of Food and Nutrition Sciences, Faculty of Consumer Sciences, University of Eswatini, Luyengo, Eswatini Ogueri Nwaiwu Department of Food Nutrition and Dietetics, School of Biosciences, The University of Nottingham, Sutton Boninton Campus, LE12 5RD, Nottingham, United Kingdom; Alpha-Altis (Venture Member), Ingenuity Lab, The University of Nottingham, Jubilee Campus, Nottingham, United Kingdom M. Beatriz P.P. Oliveira REQUIMTE-LAQV/ Faculty of Pharmacy of University of Porto, Porto, Portugal Der Jiun Ooi Department of Oral Biology and Biomedical Sciences, Faculty of Dentistry, MAHSA University, Jenjarom, Selangor, Malaysia Daniele Paula (de Almeida) Federal Institute of Sa˜o Paulo (IFSP), Sa˜o Paulo, SP, Brazil

Ying Qian Poznan´ University of Life Sciences, Poznan´, Poland

Norazalina Saad UPM - MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia Serkan Selli Department of Food Engineering, Faculty of Agriculture, Cukurova University, Adana, Turkey; Department of Nutrition and Dietetics, Faculty of Health Sciences, Cukurova University, Adana, Turkey Onur Sevindik Department of Food Engineering, Faculty of Engineering, Adana Alparslan Turkes Science and Technology University, Adana, Turkey; Central Research Laboratory (CUMERLAB), Cukurova University, Adana, Turkey Mafalda Alexandra Silva Department of Food and Nutrition, National Institute of Health Dr. Ricardo Jorge, I.P., Lisbon, Portugal; REQUIMTE-LAQV/Faculty of Pharmacy of University of Porto, Porto, Portugal W.K. Solomon Department of Food and Nutrition Sciences, Faculty of Consumer Sciences, University of Eswatini, Luyengo, Eswatini Abdel Moneim Elhadi Sulieman Department of Food Engineering and Technology, University of Gezira, Wad Medani, Sudan; Department of Biology, College of Science, University of Hail, Hail, Kingdom of Saudi Arabia Danger Tabio-Garcı´a Faculty of Chemical Sciences, Autonomous University of Chihuahua, Chihuahua, Mexico

xvi

List of contributors

Haroon Elrasheid Tahir School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China Carolina M. Veronezi Department of Food Engineering and Technology, Sa˜o Paulo State University, Sa˜o Jose´ do Rio Preto, Brazil

Zou Xiaobo School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China

C H A P T E R

1 Unconventional oils production, utilization worldwide Haroon Elrasheid Tahir1, Abdalbasit Adam Mariod2,3 and Zou Xiaobo1 1

School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 3College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia

2

1.1 Introduction Oils and fats refer to a class of biological molecules named lipids that are described by low solubility in water and high solubility in nonpolar solvents (Sabikhi & Sathish Kumar, 2012). Demand for plant oils in the pharmaceutical, cosmetic, and biodiesel industries is growing, due to the fact they are precious natural sources of lipophilic compounds. Natural origin compounds of products used in daily life have higher acceptability by using the global network when compared with their synthetic counterparts (Go´rna´s & ´ Rudzinska, 2016). Palm, soybean, canola (rapeseed), sunflower seed, and palm kernel are the five major vegetable oils produced in the world (FAOSTAT, 2021). Moreover, the worldwide need for edible oils raises, the search for new or unconventional oils hastens. Particularly desirable are oil produce that grows in environments that most conventional oilseeds cannot, which include poor soil or drought. Many developing countries are looking for new oil-producing plants that flourish in their native climate and soil, increasing the wealth of agriculturalists and decreasing the nation’s dependence on imported oils. Furthermore, investors, processors, and consumers are seeking novel oils that have distinctive functional properties. Rice bran oil, Pequi oil, Pistachio oil, Allanblackia oil, and Jatropha oil represent the most promising or underutilized conventional oils that could increase the repertoire of vegetable oils available for food, cosmetic, or biodiesel uses (Ang, et al., 2015; Cassiday, 2018). There are numerous promising unconventional oil sources (e.g., annual plants, seeds herbs, vegetables, etc.) which still need further research

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00028-3

1

© 2022 Elsevier Inc. All rights reserved.

2

1. Unconventional oils production, utilization worldwide

and commercial application (Mariod 2005). For example, Acacia senegal (L.) seed oil (Nehdi, et al., 2012) and Capparis scabrida seed oil (Abreu-Naranjo, et al., 2020), pressed berry seed oils (Cheikhyoussef, et al., 2020), fig cultivars (Ficus carica L.) seeds oil (Hssaini, ¨ zcan, 2012), citrus seeds et al., 2020), Parkia filicoidea (Mkundi) seeds oil (Matthaus & O ¨ zcan, 2012), forage turnip (Raphanus sativus L.) oil (Silveira, et al., 2019) and (Matthaus & O Milo (Thespesia populnea L.) seed oil (Rashid, et al., 2011). Furthermore, an increasing quantity of the by-products produced from fruit processing industries, partly in the form of seeds, are commonly disposed of and might be used as sources of unconventional oil. Table 1.1 represents the list of conventional oils and their possible utilizations. TABLE 1.1 List of unconventional oils, production methods and their oil content. Types

Extraction techniques

Oil %

References

Meadowfoam seed

Soxhlet extraction with petroleum ether

31.5

Carlson et al. (1998)

Syagrus romanzoffiana seeds

Soxhlet extraction with N-hexane

52

Moreira et al., (2013)

Sapindus mukorossi kernel

Soxhlet extraction with hexane

39

Chakraborty and Baruah (2013)

Tomato seed

Soxhlet extraction with hexane

34

Giannelos et al. (2002); Panoutsou et al., (2008)

Maclura pomifera (Rafin.) Schneider seed

Soxhlet extraction with hexane

0.5
2.5

Saloua et al. (2010)

Tobacco seed

Soxhlet extraction with hexane

38

Panoutsou et al. (2008)

Pumpkin (Cucurbita pepo L.) seed

Soxhlet extraction apparatus was employed and hexane

45

Schinas et al. (2009)

Hyophorbe indica Gaertn. seeds

Soxhlet extraction with cyclohexane

3.09

Caro et al. (2020)

Dictyosperma album (Bory) Scheff seeds

Soxhlet extraction with cyclohexane

8.81

Caro, Petit et al., (2020)

Latania lontaroides (Gaertn.) H.E. Moore

Soxhlet extraction with cyclohexane

8.68

Caro, Petit et al., (2020)

Allanblackia floribunda seeds

Soxhlet extraction with Cyclohexane and hexane

60 2 68.2

Mouni, Njine et al. (2011); Pengou, Noumi et al. (2013); Loumouamou, Binaki et al., (2014)

Allanblackia floribunda seeds

Manual expeller

48.60

Wilfred, Adubofuor et al., (2010)

30.65

Mallek-Ayadi et al., (2018)

Melon (Cucumis melo Soxhlet extraction with L.) seeds hexane

(Continued)

Multiple Biological Activities of Unconventional Seed Oils

1.2 Oil production methods

3

TABLE 1.1 (Continued) Types

Extraction techniques

Oil %

References

Salvia sclarea and Salvia officinalis

Soxhlet extraction with hexane

19.7
35.21

ˇ Moazzami Farida et al. (2016); Zivkovi´ c et al. (2017)

Chia (Salvia hispanica Soxhlet extraction with L.) seeds petroleum ether

30.23
33.50 Ayerza (2009); Amato et al. (2015)

Chia (Sa´lvia hispaˆnica) seeds

Soxhlet extraction with hexane

37.78

Scapin et al. (2017)

Linseed seeds

Mechanical pressed

19.2 231.9

Kasote et al. (2013)

Jatropha curcas seeds

Twin-screw extruder/screw press expeller

33.73 273.14

Pradhan et al. (2011); Evon et al. (2013)

Jatropha curcas seeds

Soxhlet extraction with petroleum ether

44.6 252.1

Suresh et al. (2019)

Passion fruit seeds

Soxhlet extraction with n-hexane

22
30

Purohit et al. (2021)

Apple seeds

ultrasound technique with n-hexane

12.06
27.49 Go´rna´s et al. (2014)

Stinging nettle (Urtica dioica L.) seeds

Mechanical pressed

30.68

¨ zdemir (2012) Uluata and O

Laurel (Laurus nobilis),

Mechanical pressed

36.82

¨ zdemir (2012) Uluata and O

Hempseeds (Cannabis sativa) seeds

Soxhlet extraction with n-hexane

¨ zdemir (2012); Kosti´c et al. (2013) 31.48
29.56 Uluata and O

Radish (Raphanus sativus) seeds

Soxhlet extraction with n-hexane

42.64

Xanthium sibiricum Patr

Soxhlet extraction petroleum 42.34 ether

¨ zdemir (2012) Uluata and O Chang et al. (2013)

1.2 Oil production methods There are many preprocessing (cleaning, shelling, peeling, crushing, conditioning, flaking) are required before oil extraction from seeds. The main techniques used for unconventional oils include mechanical extraction (hydraulic press, screw press) and chemical extraction (solvent extraction). A simple mechanical press technology could be utilized for extracting the oil without additional processing. This technique is also described as cold pressing. The cold-pressing technique is not suitable for all types of seeds; some of the seeds required a complex process, for instance, a combination of pressing, cooking, and solvent extraction. The solvent extraction method has higher oil recovery efficiency (98%)

Multiple Biological Activities of Unconventional Seed Oils

4

1. Unconventional oils production, utilization worldwide

than the mechanical technique (70%) that’s the essential factor of 5% usage of mechanical extraction technique (Srivastava, et al., 2021). The main parameters that affect the mechanical extraction method, that is, heat and pressure. It is an energy-intensive method that needs high fixed and operational cost investment with low oil recovery. The mechanical extraction technique is the common procedure for extracting oil from seeds. Generally, the expeller or ram press or engine-driven screw press is employed for expelling or pressing oilseeds (Anwar, et al., 2019). The amount of extracted oil depends on the types of seed extraction techniques. Nonetheless, oil extracted by mechanical technique extraction required additional processing for filtration and degumming. The solvent extraction method is obtained high recovery and cost-effectiveness when n-hexane in a ratio of 5:10 (solvent:oilseeds) having high ignition (264 C) and flash temperature (218 C) (Anderson, 2011). Generally, the solvent extraction method is better than mechanical pressing due to the low supplementary costs and labor. Among the solvents used, hexane is the popular organic solvent for the extraction of oil due to the cost-effectiveness and low toxicity (Mahanta & Shrivastava, 2004). There are some more methods such as the microwaveassisted method (Jiao et al., 2014), ultrasound-assisted method (Goula et al., 2018), and supercritical CO2 extraction (Barrales et al., 2015). These techniques have been utilized for several types of oils seeds including pomegranate seeds oil, Preilla seeds oil, Sea mango oil, grape seeds and passion seeds oil, etc. these technologies have advantages such as vast extraction time, direct extraction ability, requires less solvent, lower energy consumption, and increase production rate and quality of extracted oil (Ramanadhan, 2005). Extraction of oil using enzymatic procedure using appropriate enzymes while crushing is attaining great interest due to its good environmental aspects for not generating volatile organic compounds (Jiao et al., 2014; Li et al., 2014; Goula et al., 2018). However, the major challenge of this technique is the cost of enzyme and it is required a long extraction time to release oil bodies (Mahanta & Shrivastava, 2004). Table 1.1 indicated the studies carried for oil extraction from various parts of plants or industrial by-products (e.g., seeds). It can be observed that most of the studies have found that chemical extraction methods were most convenient for the extraction of unconventional oil. The enzymatic extraction method is safe, green, and environmental aqueous extraction which is very essential for industrial purposes. The main extraction methods used for unconventional oil production are reported in Table 1.1.

1.3 Unconventional oil worldwide The oil content of seeds can be influenced by extraction techniques; for instance, the average oil content of Chia (Salvia hispanica L.) seeds was 20.30% by pressing and of 26.70% by solvent extraction (Ixtaina et al., 2011). In a study, Goula et al. (2018) applied ultrasound-assisted aqueous enzymatic extraction of oil from pomegranate seeds. The results showed the oil rate achieved by aqueous enzymatic extraction (15.33% g dry seeds) was comparable to the rate achieved by other extraction procedures (4.29
25.11% g). Maceration in n-hexane with orbital shaking at 150 rpm for 6, 12, and 24 hour, with or without heat at 60 C, was used for rambutan seeds oil extraction (Lourith et al., 2016).

Multiple Biological Activities of Unconventional Seed Oils

1.3 Unconventional oil worldwide

5

Scapin et al. (2017) compared solvent extraction, pressurized CO2 and compressed petroleum liquefied gas (LPG) for extraction of the chia oils. The highest oil content was achieved using hexane extraction followed by LPG (27.13% at conditions of 2.5 Mpa/40 C) while CO2 showed the lowest value (21.93%, at conditions of 25 MPa/60 C). The authors concluded that compressed LPG is a powerful solvent for the extraction of chia oil due to the high extraction rate and high antioxidant activity in a very short time. However, both types of solvents were capable of extracting oil rich in α-linolenic acid and bioactive compounds. In another work, very similar results were obtained when pressurized ethanol extraction (15 MPa, 35 C, 1 mL/min) (0.55 g/g) and ultrasound extraction (at 25 C) (0.60 g/g) techniques from the extraction of oil from passion fruit pulp (Ribeiro et al., 2020). Pereira et al. (2017) employed the subcritical compressed propane method to obtain the oil from sweet passion fruit (Passiflora alata Curtis) seeds. The extraction rate was also compared with ultrasound-assisted extraction and Soxhlet methods. Soxhlet using n-hexane showed the highest extraction rate (28.33%) followed by compressed propane (23.68%, at 2 MPa and 60 C) while ultrasound-assisted using ethanol showed the showed value (20.96%). Supercritical CO2 extraction alone or assisted with ultrasound were successfully used for the extraction of passion fruit (Passiflora edulis sp.) seeds oil (Barrales et al., 2015; dos Santos et al., 2019). Abaide et al. (2017) was extracted Avocado oil using supercritical CO2 and compressed liquefied petroleum gas. Compressed liquefied petroleum gas (at conditions of 293 K and 0.5 MPa, 10 minutes) recovered 60.5% oil (wet basis). Supercritical CO2 (at conditions of 313 K and 25 MPa, at 150 minutes) recovered 40 wt.% oil. Comparative extractions were carried out by using Soxhlet extraction (using hexane), supercritical extraction, and by mechanical pressure techniques (Fiori et al., 2014). Based on this study, SC-CO2 method might be used as a green technique to extract grape seed oils rich in health benefits compounds from winemaking by-products. similar results were observed by Coelho et al., (2018). Rice bran oil is derived from the outward coating, or bran, of rice (Oryza sativa). Generally, rice brane oil is produced by mechanical pressing or solvent extraction with hexane or isopropanol, while other procedures such as supercritical CO2 extraction and microwave-assisted extraction are under examination (Shukla and Pratap, 2017). For extraction of oil from oleaginous microorganisms (Trichosporon oleaginosus and an oleaginous fungal strain SKF-), several solvents including hexane, methanol, water, and chloroform/methanol (1:1 v/v) were analyzed to evaluate the appropriate solvent for oil extraction. Ultrasonication (50 kHz and power 2800 W) was compared with the common chloroform:methanol (2:1 v/v) extraction technique. The highest lipid content was 10.2% and 9.3% with water, 43.2% and 33.2% with hexane, 75.7% and 65.1% with methanol, 100% and 100% w/w biomass with chloroform/methanol was reached from T. oleaginosus and SKF-5 strain, respectively. These results showed that ultrasonication chloroform/ methanol extraction could be used as a powerful technique for lipid extraction from the microorganisms. Some other extraction techniques were used for oil extraction including laboratory-scale hydraulic press for Jatropha curcas and pennycress seeds oil extraction (Moser et al., 2009; Subroto et al., 2015), industrial extruder castor seeds oil extraction (Carlson et al., 1998; Berman et al., 2011), and microwave-assisted solvent extraction of sandbox (Hura crepitans) seed oil (Ibrahim et al., 2019). A few years ago, Amaranthus was exposed as a most

Multiple Biological Activities of Unconventional Seed Oils

6

1. Unconventional oils production, utilization worldwide

promising plant genus that may be a source of high-quality unsaturated oil and many other valuable components. Amaranthus oil can be extracted using nonpolar organic solvents, such as hexane and petroleum ether using the Soxhlet method or with SC-CO2 procedure (Venskutonis & Kraujalis, 2013). The oil may also be derived using pressing methods; but, in this case, the extraction rates are remarkably lower. Generally, hexane and petroleum ether are the most popular solvents used for the production of unconventional oil from seeds (Table 1.1), but in some cases, other organic solvents such as acetone and ethanol have been reported for the extraction of pistachio oil and Xanthium sibiricum Patr (Chang et al., 2013; Guedes et al., 2017). Mechanical press of the seeds and pulp followed by the filtration has also been described (Table 1.1).

1.4 Utilization of unconventional oil Several applications of unconventional oils have been reported (Fig. 1.1).

1.4.1 Potential medicinal uses Vegetable oils are commonly utilized in the cooking of food, cosmetics, pharmaceuticals, and chemical industries because the chemical components of unconventional oils have distinctive chemical characteristics, and they are important and might expand the other edible oil sources. Some types of novel sources of edible oils are essential because they can be utilized for the production of functional foods due to their content of phytochemicals, which are well-known antioxidative agents (Ramadan & Moersel, 2006). Most of the unconventional oils are consumed in their natural state, therefore, maintaining various minor components, which are usually removed from other oils during refining and processing. These types of oils have high oxidative stability due to the high content of antioxidants such as tocopherols (Warner and Frankel, 1987). The major health benefit

Extraction methods: Mechanical extraction Chemical extraction

Oil sources E.g. seeds

Enzymatic extraction Microwave assisted

Oils uses

method Ultrasound assisted method Supercritical CO extraction

FIGURE 1.1 Production and utilization of unconventional oils.

Multiple Biological Activities of Unconventional Seed Oils

1.4 Utilization of unconventional oil

7

substances can have either prooxidative (e.g., free fatty acids and hydroperoxides) or antioxidative (e.g., tocopherols, phenols, and phospholipids) (Ramadan & Moersel, 2006). Previous studies showed that chia oil reduces the complications caused by high-fat diet induced obesity (Citelli et al., 2016), enhances glucose and insulin tolerance in obese Wistar rats (Marineli et al., 2015). Nowadays, the rise of the global incidence of obesity and obesity-associated disorders, such as insulin resistance, type 2 diabetes, and cardiovascular diseases, has been attributed to metabolic imbalance and low grade and chronic inflammation (Poirier & Eckel, 2002; Dandona et al., 2004). A study carried out by Furlan et al. (2017) showed that the incorporating of Hass avocado-oil enhances postprandial metabolic responses to a hypercaloric-hyperlipidic meal in overweight subjects. Wong et al. (2014) evaluated the cytotoxic activity of kenaf (Hibiscus cannabinus L.) seed extract and oil against human cancer cell lines. The results demonstrated that kenaf seed extract and kenaf seed oil might be used as sources of natural anticancer materials. The workers suggested additional studies on using kenaf seeds and oil for antiproliferative properties. Serum lipid composition including cholesterol, triglycerides, and total lipid fatty acids was measured in rats consumed okra seed oil at a level of 10% in the caseinbased diet which was suitable regarding vitamins, minerals, and other nutrients (Srinivasa Rao et al., 1991). The control group was ingested with a casein-based diet in which groundnut oil was the source of fat. The serum lipid composition of the treated and control group was monitored for 90 days. The finding revealed that the serum cholesterol level of rats feeding with okra seed oil was substantially lower as compared to the control group. These results proved that okra seed oil consumption has a potential hypocholesterolemic effect (Srinivasa Rao et al., 1991). In vivo studies showed that mustard, rapeseed oils, low and high in erucic acid and corn oil could reduce cardiac risk factors (Watkins et al., 1995).

1.4.2 Potential food uses Recently, there is a great interest in the consumption and commercial utilization of Allanblackia (Clusiaceae) seed oil. The European Food Safety Authority confirmed that Allanblackia oil is suitable for human consumption (Crockett, 2015). The utilization of Allanblackia oil differs according to the county in which the species produced. In some African countries such as Tanzania, Nigeria, Sierra Leone, and parts of Ghana the oil is used for cooking. The excellent physicochemical properties of oils (including solid at room temperature; high stearic acid content) provide food products that contain its (i.e., vegetable-based dairy products, ice cream, spreads) health benefits compare with other oil that contains higher concentrations of lauric, myristic, and/or palmitic acids, which can increase blood cholesterol levels (Crockett, 2015). Also, a previous report showed that it can be used as an alternative for cocoa butter during the production of chocolate (Pye-Smith, 2009). The bioactive profile of Allanblackia seed oils for the presence, identity and/or quantity of potentially bioactive secondary metabolites, and pharmacological assessment of identified compounds indicate key guidelines for future research (Crockett, 2015). In 2014, Unilever produced the “Becel Gold” brand of margarine in Sweden, which comprises Allanblackia oil (Cassiday, 2018).

Multiple Biological Activities of Unconventional Seed Oils

8

1. Unconventional oils production, utilization worldwide

In a study, the potential use of Cucumis melo L. seeds as a new source of plant oils was investigated (Mallek-Ayadi et al., 2018). The outcome of the study indicated that melon seeds oil could be utilized as a substitute of plant oil, which might serve as raw material for food applications. Moreover, the melon seed oil is commonly used as cooking oil in some countries in Africa and the Middle East (Hemavatahy, 1992; Mallek-Ayadi et al., 2018). In a study, Nadeem et al. (2017) reported the feasibility of incorporating the chia seed oil into margarine. In this study, up to 20% of chia oil addition revealed no negative impacts regarding storage. Besides, the fatty acid composition was improved, with higher ω-3 fatty acid contents and more antioxidant stability. Chia seed oil was also used in ice cream production (Ullah et al., 2017). Black cumin and coriander oils were used as natural antioxidants to improve the thermal stability of high linoleic corn oil (Mohamed et al., 2014). rambutan (Nephelium lappaceum) is an essential fruit tree in Thailand, mainly the cultivar “Rongrien.” It seeds found to rich in edible fat with a bitter taste that might be an appropriate alternative in the food industry (Solı´s-Fuentes et al., 2020). Based on the findings of Solı´s-Fuentes et al. (2010), rambutan seed fat could be used in food processing (Solı´s-Fuentes et al., 2010). The uses of some unconventional seeds, such as hemp, radish, terebinth, stinging nettle, and laurel enhance the quality, stability, and safety of food pro¨ zdemir, 2012). More recently ducts based on the chemical composition, etc. (Uluata & O rice bran oil is utilized as a novel carbon source for microbial production of vitamin B12 (Hedayati et al., 2020). A previous study showed that the Pequi oil can be enzymatically modified using Lipozyme in order to incorporate stearic acid in the sn-1,3 position of triacylglycerols and produce a cocoa butter-like fat (Facioli & Gonc¸alves, 1998).

1.4.3 Potential cosmetic uses Recently, the oil of Allanblackia was used to produce soap (Adubofuor et al., 2013). Linseed (also known as flaxseed) with oil content raged between 36% and 40%, usually used for the production of many products such as paints, varnishes, inks, soap, etc. (ElBeltagi et al., 2007; Nagaraj, 2009; Kasote et al., 2013). Recently, great attention has been given to agricultural residues as sources of natural antioxidant products to produce sustainable products appropriate for industrial purposes; specifically for personal health products that are in high demand, comprising cosmetics, to substitute artificial raw constituents. Lourith et al. (2016) was studied the potential use of rambutan seed fat as cosmetics components. The results indicate the possibility of using rambutan seed fat for cosmetic products and its appropriateness as novel raw material for the personal care industry. Furthermore, rambutan seed fat is similar to other vegetable oils and cosmetic constituents and is compatible with other cosmetic materials. According to the results of a study carried out by Go´rna´s et al. (2013), the cold-pressed Japanese quince seed oil could be used in pharmaceutical and cosmetic industries. Neem seed oil was used as biopesticides for controlling homopterous sucking pests of Okra (Abelmoschus esculentus (L.) Moench) (Indira Gandhi et al., 2006). However, further field research is required to confirm it and to understand the mechanism. The oil extracted from the Pequi kernel is characterized by a pleasant light flavor and it is utilized in cosmetic production (Guedes et al., 2017).

Multiple Biological Activities of Unconventional Seed Oils

1.4 Utilization of unconventional oil

9

1.4.4 Potential biodiesel fuels uses A previous study showed that pennycress and meadowfoam-derived biodiesel fuels were mixed with the other biodiesels to simultaneously ameliorate cold flow, oxidative stability, and viscosity shortages inherent to the individual fuels (Moser, 2016). Overall, complementary mixing improved fuel characteristics including cold flow, kinematic viscosity, and oxidative stability of biodiesel. In a study, biodiesel production from yellow horn (Xanthoceras sorbifolia Bunge.) seed oil utilizing ion exchange resin as a heterogeneous catalyst was examined (Li et al., 2012). The outcome showed that microwave-assisted transesterification procedure catalyzed by high alkaline anion exchange resin was a green, effective and low-cost technique for biodiesel production. Moser and Vaughn (2010) reported the feasibility of using Camelina sativa oil as biodiesel and as blend components in ultra-low-sulfur diesel fuel. In this study, the quality of Camelina oil alkyl esters, both pure and mixed with petrodiesel, was comparable to other ordinarily encountered biodiesel fuels, for example, soybean, canola, and palm oil methyl esters. Castor (Ricinus communis L.) oil is one of the most promising unconventional nonedible oil due to high seed production and produce. However, few types of research are conducted on the potential use in biodiesel as it neat or mixed with petrodiesel, many of which are due to its extremely high content of ricinoleic acid (toxic to humans and animals) (Berman et al., 2011). The potential of utilization of papaya seed oil and stone fruit kernel oil as nonedible feedstock for biodiesel production has been reported (Anwar et al., 2019). Other popular unconventional oils used in biodiesel include Calophyllum inophyllum, desert date, Moringa oleifera, rubber seed, fish oil, jojoba, neem, Eruca sativa, Jatropha curcas, papaya seed oil, Pongamia pinnata, Madhuca indica, Salvadora oleoides, and tobacco apricot seed (Usta, 2005; Godiganur et al., 2009; Avinash et al., 2014; Anwar et al., 2019). In a study, the future potential in the production of biodiesel of tomato seed oil and tobacco seed oil has been reported (Panoutsou et al., 2008). Anjum et al. (2019) reported that the Argemone mexicana seed oil biodiesel may use as a potential substitute for natural diesel fuel. Some unconventional oils used in feedstocks have been studied include Egusi (Colocynthis citrullus L.) seed kernel oil (Giwa et al., 2014); pennycress seeds oil (Moser et al., 2009); Camelina seeds oil, (Moser & Vaughn, 2010); castor seeds oil (Carlson et al., 1998; Berman et al., 2011); pumpkin (Cucurbita pepo L.) seed oil (Schinas et al., 2009); tobacco seed oil (Panoutsou et al., 2008); tomato seed oil (Giannelos et al., 2002; Panoutsou et al., 2008); Syagrus romanzoffiana oil (Moreira et al., 2013); Moringa seeds oil (Rashid et al., 2008); kenaf oil (Knothe, Razon et al., 2013) and meadowfoam seed oil (Carlson et al., 1998). All of these unconventionally produced biodiesel with fatty esters of different chain lengths and unsaturation and, hence, properties. More recently, the microwave-assisted solvent extraction of nonedible sandbox (Hura crepitans) seed oil was evaluated (Ibrahim et al., 2019). Based on the findings of this study, sandbox seed oil could serve as feedstock for biodiesel and other oleochemical production. Another nonedible oil was obtained from Firmiana platanifolia L.f. and Pennycress (Thlaspi arvense L.) were successfully used as components of biodiesel production (Chang et al., 2013; Zhang et al., 2015; Zanetti et al., 2019). The findings showed that F. platanifolia L.f. is a prospective species to be utilized as a biodiesel feedstock in China. Hoang et al. (2021) reported the potential utilization of blend comprising 20% rice bran oil biodiesel and 80% petrodiesel fuel, both in volume might be the effective combination in view of the techno-economic aspects of diesel engines.

Multiple Biological Activities of Unconventional Seed Oils

10

1. Unconventional oils production, utilization worldwide

Oils of oleaginous microorganisms are a good substitute to vegetable oils for biodiesel production. In a study, fungus Epicoccum purpurascens AUMC5615 isolated from Egypt presented higher oil content (80%) and carotenoids especially when grown on 4% sucrose under continuous illumination (Koutb & Morsy, 2011). The fatty acid profile of this oil encourage the use of this promising fungal in biodiesel production.

1.5 Conclusion This chapter summarizing the various data on the production of conventional oils as well as their utilization in food, medicinal, pharmaceuticals, biodiesel, and other uses. Most of the fruit seeds are obtained from edible fruits as a by-product and they have the potentials to be utilized directly in the food and pharmaceutical industries. Therefore, it could promote environmental sustainability, more cost-effective utilization of harvested plant products, and improved economic profits. The utilization of fruit by-product can not only reduce the aggregation of waste but it also may make extra income for the fruit processing enterprises. Some of the seeds are rich in oil and may be used as sources of functional oils and biodiesel components. However, many seeds are still required comprehensive research before being used in food industries and other industrial purposes. The solvent extraction method is the main technique used for the production of unconventional oils from seeds, however, other techniques could be effectively used for the production of oils rich in functional compounds such as tocopherol and polyphenol compounds. Due to the rapid development, the worldwide need for petrodiesel for diesel engines is growing as of the limited reserves of fossil fuels, increasing prices of crude oils, and environmental concerns. The utilization of vegetable oil as the component of biodiesel production is not appropriate as the need for edible vegetable oils is greatly increasing. Thus, great attention has been given to alternative feedstocks such as unconventional oils, which will not lead to the food crisis as a result of economic imbalance. Overall, we believe this chapter will be a good guideline to identify unconventional oils with their oil contents for future food, pharmaceutical biodiesel industries.

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C H A P T E R

2 Biological activities, definition, types and measurements Abdalbasit Adam Mariod1 and Haroon Elrasheid Tahir2 1

Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 2School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China

2.1 Introduction Biological activity is “the capacity of a specific molecular entity to achieve a defined biological effect” on a target (Jackson et al., 2007), and it is measured by the activity or concentration of a molecule required to cause that activity, and biological activity is always measured by biological assay. In the pharmaceutical sciences, biological or pharmacological activity describes the beneficial or harmful effect of a drug on an organism. Among the various properties of chemical compounds, the biological or pharmaceutical activity plays a prominent role for the compounds in therapeutic applications, however, chemical compounds show some adverse and toxic effects that may prevent their use in therapeutic medical applications (Miller-Keane Encyclopedia and Dictionary of Medicine, Nursing, and Allied Health, 1993). Biological activity is always depend on the dose that given to the living organism, so it is logically to show either beneficial or adverse effect that range from low to high. Activity depends mainly on the action of the “absorption, distribution, metabolism, and excretion,” (ADME) measurement. To be an active medicine, a compound not only must be active against a target, but also possess the exact ADME characteristics that let it be utilized as a drug (Jagan et al., 2012). Bioactive glasses used in dentistry implantation preferred to have high specific surface area to cause faster solubility of the material, show of ions around, and build up protein adsorption ability. All these elements lead to bioactivity of bioglass coatings. In addition, tissue mineralization (bone, teeth) is promoted while tissue forming cells related with bioglass materials (Chakraborty et al., 2019). Biological activity occurs as a result of certain effects from exposure to a molecule. These influences a metabolic or physiological response. Bioactivity can be studied in vivo and in vitro. Only in vivo accurate responses to the bioactivity of a specific compound are available (Fagundes et al., 2020; Wolfram & Trifan, 2018). The evaluation of biological

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activity requires test systems, which are in the body of the organism, and acquire signals, mainly spectrophotometry, or photometry, in parallel experiments of different concentrations of test samples and comparison with control samples. In such tests, computational systems are needed to process, store, sort and visualize data using appropriate mathematical or statistical models to interpret and evaluate results and link sets of data and signals from various origins (Wolfram & Trifan, 2018).

2.2 Types of biological activities 2.2.1 Antimicrobial activity Antimicrobial activity can be defined as a collective term for all active principles (agents) that inhibit the growth of bacteria, prevent the formation of microbial colonies, and may destroy microorganisms. According to Mucha et al. (2002), the term “antimicrobial” uses the term “antibacterial” or “antifungal”. From the Hohenstein Institute, it is suggested that antimicrobial activity is a condition in which an active agent has a harmful effect on a microorganism. When the active agent only affects bacteria or fungi, he adds, it is known to have antibacterial or antifungal activity, respectively. It can also be said that up to the moment there has not been a universal agreement on a comprehensive definition that constitutes a significant growth or decline in the bacterial colony. The prerequisite for a vital factor is that the specific bacterial population remains constant in terms of its size. However, in practice, this is extremely rare because vital biological systems are in efficient equilibrium and react to any change in their life system either by growth or death. Final antimicrobial treatments are commonly used in specialized fibrous products of a protective nature. However, consumer perceptions of an increased knowledge of hygienerelated issues have led to an increased use of therapeutic products for many consumer products. These products primarily aim to avoid the harmful effects of microbial cell degradation, reduce the occurrence of bacteria, reduce odor formation as a result of bacterial decomposition of sweat, and avoid bacterial infection. In practice, antimicrobial finishes can be used in many applications, especially in order to protect the fibrous products from the effects of microbes and especially the type of fungi. Products that can be protected include clothing, tents, floors, curtains, and bathrooms (Elmogahzy, 2020). Common microbial finishing agents are related to disinfectants that are used to wash clothes that come in contact with the skin. In applications such as outdoor and sports, it is important to prevent the build-up of odors on clothes. In these cases, antimicrobials work by preventing the bacterial breakdown of sweat on clothing. Fibrous products that act as antimicrobials can be divided into two types, (1) passive products and (2) active products. Negative products do not contain a specific biologically active substance. They are based on fibers that are naturally antimicrobial. In this class, bacterial cells are prevented from attaching to the surface of the fibers due to the surface structure and the lack of absorption of the fibers. Active products contain specific end substances that act as antimicrobial agents that attack microorganisms. These are highly specialized agents that target specific microorganisms. Many finishing agents are used in the

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food and cosmetic industries. Common antimicrobial agents include oxidizing agents. The main criteria for these factors include low toxicity risks and resistance to washing and dry cleaning (Elmogahzy, 2020).

2.2.2 Antibacterial and antifungal activity In this study, different concentrations of n-hexane, chloroform, ethyl acetate, methanol and aqueous extracts of the medicinal plants of Zingebir officinal, Nigella sativa, and Matricaria recutita, were studied and its antibacterial activity was reported using an agar diffusion technique against (Staphylococcus aureus, Enterococcus faecales, Escherichia coli, Klepsiella sp., Proteus sp., Pseudomonas sp., Salmonella sp., Serratia sp., Citrobacter sp.). The results indicated that the alcohol extracts had high bacterial antibody. The physiochemical screening of plant extract concentrates was carried out to choose the best one. The results showed that there are some differences in their components. The ethyl acetate extract of Ethiopian ginger contained alkaloids, anthraquinone glycosides, coumarin, flavonoids, saponins, tannins, and triterpenes. The Ethiopian Black Seed chloroform extract contained coumarin, flavonoids, triterpene and sterols. The methanolic extract of Sudanese Matricaria retutica contained alkaloids, anthraquinone glycosides, coumarin, flavonoids, saponins, tannins, triterpens and sterols. The study revealed the absence of cyanogen glycosides in the three extracts. This study demonstrated that the aforementioned plants and their pure compounds have antimicrobial activities, and possibly antiinflammatory and other biological activities worthy of attention (Kakil, 2013). To study the toxicity of essential oils on some insect pests, some biological tests were performed and showed a very high effect, increasing significantly with dose and exposure time. Equally, the repellent effect test showed that the volatile oil extracts are a powerful insect repellant. In addition, both the liquid and vapor phases of volatile oils were found to have inhibitory effect on the growth of fungal strains. In light of these results, the studied plant is promising as a source of natural pesticides and fits well as a biochemical alternative to control harmful agricultural pests and insects (Yakhlef et al., 2020). The antibacterial activity of five foodborne bacteria (Bacillus cereus, Listeria monocytogenes, Staphylococcus aureus, Escherichia coli, and Salmonella anatum) were studied in vitro on 46 extracts of spices and medicinal herbs using the agar diffusion method and their total phenolic compounds were estimated. The study demonstrated that these herbal and spice extracts contained high levels of phenols and demonstrated antibacterial activity against foodborne pathogens. The Gram-positive bacteria were generally more sensitive to the tested extracts than the Gram-negative ones. The most resistant were Escherichia coli. The study showed a positive relationship between the antibacterial activities and the phenolic content of the extracts tested against each bacterium, meaning that the activity is related to the phenolic content (Shan et al., 2007).

2.2.3 Antioxidant activity Antioxidants are organic or chemical compounds that prevent or delay the oxidation process of compounds that produce free radicals with a harmful effect. Antioxidants are of two types, which are synthetic and natural. In general, synthetic antioxidants are compounds with phenolic

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structures with different degrees of alkyl substitution, while natural antioxidants can be phenolic compounds, nitrogen compounds or carotenoids (Gu¨lc¸in et al., 2010). Many researches and studies have been conducted on large groups of plants to find out their natural antioxidants. There are some plants, wild and medicinal herbs of particular interest for small countries because they may be used in the production of raw materials or preparations containing phytochemicals with great antioxidant capabilities. Some studies have been conducted on certain species such as sage as possible sources of phenolic antioxidants (Exarchou et al., 2002). There is no single method that can predict antioxidant efficacy to characterize antioxidant properties in vitro and in vivo, therefore more than one method is recommended and more scrutiny should be taken in extrapolating laboratory data. The spectrophotometric technique, total antioxidant activity (TAA), or equivalent antioxidant activity of Trolox (TEAC) involves generating a long-lived specific radical chromophore from 2,20 -azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) By controlled chemical oxidation (Luximon-Ramma et al., 2002). Koleva et al. (2002) There is no single method that can predict antioxidant efficacy to characterize antioxidant properties in vitro and in vivo, therefore more than one method is recommended and more scrutiny should be taken in extrapolating laboratory data. The spectrophotometric technique, TAA, or TEAC involves generating a long-lived specific radical chromophore from 2,20 -azinobis- (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) By controlled chemical oxidation. There is a study conducted to extract the phenolic compounds from the oil of Sclerocarya birrea nut, either by using ultrasound or by magnetic stirring, the first method gave a greater amount of the total phenolic compounds, and when adding the extracts obtained to sunflower oil it inhibited the oxidation and antioxidant activity, which reduced the damage. Oil compared to oil without extract. When comparing the effectiveness of these extracts with the synthetic antioxidant BHA, all the extracts at different concentrations showed a significantly better effect on the oxidative stability of the oil (Mariod et al., 2008). M. oleifera antioxidant activity is attributed to the presence of several types of antioxidant constituents. Related to the oil antioxidant potential, monopalmitic acid, oleic acid, tri-oleic triglycerides are the most significant compounds. Hydrocarbons and quercetin isolated from the essential oil of Moringa seeds act as a necrosis factor for cancer cells, but they showed a radical removal effect for tumors. Another study compared the antioxidant efficacy of moringa seed oil and seed powder and its residues. The antioxidant activity was determined using the 1,1-diphenyl-2-picrylhydrazy (DPPH) assay and the result confirmed that moringa seed oil possesses the strongest antioxidant capacity. The difference in the antioxidant activities between the different samples of Moringa can be attributed to the tocopherol contents, the type of phenolic compounds and the shape of the antioxidant compounds. Moringa oil has shown high free radical activity.

2.2.4 Antitubercular activity Tuberculosis (TB) remains one of the most common causes of ailment and mortality in humans, and it is estimated that approximately one-third of the world’s population has been infected with Mycobacterium tuberculosis (Organization, 2013). Egharrevba et al. (2015)

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studied the antitubercular activity of M. oleifera seed oil. The oil was also screened against local strains of Mycobacterium tuberculosis by tetrazolium dye microbroth dilution assay. Organism viability and media sterility control were also set up. The minimum concentration at which there was no growth of Mycobacterium was taken as the MIC. The result of antitubercular activity indicated that the oil was active against locally isolated strain of Mycobacterium tuberculosis at 25% (v/v), whereas that of the control drug, rifampicin, was 0.09 μg/mL. Many researchers reported the antibacterial activity of fatty acids and oily substances, particularly for oleic acid and its derivatives. Similarly, Esquivel attributed the antitubercular activity of the hexane extract of Citrus sinensis peel to the palmitic acid, decanal, caryophyllene oxide, and cis-limonene oxide contained in the extract. Other research reported the antitubercular activity of linoleic and oleic acid at 100 μg/mL. Therefore, the antitubercular activity of the seed oil of M. oleifera could be due to the oleic acid and palmitic acid content (Egharevba et al., 2015). Hypothetically the main place of action of fatty acids is the cell membrane, where it interferes with the energy transport system by disrupts the electron transport chain, and oxidative phosphorylation. Fatty acids membrane action might also inhibit enzyme activity, impair nutrient uptake, produce hazardous products of peroxidation, and autooxidation, and/or directly lyse bacterial cells. Certain investigation attributed fatty acid activity on inhibition of oxygen uptake and stimulation of amino acid uptake into the cell. Taken into account the above mentioned information, M. oleifera oil could be exhibiting its actions through one or more of these mechanisms (Mehta & Agrawal, 2008).

2.2.5 Antiinflammatory activity A study was conducted on the aerial parts of Helichrysum stoechas (L.) Moench to find out their content of phenolic compounds, extracted with ethyl acetate (EAE) and butanolic (BuE), and for antioxidant and antiinflammatory activities, where EAE extract showed the highest levels of polyphenols and flavonoids. In-depth studies were carried out by LCESI-Ms to find out the type of phenols, as many vital phenols were discovered, including isoquercitrin, rutin, ferulic acid and chlorogenic acid. These extracts demonstrated significant inhibition of Croton oil-induced otosclerosis of 86% and 64%, respectively, and significantly reduced infiltrating leukocytes by 84% and 66% of inhibition, respectively. These extracts significantly stopped protein denaturation and stabilized the erythrocyte membrane. In addition, each of the two extracts was shown to have an antioxidant effect by scavenging hydrogen peroxide, hydroxyl radical and super-anion roots. According to the results of this study, it can be said that H. stoechas is a natural source of antioxidants and a powerful antiinflammatory agent (Kherbache et al., 2020). Medicinal plants form the basis for many medical treatments and a precursor for most drugs. This study investigated the antiinflammatory and antioxidant characteristics of the root and bark extracts of Vitex grandifolia. Soxhlet extraction was utilized to obtain the crude extracts. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, hydrogen peroxide and phosphomolybdenum (PM) assays were used to evaluate antioxidant properties. Total phenolic content determination was by the Folin
Ciocalteu method. A study was conducted to investigate the fact that carrageenan has an antiinflammatory activity in day old chicks. The ethanolic extracts

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of Vitex grandifolia roots and bark showed effective antioxidant activity in DPPH and PM assays. The bark extract was a better antioxidant than the root extract in the peroxide test. Both extracts showed fresh amounts of the phenolic compounds of root and bark extracts. As for its antiinflammatory action, the bark extract has proven superior to the root extract. The bark extract that gave the best antiinflammatory activity was fractionated using butanol, ethyl acetate and hexane to determine the fraction in which the antiinflammatory substances were concentrated. ED50 fractions were in the order ethyl acetate ,butanol. hexane. The results obtained showed that both root and bark extracts were effective antiinflammatory and antioxidant agents and proved their use in folk medicine to treat inflammatory-related diseases (Amo-Mensah et al., 2020). A recent study was conducted in the year 2020 AD aimed at the simultaneous evaluation of the antioxidant and antiinflammatory activities of hops (Humulus lupulus) extracts by different solvents. The aqueous and ethanol extracts were prepared using hot water and ethanol with different concentrations (55%, 75%, 95%), respectively. The biologically active compounds were estimated and were alpha-acid, beta-acid, total phenol content, and flavonoids. The study revealed that, ethanol extracts have higher antioxidant activities than aqueous extracts. Different ethanol extracts showed the highest antioxidant activities in experiments with different free radicals. For antiinflammatory activities, it was low for all extracts except for TNF-α secretion, ethanol extracts showed higher antiinflammatory activities than aqueous ones. The study sees the importance of exploring a possible mechanism to improve the ethanol extraction procedure in the future (Wu et al., 2020).

2.2.6 Anticancer activity Cancer is one of the most harmful diseases leading to human death in developing as well as developed countries. The number of cancer cases is estimated to increase by about 70% in 2035. During the last twenty years, the use of plant products, has gained an increased interest in cancer therapy. Several compounds isolated from herbaceous medicinal plants were found to possess anticancer activities (Khan et al., 2019). As above discussed, Moringa oil showed different biological activities. For this reason and because of the scarcity of anticancer studies on Moringa seeds oil, many researchers have been focused their work to explore the potential anticancer activity of the oil. Elsayed81 assessed the anticancer properties of M. peregrina seed oil on different cell lines. The cell lines included: breast cancer (MCF-7); liver cancer (HepG-2); colon cancer (CACO-2); cervical cancer (HeLa) and mouse fibroblasts (L929). Different concentrations (15
1000 μg/mL) of M. peregrina oil extracted from seed kernels were evaluated for their cytotoxic effect against cell lines (Elsayed et al., 2015). The endocarp of the rambutan Nephelium lappaceum fruit extract have been studied for their anticancer properties against human hepatocytic carcinoma (HepG-2) cells. This study was carried out by various analytical methods including phytochemical qualitative analysis, cell viability assay 3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide (MTT), apoptotic nuclear staining 40 ,6-diamidino-2phenylindole (DAPI), DNA fragmentation assay, attenuated total reflection (ATR) and gas chromatography-mass spectrometry (GC-Ms). ATR and GC-Ms revealed the presence of functional groups and nine compounds, respectively, in the methanol endocarb extract of rambutan. The study also showed that the methanolic extract of endocarp has a control in

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cell proliferation and caused HepG-2 cells to shrink from polygon to spherical shape. DAPI analysis revealed that the methanolic extract of endocarp increased nucleus fragmentation and DNA fragmentation, leading to cell death. The methanolic extract is more effective as an anticancer than other extracts and can be used successfully in future drug delivery systems and other biomedical concerns (Perumal et al., 2020). A study was conducted to find out the phenolic properties, antimicrobial, antioxidant and anticancer activity of ethanolic extracts of ground artichoke. Ethanolic extracts were prepared from vessels and artichoke bracts by the repeated extraction method. The amounts of phenol and flavonoids were calculated using HPLC. The extracts’ antimicrobial, oxidative, and anticancer properties have also been studied. The results of the study showed that the amount of phenol and flavonoids in the ethanolic extract of bracts was greater than that of the vascular extract. The study revealed that there are thirteen phenolic compounds in the bracts extract and that the catechin compound is the main one, while eight compounds were identified in the vessel extract. Vascular ethanol extracts showed strong antibacterial activity against seven types of foodborne pathogenic bacteria, and antifungal activity against eight types of mycotoxic fungi, artichoke extract showed strong antioxidant activity compared to vascular extract. Similar trends were observed against cancer cell strains, bracts and artichoke vessels contain sufficient amount of phenol and flavonoid contents and have demonstrated antimicrobial, antioxidant and anticancer activities which are essential and important in nutritional and pharmaceutical applications (Shallan et al., 2020).

2.2.7 Antiaging The dietary consumption of grape and its products is associated with a lower incidence of degenerative diseases such as cardiovascular disease and certain types of cancers. previous studies has concentrated on the bioactive phenolic compounds in grape. Anthocyanins, flavanols, flavonols and resveratrol were found the main grape polyphenols due to their biological activities, such as antioxidant, cardioprotective, anticancer, antiinflammation, antiaging, and antimicrobial properties (Xia et al., 2010). It was found that polyphenolics presented in foods might be beneficial in reversing the course of neuronal and behavioral aging. Due to their notable antioxidant activity, such as scavenging free radical, they could prevent organs and tissues from oxidative damage, and modify the body negative mechanism of redox status. The evidences were obtained by observing the behaviors of rats, from age 19 to 21 months. After drinking the 10% grape juice, improvements were detected on release of dopamine from striatal slices, as well as cognitive performance in the Morris water maze, while the 50% grape juice improved action capacity (Shukitt-Hale et al., 2006; Xia et al., 2010). A study was conducted to find out the effects of wild and cultivated Andean plants on a group of enzymes such as collagenase, elastase, hyaluronidase, and tyrosinase, in addition to the antioxidant capacity, in order to find out the antiaging sources in order to develop them as cosmetic products from natural sources. In the study, 65 samples of methanol extracts were selected from the fruits of 35 Andean plants in different stages of growth. Anticollagenase, antielastase, antihyaluronidase, and antityrosinase activities were

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determined by fluorescence spectrophotometric and fluorescence assays. The antioxidant capacity was studied and known by the oxygen radical uptake capacity (ORAC) and TEAC assays. Total phenolic compounds were quantified by the Folin
Ciocalteu method. Through the results of the study of inhibitory activity against enzymes associated with skin aging and antioxidant properties, it became evident the importance of Alchornea triplinervia, Gaultheria erecta, Rubus compactus, and Ugni myricoides, as promising plants and could be sources that delay the effects of aging. In addition, the ripening stage of fruits has an effect. On the quantity, quality and properties of the extracts in a statistically significant manner. The study proved that immature Andean plants act as active antioxidants and have inhibitory enzyme activity. The results of this study highlight possible ways to add value to the fruits of 35 wild and cultivated plants in the Andes Mountains based on their potential use as antiaging ingredients in cosmetic formulations. We need to conduct additional, in-depth studies that study the safety and how to isolate the active compounds, enabling new cosmetic products that are effective in antiaging (Bravo et al., 2016).

2.2.8 Antimalarial activity Work with dried and ground leaves of R. retinorrhoea from Saudi Arabia, which were extracted using dichloromethane, suggests that a modest antimalarial activity can be obtained. Partitioning of the dichloromethane extract between hexane and acetonitrile, followed by silica gel column chromatography (benzene/ethyl acetate) yielded the following five flavonoids, 7-O-methylnaringenin (Gulmez et al., 2006), eriodictyol, 7,30 -O-dimethylquercetin, 7-Omethylapigenin, 7-O-methylluteolin, and the biflavone (2 S,200 S)-7,700 -di-O-methyltetrahydro amentoflavone. The biflavone exhibited moderate antimalarial activity with an IC50 of 0.98 μg/ mL against Plasmodium falciparum (W2 clone) and weak activity against P. falciparum (D6) with an IC50 of 2.8 μg/mL, but was not cytotoxic (Gulmez et al., 2006), showed weak antimicrobial activity against Candida albicans, C. krusei, Staphylococcus aureus, Mycobacterium smegmatis, M. intracellulare, and M. xenopi. Given the global interest in environmentally and economically sustainable antimalarial treatments, further work is needed on ascertaining whether this desirable bioactivity can be obtained from the numerous sumac species indigenous to malarial regions of sub-Saharan Africa (Rayne & Mazza, 2007).

2.2.9 Antiproliferative activity Antiproliferative activity is known as the ability of a compound to stop cell growth, that is, not to allow cells to proliferate rapidly, while cytotoxicity refers to damage to cells which means elimination. Anticancer agents kill cancer cells, so chemotherapy is a cytotoxic treatment. Chemotherapy generally aims to stop cell proliferation, stopping the cytostatic carcinogenesis process Studies of C. molle extract have been conducted, revealing that they have antiproliferative activity on a variety of tumor cell lines. There are results of leaf extracts showing that they are moderately active against cervical cancer, chronic myeloid leukemia, hormone-dependent breast cancer, while being very active against transitional cell carcinomas in the urinary bladder cell line. Studies have also demonstrated that C. molle extract has moderate activity against HPV-infected cervical cancer cells (Ueda et al., 2002).

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2.2.10 Hypoglycaemic activity Nine European plants were selected to be screened for hypoglycaemic activity. The selection was made according to the traditional method of use as found in the research literature. Plant extracts from the dried substance were prepared by boiling with water or soaked with 80% ethanol alcohol. Male Swiss rats were administered these extracts orally with glucose after the extracts were administered by oral gavage. Four of these extracts improved glucose tolerance and were extracts from Adiantum capillus veneris, Daucus carota, Galega officinalis, and Juglans regia. Further investigation will be focused on bioguided isolation of active fractions (Neef et al., 1995). In our experiments, 30 hypoglycaemic medicinal plants (known and less known) have been selected for thorough studies There are experiments conducted on ethanol extracts of herbal samples. It was found that alloxan reduces blood glucose within 2 weeks in diabetic albino mice. The results showed that the following plant extracts reduced blood glucose: Coccinia indica, Tragia involucrata, G. sylvestre, Pterocarpus marsupium, T. foenum-graecum, Moringa oleifera, Eugenia. The results of these studies help to reduce blood sugar (Kar et al., 2003).

2.2.11 Hypocholesterolemic activity There is a study conducted on grape seeds, where the compound proanthocyanidin was extracted as a dietary supplement and was added by 0.5% or 1.0% to see to what extent it could reduce the level of TC in the plasma and the level of triglycerides. The results indicated that the analyzes of the western blot and the real-time polymerase chain reaction (PCR) showed that GSP did not affect the protein bound to the sterol regulatory component and the low-density lipoprotein receptor (Jiao et al., 2010). A study was conducted to investigate the way by which hawthorn fruit lowers serum cholesterol in hamsters. In this study a control group was fed a semisynthetic diet containing 0.1% cholesterol while the studied group was fed on the same diet besides addition of 0.5% hawthorn fruit aqueous ethanolic extract for 4 weeks. Serum total cholesterol (TC) and triacylglycerols (TGs) were decreased in hawthorn fruit group as compared with the control (P , 0.05). The results showed that adding aqueous ethanol extract to hawthorn fruit resulted in greater excretion of neutral and acidic sterols. Enzymatic tests also indicate that there are ways to reduce cholesterol in the blood by the action of hawthorn fruit extract and that this action involves greater excretion of bile acids by the higher regulation of hepatic cholesterol 7α-hydroxylase (CH), and inhibition of cholesterol absorption by the lower regulation of intestinal acyl CoA: cholesterol activity. Acyl transferase (ACAT) (Marques et al., 2015).

2.2.12 Antihypertensive activity Hypertension has become one of the most prevalent health issues in 21st century. Longterm high blood pressure is a major risk factor for coronary artery disease, stroke, heart failure, and other cardiovascular diseases. Isochroman scaffold was reported to play a virtual role in the development of antihypertensive agents, the progress was closely related

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to a great deal of work by Jinyi Xu group in this field. Isochroman-based precursor was modified with fragments inspired from marketed drugs no matter on the benzene ring or tetrahydropyran ring, and the inflammatory-related targets, b-adrenoceptor and a1adrenergic receptor are the main targets involved into the antihypertensive effects of isochroman analoges. It can also be regarded a good story from promising lead compound in natural product to synthetic clinical candidate with the help of fragment-based drug design and chemical synthesis (Zhao et al., 2021).

2.2.13 Antitumor activity Isochromans were considered as the potential antitumor scaffolds. A series of isochromans from Aspergillus ustus and Penicillium was isolated and their derivatives were prepared with chemical modification. Among them (þ)-pseudodeflectusin, showed as the strongest antitumor activity against HCT116 human colon cancer cells, Analoges (þ)-ustusoranes C were the other active compounds, and the IC50 values were 5.9 and 9.8 mM, respectively. The SAR studies indicated that the enone of the furanone moiety was essential for the cytotoxicity. A novel isochroman derivative penicitrinol, was isolated from the metabolites of marine-source fungus Penicillium citrinum with modest cytotoxic activity against HL60 cell line (IC50: 22.7 mg/mL), meanwhile, the constituent pennicitrinone A with rigid plane and higher molecular weight showed weak inhibitory effect. Isochromans from Penicillium exhibited antitumor potential antitumor activity. In vitro, compounds 55e60 (10 mg/mL) suppressed the growth of L5178Y cell line with the inhibition of 26.2, 16.1, 13.7, 3.4, 40.4, and 59.5, respectively. It can be seen from the result that methyl group on the C-5 position of the benzene ring was necessary for the activity. The antitumor activity of 1,3-benzodioxole derivatives, was synthesized and evaluated among which the isochroman analoges 61 and 62 exhibited moderate activity, while the ring opening compound 63 showed the strongest antitumor effect against the lung cancer cells NCIeH460 with the growth percentage for 67%, 86%, and 4% at the dosage of 100 mM, respectively (Zhao et al., 2021).

2.3 Conclusion Biological activity is the ability of a particular molecular entity to bring about a specific biological change on the target whose biological effect is to be effected. The effectiveness and concentration of the biological activity needed to impact the effect is measured in several ways. The biological activity can be studied either in vivo or in vitro. There are many types of biological activities e.g. antimicrobial, antifungal, antioxidant, antitumor, anticancer, antimalarial, anti-tuberculosis, anti-inflammatory, anti-aging, anti-proliferative, hypoglycemic, hypocholesterolemic, antihypertensive activities. The evaluation of biological activity requires test systems that are present in the body of the organism in order to obtain signals measured by spectrophotometry, or photometry, in parallel experiments of different concentrations of the samples to be tested and then compared with the control samples.

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C H A P T E R

3 Biological activities and therapeutic effects of Celastrus paniculatus seed oil Kim Wei Chan1, Voon Kin Chin2, Norsharina Ismail1, Der Jiun Ooi3, Nicholas M.H. Khong4 and Norhaizan Mohd Esa1,5 1

Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 2Department of Medical Microbiology, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 3 Department of Oral Biology and Biomedical Sciences, Faculty of Dentistry, MAHSA University, Jenjarom, Selangor, Malaysia 4School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor, Malaysia 5Department of Nutrition, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

Abbreviations AChE ALP ALT AST CAT CE CO CP CPSO DPPH EPM ESR FRAP GABAB GPx GR

acetylcholinesterase alkaline phosphatase alanine transaminase aspartate transaminase catalase chloroform extract Celastrus oil Celastrus paniculatus Willd Celastrus paniculatus seed oil 1,1-diphenyl-2-picrylhydrazyl elevated plus maze erythrocyte sedimentation rate ferric reducing antioxidant power assay G-protein coupled receptors for gamma-aminobutyric acid glutathione peroxidase glutathione reductase

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00024-6

29

© 2022 Elsevier Inc. All rights reserved.

30 GST H2O2 IL-10 IL-6 JO LPO MDA MOA-A MSG NO PCP PEE RAM RSA SGOT SGPT SOD TEAC TNF-α WBC

3. Biological activities and therapeutic effects of Celastrus paniculatus seed oil

glutathione S-transferase hydrogen peroxide interleukin-10 interleukin-6 Jyothismati oil lipid peroxides malondialdehyde monoamine oxidase-A monosodium glutamate nitric oxide petroleum ether fraction petroleum ether extract radial arm maze radical scavenging activity serum glutamyloxalacetic acid transaminase serum glutamyl pyruvate transaminase superoxide dismutase trolox equivalent antioxidant capacity tumor necrosis factor-alpha white blood cell

3.1 Botanical description, geographical distribution and traditional medicinal uses of Celastrus paniculatus Celastrus paniculatus Willd (CP), commonly known as the climbing staff tree, black oil plant or intellect tree, is a large deciduous climbing shrub, which may grow up to 18 m in height. CP is a native plant of the Indian continent and vernacularly known as “Malkangni” in Hindi or “Jyotishmati” in Sanskrit languages. Besides India, CP is geographically distributed across China, Australia, Sri Lanka, Nepal, Southeast Asia (Indonesia, Thailand, Laos, Vietnam, Cambodia, Malaysia, and Myanmar), Africa, and Pacific islands (Arora & Rai, 2012). As a member of the Celastraceae family, CP plant produces numerous woody branches that cling to the surrounding vegetation for support. The bark of the plant is pale or reddish brown in color and has a rough and exfoliating texture; while its light to dark green serrated leaves are oval/obovate/elliptic in shape, leathery and smooth in texture, and arranged alternately on the short petioles. The CP flowers are tiny (B3.8 mm in diameter) and whitish to yellowish green in color (Fig. 3.1A); whereas the fruits are tri-lobed, globose and yellow colored (Fig. 3.1B). Each CP capsule contains 3
6 seeds, which are closely enveloped with a layer of orange-red aril (Fig. 3.1C). The seed are small, oval in shape, reddish brown in color, and rich in seed oil with a distinctive aroma and intense reddishyellow color (Akbar, 2020; Arora & Rai, 2012). CP is extensively used in the traditional medicinal practices of Ayurveda and Unani (Akbar, 2020). In Ayurvedic medicine, CP seeds are categorized as the “nervine tonic” (Medhya Rasayana) with potent memory sharpening and intellectual powers stimulating properties. CP seeds are therapeutically used for the treatments of nervous system disorders (va˜tavya˜dhi), memory weakness (smrtidaurbalya) and eucoderma/vitiligo (´svitra). On the other hand, Unani medicine practitioners regard CP seed as a medicinal ingredient

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3.2 Chemical composition of Celastrus paniculatus seed oil

FIGURE 3.1 Celastrus (A)

(B)

paniculatus flowers (A), fruits (B), and seeds (C). Source: https://commons. wikimedia.org.

(C)

with carminative, phlegm-expelling, stimulating and aphrodisiac properties. Therefore, CP seeds can be used externally and internally, for the treatments of rheumatoid arthritis, gout, leprosy, paralysis, palsy, dementia, and epilepsy, as well as to improve memory, intellect, stomach functions and sexual performance.

3.2 Chemical composition of Celastrus paniculatus seed oil CP mature seed is an abundant source of lipids with multiple therapeutic properties. Extraction of the CP seeds with nonpolar solvents, that is, n-hexane and petroleum ether, yielded up to 45.5%
52% (w/w) of lipids (Ramadan et al., 2009; Rana & Das, 2017; Sengupta & Bhargava, 1970); while a lower yield (25%) was recorded with the traditional oil extraction method, practiced by the “Uraanv” community in India (Sahu et al., 2020). The lipid classes and their subclasses of n-hexane extracted CPSO were analyzed by using column and thin layer chromatographic techniques (Ramadan et al., 2009). Neutral lipids, which were comprised of triacylglycerol, free fatty acids, diacylglycerol, esterified sterols, and monoacylglycerol, in a descending order of abundance, were found to be the major lipid class (B99%) of CPSO. On the contrary, glycolipids (subclasses: sulphoquinovosyldiacylglycerol, digalactosyldiglycerides, cerebrosides, sterylglycosides, monogalactosyldiglyceridesand esterified sterylglycosides), and phospholipids (subclasses: phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine) were the minor lipid classes in CPSO, respectively, accounting for 0.55% and 0.34% of the total lipids.

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3. Biological activities and therapeutic effects of Celastrus paniculatus seed oil

TABLE 3.1 Fatty acids compositions of Celastrus paniculatus seed oil, as reported by different studies. Relative content (%)

Fatty acids Rana and Das (2017)a Saturated

Ramadan et al. (2009)

Sengupta and Bhargava (1970)a

26.98

29.25

36.52

Myristic acid, C14:0

0.65

0.40

Palmitic acid, C16:0

20.83

26.10

32.84

Stearic acid, C18:0

4.35

2.75

3.68

Arachidic acid, C20:0

0.42

Lignoceric acid, C24:0

0.73

Unsaturated

73.02

70.75

63.48

Oleic acid, C18:1

56.68

54.20

23.69

Linoleic acid, C18:2

16.15

11.20

16.53

5.35

23.26

100.00

100.00

α-Linolenic acid, C18:3 (n-3)/ Linolenic acid, C18:3 Gondoic acid, 20:1 (n-9) Total a

0.19 100.00

Values recalculated based on the total fatty acids detected.

Table 3.1 shows the fatty acid compositions of CPSO that were reported by different studies. In general, CPSO was rich unsaturated fatty acids, accounting for approximately 64%
73% of total fatty acids detected. In the early study, CPSO was found to be consisted of five fatty acids, with palmitic acid as the predominant fatty acid (32.8%), followed by oleic, linolenic, linoleic, and stearic acids (Sengupta & Bhargava, 1970). However, in the more recent studies, oleic acid was then found to be the most abundant fatty acid (54.2%
56.7%) in CPSO, followed by palmitic acid (20.8%
26.1%) and linoleic acid (11.2% 2 16.2%); while other minor fatty acids (,10%) detected were stearic, α-linolenic, myristic, arachidic, lignoceric, and gondoic acids (Ramadan et al., 2009; Rana & Das, 2017). Dietary consumption of oleic acid, the major monounsaturated omega-9 fatty acid in olive oil, has been widely reported to confer health-beneficial effects against various metabolic disorders and inflammatory diseases, such as cardiovascular diseases, cancers, diabetes, and autoimmune diseases (Rehman et al., 2020; Sales-Campos et al., 2013). The discrepancy in fatty acid compositions of CPSO between studies might be contributed by the geographical factors (e.g., climate) (Rana & Das, 2017) and analytical techniques. Phytosterols are naturally occurring bioactive in the plant-based edible oils (e.g.,cereal, fruits and vegetable oils) that possess numerous therapeutic properties, particularly against lipid metabolic disorders and cancers (Moreau et al., 2018; Woyengo et al., 2009). Gas chromatography analysis showed that nearly half of the CPSO unsaponifiable matters

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(1.6% of total lipids) were consisted of phytosterols. Beta (β)-sitosterol, campesterol, and stigmasterol (55.7%, 18.9%, and 16.4% of total sterols, respectively) were the major phytosterols detected in CPSO; while the levels of Δ7-avenasterol, Δ5-avenasterol, and Δ7-stigmastenol were relatively lower in the oil (Ramadan et al., 2009). Besides phytosterols, plant-based edible oils are also the natural dietary reservoirs for tocopherols. Tocopherols are nutritionally important micronutrient and powerful lipophilic antioxidants that play vital roles in improving the human health (e.g., prevention of cardiovascular diseases and cancers) and food quality (e.g., inhibition of food lipid oxidation/ rancidity) (Shahidi & De Camargo, 2016). Out of the four tocopherol isomers, α- and γ-tocopherols were detected in CPSO via normal phase high-performance liquid chromatography analysis, respectively, at the level of 52 and 104 mg/ 100 g total lipids (Ramadan et al., 2009). In comparison to the tocopherol contents of some common edible oils (e.g., sunflower seed, palm, soybean, corn, olive, etc.), CPSO can be considered as a rich dietary source of α- and γ-tocopherols (Shahidi & De Camargo, 2016). Apart from phytosterols and tocopherols, CPSO was found to contain some aromatic compounds, such as 1,4-benzenediol, butylated hydroxytoluene, benzoic acid, cinnamic acid, eudalene, and 2,6-di-tert-butylp-benzoquinone, which may contribute to the distinctive aroma of CPSO (Rana & Das, 2017). Preliminary phytochemical screening also indicated the presence of saponins, terpenoids, alkaloids, tannins, flavonoids. and steroids in CPSO (Maurya & Dwivedi, 2020). Application of hydro-distillation process on ground CP seeds produced a dark browncolored essential oil, with the extraction yield of 0.09% (w/w). The gas chromatographymass spectrometry analysis revealed the presence of 56 compounds in the CP essential oil, which primarily consisted of bicyclic sesquiterpenes, tricyclics sesquiterpenes, terpene alcohols, fatty acids, ketones, esters, as well as other terpene related compounds, such as flavonoids and alkaloids (Arora & Pandey-Rai, 2014). Specifically, palmitic acid, phytol, erucic acid, trans-beta-copaene, linalool, γ-muurolene, cubenol, valeric acid,3-pentadecyl ester, phytone and palmitaldehyde, diallylacetal were the top 10 identified compounds in the tested essential oil, with a descending peak area percentage of 38.6%, 11.7%, 7.0%, 4.8%, 4.0%, 2.5%, 2.4%, 2.3%, 2.1%, and 1.8%, respectively.

3.3 Biological activities and therapeutic effects of Celastrus paniculatus seed oil CP is amongst the medicinal plants that have been well-recognized for its therapeutic potentials and applications involving neurological disorders, cognitive impairment, and acts as a brain tonic (Russo, et al., 2001). The CP seed exhibits a broad array of therapeutic potentials. The seed oil extracted from this plant has shown its huge pharmacological implications and therapeutic efficacy in treating various diseases and disorders, such as brain-associated disorders and neurological impairments, oxidative stress, systemic inflammation, arthritis, gastric ulcers and so on. Besides, CP also possesses many beneficial medicinal properties, such as enhancement of learning and memory events, wound healing and other unknown medicinal benefits, which remain to cultivate (Arora & Pandey-Rai, 2014; Bhagya et al., 2016; Gattu et al., 1997; Kumar & Gupta, 2002; Maurya & Dwivedi, 2020; Palle et al., 2018; Ramadan et al., 2009; Ramaiah et al., 2018; Ruksiriwanich et al., 2014; Salomi et al., 2011; Shah

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3. Biological activities and therapeutic effects of Celastrus paniculatus seed oil

et al., 2018; Valecha & Dhingra, 2014). The complete description of the biological activities and therapeutic effects of CPSO is illustrated in each of the following subsections.

3.3.1 Neuroprotective properties Celastrus paniculatus seed oil (CPSO) has shown its remarkable neuroprotection against a number of brain and neurological disorders, improvement in cognitive perturbations and functionality of nervous system and increases the learning and memory performance. One of the prominent therapeutic benefits that underlie CPSO is the antidepressive effect. For instance, Valecha and Dhingra (2014) had demonstrated that CPSO possessed antidepressant-like activity in Swiss young albino mice that experienced chronic unpredictable mild stress. The authors reported that the antidepressant-like activity of CPSO in both chronic unpredictable mild stressed and unstressed mice could be probably attributed by the suppression of monoamine oxidase-A (MAO-A) activity, scavenge of free radicals, as well as via reduction of plasma nitrite levels (Valecha & Dhingra, 2014). It has been found that the high MAO-A activity in the brain heightened the level of depression and subsequently causes a reduction in the levels of monoamines (Meyer et al., 2006). Further, the authors also showed that reduced plasma corticosterone levels might contribute to the antidepressant-like activity in stressed mice (Valecha & Dhingra, 2014). Similarly, in another study, Wani et al. (2015) showed that the petroleum ether extract (PEE) of CP seed possessed antidepressant activity, in both experimental rat and mice models (Wani et al., 2015). The authors observed that the administration of PEE had successfully reversed the reserpine-induced immobility extension, as well as reduced the immobility period in mice, as evidenced by the tail suspension and forced swimming tests. Furthermore, in this study, PEE supplementation also reversed the degree of reserpine-stimulated catalepsy and ptosis in ratsin a dose-dependent manner. Nevertheless, the active compounds and their associated mechanisms that responsible for the observed antidepressant effects remain unclear (Wani et al., 2015). Likewise, Valecha and Dhingra (2016) also illustrated the antidepressantlike activity of CPSO in unstressed mice and investigated the underlying mechanisms that may contribute to such activity. The authors showed that CPSO markedly shortened the immobility period of mice and its therapeutic efficacy was comparable to fluoxetine. However, supplementation of CPSO did not produce any significant impact on the mice’ locomotor activity. Moreover, the authors revealed that the observed antidepressant-like effects in CPSO-supplemented mice could be possibly due to the interactions of CPSO with serotonergic, dopamine D2 and G-protein coupled receptors for gamma-aminobutyric acid (GABAB) receptors, accompanied with the suppression of MAO-A activity and reduced levels of plasma corticosterone (Valecha & Dhingra, 2016). Aside from its antidepressant activity, CPSO has been reported in some early studies for its antisedative, tranquilizing and antispasmodic effects against the excitement and toxicity induced by amphetamine in experimental mice models (Gatinode et al., 1957; Sheth et al., 1963; Shroff et al., 1959). Furthermore, CPSO has been found to exert anxiolytic activity. The Celastrus oil (CO), derived from the PEE of CP seed, tested at the dosages of 1 and 1.5 g/kg, showed significant anxiolytic activity in rats without sedation effect and tolerance production. Pretreatment with CO in rats for 14 days had reversed the anxiolytic effect induced by

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buspirone in an open field test. The nonsedative effect and reversal of anxiety behavior induced by buspirone suggested that the anxiolytic potential of CO may be related to the serotonergic mechanism. However, further studies are required to uncover the precise underlying mechanism of action (Rajkumar et al., 2007). Lekha et al. (2010) had studied the stress relieving effect of Jyothismati oil (JO) extract, isolated from CP seed, against both chronic and acute immobilization-induced stress in albino mice. The authors reported that the immobilization stress, triggered by both acute and chronic immobilization, decreased the levels of antioxidant enzymes, that is, catalase (CAT), lipid peroxides (LPO), glutathione S-transferase (GST), glutathione reductase (GR), glutathione peroxidase (GPx), and superoxide dismutase (SOD). A higher reduction in antioxidant enzymes was observed in the chronic immobilization group. Upon treatment with JO, the levels of the aforementioned antioxidant enzymes were significantly increased in both acute and chronic immobilization groups, suggesting that the high antioxidant properties in JO may effectively alleviate the stress induced by hours of physical immobilization (Lekha et al., 2010). On the other hand, the neuroprotective effect of CPSO against the hydrogen peroxide (H2O2) and glutamate-induced neurotoxicity in embryonic rat forebrain neuronal cells (FBNC) has been demonstrated. Neuronal cells pretreated with CPSO had successfully alleviated both H2O2- and glutamate-induced neuronal death in a dose-dependent manner. In addition, pretreatment with CPSO decreased the level of malondialdehyde (MDA), increased the cellular catalase activity and did not affect the cellular acetylcholinesterase (AChE) activity. Hence, the neuroprotection conferred by CPSO was speculated to be mediated by the its antioxidant activity (Godkar et al., 2006). Similarly, the neuroprotection of CPSO against free radical-induced neuronal impairment has been documented. In order to investigate the role of CPSO against oxidative stress in neuronal cells, Shah et al. (2018) employed monosodium glutamate (MSG), a potent inducer of free radicals, on the human IMR-32 neuroblastoma cells. The study revealed that CPSO treatment mitigated the levels of lipid peroxidation and protein carbonyl in the cells, accompanied with an augmentation in the cellular CAT and SOD activities. The study also showed that CPSO enhanced the free radical scavenging capacity of the cells by increasing their glutathione level, as well as facilitating the regeneration of glutathione by restoring the activities of GR, GST and GPx. Therefore, it is postulated that the antioxidant property of CPSO plays a pivotal role in ameliorating the neuronal impairment induced by free radicals (Shah et al., 2018). The CPSO has been reported to have profound effects in intellect stimulation and memory enhancement. Nalini and colleagues (1986) showed that significant improvement in the I.Q. scores, accompanied with reduced urine levels of catecholamine metabolites, homovanillic acid and vanilylmandelic acid were recorded in mentally retarded children receiving chronic CPSO therapy (Nalini et al., 1986). Another study had evaluated the cognitive effect of CPSO on learning and memory in a passive avoidance model (two compartment passive avoidance task) in albino rats. Additionally, the changes in the neurotransmitter levels corresponding to the cognitive effect of CPSO were also investigated. Findings from the study revealed that the retention ability of albino rats was significantly improved following the oral supplementation of CPSO. The notable improvement may be associated with the significant reduction in the noradrenaline, serotonin (5-hydroxytryptamine) and dopamine levels in the brain, suggesting the involvement of these a minergic systems in the memory and learning event (Nalini et al., 1995).

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3. Biological activities and therapeutic effects of Celastrus paniculatus seed oil

Gattu et al. (1997) had investigated the effects of CPSO on the navigational memory performance in scopolamine-induced deficits young adult rats (Gattu et al., 1997). The study showed that chronic treatment with CPSO in rats had selectively reversed the disruption in spatial memory caused by acute central muscarinic receptor blockade, indicating that one or more CPSO constituents may exhibit cognitive enhancing properties. With the exclusion of anticholinesterase-like action, the underlying mechanism that contributed to the reversal of scopolamine’s mnemonic effects by CPSO treatment remains elusive and requires further study (Gattu et al., 1997). A more recent study by Bhagya et al. (2016) had probed the neuroprotective effects of CPSO on stress-induced cognitive impairments in the male Wistar rats. The authors reported that treatment with CPSO had significantly reduced anxiety-like behavior of the elevated plus maze (EPM) stressed rats. Moreover, CPSO therapy enhanced the spatial learning and memory capabilities in stressed rats, as evidenced by the improved performance in both T-maze and partially baited radial arm maze (RAM) (Bhagya et al., 2016). There are several lines of evidences that reveal the protective potentials of CPSO against dementia and other neurodegenerative diseases. Chakrabarty and co-workers (2012) performed the investigation on the protective effects of CPSO against oxidative stress and progressive neural damage, through a rat model of senile dementia, induced by the administration of aluminium chloride. The authors documented that treatment with CPSO significantly prevented the aluminum-induced neural damage and systemic oxidative stress, as assessed by neural behavioral, histological and biochemical analyses. The authors postulated that CPSO is a novel natural source that possesses the antidementic properties and capable to hinder the pathobiological progression of Alzheimer’s disease (Chakrabarty et al., 2012).

3.3.2 Antifertility properties The antifertility effect of CPSO on the reproductive system has been previously reported. In an early study, it has been found that the testes of rats treated with oily extract of CP seed showed vacuolization, arrest of spermatogenesis and germ cell depletion. Thus, it is suggesting that CPSO may possess antifertility effect on the male reproductive system (Bidwai et al., 1990).

3.3.3 Antioxidant, anti-inflammatory and anti-arthritic properties The radical scavenging activity (RSA) of CPSO and extra virgin olive oil towards 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were compared in a study by Ramadan et al. (2009). The study reported that CPSO exhibited more robust RSA in comparison to the extra virgin olive oil; In which, 24% DPPH radicals were quenched by CPSO after an hour of incubation, as compared to only 9.4% DPPH radicals were quenched by extra virgin olive oil. The high antiradical activity exerted by CPSO compared to extra virgin olive oil could be attributed by a few factors, which may include the difference in the composition and content of polar lipids and unsaponifiable matters, the synergistic effect between polar lipids with other antioxidative molecules, the diversity in the structural features of the potential phenolic antioxidants and the kinetic behaviors differences of potential antioxidants

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3.3 Biological activities and therapeutic effects of Celastrus paniculatus seed oil

37

In another source, the PEE of CP seed has been found to possess both immunomodulatory and antioxidant properties in immune-suppressed rodent model induced by pyrogallol. The source claimed that PEE triggered the elicitation of humoral immune response marked by an elevation in the antibody titer. On the other hand, the stimulation of cellmediated immunity was observed by the increase in the mean percentage of paw volume, the percentage of phagocytosis, as well as higher white blood cells count. In addition, the antioxidant property of PEE of CP seed was also demonstrated in this study, as evidenced by the rise of catalase, reduced glutathione and superoxide dismutase, accompanied with the reduction lipid peroxidation. (Salomi et al., 2011). Another study had reported that chloroform extract (CE) of CP seed contained the highest level of phenolic compounds and exhibited strongest antioxidative effects in experimental assays with different mechanisms, that is, DPPH free RSA, ferric reducing antioxidant power (FRAP), lipoxygenase inhibition and trolox equivalent antioxidant capacity (TEAC) assays. (Arora & Pandey-Rai, 2014). The anti-arthritic and anti-inflammatory effects of CPSO had been evaluated in an in vivo study. The study reported that treatment with the PEE of CP seed had significantly reduced the paw swelling volume by 56.6%, suggesting the anti-arthritic effect of CP seed. Further, it had been observed that the body weight of rats receiving PEE was significantly higher as compared to the arthritic control group, which could be correlated to the antiinflammatory potential of CP seed. Also, the expression of serum glutamyloxal acetic acid transaminase (SGOT) and serum glutamyl pyruvate transaminase (SGPT) were found to be were significantly reduced in animals treated with PEE of CP seed in comparison to arthritic group. This suggests that treatment with CP seed PEE might exhibit both antiarthritic and anti-inflammatory activities. Nevertheless, further studies are needed to untangle the bioactive compounds that contributed to these activities (Suryawanshi et al., 2008). Different studies also reported the in vivo anti-arthritic activity of CPSO. In one study, the anti-arthritic effect of ethanolic (EE) and PEE extracts of CP seed on Freund’s adjuvant arthritis has been assessed in Wistar albino rats. It had been shown that the body weight of rats, which was supposed to be reduced under the arthritic condition, had been corrected after the oral administration with both EE and PEE of CP seed. The swollen paw developed during the secondary lesions was also greatly reduced. The EE and PEE dosages attribute to this therapeutic effect were 300 mg/kg and 500 mg/kg body weight, respectively. Further, the study also showed that the white blood cell (WBC) count as well as erythrocyte sedimentation rate (ESR) in arthritic rats had markedly reduced upon treatment with CPSO extracts (Patil & Suryavanshi, 2007). Kothavade et al. (2015) also demonstrated that the anti-arthritic effect of the petroleum ether fraction (PCP) of CP seed in an adjuvant-induced arthritis in rat model (Kothavade et al., 2015). The authors depicted that PCP had significantly mitigated the progression of arthritis in rats, as exemplified by a few parameters, that is, the severity of paw swelling, immune organs indices, arthritic score, body weight and hyperalgesic effect. Such observations were explainable by the significant down-regulation of the overwhelming inflammatory cytokines production [i.e., tumor necrosis factor-alpha (TNF-α) and interleukin-6 (IL-6)], as well as the reduction in the levels of cellular enzymes [i.e. aspartate transaminase (AST), alanine transaminase (ALT) and alkaline phosphatase (ALP)] and oxidative stress markers [i.e.,

Multiple Biological Activities of Unconventional Seed Oils

38

3. Biological activities and therapeutic effects of Celastrus paniculatus seed oil

malondialdehyde (MDA) and nitric oxide (NO)], as compared to the non-treated arthritic rats. Overall, the authors deduced that the anti-arthritic effects of PCP could be attributed by the cytokine regulation, immunosuppressive effects, bone protective activities and antioxidant effects (Kothavade et al., 2015).

3.3.4 Cosmeceutical and wound healing properties The cosmeceutical application of CPSO has been previously elucidated. In one study, CPSO was encapsulated in the 2-hydroxypropyl-β-cyclodextrin (HPβCD) cavities and its physiochemical stability, biological activities as well as skin penetration properties. Results from the study showed that CPSO-HPβCD inclusion complex exhibited antioxidant and tyrosinase inhibitory activities. Although its magnitudes were lower than CPSO without encapsulation, it was deduced that encapsulated CPSO may exhibit sustainable slowrelease action of the CPSO active compounds advantageously (Ruksiriwanich et al., 2018). In addition, the greater extent of tyrosinase inhibitory activities exhibited by CPSO as compared to tested whitening agents, that is, ascorbic acid, kojic acid and arbutin, is worthmentioning (Ruksiriwanich et al., 2018; Ruksiriwanich et al., 2014). Apart from this, skin penetration assay revealed that serum formulation containing CPSO-HPβCD complex had the highest cumulative number of oleic acid in the whole skin (32.75 6 1.25 μg/cm2) and the flux through receptor fluid (1.02 6 0.15 μg/cm2/h), in contrast with CPSO oily formulation, after 6 hours of topical application. This suggests that CPSO-HPβCD formulation penetrated through the skin more efficiently than CPSO oily formulation and exhibited proper viscosity (Ruksiriwanich et al., 2018). In the nutshells, it is implied that CPSO, with or without encapsulation, is a promising candidate for cosmeticeutical products development, in particularly related to skin whitening and anti-aging effects (Ruksiriwanich et al., 2018; Ruksiriwanich et al., 2014). On the other side, the approach of using CPSO as a wound healing agent has been described in an experimental rat model. In this study, CPSO was prepared into 5% and 10% (w/w) gel-based formulation, and tested against burn and excision wounds in the rats. It has been reported that CPSO 5% and 10% gels posed significant wound healing activity, as measured the percentage of wound contraction and duration of epithelization, as compared to the disease and standard controls. In addition, both CPSO 5% and 10% gels shown relatively high wound contraction rate in both wound models in comparison to the disease controls. Also, histological analysis revealed that the skin of the wound region treated by CPSO gels was surrounded by collagen fibers, fibroblast cells and new blood vessels, as compared to the disease control. Hence, the authors surmized that CPSO 5% gel exhibited remarkable wound healing capacity than the standard wound healing drugs (Maurya & Dwivedi, 2020).

3.3.5 Gastroprotective properties The gastroprotective and antiulcer effects of CPSO have been illustrated in different gastric ulcer models in rats. It has been reported CPSO with the dosages of 200 and 400 mg/kg showed effective gastroprotection against indomethacin- and ethanol-induced

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3.4 Toxicological assessment of Celastrus paniculatus seed oil

39

ulcer models. Such effect could be partly caused by the suppression of pro-inflammatory cytokines (IL-6 and TNF-α) and increased expression of interleukin-10 (IL-10). Apart from this, CPSO conferred gastroprotection in pylorus-ligated rats through the reduction in the gastric acidity and total gastric juice volume while increasing the gastric pH, suggesting the antisecretory effects of CPSO. Also, CPSO was shown to reduce the gastric emptying rate. However, CPSO did not exert any effect on gastric transit. This indicates that the suppressive effect on hypermotility could explain the antiulcerogenic action of CPSO. Additionally, significant reduction in MDA (malondialdehyde) levels, followed by the enhancement of catalase and SOD activities, had been observed in the ethanol-induced ulcer rats receiving CPSO. The study highlighted that the gastroprotective effect of CPSO could be due to its antioxidant activity (Palle et al., 2018).

3.4 Toxicological assessment of Celastrus paniculatus seed oil Herbal plants are undoubtedly one of the natural resources that can be potentially applied for clinical therapies upon extensive scientific studies. However, the safety of herbal plants in the therapeutic applications remains a major concern due to their potentially unknown toxicity to human (Sharwan et al., 2015). Therefore, it is essential to conduct a series of detailed toxicity assessments on newly discovered herbal plants or developed drugs, in order to ensure the absence of toxicity and associated adverse effects in human prior to their clinical use. Although the therapeutic benefits of CPSO has been reported by a plethora of preclinical studies, studies related to the toxicity and safety profile of CPSO are in paucity. An older study showed that CPSO could produce undesirable effect on the liver of adult rats, exemplified by the development of focal necrosis in the liver of adult rats treated with 0.2 mL CPSO intraperitoneal every other day for 30 days, however, the degeneration effect is reversible with time whereby these developed lesions were disappeared after 45 days posttreatment with CPSO (Bidwai et al., 1990). In another study, Nalini et al. (1995) had performed acute and neuronal toxicity studies of CPSO administered at different dosages (0.5
5 g/kg body weight) orally through observation on the gross behavioral changes in rats for acute toxicity study and rotarod test for neurotoxicity study. The study showed that CPSO tested at all different dose levels neither cause any significant toxicity on the normal behavioral changes in rats nor disruption in motor coordination (Nalini et al., 1995). In a recently published study, Mishra et al. (2020) performed a toxicity evaluation (acute and subacute toxicity studies) on CPSO according to the Organization for Economic Cooperation and Development Guidelines No. 423, using Swiss albino mice, The authors provided a safety description on CPSO based on the observation of several parameters, which involved autonomic, behavioral, biochemical, physical and neurological profiles (Mishra et al., 2020). The authors documented normal health conditions of mice receiving oral administration of CPSO, in both acute and subacute toxicity studies. Thus, it is suggested that CP is generally considered to be nontoxic. Further, the authors deduced that the toxicity profile of CPSO was safe up to the dosage level of 2000 mg/kg.

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3. Biological activities and therapeutic effects of Celastrus paniculatus seed oil

References Akbar, S. (2020). Celastrus paniculatus Willd. (Celastraceae). Handbook of 200 medicinal plants (pp. 561
567). Springer. Arora, N., & Pandey-Rai, S. (2014). GC
MS analysis of the essential oil of Celastrus paniculatus Willd. seeds and antioxidant, anti-inflammatory study of its various solvent extracts. Industrial Crops and Products, 61, 345
351. Arora, N., & Rai, S. P. (2012). Celastrus paniculatus, an endangered Indian medicinal plant with miraculous cognitive and other therapeutic properties: An overview. International Journal of Pharma and Bio Sciences, 3(3), 290
303. Bhagya, V., Christofer, T., & Rao, B. S. (2016). Neuroprotective effect of Celastrus paniculatus on chronic stressinduced cognitive impairment. Indian Journal of Pharmacology, 48(6), 687. Bidwai, P., Wangoo, D., & Bhullar, N. (1990). Antispermatogenic action of Celastrus paniculatus seed extract in the rat with reversible changes in the liver. Journal of Ethnopharmacology, 28(3), 293
303. Chakrabarty, M., Bhat, P., Kumari, S., D’Souza, A., Bairy, K., Chaturvedi, A., . . . Kamath, S. (2012). Corticohippocampal salvage in chronic aluminium induced neurodegeneration by Celastrus paniculatus seed oil: Neurobehavioural, biochemical, histological study. Journal of Pharmacology and Pharmacotherapeutics, 3(2), 161
171. Gatinode, B., Raiker, K., Shroff, F., & Patel, J. (1957). Pharmacological studies with malkanguni, an indigenous tranquilizing drug (preliminary report). Current Practice, 1, 619
621. Gattu, M., Boss, K. L., Terry JR., A.V.., & Buccafusco, J. J. (1997). Reversal of scopolamine-induced deficits in navigational memory performance by the seed oil of Celastrus paniculatus. Pharmacology, Biochemistry, and Behavior, 57(4), 793
799. Godkar, P., Gordon, R., Ravindran, A., & Doctor, B. (2006). Celastrus paniculatus seed oil and organic extracts attenuate hydrogen peroxide- and glutamate-induced injury in embryonic rat forebrain neuronal cells. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 13(1
2), 29
36. Kothavade, P. S., Bulani, V. D., Deshpande, P. S., Chowdhury, A. S., & Juvekar, A. R. (2015). The petroleum ether fraction of Celastrus paniculatus Willd seeds demonstrates anti-arthritic effect in adjuvant-induced arthritis in rats. Journal of Traditional Chinese Medical Sciences, 2(3), 183
193. Kumar, M., & Gupta, Y. (2002). Antioxidant property of Celastrus paniculatus Willd.: A possible mechanism in enhancing cognition. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 9(4), 302
311. Lekha, G., Mohan, K., & Samy, I. A. (2010). Effect of Celastrus paniculatus seed oil (Jyothismati oil) on acute and chronic immobilization stress induced in swiss albino mice. Pharmacognosy Research, 2(3), 169. Maurya, H., & Dwivedi, V. (2020). Wound healing potential of Celastrus paniculatus seed oil in rat model. International Research Journal of Pharmacology, 2(1), 1
8. Meyer, J. H., Ginovart, N., Boovariwala, A., Sagrati, S., Hussey, D., Garcia, A., . . . Houle, S. (2006). Elevated monoamine oxidase a levels in the brain: An explanation for the monoamine imbalance of major depression. Archives of General Psychiatry, 63(11), 1209
1216. Mishra, B., John, E., Joy, K., Badmanaban, R., & Aleesha, R. (2020). Toxicity profile of Celastrus paniculatus seeds: A preclinical study. Asian Journal of Pharmaceutical and Clinical Research, 13(7), 115
118. Moreau, R. A., Nystro¨m, L., Whitaker, B. D., Winkler-Moser, J. K., Baer, D. J., Gebauer, S. K., & Hicks, K. B. (2018). Phytosterols and their derivatives: Structural diversity, distribution, metabolism, analysis, and healthpromoting uses. Progress in Lipid Research, 70, 35
61. Nalini, K., Aroor, A., Kumar, K., & Rao, A. (1986). Studies on biogenic amines and their metabolites in mentally retarded children on Celastrus oil therapy. Alternative medicine, 1(4), 355
360. Nalini, K., Karanth, K., Rao, A., & Aroor, A. (1995). Effects of Celastrus paniculatus on passive avoidance performance and biogenic amine turnover in albino rats. Journal of Ethnopharmacology, 47(2), 101
108. Palle, S., Kanakalatha, A., & Kavitha, C. N. (2018). Gastroprotective and antiulcer effects of Celastrus paniculatus seed oil against several gastric ulcer models in rats. Journal of Dietary Supplements, 15(4), 373
385. Patil, K. S., & Suryavanshi, J. (2007). Effect of Celastrus paniculatus Willd. seed on adjuvant induced arthritis in rats. Pharmacognosy Magazine, 3(11), 177. Rajkumar, R., Kumar, E. P., Sudha, S., & Suresh, B. (2007). Evaluation of anxiolytic potential of Celastrus oil in rat models of behaviour. Fitoterapia, 78(2), 120
124. Ramadan, M. F., Kinni, S., Rajanna, L., Seetharam, Y., Seshagiri, M., & Mo¨rsel, J.-T. (2009). Fatty acids, bioactive lipids and radical scavenging activity of Celastrus paniculatus Willd. seed oil. Scientia Horticulturae, 123(1), 104
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Ramaiah, C. V., Kumar, G. S., & Rajendra, W. (2018). Traditional, Ethnomedical, and Pharmacological uses of Celastrus paniculatus. Asian Journal of Pharmaceutics, 12, 1119
1126. Rana, V. S., & Das, M. (2017). Fatty acid and non-fatty acid components of the seed oil of Celastrus paniculatus willd. International Journal of Fruit Science, 17(4), 407
414. Rehman, K., Haider, K., Jabeen, K., & Akash, M. S. H. (2020). Current perspectives of oleic acid: Regulation of molecular pathways in mitochondrial and endothelial functioning against insulin resistance and diabetes. Reviews in Endocrine and Metabolic Disorders, 21(4), 631
643. Ruksiriwanich, W., Sirithunyalug, J., Khantham, C., Leksomboon, K., & Jantrawut, P. (2018). Skin penetration and stability enhancement of Celastrus paniculatus seed oil by 2-hydroxypropyl-β-cyclodextrin inclusion complex for cosmeceutical applications. Scientia Pharmaceutica, 86(3), 33. Ruksiriwanich, W., Sringarm, K., & Jantrawut, P. (2014). Stability enhancement of Celastrus paniculatus seed oil by loading in niosomes. Asian Journal of Pharmaceutical and Clinical Research, 7, 186
191. Russo, A., Izzo, A., Cardile, V., Borrelli, F., & Vanella, A. (2001). Indian medicinal plants as antiradicals and DNA cleavage protectors. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 8(2), 125
132. Sahu, L., Joshi, P. K., Rout, O. P., & Sahu, A. (2020). Phytochemical evaluation of Celastrus paniculatus seed oil extracted by a method used by “Uraanv” tribe of Chhattisgarh. Journal of Ayurveda and Integrated Medical Sciences, 5(2), 57
65. Sales-Campos, H., Reis de Souza, P., Crema Peghini, B., Santana da Silva, J., & Ribeiro Cardoso, C. (2013). An overview of the modulatory effects of oleic acid in health and disease. Mini Reviews in Medicinal Chemistry, 13(2), 201
210. Salomi, K. R., Shafeen, S. S., Roopesh, C., Reddy, Y. C., Sandya, L., Nagarjuna, S., & Reddy, Y. P. (2011). Evaluation of immunomodulatory activity of petroleum ether extract of seeds of Celastrus paniculatus. Der Pharmacia Letter, 3, 87
93. Sengupta, A., & Bhargava, H. (1970). Chemical investigation of the seed fat of Celastrus paniculatus. Journal of the Science of Food and Agriculture, 21(12), 628
631. Shah, N., Nariya, A., Pathan, A., Patel, A., Chettiar, S. S., & Jhala, D. (2018). Neuroprotection Effects of Celastrus paniculatus seed oil against monosodium glutamate in human IMR-32 cells. Annual Research & Review in Biology, 1
9. Shahidi, F., & De Camargo, A. C. (2016). Tocopherols and tocotrienols in common and emerging dietary sources: Occurrence, applications, and health benefits. International journal of molecular sciences, 17(10), 1745. Sharwan, G., Jain, P., Pandey, R., & Shukla, S. S. (2015). Toxicity profile of traditional herbal medicine. Journal of Ayurvedic and Herbal Medicine, 1(3), 81
90. Sheth, U. K., Vaz, A., Deliwala, C. V., & Bellare, R. A. (1963). Behavioural and pharmacological studies of a tranquilising fraction from the oil of Celastrus paniculatus (Malkanguni oil). Archives Internationales de Pharmacodynamie et de Therapie, 144, 34
50. Shroff, F., Gaitonde, B., & Patel, J. (1959). Tranquillizers (an experimental study). Journal of Hospital, 4, 160
173. Suryawanshi, J., Karande, K., Dias, R., & Patil, K. (2008). Formaldehyde induced antiarthritic activity of seeds of Celastrus paniculatus. Indian Journal of Natural Product, 24(2), 20
23. Valecha, R., & Dhingra, D. (2014). Antidepressant-like activity of Celastrus paniculatus seed oil in mice subjected to chronic unpredictable mild stress. Journal of Pharmaceutical Research International, 4(5), 576
593. Valecha, R., & Dhingra, D. (2016). Behavioral and biochemical evidences for antidepressant-like activity of Celastrus paniculatus seed oil in mice. Basic and Clinical Neuroscience, 7(1), 49. Wani, F. A., Iqbal, A., Jan, A., & Jafri, M. (2015). Antidepressant effect of petroleum ether extract of Malkangni (Celastrus paniculatus) in rats and mice. American Journal of Pharmacy and Pharmacology, 2, 9
12. Woyengo, T., Ramprasath, V., & Jones, P. (2009). Anticancer effects of phytosterols. European Journal of Clinical Nutrition, 63(7), 813
820.

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C H A P T E R

4 Biological activities of black cumin (Nigella sativa) seed oil Merve ¸Seyda Karac¸il Ermumcu Akdeniz University Faculty of Health Sciences, Nutrition and Dietetics, Antalya, Turkey

Abbreviations BMI BP CRP DBP DNA FBS g HbA1c HDL Hg HMG-COA HOMA-IR IL-6 IL-1β iNOS kg LDL MAPKs mg mL NFκ-B NS NSO PKB PON1 SBP TC TG TNF-α

body mass index blood pressure C-reactive protein diastolic blood pressure deoxyribonucleic acid fasting blood sugar gram hemoglobin A1c high density lipoprotein hydrargyrum hydroxy methyl glutaryle-COA homeostatic model assessment of insulin resistance interleukin-6 interleukin-1β inducible nitric oxide synthase kilogram low-density lipoprotein mitogen-activated protein kinases miligram milliliter nuclear factor kappa-B Nigella sativa Nigella sativa oil protein kinase B paraoxonase enzyme systolic blood pressure total cholesterol triglyceride tumor necrosis factor- A

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00010-6

43

© 2022 Elsevier Inc. All rights reserved.

44 TQ WC VLDL TURCOMP USDA β

4. Biological activities of black cumin (Nigella sativa) seed oil

thymoquinone waist circumference very low-density lipoprotein Turkısh National Food Composıtıon Database The United States Department of Agriculture beta

4.1 Introduction Nigella sativa (NS) is an annual herb with many pharmacological properties (Ermumcu & S¸ anlıer, 2017). NS has a strong historical basis and is a well-researched herb and has been used for medicinal applications in many countries (Silva et al., 2020). A large number of various several studies have been performed in the last decades to reveal biological activities and healing properties of NS. Its healthful effects against noncommunicable diseases, especially diabetes mellitus, different cancer types and cardiovascular diseases, dyslipidemia, hypertension, and obesity have been underlined (Ermumcu & S¸ anlıer, 2017; Silva et al., 2020). Among its many bioactive constituents, biological and pharmacological effects are dedicated to its most abundant components Thymoquinone (TQ), which is a chief bioactive constituent of Nigella sativa oil (NSO) (Ijaz et al., 2017). The positive effects of NS seeds and NSO on health are often due to the content of thymoquinone. The oil extracted from NS seeds is frequently used for its biological activities and several studies have shown that the NSO has many activities such as antiinflammatory (Mahboubi, 2018), antioxidant (Burits & Bucar, 2000; Ramadan, 2016), antitumor (Khan et al., 2011; Salim, 2010), antibacterial (Hassanien et al., 2015; Ramadan, 2016), and anticancer (Bordoni et al., 2019). In these days, studies have addressed the possibility that NSO may improve glucose homeostasis and lipid profile (Najmi et al., 2008; Rashidmayvan et al., 2019). Furthermore, pharmacological studies highlighted the gastroprotective, hepatoprotective, antitussive, cardioprotective and antihypertensive properties of NSO (Amin & Hosseinzadeh, 2016; Burits & Bucar, 2000; Hassanien et al., 2015; Mollazadeh et al., 2017; Salim, 2010). The NSO is generally recognized as safe (as a food and herbal medicine) by the USDA (Silva et al., 2020).

4.2 Nigella sativa seed and its chemical composition Nutritional value of NS seeds are high and NS contains dietary fiber, proteins (21%
31%), carbohydrates (25%
40%), minerals (3.7%
7%), vitamins (1%
4%) (Silva et al., 2020), and includes other components [fixed oil (22%
38%), volatile oil (0.40%
1.5%), saponins (0.013%), and alkaloids (0.01%)] depending on the region (Amin & Hosseinzadeh, 2016; Silva et al., 2020). Also the NSO includes certain fatty acids including linoleic acid 44.7%
56%, oleic acid 20.7%
24.6%, and linolenic acid 0.6%
1.8%) and volatile oil including thymoquinone (TQ) 30%
48% (Rashidmayvan et al., 2019). Notably, biological activity of NSO has been associated with its thymoquinone component and TQ can contribute to its biological properties (Amin & Hosseinzadeh, 2016). It was shown in

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4.3 Biological activities of Nigella sativa seed and its oil

TABLE 4.1 The components values of Nigella sativa seed (100 g) (Food Data central USDA, http; Turkish Food Composition Database, http). Component

TURKOMP

USDA

Energy (kcal)

387

400

Water (g)

5.98

-

Ash (g)

4.04

-

Protein (g)

22.50

16.67

Nitrogen (g)

3.60

-

Fat, total (g)

20.18

33.33

Carbohydrate (g)

10.16

50

Fiber, total dietary (g)

37.14

-

Calcium, Ca (mg)

-

-

Iron (mg)

-

12

Table 4.1 components values of NS from Turkish national food composıtıon database (TURCOMP) and Food Data Central of United States Department of Agriculture (USDA).

4.3 Biological activities of Nigella sativa seed and its oil 4.3.1 Antioxidant properties Biological and therapeutic potential of NSO has been widely studied (Rashidmayvan et al., 2019; Silva et al., 2020; Sultan et al., 2009). It was stated that both the NSO and its the main compound of the volatile oil TQ have appreciable free radical scavenging properties (Bourgou, Pichette, Marzouk, et al., 2012). The antioxidant effect of TQ have an important role in NSO’s mechanism of action and improves the body’s defense system (Ali & Blunden, 2003). Even low concentrations of NSO suppress the formation of lipid peroxide and lactate dehydrogenase. NSO increases the superoxide dismutase and glutathione availability and falls lipid peroxidation and free radical generation at the same time (Ahmad et al., 2021; Bourgou et al., 2012).

4.3.2 Antihyperlipidemic and antihypercholesteremic properties Coronary heart, peripheral vascular and cerebrovascular disease, heart failure with hypertension are among the cardiovascular diseases have the highest causes of death worldwide. Many cardioprotective effects of NS have been noted. Ahmad et al., 2021. NS is a rich source of unsaturated fatty acids such as linoleic acid and oleic acid and it contains small amount of linolenic, arachidonic, and eicosenoic acid, which constitute 80%
84% of fatty acids in this seed and may have roles in the hypolipidemic effect of

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4. Biological activities of black cumin (Nigella sativa) seed oil

this plant. Several mechanisms are proposed to explain the hypolipidemic effect of NS (Mohtashami & Entezari, 2016). • Increase in cholesterol metabolism due to a rich source of polyunsaturated fatty acids. • Inhibition of lipid peroxidation and reduction in cholesterol synthesis in the liver by antioxidant factors such as phytosterols and flavonoids. • Reduction insulin resistance and dyslipidemia throughout antioxidative action of thymoquinone. • Increase in the secretion of cholesterol in the bile and hence excretion in feces. • Reduction of serum TG due to presence of nigellamin that act like a clofibrate. • Regulation of cholesterol synthesis through effect on key enzyme HMG-COA reductase (Hydroxy Methyl Glutaryle-COA). It has been illustrated that the volatile oils of NG and its active component TQ have been shown to have positive effects on hyperglycemia and hyperlipidema (Ahmad et al., 2021). TQ has been stated that improving hyperlipidemia and protecting against the development of atherosclerosis. According to many studies, NG’s potential antihyperglycemia and antihylipidemia activities are based on its antioxidant content and it was shown that indicate that NG decreases lipid peroxidation and increases antioxidant enzymes (Ahmad & Beg, 2013; Amini et al., 2011). Hypercholesterolemia status is associated with increased triglyceride (TG), total cholesterol (TC), low-density lipoprotein (LDL), high density lipoprotein (HDL) and very low-density lipoprotein (VLDL) levels. Increase in circulating HDL levels and decrease in LDL levels have positive effects on hypercholesterolemia and reduce the risk of cardiovascular disease. Ahmad and Beg (2013). NSO have many phytochemicals that can affect hypocholesterolemia (Rashidmayvan et al., 2019). NS and its important active ingredient TQ show its antihypercholesterolemic effect by reducing HMG-CoA reductase enzyme, which is one of the mechanisms that plays a role in the reduction of cholesterol synthesis and also has protective effects on dyslipidemia. Furthermore, NS is stated that due to its ability to protect LDL from oxidation and neutralize other radicals including hydrogen peroxide, paraoxonase enzyme (PON1), which has an antioxidant function, increases the protein indicator arylesterase activity and shows antihyperlipidemic properties (Ahmad & Beg, 2013; Amini et al., 2011; Ermumcu & S¸ anlıer, 2017). In a study, it was observed hyperlipidemic individuals who used for 4 weeks 2 g/day amount of NSO have a significant decrease in TC, LDL, and TG levels. But there is not beneficial effect on HDL level of individuals (Sabzghabaee et al., 2012). And also another 2-month intervention study was shown that NS has positive effects on the lipid profiles of menopausal women more than control group. Decreased total cholesterol, LDL, TG, and increased HDL levels were seen in NS treated group (Boskabady et al., 2010). Moreover, a study showed that NSO had potential hypolipidemic effects and NSO treated group had significant decreased fasting blood cholesterol, LDL, triglyceride levels than placebo group at the end of the study (Kaatabi et al., 2012). The effect of NSO on antiatherogenic potential was examined in rabbits. Rabbits were divided into five groups. It was specified that four groups as hypercholesteremic group and the others as normal. One of the hypercholesteremic groups received a diet including 1% cholesterol and rat were fed that diet for 3 weeks. Later on, NS powder (1 g/kg), NSO (0.5 g/kg) and simvastatin (10 mg/day) were added to the diets of the remaining groups for 8 weeks. Feeding

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47

hypercholesteremic rabbits with NS either in powder or oil forms was shown to reduce TC and LDL levels significantly and enhance HDL levels after treatment for 8 weeks compared to the positive control group (Al-Naqeep et al., 2011). Similar to these results, rats were fed an atherogenic diet and they intaken 10 mg/mL thymoquinone by gavage for 30 days and their blood lipids positively affected end of the study (Ahmad & Beg, 2013). In another study, different doses of NS supplement were given to evaluate effects of on the serum lipid profile in rats. Rats were fed with different amount of NS supplement (100, 200, 400, and 600 mg NS/kg, respectively) per day 4 weeks, and it was found that there was a significant decrease in TC levels in experimental group than control at the end of the study (Kocyigit et al., 2009). Therefore, it has been suggested that NS and NSO can be used as a supplement to effective drugs that lower lipid profile. It was shown that the intake of 1000 mg/day NSO for 8 weeks could have useful effects on lipid profile of individuals in an another study (Rashidmayvan et al., 2019).

4.3.3 Antihypertensive properties NS and TQ were reported to contribute to a reduction in blood pressure and to reduce hypertension via various mechanisms (Keyhanmanesh et al., 2014; Leong et al., 2013). Mechanisms for lowering blood pressure (BP) using NS supplementation, including the following (Mohtashami & Entezari, 2016; Ta¸sar, 2012): • Antioxidant activity of thymoquinone, polyphenols, and flavonoids in NS that cause nitric oxide production and vasodilator effect. • Presence of linoleic acid that affects ionic fluxes across the vascular endothelial cells. • Presence of oleic acid that regulates lipid structure in membrane and control G-protein. • Mediated signaling that leads to lowering of BP. • Calcium channel-blocking activity by NS • Inhibition of angiotensin-converting enzyme by flavonoids. In a study carried out on healthy individuals aged between 34 and 63 years, have a systolic and diastolic blood pressure (SBP and DBP) range of 110
140 and 60
90 mm Hg, respectively. Participants were divided as a control and intervention group. The intervention group intook with 2.5 mL NSO every 12 hours twice a day (5 mL/day total) for 8 weeks. A significant decrease in SBP and DBP was observed in the NSO given group (Fallah Huseini et al., 2013). In another randomized controlled double-blind dose-response study conducted on mild hypertension patients aged between 35 and 50 years for 8 weeks, participants were divided into three groups. Placebo, 100 and 200 mg NS extract were given to groups. The SBP and DBP were decreased in the intervention group who intake NS extract compared to initial levels and the placebo group. Furthermore, NS extract decreased the SBP and DBP depending on its amount. In line with these results, it has been reported that the use of NS extract for 2 months in patients with mild hypertension has a blood pressure lowering effect (Dehkordi & Kamkhah, 2008).

4.3.4 Antidiabetic properties Many countries around the world show mostly a high tendency to use herbal medicine in the treatment of diabetes. There is a tendency for the use of herbal treatments in individuals

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due to the side effects of chemical drugs. The World Health Organization convinces researchers to investigate the benefits and side effects of the potential therapeutic effects of herbs (Heshmati & Namazi, 2015). NS and TQ have useful effects to control glucose and lipid profiles in diabetics. Although the molecular mechanism of TQ has not been completely understood. It was stated that TQ can increase glucose levels using by increasing the serum concentration and also decreases blood glucose by preventing gluconeogenesis (Benhaddou-Andaloussi et al., 2008; Kaatabi et al., 2015). TQ can increase insulin secretion by improving the energy metabolism of mitochondria. It has been suggested that TQ can activate the mitogen-activated protein kinases (MAPKs) and protein kinase B (PKB) pathways. In addition to they promotes the intracellular insulin receptor pathways so insulin concentration increases. Besides TQ can reduce the expression of gluconeogenic enzymes and the production of hepatic glucose (AL-Naqeeb & Ismail, 2009; Heshmati & Namazi, 2015; Nammi et al., 2010). It was stated that obese women who consumpted 3 g NSO daily for 8 weeks have decreased insulin levels. Mahdavi et al. (2016). Furthermore, TQ protects β-cell integrity and can be effective against oxidative stress (Kaatabi et al., 2012; Kaatabi et al., 2015). Glycemic control involving factors such as FBS and HbA1c are useful parameters in the detection and control of diabetes and increased blood glucose in the subjects. It was evaluated that effects of NS supplement on glycemic control and antioxidant capacity in type 2 diabetic patients used hypoglycemic drugs in a double-blind placebocontrolled study. About 2 g/day NS was given to intervention group for 1 year. Hemoglobin A1c (HbA1c) levels and fasting blood glucose levels were decreased significantly. Total antioxidant capacities, superoxide dismutase and glutathione levels increased significantly and also insulin resistance of individuals decreased and β cell activity increased in intervention group (Kaatabi et al., 2015). In an another study, Three different NS powder doses (1, 2, and 3 g/ day) were given to type 2 diabetic patients. Patients with intaken 2 g NS powder per day had significant decreases in insulin resistance and β cell function indicators including postprandial blood sugar, HbA1c, homeostatic model assessment of insulin resistance (HOMA-IR) levels than other groups. The most effective does was 2 g NS and so given NS with hypoglycemic agents may have more positive benefits (Bamosa et al., 2010). In another study, 2.5 mL NSO were given to patients with insulin resistance taken hypoglycemic drugs twice daily for 60 weeks and their TC, LDL, and fasting blood sugar (FBS) levels decreased significantly (Najmi et al., 2008). In addition, NSO is effective as an alternative treatment in individuals with insulin resistance. NS has beneficial effects in diabetic and dyslipidemic patients (Najmi et al., 2008). In another study, diabetic rats were fed 50 mg/day TQ for 8 weeks and it was found that NS play an important role in the prevention of diabetic neuropathy (Omran, 2014). In another study, individuals with type 2 diabetes were given 3 g NS per day during 3 months. It was found that the insulin levels and resistance and FBS levels of the patients decreased (Awad et al., 2016; Benhaddou-Andaloussi et al., 2011). Antidiabetic properties of NS is related to the following (Bamosa, 2015; Mohtashami & Entezari, 2016): • Reduction in oxidative stress and maintenance of the integrity of pancreatic β cells that lead to increased blood insulin level. • Presence of thymoquinone with antioxidant activity. • Activation of insulin receptors and improvement in tissue sensitivity to insulin. • Decreased gluconeogenesis in the liver. • Reduction in glucose absorption from the intestine

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4.3.5 Antiobesity properties Obesity has become an important public health problem in all around the world. In recent years, the use of herbal supplements are widely used in weight loss (HasaniRanjbar et al., 2013; Hassanien et al., 2015). NS and TQ show antiobesity effects especially NSO in combination with a low-calorie diet promotes weight loss in obese women (Ahmad & Beg, 2013; Vanamala et al., 2012). A 25% of food intake decreased in rats were fed with NSO. Therefore, NSO might have anorectic effects and can cause decreasing food intake and body weight (Le et al., 2004). Diabetic rats were fed 300 mg/day NS extract during 30 days and they had significant decreases in their body weight (Datau et al., 2010b). Human studies are very limited to examine effect of NS on obesity. 50 obese men taken NS 3 g/day for 3 months in a randomized controlled double-blind single study. Body weight, waist and hip circumference of participants had significant decreased (Datau et al., 2010a). In an another study, individuals taking one gram of NSO twice a day had a significant reduction in their body weight and body mass index (BMI) after 12 weeks (Hussain et al., 2017). With regard to anthropometric parameters [weight and waist circumference (WC)], there are remarkable results. It was reported that effect of NS in reducing weight or WC statistically significant (Qidwai et al., 2009). However, when NS given to normal weight participants, there was not any significant change in their body weight (Nader et al., 2010; Qidwai et al., 2009).

4.3.6 Antiinflammatory properties There is a growing interest to find alternative treatments that can fight against inflammation about plants with bioactive compounds. NS has a very rich phytochemical content and a strong immunomodulatory activity. NS has been used in various inflammatory conditions for centuries because of its antiinflammatory and antioxidant activities (Pop, Sabin, et al., 2020). Among bioactive compounds identified in NSO, TQ was intensively studied. There are also studies showing that it alters interleukins, interferons and cytokine levels. Active components of NS increase the immunomodulatory properties through T cells and natural killer (NK) cells (Ahmad et al., 2021). It was shown that intake of 1000 mg of NSO for 8 weeks could decrease inflammatory factors [C-reactive protein (CRP), tumor necrosis factor- α (TNF-α), and interleukin-6 (IL-6)] in the patients with nonalcoholic fatty liver (Rashidmayvan et al., 2019). Another study was reported that a significant antiinflammatory effect of NSO demonstrated by reduction of paw edema compared to the control group (Pop, Sabin, et al., 2020). The effect of NSO on central inflammation process TNF-α, IL-6, interleukin-1β (IL-1β), and inducible nitric oxide synthase (iNOS) as well as the expression level of nuclear factor kappa-B (NFκ-B) were examinated in both serum and brain tissue in diabetes animal model. Serum antiinflammatory levels and brain inflammatory cytokines levels were significantly lowered in the groups treated with NSO (Noor et al., 2015). Therefore, according to the literature studies, the use of NSO represents a very good promise in the prevention and treatment of chronic inflammatory disorders (Pop, Trifa, et al., 2020)

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4.3.7 Anticancer properties Cancer is a leading and an important cause of death (10 million deaths in 2020) (Ferlay et al., 2018). The effect of NS against cancer has been shown but mechanisms are still not clearly explained (Mollazadeh et al., 2017). TQ is considered to have antioxidant, anticancirogenic and antimutagenic properties. Oxidative stress causes many cancer types. It was stated that antioxidant properties of NS have beneficial effects in cancer and TQ increases the antioxidant enzymes activities. Badary et al. (2003; Randhawa & Alghamdi, 2011). Function of NS and its extract were evaluated in vivo and in vitro studies for different cancer types. It was found that NS increases activation and numbers of macrophage cell so NS can be important for killing various cancerous cell types (Randhawa & Alghamdi, 2011). NS and TQ showed cytotoxicity properties and anticancer activities against lung cancer cell numbers and by preventing cell proliferation approximately 90% (Hammad Shafiq et al., 2014; Rooney & Ryan, 2005). Also NS have been shown to be effective activity in breast cancer (Hammad Shafiq et al., 2014). In addition NS can prevent carcinogenesis by reducing DNA damage in colon tissues exposed to toxic agents (Abukhader, 2012; ElMahmoudy et al., 2002).

4.3.8 Potential toxicity of Nigella sativa Oil Healthy individuals taken of NSO (5 mL/day) for 8 weeks have not seen any liver, kidney, or gastrointestinal side effects according to evidenced by laboratory test results but it was only experienced mild nausea at the beginning of study, and the nausea disappeared at the second week of intervention (Fallah Huseini et al., 2013). Type 2 diabetes mellitus were given NSO (obtained from 0.7 g of seeds) for 6 weeks and it was reported acceptable liver and kidney safety (Tavakkoli et al., 2017). Another study was reported that obese men taken 3 g/day NS for 12 weeks have no discoverable adverse effects (Datau et al., 2010a). NS has been seen as a safe herbal product. It would be a potential herbal remedy by clinical trials results (Tavakkoli et al., 2017).

4.4 Conclusions and suggestions Health benefits of the NS, NS extracts and NSO in different doses and durations have been shown in different types of studies. Studies clearly suggest that NS and NSO are an important herbal treatments in the traditional medicine. Hypoglycemic and hypolipidemic properties of NS are understood so that NS can be used daily and it can be beneficial for a healthy diet. Although the effect and mechanism of function of NS on some diseases have been demonstrated but human studies are limited, therefore, more clinical and animal studies require.

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404. Dehkordi, F. R., & Kamkhah, A. F. (2008). Antihypertensive effect of Nigella sativa seed extract in patients with mild hypertension. Fundamental & Clinical Pharmacology, 22(4), 447
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El-Mahmoudy, A., Matsuyama, H., Borgan, M. A., Shimizu, Y., El-Sayed, M. G., Minamoto, N., & Takewaki, T. (2002). Thymoquinone suppresses expression of inducible nitric oxide synthase in rat macrophages. International Immunopharmacology, 2(11), 1603
1611. Ermumcu, M. S¸ . K., & S¸ anlıer, N. (2017). Black cumin (Nigella sativa) and its active component of thymoquinone: effects on health. Food and Health, 3(4), 170
183. Fallah Huseini, H., Amini, M., Mohtashami, R., Ghamarchehre, M. E., Sadeqhi, Z., Kianbakht, S., & Fallah Huseini, A. (2013). Blood pressure lowering effect of Nigella sativa L. seed oil in healthy volunteers: A randomized, double-blind, placebo-controlled clinical trial. Phytotherapy Research, 27(12), 1849
1853. Ferlay, J., Ervik, M., Lam, F., Colombet, M., Mery, L., Pin˜eros, M., & Bray, F. (2018). Global cancer observatory: Cancer today (p. 2020) Lyon: International Agency for Research on Cancer. Food Data central (USDA). https://fdc.nal.usda.gov/. Hammad Shafiq, A. A., Masud, T., & Kaleem, M. (2014). Cardio-protective and anti-cancer therapeutic potential of Nigella sativa. Iranian Journal of Basic Medical Sciences, 17(12), 967. Hasani-Ranjbar, S., Jouyandeh, Z., & Abdollahi, M. (2013). A systematic review of anti-obesity medicinal plantsan update. Journal of Diabetes & Metabolic Disorders, 12(1), 1
10. Hassanien, M. F., Assiri, A. M., Alzohairy, A. M., & Oraby, H. F. (2015). Health-promoting value and food applications of black cumin essential oil: an overview. Journal of Food Science and Technology, 52(10), 6136
6142. Heshmati, J., & Namazi, N. (2015). Effects of black seed (Nigella sativa) on metabolic parameters in diabetes mellitus: A systematic review. Complementary Therapies in Medicine, 23(2), 275
282. Hussain, M., Tunio, A. G., Arain, L. A., & Shaikh, G. S. (2017). Effects of Nigella Sativa on various parameters in patients of non-alcoholic fatty liver disease. Journal of Ayub Medical College Abbottabad, 29(3), 403
407. Ijaz, H., Tulain, U. R., Qureshi, J., Danish, Z., Musayab, S., Akhtar, M. F., Saleem, A., Khan, K. A. U. R., Zaman, M., Waheed, I., Khan, I., & Abdel-Daim, M. (2017). Nigella sativa (prophetic medicine): A review. Pakistan Journal of Pharmaceutical Sciences, 30, 1. Kaatabi, H., Bamosa, A. O., Badar, A., Al-Elq, A., Abou-Hozaifa, B., Lebda, F., Al-Khadra, A., & Al-Almaie, S. (2015). Nigella sativa improves glycemic control and ameliorates oxidative stress in patients with type 2 diabetes mellitus: Placebo controlled participant blinded clinical trial. PLoS One, 10(2), e0113486. Kaatabi, H., Bamosa, A. O., Lebda, F. M., Al Elq, A. H., & Al-Sultan, A. I. (2012). Favorable impact of Nigella sativa seeds on lipid profile in type 2 diabetic patients. Journal of Family & Community Medicine, 19(3), 155. Keyhanmanesh, R., Gholamnezhad, Z., & Boskabady, M. H. (2014). The relaxant effect of Nigella sativa on smooth muscles, its possible mechanisms and clinical applications. Iranian Journal of Basic Medical Sciences, 17(12), 939. Khan, A., Chen, H. C., Tania, M., & Zhang, D. Z. (2011). Anticancer activities of Nigella sativa (black cumin). African Journal of Traditional, Complementary and Alternative Medicines, 8(5S). Kocyigit, Y., Atamer, Y., & Uysal, E. (2009). The effect of dietary supplementation of Nigella sativa L. on serum lipid profile in rats. Saudi Medical Journal, 30(7), 893
896. Le, P., Benhaddou-Andaloussi, A., Elimadi, A., Settaf, A., Cherrah, Y., & Haddad, P. (2004). The petroleum ether extracts of Nigella sativa seeds exert insulin sensitizing and lipid lowering action in rats. Journal of Ethnopharmacology, 94(2
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1330. Ta¸sar, N. (2012). Protective effects of Nigella sativa against hypertension-induced oxidative stress and cardiovascular dysfunction in rats. Tavakkoli, A., Mahdian, V., Razavi, B. M., & Hosseinzadeh, H. (2017). Review on clinical trials of black seed (Nigella sativa) and its active constituent, thymoquinone. Journal of Pharmacopuncture, 20(3), 179. Turkish Food Composition Database. http://www.turkomp.gov.tr/. Vanamala, J., Kester, A. C., Heuberger, A. L., & Reddivari, L. (2012). Mitigation of obesity-promoted diseases by Nigella sativa and thymoquinone. Plant Foods for Human Nutrition, 67(2), 111
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C H A P T E R

5 Biological activities of Moringa seeds oil Yosvany Dı´az-Domı´nguez 1 , Ramo´n Piloto-Rodrı´guez2 , Elina Ferna´ndez-Santan 1 , Maylin Rondo´n-Macias3 and Danger Tabio-Garcı´a 3 1

Faculty of Chemical Engineering, Technical University of Havana, Havana, Cuba 2Center for the Studies of Renewable Energies, Technical University of Havana, Havana, Cuba 3Faculty of Chemical Sciences, Autonomous University of Chihuahua, Chihuahua, Mexico

Abbreviations 1H-NMR AMPs CACO-2 DNA DPPH GLC HeLa HepG2 HSV 1 IC50 L929 MCF-7 MIC PUFA TB UV

proton nuclear magnetic resonance antimicrobial Peptides colon cancer deoxyribonucleic acid 1,1-diphenyl-2- picrylhydrazy gas liquid chromatography cervical cancer liver cancer Herpes simplex virus type 1 concentration of 50% inhibition mouse fibroblasts breast cancer minimal inhibitory concentration polyunsaturated fatty acid tuberculosis ultraviolet

5.1 Introduction People have been using plants for different purposes since many centuries. Plants generally contain 11 phyto constituents such as anthraglycosides, arbutin, bitter drugs,

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flavonoids, alkaloids, saponins, coumarins, phenols, carboxylic acids, terpenes, and valepotriates (Mudasser et al., 2015). These components are responsible for the various biological activities, for example, antimicrobial, antioxidant, anticancer, and other activities. For this reason, plants are significant for the treatment of the ailments in the world (Adumu et al., 2017; Srivastava et al., 2020). Phenolic compounds are known to possess different pharmacological activities, among which antioxidant and antimicrobial effects have recently received more attention (Mudasser et al., 2015). The products derived from several herbs and plants, being a source of multifunctional curing agents and bioactive compounds, are relatively considered safe for consumption. According to the Food and Agriculture Organization’s (FAO) report, about 70%
80% of the world’s population, 25% of the synthesized drugs are manufactured from medicinal plants (Adumu et al., 2017). In the last few decades, there has been an exponential growth in the field of herbal medicine (Mudasser et al., 2015). Different plants are referenced for their typical therapeutic properties, for example, pain relief, calming, antipyretic, hostile to diabetic, etc. Moringa oleifera (M. oleifera) is one such plant utilized due to its diverse therapeutic properties (Srivastava et al., 2020). This plant is consumed as food for its nutritional value, and according to Ayurvedic medicine (Singh, 2012) it is attributed with properties for the treatment of certain ailments such as asthma, epilepsy, eye and skin diseases, fever and hemorrhoids (Sanjay & Dwivedi, 2015; Vela´zquez et al., 2016). M. oleifera is health restorative plant and it is recognized in tropical and subtropical countries (Srivastava et al., 2020).

5.2 Phytochemistry Phytochemicals are chemicals produced by plants. Commonly, though, the word refers to only those chemicals which may have an impact on health, or on flavor, texture, smell, or color of the plants, but are not required by humans as essential nutrients. An examination of the phytochemicals of Moringa species affords the opportunity to examine a range of fairly unique compounds (Fahey, 2005). M. oleifera is rich in compounds containing simple sugar, rhamnose and a fairly unique group of compounds called glucosinolates and isothiocyanates (Anwar, & Latif, Ashraf, et al., 2007; Fahey et al., 2001). Many phytoconstituents of M. oleifera have been isolated and studied. The main phytochemicals obtained from this plant are shown in Table 5.1 (Nogueira et al., 2017). Some of the detected phytochemicals have been reported to be antioxidant, antimicrobial, antiviral, antileukemic, antiotitis, antianemic, antiinflammatory, antifungal, anticancer, antiulcerative, and antipyretic in nature. Basically, these phytochemicals are synthesized in plants partly as a response to ecological and physiological pressures such as pathogen and insect attack, ultraviolet (UV) radiation and wounding (Falowo et al., 2018).

5.3 Botanical descriptions and geographical distribution The genus Moringa is one of the types found in the Moringaceae family along with Anoma and Hyperanthera. It is well-known as the “drumstick” or “horseradish” family

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5.3 Botanical descriptions and geographical distribution

TABLE 5.1 Phytoconstituents of different parts of Moringa oleifera (Nogueira et al., 2017). Plant part

Phytoconstituents

Group

Seeds

β-sitosterol

Phytosterol

Leaves, stem and roots

4-α-L-rhamnopyranosyloxy-benzylglucosinolate

Glucosinolate

Leaves, stem and roots

4-(α-L-rhamnosyloxy-benzyl) isothiocyanate

Glucosinolate

Leaves

4-O-glucopyranosyl-caffeoylquinic acid

Caffeoylquinic acid

Seeds

Glycerol-1-(9-octadecanote)

Glycoside

Seeds, leaves, stem and roots

Kaempferol

Flavonoid

Leaves and seeds

Niazimicin

Glycoside

Leaves and seeds

Niazinin

Glycoside

Leaves

((α-L-rhamnosyloxy)benzyl) carbamate

Glucosinolate

Seeds, leaves, stem and roots

Quercetin

Flavonoid

Roots and flowers

Pterygospermin

Glycoside

(Abd Rani et al., 2018) and consists of 13 species distributed through in all tropical and subtropical regions. The species and their distribution are shown in Table 5.2. Among the 13 species, present research is limited to M. oleifera, Moringa peregrina (M. peregrina), Moringa stenopetala (M. stenopetala), and Moringa concanensis (M. concanensis). As the other species are endemic to Madagascar and Northeast Africa, they are being evaluated less as there is less exploration for naturally occurring bioactive substances in these locations (Abd Rani et al., 2018). M. oleifera is the most widely known and utilized species. This plant, native to India, has been introduced in all tropical and subtropical regions (Anwar & Rashid, 2007; Dı´az, Tabio, Goyos, et al., 2017; Jacques et al., 2020; Srivastava et al., 2020). It grows mainly on semiarid zones, at elevations from sea level to 1400 m (Mishra et al., 2011). The growth is fast and resistant to drought (it tolerates a wide range of precipitation with minimum requirements estimated at 250 mm and maximum at more than 3000 mm and a pH of 5.0
9.0) (Dı´az, Tabio, Rondo´n, et al., 2017; Jacques et al., 2020). The tree ranges in height from 5 to 12 m with an open, umbrella-shaped crown, straight short trunk with corky, whitish bark, soft, spongy wood. It has slender, wide spreading, drooping, fragile branches. The foliage can be evergreen or deciduous depending on climate. Leaves are long petiole about 20
50 cm long, with four to six pairs of pinnae bearing two pairs of opposite leaflets that are elliptical. The fruits grow up to 60 cm which when mature became dry and brown in color. Mature seeds are round or triangularshaped, the kernel surrounded by a light wooded husk with three papery wings (Ghazali & Abdulkarim, 2011). Moringa is believed to have multiple medicinal qualities. Most parts of this plant are used in the treatment of illness and production of drugs against bacteria, fungi, virus, and other pathogens in human beings (Falowo et al., 2018). For example, the barks, roots, leaves, and flowers of Moringa tree are used in traditional medicine and folk remedies in

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5. Biological activities of Moringa seeds oil

TABLE 5.2 Moringa species throughout the world (Abd Rani et al., 2018). Species

Country

Trivial name

Moringa arborea Verdcourt

Kenya, Somalia




Moringa borziana Mattei

Kenya, Somalia




Moringa concanensis Nimmo India




Moringa drouhardii Jumelle

Southern Madagascar




Moringa hildebrandtii Engler

Southwest Madagascar

Hildebrandt’s Moringa

Moringa longituba Engler

Kenya, Southeast Ethiopia, Somalia

Moringa tubiflora

Moringa oleifera Lam.

India

Horseradish, Ben-oil Drumstick, Kelor

Moringa ovalifolia Dinter ex Berger

Namibia, Southwest Angola

Phantom Tree, Ghost Tree, African Moringo

Moringa peregrina Forssk. Ex Red Sea, Arabia, Fiori Northeast Africa

Ben tree, wispy-needled Yasar tree, Wild drumstick tree, Yusor, Al Yassar, Al Ban

Moringa pygmaea Verdcourt

North Somalia




Moringa rivae Chiovenda

Kenya, Ethiopia

Swanjehro

Moringa ruspoliana Engler

Kenya, Ethiopia, Somalia


Moringa stenopetala (Baker f.) Cufodontis

Kenya, Southwest Ethiopia, Somalia

Cabbage tree, Haleko, Shelagda, Shiferaw

many countries. The seeds are one of the best natural coagulants, possess antimicrobial properties and are also used for treatment of highly turbid water (Manzoor et al., 2007; Rondo´n et al., 2017). The Moringa seeds oil is golden yellow and contains high amounts of oleic acid, approximately 75%. Oleic acid has a strong oxidative stability compared to polyunsaturated fatty acids, essential for long storage and high temperature frying processes. The oil has several uses such as cosmetics, medicinal and potential for biodiesel production (Dı´az, Tabio, Goyos, et al., 2017). Since many literature reports, the leaves and the seeds are the parts of the plant of interest (Dhakad et al., 2019; Dı´az, Tabio, Rondo´n, et al., 2017; Leone et al., 2015; Marrufo et al., 2013; Pe´rez et al., 2010).

5.4 Cultivation for leaves and seed production There are two methods to obtain M. oleifera plants: sowing and the use of cuttings (Leone et al., 2015, 2016). Sowing requires selection of the seeds when they are easily available and human labor is limited, while the possibility to transplant seedlings allows flexibility in field planting even if it requires extra labor and costs (Leone et al., 2015). For seed production, sowing is preferred as improved varieties can be selected for cultivation, ensuring proper and profitable production. Seed production, according to harvest

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59

5.5 Seeds of Moringa species

and management practices, requires a low density plantation (typically, 2.5
2.5 m or 3
3 m) with a triangular pattern, although 1.2 m along a row and 5 m between rows also seems suitable for satisfactory yields. For leaf production, the spatial distribution in planting can vary: intensive (spacing from 10
10 cm to 20
20 cm), semi-intensive (spacing 50
100 cm), or integrated into an agroforestry system (spacing distance of 2
4 m between rows) (Leone et al., 2016). M. oleifera is also propagated through cuttings (0.2
1.0 m long), with recommended tree to tree spacing of 1.2 and 5 m between rows (for pod yield), to obtain the desirable population of 1666 trees/ha. For foliage production, cuttings are planted with a close spacing to obtain 1 million trees/ha2. The tree starts bearing fruits after 6 or 8 months, with a low fruit set in the initial 1
2 years, however, the yield increases in the following years (Adumu et al., 2017). Although each plant can produce a large quantity of seeds when fertilization is adequate (Leone et al., 2016). Several studies (Dı´az, Tabio, Goyos, et al., 2017; Ghazali & Abdulkarim, 2011; Leone et al., 2016; Mashiar et al., 2009) focused on seeds and leaves of Moringa because of the oil content and its biological activities.

5.5 Seeds of Moringa species The seeds are generally 2.5
3 cm in length. When the husk is taken away, the endosperm is discovered. It is whitish and very oleaginous. Seed weight and kernel percentage are highly variable between Moringa species. Table 5.3 resumes the characteristics and chemical composition of seeds from Moringa species. M. oleifera and M. concanensis have the highest kernel yield per seed, but the latter has very small seeds (Boukandoul et al., 2018). All Moringa species are rich in oil; nevertheless, the variations of this content are associated with several factors such as cultivars, environmental and geographical conditions (Boukandoul et al., 2018). The moisture, fiber, ash and protein content of M. oleifera and M. TABLE 5.3 Characteristics and chemical composition of Moringa seeds (Abd El Baky & El-Baroty, 2013; AlDabbas et al., 2010; Anwar & Rashid, 2007; Boukandoul et al., 2018; Ejigu et al., 2010; Lalas et al., 2003; Manzoor et al., 2007; Osman & Abohassan, 2012; Seifu, 2014). Species

Whole seed weight (g)

Kernel proportion (%)

Oil content (%)

M. oleifera

0.3

75.0

M. peregrina

0.7

M. stenopetala M. Concanensis

g/100 g fresh weight Moisture (%)

Fiber (%) Ash (%)

Protein (%)

28.5
59.8

5.70

7.2

6.6

29.36

58.6

33.3
55.7

2.40

11.7
14.6 2.6

24.10

0.6
1.1

64.2
79.7

31.0
45.0

6.10

5.1

4.6

42.60

0.1

70.0
81.0

37.6
40.1

5.88

6.0

9.0

30.07

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5. Biological activities of Moringa seeds oil

concanensis were in close agreement, whereas M. peregrina shows lower values (moisture, ash and protein) than the above mentioned species. In addition, the high protein percentage demonstrated that seeds of Moringa species are a good source of this component, which could be utilized for animal food, fertilizer and natural coagulant in water treatment (Dı´az, Tabio, Goyos, et al., 2017; Rondo´n et al., 2017).

5.6 Moringa seeds oil 5.6.1 Fatty acid composition Moringa oil is characterized by a high content of monounsaturated fatty acids. The high degree of unsaturation is because of the high percentage of oleic acid (Abdulkareen et al., 2011; Dı´az, Tabio, Goyos, et al., 2017; Dı´az, Tabio, Rondo´n, et al., 2017). This result can be demonstrated by gas chromatographic analysis (Table 5.4) or proton nuclear magnetic resonance (1H-NMR)-spectrum determination (Fig. 5.1). The oleic acid content ranged around the same percentages for Moringa species as can be observed in Table 5.4. Saturated fatty acids are reduced, with palmitic, arachidic, and behenic acids being the most representative ones, and only traces of polyunsaturated fatty acids (Al-Juhaimi et al., 2016; Boukandoul et al., 2018; Dı´az, Tabio, Rondo´n, et al., 2017; Melaku et al., 2017). On the other hand, high levels of behenic acid were detected in all Moringa species. The presence of the behenic acid explains why the M. oleifera is also named “Ben-oil tree.” Moringa oils have usually low free fatty acid content (2%), making neutralization unnecessary. However, due to the presence of high amounts of phospholipids there is usually a need for degumming (Boukandoul et al., 2018). In addition, a comparison of the 1H-NMR spectra of Linseed, Olive, and M. oleifera oil (Fig. 5.2) shown that the fatty acid composition of Moringa oil is similar to olive oil, but with a higher content of oleic acid. TABLE 5.4 Fatty acid composition of Moringa seeds oil (adapted from Boukandoul et al., 2018). M. oleifera M. peregrina M. stenopetala M. concanensis

Fatty acid

Systematic name

Formula

Palmitic

Hexadecanoic

C16H32O2 5.3
10.5

5.4
12.4

6.0
6.2

9.7
11.0

Palmitoleic Hexadec-9-enoic

C16H30O2 0.4
5.7

0.5
3.7

1.0
1.3

0.0
2.4

Stearic

Octadecanoic

C18H36O2 2.9
11.9

3.5
7.0

4.0
7.1

3.6

Oleic

Cis-9-Octadecenoic

C18H34O2 66.5
81.7

65.4
80.0

63.0
76.4

67.3
83.8

Linoleic

Cis-9-cis-12 Octadecadienoic C18H32O2 0.3
1.0

0.3
0.7

0.0
0.7

0.8
1.8

Linolenic

Cis-9-cis-12

C18H30O2 0.01
0.2

0.01
0.2

0.1
0.2




Arachidic

Eicosanoic

C20H40O2 1.7
5.5

2.1
4.4

2.3
3.8

3.3
3.6

Eicosanoic

Cis-11-eicosenoic

C20H38O2 0.1
3.2

0.1
2.4

0.8
2.0

1.7
1.8

Behenic

Docosanoic

C22H44O2 2.9
8.1

2.4
7.8

5.3
6.1

7.0
7.6

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5.6 Moringa seeds oil

61

FIGURE 5.1 Proton nuclear magnetic resonance (1H-NMR)-spectrum of Moringa oleifera oil.

FIGURE 5.2 Proton nuclear magnetic resonance (1H-NMR) spectra of linseed, olive, and Moringa oleifera oils.

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5. Biological activities of Moringa seeds oil

5.6.2 Oxidative stability The different oxidation parameters of the Moringa seeds oil are shown in Table 5.5. Moringa seeds oil also presented a very good oxidative stability as indicated by the parameters shown in Table 5.5. The specific extinctions at 232 and 270 nm, which revealed the oxidative degradation and purity of Moringa oil, ranged from 1.38 to 3.17 and 0.67 to 0.69, respectively. The peroxide value fluctuated since 0.66
1.73 m eq/kg of oil and p-anisidine value (1.82
2.50), which measure hydroperoxide and α, β aldehydic secondary oxidation products of the oil (Anwar & Rashid, 2007). Peroxide values under 5 m eq O2/kg oil demonstrate a low content of oxidation products in the oil (Dı´az, Tabio, Goyos, et al., 2017). The higher resistance to oxidation process of Moringa species seeds oil can be attributed to the amount of α-tocopherol (Tsaknis, 1998). The induction period (hour, at 110 C), which is a characteristic of the oxidative stability of oil and fats, of the Moringa species seeds oil was variable. However, the lowest value is 8 hours, indicating a very good stability of Moringa oil. A high induction period and oxidative stability of Moringa species seeds oil, compared with those of conventional vegetable oils, were attributed to a significantly higher level of monounsaturated fatty acids, mainly C18:1 (oleic acid), which is less prone to oxidation than polyunsaturated (Anwar & Bhanger, 2003). Ogbunugafor et al. (2011) reported the total phenolic, flavonoid and antioxidant capacity of M. oleifera (Table 5.6) (Ogbunugafor et al., 2011). Phenolic compounds are a class of antioxidant agents which act as free radical terminators and also involved in retardation of oxidative degradation of lipids (Pourmorad et al., 2006). In addition, Odukoya (Odukoya et al., 2005) has reported a strong relationship between phenolic content and antioxidant activity in selected fruits and vegetables (Ogbunugafor et al., 2011). TABLE 5.5 Determination of the oxidative stability of Moringa seeds oil (Anwar & Rashid, 2007; Gharibzahedi et al., 2013; Lalas et al., 2003). M. oleifera

M. peregrina

M. stenopetala

M. concanensis

(λ232)

1.38

1.77

1.86

3.17

(λ270)

0.79

0.72




0.67

Peroxide value (meq/kg of oil)

1.27

0.66

1.65

1.73

p-anisidine value

2.50







1.82

8
60

8
30

12
36

9
11

Constituent Conjugated diene

Ɛ1%1 cm

Conjugated triene

Ɛ1%1 cm



Oxidative stability (h, at 110 C)

TABLE 5.6 Total phenol, flavonoid and antioxidant capacity of Moringa oleifera (adapted from Ogbunugafor et al., 2011). Parameter

M. oleifera oil

Total phenol (mg GAE/g)

40.17

Total flavonoid (mg RE/g)

18.24

Total antioxidant capacity (mg AAE/g)

37.94

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5.6 Moringa seeds oil

63

Thus, the presence of phenolic compounds in Moringa seeds oil is an added value to its nutritional and health potential. Besides, the existence of flavonoids in this oil which are also phenolic compounds, also improves the economic and health potential of the oil. This fully matched with previous findings which suggested that flavonoids carry out antioxidant action through scavenging or chelating process and are reported to play a preventive role in cancer and heart disease (Middleton et al., 2000). Therefore the importance of the antioxidant constituents of Moringa oil in the maintenance of health is strengthened as trend of the future is moving toward using foods as medicine in the management of various chronic diseases (Ogbunugafor et al., 2011).

5.6.3 Sterol and tocopherol composition Moringa oil is rich in phytosterols, consistently between 0.2 and 0.6 g/100 g oil [M. oleifera (0.25
0.56), M. peregrina (0.21) and M. stenopetala (0.10
0.58)] (Boukandoul et al., 2018). The composition of the sterol fraction, analyzed by gas liquid chromatography (GLC), is shown in Table 5.7 (M. concanens is seed oil sterol content was not found in previous literature reports). The sterol fraction of all Moringa seeds oils consisted mainly of campesterol, stigmaterol, β-sitosteroland Δ5-avenasterol, among of which β-sitosterol was the most predominant, complemented with trace amounts of others. There were significant differences between the sterols of Moringa seeds oil and olive oil. For example, the sum of campesterol and stigmasterol content in olive oil rarely exceeded 8%, while the values for all Moringa seeds oil presented in Table 5.7 were higher than 30% (Al-Dabbas et al., 2010). The tocopherol profile of Moringa seeds oil consisted of α-, γ-, and δ-tocopherol (Table 5.8). Most vegetable oils contain α-, γ-, and δ-tocopherols. δ-tocopherol exists in few oils similar to cottonseed, peanut, wheat germ, soybean and castor oils. The antioxidant activity of δ-tocopherol exceeds that of γ- and α-tocopherol (Tsaknis, 1998). High concentrations of tocopherols in Moringa seeds oil are expected to offer some protection during storage and processing. The tocopherols content of the olive oil [α-tocopherol (88.5 mg/kg), γ-tocopherol (9.9 mg/kg), δ-tocopherol (1.6 mg/kg)] was lower than that of the M. oleifera, M. peregrine, and M. stenopetala, whereas was similar to M. concanensis (mainly in α- and γ-tocopherols concentration) (Tsaknis, 1998). Anwar and Rashid (2007) reported that α-isomer of tocopherol has greatest vitamin E potency, whereas, δ-isomer of tocopherol has greater antioxidant efficacy than either γ- or α-tocopherols. Boukandoul et al. (2018) reported the vitamin E amount for Moringa seeds oil species [M. oleifera (9.0
28.7 mg/100 g), M. peregrina (20.0
26.9 mg/100 g), M. stenopetala (20.2
22.4 mg/100 g) and M. concanensis (11.5 mg/100 g)]. These results are dominated by α-tocopherol, which is relevant for human health. Moreover, the variability of vitamin E content could be explained due to the preservation of the oil or the extractive conditions (Boukandoul et al., 2018). The tocopherol content could depend on the extraction method used to obtain the oil; however, results in this context are controversial. Nevertheless, the tocopherol content is higher than that of other oils (Leone et al., 2016).

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5. Biological activities of Moringa seeds oil

TABLE 5.7 Sterol composition of Moringa seeds oil (Al-Dabbas et al., 2010; Anwar & Rashid, 2007; Lalas et al., 2003). Sterols (%)

M. oleifera

M. peregrina

M. stenopetala

Cholesterol




0.22

0.10

24-Methylenecholesterol

0.99

Campesterol

17.95

23.69

14.26

Campestanol

0.53

0.31

0.24

Δ -Campestanol

0.70







Stigmasterol

18.80

24.54

16.53

Cholerosterol

1.70

0.82

1.43

Stigmastanol

0.53




0.74

β-sitosterol

46.16

28.30

51.60

Δ -Avenasterol

0.84

0.74

1.18

Δ -Avenasterol

9.26

16.10

10.67

28-Isoavenasterol

1.04




1.37

Δ

0.76




0.33

Brassicastrol




0.08

0.05

Δ-




0.19




Sitostanol




0.51




Δ-




2.50




Δ- -Stigmastenol




0.50




Ergostadienol







0.34

7

7 5

7,14

-Stigmastanol

5,23

-stigmastadien

5,24

-Stigmastadienol

7

0.80

TABLE 5.8 Tocopherol contents (mg/kg) of Moringa oil (Anwar & Rashid, 2007; Lalas et al., 2003; Manzoor et al., 2007; Tsaknis, 1998). Constituents

M. oleifera

M. peregrina

M. stenopetala

M. concanensis

α-Tocopherol

140.50

145

91.79

72.11

γ-Tocopherol

63.18

58

32.75

9.26

δ-Tocopherol

61.70

66

77.20

33.87

5.6.4 Biological activities of Moringa seeds oil The attraction of Moringa medicinal uses is constantly growing. Moringa preparations have been cited in the scientific literature as having antibiotic, antitrypanosomal, hypotensive, antispasmodic, antiulcer, antiinflammatory, hypocholesterolemic, and hypoglycemic activities (Adumu et al., 2017; Fahey, 2005).

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5.6 Moringa seeds oil

Moringa has been found to be a potential new source of oil especially with the advent of the need for oleo-chemicals and oils/fats derived fuels (biodiesel) all over the world (Anwar & Rashid, 2007; Ogbunugafor et al., 2011). In addition, cosmetics and medicinal uses are presented in several literature reports as mentioned above (Anwar & Bhanger, 2003; Anwar & Rashid, 2007; Farooq et al., 2012; Ruttarattanamonkol & Petrasch, 2015). From the health point of view, Moringa seeds oil has been used to treat various diseases because of its biological activities (see Table 5.9). Equally, Farooq et al. (2012) reported similar uses in the indigenous medicine. Unfortunately, many of these reports of efficacy in human beings are not supported by placebo controlled, randomized clinical trials, nor have they been published in high visibility journals (Fahey, 2005). For this reason, researchers has been focused the investigations in order to explain all of the excess of efficacy claims that have accumulated over the years. 5.6.4.1 Antimicrobial activity Like other medicinal plants, Moringa is studied to see its antimicrobial components (Fahey, 2005; Farooq et al., 2012). Some academics found that extraction of Moringa could reduce growth of Pseudomonas aeriginosa, Bascillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi (Bako et al., 2010). Furthermore, being a good source of flavonoids, poly phenol compounds and some chemical substances such as benzyl isothiocynate, and benzyl glucosinolate, which are other reasons for antimicrobial effects (Bako et al., 2010; Fahey, 2005). Other studies depicted that presence of antimicrobial peptides (AMPs) play role in lethality of Legionella, Streptococcus, and Staphylococcus species (Privalo et al., 2018). TABLE 5.9 Reported nutritional, therapeutic and prophylactic uses of Moringa oleifera seed oil (Amina et al., 2019; Fahey, 2005; Gilani et al., 1994). Traditional use

Condition/effect

Antimicrobial/Bioacidal

Fungal/Mycoses Thrush Skin (Dermal) Hypertension

Circulatory/Endocrine Detoxification Immunity

Antipyretic Purgative Lupus

Inflammation

Rheumatism

Nervous disorders

Hysteria

Nutritional

Antioxidant Energy Oil quality Prostate function

Reproductive health General (disorders/conditions)

Multiple Biological Activities of Unconventional Seed Oils

Bladder Gout Scurvy “Tonic”

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Ruttarattanamonkol and Petrasch (2015) studied the antimicrobial activities of M. oleifera seed and seed oil. The antibacterial activities of three different extracts: (1) cold water extract of M. oleifera seed powder, (2) cold water extract of M. oleifera residue after oil extraction by Soxhlet method, and (3) M. oleifera seed oil obtained by Soxhlet method were determined in vitro, using the diffusion technique of Bauer-Kirby and Minimal Inhibitory Concentration (MIC) method against selected pathogenic bacteria including Staphylococcus aureus, Bacillus subtilis, Salmonella typhimurium, Enterobactor aerogenes, Pseudomonas aerogonosa, and Escherichia coli (Ruttarattanamonkol & Petrasch, 2015). Different results were obtained from the experiments due to all M. oleifera extracts did not show visible suppression in growth of Bacillus subtilis, Salmonella typhimurium, Enterobactor aerogenes, Pseudomonas aerogonosa, and Escherichia coli. Particularly, the M. oleifera seed oil was not active against all bacterial strains tested. Similarly, Spiliotis (Spiliotis et al., 1997) investigated the antimicrobial activity of M. oleifera oil on several microorganisms and concluded that the oil was not effective against the microbial activity. However, Lalas (Lalas et al., 2012) evaluated the antimicrobial activity of M. Peregrina seed oil and proved the effective against all microorganisms studied. The variance in antimicrobial activity of Moringa seeds oil reported could be attributed to the differences in Moringa species and the oil extraction method used (Ruttarattanamonkol & Petrasch, 2015). Atieno et al. (2011) studied the antibacterial activity of methanol and n-hexane extracts of M. oleifera and M. stenopetala seeds. The experiments were conducted on three specific bacterial species (Salmonella typhii, Vibrio cholerae and Escherichia coli) which normally cause water borne diseases (producing gastroenteritis or inflammation of the stomach and intestinal lining). The highest inhibition values found occurred in the range reported by Mashiar (Mashiar et al., 2009) for the efficacy of a powder obtained from fresh M. oleifera leaves extracted using ethanol. This result suggests that extracts of Moringa seeds studied contain bio-compounds whose antibacterial potentials are comparable with that obtained from leaves. The results of this work demonstrate that both methanol and n-hexane extracts of M. oleifera and M. stenopetala displayed antimicrobial activity against Salmonella typhii. Folkard and Sutherland (Folkard & Sutherland, 2005) recommended utilization of Moringa seeds as food since it sterilizes the food and destroys Salmonella typhii which lives in the intestinal tracts of man. The antibiotic nature of Moringa seeds is due to an oil it contains which on consumption forms a thin film over the intestinal wall thus reducing or preventing the pathogen (by inhibition) from penetrating the walls (Ca´ceres & Lo´pez, 1991; Ca´ceres, & Cabrera, Morales, et al., 1991). The antibacterial activity has been demonstrated against gram-negative and gram-positive bacteria (Atieno et al., 2011). A similar investigation by Farooq et al. (2012) showed the antimicrobial activity of the aqueous methanolic extract and fixed oil from M. oleifera against microorganisms [Scenedesmus obliquus (green algae), Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus stearothermophilus (bacterial strains) and Herpes Simplex virus type 1 (HSV 1) and Polio virus type1 (sabin vaccine)]. Fluctuating degree of antimicrobial activity was observed ranging from sensitive for Bacillus stearothermophilus to resistant for Pseudomonas aeruginosa (Ali et al., 2004; Farooq et al., 2012). Amina et al. (2019) recently focused on the prospect of fabricating a polymeric naturally extracted M. oleifera oil bionano composite film enriched with silver nanoparticles for

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antimicrobial activity. Enhancing the antimicrobial effects of different oils is important for treating resistant infectious pathogenic microbes. Nowadays, nanoencapsulation (imbedding metal nanoparticles within polymer matrices) is a novel frontline technology in the field of nanoscience which, depending on the application, can be tailored to improve a number of desired properties. The antimicrobial activity experiments were performed using Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia, Salmonella typhii, Pseudomonas aeruginosa, Shigella flexneri, and Candida albicans stains (Amina et al., 2019). The M. oleifera oil and bionano composite showed varying degrees of antibacterial activities against the selected pathogens. The results demonstrate that bionano composite has a greater antibacterial activity over the M. oleifera seed oil. 5.6.4.2 Antifungal activity Many skin diseases, for example, tinea and ringworm caused by dermatophytes exist in tropical and semitropical zones. In general, these fungi live in the dead, top layer of skin cells in humid areas of the body, such as between the toes, the groin, and under the breasts. These fungal infections cause only a minor irritation. Other types of fungal infections can penetrate into the cells and cause itching, swelling, blistering, and scaling (Beentje). Many people in Taiwan or China have been using Moringa seeds as an herbal medicine to treat athlete’s foot and tinea achieving effective results. Chuang et al. (2007) reported for the first time, the evidence that extracts of M. oleifera have antifungal properties. The investigation was carried out to evaluate the antifungal activity of essential oil from Moringa leaves and extract from seeds against Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton Xoccosum, and Microsporum canis. The antifungal agent, ketoconazole, was used as the positive control. Both the results showed that essential oil has antifungal effects on Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton xoccosum and Microsporum canis. However, both leaf crude extract and subfractions had little effect on dermatophytes. The minimal inhibitory concentration (MIC) (0.156 mg/mL) of seed extract showed the strongest antifungal activity against Microsporum canis, a zoophilic dermatophyte causing marked inflammatory reactions in humans. Infected areas usually include human beard, hair, glabrous skin and hand (Chuang et al., 2007; Santos et al., 2015). It is very important to know about the cell lyses mechanisms of M. oleifera extracts on fungal cells so that further development of disease treatment can be conducted consequently (Chuang et al., 2007). Amina et al. (2019) also reported the fungicidal activity of M. oleifera oil and bionano composite against Candida albicans. The microscopic evaluation of some fungal and bacterial strains was carried out after treatment with seed extracts of M. oleifera (Jabeen et al., 2008) MIC values demonstrated that in bacterial species the most sensitive strains were Pasturella multocida and Bacillus subtilis. Staphlococcus aureus had moderate sensitivity and Escherichia coli was found to be comparatively least sensitive strain. Fusarium solani was more sensitive than Rhizopus solani, Aspergillus niger, and Metarhisium aniscoplae against the extract. Moreover, Rhizopus solani was selected for the microscopic evaluation of activities of seed extracts of M. oleifera due to comparatively rapid growth and least sensitivity. There was direct relation between concentration and damaging of the cell wall/ membrane of microorganism. A comparative effect of the different concentrations of protein extract of M. oleifera is demonstrated.

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It showed that high concentration of protein ruptured the cell wall of hyphea and damaged the conidia, and resulted in broken hyphea. Low concentrations of protein extract had less effect (Jabeen et al., 2008). 5.6.4.3 Antioxidant activity M. oleifera antioxidant activity is attributed to the presence of several types of antioxidant constituents. Related to the oil antioxidant potential, monopalmitic acid, oleic acid, tri-oleic triglycerides are the most significant compounds (Dhakad et al., 2019; Mahajan & Mehta, 2007). Baghel et al. (2012) reported that quercetin isolated from essential oil is quite compelling and can inhibit tumor necrosis factor by Kupffer cells. Moreover, the hydrocarbons of seed essential oil demonstrated radical scavenging effect (Mahajan & Mehta, 2007). Another study indicated a comparison among the antioxidant activity of M. oleifera seed powder, M. oleifera seed oil from Soxhlet method and its residue. The antioxidant activity was determined using 1,1-diphenyl-2- picrylhydrazy (DPPH) assay. The result confirmed that the M. oleifera seed oil possessed strongest antioxidant capacity, followed by M. oleifera seed and M. oleifera seed residue, respectively. The difference in antioxidant activities among samples can be attributed to tocopherol contents, the presence of phenolic compounds and the form of antioxidant compounds (hydrophilic and lipophilic) (NawirskaOlszan˜ska et al., 2013; Ruttarattanamonkol & Petrasch, 2015). In addition, Abd El Baky and El-Baroty, focused the investigation to evaluate the antioxidant, antibacterial and antiproliferation activity of M. peregrina seed oil against three cancer cell lines. The antioxidant activity of oil was assess with scavenging of DPPH, ABTS, superoxide (2O2),OH radicals and reducing power techniques (Abd El Baky & El-Baroty, 2013). Free radicals may cause reversible or irreversible damages to biological molecules such as deoxyribonucleic acid (DNA), proteins and/or lipids. These damages may cause cancer, heart diseases and arthritis, and could accelerate the aging of organisms (Bhatnagar & Gopala, 2013; Siger et al., 2008). Moringa oil showed a comparable high scavenging activity against (2O2) and OH radicals to that of standard antioxidants (BHT, BHA, and tocopherol content). However, these effects were dose-dependent, with concentration of 50% inhibition (IC50) values of 56.36 and 45.62 μg/mL, respectively. Moringa peregrina oil also revealed good scavenging abilities against DPPH and ABTS radicals with concentration dependent manner. The IC50 values were 25.65 and 95 μg/mL, respectively (Abd El Baky & El-Baroty, 2013). A similar study by Ogbunugafor (Ogbunugafor et al., 2011) comparing palm oil with M. oleifera seed oil for their antioxidant potential found out that Moringa oil are superiors for radical scavenging. The investigation reported that Moringa oil have remarkable physico-chemical and antioxidant properties which need to be explored for economic, nutritional and health applications. Bhatnagar and Gopala (2013) make a comparison between M. oleifera seed oil and commercially refined Groundnut oil for their natural antioxidants. Results demonstrated that M. oleifera oil was richer in bioactives such as tocopherols, phenolics, sterols, and carotenoids than Groundnut oil, showed significantly higher (P .05) percent inhibition of DPPH radicals. Since Moringa oil has a high amount of monounsaturated oleic acid and a very low quantity of polyunsaturated fatty acid (PUFA), it contains an excess of antiradical



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molecules (tocopherols, phenolics, and carotenoids) for preventing the peroxidation of its PUFA contents and quenching free radicals in the human body. Groundnut oil, being equally rich in PUFA and then may require most of its natural antioxidants for the prevention of peroxidation of its PUFA content. Instead, Moringa oil, being poor in PUFA, for this reason, have higher amounts of natural antioxidants at its disposal for quenching free radicals. This could be the reason for a higherIC50value of Moringa oil than Groundnut oil despite being poorer in tocopherols (Bhatnagar & Gopala, 2013). Taking into account the above-mentioned discussion, the consumption of Moringa oil could provide health benefits in terms of hypocholesterolemic effects (because of the presence of phytosterols) and scavenging of free radicals in the body (due to the presence of tocopherols, phenolics and carotenoids). 5.6.4.4 Antitubercular activity Tuberculosis (TB) remains one of the most common causes of ailment and mortality in humans, and it is estimated that approximately one-third of the world’s population has been infected with Mycobacterium tuberculosis (Gomez et al., 2005). TB is the number one infectious disease killer in the world, responsible for 1.5 million deaths in 2014 (Cadena et al., 2016). Adaptive T cell responses control but do not eradicate Mycobacterium tuberculosis in most healthy persons, resulting in a persistent mycobacterial infection that can expand and cause disease when T cell immunity fails (Gehring et al., 2020). Egharevba et al. (2015) studied the antitubercular activity and chemical composition of M. oleifera seed oil. Clinical Mycobacterium tuberculosis collected from Tuberculosis Research Unit of National Institute for Pharmaceutical Research and Development (NIPRD), Abuja, Nigeria was confirmed by Ziehl-Neelsen stain, grown on niacin media and arylsulphatase test which was positive after 14 days. Rifampicin was used as the standard antibiotic. Organism viability and media sterility control were also set up. The minimum concentration at which there was no growth of Mycobacterium was taken as the MIC. The result of antitubercular activity indicated that the oil was active against locally isolated strain of Mycobacterium tuberculosis at 25% (v/v), whereas that of the control drug, rifampicin, was 0.09 μg/mL (Egharevba et al., 2015). Many researchers reported the antibacterial activity of fatty acids and oily substances (Egharevba & Okwute, 2014; Orhan et al., 2011), particularly for oleic acid and its derivatives. Similarly, Esquivel (EsquivelFerrin˜o et al., 2014) attributed the antitubercular activity of the hexane extract of Citrus sinensis peel to the palmitic acid, decanal, caryophyllene oxide, and cis-limonene oxide contained in the extract. Other research reported the antitubercular activity of linoleic and oleic acid at 100 μg/mL (Esquivel-Ferrin˜o et al., 2012). Therefore the antitubercular activity of the seed oil of M. oleifera could be due to the oleic acid and palmitic acid content. Hypothetically the main place of action of fatty acids is the cell membrane where it interferes with the energy transport system by disrupting the electron transport chain and oxidative phosphorylation. Fatty acids membrane action might also inhibit enzyme activity, impair nutrient uptake, produce hazardous products of peroxidation and autooxidation and/or directly lyse bacterial cells (Debois & Smith, 2010). Certain investigation attributed fatty acid activity to the inhibition of oxygen uptake and stimulation of amino acid uptake into the cell (Orhan et al., 2011). Taking into account the above-mentioned

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information, M. oleifera oil could be exhibiting its actions through one or more of these mechanisms (Egharevba et al., 2015). 5.6.4.5 Anticancer activity Cancer is one of the most harmful diseases leading to human death in developing as well as developed countries. The number of cancer cases is estimated to increase by about 70% in 2035 (Elsayed et al., 2015; Ferlay et al., 2012). During the last 20 years, the use of plant products, has gained an increased interest in cancer therapy (El-Enshasy et al., 2013; Elsayed et al., 2014). Several compounds isolated from herbaceous medicinal plants were found to possess anticancer activities (Heo et al., 2014). Extracts isolated from different parts of medicinal plants revealed an inhibition of several cancer cells, for example breast, colon, lung, cervical, hepatocellular. Additionally, these plants and their extracts represented a good source for anticancer bioactive components now applied in clinical trials for cancer treatment (Elsayed et al., 2016). As above discussed, Moringa oil showed different biological activities. For this reason and because of the scarcity of anticancer studies on Moringa seeds oil, many researchers have been focused their work to explore the potential anticancer activity of the oil. Elsayed et al. (2016) assessed the anticancer properties of M. peregrina seed oil on different cell lines. The cell lines included: breast cancer (MCF-7); liver cancer (HepG2); colon cancer (CACO-2); cervical cancer (HeLa) and mouse fibroblasts (L929). Different concentrations (15
1000 μg/mL) of M. peregrina oil extracted from seed kernels were evaluated for their cytotoxic effect against cell lines. The obtained results indicated that M. peregrina seed oil has a significant cytotoxic effect on cell viability of all tested cell lines, and that the reduction in cell viability is proportional to the concentration applied. HepG2 and HeLa cells were the most affected, followed by MCF-7, CACO-2, and L929 cells. This can be explained from the cell types, which react differently to the administered doses based on the inherent differences found in their cell membrane structure and organization (Heo et al., 2014). The antiproliferative activities of M. peregrine seed oil may be attributable to the presence of different fatty acids, sterols and tocopherols. Moreover, Scheim (2009) studied the effect of different unsaturated fatty acids on several cancer cells, and found that they reduce tumor growth and cancer occurrence in living models. Monitoring cell morphology as affected by different concentrations of Moringa oil revealed that cells presented abnormal characteristics of cell morphology and started to detach from plate surfaces in response to the oil concentration. These alterations finally resulted in cell death (Elsayed et al., 2016). A similar study by the same author (Elsayed et al., 2015) also showed the antiproliferative properties of seed oil isolated from M. oleifera on different cell lines (HeLa, HepG2, MCF-7, CACO-2, and L929), and found that the largest toxic effect was obtained on HeLa cells. These cells exhibited the maximal decrease in cell viability, where oil treatment resulted in 76.1% inhibition of cell viability with an IC50 value of 422.8 μg/mL (Elsayed et al., 2015). Nibret and Wink (2010) investigated on the trypanocidal and antileukemic activities of the essential oils of H. abyssinica, L. ocymifolia, and M. stenopetala against Trypanosoma brucei bruceiand human leukemia cells, HL-60.M. stenopetala seed oil and its main

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compound, benzyl isothiocyanate presented the most potent trypanocidal activities withIC50values of 5.03 μg/mL and 1.20 g/mL, respectively (Seifu, 2014). This oil also showed cytotoxic activity against HL-60 cells with an IC50 of 11.63 g/mL. The oil components were also active against the human leukemia cells, HL-60. Benzylisothiocyanate (IC50 5 4.62 g/mL) was the most cytotoxic agent, followed by caryophyllene (IC50 5 19.31 g/mL) and cedrene (IC50 5 22.20 g/mL). The isothiocyanates are capable of forming covalent bonds with amino groups of amino acid residues (e.g., lysine and arginine) of proteins and also with primary amino groups of DNA bases that would result in protein and DNA alkylation (Nibret & Wink, 2010). Another study demonstrates the cytotoxic activity of M. stenopetala seed hexane extract against the HepG2 human hepatocellular cancer cells (Habtemariam, 2017). Abd El Baky and El Baroty evaluated the antiproliferation activities of M. peregrina seed oil in the term of cell death of three human cancer cells MCF-7, Hep-G2, and HCT-116. Among the three cell lines tested for cytotoxicity of Moringa oil, MCF7 was the most sensitive cell line followed by HeP-G2 and HCT-116. The antiproliferation activity of Moringa peregrina oil might be attributed to cytotoxic effect of nature of saturated and unsaturated fatty acids contained in the oil (Abd El Baky & El-Baroty, 2013).

5.7 Conclusion Moringa is health restorative plant and it is recognized in tropical and subtropical countries. The plant preparations have been cited in the scientific literature as having antibiotic, antitrypanosomal, hypotensive, antispasmodic, antiulcer, antiinflammatory, hypocholesterolemic, and hypoglycemic activities. The seeds and the leaves are the parts of the plant of interest because of the oil content and its biological activities. The seeds oil has several uses such as medicinal, cosmetics and potential for biodiesel production. Some biological activities such as antimicrobial, antifungal, antioxidant, antitubercular and anticancer demonstrated the real health potential of Moringa seeds oil.

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1358. Jacques, A. S., Arnaud, S. S., Fre´jus, O. H., & Jacques, D. T. (2020). Review on biological and immunomodulatory properties of Moringa oleifera in animal and human nutrition. Pharmacognosy and Phytotherapy, 12(1), 1
9. Lalas, S., Gortzi, O., Athanasiadis, V., Tsaknis, J., & Chinou, I. (2012). Determination of antimicrobial activity and resistance to oxidation of Moringa peregrina seed oil. Molecules (Basel, Switzerland), 17, 2330
2334. Lalas, S., Tsaknis, J., & Sflomos, K. (2003). Characterisation of Moringa stenopetala seed oil variety “Marigat” from island Kokwa. European Journal of Lipid Science and Technology, 105, 23
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Latif, S., & Anwar, F. (2008). Quality assessment of Moringa concanensis seed oil extracted through solvent and aqueous-enzymatic techniques. Grasas y Aceites, 59(1), 69
75. Leone, A., Spada, A., Battezzati, A., Schiraldi, A., Aristil, J., & Bertoli, S. (2015). Cultivation, genetic, ethnopharmacology, phytochemistry and pharmacology of Moringa oleifera leaves: An overview. International Journal of Molecular Sciences, 16, 12791
12835. Leone, A., Spada, A., Battezzati, A., Schiraldi, A., Aristil, J., & Bertoli, S. (2016). Moringa oleifera seeds and oil: Characteristics and uses for human health. International Journal of Molecular Sciences, 17, 1
14. Mahajan, S. G., & Mehta, A. A. (2007). Inhibitory action of ethanolic extract of seeds of Moringa oleifera Lam. on systemic and local anaphylaxis. Journal of Immunotoxicology, 4, 287
297. Manzoor, M., Anwar, F., Iqbal, T., & Bhanger, M. I. (2007). Physico-chemical characterization of Moringa concanensis seeds and seed oil. Journal of the American Oil Chemists’ Society, 84, 413
419. Marrufo, T., Nazarro, F., Mancini, E., Fratianni, F., Coppola, R., de Martino, L., Bela, A., & de Feo, V. (2013). Chemical composition and biological activity of the essential oil from leaves of Moringa oleifera Lam. cultivated in Mozambique. Molecules (Basel, Switzerland), 18, 10989
11000. Mashiar, M., Mominul, I., Sharma, A., Soriful, I., Atikur, R., Mizanur, R., & Alam, M. (2009). Antibacterial activity of leaf juice extracts of Moringa oleifera Lam. against some human pathogenic bacteria. Journal of Natural Sciences, 8, 219
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113. Middleton, E. J., Kandaswami, C., & Theoharides, T. C. (2000). The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease cancer. Pharmacological Reviews, 52, 673
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164. Mudasser, Z., Showkat, G., Surender, G., Surender, Y., Ranjana, S., & Sujata, G. (2015). Antifungal Efficacy of Moringa oleifera Lam. American Journal of Phytomedicine and Clinical Therapeutics, 3(1), 028
033. Nawirska-Olszan˜ska, A., Kita, A., Biesidia, A., Soko´l-Letowska, A., & Kucharska, A. Z. (2013). Characteristics of antioxidant activity and composition of pumpkin seed oils in 12 cultivars. Food Chemistry, 139, 155
161. Nibret, E., & Wink, M. (2010). Trypanocidal and antileukaemic effects of the essential oils of Hagenia abyssinica, Leonotis ocymifolia, Moringa stenopetala, and their main individual constituents. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 17, 911
920. Nogueira, R. S., Alencar, J., Santos, V., Collares, D., de Aguiar, R., de Souza, C. M., Neto, M., Feitosa, J. B., Costa, J. J., & Gadelha, M. F. (2017). Research advances on the multiple uses of Moringa oleifera: A sustainable alternative for socially neglected population. Asian Pacific Journal of Tropical Medicine, 10(7), 621
630. Odukoya, O. A., Jenkins, M. O., Ilori, O. O., & Sofidiya, M. O. (2005). The use of selected Nigerian natural products in management of environmentally induced skin damage. Pakistan Journal of Biological Sciences, 8, 1074
1077. Ogbunugafor, H. A., Eneh, F. U., Ozumba, A. N., Igwo-Ezikpe, M. N., Okpuzor, J., Igwilo, I. O., Adenekan, S. O., & Onyekwelu, O. A. (2011). Physico-chemical and antioxidant properties of Moringa oleifera seed oil. Pakistan Journal of Nutrition, 10(5), 4019
4414. Orhan, I., Ozc¸elik, B., & Sener, B. (2011). Evaluation of antibacterial, antifungal, antiviral, and antioxidant potentials of some edible oils and their fatty acid profiles. Turkish Journal of Biology, 35, 251
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C H A P T E R

6 Biological activities and antioxidant properties of Guizotia abyssinica (niger) seed oil W.K. Solomon and T.P. Nkambule Department of Food and Nutrition Sciences, Faculty of Consumer Sciences, University of Eswatini, Luyengo, Eswatini

Abbreviations DNF DPPH MUFA NPI PUFA RSA

defatted niger seed flour 1-diphenyl-2-picrylhydrazyl mono unsaturated fatty acid niger seed protein isolate polyunsaturated fatty acid radical scavenging activity

6.1 Introduction With increase in population worldwide and diversification of products where oil is an important ingredient, there is an increasing demand for edible oil. However, the edible oil market is dominated by few sources including sunflower, rape seed, and soyabean oil (Geleta et al., 2011). The ever-increasing demand for oil stimulated to opt for other underutilized and less familiar sources like niger seed (Guizotia abyssinica Cass.). Moreover, no particular oil was found versatile for all edible and nonedible uses owing to the variations in the composition and functional properties of oils from various sources (Ramadan, 2012). Niger seed (Guizotia abyssinica Cass.) is an oil seed crop found in Ethiopia and India where it is widely produced making the two countries the main producers in the world (Getinet & Sharma, 1996; Ramadan, 2012). It contributes about 50% and 3% oil seed production of Ethiopia and India, respectively (Dutta et al., 1994; Ramadan & Mo¨ersel, 2003; Sharma et al., 2020a, 2020b).

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00019-2

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© 2022 Elsevier Inc. All rights reserved.

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6. Biological activities and antioxidant properties of Guizotia abyssinica (niger) seed oil

Out of the six species of the genus Guizotia, five of those species including niger are of Ethiopian origin (Getinet & Sharma, 1996). The cultivation of Guizotia abyssinica in Ethiopiais largely for its edible oil which has a nutty taste and pleasant odor (Getinet & Sharma, 1996). It is the second oil seed in terms of production volume and the cultivated area next to sesame in Ethiopia (Geleta & Ortiz, 2013; Geleta et al., 2011). In India and other countries Guizotia abyssinica Cass. oil seeds are among the plant oils which are used frequently as a source of food, medicine apart from other usages such as in the preparation of soap, paint and other lubricants (Shashikala et al., 2018). Niger seed is a vital source of seed proteins, carbohydrates, vitamins, and fiber hence contributes to the human diet (Bhagaya & Sastry, 2003; Thatte & Lakshmi, 2012). The oil and other nutrient contents of niger seed vary depending on the extraction method, the origin, and the location where the crop was grown. The oil content of niger seed ranged from 28.3% to 50% (Bhagaya & Sastry, 2003; Bhatnagar & Gopalakrishna, 2014; Bhatnagar & Gopalakrishna, 2015; Dutta et al., 1994; Geleta et al., 2011; Ramadan & Mo¨ersel, 2003; Yadav, et al., 2012). Apart from being a good source of oil, niger seed is a good source of protein (Bhagaya & Sastry, 2003; Rao, 1994; Thatte & Lakshmi, 2012), vitamins, especially vitamin K1 (Bhatnagar & Gopalakrishna, 2015), and other nutrients (Bhagaya & Sastry, 2003; Deme et al., 2017; Rao, 1994). Besides its use as an edible oil, Guizotia abyssinica has been found to have health benefit which associated with the presence of phytochemical components, vitamin K1, high content of linoleic acid, vitamin E1, and other bioactives in the seed and the leaves (Ramadan, 2012; Rao, 1994; Yadav, et al., 2012).

6.2 Chemical composition and properties of Guizotia abyssinica seed The chemical composition of Guizotia abyssinica seed has been evaluated and reported by several researchers (Table 6.1). Variations in the chemical composition of the seed depends on the origin of the seed, growing location extraction methods: solvent extraction, cold or hot press and the type of solvent during chemical extraction (Bhatnagar & Gopalakrishna, 2014; Bhatnagar & Gopalanakrishna, 2013; Dutta et al., 1994; Marini et al., 2003; Ramadan & Mo¨ersel, 2003).

6.3 Fatty acid profile of Guizotia abyssinica oil The physical and chemical characteristics and the functional properties of fats are associated with the types and compositions of the fatty acids and the way in which these are positioned on the glycerol molecule. Several studies reported the lipid composition and free fatty acid profiles of Guizotia abyssinica seed oil (Bhatnagar & Gopalakrishna, 2015; Bhatnagar & Gopalanakrishna, 2013; Dutta et al., 1994; Marini et al., 2003; Ramadan & Mo¨ersel, 2003; Ramadan & Mo¨rsel, 2002). Table 6.2 shows the fatty acid profile of G. abyssinica seed oil reported in the literature. The fatty acid profile of G. abyssinica seed oil is similar with oils of the Compositae family linoleic acid being the major fatty acid. The composition of the fatty acids varies depending on the plant origin and extraction method (Bhatnagar & Gopalakrishna, 2014; Dutta

Multiple Biological Activities of Unconventional Seed Oils

TABLE 6.1 Chemical composition of niger seed and oil. Property

Value

References

Oil yield (g/100 g)

28.3
50

Dutta et al. (1994), Bhagaya and Sastry (2003), Ramadan and Mo¨ersel (2003), Geleta et al. (2011), Yadav, et al. (2012), Thatte and Lakshmi (2012), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014)

Protein (g/100 g)

24
30

Rao (1994), Bhagaya and Sastry (2003), Thatte and Lakshmi (2012)

Ash (g/100 g)

8.1
9.9

Rao (1994), Bhagaya and Sastry (2003), Thatte and Lakshmi (2012)

Crude fiber (g/100 g)

9.0
21.8

Rao (1994), Bhagaya and Sastry (2003), Thatte and Lakshmi (2012)

Moisture content

4.5

Bhagaya and Sastry (2003)

Peroxide value (mequivO2/kg oil)

0.22
7.8

Ramadan and Mo¨ersel (2003), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014), Atinafu et al. (2015)

Iodine value (I2/g oil)

41.6
140.3

Ramadan and Mo¨ersel (2003), Yadav, et al. (2012), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014)

Saponification value (mg KOH/g oil)

16.27
200.16 Dutta et al. (1994), Ramadan and Mo¨ersel (2003), Yadav, et al. (2012), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014), Atinafu et al. (2015)

Unsaponifiable matter

1.21
3.97

Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2015)

% Saturated fatty acids (S)

14.6
17.7

Bhatnagar and Gopalanakrishna (2013)

% Monounsaturated fatty acids (M)

12.2
14.0

Bhatnagar and Gopalanakrishna (2013)

% Polyunsaturated fatty 68.4
73.2 acids (P)

Bhatnagar and Gopalanakrishna (2013)

TABLE 6.2 Fatty acid profile of Guizotia abyssinica oil from different origin. Fatty acid

Value (g/ 100 g)

References

Palmitic acid (C 6.4
17.0 16:0)

Dutta et al. (1994), Rao (1994), Marini et al. (2003), Ramadan and Mo¨ersel (2003), Ramadan et al. (2003), Geleta et al. (2011), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014), Bhatnagar and Gopalakrishna (2015)

Stearic acid (C 18:0)

4.5
8.9

Dutta et al. (1994), Marini et al. (2003), Ramadan and Mo¨ersel (2003), Ramadan et al. (2003), Geleta et al. (2011), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014)

Oleic acid (C 18:1)

7.52
53.03

Rao (1994), Marini et al. (2003), Ramadan and Mo¨ersel (2003), Ramadan et al. (2003), Geleta et al. (2011), Yadav, et al. (2012), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014)

Linoleic acid (C 32.03
77.5 18:2)

Rao (1994), Marini et al. (2003), Ramadan and Mo¨ersel (2003), Ramadan et al. (2003), Geleta et al. (2011), Yadav, et al. (2012), Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2014)

Linolenic acid (C18:3)

0.1
0.35

Dutta et al. (1994), Rao (1994), Ramadan and Mo¨rsel (2002), Marini et al. (2003)

Behenic acid (C22:0)

0.2
0.9

Ramadan and Mo¨rsel (2002), Marini et al. (2003), Ramadan and Mo¨ersel (2003), Bhatnagar and Gopalanakrishna (2013)

80

6. Biological activities and antioxidant properties of Guizotia abyssinica (niger) seed oil

et al., 1994; Ramadan & Mo¨rsel, 2002). The major fatty acid in G. abyssinica seed oil was reported to be linoleic acid (C 18:2) (Bhatnagar & Gopalakrishna, 2014; Dutta et al., 1994; Marini et al., 2003; Quequeto, et al., 2020). The other predominant fatty acids reported are palmitic acid (C 16:0), oleic acid (C 18:1), and stearic acid (C 18:0) (Dutta et al., 1994; Marini et al., 2003; Ramadan & Mo¨ersel, 2003). The palmitic acid was the major saturated fatty acid followed by the stearic acid. This trend has been consistent in both Ethiopian and Indian varieties (Marini et al., 2003; Ramadan & Mo¨ersel, 2003; Ramadan & Mo¨rsel, 2002). Other fatty acids have been reported in less amounts for different regions of Ethiopia and India (Table 6.2). Other fatty acids including arachidic (C20:0), linolenic (C18:3), behenic (22:0), tricosanoic (C23:0), eicosapentaenoic (C20:5), and lignoceric (C24:0) are also present (Bhavsar et al., 2017; Dutta et al., 1994; Ramadan & Mo¨rsel, 2002; Rao, 1994).

6.4 Phytochemicals in Guizotia. abyssinica Phytochemicals are defined as nonnutritive plants chemicals that have important properties either defensive or disease protective. These are mainly produced by plants to provide them with protection. They are generally described as phytoestrogens, terpenoids, carotenoids, isoflavonoids and anthocyanidins. Even though they are considered nonessential nutrients, their dietary intake may have a lot of health benefits. These involve protection against degenerative disorders like cancer, cardiovascular and neurodegenerative diseases (Prakash et al., 2012). The pharmaceutical importance of these plants depends on the chemical substances that yield a certain physiological action on the human body. Alkaloids, tannins, flavonoids, and phenolic compounds have been identified as the most important bioactive constituents (Edeoga et al., 2005). Phytochemicals are present in many important plant items including whole grains, beans, fruits, vegetables, and herbs (Prakash et al., 2012). A phytochemical screening conducted revealed that ethanol extracts of G. abyssinica seeds contain tannins, terpenoids, alkaloids, flavonoids, cardiac glycosides, and steroids (Amin et al., 2019; Sharma et al., 2020a, 2020b; Shashikala et al., 2018). A quantitative estimation of phytochemicals in dried G. abyssinica seeds showed alkaloids, flavonoids, phenols, saponins and tannins to be 20.75 6 0.23, 51.75 6 0.35, 30.85 6 0.61, 19.65 6 0.26, and 17.45 6 0.27 mg/g, respectively. However, the yield of phytochemicals in the seed are dependent on the type of solvent used for extraction (Sharma et al., 2020a, 2020b). Ethanolic extracts of G. abyssinica leaf also presented phytochemicals including alkaloids, glycosides, phenols, flavonoids, and tannins (Hirvey et al., 2020).

6.5 Bioactivities of Guizotia abyssinica seed Several bioactive components have been reported to be present in niger seed including sterols, tocopherols, phenolic compounds, vitamin K1, and carotenoids. The bioactive components of niger seed extracted using different media has also been reported (Bhatnagar & Gopalanakrishna, 2013).

Multiple Biological Activities of Unconventional Seed Oils

6.5 Bioactivities of Guizotia abyssinica seed

81

TABLE 6.3 Types of tocopherols in Guizotia abyssinica. Type of tocopherol

Value (ppm)

References

α-Tocopherol

154.2
861 Bhatnagar and Gopalanakrishna (2013), Bhatnagar and Gopalakrishna (2015), Ramadan and Mo¨rsel (2002), Ramadan and Mo¨ersel (2003)

β-Tocopherol

276
331

Ramadan and Mo¨rsel (2002), Ramadan and Mo¨ersel (2003)

γ-Tocopherol

510
570

Ramadan and Mo¨rsel (2002), Ramadan and Mo¨ersel (2003)

δ-Tocopherol

9.9
185

Ramadan and Mo¨rsel (2002), Ramadan and Mo¨ersel (2003), Bhatnagar and Gopalanakrishna (2013)

6.5.1 Tocopherols Tocopherols are natural antioxidants and integral bioactive molecules of an oil or fat and act as antioxidants. The amount of total tocopherol content depends on the extraction medium/solvent used (Bhatnagar & Gopalanakrishna, 2013; Ramadan & Mo¨rsel, 2002). The total tocopherol of niger seed crude oil extracted using hexane was reported to be 1947 ppm of which α-tocopherol was 861 ppm (Ramadan & Mo¨ersel, 2003; Ramadan & Mo¨ersel, 2004). Niger seed oil extracted using chloroform methanol was reported to have total tocopherol of 1772 ppm of which the α-tocopherol was 756 ppm (Ramadan & Mo¨rsel, 2002). Tocopherol content ranging from 660 to 850 μg/g oil of niger seed oil of Ethiopian origin extracted using heptane/isopropanol (3:2, v/v) has also been reported (Dutta et al., 1994). whereas total tocopherol values ranging from 171.9 to 345.8 ppm from niger seed oil extracted using solvents with different polarity were reported (Bhatnagar & Gopalanakrishna, 2013). The total tocopherol in niger seed oil was reported to be 345.8 with α-tocopherol being 276.3 ppm, whereas in the niger seed cake it was found to be 405.5 ppm of which α-tocopherol was 324.9 ppm (Bhatnagar & Gopalakrishna, 2015). The different levels of individual tocopherols reported in literature are presented in Table 6.3.

6.5.2 Total phenolics Phenolic compounds are known to be the largest class of secondary metabolites in plants (Cheynier, 2012) which consist of a range of plant substances that commonly contain an aromatic ring bearing one or more hydroxyl substituent all of which carry out a variety of physiological functions in plants (Lattanzio, 2013). The phenolic compounds have a variety of structures of which the flavonoids form the largest group although they are classified as monocyclic phenols (Ruiz & Romero, 2001). Flavonoids are present in many plant organs and over 8000 different flavonoids have been reported (Lattanzio, 2013; Martı´nez-Valverde et al., 2000). Other phenolics that are present in the moderate amounts are phenylpropanoids and phenolic quinones. There are other important groups of polyphenolic and occasional phenolic units (such as lignins, melanins, and tannins) that are found in proteins, alkaloids, and terpenoids (Brielmann et al., 2006). The main function of plant phenolics is the defense mechanisms they are considered to possess against

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6. Biological activities and antioxidant properties of Guizotia abyssinica (niger) seed oil

environmental stresses including pathogen infection, low temperatures, high light, herbivores and nutrient deficiency (Lattanzio, 2013). There has been an increasing interest in phenolic compounds as they are found to be linked with the inhibition of atherosclerosis and cancer. The biological activity of phenolics is suspected to be associated with their antioxidant activity. The antioxidant activity is attributed to their ability to chelate metals, inhibit lipoxygenase and scavenge free radicals (Martı´nez-Valverde et al., 2000). Niger seeds are found to be good source of phenols. Total phenol content of 646.7 and 630 mg/100 g of defatted niger seed flour was reported for aqueous and ethanol extracted, respectively. Similarly, total phenol content of 1110 and 926.67 mg/100 g of niger seed protein isolate for aqueous and ethanol extracted was reported, respectively (Thatte & Lakshmi, 2012). The total phenolics in niger seed oil ranged from 247 to 2264.7 ppm depending on the extraction method (Bhatnagar & Gopalanakrishna, 2013). Total phenolics content of 2266.2 ppm was reported for niger seed oil whereas the total phenolics for niger seed cake was found to be 2545.5 ppm (Bhatnagar & Gopalakrishna, 2015). Low level of phenolic compound 5 ppm (5 mg/kg) has also been reported (Bhatnagar & Gopalanakrishna, 2013).

6.5.3 Total sterols Sterols are natural compounds which belong to the isoprenoid class having varied and important processes taking place in plants including regulating the growth and development and stress resistance. They contribute to sustaining their permeability and fluidity in combination with glycerolipids and spingolipids (Piironen, et al., 2000; Rogowska & Szakiel, 2020) even though some plant sterols have been reported to have specific function in signal transduction (Piironen, et al., 2000). Plant sterols that are commonly consumed are sitosterol, stigmasterol and campesterol and these are mainly found in vegetable oils. These oils are said to be a good sources of the steryl esters. Sterols are considered nutritionally important in human health due to their similarity in structure with cholesterol, and are capable of lowering plasma cholesterol and low-density lipoproteins (LDL) cholesterol (Piironen, et al., 2000). The total sterols in niger seed oil have been reported to range from 1249.6 to 6309.3 ppm. The β-sitosterol, campesterol, stigmasterol, Δ5-avenasterol and Δ7-avenasterol were among the main components where the β-Sitosterol appeared to be the predominant (Bhatnagar & Gopalakrishna, 2015; Dutta et al., 1994; Marini et al., 2003; Ramadan & Mo¨rsel, 2002).

6.5.4 Total carotenoids Carotenoids are an important group of phytochemicals that have been reported to be responsible for the diverse colors of the foods. They are known to have a significant role in disease prevention and keeping stable health. Apart from being a strong antioxidant some carotenoids have been reported to contribute to dietary vitamin A. There has been some research that support the positive role of phytochemicals in the prevention of numerous chronic diseases such as cancer, cardiovascular disease, osteoporosis and

Multiple Biological Activities of Unconventional Seed Oils

6.6 Effect of extraction solvent on bioactive composition and antioxidant activity

83

diabetes (Rao & Rao, 2007). The total carotenoids in niger seed oil extracted using ethanol ranges from 18.9 to 181 ppm (Bhatnagar & Gopalakrishna, 2015; Bhatnagar & Gopalanakrishna, 2013). Higher carotenoid values (702 ppm) have also been reported (Ramadan & Mo¨ersel, 2004). Niger seed oil cake was reported to contain 301.16 ppm (Bhatnagar & Gopalakrishna, 2015). The studies above displayed that the total bioactive extracted increase with the increase in the polarity of the extraction solvents.

6.5.5 Vitamin K1 Vitamin K1 also known to be phylloquinone is present in varied levels in different foods (Booth et al., 1993). It is known as an aspect essential for normal blood coagulation It has also been recently gaining recognition in relation to its role in bone metabolism (Bu¨gel, 2003). Available data has displayed that leafy, green vegetables, and some legumes and vegetable oils are good dietary sources of vitamin K1 (Booth et al., 1993). Niger seed is a good source of vitamin K1 and its concentration in oil depends on the oil extraction method applied where solvent extraction results in maximum vitamin K1. Niger seed oil and niger seed cake were reported to have 1689.5 and 3225.3 ppm, respectively of vitamin K1 compared to 130 ppm in soyabean oil, 150 ppm in rape seed oil and 10 ppm in sunflower oil (Bhatnagar & Gopalakrishna, 2015).

6.6 Effect of extraction solvent on bioactive composition and antioxidant activity Extraction of plant material is regarded as a sample preparation technique and it plays a crucial role in successful analysis of bioactive compounds of plant parts (Azmir & Zaidul, 2013). Solvent extraction (liquid
liquid or solid
liquid extraction) is one of the traditional methods used to extract natural bioactive compounds from plants among other things. Other methods used include pressurized-liquid extraction, subcritical and supercritical extractions, and microwave- and ultrasound-assisted extractions (Joana GilCha´vez, et al., 2013). The niger seed oil extraction using various solvents or solvents of different polarity result in different oil quality and different concentrations of bioactives. The biological activity of plant extracts is mainly dependent on the extraction solvent and to some extent the drying method (Nkambule, 2017). Many researchers have used varied solvent systems for the successful extraction of bioactive compounds and antioxidants in seed oils. The effectiveness of different solvent systems to make niger seeds extracts was evaluated (Shahidi et al., 2003). In this study, the solvent systems used were 80:20 (vol/ vol) ethanol/water, 80:20 (vol/vol) acetone/water, and water. The results from this study revealed similar yields from 80:20 (vol/vol) ethanol/water and 80:20 (vol/vol) acetone/ water and lower from water. From the same yields, the antioxidant activity using the β-carotene
linoleate model system displayed that water extracts had lower (and different) antioxidant activity compared to the other solvent extracts. This study concluded in general that the 80:20 (vol/vol) ethanol/water extracts were superior particularly during prolonged periods. The effect of extraction solvent on the bioactive composition of niger seed

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of Indian origin was reported (Bhatnagar & Gopalanakrishna, 2013). The result indicated that the bioactive contents (total tocopherols, sterols, and carotenoids) significantly (P , .05) increased with the polarity of the extraction solvents and ethanol was found be the best solvent among those compared. Another study used hexane, petroleum ether, methanol, chloroform, chloroform: methanol (2:1), and water in phytochemical screening of Guizotia abyssinica. Results of the study were varied in phytochemicals such as alkaloids, flavonoids, and steroids with methanol extracts displaying the highest presence of phytochemicals (Baghel & Bansal, 2015). The type of solvents used also affects oxidative stability and radical scavenging activity. Moreover, important parameters like peroxide value and unsaponifiable matter that have a bearing on the oxidative radical scavenging activity were found to be affected by the solvent used for extraction of oil (Bhatnagar & Gopalakrishna, 2014; Bhatnagar & Gopalakrishna, 2015; Bhatnagar & Gopalanakrishna, 2013; Thatte & Lakshmi, 2012). The extraction solvent was also reported to significantly influence the concentration of bioactive compounds and %DPPH inhibition from essential oils. Thus, in characterizing and comparing the antioxidant activities and contents bioactives of oils and by-products, it is necessary to take into account the extraction method used.

6.7 Biological activities of Guizotia abyssinica 6.7.1 Antimicrobial activity of Guizotia abyssinica seed The use of plant oils and extracts for its antimicrobial activity has been documented for many years hence the antimicrobial activity of plants has been applied in many processes such as food preservation, pharmaceuticals, and substitute medicine (Hammer et al., 1999). Medicinal plants signify a good source of antimicrobial agents as they possess diverse medicinal properties hence, they have an excessive potential to be used as antibacterial and antifungal agents (Kalaivani, et al., 2012). The authors further reported that antibacterial and antibacterial activity differs with the species of the plant and plant material used. The essential oils from plants are active against a varied range of pathogens due to different types of aldehydes, phenolics, terpenes, and other antimicrobial compounds present. The functional group’s orientation, nature, and composition influence the responsiveness of essential oil (Swamy et al., 2016). The ethanolic and aqueous extracts of G. abyssinica exhibited antimicrobial effects on some species of bacteria (Amin et al., 2019; Dwivedi et al., 2015). Ethanolic extracts from G. abyssinica seeds exhibited inhibition against Staphylococcus aureus (ATCC 6538), Salmonella abony (ATCC 6017), Escherichia coli (ATCC 8739), Pseudomonas aeruginosa (ATCC 9027) by the agar well diffusion method (Amin et al., 2019). The inhibition zones for the different microorganisms were 12, 8, 14, 14, and 10 mm for B. subtilis, S. aureus, S. abony, E. coli, and P. aeruginosa, respectively. The maximum zone of inhibition was observed against S. abony and E. coli. The antimicrobial activity of aqueous and ethanolic extracts of G. abyssinica flower was evaluated against Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, and Staphylococcus aureus (Dwivedi et al., 2015). The result indicated a dose-dependent inhibition (Table 6.4). The percentage of relative inhibition zone using

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6.7 Biological activities of Guizotia abyssinica

TABLE 6.4 Antimicrobial activity of Guizotia abyssinica (L.f.) Cass. Treatment

Concentration (μg/mL)

EEGAF

SD

S. abony

E. faecalis













10













20

4.23 6 0.30

40

6.14 6 0.13

10.29 6 0.31

8.06 6 0.11

8.01 6 0.11

60

12.80 6 0.13

15.39 6 0.20

14.2 6 0.21

11.03 6 0.46

10













20

5.5 6 0.27

6.6 6 0.22

4.14 6 0.13

3.5 6 0.20

40

8.32 6 0.14

11.15 6 0.23

7.49 6 0.12

6.80 6 0.39

60

12.80 6 0.16

12.66 6 0.14

13.29 6 0.31

12.61 6 0.39

60

22.5 6 0.76 (a)

24.16 6 0.72 (a)

25.16 6 0.72 (b)

19.5 6 0.28 (b)

Control AEGAF

Zone of Inhibition (mm) E. coli P. aeruginosa

(a) Cefitaxime, (b) amoxicillin. AEGAL, Aqueous extract of Guizotia abyssinica flower; EEGAL, ethanolic extract of Guizotia abyssinica flower; EC, Escherichia coli; PA, Pseudomonas aeruginosa; EF, Enterococcus faecalis; SA, Staphylococcus aureus, control Dimethyl sulfoxide (DMSO); SD, standard deviation. Source: Dwivedi, S., Attitala, H.I. & Elmhdwi, M., 2015. Anti-microbial screening of aqueous and ethanolic extract of flower of Guizotia abyssinica (L.F.) Cass. International Journal of Pharmacy and Life Sciences, 6(6), pp. 4570
4572.

aqueous extract in relation to the standard at 60 μg/mL for E. coli, P. aeruginosa, S. abony, and E. faecalis was 52%, 59%, 57%, and 57%, respectively, using aqueous extract. Similarly, the relative inhibition zone compared to the standard using ethanol extract was 57%, 56%, 52%, and 59% for E. coli, P. aeruginosa, S. abony, and E. faecalis, respectively.

6.7.2 Antifungal activities of Guizotia abyssinica seed The ethanolic extracts from G. abyssinica seeds were tested for antifungal activity against pathogenic fungi including Alternaria solani, Lasiodiploidia theobromae, Rhizopus spp., and Aspergillus Niger, causing infection in many plants. The inhibition zones for Aspergilus niger, Lasiodiploidia theobromae, and Rhizopus spp. were 74, 16, and 16 mm, respectively. The ethanolic extracts from G. abyssinica seeds were most effective against Aspergilus niger. The extract exhibited no inhibition to Alternaria solani (Amin et al., 2019).

6.7.3 Anticancer activity of Guizotia abyssinica seed It has been established that plants are origins of many bioactives of medicinal and industrial significance. Many researchers have shown that Guizotia abyssinica is a source of phytochemicals and antioxidant potential. Often times a plant with such properties may have the potential for anticancer properties (Jang, et al., 2012). Ethanolic extracts of Guizotia abyssinica seed displayed a remarkable cytotoxic effect against mouse, muscle, and human embryonic kidney cell lines. The results displayed minimum effectiveness at a

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6. Biological activities and antioxidant properties of Guizotia abyssinica (niger) seed oil

lower concentrations which increased with an increase in the concentration of the extracts (Amin et al., 2019).

6.7.4 Antiinflammatory activity of Guizotia abyssinica seed The study of plants in the use as antiinflammation is still ongoing in an effort to obtain new antiinflammatory drugs. It is believed that many medicinal plants contain a wide range of compounds from which antiinflammatory agents can be explored (Padmanabhan & Jangle, 2012). The antiinflammatory effects of an extract of leaves and seeds extracts of Guizotia abyssinica have been studied in rats (Dwivedi et al., 2014). The result from this study showed that the extract has substantial antiinflammatory activity in rats. The water G. abyssinica leaf extract at the test dose of 100 and 200 mg/kg body weight decreased the edema initiated by carrageenan by 42.68% and 47.56%, respectively whereas the ethanol extract of G. abyssinica leaf extract at the test dose of 100 and 200 mg/kg body weight decreased the edema initiated by carrageenan by 42.68% and 47.56%, respectively. Similarly, the aqueous G. abyssinica seed extract decreased the edema initiated by carrageenan by 47.56% and 53.04%, at the test dose of 100 and 200 mg/kg body weight, respectively, whereas the ethanol G. abyssinica seed extract decreased the edema initiated by carrageenan by 37.19% and 45.73% at the test dose of 100 and 200 mg/kg body weight, respectively. The inhibition of the standard drug was 63.14%. In view of the side effects of synthetic drugs coupled with the relatively minimal side effects of plant extracts, it is important to establish and find out the efficiency of plants against antiinflammation so as to harness their benefit as natural products (Dwivedi et al., 2014).

6.7.5 Antioxidant activity of Guizotia abyssinica Antioxidants from natural sources are gaining interest due to consumers’ preference for healthy and natural ingredients coupled with the toxicity of synthetic antioxidants. Lipid oxidation adversely affects the physicochemical, sensory attributes, and nutritional value of foods during storage which in turn limits the utilization of oil in food manufacturing as fortificant and bioactives in functional foods. Most of the methods of determination of total antioxidant activity characterize the ability of the tested compound to scavenge free radicals and/or to complex metal ions driving the oxidation process. Previous studies highlighted that the antioxidant potency tested are done in two ways: using assays for radical scavenging ability and assays that test the ability to inhibit lipid oxidation under accelerated conditions (Ramadan & Mo¨ersel, 2004; Ramadan et al., 2003). Studies also emphasized the difference between “antiradical” and “antioxidant” activity and that they do not exactly occur simultaneously where antiradical activity specify the potential of compounds to react with free radicals (in a single free radical reaction), but antioxidant activity constitutes the ability to hinder the process of oxidation which in the case of lipids, entail a set of various reactions (Tirzitis & Bartosz, 2010). Studies have shown that the bioactives in crude and refined niger seed oil exhibited an antioxidant property where crude oils exhibited better stability than their counterparts (Ramadan & Mo¨ersel, 2006; Ramadan et al., 2003; Sharma et al., 2020a, 2020b). The

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87

antiradical properties of niger seed crude oil were assessed by using two different stable free radicals 1,1-diphenyl-2-picrylhydrazyl (DPPH) and glavinoxyl. The result indicated that, after 1 hour of incubation 14.0% of DPPH radicals and 12.8% of glavinoxyl radicals were quenched by niger seed crude oil. The percentage quenched was less than other crude oils like black cumin and coriander crude oils (Ramadan et al., 2003). Niger seed has relatively higher composition of polyunsaturated fatty acids (PUFA) (Bhatnagar & Gopalakrishna, 2014; Bhatnagar & Gopalakrishna, 2015; Bhatnagar & Gopalanakrishna, 2013) making the oil sensitive to oxidative deterioration. The relatively low radical scavenging activity (RSA) compared to other oils is attributed to the high level of PUFA (Ramadan et al., 2003). Though there is a high concentration of α-tocopherol in niger seed compared to black cumin and coriander the RSA might have been overcome by the PUFAformed radicals and other factors including initial high peroxide value and level of polar lipids. The phospholipid fraction of niger seed oil quenched 62.2% of glavinoxyl radicals. Niger seed oil contained much higher levels of tocopherol (171.9
1947 μg tocopherol/g oil) than black cumin, coriander, sunflower, and safflower oils, which gives great stability against oxidation despite substantial linoleic acid composition (Dutta et al., 1994; Ramadan, 2012). Niger seed oil and cake are reported to have significantly higher RSA than sunflower oil. Niger seed oil and cake exhibited 42% and 55% inhibition in the first minute of incubation against DPPH whereas sunflower seed oil exhibited 15% inhibition (Bhatnagar & Gopalakrishna, 2015). The IC50 values (sample concentrations causing 50% reduction in the total amount of DPPH radicals) of niger seed cake and niger seed oil appeared to be 5.7 mg/mL and 9.2 mg/mL, respectively (Bhatnagar & Gopalakrishna, 2015). High values of tocopherols, phenolics, vitamin K1, phytosterols, and carotenoids are responsible for the radical scavenging activities of niger seed oil and cake. The antioxidant activity of defatted niger seed flour (DNF) and niger seed protein isolate (NPI) was found to be promising (Thatte & Lakshmi, 2012). NPI showed a substantially lower IC50 value indicating a better free RSA. Niger seed exhibited by far greater DPPH activity than rape seed protein concentrate (IC50 34.3 mg mL) and pumpkin seed protein isolate (IC50 0.1 g mL). Hydroxyl radical is most reactive and when produced during oxidation can seriously destroy biomolecules causing the commencement of some diseases like cancer and atherosclerosis. NPI and DNF also exhibited equivalent IC50 values suggesting comparable hydroxyl radical scavenging capacity (Thatte & Lakshmi, 2012). Methanolic and aqueous extracts of DNF showed better total antioxidant activity compared to NPI. Defatted niger seed crude extracts using different solvents (acetone/water, alcohol/ water, and water) exhibited antioxidant activity which was superior or equal to tocopherols but lower than commonly used synthetic antioxidants. The ethanol/water (80:20 vol/ vol) extracts of Niger (Guizotia abyssinica) seed displayed high antioxidant activity in a β-carotene-linoleate and a meat model system. The chlorogenic acid-related compound was major component present based on column chromatography and HPLC analysis and responsible for the antioxidant activity (Shahidi et al., 2003). The oxidative stability of crude and stripped niger seed oil was studied under accelerated oxidation conditions. Crude niger seed oil showed better oxidative stability than stripped (removed polar compounds) oil. The concentration of unsaponifiable which has an antioxidant property was

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6. Biological activities and antioxidant properties of Guizotia abyssinica (niger) seed oil

reported to be 10.1 g/kg compared to black cumin (14.9 g/kg) and coriander (21.8 g/kg). Moreover, the concentration of tocopherols was higher than black cumin and coriander seed oils (Ramadan & Mo¨ersel, 2004). The fact that crude oil has better oxidative stability suggest that crude niger seed oil has potent antioxidant compounds.

6.8 Other biological activities A recent study has reported antidiabetic potential of ethanolic extract of Guizotia abyssinica leaf in diabetic rats. This study reported that oral treatment of these extracts at 200 and 400 mg/kg doses significantly decreased glucose levels in diabetic rat (Hirvey et al., 2020).

6.9 Conclusion Guizotia abyssinica is a good source of oil with oil yield ranging from 28 to 50%. Linoleic acid (C 18:2) is the main fatty acid thus making G. abyssinica nutritionally valuable and attractive. The presence of phytochemicals is an indicative of its health application. The multiple biological activities and antioxidant properties exhibited by G. abyssinica strongly suggest its potential for many industrial applications.

References Amin, N., Parmar, K., Patel, V., & Kottayi, M. (2019). Evaluation of medicinal constituents and properties of Linum usitatissimum, Prosopis juliflora and Guizotia abyssinica. Journal of Pharmacognosy and Ohytochemistry, 8(4), 2238
2244. Atinafu, D. G., Shamshad, K. B., & Libsu, S. (2015). Quality characterization of Niger seed oil (Guizotia abyssinica Cass.) produced in Amhara regional state, Ethiopia. AfricanJournal of Biotechnology, 14(3), 171
174. Azmir, J., Zaidul, I. S. M., et al. (2013). Techniques for extraction of bioactive compounds from plant materials: A review. Journal of Food Engineeing, 117(4), 426
436. Baghel, S., & Bansal, Y. K. (2015). Thidiazuron promotes in vitro plant regeneration and phytochemical screening of Guizotia abyssinica Cass. -a multipurpose oil crop. World Journal of Pharmacy and Phamaceutical Sciences, 4(1), 1193
1217. Bhagaya, S., & Sastry, S. (2003). Chemical, functional and nutritional properties of wet dehulled niger. LWT - Food Science and Technology, 36, 703
708. Bhatnagar, A. S., & Gopalanakrishna, A. G. (2013). Effect of extraction solvent on oil and bioactives composition of commercial Indian niger (Guizotia abyssinica (L.f.) Cass.). Journal of American Oil Chemical Society, 90, 1203
1212. Bhatnagar, A. S., & Gopalakrishna, A. G. (2014). Lipid alsses and subclasses of cold-pressed and solvent extracted oils from commercial Indian niger (Guizotia abyssinica (L.f) Cass). seed. Journal of the American Oil Chemists Society,, 91, 1205
1216.. Bhatnagar, A. S., & Gopalakrishna, A. G. (2015). Bioactives concentrate from commercial Indian niger (Guizotia sbyssinica (Lf) Cass.) seed and its antioxidant and antiradical activity. American Journal of Nutrition and Food Science, 1(1), 10
20. Bhavsar, G. J., Syed, H. M., & Andhale, R. R. (2017). Characterization and quality assessement of mechanically and solvent extracted niger (Guizotia abyssinica). Journal of Pharmacognosy and Phytochemistry, 6(2), 17
21. Booth, S. L., Sadowski, J. A., Weihrauch, J. L., & Ferland, G. (1993). Vitamin K1 (phylloquinone) content of foods: A provisional table. Journal of Food Composition and Analysis, 6(2), 109
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18. Nkambule, T. (2017). Evaluation of Momordica balsamina and Momordica foetida from Swaziland for their antimicrobial activity, anti-proliferative properties and biochemical composition (Doctoral dissertation. University of Nottingham, s.l. Padmanabhan, P., & Jangle, S. N. (2012). Evaluation of in-vitro anti-inflammatory activity of herbal preparation, a combination of four medicinal plants. International Journal of Basic and Applied Medical Sciences, 2(1), 109
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Ramadan, M. F., Kroh, L. W., & Mo¨ersel, J.-T. (2003). Radical scavenging activity of black cumin (Nigella sativa L.), coriander (coriandrum L.) and niger (Guizotia abyssinica Cass.) crude seed oils and oil fractions. Journal of Agricultural and Food Chemistry, 51, 6961
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276. Ramadan, M. F., & Mo¨ersel, J.-T. (2004). Oxidative stability of black cumin (Coriandrum sativum) and niger (Guizotia abyssinica Cass.) crude seed oils upon stripping. European Journal of Lipid Science and Technology, 106, 35
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74. Sharma, S., Pathak, S. C., & Kumar, B. (2020b). Phytochemical profile of seeds of Guizotia abyssinica (L.f.) cass (niger or Ramtil). IOSR Journal of Biotechnology and Biochemistry, 15(5), 14
22. Shashikala, B., Suma, M., & Suchitra, P. (2018). Quality control constraint of Guizotia abyssinica Cass, source of medicinally useful edible oil seeds. The Journal of Phytopharmacology, 7(5), 431
436. Swamy, M. K., Akhtar, M. S., & Sinniah, U. R. (2016). Antimicrobial properties of plant essential oils against human pathogens and their mode of action: An updated review, s.l Evidence-Based Complementary and Alternative Medicine. Thatte, P., & Lakshmi, J. (2012). Nutritional potential, bioaccessibility of minerals and antioxidant properties of niger (Guizotia abyssinicacass.) seed protein. International Journal of Food Science and Technology, 47, 656
663. Tirzitis, G., & Bartosz, G. (2010). Determination of antiradical and antioxidant activity: Basic principles and new insights. Acta Biochemica Polonica, 57, 139
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78.

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C H A P T E R

7 Antimicrobial activity of Roselle (Hibiscus sabdariffa L.) seed oil Abdel Moneim Elhadi Sulieman1,2 1

2

Department of Food Engineering and Technology, University of Gezira, Wad Medani, Sudan Department of Biology, College of Science, University of Hail, Hali, Kingdom of Saudi Arabia

7.1 Introduction Hibiscus sabdariffa L. is a shrub belong to the Malvaceae family that develops and grows in the tropic and subtropical regions. The harvest was perhaps local to Asia and might have been dissipated to Africa and afterward to America in the pioneer time frame. These days, hibiscus is generally developed all through the world, where the vital makers are China, Sudan, India, Malaysia, and Mexico (Shruthi et al., 2016). Hibiscus is an annual herbaceous plant with vertical growth, reaching a height of about two meters. The branches of the plant are reddish-green. The leaves are simple, with long petioles and serrated edges palm-shaped leaves are reddish-green. The plant bears fleshy-shaped, beautiful flowers. It is purple in color, emerging from the axillary leaves, and has a very short neck, and the flower parts are thick and lubricated with color dark red, the fruits are in the form of capsules with a number of brown seeds, spherical and wrinkled inside surface. The used part is the flower and leaf hibiscus plant is known by several names such as hibiscus Jokers, gypsies, clams, stirrups, red acidosis, hibiscus is known scientifically as Hibiscus sabdariffa (Alkahtani, 2020). The Hibiscus sabdariffa is one of the most important economic plants in food and pharmaceutical industries, its used as a refreshing drink, especially after it has been sweetened with sugar, and this extract after its concentration is considered as a colored and enriched material for the distinctive (Cid-Ortega & Guuerrero-Beltran, 2015; Da-Costa-Rocha et al., 2014; Shruthi et al., 2016). Research conducted on Hibiscus calyx showed that the extract of this part has effects in exterminating the tuberculosis microbe, and has the ability to kill microbes, particularly many bacterial strains, especially Bacillus, Escherichia coli, and others, in addition to some parasites. From researches conducted on Hibiscus calyx and leaves, they calm the contractions of the uterus, stomach, and intestines, remove its pain, and are also useful against diets. The boiled sirup of hibiscus flowers is one of the best drinks (Alkahtani, 2020) (Figs. 7.1
7.5).

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FIGURE 7.1 Roselle plant and cylyces.

FIGURE 7.2

(A) Hibiscus sabdariffa seed capsule; (B) Hibiscus sabdariffa seeds. Source: From https://commons.wiki-

media.org.

FIGURE 7.3 Fatty acid composition of the crude Roselle seed oil (percentage of total fatty acids content).

Roselle has been recognized for its numerous antibacterial and antioxidants. It can be utilized for many ailments, it is moisturizing, tonic, digestive, cleanser, laxative, and useful for chest pain, asthma, stomach weakness, arthritis, rheumatism, gout, renal scissors, and against alkaline drinks. Hibiscus is usually used in several forms, and it is eaten raw and it can be added to the soup and can be cooked along with butter or oil or with eggs (Da-Costa-Rocha et al., 2014; Fu et al., 2016; Herald & Davidson, 1983; Taylor et al., 2005).

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FIGURE 7.4 Important phytochemicals in Roselle calyces and seeds.

FIGURE 7.5 Antibacterial activity of Roselle against clinical isolates and standard bacteria.

7.2 Roselle distribution, ecology, and cultivation The genus Hibiscus (Malvaceae) incorporates in excess of 300 types of bushes or trees (Ali et al., 2005: The Plant list, 2010; Wang et al., 2012). These days, it is generally developed in tropical and subtropical districts (Sudan, Egypt, Nigeria, and Me´xico and many Asiatic countries) (Chewonarin et al., 1999; Dung et al., 1999; Eslaminejad & Maziah Zakaria, 2011; Morton, 1987; USDA, 2007). Hibiscus cultivation does well in hard climates in America and can withstand winter temperatures below 230 F. But it may grow in other areas where temperatures drop below 27 F in the winter.

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7. Antimicrobial activity of Roselle (Hibiscus sabdariffa L.) seed oil

Hibiscus can be grown in containers in cold regions; however, it can be simply introduced indoors, when temperatures start to drop to 10 C. Cultivation of hibiscus has some fairly specific requirements for the plant to bloom; But its wonderful flowering and useful yield deserve these requirements, to suit the growth.When hibiscus cultivation, the tree reaches its mature height, within 2
3 years, with an abundance of healthy, lush leaves and abundant flowering (https://faharas.net/grow-hibiscus/).

7.3 Nutritional and phytochemical composition of Roselle The chemical composition of Roselle varies, this might be due to variation of cultivars and collecting conditions (Salami & Afolayan 2020; Ismail et al., 2008). Roselle fresh calyces contained: 2.61, 12.0, 6.9, and 1.145 of fat, fiber, ash, and protein, respectively. They contained also the minerals: calcium 12.63 mg, phosphorus 2732 mg, and iron 8.98 mg. As for vitamins, Roselle contained: 0.029, 3.765, 0.117, 1.7, and 0.277 mg of carotene, niacin, thiamine, ascorbic acid, and riboflavin, respectively (Wong et al., 2002), and (Amin et al., 2008; Babalola et al., 2001) antioxidants (Hertog et al., 1993). Table 7.1 shows the average of proximate chemical composition of Roselle seeds from the various sites as determined by many investigators (Sulieman, 2014; Mahadevan et al., 2009; Elneairy, 2014; Mariod et al., 2013; Nzikou et al., 2011). The moisture, ash, protein, crude fat, crude fiber, and cabohydrates ranged between 9.76% 6 0.25% and 12.5% 6 0.1%, 7.7% 6 0.2% and 8.4% 6 0.1%, 0.18% 6 0.05% and 0.31% 6 0.1%, 13.1% 6 0.4% and 13.4% 6 0.2%, and 55.26% and 58.02%, respectively. The phytochemical constituents of alcohol extract of Roselle seeds is used for evaluation qualitatively, for alkaloids (Mayer’s test) (Stahl, 1973), saponins (Foam test), tannins (Ferric chloride test), anthraquinones (Borntra¨ger test) (Solihah et al., 2012), phenolic compounds, and flavonoids. The phytochemicals in Roselle calyces as per Okereke et al. (2015) contained flavonoids 20.08%, tannins 17.00%, saponins 0.96%, phenols 1.10%, alkaloids 2.14%, TABLE 7.1 Proximate chemical composition of Roselle seeds. Parameter (%)

Content (%)

References

Moisture

9.76 6 0.25
12.5 6 0.1

Sulieman (2014), Mahadevan et al. (2009), Nzikou et al. (2011), Mariod et al. (2013), Elneairy (2014)

Ash

5.66 6 0.01
11.5 6 0.2

Sulieman (2014), Mabrouk et al. (2016), Nzikou et al. (2011), Mariod et al. (2013), Elneairy (2014)

Protein

7.7 6 0.2
25.87 6 0.36

Sulieman (2014), Mabrouk et al. (2016), Nzikou et al. (2011), Elneairy (2014).

Fat

9.8 6 0.2
21.05 6 0.13

Sulieman (2014), Mabrouk et al. (2016), Nzikou et al. (2011), Mariod et al. (2013), Elneairy (2014)

Crude fiber

13.4 6 0.2
18.95 6 0.5

Sulieman (2014), Mabrouk et al. (2016), Nzikou et al. (2011), Mariod et al. (2013), Elneairy (2014).

Carbohydrates

55.26
58.02

Sulieman (2014)

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95

and glycosides 0.132%, which probably given it its pharmacological properties. Concentrate of calyces has been accounted for to decrease the consistency of the blood; likewise it has antimicrobial, diuretic, febrifugal, antihypertensive, and antihelminthic properties (Delgado-Vargas & Paredes-Lopez, 2002; Desrosier, 1970).

7.4 Uses of Roselle Practically all parts of the plants are utilized for food. The calyces are, nonetheless, the most useful part (Yadong et al., 2005). The plant has been utilized in people medications, as a coloring agent, and for drink or tea preparation. The calyces have been utilized to create "Cranberry" in America, for mixers preparation in Europe for soda creation in West Africa. In the United States, guidelines permit the utilization of calyces concentrates to fabricate alcoholic beverages (International Organization for Standardization, ISO 3103, 2019). The expanded rate of consuming Roselle beverage is a direct result of its supplement and therapeutic qualities, as it is savvy (Shruthi & Ramachandra, 2019), promptly accessible, and simple to get ready, and furthermore due to its great taste, fragrance, and color. These are inherent highlights of the plant. As of now, many great individuals from various social and monetary levels in West Africa devour the beverage (Ogiehor & Nwafor, 2004) and the beverage has become a mainstream worldwide reviving beverage. Because of the intense usage of the beverage, its deal has become a method for vocation by numerous ladies in West Africa. It has been reported that zobo (Roselle product) contains flavoring, antimicrobial, antiinflammatory, antihyperglycaemic, hypolipidemic, antioxidant, and anticancer properties. These properties support recorded wellbeing, and therapeutic activities of H. sabdariffa calyxes, and refreshment. A few distinguished constituents share comparative activities. The synergism of these mixtures approves the restorative impacts of “zobo” (Kolawole & Maduenyi, 2004). Hibiscus seeds and their extracts have been reported to offer numerous benefits to the human body as follows: • A rich source of protein: Roselle seeds are one of the sources rich in proteins, and some amino acids such as lysine, arginine, leucine, phenylalanine and Glutamic acid. • Antioxidant impact: The extracts of the seeds of the hibiscus plant have an antioxidant impact, and this impact increases when the antioxidants in the extracts are bound to other antioxidants (Ismail et al., 2008). • Rich source of fiber: The Roselle seed husk contains a high percentage of insoluble dietary fiber, in addition to the inner part of the seeds containing high levels of soluble dietary fiber. It is known that consuming fiber supplies the body with numerous health and physiological benefits (Ismail et al., 2008) • A source of other elements: Roselle seeds contain oils, in addition to several nutrients that contribute to promoting health, such as vitamins, minerals, and fatty acids. Saturated and unsaturated foods (Ghazala, 2019). A study conducted on mice indicated that adding fat-free and dried hibiscus seed powder to the diet may contribute to lowering levels of Cholesterol in the blood (Emmy et al., 2008).

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7. Antimicrobial activity of Roselle (Hibiscus sabdariffa L.) seed oil

7.5 Roselle seed oil The seeds of Roselle, which right now don’t have any economic application, are a source of a vegetable oil that is low-cholesterol and rich in other phytosterols and tocopherols, especially β-sistosterol and γ-tocopherol. The worldwide qualities of Roselle seed oil permit significant modern applications for this oil. These attributes address an additional incentive for the way of life of this plant (Mohamed et al., 2007). The percentage of oil that can be extracted from hibiscus seeds is 17% and the seeds. It is considered a by-product because the main crop is the sepals and the petals that are collected for the manufacture of drinks and carbonated water, as well as fiber. Oil is extracted from the ground seeds using petroleum ether. It was found that the oil obtained from ripe seeds is better than the immature seeds in terms of general qualities. The ground seeds are not affected much by the enzymatic degradation, the obtained oil is stable and characterized by fairly high resistance to oxidation and spoilage. The color of the crude oil is affected if exposed to a temperature of 170 C, so care must be taken not to raise the temperature to 150 C during the manufacturing steps. So, it can suffice with a washing oil with water in the purification process, then follow the rest of the normal vegetable oil purification steps, which include the neutralization of the free acids, the shortening of the color and the removal of the odor by passing a stream of steam. Moreover, the hibiscus seed oil is used after being purified as edible oil, and it was used in frying foods and no unusual phenomena were observed on it, and it is an oil with a normal taste, free of odor, and it has a desirable color is and similar to refined cottonseed oil (Ali, 1996).

7.5.1 Physicochemical characteristics of Roselle seed oil The physicochemical characteristics of Roselle seed oil ensure its use as an edible oil (Isaac Bamgboye & Adejumo, 2010). The saponification value, iodine value, viscosity, refractive index and specific gravity of the Roselle seed oil are: 126.2, 111.2, 22.5 cp, 1.4472 and 0.9558, respectively. The peroxide value of Roselle seeds varied between 6.0
9.3 and 5.9
9.0; and free fatty acid, 0.435
2.300 and 0.510
3.311 for fine and coarse samples, respectively. Mohamed et al. (2007) found that, the extracted Roselle seed oil in a Soxhelt extractor using n-hexane at 65 C
70 C during the time important to quantitatively extract all the oil from the seeds had refractive index, 1.477; peroxide value, 8.63 and acidity, 2.24%. These distinctions might be credited to the distinctions in the technique for oil extraction

7.6 Microbiology of Roselle Omemu et al. (2006) analyzed dried calyx and isolated some microorganisms from the dried calyx and the juice made from it included the fungi, Aspergillus niger, Aspergillus flavus, Rhizopusoligosporus, Penicilliumcitrinum, Mucor spp., Saccharomyces cerevisiae, and Candida krusei, While the bacterial species included: Bacillus subtilis, Pseudomonas spp., Staphylococcus aureus,

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97

Streptococcus faecalis, Escherichia coli, Proteus mirabilis, Serratia spp., Lactobacillus brevis and ´ ngel et al., 2015). They Lactobacillus fermentum. Roselle is attacked by several fungi (Santo A include: Aecidium garckeanum, A. hibiscisurattense, Alternariamacrospora, Cercosporaabelmoschi, C. malaysensis, Corynesporacassiicola, Cylindrocladiumscoparium, Diplodiahibiscina, Fusariumdecemcellulare, F. sarcochroum, F. solani, F. vasinfectum, Guignardiahibisci-sabdariffae. Roselle plants are also attacked by several viruses: Leaf curl, Cotton leaf curl and Yellow vein mosaic. The bacterium, Bacillus solanacearum, has been isolated from Roselle (Patricia et al., 2016). They are very seriously attacked by root-knot nematodes such as Meloidogynearenaria, M. incognita acritaand M. javanica. Among the insect pests which attack Roselle are Anomiserosa, Chaetocnema spp., Cosmophilaerosa, Dysdercuscingulatus, D. poecilus, Drosichatownsendi, Nistoragemella, Phenacoccushirsutus, Pseudococcusfilamentosus, and Tectocorisdiophthalmus (Ogunsola et al., 2018).

7.7 Antimicrobial activity of Roselle Phytochemical screening test is of foremost significance in recognizing new wellspring of restoratively and modernly important compound having therapeutic importance, to make the best and reasonable utilization of accessible common abundance (Garbi et al., 2016). Regular antimicrobials have gigantic helpful potential, since they can likely lead the necessary capacities without any posing wellbeing risks frequently connected with manufactured specialists. The in vitro antimicrobial activity of Roselle was attributed to its flavonoids, which can set up complexes with the bacterial cell walls, upgrading their pervasion to the extract. The mechanism of action may incorporate a few metabolic steps, such as hindrance of electron transport protein movement, phosphorylation steps, and some other enzyme subordinate responses finishing with raised film permeability combined with the spillage of the bacterial cell constituents (Fullerton et al., 2011). The antimicrobial activity of Hibiscus sabdariffa Crude, phenolic-rich extract (HCPRE, 2000 μg/mL) was tested by Abdel-Shafi et al. (2019) against Pathogenic including S. aureus, Streptococcus pyogenes, Listeria monocytogenes, E. coli, K. pneumonia, and Pseudomonas aeruginosa. The CPRE exhibited the highest inhibition zones against the all bacteria (Table 7.2). The antibacterial impacts of Roselle calyx watery and ethanol extracts against food spoilage bacteria Salmonella typhimurium DT104, E. coli O157:H7, L. monocytogenes, S. aureus, and B. cereus were inspected by Wang and Stoner (2008). The inhibitory activities in a dose-dependent, and it was suggested that they might be powerful agents as food additives toprevent contamination from these microbes. Garbi et al. (2016) found that the consequences of methanol extract of Roselle displayed inhibitory impacts against the greater part of the tested organisms, with the zone of inhibition ranging from 14 to 36 mm in length. The biggest inhibition zone was gotten for the Gram-positive against bacterial species including: L. monocytogenes (36 mm), E. faecalis (33 mm), B. cereus (28 mm), C. diphtheriae (26 mm), and S. aureus (24 mm). The most inhibited Gram-negative bacteria included P. aeruginosa (ATCC 27853) (28 mm), K. pneumoniae (ATCC 70063) (25 mm), P. aeruginosa (23 mm), E. coli (20 mm), E. coli (ATCC 25922), P. vulgaris (19 mm), K. pneumonia (18 mm), S. marcescens

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7. Antimicrobial activity of Roselle (Hibiscus sabdariffa L.) seed oil

TABLE 7.2 Antibacterial activity of crude phenolic rich extracts (CPREs) (2000μg/mL) from Roselle plants against pathogenic bacteria using agar well diffusion assay. Microorgansim

Inhibition zone (mm)

Gram-positive bacteria Staphylococcus aureus

48 6 8.0

Streptococcus pyogenes

40 6 5.0

Listeria monocytogenes

32 6 4.0

Gram-negative bacteria Escherichia coli

46 6 6.0

Klebsiella pneumonia

48 6 6.5

Pseudomonas aeruginosa

32 6 3.0

(17 mm), and P. mirabilis (14 mm). Hence, these outcomes showed that the concentrates tried hindered the development of all bacteria though the sensitivities of bacteria differed. Abd-Ulgadir et al. (2015) determined comparative outcomes.

7.8 Conclusion In conclusion, Hibiscus sabdariffa seed oil is one of the most promising sources for new natural and effective antibacterial drugs competitor to antibiotics. It can be effectively utilized as safe, natural products.

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C H A P T E R

8 Antioxidant and antimicrobial activities of Monechma ciliatum seed oil Abdalbasit Adam Mariod1,2 and Haroon Elrasheid Tahir3 1

Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 2College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia 3School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China

8.1 Introduction Generally, herbs are considered as good sources of nutrients and supplements for food, as they are important sources of many nutritive components essential for humans also they are essential for animals feed (Rathod & Valvi, 2011). Acanthaceae family is a tropical and subtropical native dicotyledonous flowering plant. It is one of the richest families with nutritional and medicinal components (Awan et al., 2014). This family includes about 346 genera and around 4300 species some of these species have colorful flowers petals, so they are used as a source of natural dyes (Fayed, 2013). Most species have high therapeutic applications due to their alkaloids contents (Sharma & Kumar, 2016). Studies on many species showed they are used in the treatment of bronchial diseases, relieve bites of poisonous insects, treating reptiles snake bites with and relieve dry cough, diarrhea, flu, and ulcers (Hossain & Hoq, 2016). The genus Monechma Hochst., is an African genus contains about 60 species most of them are found in tropical and subtropical regions, generally, Monechma described as well-adapted plants to survive in a hard environment. M. ciliatum is a species of Monchema genus plant contains unique biochemicals and phytochemicals prosperities that made it traditionally useful for many African populations specially in rural areas. This chapter is exploring the traditional uses, antioxidant, antimicrobial, and medicinal properties.

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8. Antioxidant and antimicrobial activities of Monechma ciliatum seed oil

FIGURE 8.1 Monechma ciliatum plants grown in rows.

8.2 Monchema ciliatum (black mahlab) M. ciliatum belongs to the Acanthaceae family. It is a herbaceous plant 30
65 cm tall. Linear sheets of thin shape 10 cm wide and 1.25 cm wide. The plant has a white flower and bushy seed, and a similar tuft at the other end. The plant can grow up to about one meter in height making it possible to be grazed by domestic animals. The plant is found widely in Senegal, Cameroon, Sudan, and Zambia, and this plant needs an appropriate climate to reach the best vegetative growth. The plant is found to grow in the cold season as well (Uguru, et al., 1998). M. ciliatum is a small herbaceous plant that grows a few inches above the ground, the leaves are simple. In Sudan, this plant is known locally as black mahlab and is found in its wild form in many states of Sudan, especially in the Nuba Mountains and the Jebel Marra region. In Sudan, the plant grows and thrives in the fall season is the best time to plant it. The distances between plants have a great influence on vegetative growth and crop yield. As it turned out that the more distant the plants were, the higher the vegetative growth and the successful reproduction. Successive harvesting is required before the fruits reach the dispersal stage. It was found that the seeds of the fixed oil were higher in the plants grown in the fall than the plants grown in the winter and summer (Mohammed & Elballa, 2015). In Sudan where it is well known and traditionally used in the treatment and cosmetics, it has a small brownish-black seeds, this why the Sudanese people call it the black mahlab (Mariod et al., 2009). In Northern Nigeria, it is locally known as Damfarkami in Hausa language, it is characterized by long tap root and lanceolate (Ogunsan et al., 2010). The species is well known and traditionally used in Kenya, leaves were grazed by sheep and goats and also harvest at the end of rainy season and store it as hay to be used during the dry season (Ogunsan, et al., 2011) (Fig. 8.1).

8.3 Nutritional value and chemical composition of Monchema ciliatum Plants are cheaper sources of proteins when compared to animal proteins in developing countries. The protein content of the M. ciliatum seed as reported by Mariod et al. (2009) is 21% with 783.3 mg/g N, as an essential amino acid. The M. ciliatum seeds content of fat is 13.15%, with palmitic 4.5%, stearic 16.0%, oleic 47.3%, and linoleic 31.4%, and has a good amount of tocopherols as 45.2 mg/100 g, It contains minerals and the total phenolic

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FIGURE 8.2 Monechma ciliatum seeds.

compounds of M. ciliatumm seeds was found to be 17.1 mg GAE/g (Mariod et al., 2009). Hassan et al. (2018) examined M. ciliatum leaves and concluded they contain 14% ash, 5.34% crude protein, 4.14% crude lipid, 3% crude fiber, available carbohydrate 73.50%, energy value 352.63 (kJ/100 g DW) and a considerable amount of K, Na, Ca, Mg, Cu, Fe, Mn, and Cr as essential minerals. Leaves also contain low levels of antinutritional content such as oxalate, phytate, nitrite, cyanide, and tannins which were below established toxic levels. M. ciliatum seeds are rich in protein, fat minerals, and other essential nutrients, also it has many benefits in traditional treatments (Mariod et al., 2009). Leaves are also found to be a good source of nutritive compounds and minerals (Hassan, et al., 2018). Oshi and Abdelkareem (2013a) reported they have unique cosmetical components. Many studies were conducted to validate the traditional uses of the different parts of the plants. As M. ciliatum seeds (Fig. 8.2) are previously known as a rich source of protein, fat, minerals and other essential nutrients Abdelrahman (2021) conducted a study to evaluate the impact of M. ciliatum as a plant-based supplement on sorghum kisra (Sudanese bread made of sorghum flour as stable diet for most of Sudanese population) and the improvement on its nutritional value. and investigated the effect of composite sorghum flour with untreated, boiled, roasted, and germinated M. ciliatum Results showed that the supplementation of sorghum kisra with untreated and treated M. ciliatum significantly and generally improved its nutritional value, Specifically increased fat, fiber, mineral, unsaturated fatty acids, protein and amino acids content and sorghum kisra, supplemented with 10% M. ciliatum seed flour, was found to be acceptable with respect to all sensory attributes. it’s clear that M. ciliatum seed flour could be effective in food fortification.

8.4 Antioxidant activity of Monechma ciliatum The practice of using herbal as food supplement and medicine has been accepted throughout the world. Studies concluded that consuming variety antioxidant compounds from natural source foods can help in treating serious health disorders (Mariod et al., 2009). Antioxidants are chemical compounds of great benefit to humans. Reducing free

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radicals and/or reducing their rate of production also inhibits the production of lipid peroxides in the human body that cause many human diseases and aging (Galati & Brien, 2004). Research has shown that consuming a variety of phenolic compounds found in natural foods may reduce the incidence of some diseases due to the antioxidant activity of these phenols. When adding phenolic compounds to foods, they undoubtedly reduce rancidity, delay the formation and harmful oxidative products, maintain food quality, and increase shelf life (Jadhav, et al., 1996). M. ciliatum has been used traditionally for treating many kinds of diseases. Studies conducted to support and prove this traditional usage reported that M. ciliatum leaves extract has powerful antioxidant effect due to the high content of total phenolic (Mariod et al., 2010b). Mariod et al. (2010a) investigated the antioxidant activity of black mahlab seed extract and they revealed that phenolic rich fractions (PRFs) had the highest antioxidant activity, thus it reduced the oxidation of β-carotene by hydro-peroxides from the extracts. Hassan et al. (2018) conducted a study of phytochemical analysis and in vitro antioxidant activity of different leaves extract of M. ciliatum leaves and stated that M. ciliatum is a good source of various metabolites like steroids, flavonoids, phenolics, alkaloids theses antioxidants have promising radical scavenging activity comparable to standard ascorbic acid and concluded that the leaves of the plant could be a potential source of natural antioxidant.

8.5 Antimicrobial activity of Monechma ciliatum A large number of medicinal plants are used in many countries around the world in traditional medicine as a treatment for skin diseases caused by bacteria and fungi. In Sudan, seed powder and aqueous paste from black mahlab are used in the treatment of skin, and mucous membrane problems, such as rashes, oral thrush and gingivitis (Mariod et al., 2009). Traditional uses of M. ciliatum against microbial diseases encourage researchers to conduct experiments to prove and support these traditional beliefs by identifying the effective components and the suitable amounts and methods that should be used to obtain the benefits. Microbial activities of M. ciliatum showed significant antibacterial activity against Bacillus subtilis, Staphylococcus aereus, Escherichia coli, and Pseudomonas aeraginosa compared with well-known antibiotics and antifungal activity against Cladosporium cucumerinum and Candida albicans. Studies on the seeds extracts and seedcakes and leaves showed they have great contents of nutrients as antioxidant, antimicrobial, and medicinal components. In phytochemical screening conducted by Oshi and Abdelkarim (2013b), their result supported these traditional uses in the therapy of respiratory tract infections caused by a wide range of microbes and fungi. They found that this is due to seeds content of flavonoids, tannins, tritepens, and Quinones. These antimicrobes affected Staphylococcus aurous which was sensitive to both water and ethanol extracts. Klebsiella pneumonia and Pseudomonas aeruginosa were found to be insensitive to ethanol extract while fungi were found to be insensitive to all extracts used. The minimum inhibitory concentrations of the extracts against microorganisms were ranged from 12.5 to 25 mg/mL. Osman (2007) studied the antimicrobial activity M. ciliatum stem using three extracts and reported that it is

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due to its content of many active components (fatty acids, alkaloids, volatile oils, triterpenes, sterols and carotenoids, coumarins, flavone aglycone, emodols, tannins, polyuronides, alkaloid salts, reducing compounds and saponins) and suggested that the most active components were found in methanolic and petroleum ether extracts. Also, Abdel Karim et al. (2017) examined the antimicrobial activity of the seeds oil of M. ciliatum and reported that it has a significant effect on Aspergillus niger and Candida albicans fungi and Staphylococcus aureus bacteria. The oil was found to be active against Escherichia coli and Pseudomonas aeruginosa. However, it was not active against Bacillus subtilis. Petroleum ether extract has shown high efficacy as a broad spectrum antifungal. And attribute these effective effects to the presence of phenols and sterols, and also found in methanol extract that tannins, flavonoids, coumarins, saponins, and triterpenoids. Abulgasim et al. (2015) studied the antimicrobial activities of extracts of M. cilatum stem and leaves and reported that The concentration of the active antimicrobial constituents is different in leaves and stem of M. cilatum so leaves methanolic extract was more effective with standard bacteria, Gram-positive and Gram-negative, while fungi was less sensitive to same extracts (Manal, 2008) investigated the antimicrobial activity and pharmacological properties of M. ciliatum and testified that the chloroform fraction of leaves possess significant antimicrobial activity against S. aureus. Oshi and Abdelkareem (2013a) validated the folk’s claim of inhalation of M. ciliatum seeds powder by traditional African natives and Sudanese people in Nuba Mountains regions, they concluded that the traditional uses of M. ciliatum seeds and seed oil for cosmetics purposes referred to antioxidant activity of flavonoids, and tannins, these component consider as the effective substitutes in limiting the damage caused by free radicals of skin. The triterpenses and sterols are aromatic constitutes of medicinal plants. The high antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Klebsiella pncumoniae, Escherichia coli, Candida albicans and Aspergillus niger of black mahlab seeds provides a scientific evidence for the traditional uses of black mahlab seeds as cosmetical for skin and mucous membrane disorders.

8.6 Uterotonic property of Monechma ciliatum Uguru, et al. (1995), tested different solvent extracts of the leaves of M. ciliatum for oxytocic properties on uterine preparations, he found that methanol extract affected the uterus of rats, guinea pigs, and pregnant mice as well as the preparations obtained from guinea pigs on days 6
7 and 11
12 of pregnancy, while the uterus of pregnant rats was not affected by the extract. There was no abortive effect in rats when given orally administered methanolic extract on days 15, 16, and 17 of pregnancy when compared with oxytocin. But on day 23, upon opening the abdomen, the fetus was found dead in the uterus. The study also showed that the extract has estrogenic activity based on different conditions. In 1998 the same researcher compared the oxytocytic activity of the hot methanol extract (HME) of M. ciliatum leaves with ergometrine, oxytocin, 5-hydroxytryptamine (5-HT), acetylcholine (ACh), prostaglandins (PGs) E2, F2alpha (PGE2), and PGF2. Which act as uterine stimulants with the presence of some antagonists in an attempt intended to explain the mechanism by which the extract works. It has been shown that this extract works by more

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than one mechanism for contracting the uterus and explains the mechanism of antiimplantation activity of M. ciliatum extract. Uguru, et al. (1999) purified the hot methanol extract (HME) of M. ciliatum to isolate the oxytocic principle, the polarity of the oxytocic is significant and by the positive reaction with ninhydrin-spray suggested that it is an amino acid by a combination of bioassay and repeated column chromatography on silica gel followed by sephadex LH-20 on the rat uterus partially identify the oxytocic principle (P3) which was suggested by previous studies as small peptide constructed of tyrosine, leucine and a third constituent that is probably serine. To validate the traditional believes and uses of M. ciliatum to reduce pain and ease parturition and according to the previous studies, antinociceptive effect of M. ciliatrum was studied by Meraiyebu, et al. (2010). Using a Von Frey anesthesia scale. The results obtained confirmed the antipain effect significantly in the case of oral or intrathecal administration, but the effect was greater when administered orally and during the first 15 minutes of intrathecal administration. EEG readings for all groups indicated a decrease in amplitude and an increase in frequency at high doses (1000 mg/mL), as the mid-brain electrodes showed a change from theta (3.5
7 waves per second) to alpha waves (7.5
13 waves per second) similar to that found in relaxed persons while amplitudes beta waves distribution was changed and reduced, these effects revealed similar properties for sedative-hypnotic drugs.

8.7 Antimalarial activity of Monechma ciliatum Shayoub, et al. (2016) evaluated antimalarial activity of M. ciliatum extract of different solvent against Plasmodium falciparum (Malaria) which known as one of the most common major health problems all over the world. The extracts of M. ciliatum were screened for their antimalarial activities against Plasmodium falciparum with different concentrations of 500, 250, and 125 μg/mL they resulted to have powerful antimalarial activities. Another study carried out by Mariod, Ghanya, et al. (2010) on the effects of M. ciliattm methanolic extrat MCME at 10, 20 and 50 μg/mL on low density lipoprotein receptor (LDLR). They concluded that MCME concentration played major role on its effect, and different doses revealed clear impact in normalization of LDLR and HMGCR genes, impacts revealed that MCME successfully organized the expression of LDLR and HMGCR genes affecting the cholesterol metabolism in HepG2 cells. According to the African traditional medicinal uses, M. ciliatum seed’s powder soaked in water and drunk or inhaled for cold treatment, to proof these important medical uses Oshi and Abdelkareem (2013a) formulated and studied a conventional dosage form (tablets) from M. ciliatum seed’s ethanolic extract, using the wet granulation method. They prepared two formulae: formula-1 by using starch as a binder and disintegrant and formula-2 by using polyvinyl pyrrolidine (PVP) and cross carmellose cellulose (CCS) as a binder and disintegrate the study concluded that Formula-1 was quite effective as super disintegrant and it was more acceptable. Using oleic acid, coumarin, 1,2-dioleoylglycerol, and 1,3-dioleoylglycerol isolated from water extract of M. ciliatum seeds and conducted a study of these components activity, results validated the application of using M. ciliatum as an effective therapeutic agent to prevent periodontal diseases (Eltigani et al., 2019).

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8.8 Anticancer activity Some recent studies have shown that essential oils have a wide activity, which is attributed to the fact that they contain a variety of effective compounds. These studies have shown that most of these compounds have been shown to reduce and may be beneficial in treating cancer (Oliveira, 2015). Phenolic compounds and flavonoids are chemicals that are extracted from plants such as vegetables, fruits, and grains. They are always in the form of secondary metabolites that act as natural antioxidants that have multiple biological effects and play an important role in defense against cardiovascular disease, aging and cancer (Tungmunnithum, et al., 2018).

8.9 Cosmetical uses of Monechma ciliatum seeds and oil Herbs are traditionally used for beauty relaying on traditional medicine literature over years, the herbal extracts have been utilized for different diseases of the whole body, and hair. The consumer reports an increasing demand for the herbal manufacturing to fill the gap worldwide. The consumers demand for herbal beauty products has been attributes to declining of faith in modern chemical cosmetics. The M. ciliatum seeds are used in traditional Sudanese beauty and healthcare products such as “Dilka” and “Khumrra” (Mariod et al., 2009). M. ciliatum is used as odor and fragrance source in Western Sudan. It has a pleasant aromatic odor which is very important component of heavy Sudanese traditional fragrance like “Karkar oil”.

8.10 Conclusion Its clear that seeds of M. ciliatum contain valuable source of human nutrients, leaves are good for animal feed and most parts of the plant have great antioxidant, antimicrobial, and cosmedical properties, further work on these properties are needed to corroborate the primary mechanisms as antioxidant antimicrobial agents. The plant could become a valuable source of income if commercially exploited by the food and medical industries and researchers.

References Abdel Karim, M., Faiza, I., & Inas, O. (2017). Monechma ciliatum Oil: GC-MS analysis and antimicrobial activity. International Journal of Scientific Engineering and Applied Science (IJSEAS), 3, 2395
3470. Abdelrahman, E. M. (2021). Effect of boiling, roasting and germination processing methods on black malab seeds (Monechma ciliatum) nutritional value and its effect as food supplement on sorghum kisra quality (MSc. Thesis). Khartoum, Sudan: Sudan University Science and Technology, Department of Food Science and Technology. Abulgasim, A. I., Ali, M. I., & Hassan, A. (2015). Antimicrobial activities of extracts for some of medicinal plants. International Journal of Advanced and Applied Sciences, 2(2), 1
5.

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Awan, A. J., Ahmed, C. B., Uzair, M., Aslam, M. S., Faroog, U., & Ishfaq, K. (2014). Family Acanthaceae and genus Aphelandra: Ethnopharmacological and phytochemical: Review. International Journal of Pharmaceutical Science, 6(10), 44
55. Eltigani, S. A., Eltayeb, M. M., Ishihara, A., & Arima, J. (2019). Isolates from Monechma ciliatum seeds’ extract hampered Porphyromonas gingivalis Hemagglutinins. Journal of Food Biochemistry, 43(11), e13029. Available from https://doi.org/10.1111/jfbc.13029. Fayed, M. A. (2013). Phytochemical and biological studies of certain plants belonging to family Acanthaceae (a thesis for the Degree of Doctor of Philosophy in Pharmaceutical Sciences). Assiut, Egypt: Assiut University, Pharmacognosy Department, Faculty of Pharmacy. Galati, G., & Brien, P. J. (2004). Potential toxicity of flavonoids and other dietary phenolics: Significance for their chemopreventive and anti-cancer properties. Free Radical Biology & Medicine, 37, 287
303. Hassan, L. G., Msheila, H. E., Umar, K. J., Umar, A., & Onu, A. (2018). Nutritional and anti-nutritional analysis of Monechma ciliatum leaves. Research Journal of Food Science and Nutrition, 3(3), 23
30. Hossain, T., & Hoq, O. (2016). Therapeutic use of Adhatoda vasica. Asian Journal of Medical Biology Research, 2(2), 156
163. Jadhav, S. J., Nimbalkar, S. S., Kulkarni, A. D., & Madhavi, D. L. (1996). Lipid oxidation in biological and food systems. In D. L. Madhavi, S. S. Deshpande, & D. K. Salunkhe (Eds.), Food antioxidants (pp. 5
63). New York: Dekker Press. Manal, I. A. (2008). Antimicrobial and pharmacological properties of some medicinal plants (M.V.Sc. Thesis). Khartoum, Sudan: University of Khartoum. Mariod, A., Ghanya, A., & Maznah, I. (2010). Monechma ciliatum methanolic extract regulates low density lipoprotein receptor and 3-hydroxy-3-methylglutaryl coenzyme A reductase genesexpression in HepG2 cells. African Journal of Biotechnology, 9(36), 5813
5819. Mariod, A., Ibrahim, R. M., Ismail, M., & Ismail, N. (2010a). Antioxidant activities of phenolic rich fractions (PRFs) obtained from black mahlab (Monechma ciliatum) and white mahlab (Prunus mahaleb) seed cakes. Food Chemistry, 118, 120
127. Mariod, A. A., Ibrahim, R. I., Ismail, M., & Ismail, N. (2010b). Antioxidant Activity of the Phenolic Leaf Extracts from Monechma ciliatum in stabilization of corn oil. Journal of the American Oil Chemists’ Society, 87, 35
43. Mariod, A. A., Aseel, K. M., Mustafa, A. A., & Abdel-Wahab, S. I. (2009). Characterization of the seed oil and meal from Monechma ciliatum and Prunus mahaleb seeds. Journal the American of Oil Chemist Society, 86, 749
755. Meraiyebu, A. B., Adelaiye, A. B., Odeh, S. O. (2010). The antinociceptive effects of Monechma ciliatum and changes in EEG waves following oral and intrathecal administration in rats. In: Proceedings of the. SPIE 7552, mechanisms for low-light therapy V, 75520Q. 4 March. https://doi.org/10.1117/12.846101. Mohammed, T. M. S., & Elballa, M. M. A. (2015). The effect of agricultural practices on growth and yield of black mahlab (Monechma ciliatum). Agricultural and Biological Sciences Journal, 1(2), 31
36. Ogunsan, E. A., Ipinjolu, J. K., & Daneji, A. I. (2010). Effects of feeding different levels of monechma ciliatum on the performance of rabbits in sokoto. Nigeria Journal of Animal Science, 4(5), 121
124. Ogunsan, E. A., Ehizibolo, D. O., Dashe, Y. G., & Jatau, J. D. (2011). Potentials of Monechma ciliatum as a nonconventional feedstuff in sheep diet in Sokoto, Nigeria. Pakistan Journal of Nutrition, 10(10), 987
990. Oliveira, C. M. (2015). Chemical characterization and in vitro antitumor activity of the essential oils from the leaves and flowers of Callistemon viminalis. American Journal of Plant Sciences, 6, 2664
2671. Oshi, M. A., & Abdelkareem, A. M. (2013a). Design and evaluation of cost effective conventional tablets from Monechma ciliatum seeds extract. IJPSR, 4, 2, 2013. Oshi, M. A., & Abdelkarim, M. A. (2013b). Phytochemical screening and evaluation of Monechma ciliatum (black mahlab) seed extracts as antimicrobial agents. Avicenna Journal of Phytomedicine, 3(2), 126
134. Osman, S. H. B. (2007). Chemical composition and antimicrobial activity of Monechma ciliatum (Jacq.) Milne-Redhead Stem (a thesis for the Degree of PhD in Science). Khartoum, Sudan: Al Neelain University. Rathod, V. S., & Valvi, S. G. (2011). Mineral composition of some wild edible fruits from Kolhapur district. Journal of Applied Biology and Pharmaceutical Technology, 2, 392
396. Sharma, A., & Kumar, A. (2016). Acathaceae taxonomy and uses in transitional medicinal system. World Journal of Pharmaceutical Research, 5(7), 403
412. Shayoub, S. M. E., Elhassan, A. M., Kabbashi, A. S., & Ahmed, M. E. (2016). Anti-malarial activity of Monchema ciliatum (black mahlab). World Journal of Pharmaceutical Research, 5(5), 200
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Tungmunnithum, D., Thongboonyou, A., Pholboon, A., & Yangsabai, A. (2018). Flavonoids and other phenolic compounds from medicinal plants for pharmaceutical and medical aspects: An overview. Medicines (Basel), 5 (3), 93. Available from https://doi.org/10.3390/medicines5030093. Uguru, M. O., Ekwenchi, M. M., & Evans, F. (1999). Bioassay-directed isolation of oxytocic principles from the methanol extract of Monechma ciliatum. Phytotherapy Research, 13(8), 696
699. Available from doi.org/10.1002/ (SICI)1099-1573(199912). Uguru, M. O., Okwuasaba, F. K., Ekwenchi, E. E., & Uguru, V. E. (1998). Uterotonic properties of the methanol extract of Monechma ciliatum. Journal of Ethnopharmacology, 62(3), 203
208. Uguru, M. O., Okwuasaba, F. K., Ekwenchi, M. M., & Uguru, V. E. (1995). Oxytocic and oestrogenic effects of Monechma ciliatum methanol extract in-vivo and in-vitro in rodents. Phytotherapy Research, 9(1), 26
29. Available from https://doi.org/10.1002/ptr.2650090107.

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C H A P T E R

9 Antioxidant and antimicrobial activity of fenugreek (Trigonella foenum-graecum) seed and seedoil Sara Thamer Hadi1 and Abdalbasit Adam Mariod2,3 1

Department of Food Science, College of Agriculture, University of Anbar, Ramadi, Iraq Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 3College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia 2

9.1 Introduction Herbs and spices have long been used as natural food additives. Antioxidant-active spices and herbs can be employed to keep lipid peroxidation in biological systems under control. Since then, naturally occurring antioxidants in plants have been studied as potential substitutes for synthetic antioxidants, which are used extensively in industry and scientific studies (Naidu et al., 2011). Fenugreek (Trigonella foenum-graecum) is a herbaceous plant (Fig. 9.1) used as a spice. It belongs to the legume group and is usually sold in the form of dried ripe seeds, golden to yellow in color. Its green leaves can be exploited in many traditional folk remedies, and the original home of the plant are Asia and southeastern Europe, and it is famous for its cultivation in India, North Africa, and the Eastern Mediterranean countries. Fenugreek has always been known and used to treat many medical problems, and currently there are many uses for it in the world of medicine, health and others, but so far there is not enough evidence about its effectiveness. The medicinal properties of Fenugreek will help reduce dependence on synthetic drugs that are considered serious contaminants of water resources (Acharya et al., 2006). Calcium, iron, beta-carotene, and vitamins are abundant. Lysine and L-tryptophan-rich proteins are found in fenugreek seeds, mucous fibers, as well as other uncommon chemicals ingredients saponins, for example, coumarins, phenogrequins, sapogenin, phytic acid, scopolitin, trigoniline, vegetable sterols, and lecnene, which are thought to explain many

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FIGURE 9.1 Trigonella foenum-graecum plant. Source: https://commons.wikimedia.org.

of its alleged therapeutic effects that may inhibit cholesterol absorption and help (Lust, 1986). Reduce your sugar intake Spices and herbs have been used since ancient times because of their ability to cause physiological changes, and they have revolutionized medicine. medicine, if they treat multiple cases, alter the course of history, and have economic significance in food, medicine, perfumes, and cosmetics Herbs and spices are used to enhance flavor and color in foods because they have antioxidant and microbial properties. The use of these plants can have a variety of side effects, including reducing sucrose and salt, improving texture, as well as preventing food spoilage, and the main ether when it comes to spices cooking and in sweets it is possible flavoring and deodorizing. Fenugreek Latin name is Trigonella foenum-graecum, Fabaceae family, when used as herb (leaves) and as a spice (seeds), fenugreek is grown all over the world. The seeds have many uses in folk medicine as an anticongestion and against dysentery and stomach upset. Breastfeeding mothers consume the seeds in the form of fine gruel. Fenugreek seed oil has been used in the foodservice industry to extend food shelf life, as well as in the medical and chemical industries. Fenugreek is used to treat diabetes and high blood pressure. cholesterol if it contains 5%
7% oil that contains linoleic, linolenic and oleic acids. It is anticancer, diuretic and has antibacterial and antifungal activity. The seeds are used as nutritional supplements that have a role in the digestive process and are useful for the digestive system and ulcers, they are used as a spice and are safe from a nutritional point of view and recognized by the US Food and Drug Administration (Amin et al., 2001). This herb was employed as an aphrodisiac in ancient Egypt, but today it is used to alleviate respiratory problems caused by sputum. It was used to alleviate labor discomfort and enhance milk supply, and Egyptian women still use it to relieve menstrual pain, and it is used as a drink to relieve abdominal pain, its uses vary despite people’s awareness of its nutritional value, and it is cooked in India fresh fenugreek in the form of winter vegetables, and the seeds are utilized as a varied flavoring agent throughout the year (Hadi et al., 2018).

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9.2 Botanical description Fenugreek is an annual herb, its height ranges between 20 and 60 cm. It has a hollow stem and small branches fork from it, each of which carries three long serrated leaves at the end, and from the base of the leaf stems appear small yellow flowers that turn into fruits in the form of hooked horns, the length of each horn is about 10 cm and contains seeds somewhat similar in shape to the kidney, which is greenish
yellow in color. There are two types of fenugreek, the regular municipal fenugreek, of yellowish color, and the red fenugreek, known as the horse fenugreek, and they are very different (Kumar et al., 2013).

9.3 Chemical composition Fenugreek seeds contain 25%
45% mucilage, mannogalactans, 25%
30% proteins, 6%
10% fats, in addition to steroid saponins at a rate of 1%
5.1%, the most important of which are trigofoennosides and aglycones, among which are diosgenin, yamogenin, gitogenin, smilagenin. Steroid soapy peptide ester: foenugraenin, flavonoids: vicenin, saponaretin, orientin. Alkaloids: choline by 1.3%, trigonelline by 0.4%. Fenugreek seeds contain a volatile oil, and sesquiterpene compounds and lactones, sugars, including galactose and mannose, minerals (phosphorous, iron, sulfur, calcium, magnesium), and vitamins A, C, and B1 (Naidu et al., 2011; Sulieman et al., 2008).

9.4 Different uses of fenugreek In fact, fenugreek seeds have included many healing properties, and this is evidenced by the ancient medical uses of the Arabs. The plant saliva was used to soften solid tumors, and internally they were used cooked with dates and figs to treat chest pain, coughing, asthma, shortness of breath, expelling gas and menstruation. It was also used to facilitate childbirth, purify the uterus, and treat hemorrhoids, as it was considered a fattening and tonic food for the body. It was also given to treat spleen tumors while using a mixture of its flour with vinegar topically at the same time. As well as to treat constipation, joint pain, and others. If cooked with water, it softens the throat, chest, and abdomen, soothes coughing, roughness, asthma, and shortness of breath. It is good for colds, phlegm, and hemorrhoids, dissolves sticky phlegm from the chest, and benefits from lung diseases. It is useful from stinging, absolute for the stomach, and if you put it on the cramped nail, you fix it and anointing it is useful if it is mixed with wax from the accidental discord from the cold. The Arabs have known fenugreek since ancient times, and it came in (Dictionary of Food and Medicinal Plants) that Arab doctors used to advise cooking the fenugreek with water to soften the throat, chest and abdomen, and to relieve coughing, shortness of breath and asthma, as it is useful for intestines and hemorrhoids, and also if you cook and wash the hair with it, it makes it curly and beautiful. The fenugreek is a semi-integrated pharmacy for the treatment of diseases. The fenugreek is also included in many areas, including nutritional, therapeutic, drug and esthetic composition. The most prominent

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benefits of the fenugreek are protecting the liver from exposure to cancer, regulating digestion, reducing blood pressure, regulating cholesterol levels in the blood, treating hair loss, regulating levels blood sugar, reduce muscle pain, treat rheumatic disease and also reduce the risk of atherosclerosis (Syed et al., 2020). Fenugreek is a hydrocolloid, it is a soluble fiber in fenugreek that provides textural qualities, attractiveness, thickening, emulsification, stability, crystallization, and encapsulation. Soluble fiber is an essential nutrient. Fenugreek seeds are used directly to manufacture vitamin tablets or capsules that are used in milkshakes, sauces, soups, and desserts, as well as to preserve bakery flour (bread, pizza, cake mix, cakes, noodles, tortillas, baked corn flakes). Fenugreek seed is used in the preparation of flour-based pastry items such as bread and pizza which contains 8%
10% soluble fiber derived from fenugreek (Wani & Kumar, 2018).

9.5 Fenugreek seed composition The fenugreek contains a volatile oil, which consists of hydrocarbon sesquiterpenes, lactones, and alkanes. Fenugreek also contains a large amount of protein, fats, and starch. It also contains the most important minerals, phosphorous, alkaloids such as choline and trigonelline, gum materials, fixed oils, soapy materials, sterols, and soluble sugars such as galactose and mannose. The fenugreek is also an essential source of sporogenin, which is essential in the construction of steroids, and the fenugreek contains dysogenin and lyamogenin. Spogenin, trichoniline, compounds; dysognin, lyamogenin, and soluble sugars, including mannose, galactose, and alkaloids, such as; trigonelline, choline, fixed oils, resins, soaps, fats, starch, sterols, phosphorous, iron, proteins, magnesium, calcium, selenium, zinc, copper, manganese, potassium, sodium, and volatile oils; seskoterpenes, hydrocarbons, alkanes, and lactones (Ahmad et al., 2016). Fenugreek seeds (Fig. 9.2) contain about 0.1%
0.9% of diosgenin, the amount of diosgene reaches 2% if the seeds are grown under optimal conditions then less amounts of FIGURE 9.2 Fenugreek seed and oil. Source: https://commons.wikimedia.org.

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trigogenin and gitonigenin will reported. The seeds contain saponins (Phenogen B), coumarin and a number of alkaloids, including trigonellin, genetinin, and carbine. The seed contains a small amount of fixed and volatile oils, fenugreek seeds contain 0.02%
0.05% volatile oil. The flavor of roasted fenugreek seeds is due to another type of heterocyclic molecule known as pyrazines (Mebazaa et al., 2009).

9.6 Fenugreek seed oil composition The oil can be extracted from fenugreek seeds and it contains antioxidants, and many other components such as unsaturated fatty acids, including linoleic acid, and linolenic acid, and oleic acid (Gu et al., 2017). A laboratory study published in the African Journal of Biotechnology in 2006 indicated that fenugreek oil (Fig. 9.2) may contribute to improving a number of tissues, in addition to stimulating the activity of the ovaries significantly, in mice that took fenugreek oil in different concentrations, for a period of 10 days (Hassan et al., 2006). A laboratory study published in 2010 indicated that the consumption of fenugreek oil in mice with type 2 diabetes may contribute to the improvement of their condition, as it improves the level of sugar and insulin in the blood, in addition, the kidney function of these mice has improved. mice, but it should be noted that there is still a need to confirm these results in humans. In general, people with diabetes are advised to monitor the symptoms of low blood sugar after consuming fenugreek, as it may affect blood sugar levels (http://www.webmd.com). A preliminary study published in 2008 indicated that fenugreek oil has the properties of It is antibacterial and antifungal, and based on this study, fenugreek oil can be used as a preservative in the food industry (Sulieman et al., 2008). Benefits of fenugreek oil for men A small study published in Advances in Life Science and Technology in 2015 indicated that taking fenugreek oil increases Sperm count in men, and the study showed that taking fenugreek oil helps to improve fertility in men, not any other part of fenugreek seeds (Al-Khalisy, 2015).

9.7 Fenugreek antioxidant activity Some research indicated that fenugreek seed oil has good antioxidant activity due to the presence of palmitic acid and phytol because they are well known as powerful and effective antioxidants and have some other biological activities. The results of some research also showed that fenugreek seed oil contains some compounds with antiinflammatory activities. The main components of fenugreek seed oil are linoleic acid, palmitic acid and pine which are very useful in reducing free radicals due to their natural antioxidant properties. Also, the ABTS radical scavenging assay for this oil is more useful compared to the DPPH assay. In general, fenugreek seed oil is effective against many diseases such as cancer, infections, asthma, sexual disorder and urinary tract infections (Akbari et al., 2019). Wound biopsies treated with oils, including fenugreek seed oil, showed better tissue regeneration compared to the control groups. Groups treated with these oils and “CICAFLORA” have a higher rate of wound healing. The polyunsaturated fatty acids in these oils act as mediators of inflammation, increasing angiogenesis, extracellular remodeling,

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migration, and cell differentiation. This study showed that the wound healing effect may be due to the synergistic antibacterial and antioxidant action (Rekik et al., 2016).

9.8 Antibacterial and antifungal effect of fenugreek oil The antimicrobial activity of Fenugreek different parts extract (methanol, acetone, and aqueous extract) against Escherichia. coli and Staphylococcus was investigated by (Sharma et al., 2016). They found that, the maximum zone of inhibition was given by methanol, that is, 20 and 19 mm against E. coli and Staphylococcus, respectively, followed by acetone extract which give the equal zone of inhibition for both organism, that is, 16 mm while the aqueous extract shows nill zone of inhibition. The fenugreek seed oil extracts showed strong antimicrobial effect against three tested bacteria (E. coli, S. aureus, and Salmonella typhimurium) and one mold (Aspergillus niger). The investigation showed an active antimicrobial activity against all tested microorganisms. The highest activity was shown against E. coli at 20 mm inhibition zone and the concentration was 100% while against Aspergillus niger where a complete inhibition (100%) the study concluded that the fenugreek seed oil can be used as an effective antimicrobial which can be used as a food preservative (Sulieman et al., 2018). The fenugreek seed oil showed that activity against E. coli and against Aspergillus niger. The results of the statistical analysis of fenugreek seed oil showed high activity against E.coli and against Aspergillus niger and that, concentrated oil improves the shelf life of food. In comparison of fenugreek seed oil as antimicrobial with antibiotics, the results showed that the test microbes used in the study had a clear resistance to most of the antibiotics used despite the high concentration used, and there is a superiority in the inhibitory effect of 100% fenugreek seed oil against the test isolates used (Hadi et al., 2018).

9.9 Conclusion Fenugreek oil is extracted from fenugreek seeds. These seeds are very nutritious and also have a variety of health benefits. Fenugreek seed oil has many effective health benefits it is a powerful antioxidant, thus it helps prevent many tissues and cells from oxidizing.

References Acharya, S. N., Thomas, J. E., & Basu, S. K. (2006). Fenugreek: an “old world” crop for the “new world,”. Biodiversity, 7(3
4), 27
30. Available from https://doi.org/10.1080/14888386.2006.9712808. Ahmad, A., Alghamdi, S. S., Mahmood, K., & Afzal, M. (2016). Fenugreek a multipurpose crop: Potentialities and improvements. Saudi Journal of Biological Sciences, 23(2), 300
310. Available from https://doi.org/10.1016/j. sjbs.2015.09.015. Akbari, S., Abdurahman, N. H., Yunus, R. M., Alara, O. R., & Abayomi, O. O. (2019). Extraction, characterization and antioxidant activity of fenugreek (Trigonella-foenum graecum) seed oil. Materials Science for Energy Technologies, 2(2), 349
355. Al-Khalisy, M. (2015). Treatment of men infertility using low doses of fenugreek oil extract. Advances in Life Science and Technology, 29.

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Amin, A., Alkaabi, A., Al-Falasi, S., & Daoud, S. A. (2001). Chemopreventive activities of Trigonella foenumgraecum (Fenugreek) against breast cancer. Cell Biology International, 29, 687
694. Gu, L. B., Liu, X. N., Liu, H. M., Pang, H. L., & Qin, G. Y. (2017). Extraction of fenugreek (Trigonella foenumgraceum L.) seed oil using subcritical butane: Characterization and process optimization. Molecules (Basel, Switzerland), 22(2), 228. Hadi, S. T., Abed, M. M., & Fadhil, N. J. (2018). Chemical composition of Trigonella foenum-graecum seeds and inhibitory activity of their seeds oil against some microbes. International Journal of Life Sciences and Biotechnology, 1(2), 75
83. Hassan, A. M., Khalil, W. K. B., & Ahmed, K. A. (2006). Genetic and histopathology studies on mice: Effect of fenugreek oil on the efficiency of ovarian and liver tissues. African Journal of Biotechnology, 5(5), 477
483. Kumar, M., Parsad., & Marya, R. K. (2013). Grain yield and quality improvement in fenugreek: A review. Forage Research, 39(1), 1
9. Lust, J. B. (1986). The Herb Book. New York: Bantam Books Inc. Mebazaa, R., Mahmoudi, A., Fouchet, M., Kamissoko, F., Dos Santos, M., Rega, B., Nafti, A., Ben Cheikh, R., & Camel, V. (2009). Characterization of volatile compounds in Tunisian fenugreek seeds. Food Chemistry, 115(4), 1326
1336. Available from https://doi.org/10.1016/j.foodchem.2009.01.066. Naidu, M. M., Shyamala, B. N., Naik, J. P., Sulochanamma, G., & Srinivas, P. (2011). Chemical composition and antioxidant activity of husk and endosperm of fenugreek seeds. LWT Food Science Technology, 44, 451
456. Rekik, D. M., Khedir, S. B., Moalla, K. K., Kammoun, N. G., Rebai, T., & Sahnoun, Z. (2016). Evaluation of wound healing properties of grape seed, sesame, and fenugreek oils. Evidence-Based Complementary and Alternative Medicine, 2016, Article ID 7965689, 12 pages, 2016. Sharma, V., Singh, P., & Rani, A. (2016). Antimicrobial activity of Trigonella foenum-graecum L. (Fenugreek). European Journal of Experimental Biology., 7, 1. Sulieman, A. M., Ahmed, H., & Abdelrahim, A. (2008). The chemical composition of fenugreek (Trigonella foenum graceum L) and the antimicrobial properties of its seed oil. Gezira Journal of Engineering and Applied Sciences, 2(3), 52
71. Syed, Q. A., Rashid, Z., Ahmad, M. H., Shukat, R., Ishaq, A., Muhammad, N., & Ubaid Ur Rahman, H. (2020). Nutritional and therapeutic properties of fenugreek (Trigonella foenum-graecum): A review. International Journal of Food Properties, 23(1), 1777
1791. Available from https://doi.org/10.1080/10942912.2020.1825482, http:// www.webmd.com. Retrieved on 18.07.2021. Wani, S. A., & Kumar, P. (2018). Fenugreek: A review on its nutraceutical properties and utilization in various food products. Journal of the Saudi Society of Agricultural Sciences, 17(2), 97
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C H A P T E R

10 Antiinflammatory, antimicrobial, and allelopathic activities of some cucurbit seed oils Ogueri Nwaiwu1,2 and Abdalbasit Adam Mariod3,4 1

Department of Food Nutrition and Dietetics, School of Biosciences, The University of Nottingham, Sutton Boninton Campus, LE12 5RD, Nottingham, United Kingdom 2Alpha-Altis (Venture Member), Ingenuity Lab, The University of Nottingham, Jubilee Campus, Nottingham, United Kingdom 3Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 4College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia

10.1 Introduction The cucurbit family plants are very active in their growth. Its leaves are huge and its blossoms are yellow and trumpet-like. Cucurbitaceae plants require a lot of space, so the climbing varieties can be perched in order to grow vertically, while the nonclimbing varieties are less spread out. This family is famous for its fruits, so cucurbits—mostly—are grown to benefit from their fruits, mainly, and to a lesser extent, their flowers and even their seeds are edible. The genus Cucurbita is known for its traditional or folklore history and treatment of many medical disorders due to chemical compounds present, which produce a specific physiological effect in the human body (Salehi, Capanoglu, et al., 2019). The various parts of the plant like the seeds have been reported to have various medical, nutritional, and antimicrobial properties. These seeds have also been reported (Lacatusu et al., 2018) to have a noninvasive photoprotection property that could reduce the occurrence of skin cancer and delay the process of photoaging. Since pumpkin seeds have shown the potential of reducing microbial infections, it has been proposed by Dotto and Chacha (2020) that they can potentially serve as a functional food ingredient. This proposal came with a condition that more animal and clinical trials

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are carried out to establish the respective molecular mechanisms and safety profile of the product. Regardless of the safety concerns, Patel and Rauf (2017) suggested that the seeds are underutilized and can be used to formulate a myriad of nutraceuticals. Cucumber seed oil is obtained from the cold pressing of the seeds. It is a stable and nonvolatile oil because it contains a high percentage of linoleic acid, oleic acid, and phytosterols. It can be applied to the skin without using a carrier oil, however, dilution is required to reduce the strenth of the seed oil.. The oil is used in the treatment of various skin diseases, bacterial infections, respiratory infections, digestive problems, infections, edema, fever, constipation, arthritis, gout, obesity, hair loss, and diabetesdue to its antibacterial, anticarcinogenic, antioxidant, rheumatic, antiseptic, stress resistance, ulcer resistance, diuretic and laxative properties. Cucumber seed oil contains many nutrients such as phytosterols, tocopherols, various vitamins and minerals, and essential fatty acids such as vitamin B, linoleic acid, magnesium, oleic acid, omega-3 acid, palmitic acid, potassium, sodium, vitamin C, and vitamin E (Sharma et al., 2020). Massaging the joints with cucumber seed oil helps reduce the inflammation and swelling that the joints suffer from. Mixing a teaspoon of cucumber seed oil with half a tablespoon of coconut oil and four drops of ylang ylang essential oil is very effective in reducing arthritis and relieving pain. You can use cucumber seed oil in the treatment of gout because it may act as a pain reliever and has temporary anesthetic properties that relieve pain quicklywhile the antiinflammatory properties of cucumber seed oil reduce inflammation and fluid build-up in the joints (Choe et al., 2018). Watermelon seed oil is extracted by drying watermelon seeds, followed by roasting before subjectingthe roasted seeds to cold pressing operations. Watermelon seed oil contains many important nutrients for health, body, and skin. Watermelon seed oil is distinguished by a light smell similar to nuts and is characterised by a light yellow color, . It is easily absorbed by the skin and can be used in cooking processes because of its large number of fatty acids. It can also be used topically or internally. Watermelon seed extracts and oil have been used for many years in biological activities that are antibacterial and antifungal, and have been used as an antiulcer andantiinflammatory agent. (Alka et al., 2018). A study by Periˇcin et al. (2009) found that phenolic compounds are widely distributed in pumpkin’s hull-less seed, skin, oil cake meal, dehulled kernel, and hull.

10.2 Antiinflammatory activities of some cucurbits oil Amin et al. (2020) have assessed the antiinflammatory, antioxidant and antibacterial properties of hybrid and indigenous varieties of pumpkin (Cucurbita maxima Linn.) seed oil. They found that pumpkin seed oil (PSO) has antiinflammatory, antioxidant, and antibacterial activities, and could be a promising source of ingredients in the food and pharmaceutical industries. Applying 2% cucumber seed oil to inflammatory areas provides relief and has a good effect on reducing inflammation. Al-Okbi et al. (2017) evaluated the antiinflammatory activity of PSOs, in a rat model for treating adjuvant arthritis. They identified edema thickness, plasma tumor necrosis factor α (TNF-α), and erythrocyte sedimentation rate (ESR) as inflammatory biomarkers while malondialdehyde (MDA) and total antioxidant capacity (TAC) were evaluated as evidence of oxidative stress. Their results showed elevated ESR, plasma TNF-α, plasma MDA, hepatic cellular DNA fragmentation, chromosomal aberration

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in the bone marrow, and sperm morphology abnormalities with decreased plasma TAC and increased body weight in samples from infected mice compared to healthy ones. Bitter melon oil is also believed to be an effective treatment that prevents hair loss, imparts blackness to hair, delays the emergence of gray hair, treats dandruff infections, eliminates lice, and bitter melon oil is useful in treating alopecia areata, health problems, kidney disease, cystitis, scorpion stings, treatment of hemorrhoids, nausea, anemia, burns, headaches, and liver diseases. Bitter melon Citrulus colocynthis seed oil is used to treat skin diseases and it can be applied to the skin with some massage, and the oil can be used to treat some sores. Bitter melon could also be used for the treatment of joint pain and rheumatism. The bitter melon fruit is grilled on the fire, then sprinkled and put hot on the place of treatment. Bitter melon is used in the treatment of nerve pain, and gout, and its leaves are used to control bleeding (http://www.hort.purdue.edu). Watermelon seed oil is known to contain various minerals, antioxidants, and unsaturated fatty acids such as oleic acid, omega-3 and -6, as well as various vitamins to moisturize dry skin. It is also an excellent carrier oil capable of delivering other active ingredients and nutrients to deeper layers of the skin. With melon seed oil containing a fair amount of antioxidants, including phenolics, lycopene, and carotenoids, this oil is able to reduce the appearance of wrinkles, age spots, and skin blemishes. Applying watermelon seed oil to inflamed areas such as psoriasis, rosacea, eczema, or acne spots can quickly reduce the inflammatory irritation and treat any underlying infection that this inflammation may cause. Studies have found that the topical or internal use of this oil can help remove toxins from the body, by removing dead pores, stimulating liver function, and keeping the body free of toxins inside and out. This oil is also known to be a diuretic, which also helps to reduce and flush out toxins from the body. Applying this oil to the hair can improve its shine, reduce scalp inflammation, and strengthen the follicles due to high levels of vitamin E and antioxidants (Athar et al., 2020).

10.3 Overview of antimicrobial activity of cucurbits seed oil Hammer et al. (1999) showed that Aeromonas was sensitive to oil extracted from Cucurbita pepo. The antimicrobial reports of Cucurbita spp. against Aeromonas spp. are few in literature, so more work needs to be carried out. Candida albicans is a polymorphic fungus and a member of the normal human microbiome but it can cause infections under certain circumstances (Mayer et al., 2013). Basmaciyan et al. (2019) pointed out that the gastrointestinal tract is the main source of disseminated C. albicans infections. Unirradiated Cucurbita moschata oil has been shown to have antifungal activity against C. albicans (Abd El-Aziz & Abd El-Kalek, 2011), whereas Sood et al. (2012) found that C. pepo extract did not show any inhibition. The antimicrobial effect of the PSO is usually determined by finding the minimal inhibitory concentration or diameter of inhibition in diffusion studies performed in clinical investigations. Many studies in the literature that reported the antimicrobial efficacy of pumpkin seeds used disk diffusion as a method of analysis. Usually, extraction is carried out with hot water, ethanol, or methanol. Investigators show that after obtaining the seed oil extract, a disk from a filter paper is prepared following which they are soaked in the

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extract and then used for diffusion assays. The zone of inhibition in millimeters is noted after incubation and most authors propose that the extract used is antimicrobial even if the zone of inhibition achieved is very low. The zones of inhibition against microorganisms achieved by seed extracts of different pumpkin species was reported in a comprehensive review (Salehi, Sharifi-Rad, et al., 2019). To get an overview of the antimicrobial property of PSO, a comparison of the zones of inhibition and the standard for similar microorganisms was carried out in line with the interpretive categories and zone diameter breakpoints of different antimicrobial drug classes. Overall, the sensitive zones of inhibition diameter (mm) achieved with different antimicrobial agents ranged from 15 to 23 (disk content # 0.35 mg). In the studies with Staphylococcus spp. (Abd El-Aziz & Abd ElKalek, 2011) achieved 10 mm zone of inhibition (150 mg), whereas Ravishankar et al. (2012) reported 15 mm (100 mg) and 16 mm (200 mg). Considering that the concentration of the antimicrobial agent used in these PSO studies was far higher than the ones used to establish the efficacy of known antimicrobials, it may be safe to conclude that the extracts from Cucurbita spp. seeds have less sensitivity to Staphylococcus spp. than classical antimicrobial drug classes. It will be interesting to establish if any inhibition can be achieved with the low concentrations used if they are used to test the efficacy of pumpkin seed extract. More studies need to be carried out clinically to establish the effective dose of PSO on undesirable microorganisms present in humans.

10.4 Allelopathic activities of some cucurbits oil The term “allelopathy” refers to the harmful or beneficial effect of one plant on another as a result of the production and release of its metabolites into the environment. Like all components of other biological systems, these metabolites are divided into two parts. The first section includes chemicals that determine growth and development, such as carbohydrates, proteins, and fats. The second section includes secondary metabolites whose mission is to increase the ability of plants to withstand difficult environmental conditions (Findura et al., 2020). To reduce the use of chemical pesticides harmful to the soil and the environment and to control weeds, it is better to rotate crops or follow intercropping with allelopathic crops. Oilseed crops like soybean, sesame, sunflower, and Brassica crops have the ability to stop or prevent the growth of weeds because it produces different compounds in the air and its roots. Allelopathic plants offer a new way to discover natural pesticides (Shah et al., 2016). Under laboratory conditions, the allelopathic activity of pumpkin extracts (C. pepo L.) with normal hexane, ethyl acetate, and water obtained from C. pepo L. leaf extracts were studied, with knowledge of their effect on germination of seeds of Zea mays and three types of weeds. The results showed that hexane extracts, water and ethyl acetate were the most toxic against weeds, and that the hexane fraction was the most selective between the Z. mays L. hybrid and weed species, while the remaining parts had high selectivity among them. In contrast, all parts of C. pepo L. extract had moderate to slight toxicity against both weeds and maize plants (AbdAllah & Amine, 2016).

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10.5 Conclusion Cucurbits oils (pumpkin, cucumber, watermelon, and melon) contain many compounds with biological activity, which enhances the opportunity to use them as antiinflammatory, antimicrobial, and allelopathic drugs., This provides the capability for possible application in the production of new drugs, antidiabetic foods, analgesics, antiinflammatory, and prevention of heart disease. This review highlights that cucurbits have protective and therapeutic capabilities.

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119. AbdAllah, S. A., & Amine, H. M. (2016). Effects of Cucurbita pepo L. and Eucalyptus citriodora plant extract fractions on seed germination of corn and some associated weeds. Tanta University Journal of Environment (9), 220
227, Special Issue. Alka, G., Anamika, S., & Ranu, P. (2018). A review on watermelon (Citrullus lanatus) medicinal seeds. Journal of Pharmacognosy and Phytochemistry, 7(3), 2222
2225. Al-Okbi, S. Y., Mohamed, D. A., Kandil, E., Abo-Zeid, M. A., Mohammed, S. E., & Ahmed, E. K. (2017). Antiinflammatory activity of two varieties of pumpkin seed oil in an adjuvant arthritis model in rats. Grasas Aceites, 68, e180. Available from http://doi.org/10.3989/gya.0796161. Amin, M. Z., Rity, T. I., Uddin, M. R., Rahman, M. M., & Uddin, M. J. (2020). A comparative assessment of antiinflammatory, anti-oxidant and anti-bacterial activities of hybrid and indigenous varieties of pumpkin (Cucurbita maxima Linn.) seed oil. Biocatalysis and Agricultural Biotechnology, 28, 101767. Available from https://doi.org/10.1016/j.bcab.2020.101767. Athar, S., Ghazi, A., Chourasiya, O., & Karadbhajne, V. Y. (2020). Watermelon seed oil: Its Extraction, analytical studies, modification and utilization in cosmetic industries international research. Journal of Engineering and Technology (IRJET), 7(2), 2862
2865. Basmaciyan, L., Bon, F., Paradis, T., Lapaquette, P., & Dalle, F. (2019). Candida albicans interactions with the host: Crossing the intestinal epithelial barrier. Tissue Barriers, 7(2), 1612661. Available from https://doi.org/ 10.1080/21688370.2019.1612661. Choe, U., Li, Y., Gao, B., Yu, L., Wang, T. T. Y., Sun, J., Chen, P., Liu, J., & Yu, L. (2018). Chemical compositions of cold-pressed broccoli, carrot, and cucumber seed flours and their in vitro gut microbiota modulatory, antiinflammatory, and free radical scavenging properties. Journal of Agricultural and Food Chemistry, 66(35), 9309
9317. Dotto, J. M., & Chacha, J. S. (2020). The potential of pumpkin seeds as a functional food ingredient: A review. Scientific African, 10, e00575. Available from https://doi.org/10.1016/j.sciaf.2020.e00575. Findura, P., Hara, P., Szparaga, A., Kocira, S., Czerwi, E., Bartoˇs, P., Nowak, J., & Treder, K. (2020). Evaluation of the effects of allelopathic aqueous plant extracts, as potential preparations for seed dressing, on the modulation of cauliflower seed germination. Agriculture, 10, 122. Available from https://doi.org/10.3390/ agriculture10040122. Hammer, K. A., Carson, C. F., & Riley, T. V. (1999). Antimicrobial activity of essential oils and other plant extracts. Journal of Applied Microbiology, 86(6), 985
990. Lacatusu, I., Arsenie, L. V., Badea, G., Popa, O., Oprea, O., & Badea, N. (2018). New cosmetic formulations with broad photoprotective and antioxidative activities designed by amaranth and pumpkin seed oils nanocarriers. Industrial Crops and Products, 123, 424
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14867, 10.1007/s11356-016-6969-6. Sharma, V., Sharma, L., & Sandhu, K. S. (2020). Cucumber (Cucumis sativus L.). In G. A. Nayik, & A. Gull (Eds.), Antioxidants in vegetables and nuts - Properties and health benefits. Singapore: Springer. Available from https:// doi.org/10.1007/978-981-15-7470-2_17. Sood, A., Kaur, P., & Gupta, R. (2012). Phytochemical screening and antimicrobial assay of various seeds extract of Cucurbitaceae family. International Journal of Applied Biology and Pharmaceutical Technology, 3, 401
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C H A P T E R

11 Cucumis melo L. seed oil components and biological activities Mafalda Alexandra Silva1,2, Taˆnia Gonc¸alves Albuquerque1,2,3, Rita Carneiro Alves2, M. Beatriz P.P. Oliveira2 and Helena S. Costa1,2 1

Department of Food and Nutrition, National Institute of Health Dr. Ricardo Jorge, I.P., Lisbon, Portugal 2REQUIMTE-LAQV/Faculty of Pharmacy of University of Porto, Porto, Portugal 3Instituto Universita´rio Egas Moniz, Lisbon, Portugal

11.1 Introduction Nowadays, the production levels of food waste and its removal are one of the biggest concerns that the world needs to face. Each year, about 1.6 billion tons of produced fruits are lost or wasted, according to Food and Agriculture Organization (Bellu`, 2017). The peels and seeds discarded in the environment, produced in large quantities, with high concentrations of organic compounds and biologically unstable, are a major concern worldwide. In addition, the expenditure to dry, store, and transport the food industry by-products are a source of costs for companies. Besides, these food by-products are a good source of bioactive compounds, with beneficial properties to human health, and reported as useful in the food, pharmaceutical, and cosmetic industries (Campos et al., 2020; Helkar et al., 2016; Bellu`, 2017; Ferrentino et al., 2018; Vinha et al., 2020; Nunes et al., 2020; Gonza´lez et al., 2019; Barreira et al., 2019; Machado et al., 2019; Nunes et al., 2019). Cucumis melo L. is a well known and consumed fruit all over the world. Its processing produces a wide range of food products such as juices, nectars, jam, and dehydrated pulp, which generates a large amount of food by-products. To take advantage of melon byproducts, in recent years, many reviews have been published related to its valorization (Silva et al., 2020; Go´mez-Garcı´a et al., 2020; Rolim et al., 2020; Qian et al., 2019; Rabada´n et al., 2020). Recently, interest in fruit seeds has grown, essentially due to their bioactive compounds and their nutritional and medicinal properties. C. melo L. seeds represent

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approximately 10% of their weight (Rashid et al., 2011). In Tunisia and some African countries, melon seeds are consumed directly as snacks, after salting and/or roasting. They are also incorporated, after drying, as flavoring of Indian dishes and desserts (Maran & Priya, 2015; Maynard & Maynard, 2000). Several studies have shown that C. melo L. seeds contain many nutrients such as protein, fiber, minerals, and amino acids (Mallek-Ayadi et al., 2017, 2018; Morais et al., 2017; Petkova & Antova, 2015; Azhari et al., 2014; Hu & Ao, 2007). In addition, they have also been reported to have antioxidant (Rolim et al., 2018), antiinflammatory (Bouaziz et al., 2020), antibacterial (Silva et al., 2018), antiangiogenic (Rasouli et al., 2017), antiulcer (Gill et al., 2011) and antidiabetic (Chen et al., 2013, 2014) activities. Therefore, due to its high oil content (29%
31%) (Mallek-Ayadi et al., 2018; Azhari et al., 2014), melon seeds can be an alternative source of vegetable oil, rich in bioactive compounds and natural antioxidants (Aminu et al., 2020). Thus, the use of natural raw materials, such as melon seeds, may be one of the solutions for industries to face the current demand for new vegetable oils. This chapter provides an overview of the main described compounds in melon seed oil and their beneficial health effects.

11.2 Botanical, morphology, and cultivation Cucurbitaceae family has an important economic role since most of its species are ingredients of various food products, such as cucumbers, squash, pumpkins, watermelon, and melon (ITIS, 2017; Vishwakarma et al., 2017). C. melo L. is one of the most diversified species belonging to the genus Cucumis (Table 11.1), due to the great variation of morphological characteristics of its fruits, such as size, texture, shape, color, and flavor. Its size can vary between an olive and a gourd; some can be egg-shaped or globular; the peel can be ribbed or smooth and with several colors. The pulp is not always sweet and can be white, TABLE 11.1

Taxonomic classification of Cucumis melo L. (ITIS, 2017).

Rank

Scientific name

Kingdom

Plantae

Subkingdom

Viridiplantae

Super division

Embryophyta

Division

Tracheophyta

Class

Magnoliopsida

Super order

Rosanae

Order

Cucurbitales

Family

Cucurbitaceae

Genus

Cucumis

Species

Cucumis melo L.

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green, or orange (Preeti & Raju, 2017). It is a very popular fruit, consumed in large areas of the world, especially due to its excellent flavor qualities and freshness. It requires rich and well-drained soil, warm arid conditions, and sunny locations, and grows in Europe, Asia, and Africa (Kapoor et al., 2020).

11.3 Melon seed oil composition Several fruit seeds have been studied for the extraction of their vegetable oils, rich in valuable bioactive and antioxidant compounds. These compounds are responsible for the positive influence that melon seed oil can have on disease prevention and health promotion. The following subsections describe the main compounds available in melon seed oil, reported in literature.

11.3.1 Fatty acids The fatty acid profile of an oil is a very important marker of its nutritional value. There are many studies related to the fatty acid profile of melon seed oil, due to a very interesting fatty acid composition. The main fatty acids are linoleic acid (33%
69%), followed by oleic (15%
32%), palmitic (5%
16%) and stearic acids (3%
12%). Analyzing the data reported by several authors, linoleic and oleic acids together represent about 85% of the total fatty acids of the oil, assigning it a linoleic-oleic oil designation (Ahmad et al., 2019; ´ Akkemik et al., 2019; Azhari et al., 2014; Go´rna´s & Rudzinska, 2016; Hashemi et al., 2017; Mallek-Ayadi et al., 2018; Mariod et al., 2009; Ouattara et al., 2015; Petkova & Antova, 2015; Rezig et al., 2019; Silva & Jorge, 2017; Rabada´n et al., 2020; Mariod & Mattha¨us, 2008). Regarding linoleic acid, it has some favorable nutritional implications in the human body and, eventually, some beneficial effects in the prevention of coronary heart disease and cancer (Carvalho et al., 2011; Oomah & Godfrey, 2000). However, a high content of linoleic acid makes the oil more susceptible to oxidation, being extremely important to preserve it in the most appropriate conditions (Oomah & Godfrey, 2000). On the other hand, the natural presence of compounds with high antioxidant capacity, such as phenolic compounds and vitamin E, may contribute positively to the oxidative stability of the oil. As previously referred, melon oil has a very high content of unsaturated fatty acids, especially omega 6. As human body is not able to produce polyunsaturated fatty acids, these nutrients need to be supplied by diet, what is done by fruit seed oils, namely melon seed oil. This high content of polyunsaturated fatty acids gives melon seed oil potential beneficial effects on human health. They are a group of phytochemicals related to a preventive role in cardiovascular diseases, a beneficial effect in total cholesterol content and decrease in low-density lipoprotein cholesterol, to improve the immune response and mitigation of the oxidative stress caused by diabetes mellitus (Silva et al., 2021; Pariza et al., 2001; Suresh & Das, 2003; Ajayi & Ajayi, 2009). Dubois et al. (2007) studied the fatty acid profile of the most commercially used vegetable oils. Comparing the fatty acid profile of melon seed oil with other vegetable oils, similarities with soybean and sunflower oils, highly commercialized oils, are evident. The same study also compares the fatty acid profile of other oils extracted from fruit seeds.

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This is the case of similarities between pumpkin and watermelon seed oils, fruits belonging to the same family of melon (Dubois et al., 2007). Thus, in what concerns to the fatty acids composition, the melon seeds oil has a quality similar to others commonly available in the market, although it is not yet commercialized by the food industry.

11.3.2 Vitamin E Tocochromanols (tocopherols and tocotrienols) are lipid-soluble molecules that belong to the group of vitamin E, whose main source are oils and derived compounds. As natural antioxidants, they protect unsaturated fatty acids from oxidation and ensure the stability of lipid membranes. They are well known for their essential role in human health, being related to cancer prevention and reducing the risk of cardiovascular and Alzheimer diseases (Nyam et al., 2009). Thus, a high content of tocopherols is a desirable characteristic for the possible use of fruit seeds oil by the food industry (Karrar et al., 2019; Go´rnas et al., 2014). α-tocopherol is the most biologically active and essential form for oil quality, while γ-tocopherol is considered the best antioxidant, inhibiting lipid oxidation by stabilizing hydroperoxides and other free radicals (Dias et al., 2013). In addition, some studies have reported that α-tocopherol has analgesic and antiinflammatory activities, and γ-tocopherol has antiinflammatory activity, as well as it can play an important role in the prevention and delayed healing of wounds in diabetes and in reducing the risk of thrombotic events (Zheng et al., 2020; Juaira et al., 2018; Singh et al., 2007). The melon seed oil is rich in vitamin E (23
72 mg/100 g), being γ-tocopherol (10
63 mg/ 100 g) the major vitamer available (Rabada´n et al., 2020; Go´rna´s et al., 2015; Mallek-Ayadi et al., 2018; Mariod & Mattha¨us, 2008, 2009; Silva & Jorge, 2017). Rabada´n et al. (2020) studied the content of vitamin E and its vitamers present in seed oils of nine different varieties of melon. The main vitamer present in all oils analyzed was γ-tocopherol, with levels that varied from10 mg/100 g for tendral valenciano to 46 mg/100 g for honey dew, followed by α-tocopherol with levels that ranged from 3.7
7.5 mg/100 g, for arizo and tendral valenciano varieties, respectively. In the same study, the presence of δ-tocopherol (1.3
2.7 mg/100 g) was also reported. Regarding tocotrienols, the authors identified α-tocotrienol, β-tocotrienol, and γ-tocotrienol. In fact, tocotrienols sometimes exhibit greater antioxidant activity than their corresponding tocopherols and are described to function in breast cancer reduction and cholesterol biosynthesis inhibition (Shahidi et al., 2016; Schwenke, 2002). Compared with other fruit seeds, melon seed oil has α-tocopherol contents higher than pumpkin, grape, guava, mango, and soursop seeds oil and -tocopherol levels higher than apple, grape, guava, passion fruit, soursop, and strawberry seed oils (Silva & Jorge, 2017). In addition, when compared to watermelon seed oil, melon seed oil has higher levels of α-tocopherol and α-tocotrienol (Go´rna´s et al., 2015). This analysis confirms melon seed oil as a rich source of tocopherols and tocotrienols, with expectable biological activities and potential benefits for human health.

11.3.3 Phytosterols Phytosterols are part of the cell membranes of plants and its best-known sources are vegetable oils. As they are not synthesized by the human body, they must be consumed in

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the diet. There is a great diversity of phytosterols, but the more common in nature and in food are β-sitosterol, campesterol, stigmasterol and avenasterols. Some phytosterols are related to the reduction of absorbed cholesterol levels by the intestine and to the decrease of low-density lipoprotein blood levels, since they are structurally similar to cholesterol. Thus, several recent studies report the purification of phytosterols and phytostanols and their incorporation into foods, to obtain functional foods, with for example hypocholesterolemic activity (Lichtenstein & Deckelbaum, 2001; Silva & Jorge, 2017; Ogbe et al., 2015). In addition, the sterols profile is used to track commercial fraud and to determine the quality of vegetable oil, as this parameter functions as fingerprint of them (Mallek-Ayadi et al., 2018). The main sterol present in melon seed oil is β-sitosterol (206
325 mg/100 g). Δ5-avenasterol is the following with levels from 2.2 to 153 mg/100 g (Silva & Jorge, 2017; Rezig et al., 2019; Mallek-Ayadi et al., 2018; Azhari et al., 2014; Petkova & Antova, 2015; Mariod & Mattha¨us, 2008). In some studies, these two sterols represent about 90% of the total sterols (Rezig et al., 2019; Azhari et al., 2014; Petkova & Antova, 2015; Mariod & Mattha¨us, 2008). Additionally, some authors also reported interesting levels of other compounds such as Δ5,24-stigmastadienol (118 mg/100 g), stigmastanol (117 mg/100 g), Δ7stigmasterol (14 mg/100 g), sitostanol (11 mg/100 g) and Δ7-campesterol (15 mg/100 g) (Silva & Jorge, 2017; Rezig et al., 2019; Mallek-Ayadi et al., 2018). β-sitosterol has been widely studied and linked to numerous benefits for human health such as analgesic, antimicrobial, anticancer, antiinflammatory, antioxidant, and antidiabetic activities (Dighe et al., 2016; Ododo et al., 2016; Sharmila & Sindhu, 2017; Paniagua-Pe´rez et al., 2017; Gupta et al., 2011; Babu et al., 2020). On the other hand, Δ5-avenasterol is known for its antioxidant capacity and its role in lipids protection against oxidative polymerization during frying (Mariod & Mattha¨us, 2008). Comparing to other fruit seed oils, melon seed oil has higher levels of β-sitosterol than citron, kumquat, mango, orange, passion fruit, soursop, and pumpkin oils (Silva & Jorge, 2017). On the other hand, in comparison with other species of the same family, it presents higher levels of total sterols than pumpkin and higher levels of total sterols, β-sitosterol and Δ5-avenasterol than the watermelon seed oil (Silva & Jorge, 2017; Angelova-Romova et al., 2019; Rezig et al., 2019). Based on data reported, some varieties of melon contain higher levels of β-sitosterol in its seed oil than some marketed vegetable oils, such as soybean, sunflower and flaxseed oils (Yang et al., 2019). Therefore, melon seed oil is a rich source of sterols, especially β-sitosterol, with beneficial health properties, comparatively to other vegetable oils. A potential application could be for example as antihypercholesterolemic agent.

11.3.4 Phenolic compounds Phenolic compounds are determinant for some of the main characteristics of oils, such as taste, oxidative stability, shelf life as well as their overall quality. These compounds exhibit biological properties attributed to their antioxidant activities. Some studies report the addition of phenolic compounds to foods, as natural antioxidants, to prevent the development of undesirable flavors (Hoed, 2010). As previously referred in the fatty acid profile, melon seed oil is rich in polyunsaturated fatty acids, feature related to high

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susceptible to oxidation. The natural presence of phenolic compounds may prevent the oxidation of fatty acids, through the beneficial effect on the oxidative stability of vegetable oils. Furthermore, phenolic compounds can exhibit a positive effect in the prevention of cancer and cardiovascular diseases (Mallek-Ayadi et al., 2019). The main phenolic compounds identified in melon seed oil were ferulic acid (135 μg/g), amentoflavone (33 and 39 μg/g), pinoresinol (11 μg/g), luteolin-7-O-glycoside (10 and 13 μg/g), gallic acid (7.3 and 9.3 μg/g) and callistephin (27.5 and 30.6%) (Mariod & Mattha¨us, 2008; Mallek-Ayadi et al., 2019; Rezig et al., 2019). Many of these compounds have beneficial health properties. For example, gallic acid, one of the most well-known phenolic acids, has antifungal, antiinflammatory and antioxidant properties, protecting cells against the oxidation. It is also used as an additive in processed foods to prevent its deterioration and prevent rancidity/lipid peroxidation (Kahkeshani et al., 2019). To decrease the use of synthetic preservatives in the food industry, ferulic acid is widely used due to its antioxidant properties and antimicrobial activity (Batista, 2014). Pinoresinol has antiinflammatory activity (During et al., 2012) and callistephin may have an important role in the treatment of neurodegenerative diseases associated with microglial activation (Zhao et al., 2019). Flavonoids are bioactive compounds whose beneficial effects are also essentially due to their antioxidant activity. Amentoflavone, one of the flavonoids detected in melon seed oil, is reported to have antidiabetic activity and to be a potential adjunct in the treatment of patients with glioblastoma. Luteolin-7-O-glycoside has been associated with the treatment of inflammatory skin diseases such as psoriasis (Su et al., 2019; Yen et al., 2018; Palombo et al., 2016). Additionally, the presence of oleuropein in melon seed oil, confers similarity with olive oil, once it is one of the main phenolic compounds in such fruit juice. Oleuropein is linked to beneficial effects for patients with Alzheimer’s disease (Cordero et al., 2018). Therefore, melon seed oil is a good source of natural antioxidants, with various biological activities, beneficial to human health and can play a very important role in decreasing the risk of certain diseases. Furthermore, due to the great antioxidant power of these compounds, they can protect the oil from oxidation of polyunsaturated fatty acids, thus preserving its quality.

11.4 Biological activities The chemical composition, previously described, allows foresight melon seed oil as a relevant source of fatty acids, vitamin E, phenolic compounds and phytosterols. The following subsection describes the influence of these compounds on disease prevention and health promotion.

11.4.1 Antioxidant activity The antioxidant power attributed to melon seed oil is essentially due to the presence of specific compounds, namely phytosterols, vitamin E, phenolic compounds, and fatty acids.

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These compounds can protect the biological systems of reactive oxygen species, preventing some chronic diseases, such as cardiovascular disease and cancer. Azhari et al., 2014 evaluated the antioxidant activity of melon seed oil through four assays: reducing power, β-carotene bleaching inhibition activity, ABTS and DPPH radical scavenging activities. The results found were IC50 of 25 mg/mL for DPPH• inhibition assay, and IC50 of 23 mg/mL for ABTS scavenging activity. Regarding results obtained for DPPH radical scavenging activity, they were higher than the used control (ascorbic acid) which was 14 mg/mL. The same was found for ABTS assay, whose result obtained for BHT (reference) was 11 mg/mL. The absorbance results of reducing power assay varied from 0.04 for the concentration of 5 mg oil equivalents/mL and 0.63 for 25 mg oil equivalents/mL. The reference used for this test was ascorbic acid, whose absorbance was 1.3 for 0.5 mM. The results obtained for melon seed oil were significantly lower, compared to the reference. Regarding the results of β-carotene bleaching inhibition activity, after 90 min, the obtained absorbance was 0.28 for melon seed oil (0.95 mg/mL) and 0.48 for the reference (BHT, 0.95 mg/mL). Rezig et al., 2019 determined the DPPH• inhibition of methanolic extracts from three types of Curcubitaceae seed oils (pumpkin, watermelon and melon). IC50 values of 53 μg/ g were obtained for Cucumis melo var. “Ananas” seed oil, 65 μg/g for Cucurbita pepo var. ‘Essahli’ seed oil and 160 μg/g for Citrullus lanatus var. “Crimson” seed oil. The melon seed oil showed the highest antioxidant activity. The authors, with these results, also verified a relationship between the antioxidant activity and the oil stability index since the melon seed oil also showed greater stability against oxidation. According to the authors, the tocochromanols content in the analyzed seeds oils can be a possible justification for the different results of antioxidant activity observed. In fact, Go´rna´s et al. (2015) described a significant relationship between the tocochromanols content in the oils of various seeds and the DPPH radical scavenging activity.

11.4.2 Antiinflammatory activity Inflammation results from a microbial infection or occurs in response to determined processes, such as injuries, cell death or degeneration (Azab et al., 2016). As referred in this chapter, melon seed oil has many compounds linked with antiinflammatory properties. However, research concerning the study of melon seed oil on antiinflammatory activity is lacking. Bouazzaoui et al., 2018 evaluated the antiinflammatory activity of melon seed oil on soybean lipoxygenase. The authors evaluated the antiinflammatory activity of four melon seed oil extracts obtained with different solvents (50 mg/mL). The highest result of the inhibition of inflammation was 18.8% for the extract of n-hexane and the extract of Supercritical CO2, at 55 MPa and 70oC. The control was nordihydroguaiaretic acid % (0.26 mg/mL), with a percentage of inhibition of 52%. The percentages of inflammation inhibition for the remaining extracts varied between 4.1% and 11.4%. Although the results obtained are not very promising regarding the antiinflammatory activity of melon seed oil, the presence of compounds with antioxidant activity may play an important role during inflammation (Rubio´ et al., 2013).

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11.4.3 Antimicrobial activity The edible oils use in the industry is strongly linked to its oxidative stability and antibacterial activity (Aluyor & Ori-Jesu, 2008). Several bacteria and fungi are common in the environment, mainly Staphylococcus aureus and Escherichia coli, which are source of human pathogenic conditions. These pathogenic microorganisms can cause serious infections, sometimes fatal, being their control extremely important (Xuan et al., 2018). It should also be noted that, for some microorganisms, there has been an increase in their resistance to antibiotics (Silva et al., 2011). Ahamed et al., 2014 tested antibacterial activity against E. coli, Salmonella typhi, Staphylococcus aureus and Bacillus cereus and antifungal activity against Aspergillus funiculosus, Fusarium equiseti, Curvularia lunata, and Alternaria alternata of essential oil of C. melo L. seeds. According to the results melon seed oil had the highest antibacterial inhibition against Salmonella typhi, greater effectiveness against Gram-positive bacteria and the highest antifungal inhibition against Aspergillus funiculosus. Another study evaluated the antibacterial activity of melon seed oil against Grampositive (Streptococcus pyogenes, S. aureus, Bacillus subtilis) and Gram-negative bacteria (Salmonella typhimurium, Shigella dysen-teriae, and E. coli). In this study, the oil of melon seeds was more effective against Gram-positive bacteria and presented the highest antibacterial inhibition against S. aureus (Siddeeg et al., 2014).

11.4.4 Antihypercholesterolemic activity Hypercholesterolemia is a serious health concern worldwide. High cholesterol has been associated with the development of cardiovascular diseases, atherosclerosis and stroke (Djousse´ & Gaziano, 2009). Melon seed oil has a high content of polyunsaturated fatty acids which, as already mentioned, has the ability to reduce total cholesterol and lowdensity lipoprotein cholesterol. However, and as far as the authors know, there are few studies regarding the antihypercholesterolemic activity of melon seed oil. Hao et al. (2020) studied the effect of melon seed oil on blood cholesterol and gut microbiota. For this, the authors fed hamsters with high-cholesterol diets supplemented with melon seed oil (4.75% and 9.5%). Through this supplementation, they found that it reduced plasma cholesterol by 24% and that this effect was mediated by the increased excretion of fecal acid sterols. In addition, they also found that supplementation with melon seed oil may have a positive effect on the modulation of the intestinal microbiota, increasing the growth of short-chain fatty acids-producing bacteria and inhibiting the growth of bacteria with negative effects on blood lipids.

11.5 Conclusion Nowadays there is a great demand for new sources of vegetable oils because some of the existent oilseeds are very vulnerable to climatic conditions, but also due to increased soil degradation, making difficult crop growth. Up to now, melon seeds are discarded, which could represent not only an environmental concern due to its impact, but also an

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economic loss for food industry. The high quantity of wasted melon seeds and their high oil content are two factors pointing out to the valorization of the referred seeds. They can provide a high-quality vegetable oil, answering to the lack of raw material, and improve the incomes, becoming an excellent opportunity for the food industry. Melon seed oil is a good source of natural antioxidants, tocopherols, tocotrienols and sterols, compounds with interesting biological activities, beneficial health effects and reducing risk of some diseases. Besides, it also has an interesting fatty acid profile, very similar to some vegetable oils already in the market. The choice of the most appropriate extraction method is one of the greatest challenges, and one of the most important topics to produce high-quality oils. In this selection, it is necessary to consider not only production costs, but also the more sustainable, and which allow high quality oil production. Although there are still few studies regarding the biological activities of melon seed oil, this is a great source of bioactive compounds with excellent beneficial properties to health, as demonstrated along this chapter. However, further analysis should be carried out to evaluate the effectiveness of its properties, to prove its high potential and to demonstrate the advantages of using melon seed oil for health and for the food industry. In addition, the use of seeds for oil production will contribute to the reduction of food waste, reducing the environmental concerns that arise from its disposal, and allowing a more sustainable production for various industries (e.g., food, pharmaceutical, cosmetics). In summary, it is expected that this chapter will stimulate further research on new biological activities of melon seed oil and will be a starting point for its use as a potential nutritional edible oil.

Acknowledgments This work was funded by INSA, I.P., under the project MELON4FOOD (2018DAN1492);by PT national funds (FCT/MCTES, Fundac¸a˜o para a Cieˆncia e Tecnologia and Ministe´rio da Cieˆncia, Tecnologia e Ensino Superior) through the project UIDB/50006/2020; and by AgriFood XXI I&D&I project (NORTE-01
0145-FEDER-000041) cofinanced by European Regional Development Fund (ERDF), through the NORTE 2020 (Programa Operacional Regional do Norte 2014/2020). Rita C. Alves thanks to FCT the CEECIND/01120/2017 contract.

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C H A P T E R

12 Antioxidant, antimicrobial, and antidiabetic activities of Citrullus colocynthis seed oil Abdalbasit Adam Mariod1,2 and Robert L. Jarret3 1

College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 3USDA/ARS, Plant Genetic Resources Unit, Griffin, Georgia, United States 2

12.1 Introduction Citrullus colocynthis (L.) Schrad. is an herbacious perennial vine that is a member of the Cucurbitaceae family and distantly related to the common watermelon [C. lanatus (Thunb.) Matsum. & Nakai]. It is also referred to as colocynth, bitter apple, bitter cucumber, bitter gourd, desert gourd, vine of Sodom, tumba, handal, egusi, and others. Care should be taken to not confuse C. colocynthis with the egusi melon of West Africa [C. mucosospermus (Fursa) Fursa]. Citrullus colocynthis will hereafter be referred to as colocynth. The slender vines of colocynth spread across the ground and are anchored by tendrils. Like most members of this genus, colocynth is monoecious with distinct male and female flowers occurring on the same plant. The flowers are yellow with five petals. The fruit are spherical, green with irregular longitudinal stripes, about the size of an apple, and in general having very bitter flesh (Fig. 12.1). The fruit flesh is typically very firm becoming somewhat softer at maturity, and is whitish in color (Omme & Asia, 2020). At full maturity, the fruit take on a yellowish cast (Nwokolo, 1996). See Jeffrey (1967) for a complete description.

12.2 Colocynth seed chemistry Colocynth seeds are numerous, compact, smooth, shiny and brown or brown/black in color (Fig. 12.2). The seeds contain a fatty oil that is yellow in color and similar to

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00005-2

139

© 2022 Elsevier Inc. All rights reserved.

140

FIGURE 12.1

12. Antioxidant, antimicrobial, and antidiabetic activities of Citrullus colocynthis seed oil

Citrullus colocynthis (colocynth) plant and fruits. Source: https://commons.wikimedia.org.

FIGURE 12.2 Citrullus colocynthis (colocynth) pulp and seeds.

safflower and soybean oil in its composition (Ramakrishna et al., 1993; Yaniv et al., 1996). Thermogravimetric analysis showed that the oil is thermally stable up to 286.57 C (Nehdi et al., 2013). According to Ramakrishna et al. (1993) and Nehdi et al. (2013), the seed oil of colocynth is edible and refining and washing it with citric acid removes its bitter taste (Ramakrishna et al., 1993). Oil yields of 250
400 L/ha have been suggested for this nonconventional crop (Yaniv et al., 1999).

Multiple Biological Activities of Unconventional Seed Oils

12.3 Biological activity of colocynth extracts

141

The study of Nehdi et al. (2013) reported that the percentage of oil in colocynth seeds reached 7% of the weight of the seeds, while protein, carbohydrates and dietary fiber accounted for 11.7%, 29.5%, and 5.51%, respectively. The oil is rich in fatty acids. The percentage of fatty acids typically ranges from 17% to 23%. The fatty acid composition reported by Nehdi et al. (2013) was linoleic acid (66%
76.4%), palmitic acid (6.3%
8.1%), oleic acid (7.8%
14.2%), and stearic acid (6.1%
7.3%), while the total tocopherols were 121.85 mg/100 g. γ-tocopherol was the predominant form. The total yield of unsaturated fatty acids has been estimated to vary from 209 to 327 L/ha (Palevitch & Yaniv, 1991). The seeds of colocynth contain high concentrations of potassium (324
535 mg/100 g), phosphorus (115.3
189.22 mg/100 g), and iron (3.81
7.67 mg/100 g) (Anonymous, 2008). The protein of colonynth seeds is rich in isoleusine, leusine and tryptophan (3.96
4.19), (6.78
7.26) and (1.21
1.31) g/100 g protein, respectively (Anonymous, 2008). Elltayeib et al. (2020) reported the presence of flavonoids, saponins, alkaloids, and phenolic compounds in seed oil of colocynth.

12.3 Biological activity of colocynth extracts The literature contains hundreds of references to the medicinal and other useful properties associated with extracts of whole plants, leaves, roots, fruit flesh, fruit rind, and whole fruit of colocynth. Readers are directed to the reviews of Abdulridha et al. (2020), Al-Snafi (2016), Dhakad et al. (2017), Gurudeeban et al. (2010), Hussain et al. (2014), Kapoor et al. (2020), Mazher et al. (2020), Meybodi (2020), Rahimi et al. (2011), Shi et al. (2014), Yaniv et al. (1999), Zheng et al. (2020), among others. Likewise, numerous medicinal and other biological properties have been found to be associated with extracts of colocynth seeds (see previous reviews). However, the literature contains relatively few reports on the biological activities associated with colocynth seed oil . This may be due to the lack of available seed for oil extraction or perhaps is due to the technical difficulties associated with oil extraction. This report will, unless noted otherwise, attempt to focus on the biological activities associated with colocynth seed oil (Table 12.1).

12.3.1 Antioxidant activity of colocynth seed oil Various plant parts, fruits and seed of colocynth contain large amounts of phenolics and flavonoids that have antioxidant activity (Kumar et al., 2008). Numerous publications have documented the antioxidant activity associated with colocynth plant tissues (Huseini et al., 2009; Kumar et al., 2008). Antioxidant properties associated with colocynth seed extracts are also well documented (e.g., see Benariba et al., 2013; Bourhia et al., 2020; Gacem et al., 2019; Gill et al., 2011; Tawfik et al., 2015). Cadmium (Cd) is a common heavy metal pollutant that tends to accumulate in the liver and kidneys. Amamou et al. (2015) examined the ability of two oils, olive oil and colocynth oil, to protect against Cd-induced damage of plasma lipids and the biochemical parameters associated with stress, on rats. Rats were fed Cd, olive oil or colocynth oil, alone or in various combinations. When the rats were later analyzed, it was determined that Cd

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TABLE 12.1 Published reports of activity associated with colocynth seed oil. Activity

Organism or action

References

Antibacterial

Xanthomonas campestris, Pseudomonas syringae, Streptococcus pyogenes, Pseudomonas aeruginosa, Candida albicans, Grampositive and Gram-negative bacteria.

Elltayeib et al. (2020); Mehr et al. (2012); Hussein et al. (2020)

Antidiabetic

Restored insulin sensitivity and improved lipid profile. Prevented high-fat diet induced increases in body weight and visceral fat mass.

Sari (2019); Yazit et al. (2019)

Antioxidant

Prompted a corrective effect in the antioxidant defense systems.. Antioxidant activity of the extracted oil determined to be 39 6 0.8. Protected liver against Cd-induced injury in rats.

Amamou et al. (2015); Hussein et al. (2020); Sari, (2019)

Insecticidal

Cowpea weevil (Callosobruchus maculatus)

Nzelu and Okonkwo (2016)a

Miscellaneous In ancient times, used as lamp oil. a

Palevitch and Yaniv (1991)

Possibly Citrullus mucosospermus.

exposure increased the activityies of various enzymes, lipid peroxidation levels and protein carbonyl contents. In contrast, Cd treatment decreased antioxidant enzymes, reduced glutathione and vitamins C, A, and E. Co-treatment with olive oil or colocynth oil significantly reduced the oxidative damage induced by Cd. The antioxidant potential in plasma and liver were largely restored with a significant decline in lipid peroxidase levels, and the activity of transaminases. The authors concluded that either olive oil or colocynth oil consumption protected the rat liver against Cd-induced injury (Amamou et al., 2015). Sari et al. (2018) examined the role of colocynth seed oil as a natural remedy to obesity. In that study, rats were subjected to diets that were very low to very high in fat content. The results indicated a significant correlation between fat (provided as olive oil or colocynth seed oil) intake and body weight, blood parameters, total cholesterol, triglycerides, HDL-C [high-density lipoprotein (HDL) cholesterol], and glycemia. Colocynth seed oil-treated rats showed an improved redox status with an increase in antioxidant vitamin levels, a decrease in malondialdehyde contents, and an increase in hepatic enzyme activities, when compared to olive oil-treated rats. The results suggested that colocynth seed oil can prompt a corrective effect in the antioxidant defense system, restore insulin sensitivity, and improve the lipid profile. Hussein et al. (2020) analyzed the antioxidant activity in extracted colocynth seed oil using the standard 2,2-diphenyl-1-picrylhydrazyl (DPPH) 0.5 mL. The antioxidant activity of the extracted oil was determined to be 39 6 0.8.

12.3.2 Antimicrobial activity of colocynth seed oil Various chemical components are known to be present in colocynth seed extracts. These include alkaloids, flavonoids, and glycosides that have a powerful antibacterial effect (Najafi et al., 2010). Not surprisingly, dozens of published studies have documented the antibacterial and antifungal activity associated with extracts from various plant parts of

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colocynth. Readers are referred to the review articles cited earlier. Specific examples of studies utilizing extracts from whole seeds include Amine et al. (2013a,b), Almalki (2017), and Gacem et al. (2019). Mehr et al. (2012) demonstrated the antibacterial activity of the essential oil derived from dryground seed of colocynth. The oil was tested against several bacteria including Xanthomonas campestris, Burkholderia cenocepacia, Pseudomonas syringae, and Agrobacterium tumefaciens using an agar disk diffusion method. Antibacterial activity was confirmed for all bacterial strains with X. campestris being the most sensitive and P. syringae being the least sensitive. These authors suggested that the use of the oil may provide a means to prevent or delay the decay of fruits and vegetables, and possibly have an application in disease prevention. In a more recent study, Elltayeib et al. (2020) investigated the antibacterial characteristics of colocynth seed oil on Streptococcus pyogenes (Gram-positive bacterium that causes strep throat) and Pseudomonas aeruginosa (Gram-negative bacterium that causes a variety of systemic infections in humans) using a diffusion assay. The antibacterial effect was dose dependent. At 100 mg/ml the oil was most effective against Pseudomonas aeruginosa and moderately effective against Streptococcus pyogenes. Hussein et al. (2020) examined seed oil of colocynth for its potential antimicrobial activity. The seeds were collected locally in Sudan. The antimicrobial activity of the extracted seed oil was evaluated using a diffusion assay against Gram-positive bacteria (Staphylococcus aurous and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and the fungus Candida albicans. The seed oil extract showed high levels of activity against the fungus Candida albicans at a concentration of 100 mg/mL and little activity at a concentration of 75 mg/mL. No distinct zone of inhibition was evident at lower concentrations. A concentration of 100 mg/mL was active against all four bacteria. The authors recommended further testing of the seed oil for additional antimicrobial activity.

12.3.3 Antidiabetic activity of colocynth seed oil Diabetes is one of the most common causes of death worldwide. The rate of infection of the world’s population has reached 7%, and this percentage is expected to increase. Many antihyperglycemic drugs and insulin stimulants are available, but the adverse side effects sometimes associated with these drugs have prompted an interest in the use of alternative natural products. Natural products are expected to have fewer side effects and to be less expensive making them more readily available. Colocynth is a plant traditionally used for its antidiabetic properties in Mediterranean countries (Oryan et al., 2014). As noted earlier, Sari et al. (2018) reported that seed oil of colocynth restored insulin sensitivity and improved lipid profiles. Seed extracts of colocynth have been evaluated and shown to have antidiabetic activity (e.g., see Dashti et al., 2012; Jemai et al., 2020; Khoshvaghti & Hamidi, 2011). Shi et al. (2014) provide a general review the antidiabetic properties of colocynth tissue extracts. Obesity is also a major public health concern and is often associated with diabetes. Yazit et al. (2019) examined the potential protective effects of colocynth seed oil and fatty acid methyl esters (FAMEs) consumption to reduce obesity in rats. The rats received sunflower oil, colocynth oil, and FAMEs alone or in combination. A 28% sunflower oil was used as a

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high-fat diet control. After treatment, the colocynth oil and FAMEs-treated rats showed decreased levels of plasma total cholesterol, low-density lipoproteins and triglycerides, HDL and body weight. Consumption of colocynth oil significantly prevented high-fat diet-induced increases in body weight and visceral fat mass.

12.4 Conclusion Although hundreds of studies have investigated the medicinal, antibacterial, antifungal, insecticidal, and other biological properties associated with extracts of various plant parts and fruit (with and without seeds) of colocynth, few studies have evaluated its seed oil for a similar range of activities. The few reports in the scientific literature indicate that colocynth seed oil does possess significant and useful biological activities. This suggests that further evaluations of its properties are likely to identify new uses for the oil of this ancient crop.

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204. Al-Snafi, A. E. (2016). Chemical constituents and pharmacological effects of Citrullus colocynthis. A review. IOSR Journal of Pharmacy, 6, 5
67. Amamou, F., Nemmiche, S., Meziane, R. K., Didi, A., Yazit, S. M., & Chabane-Sari, D. (2015). Protective effect of olive oil and colocynth oil against cadmium-induced oxidative stress in the liver of Wistar rats. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 78, 177
184. Amine, G. M., El Hadj-khelil Aminata, O., Sawsen, H., Amel, B., & Nesrine, D. A. (2013b). Phytochemical screening and antibacterial activity of aqueous extracts of Citrullus colocynthis seeds. PhytoChem BioSub. Journal, 7, 90
94. Amine, G. M., El HadjJ, O., Aminata, K., Bouabdallah, G., Noureddine, H., Nesrine, D. A., Amel, B., Sawsen, H., Mokhtar, B., & Houari, A. D. E. (2013a). Antimycotoxigenic and antifungal activities of Citrullus colocynthis seeds against Aspergillus flavus and Aspergillus ochraceus contaminating wheat stored. African Journal of Biotechnology, 12(43), 6222
6231. Anonymous. (2008). Gross composition, mineral content and nutritional value of colocynth fruit seed. Alexandria Journal of Food Science Technology, 5, 41
47. Benariba, N., Djaziri, R., Bellakhdar, W., Belkacem, N., Kadiata, M., Malaisse, W. J., & Sener, A. (2013). Phytochemical screening and free radical scavenging activity of Citrullus colocynthis seeds extracts. Asian Pacific Journal of. Tropical Biomedicine, 3, 35
40. Available from https://doi.org/10.1016/S2221-1691(13)60020-9. Bourhia, M., Messaoudi, M., Bakrim, H., Mothana, R. A., Sddiqui, N. A., Almarfadi, O. M., Mzibri, M., El Gmouh, S., Laglaoui, A., & Benbacer, L. (2020). Citrullus colocynthis (L.) Schrad: Chemical characterization, scavenging and cytotoxic activities. Open Chemistry, 18, 986
994. Dashti, N., Zamani, M., Mahdavi, R., & Ostad Rahimi, A. (2012). The effect of Citrullus colocynthis on blood glucose profile level in diabetic rabbits. Journal of Jahrom University of Medical Sciences, 9, 24
28. Dhakad, P. K., Sharma, P. K., & Kumar, S. (2017). A review on phytochemical studies and biological potential of Citrullus colocynthis (L.) Schrad. (Cucurbitaceae). Bioengineering and Bioscience, 5(4), 55
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1189. Hussain, A. I., Rathore, H. A., Sattar, M. Z. A., Chatha, S. A. S., Sarker, S. D., & Gilani, A. H. (2014). Citrullus colocynthis (L.) Schrad. (bitter apple fruit): A review of its phytochemistry, pharmacology, traditional uses and nutritional potential. Journal of Ethnopharmacology, 155, 54
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8. Jeffrey, C. (1967). Flora of tropical East Africa. Cucurbitaceae. Royal Botanic Gardens, Kew. UK. Jemai, R., Drira, R., Makni, M., Fetoui, H., & Sakamoto, K. (2020). Colocynth (Citrullus colocynthis) seed extracts attenuate adipogenesis by down-regulating PPARγ/ SREBP-1c and C/EBPα in 3T3-L1 cells. Food Bioscience, 33100491. Kapoor, M., Kaur, N., Sharma, C., Kaur, G., Kaur, R., Batra, K., & Rani, J. (2020). Citrullus colocynthis an important plant in Indian traditional system of medicine. Pharmacognosy Reviews, 14(27), 22
27. Khoshvaghti, A., & Hamidi, A. R. (2011). Comparative effects of oral administration of Citrullus colocynthis and insulin injection on serum biochemical parameters of alloxan-induced diabetic dogs. Comparative Clinical Pathology, 21, 1337
1341. Available from https://doi.org/10.1007/s00580-011-1293-5. Kumar, S., Kumar, D., Jusha, M., Saroh, K., Singh, N., & Vashishta, B. (2008). Antioxidant and free radical scavenging potential of Citrullus colocynthis (L.) Schrad. methanolic fruit extract. Acta Pharmaceutica (Zagreb, Croatia), 58, 215
220. Mazher, M., Ishtiaq, M., Mushtaq, W., Maqbool, M., Zahid, N., Husain, T., & Mazher, M. (2020). Comprehensive review of phytochemistry and bioactivities of Citrullus Colocynthis (L.) Schrad. Pharmaceutical Research, 4(4)000218. Mehr, Z. S., Sanadgol, N., & Ghasemi, L. V. (2012). Effects of essential oil extracted from Citrullus colocynthis (CCT) seeds on growth of phytopathogenic bacteria. Afric. Journal of. Microbiology Research, 6, 6572
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34. Najafi, S., Sanadgol, N., Nejad, B. S., Beiragi, M. A., & Sanadgo, E. (2010). Phytochemical screening and antimicrobial activity of Citrullus colocynthesis (Linn.) Schrad against Staphylococcus aureus. Journal of Medicinal Plants Research, 4, 2321
2325. Nehdi, I. A., Sbihi, H., Tan, C. P., & Al-Resayes, S. I. (2013). Evaluation and characterization of Citrullus colocynthis (L.) Schrad. seed oil: Comparison with Helianthus annuus (sunflower) seed oil. Food Chemistry, 136, 348
353. Nwokolo, E. (1996). Melon (Colocynthis citrullus L.). In E. Nwokolo, & J. Smartt (Eds.), Food and feed from legumes and oilseeds. Boston, MA: Springer. Available from https://doi.org/10.1007/978-1-4613-0433-3_29. Nzelu, C. O., & Okonkwo, N. J. (2016). Evaluation of melon seed oil Citrullus colocynthis (L.) Schrad, for the protection of cowpea Vigna Unguiculataseeds against Callosobruchus maculatus (Fabricius) (Coleoptera: Bruchidae). International Advannced Research Journa of Science and Engineering Technology. (3, pp. 76
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21158. Oryan, A., Hashemnia, M., Hamidi, A. R., & Mohammadalipour, A. (2014). Effects of hydro-ethanol extract of Citrullus colocynthis on blood glucose levels and pathology of organs in alloxan-induced diabetic rats. Asian Pacific Journal of Tropical. Disease, 4, 125
130. Palevitch, D., & Yaniv, Z. (1991). Medicinal plants of the Holyland (in Hebrew) (pp. 56
58). Tel Aviv: Tamus Modan Press. Rahimi, R., Amin, G., & Ardekani, M. R. S. (2011). A review on Citrullus colocynthis Schrad.: From traditional Iranian medicine to modern phytotherapy. Journal of Alternative and Complementary Medicine (New York, N.Y.), 18, 551
554. Available from https://doi.org/10.1089/acm.2011.0297.

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5. Sari, M.C., Nemmiche, S., Benmehdi, H., Amrouche, A., Hamadi, A.L., Sari, D.C. (2018). Hypolipidemic and antioxidant effects of Citrullus colocynthis seeds oil in high-fat diets induced obese rats. Phytotherapie 17(6). Available from https://doi.org/10.3166/phyto-2018-0066. Shi, C., Karim, S., Wang, C., Zhao, M., & Murtaza, G. (2014). A review on antidiabetic activity of Citrullus colocynthis Schrad. Acta Poloniae Pharmaceutica, 71(3), 363
368. Tawfik, K., Barazi, M. A., Bashir, M., Marzouq, W. A., Al-Soufi, R., & Kharsa, H. (2015). A comparative study of antioxidant activities of ziziphus and colocynth from Saudi Arabia deserts and proposed pharmaceutical products. International Research Journal of Pharmaceutical Applied Science, 5, 1
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261). Alexandria, VA: ASHS Press. Yazit, S. M., Nemmiche, S., Amamou, F., Meziane, R. K., & Chabane-Sari, D. (2019). Anti-hyperlipidemic effect of fatty acids methyl esters (FAMEs) of Citrullus colocynthis in high-fat diet induced obesity in rats. Phytothe´rapie. Available from https://doi.org/10.3166/phyto-2018-0101. Zheng, M. S., Liu, Y. S., Yuan, T., Liu, L. Y., Li, Z. Y., & Huang, X. L. (2020). Research progress on chemical constituents of Citrullus colocynthis and their pharmacological effects. Zhongguo Zhong Yao Za Zhi 5 Zhongguo Zhongyao Zazhi 5 China Journal of Chinese Materia Medica, 45, 816
824. Available from https://doi.org/ 10.19540/j.cnki.cjcmm.20191104.201, Chinese.

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C H A P T E R

13 Antioxidant and pharmacological activity of Cucumis melo var. cantaloupe Neuza Jorge1, Ana Carolina da Silva2 and Carolina M. Veronezi1 1

Department of Food Engineering and Technology, Sa˜o Paulo State University, Sa˜o Jose´ do Rio Preto, Brazil 2Department of Food Engineering, Federal University of Triaˆngulo Mineiro, Uberaba, Brazil

Abbreviations AAE CE DMSOE DPPH• QE Fe12-TPTZ Fe13-TPTZ FRAP GAE HPLC-PDA IC50 LDLc LLL OLL OOL PLL POL RE SOD αTE UI

ascorbic acid equivalent catechin equivalent dimethy sulphoxide (DMSO) equivalent radical 2,2-difenil-1picrylhydrazyl quercetin equivalent ferrous iron tripyridyltriazine tripyridyltriazine ferric iron antioxidant power by reducing ferric ion galic acid equivalent high performance liquid chromatography-photodiode array detection inhibitory concentration low density lipoprotein fraction linoleic
linoleic
linoleic oleic
linoleic
linoleic oleic
oleic
linoleic palmitic
linoleic
linoleic palmitic
oleic
linoleic rutin equivalent supero´xido dismutase enzyme α-tocopherol equivalent international unity

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13.1 Introduction The family Cucurbitaceae is quite numerous and heterogeneous, being composed of several genera and species used for human consumption or as ornamental plants. Among the species of greatest agronomic significance, pumpkin (Cucurbita pepo L.), cucumber (Cucumis sativus L.), maxixe (Cucumis anguria L.), watermelon (Citrullus lanatus), and melon (Cucumis melo L.) stand out (Priori et al., 2010). According to Criso´stomo et al. (2002), there are several varieties of C. melo L., such as cantalupensis, reticulatus, inodorus, conomon, dudaim, flexuosus, and momordica. Within each species, in order to facilitate trading, the melons are divided into types, according to certain characteristics, such as peel appearance (netting and color), pulp (color, sweetness, smell), fruit shape, among others. With this categorization, six types of melon are presented: Canary, Santa Claus, Galia, Charentais, Orange Fresh, and Cantaloupe. Cantaloupe is the most produced melon type in the world. Its fruits are characterized by their round shape, peel with different degrees of netting, the pulp of pleasant taste, nutritional value (source of vitamin A), and uniformity (Figueireˆdo et al., 2017; Fundo, Miller, Garcia, et al., 2018). With consumption in natural and industrial processing of melon (juice, jam, and salads), great quantities of waste are generated. Studies show that melon peels and seeds are possible sources of phytochemicals, such as polyphenols, carotenoids, fatty acids, among others, which are responsible for several biological activities (antimicrobial, provitamin A, antioxidant, etc.) (Vella et al., 2019). In addition, the reintegration of melon by-products with the food chain as additives, supplements, or ingredients that are rich in nutrients and bioactive compounds, for the production of functional foods, is important, in order to reduce environmental and economic problems related to the accumulation of bad management of these byproducts (Go´mez-Garcı´a et al., 2021; Silva et al., 2020).

13.2 Botanical description, distribution, and cultivation regions of melon The botanical family Cucurbitaceae Juss. belongs to the class Eudicotyledoneae and to the order Curcubitales, according to the molecular phylogenetic classification (Zhang et al., 2006). This family holds a great number of species, especially in the tropical and subtropical regions of the world, the temperature being a limiting factor for its geographic distribution and crop area. The family comprises 118 genera with approximately 950 species, being one of the largest and most diverse existing families. In American tropical region, 53 native genera and nearly 325 species are described (Schaefer & Renner, 2011). Several cultivated species that belong to the family Cucurbitaceae present high economic value, especially for the use of their fruits and edible seeds. Certain fruits are used by the pharmaceutical industry as medicinal phytochemicals, due to the presence of bioactive compounds, while others are dried and used as compounds in musical instruments, sponges, etc. (Pereira et al., 2010). The genus Cucumis, which belongs to the subfamily Cucurbitoideae, holds 32 species and is considered one of the genera of greatest agronomic and economic importance (Yoshikazu et al., 2013). The main species are C. sativus L., C. metuliferus, C. anguria, C. myriocarpus, C. dipsaceus, and C. melo (Vishwakarma et al., 2017).

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C. melo L. is a polymorphic species, and its genetic center of origin has not been elucidated yet. However, it is believed that the species has been introduced in Europe and Asia during the last 2000 years. Its several varieties and types are cultivated mainly in India and in tropical countries (Mansouri et al., 2017). The wide distribution of melon around the world proves that this is the species of highest phenotypic variability of the genus Cucumis, which can be verified on the fruits with different colors, shapes, and smells (Stepansky et al., 1999). Melon is a very polymorphic diploid species and it presents two subspecies according to ovary hairiness: C. melo subgen. Agrestis, with waxy ovary, and C. melo subgen. Melo, with hairy ovary. Each subspecies presents different botanical varieties, which are: cantalupensis, reticulatus, inodorus, conomon, dudaim, flexuosus, and momordica (Pitrat et al., 1999). In general, the melon plant presents superficial root system and almost no adventitious roots, as well as herbaceous decumbent stem, alternate, simple, rough leaves of variable sizes, and male flowers that grow in clusters, while female flowers grow isolated. The fruits from the several botanical groups of melon change regarding taste, size, weight, color, peel texture, smell, and pulp. Each fruit produces between 200 and 600 seeds, symmetrically arranged inside the pulp (Figueireˆdo et al., 2017). Small and big companies have been interested in the cultivation of melon, for its high added value. Therefore, crop areas are expanding every year. This vegetable is used in the production of biodiesel in some parts of the world, which makes it a valuable crop of economic importance (Giwa & Akanbi, 2020). C.s melo var. cantalupensis and C. melo var. reticulatus are the most popular varieties of cantaloupe and were probably originated somewhere between Iran and India and/or in Africa. The name “cantaloupe” supposedly derives from the Italian “Cantalupo in Sabina,” which used to be one of the headquarters of the papal county near Rome (Maietti et al., 2012). European cantaloupes belong to the variety cantalupensis. Their fruits are oval or round, with greyish-green peel, and normally orange, sweet, tasty pulp (Silva et al., 2020). On the other hand, North American cantaloupes, which are common in the United States, Mexico, and some parts of Canada, belong to the variety reticulatus. They require more careful postharvest handling, are round, with netted peel, and firm, orange, mildly sweet pulp (Araga˜o, 2010; Mariod et al., 2017). Cantaloupe is a popular type of melon, consumed all over the world for its sweet taste, nutritional value, and uniformity (Fundo, Miller, Garcia, et al., 2018). In addition, it is considered a noble fruit, due to its high level of soluble solids and carotenoids (Cuevas et al., 2010). Cantaloupe is a good source of vitamins A and E, magnesium, and potassium. The fruit also presents several biological and pharmacological properties, such as anticancer, antioxidant, and antidiabetic activities. Cantaloupes have been used in medicine to cure liver disease, cough, eczema, kidney diseases, as well as to treat toothaches and as diuretics (Preeti & Raju, 2017). They are sources of polyphenols, including flavonoids and tannins, which are responsible for antioxidant, antimutagenic, and anticarcinogenic activities (Rolnik & Olas, 2020). The melon is usually consumed in natural or processed as jam, juice, nectar, and cocktails or other alcoholic beverages. One of the negative impacts of the processing industries around the world is associated with the significant amount of organic waste they produce. Generally, the nonedible parts of melon (peel and seeds) amount to between 8 and 20 million

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tons every year, all over the world. Since processing yield is between 38% and 42% of pulp, 58%
62% of raw material is disposed of (Rolim et al., 2020). These residues are either discarded, which causes damage to the environment, or underused as animal feed, organic material for the prevention of soil erosion, or biofuel precursors (Veronezi & Jorge, 2018). However, research has shown that these by-products are rich in polyphenols, carotenoids, vitamins, minerals, fibers, oils, and other biologically active compounds which positively affect human health and well-being (Silva et al., 2020; Torres-Leo´n et al., 2018; Vella et al., 2019). Thus, the residues may be added to food, providing consumers with healthier and more natural products, since these residues are able to change or enhance their taste, texture, smell, color, and nutritional value (Marchetto et al., 2008).

13.2.1 Pulp 13.2.1.1 Nutritional composition Cantaloupe pulp is composed of water (90.15%), carbohydrates (8.16%), proteins (0.84%), ashes (0.65%), and lipids (0.19%). Its caloric value is 34 kcal/100 g and, among total sugars (7.86%), sucrose (4.35%), glucose (1.54%), and fructose (1.87%) stand out (Amaro et al., 2015). Potassium was found in cantaloupe pulp in the amount of 2.87 mg/g (Fundo, Miller, Garcia, et al., 2018), while selenium was detected in a much lower quantity, 0.4 μg/100 g (Amaro et al., 2015). According to Fundo, Miller, Garcia, et al. (2018), cantaloupe pulp presents 10.35 Brix. This scale represents the balance between sugars and acids, affecting, mainly, fruit taste. Pulp color was determined by the authors through the parameters of lightness (L*), chroma (C*), and hue angle (H ), and the values found were 51.16, 31.88, and 70.66, respectively. This means that the pulp color stands between red and yellow, which suggests the color orange, probably due to the presence of carotenoids. The quality of cantaloupe is not defined by one single attribute. Yamaguchi et al. (1977) concluded that the most important factor for its sensory acceptability is sweetness, followed by smell or color of the pulp, depending on the crop. The third most important element for quality is texture. Consumer sensory preference was analyzed between cantaloupe and honeydew by a trained sensory panel. The results show that cantaloupe was preferred for its taste. For the tasters, the most relevant attributes were its fruity taste, sweetness, and juiciness (Park et al., 2018). Kourkoutas et al. (2006) determined that cantaloupe contains high levels of acetate esters, as well as esters derived from n-butanol and isobutanol. In addition, cantaloupes presented esters containing sulfur, which might contribute to a higher perception of floral, fruity, and sweet smells during the sensory analysis of these fruits. 13.2.1.2 Bioactive composition Rodrı´guez-Pe´rez et al. (2013) identified different bioactive compounds, including amino acids and their derivatives, organic acids, phenolic acids and their derivatives, esters, flavonoids, lignans, and other polar compounds in the pulp from three melon varieties. The carotenoids contained in the melon are important bioactive compounds, as they present health benefits. They are also regarded as powerful antioxidants, can be converted into vitamin A, besides preventing the emergence of cardiovascular diseases, cancer, and cataract (Saini et al.,

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2015). In C. melo L., it is possible to find α-carotene, β-carotene, lutein, β-cryptoxanthin, phytoene, violaxanthin, neoxanthin, and zeaxanthin (Yano et al., 2005). Studies show that cantaloupes are an excellent source of β-carotene, as their pulp contains 176.3 μg/g of the pulp. They are also a source of vitamin A, such as the carrot (Fleshman et al., 2011). The level of β-carotene in cantaloupe pulp was also reported in other studies. Amaro et al. (2015) described 2020 μg/100 g of β-carotene, besides other carotenoids, such as α-carotene, β-cryptoxanthin, and lutein, in lower quantities. Laur and Tian (2011) quantified the level of β-carotene in cantaloupe from California. On average, they presented 3270 μg/100 g of the carotenoid, which is higher than the average found in honeydew cultivated under the same conditions. Fundo, Miller, Garcia, et al. (2018), while comparing the level of β-carotene from different parts of melon (pulp, peel, and seeds) showed that the pulp has the highest level of carotenoids, 68.92 mg of β-carotene, which is 38% higher than the juice obtained from the pulp. These studies show the nutritional value of this fruit. In order to improve color stability and solubility in water, the carotenoids in cantaloupe pulp were isolated in gelatin microcapsules using the system of oil-in-water emulsion. The encapsulated extract was added to yogurt in order to simulate the color of yellow fruits. The study proved that the color of yogurt with added microcapsules presented higher stability when compared to the product added with crude extract (Medeiros et al., 2019). Moreira et al. (2014) reported concentration of 70 mg/100 g of vitamin C in minimally processed melon. The study of this element is extremely important, since it is considered an indicator of food quality due to its antioxidant properties. The authors Laur and Tian (2011), Amaro et al. (2015), and Fundo, Miller, Garcia, et al. (2018) found levels of vitamin C in cantaloupe pulp of 40.85, 36.70, and 88.08 mg/100 g, respectively. Moreover, other vitamins were found in the pulp, such as vitamin A (169 mg/100 g), vitamin K (2.5 mg/ 100 g), niacin (0.734 mg/100 g), pantothenic acid (0.105 mg/100 g), vitamin E (0.05 mg/ 100 g), thiamine (0.041 mg/100 g), and riboflavin (0.019 mg/100 g) (Amaro et al., 2015). Melon in natural is a very perishable food. For this reason, its storage must be monitored, in order to avoid losses. Amaro et al. (2018) studied the influence of storage temperature in the quality of cantaloupe. According to the authors, 0 C is the ideal temperature to reduce the microbial load and preserve vitamin C. However, at 10 C, the phenolic compounds and the volatile organic compounds, responsible for the smell, are better preserved. Phenolic compounds are also important bioactive substances, since they present reducing activity through donation of hydrogen. They are secondary metabolites in vegetables and are distributed irregularly in different parts of the plant. The technological property of melon is present, especially, in its use for the preparation of juice. Several studies aim to analyze the stability of products regarding the effects of storage such as light, ozone, ultrasound, among others (Amaro et al., 2018; Fonteles et al., 2012; Fundo et al., 2019; Solval et al., 2012). The study by Solval et al. (2012) suggested the development of air atomized melon juice powder in different temperatures (170 C, 180 C, and 190 C). The authors concluded that vitamin C and β-carotene contained in the juice powder were better preserved in the process with milder temperature. Fonteles et al. (2012) applied ultrasound as preservation method for melon juice. The authors showed that the 376 W/cm2 intensity for 10 min was sufficient for a significant reduction of peroxidase and polyphenol oxidase enzymes, as well as the total inactivation of ascorbate peroxidase. However, the procedure led to a 30% reduction of total phenolic compounds.

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As an alternative to using conventional methods for food preservation, such as pasteurization, the application of ultraviolet light appears as a promising option. A 13.44 W/m2 radiation for 5
20 min was enough to reduce microbial contamination, besides preserving color, the content of total phenolic compounds, and the antioxidant activity of cantaloupe juice (Fundo et al., 2019). Other nonthermal preservative treatments, such as the use of ozone, may also guarantee microbiological safety of foods. Fundo, Miller, Mandro, et al. (2018) applied ozone for 30 and 60 min in cantaloupe juice. They verified that, although the treatment reduced the microbial load, other quality parameters such as color, vitamin C, carotenoids, and antioxidant activity were significantly damaged.

13.2.2 Peels 13.2.2.1 Nutritional composition Studies that utilized melon peel showed that these residues present relevant and high nutritional value, and that they can be used in the development of new, more accessible products, helping overcome the malnutrition problem in developing countries (Go´mezGarcı´a et al., 2020). The peels are mainly composed of carbohydrates, proteins, and pectin, which might enable their use in the production of sweets, increasing commercial value of melon (Rolim et al., 2020). Mallek-Ayadi et al. (2017) studied the phenolic composition and functional properties of peels, and concluded that this by-product can be considered a rich source of carbohydrates, proteins, calcium, potassium, and polyphenols. Gondim et al. (2005) compared the nutritional composition of peels from seven different fruits (avocado, pineapple, banana, papaya, passion fruit, melon, and mandarin), and found that melon peels had higher content of water (93.2%) and lower energetic value (5.18 kcal/100 g). Rolim, Oliveira Junior, et al. (2018) obtained, as results of the proximate composition of cantaloupe peel powder, 8.4% of moisture, 85.6 g/kg of ashes, 36.3 g/kg of lipids, 175.3 g/kg of proteins, 341.8 g/kg of insoluble fiber, 92.4 g/kg of hemicellulose, 190.1 g/kg of cellulose, and 59.3 g/kg of lignin. According to these authors, cantaloupe (C. melo L. var. reticulatus) peel showed good nutritional value and might be adequate for technological implementation, especially due to high levels of fibers and proteins. C. melo L. peels also contain a number of minerals, especially potassium, sodium, magnesium, and calcium. Morais et al. (2017) reported higher levels of calcium (4201.4 mg/100 g) and magnesium (180.5 mg/100 g) in dry melon peels, comparing to other fruits. Potassium was detected in higher amounts in the nonedible parts of cantaloupe, the peels presenting concentration of about 4 mg/g (Fundo, Miller, Garcia, et al., 2018). In a study performed by Sabino et al. (2015), while evaluating the mineral levels in peel flours from tropical fruits, observed that the cantaloupe by-product stood out with 523.24 mg/100 g of potassium, 104.15 mg/100 g of calcium, and 6.62 mg/100 g of iron. In contrast, Mallek-Ayadi et al. (2017) found, in C. melo L. var. maazoun peel, calcium (1153.12 mg/100 g), potassium (884.68 mg/100 g), and magnesium (389.65 mg/100 g) in higher concentrations. Al-Sayed and Ahmed (2013) formulated and produced a cake made with melon and watermelon peel flour, and verified that the new cake batter presented higher amounts of functional compounds, such as fibers, besides effective antioxidant activity, when compared to the

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cake produced with 100% of wheat flour. The authors, then, suggested the replacement of wheat flour at 5% in order for a sensorially acceptable cake to be produced. Vieira et al. (2017) added different concentrations (4.25%, 8.5%, 12.75%, and 17%) of C. melo L. peel flour in cupcakes and verified that, at the level of 12.75%, they were well accepted by children, having sensory acceptance similar to the conventional product. Besides that, the flour increased the quantity of fibers and ashes, improving the nutritional profile of the product. 13.2.2.2 Bioactive composition Gome´z-Garcı´a et al. (2021), while analyzing melon peel separated by mechanical and simple methods, found the presence of polyphenols (hydroxybenzoic and hydroxycinnamic acids) and carotenoids (β-carotene and β-cryptoxanthin), which are responsible for a number of health-improving biological activities. Ezzat et al. (2019) also found that C. melo var. cantalupensis and C. melo var. reticulatus peels presented phenolic acids, including two glycosides and five derivatives from hydroxycinnamic acid, besides flavonoids, especially flavones, flavonols, and isoflavones. Ganji et al. (2019), while studying extracts from dry peel of 12 melon varieties, concluded that organic cantaloupe presents low quantity of total phenolic compounds (0.9 mg GAE/g of extract). Ismail, Chan, et al. (2010) analyzed total phenolic compounds and total flavonoids in cantaloupe peel methanol extracts and found levels of 470 mg GAE/100 g of extract and 513 μg RE/100 g of extract, respectively. On the other hand, El-Tantawy et al. (2016), studying cantaloupe peel hydro-methanolic extract, found lower levels of total phenolic compounds (99.1 mg GAE/100 g) and flavonoids (93.2 mg RE/100 g). According to Rolim et al. (2020), melon peels are rich sources of phenolic compounds such as luteolin (16.51 mg/100 g), chlorogenic acid (8.25 mg/100 g), and apigenin-7-glycoside (29.34 mg/100 g). Vella et al. (2019) found 2548 mg GAE/100 g of polyphenols in cantaloupe peel ethanol extracts. This value is much higher than those reported by El-Tantawy et al. (2016) and Rolim et al. (2020). This difference may be due to several factors, including crop, degree of ripeness, and environmental aspects, such as climate conditions and geographic origin (Cautela et al., 2008; Maietti et al., 2012; Vella et al., 2018). Phenolic acids and flavonoids were quantified by HPLC-PDA at 284 nm, and gallic acid (2.45 mg/g), ellagic acid (0.57 mg/g), and kaempferol (0.32 mg/g) were the main bioactive compounds found in melon peel extract (Vella et al., 2019). Rolim, Fidelis, et al. (2018), while analyzing the profile of phenolic compounds in different extracts from reticulatus melon peel, verified that the hydro-ethanolic extract presented higher quantity of phenolic compounds (703.1 mg GAE/100 g), whereas the aqueous extract showed high content of total flavonoids (262 μg CE/100 g). Morais et al. (2015), while studying C. melo peels, found the presence of high quantity of flavonoids (204.28 mg QE/100 g), besides citric, malic, and tartaric acids, as well as catechin hydrate, epicatechin gallate, epicatechin, epigallocatechin, and epigallocatechin gallate. According to Fundo, Miller, Garcia, et al. (2018), melon peels presented significantly higher value of total phenolic compounds, 141.89 μg/g, compared to juice and pulp. However, while evaluating the concentration of total carotenoids in cantaloupe peels, the authors obtained a value of 23.46 mg/g, which is significantly lower than those found in juice (49.90 mg/g) and pulp (68.92 mg/g). These results demonstrate not only that the edible parts of melon are important sources of healthy compounds, but that it is important to value the residues, since they can be used as ingredients in the production of new products of nutritional appeal.

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El-Tantawy et al. (2016) isolated five compounds in cantaloupe peel hydro-methanolic extract: cucurbitacin, caffeic acid, phytoene, lycopene, and zeaxanthin. Benmeziane et al. (2018) identified the main carotenoids present in cantaloupe peel and found lutein (63.24 μg/g) and β-carotene (56,43 μg/g). Sabino et al. (2015) evaluated cantaloupe peel flour and found 26.27 mg/100 g of ascorbic acid, 64.53 μg/100 g of lycopene, 821.45 μg/ 100 g of β-carotene, and 919.07 mg GAE/100 g of total polyphenols. According to Fundo, Miller, Garcia, et al. (2018), the concentration of vitamin C in cantaloupe peel is 42.76 mg/ 100 g, which is higher than what is found in the seeds. The chlorophylls contained in melon peel are strongly related to the green color aspect and to antioxidant and antimutagenic activities (Delgado-Pelayo et al., 2014). According to Fundo, Miller, Garcia, et al. (2018), the concentration of total chlorophylls present in cantaloupe peels is 78.77 μg/g, represented by chlorophylls a (45.82 μg/g) and b (32.95 μg/g). Tadmor et al. (2010) determined the content of total chlorophylls in different varieties of melon and obtained values ranging from 50 to 750 μg/g in Noy-Amid and late green Tendral, respectively. Regarding the fatty acid composition, according to data reported by Morais et al. (2017), C. melo peels in natura presented higher concentrations of linoleic (19.6 mg/100 g), α-linolenic (19.5 mg/100 g), and palmitic (18.8 mg/100 g) acids. El-Tantawy et al. (2016), studying cantaloupe peel, obtained a different fatty acid profile, in which palmitic (48.1%), α-linolenic (15.7%), and myristic (10.5%) acids stood out. Furthermore, while comparing cantaloupe and banana peels, the authors observed that melon peels presented higher percentage of unsaturated fatty acids (22.8% vs 8.0%).

13.2.3 Seeds 13.2.3.1 Nutritional composition In different countries, melon seeds are salted, roasted, or dried, in order to add flavor to dishes and desserts (Maran & Priya, 2015). Researchers have reported that cantaloupe seeds have medicinal effects (Fundo, Miller, Garcia, et al., 2018; Ismail, Chan, et al., 2010; Rolim, Oliveira Junior, et al., 2018; Silva et al., 2020; Vella et al., 2019). Additionally, the seeds also contain relevant nutritional and bioactive characteristics. The chemical composition of cantaloupe seeds was analyzed by Cunha et al. (2020). The authors found that this residue presents high nutritional capacity, especially regarding the contents of dietary fiber, lipids, and proteins. The values found, on a wet basis, were: 2.64% of moisture, 4.12% of ashes, 30.43% of lipids, 17.64% of proteins, 35.48% of dietary fiber, 9.70% of carbohydrates, and 425.41 kcal of energetic value. In melon seeds from the same variety, Rolim, Oliveira Junior, et al. (2018) found 3.1% of moisture, 3.18% of ashes, 24.56% of lipids, 22.06% of proteins, and 45.32% of dietary fiber, divided into hemicellulose (9.91%), cellulose (35.02%), and lignin (2.39%). Ismail, Chan, et al. (2010) observed that cantaloupe seed methanol extract presents low yield (13.66%), probably due to the low solubility of the lipids, proteins, and starch in these seeds, comparing to the solvent used. Baghaei et al. (2008) used cantaloupe seed extract in the preparation of an orange-based drink. According to the study, cantaloupe seeds presented the following chemical composition: moisture (4.50%), ashes (3.82%), lipids (36.72%), proteins (21.11%), and carbohydrates (33.9%).

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Cantaloupe seeds are also good sources of minerals, especially phosphorus (1507.62 mg/ 100 g), potassium (957.35 mg/100 g), magnesium (504.03 mg/100 g), calcium (36.54 mg/100 g), and sodium (18.50 mg/100 g), besides other micronutrients such as zinc, manganese, iron, and copper. When the contents of magnesium from melon seeds and spinach (79 mg/100 g), which is popularly known as a rich source of this mineral, are compared, it is possible to observe that melon seeds contain six time more magnesium than spinach (Silva et al., 2020). The daily intake of 100 g of melon seed flour meets the requirements established by the National Institute of Health (2020) concerning the consumption of phosphorus for women and men between 9 and 70 years of age. Cunha et al. (2020) suggest replacing part of the wheat flour used in the production of cakes by cantaloupe seed flour. The micronutrients of cantaloupe seeds were also determined by Baghaei et al. (2008), who found 3.41 mg/100 g of sodium, 2.55 mg/100 g of potassium, and 0.24 mg/100 g of iron. Due to the proximate composition of melon seeds, Rolim, Oliveira Junior, et al. (2018) found that C. melo L. var. reticulatus seed flour is a good substrate for growing bifidobacteria, besides being tolerant to the action of bile salts up to 8 h of fermentation. 13.2.3.2 Bioactive composition The phenolic composition of cantaloupe seeds was studied in order to explore its beneficial properties, aiming for possible industrial use (Fundo, Miller, Garcia, et al., 2018; Ismail, Chan, et al., 2010; Vella et al., 2019). The seed methanol extract showed content of total phenolic compounds of 2.85 mg GAE/g of extract (Ismail, Chan, et al., 2010) and 0.23 mg GAE/g of extract (Fundo, Miller, Garcia, et al., 2018). In contrast, the seed ethanol extract resulted in 1.50 mg GAE/g of extract, while its profile of phenolic compounds presented ferulic acid (1.51 mg/g), kaempferol (0.54 mg/g), and gallic acid (0.07 mg/g) (Vella et al., 2019). Flavonoids are the most commonly and widely distributed group of phenolic compounds in vegetables, and they usually have antioxidant capacity. In cantaloupe seed extracts, the values of flavonoids were 1.62 μg RE/g and 0.74 mg CE/g (Ismail, Chan, et al., 2010; Vella et al., 2019). Although the authors expressed the content of flavonoids in different ways, it is possible to affirm that the extracts are sources of natural antioxidants. Tannins, which also belong to the group of phenolic compounds, are an example of antinutrients. The mechanism of action of these compounds involves the chelation of minerals such as iron and zinc, reducing their absorption. They also inhibit digestive enzymes and may precipitate proteins (Silva et al., 2020). Vella et al. (2019), analyzing cantaloupe tannin content, reported 0.74 mg GAE/g of seed extract. Fundo, Miller, Garcia, et al. (2018) determined the values of carotenoids and vitamin C in cantaloupe seed extracts and found 30.51 mg of β-carotene/g and 21.50 mg of vitamin C/100 g of extract, respectively. These numbers were lower than those found in other parts of the fruit, such as the pulp. Between 2008 and 2016, the production of melon in the European Union decreased from 2,274,736 to 1,739,289 tons. Nevertheless, since the seeds represent about 10% of the fruit total weight, approximately 173,929 tons of seeds were discarded. Considering that the oil content may range from 15% to 40%, up to 69,571 tons of melon seed oil could have been produced with this by-product during this period (Rashid et al., 2011; Silva et al., 2020).

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13.2.3.3 Oils C. melo L. seeds are a rich source of oils, which can be either used in food or as biodiesel. For this reason, they are regarded as valuable and economically important (Giwa & Akanbi, 2020). Table 13.1 presents oil contents and extraction methods on different varieties of melon seeds. It is possible to observe that, depending on the extraction method, the oil content may range from 15.20% to 41.60%. This variation might be influenced not only by melon variety and extraction method, but also by weather, time of harvest, and the fruit ripening stage. The extraction technique, besides presenting varied yields, has a significant influence on the composition of the oil obtained. For this reason, the extraction process must be defined according to the purpose of use for the oil (Rezig et al., 2020). Melon seeds have medicinal properties (Rezig et al., 2019) and provide health benefits. Thus, effective oil extraction techniques are required in order to guarantee high quality oil From the chemical point of view, it is impossible to select one most efficient extraction method, since there might be influence from aspects such as type of plant, solvent used, particle size, temperature, and extraction time. Few studies have been found in literature about the physicochemical properties of melon seed oil. Determining these properties, as well as its oxidative stability, could significantly contribute to the application of the oil in cosmetic, pharmaceutical, and food industries (Rezig et al., 2020). Table 13.2 summarizes the physicochemical properties of seed oil from different melon varieties. The content of free fatty acids is an important quality parameter which describes the oil oxidation state. Codex Alimentarius (2009) establishes the content of 2% of free fatty acids as limit. All the oils were within that limit, except for Ananas melon, which presented 4.82% of free fatty acids. Oils of high acidity are more susceptible to oxidation and have short shelf life, since that means their triacylglycerol molecule undergoes integrity loss (Yanty et al., 2008). The peroxide value, along with the content of free fatty acids, TABLE 13.1 Yield in seed oil from different Cucumis melo L. varieties.

Varieties

Oil content (%)

Extraction procedure

References

Agrestis

31.50

Soxhlet/Petroleum ether

Mariod and Mattha¨us (2008)

Reticulates

33.50

Soxhlet/Petroleum ether

Ismail, Mariod, et al. (2010), Ismail, Chan, et al. (2010)

Cantalupensis 29.80

Soxhlet/Petroleum ether

Ismail, Mariod, et al. (2010), Ismail, Chan, et al. (2010)

Reticulates

22.00

Supercritical fluid extraction

Ismail, Mariod, et al. (2010), Ismail, Chan, et al. (2010)

Cantalupensis 15.20

Supercritical fluid extraction

Ismail, Mariod, et al. (2010), Ismail, Chan, et al. (2010)

Inodorus

30.60

Cold extraction/chloroform/ metanol/water

Silva and Jorge (2014)

Honeydew

41.60

Soxhlet/n-hexane

Petkova and Antova (2015)

Maazoun

30.65

Soxhlet/n-hexane

Mallek-Ayadi et al. (2018)

Ananas

28.44

Cold pressing

Rezig et al. (2019)

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TABLE 13.2

Parameters

Physicochemical characteristics of seed oil from different Cucumis melo L. varieties. Inodorus Agrestis (Mariod & Honeydew (Petkova (Jorge et al., Mattha¨us, 2008) & Antova, 2015) 2015)

Free fatty acids 1.85 (%)

Maazoun (MallekAyadi et al., 2018)

Ananas (Rezig et al., 2019)

0.75

0.71

0.31

4.82

Peroxide value (meq O2/kg)




1.10

3.18

0.50

1.04

Iodine value (g I2/100 g)




128

126.70

139.50

128.44

Refractive index (40 C)

1.472




1.467

1.47

1.45

Unsaponifiable matter (%)

0.80

1.00

1.43




1.14

Oxidative stability (h)

5.80

7.20

11.00

7.20

3.74

reflects the oil’s degree of oxidation. The numbers found is several studies are considerably under the limit established by Codex Alimentarius (2009), which is 10 meq O2/kg for refined oils and 15 meq O2/kg for cold pressed oils. Generally, the analyses on free fatty acids and peroxide value show that the oils present good quality. The iodine value corresponds to the number of double bonds present in the oil sample. According to the data presented, it is possible to infer that melon seed oils are predominantly unsaturated. The values found are similar to those established for grape (128
150 g I2/100 g) and soybean (124
139 g I2/100 g) oils. The refractive index increases with the oil’s degree of unsaturation. In melon seed oils, the refractive indexes were close to those found in other unsaturated vegetable oils, such as grape (1.467
1.477) (Codex Alimentarius, 2009). The percentage of unsaponifiable matter ranged from 0.8% to 1.42%. Similar values were found in other studies (Azhari et al., 2014; Lazos, 1986; Yanty et al., 2008). Hydrocarbons, sterols, carotenoids, and liposoluble vitamins are among the components of the unsaponifiable matter. The induction periods for melon seed oils were shorter than those established for other fruits such as grape (15.1 h), passion fruit (61.3 h), pumpkin (65.3 h), and tomato (33.6 h) (Silva & Jorge, 2014). However, comparisons among results must be made cautiously, since the method of oil extraction may influence the compounds that are extracted along with the lipids, which interferes directly with their oxidative stability. The analysis conditions, in other words, temperature and air flow in the Rancimat equipment, may also affect the induction period. Melon seed oils were subjected to 100 C, except for Agrestis melon, which was heated at 120 C. Air flow was established at 20 L/ h, except for Ananas melon, which was 10 L/h. Oil stability is also affected by aspects such as the position of individual fatty acids in the triacylglycerol molecule, in conjunction with the presence of synthetic or natural antioxidants such as tocopherols, carotenoids, and sterols (Kaijser et al., 2000).

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The induction period is also influenced by the fatty acid composition of the sample. The data on the fatty acid profile, including total saturated (SFA) and unsaturated (UFA) fatty acids in seed oil from different melon varieties are shown in Table 13.3. The predominant fatty acid, in all varieties studied, was linoleic acid (58.50%
68.98%), followed by oleic (15.84%
26.40%), palmitic (8.13%
14.43%), and stearic (5.16%
9.75%) acids. The fatty acids α-linolenic, arachidic, and gadoleic were detected in lower concentrations. Therefore, it is possible to conclude that melon seed oil, regardless of melon variety, is characterized by high unsaturation. The fatty acid composition is an indicator of nutritional value of the oil. Linoleic acid, prevalent in melon seed oil, is an essential fatty acid metabolized into arachidonic acid, which is a precursor to prostaglandins and eicosanoids which, in turn, are stimulant to the immune system, vasoconstrictor, and procoagulant (Geranpour et al., 2020). Linoleic acid is usually found in the diet and its main sources are vegetable oils, such as sunflower, corn, and safflower oils. In addition, it is present in seeds from most plants (Codex Alimentarius, 2009). Ismail, Mariod, et al. (2010) analyzed the effect of three supercritical consecutive extractions of seed oils from two cantaloupe varieties. The authors found that, in both varieties, the amount of saturated and monounsaturated fatty acids decreased during the consecutive extractions, while the percentage of polyunsaturated fatty acids increased between the first and the third extractions, in both varieties. Cunha et al. (2020) analyzed the fatty acid profile of C. melo var. reticulatus seed oil and found very similar values to those found by Ismail, Mariod, et al. (2010). The predominant fatty acids were linoleic (63.50%), oleic (15.90%), palmitic (9.10%), and stearic (4.60%).

TABLE 13.3 Fatty acid composition of seed oil from different Cucumis melo L. varieties.

Fatty acid (%)

Agrestis (Mariod & Mattha¨us, 2008)

Reticulates (Ismail, Mariod, et al., 2010; Ismail, Chan, et al., 2010)

Cantalupensis (Ismail, Mariod, et al., 2010; Ismail, Chan, et al., 2010)

Inodorus (Silva & Jorge, 2014)

Honeydew (Petkova & Antova, 2015)

Maazoun (MallekAyadi et al. (2018))

Ananas (Rezig et al., 2019)

Palmitic

9.65

8.13

9.19

8.70

9.40

8.76

14.43

Stearic

9.75

5.16

5.24

5.30

6.60

5.64

5.81

Oleic

16.25

16.13

16.42

26.40

25.00

15.84

23.52

Linoleic

61.35

64.98

64.77

59.00

58.50

68.98

59.26

α-Linolenic 0.20

0.21

0.26







0.20

0.22

Arachidic

0.30

2.49

1.57

0.20

0.10

0.16

0.24

Eicosenoic P SFA P UFA

0.10

2.17

0.27




0.10

0.26




19.70

15.78

16.00

14.20

16.10

14.56

20.48

77.90

83.49

81.72

85.40

83.60

85.28

83.00

UFA/SFA

3.95

5.29

5.11

6.01

5.19

5.85

4.05

SFA, Saturated fatty acid; UFA, unsaturated fatty acid.

Multiple Biological Activities of Unconventional Seed Oils

159

13.2 Botanical description, distribution, and cultivation regions of melon

The types of triacylglycerols are important to evaluate the physical and functional properties of oils and fats (Yanty et al., 2008). The quantity of each triacylglycerol depends on the individual percentage of fatty acids, oil source, and extraction method. Melon seed oils present five main triacylglycerols in their composition: linoleic
linoleic
linoleic (LLL), oleic
linoleic
linoleic (OLL), palmitic
linoleic
linoleic (PLL), oleic
oleic
linoleic (OOL), and palmitic
oleic
linoleic (POL) (Mallek-Ayadi et al., 2018; Rezig et al., 2019; Silva & Jorge, 2014; Yanty et al., 2008). The profile of tocopherols of seed oils from different melon species are shown in Table 13.4. The content of total tocopherols ranged from 137.5 to 507.5 mg/kg in honeydew and Inodorus, respectively, with emphasis on the isomer γ-tocopherol, which prevailed in all oils. The high content of γ-tocopherol may be interesting for commercial use, helping in the development of formulations, since the isomer is the most efficient in the prevention of oxidative processes, acting as antioxidant (Resig et al., 2020). The isomer α-tocopherol, found mainly in the variety Agrestis (77.1 mg/kg), has the highest vitamin E biological activity. From the nutritional point of view, low intake of vitamin E is related to the risk of atherosclerosis and degenerative diseases, since this micronutrient is associated with the inhibition of the oxidation of the low-density lipoprotein (LDLc) fraction, acting as cardioprotective (Silva & Jorge, 2014). While tocopherols are saturated structures, tocotrienols are unsaturated molecules. The content of tocotrienols was measured in Canary melon seed oil, originating from Spain. TABLE 13.4

Profile of tocopherols and main sterols in seed oil from different Cucumis melo L. varieties. Inodorus (Veronezi & Jorge, 2018)

Honeydew (Petkova & Antova, 2015)

Maazoun (MallekAyadi et al., 2017)

Ananas (Rezig et al., 2019)

α-Tocopherol 77.1

39.8

29.0

28.5




β-Tocopherol 3.2




17.0




Parameters

Agrestis (Mariod & Mattha¨us, 2008)

Tocopherols (mg/kg)




γ-Tocopherol 312.0

467.7

91.5

183.0




δ-Tocopherol 1.9







60.9




Total

507.5

137.5

272.4




394.2

a

Sterols (mg/kg) Cholesterol

20.5




8.0

8.8

7.8

Campesterol

16.5




9.0

9.2

53.3

β-Sitosterol

2949.0

797.1

1033.0

2064.2

1923.5

Stigmasterol

25.0




79.0

12.9

134.8

Stigmastanol




60.4










Total

3832.0

857.5

1129.0

2095.1

4849.6

β-Tocopherol 1 γ-tocopherol.

a

Multiple Biological Activities of Unconventional Seed Oils

160

13. Antioxidant and pharmacological activity of Cucumis melo var. cantaloupe

These compounds were found at 0.47 mg/100 g of α-tocotrienol and 0.90 mg/100 g of γ-tocotrienol (Go´rna´s et al., 2015). Besides tocopherols, the oils presented amounts of total sterols between 857.5 mg/kg (Inodorus) and 4894.62 mg/kg (Ananas), β-sitosterol standing out in all samples analyzed (Table 13.4). Phytosterols are bioactive compounds found in food of plant origin. Clinical studies suggest that the intake of 2 g/day of phytosterols is associated with significant reduction of 8%
10% in the level of LDLc. As typical western diet only contains about 300 mg/day of phytosterols, foods fortified with this compound are commonly used in order to meet the necessary daily intake (Cabral & Klein, 2017; Racette et al., 2010). Other bioactive compounds were also investigated in melon oils. Veronezi and Jorge (2018) studied Inodorus melon seed oil and found high content of total phenolic compounds (145.29 mg/kg). Mallek-Ayadi et al. (2018) investigated the profile of phenolic compounds in Maazoun melon oil and found gallic (7.26 μg/g), protocatechuic (0.89 μg/g), caffeic (3.13 μg/g), and rosmarinic (2.91 μg/g) acids, as well as luteonin-7-O-glycoside (9.6 μg/g), naringenin (4.72 μg/g), apigenin (3.88 μg/g), flavone (1.94 μg/g), amentoflavone (32.80 μg/g), oleuropein (1.65 μg/g), and pinoresinol (3.95 μg/g). In Ananas melon oil, caffeic (1.98 μg/g), vanillic (2.31 μg/g), ferulic (134.83 μg/g) acids, oleuropein (2.31 μg/g), and pinoresinol (10.88 μg/g) were quantified (Rezig et al., 2019). Nyam et al. (2009) identified other phenolic acids such as gallic, protocatechuic, p-hydroxybenzoic, vanillic, caffeic, syringic, p-coumaric, and ferulic in Kalahari melon seed oil. Phenolic compounds constitute part of the unsaponifiable matter in oils and fats and determine characteristics such as flavor, oxidative stability, and shelf life (Mariod & Mattha¨us, 2008). The level of carotenoids was also determined in oils extracted from some melon seeds. These bioactive compounds are useful from the technological point of view, as they act as pigment and have antioxidant property, since they suppress the singlet oxygen. Their benefits for human health, such as prevention of cardiovascular diseases, prostate cancer, and macular degeneration, are also reported (Resig et al., 2020). Silva and Jorge (2014) found 6.3 μg β-carotene/g of oil in Inodorus melon seed oil obtained by cold extraction with solvent mixture. The same oil presented 31.33 μg β-carotene/g when extracted with hexane by Soxhlet, in a study performed by Veronezi and Jorge (2018). These numbers were higher than those found in Mashhadi melon oil, 3.4 μg β-carotene/g (Hashemi et al., 2017), and in Maazoun melon seed oil, 2.43 μg β-carotene/g (Mallek-Ayadi et al., 2019).

13.3 Antioxidant and pharmacological properties The Cucurbitaceae family is broadly used in the medical field due to the presence of potentially therapeutic compounds. These compounds contain antiinflammatory, antimicrobial, and antitumor properties, as well as hemolytic properties, being highly toxic when injected into the bloodstream (Lima et al., 2010). Although melon presents low quantities of vitamin E, folic acid, iron, and calcium, the daily intake of five to eight portions of melon is recommended in order to ensure adequate nutrition and fight hypertension, conditions of the skin, and anemia, besides controlling gout, rheumatism, obesity, and constipation, and treating cardiovascular diseases (Milind

Multiple Biological Activities of Unconventional Seed Oils

13.3 Antioxidant and pharmacological properties

161

& Kulwant, 2011). The fruit is also used by popular medicine as tranquilizer, diuretic, and laxative (Senar
Servic¸o Nacional de Aprendizagem Rural, 2010). Studies have shown that cantaloupe has useful medicinal properties, such as analgesic, antiinflammatory, antioxidant, antiulcer, anticancer, antimicrobial, diuretic, and antidiabetic activities. In addition, it presents hepatoprotective effect, activity against hypothyroidism, and immunomodulating action (Ismail, Chan, et al., 2010; Milind & Kulwant, 2011; Vouldoukis et al., 2004). Muller et al. (2013), while studying the phytochemical potential of melon crops, concluded that cantaloupe shows higher quantity of flavonoids. Flavonoids are substances that have several properties, such as antiinflammatory, antimicrobial, antifungal, and antioxidant (Longhini et al., 2007). The residues from the processing of melon also have a number of properties that are beneficial to the body, such as easy maintenance of kidney functions, antirheumatic properties, indigestion treatment, etc. (Vishwakarma et al., 2017). In addition, they show high antioxidant capacity, especially due to the presence of specific compounds such as phenolics and flavonoids (Silva et al., 2020). Vella et al. (2019) verified that cantaloupe residues are a good source of natural phytochemicals used for a number of purposes, such as ingredients for the nutraceutical, cosmetic, or pharmaceutical industries, as well as the development of functional ingredients and new foods, and the production of fertilizers and animal feed.

13.3.1 Leaves Ismail, Chan, et al. (2010), while evaluating different parts of the cantaloupe plant, such as leaves, stem, peel, seed, and pulp, observed that the leaf extract has higher content of total phenolic compounds (26.2 mg GAE/g of extract), especially total flavonoids (69.7 μg RE/g of extract), besides the most satisfactory antioxidant activity (4.43 αTE/g of extract). This result suggests that melon leaf extract may contain primary antioxidant compounds that are capable of reacting, particularly, with hydroxyl radicals, delaying the formation of hydroperoxides (Shahidi et al., 1992). Hashemi et al. (2019), while studying extracts from C. melo leaves, found, through three different methods (percolation, Soxhlet, and ultrasound), higher potential of antioxidant activity in the methanol extract obtained by percolation (IC50 5 115 μg/mL).

13.3.2 Pulp Research developed by Vouldoukis et al. (2004) showed that cantaloupe pulp extract, both in vitro and in vivo, has significant antioxidant and antiinflammatory properties. Fundo, Miller, Garcia, et al. (2018) analyzed antioxidant activity in C. melo L. var. reticulatus pulp, peel, and seeds, and verified that the pulp presents the lowest antioxidant activity, 220.38 μg AAE/g of extract. Amaro et al. (2013) studied the effect of 1-methylcyclopropene on the changes in the phytochemical compounds of C. melo var. cantalupensis “Fiesta,” and also reported low antioxidant activity, 153.3 μg AAE/g. In contrast, Brito (2017), while studying the presence of phytochemicals of antioxidant capacity in C. melo L. pulp and peel, found that the pulp, by DPPH• analysis, had higher antioxidant capacity (60.6 mg/mL) than the peel (49 mg/mL). Studies performed on pulp concentrate from melon that is rich in superoxide dismutase enzyme (SOD) showed antioxidant and antiinflammatory effects. Furthermore, the results

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13. Antioxidant and pharmacological activity of Cucumis melo var. cantaloupe

suggested physical, cognitive (focus, fatigue), and behavioral (irritability, difficulty in bonding) performance increase (Carillon et al., 2013; Saby et al., 2020). Naito et al. (2005) found that the oral administration of extracts from melon rich in SOD, covered by wheat gliadin polymeric films, to rodents preclinically diagnosed with type 2 diabetes, prevented the progression of oxidative stress-induced diabetic nephropathy. Kick et al. (2007) used cantaloupe extracts, chemically combined with wheat gliadin, catalase (10 UI/mg), glutathione peroxidase (1 UI/mg), and SOD (100 UI/mg), in the diet of 18 domestic pigs, and concluded that, in an oral pretreatment, the use of this extract may be an adjuvant measure in elective surgery and/or used as nutritional care in extended periods of high oxidative stress. In general, other authors who analyzed the supplementation of melon SOD combined with gliadin support its use as complementary treatment instead of a therapeutic treatment (Romao, 2015). Xavier et al. (2020) evaluated the effect of different levels of pulp concentrate of melon rich in SOD on Oreochromis niloticus growth and antioxidant capacity, and verified that gradual integration of this concentrate in the fish diet did not show difference in their growth. However, it showed antioxidant activity through FRAP method, which allowed to conclude that supplementation of the concentrate at levels higher than 0.4% contributes to better maintenance of the antioxidant defense of Nile tilapias.

13.3.3 Peels Melon peel extracts have shown the presence of phytochemical compounds of antioxidant, antimicrobial, antidiabetic, antiviral, antiinflammatory, antihypoglycemic, and antiproliferative effects in several in vitro and in vivo tests (Go´mez-Garcı´a et al., 2020). Studies show that cantaloupe residues, especially the peels, are good sources of natural phytochemicals, useful for various purposes, such as ingredients for nutraceutical, cosmetic, or pharmaceutical industries, as well as in the development of functional ingredients and new foods, and in the production of fertilizers and animal feed (Fundo, Miller, Garcia, et al., 2018; Vella et al., 2019). Ganji et al. (2019), while studying extracts from dry peels of 12 melon varieties, found that organic cantaloupe presented low antioxidant activity, 0.14 mg AAE/mL of extract. On the other hand, Rolim, Fidelis, et al. (2018) analyzed the antioxidant activity and the antiproliferative effect of different C. melo var. reticulatus peel extracts on cancer cells, and found positive correlation (r 5 0.823) between phenolic compounds and flavonoids with antioxidant activity in the hydro-ethanolic extract. Fundo, Miller, Garcia, et al. (2018) showed that the antioxidant activity in cantaloupe peels is 336.78 μg AAE/g of extract, probably due to the presence of polyphenolic compounds, especially phenolic acids and flavonoids. El-Tantawy et al. (2016), while evaluating the antioxidant activity of hydromethanolic extracts from banana and cantaloupe peels and guava pulp, found that melon peel presented higher antioxidant activity with the lowest IC50 value (0.1019 mg/mL). According to Brito (2017), in a study that aimed to evaluate the presence of phytochemicals of antioxidant potential in two types of melon, cantaloupe and Matisse, found that the DPPH• scavenge activity was higher in C. melo var. cantalupensis peel (49 mg/mL). This result shows that the antioxidant capacity of a sample is related to the content of phenolic compounds. Asghar et al. (2013) analyzed different types of melon peel extract and found

Multiple Biological Activities of Unconventional Seed Oils

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163

the presence of hydrocarbons, aldehydes, ketones, saturated and unsaturated fatty acids, including some cyclic analogs, phenolic compounds, anthocyanin derivatives, etc. In addition, the authors concluded that the content of phenolic compounds is responsible for the antioxidant nature and the ability to eliminate radicals, especially in extracts in which methanol and n-hexane were used as solvents. Parmar and Kar (2009), while investigating the pharmacological importance of peel extracts from different fruits, regarding possible regulation of tissue lipid peroxidation, thyroid disorders, lipid metabolism, and glucose in rats, found that the combined administration of the three extracts increased the thyroid hormone (T3) and, simultaneously, decreased tissue lipid peroxidation. The authors also verified that C. melo peel extract reduced the concentrations of total and LDL cholesterols. Sabino et al. (2015) analyzed the antioxidant activity in peel flour from several tropical fruits, including cantaloupe, which presented 27.4 μM Trolox/g of peel flour. In this study, the authors also investigated positive correlations between copper (r 5 0.730), manganese (r 5 0.742), and polyphenols (r 5 0.952) with the antioxidant activity. Ezzat et al. (2019) studied the antiinflammatory activity in vivo in ethanol extracts from C. melo var. cantalupensis and C. melo var. reticulatus, and observed that, after 3 h, there was a significant edema inhibition effect, especially on rats that had received C. melo var. reticulatus peel extract at 50 mg/kg concentration. The antiinflammatory action may be related to phenolic compounds, since studies show that gallic, ferulic, caffeic, and ρ-coumaric acids inhibit from 30% to 40% the tumor necrosis factors (TNF-α) and from 60% to 75% interleukin 6 (IL6) activity (Nile et al., 2016).

13.3.4 Seeds There are several reports about the fact that C. melo seeds reduce cardiovascular disorders, help regulate lipid levels in the blood, control type 2 diabetes, besides being a good source of natural antioxidants (Chen & Kang, 2013; Zeb, 2016). A study carried out with rats showed that the seed methanol extract presented analgesic and antiulcer activities. These activities may be connected to the reduction of vascular permeability, generation of free radicals, and lipid peroxidation, due to the presence of carrageenans, triterpenoids, and sterols (Gill et al., 2011). Ismail, Chan, et al. (2010) observed that the methanol extract from cantaloupe seeds presented low quantity of flavonoids, 1.62 μg RE/g of extract, and, consequently, low antiradical (37.37 g DMSOE/g of extract) and antioxidant (IC50 5 25.4 mg/mL) activities. Vella et al. (2019), while evaluating the ethanol extract from cantaloupe seeds, observed low antioxidant (0.31 mg AAE/g) and antiradical (55.03 mg/mL) activities, and they also attributed these results to the content of polyphenols, ortho-diphenols, flavonoids, and tannins. According to Chang et al. (2001), low antioxidant and antiradical activities are probably due to the redox properties in the existing compounds, which enable them to act as reducing agents, hydrogen donors, and singlet oxygen inhibitors. In contrast, a study carried out by Fundo, Miller, Garcia, et al. (2018) showed that C. melo L. var. reticulatus seeds have high antioxidant activity (653.67 μg AAE/g of extract) when compared to other parts of melon, confirming the research performed by Contreras-Caldero´n et al. (2011), which indicates that the seeds are an important source of natural antioxidants. Ibrahim et al. (2016) identified a triterpenoid (Cucumol A) in C. melo var. reticulatus seed methanol extracts. This compound presented cytotoxic activity against cancer cells.

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13. Antioxidant and pharmacological activity of Cucumis melo var. cantaloupe

Zhang et al. (2020) analyzed the cytotoxic activity of different melon seed extracts against cancer cells in the prostate (PC-3), human colon (HCT116), and against lymphocyte cells (JurKat), and found that chloroform extract had higher antioxidant activity against all cell lines when compared to the others. In addition, the seed extract showed higher cytotoxicity against the cell line HCT116. C. melo L. seed essential oil has high antibacterial activity against S. aureus and other grampositive bacteria (Siddeeg et al., 2014). Rezig et al. (2019) observed that C. melo seed oil has higher antioxidant activity and is more stable against lipid oxidation, compared to seed oils from other fruits in the Cucurbitaceae family. Furthermore, the authors also found a linear correlation between the antioxidant activity in these seed oils and the oxidative stability. Veronezi and Jorge (2018), while studying C. melo var. inodorus seed oil, determined the high capacity of phenols to reduce the Fe13-TPTZ complex into Fe12-TPTZ complex at pH 3.6, since the antioxidant capacity was 185.9 μM Trolox/100 g. With this result, it is possible to infer that this oil contains high quantity and/or different types of phenolic compounds (Jardini et al., 2010).

13.4 Conclusions In this chapter, it was possible to learn about a few characteristics of C. melo L., especially cantaloupe, regarding its origin, distribution, cultivation, natural composition, bioactive compounds, and antioxidant and pharmacological activities. All parts of the fruit (pulp, peels, and seeds) present important technological, functional, and nutritional properties, as well as capacity for the development of new products, due to the presence of high content of bioactive compounds, especially phenolic compounds, carotenoids, and fatty acids. These compounds are responsible for the benefits that C. melo L. presents to human health, since they have analgesic, antiinflammatory, antioxidant, antiulcer, anticancer, antimicrobial, and antidiabetic properties, besides having a hepatoprotective effect and immunomodulating action. Further studies must be carried out to help enhance industrial applicability and guarantee extensive exploration of C. melo L. by-products, in order to increase its potential use in foods, cosmetics, medicines, and, also, reduce environmental impact.

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Multiple Biological Activities of Unconventional Seed Oils

C H A P T E R

14 Pumpkin seed oil components and biological activities Mohamed A. Gedi1,2 1

Division of Food, Nutrition and Dietetics, School of Biosciences, University of Nottingham, Sutton Bonington Campus, Loughborough, United Kingdom 2Faculty of Agriculture and Environmental Science, Somali National University, Mogadishu, Somalia

14.1 Introduction Pumpkin flesh and seeds have long been used not only as a food but also as traditional medicines in several countries including Argentina, Brazil, India, Korea, China, and Mexico (Jia et al., 2003; Andrade-Cetto & Heinrich, 2005; Di Stasi et al., 2002, Yadav et al., 2010). The food crop originated from Mexico as its center for domestication and diversification, and is generally grown in tropical and subtropical regions (Castellanos-Morales et al., 2019; Paris, 2016). Today, pumpkin is widely cultivated all over the globe as a vegetable or as an ornamental plant. This medicinally and economically important plant belongs to the genus Cucurbita of the family Cucurbitacea. Pumpkin comprises of mainly five species, namely Cucurbita maxima, Cucurbita pepo, Cucurbita moschata, Cucurbita argyrosperma, and Cucurbita ficifolia, with C. maxima, C. pepo, and C. moschata being three of the most cultivated species and most economically important worldwide (Caili et al., 2006a; Ferriol & Pico´, 2008). Another pumpkin species which is also economically viable in certain parts of the world is Telfairia occidentalis, known as fluted pumpkin. This latter species is largely cultivated in parts of West African countries including Nigeria (South), Ghana, and Sierra Leone (Dhiman et al., 2009). The current top 10 world
leading countries in pumpkin production are listed in Table 14.1. Owing to the presence of key biologically active components such as high levels of proteins, peptides, polysaccharides, phytosterols, antioxidants vitamins (carotenoids and tocopherols), unsaturated fatty acids and minerals, pumpkin flesh and seeds received greater attention as a functional food and pharmaceutical ingredients (Durante et al., 2014). Among the antioxidant vitamins and minerals present in pumpkin flesh and seeds are

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00030-1

171

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172

14. Pumpkin seed oil components and biological activities

TABLE 14.1 Production of pumpkin in different countries Country

Production (tonnes)

Area (ha)

Yield (kg/ha)

China

7,838,809

425,230

18,434.3

India

5,073,678

528,753

9,595.6

Russia

1,224,711

57,012

21,481.6

Ukraine

1,209,810

58,600

20,645.2

USA

1,005,150

41,640

24,139

Mexico

677,048

36,721

18,437.7

Indonesia

603,325

8,828

68,342.2

Italy

580,188

18,486

31,385

Cuba

518,862

57,018

9,100

Turkey

489,999

106,697

4,592.4

Data in the table was obtained from Atlasbig (2020) and FAOSTAT.

β-carotene and β-cryptoxanthin (precursors of vitamin A), α-tocopherol (the major form of vitamin E abundant in nature, with the most biological activity), ϒ-tocopherol, B-complex vitamins, vitamin C, and minerals such, calcium, magnesium, potassium, iron, zinc, and selenium (Amin et al., 2019; Kim et al., 2012; Priori et al., 2017; Bjørneboe et al., 1990). The chemical composition of different parts of pumpkin species (flesh, peel, and seed) is provided in table 14.2.

14.2 Pumpkin botany The name given to a group of plant species from the genus Cucurbita of the family Cucurbitaceae are known as pumpkin. These include C. maxima, C. pepo, C. moschata, C. ficifolia, C. argyrosperma and Telfairia occidentalis (known also as fluted pumpkin). Pumpkin is a monecious creeping or climbing plant and resistant to nonfrost low temperatures. It has five vigorous, slightly angular stems and 5
25 cm ovate-cordate to suborbicularcordate petioles around the leaves, with or without white spots on the surface (Yadav et al., 2010). The fruit ranges greatly in size from few ounces to giant pumpkin that can reach over 34 kg. Some varieties are green, gray, yellow or red, but the skin of pumpkin is generally orange in color. Although it may differ from one species and variety to the other, the seeds are large oval-shaped, flat and end in a tip. An example of this is the seeds of C. maxima, with an approximate weight between 50 and 250 mg. The seed coat is completely filled by the embryo, consisting of spherosomes, small spherical lipid bodies, and protein organelles, which are stored in the cotyledons (Sinavimo, 2020; LemusMondaca et al., 2019).

Multiple Biological Activities of Unconventional Seed Oils

TABLE 14.2 Macro and micronutrient composition of pumpkin spp (raw). Nutrient

Moisture

Protein

Lipid

Ash

Carbs.

Fiber

Part

a

Ref. (Kim et al., 2012)

b

Ref. (Amin et al., 2019)

g/100

g/100

Flesh

91.68 6 6.7

92.45

peel

85.48 6 9.1

Seed

Mineral

Part

c

Ref. (Amin et al., 2019)

mg/100 Flesh

20.760

89.52

peel

9.650

5.11 6 2.3

56.7

Seed

1.350

Flesh

0.54 6 0.5

0.79

Flesh

1616.390

peel

1.23 6 0.3

1.54

peel

687.470

Seed

29 6 1.7

9.22

Seed

434.710

Flesh

0.18 6 0.2

0.11

Flesh

42.070

peel

0.66 6 0.2

0.17

peel

4.004

Seed

47.36 6 4.4

10.14

Seed

6.017

Flesh

0.811 6 0.4

0.41

Flesh

0.820

peel

1.05 6 0.4

0.77

peel

1.360

Seed

5.08 6 0.6

1.53

Seed

4.000

Flesh

6.77 6 5.8

0.64

Flesh

0.230

peel

11.56 6 8.3

1.30

peel

0.150

Seed

13.05 6 0.9

2.24

Seed

18.777

Flesh

0.73 6 0.35

0.12

Flesh

1.363

peel

2.30 6 1.1

1.40

peel

1.419

Seed

13.95 6 2.8

20.18

Seed

0.740

Flesh

0.450

Component

mg/100

Na

K

Fe

Ca

Zn

P

Mn

α-Tocopherol

Seed

*0.208

-

peel

0.360

β-Carotene

Seed

*0.314

-

Seed

1.350

β-Cryptox.

Seed

*0.021

-

Flesh

5.643

Mg

c

Ref. (Glew et al., 2006)

mg/100

0.69

579

10.6

34.6

11.3

1570

4.9

(Continued)

TABLE 14.2 (Continued) Nutrient

Part

a

β-Sitosterol

Seed

*0.235

FAs 16:0 18:0 18:1 18:2 18:3 a

Seed oil Seed oil Seed oil Seed oil Seed oil

Part

c

-

peel

3.353

%

mg/100

Seed

4.340

*10.84

†

20.78

Flesh

0.060

*5.84

†

4.52

peel

0.025

*14.83

†

25.42

Seed

0.310

1.5

*56.60

†

49.42

Seed

-

0.13

*0.24

†

2.25

Ref. (Kim et al., 2012)

b

Ref. (Amin et al., 2019)

Mineral

Cu

Se

Ref. (Amin et al., 2019)

c

Ref. (Glew et al., 2006)

569

Values are averaged from three pumpkin species (Cucurbita maxim, Cucurbita pepo, and Cucurbita moschata) and converted from mg/kg to g/100 g. Based on the moisture content of each plant part, values were converted from dry weight into wet weight for ease of comparison between the studies and expressed in wet weight basis. Mineral composition of pumpkin plant parts (C. maxima) and pumpkin seeds (C. spp) are expressed in dry weight basis. Note: Values with asterisk (*) are expressed in concentration (% fat) of PSO. Values with crucifix (†) are expressed in mg/100 g in PSO (represent C. maxima). β-Cryptox., β-Cryptoxanthin; Ref., reference; FAs, fatty acids.

b c

175

14.3 Composition of pumpkin seed oil

14.3 Composition of pumpkin seed oil 14.3.1 Fatty acid profile of pumpkin seed oil The content of oil in pumpkin seeds ranges between 400 and 540 g/kg (Procida et al., 2013). Fatty acid profile of PSO from selected various studies in the recent decade is presented in Table 14.3. PSO is composed of two saturated fatty acids, palmitic acid (16:0) and stearic acid (18:0), as well as two unsaturated fatty acids, oleic (18:1) and linoleic (18:2) as its major constituents. The essential fatty acid, linoleic is the predominant fatty acid in PSO, followed by oleic acid and palmitic acid (Li et al., 2020). Alpha-linolenic acid, another essential and more biologically active fatty acid is also present in most pumpkin species but with significantly lower concentrations compared to other unsaturated fatty acids, particularly oleic and linoleic acid. The level of unsaturated fatty acids in PSO is considered high. Based on the recent studies (Table 14.3) the level of unsaturated fatty acids in PSO (Cucurbitaspp) ranges from nearly 67%
91% of the total fatty acids. An exception is a fluted pumpkin (T. occidentalis) where oleic acid (38%) is the predominant (rather than linoleic acid) fatty acid followed by palmitic (27%) and steric acid (1.43%). Yet total unsaturated fatty acids of T. occidentalis are considerably as high as those of Cucurbita spp (60%) (Ajayi et al., 2004). TABLE 14.3

Fatty acid profile of pumpkin seed oil from various studies. Fatty acid

Species

Reference

14:0 16:0

16:1 17:0 18:0 18:1

18:2

18:3 20:0 TUFA

Cucurbita. Spp

(Li et al., 2020)

14.21

7.29 33.39 45.10

78.49

C. mixta

(Shelenga et al., 2020)

15.50

6.00 29.60 48.70 0.20

78.50

aCucurbita spp

(Ferreira et al., 2019)

0.14 17.04

C. maxima

(Montesano et al., 2018)

0.2

C. maxima

(Ali et al., 2017)

0.17 18.90 0.11

bpepo

(Herna´ndez-Santos et al., 2016)

C. pepo

(Benalia et al., 2015)

0.14 20.00 0.26 0.29

Cucurbita. Spp

(Jiao et al., 2014)

0.68 13.71 0.14 0.07 5.99 24.63 53.72 0.18 0.88 79.55

C. maxima

´ et al., (Nawirska-Olszanska 2013)

13.10

6.00 35.90 42.60 0.25

78.75

C. moschata

(Kim et al., 2012)

12.79

7.33 31.34 35.72

67.06

cC. pepo

(Salgin & Korkmaz, 2011)

9.59

7.46 32.35 48.48 0.60

81.43

Cucurbita spp

(Szterk et al., 2010)

6.24

1.95 32.64 58.17 0.17 0.13 91.11

T occidentalis T. occidentalis

(Ajayi et al., 2004)

27.45

1.43 38.17 25.05

10.7 31.39 39.83

0.73 71.95

14.20 0.20 0.20 5.80 41.40 37.00 0.20 0.5

18.07

7.7

79.30

33.90 37.90 0.70 0.13 72.74

8.98 35.03 38.01

73.04

29.30 46.50 1.00 1.5

a

Cucurbita. spp: Fatty acid data is based on conventional extraction using hexane. Pepo: Values are averaged from the extraction conditions of fatty acids (13 runs) reported by Herna´ndez-Santos et al. (2016). Cucurbita pepo: Condition of supercritical CO2 extraction time and pressure was (MPa) 40 and 20, respectively.

b c

Multiple Biological Activities of Unconventional Seed Oils

78.56

0.40 63.62

176

14. Pumpkin seed oil components and biological activities

Seed oil fatty acid composition can be used to evaluate its shelf life and nutritional quality. Whilst a high degree of unsaturated fatty acids in oils can lead to more susceptibility to oxidation, there is a substantial amount of data recommending the reduction of saturated fatty acids and moderate increase of unsaturated fatty acids, particularly those of polyunsaturated fatty acid (PUFA). Replacement of saturated fatty acids with unsaturated fatty acid enhances lipid profile in the blood which, its turn, reduces the risk in certain chronic diseases like cardiovascular.

14.3.2 Bioactive compounds of pumpkin seed oil In the literature, several bioactive compounds with biological activity have been reported in PSO. Rabrenovi´c et al. (2014) who studied major forms of bioactive compounds in PSO highlighted tocopherols, sterols, and squalene besides fatty acids as the most important bioactive components in cold press PSO (C. pepo). A similar study on the influence of roasting on PSO bioactive components selected phenolic compounds, tocopherols, and antiradical activity as the prime target of the study (Potoˇcnik et al., 2018). The influence of species (C. argyrosperma vs C. moschata) and extraction method (mechanical pressing vs organic solvent) on the composition of bioactive components of PSO was further studied by Can-Cauich et al. (2019). Bioactive compounds investigated in the study included phenolic compounds, carotenoids, tocopherols, sterols, and squalene. 14.3.2.1 Tocopherols in pumpkin seed oil Tocopherols are found in plant tissues and in oil seeds in the form of methyl tocols or benzopynarols. For tocopherols, the C16 side chain is saturated, whereas for tocotrienols, three trans double bonds are found in the C16 side chain. These two groups combined are known as tocochromanols (Christ, 2014). Tocochromanols are strong lipid-soluble antioxidants, abundant in seed oils and in other plant tissues (e.g., chloroplasts). These compounds are essential constituents of animal and human diets (Dellapenna & Pogson, 2006). Tocochromanols comprise of four tocopherols and four tocotrienols that collectively constitute vitamin E, and are essential nutrients in the diet of all mammals (Dellapenna & Pogson, 2006). Vitamin E is protective against several diseases, such as cancer, cardiovascular diseases and DNA damage by oxidation of radicals and low-density lipoproteins (Gey & Puska, 1989). Alpha-tocopherol is the major form of vitamin E found in nature, with the most biological activity, and is favourably stored in large quantities to be transported to body components (Bjørneboe et al., 1990). Several studies in the literature report the effectiveness of PSO as a potential preventive diet against prostate disease and progression of hypertension, kidney stones, and arthritis (Andjelkovic et al., 2010; Medjakovic et al., 2016; Potoˇcnik et al., 2016; Procida et al., 2013). The mechanism of the oil’s action physiologically is largely attributed to the presence of high quantities of the antioxidant vitamin E, existing mainly in the form of α- and γ-tocopherols (Naziri et al., 2016; Potoˇcnik et al., 2018; Procida et al., 2013).

Multiple Biological Activities of Unconventional Seed Oils

14.3 Composition of pumpkin seed oil

177

14.3.2.2 Phenolic compounds in pumpkin seed oil Phenolic compounds are secondary metabolites found in the vast majority of plant tissues including fruits, vegetables, and their seed oils. Due to their bioactive properties these phytochemicals promote some protection against numerous diseases. As mentioned earlier, reports suggest that PSO is a potential preventive diet against prostate disease and progression of hypertension, kidney stones, and arthritis (Andjelkovic et al., 2010; Medjakovic et al., 2016; Potoˇcnik et al., 2016; Procida et al., 2013). This is not only because of the presence of high levels of vitamin E in PSO, but also due to the existence of substantial amounts of phenolic compounds in the oil. Among the phenolic compounds (phenolic acids and flavonoids) present in the oil are chlorogenic acid, caffeic acid, p and o-coumaric acids ferulic acid, 4-hidroxybenzoic, 2-hydroxycinnamic, quercetin, trans-cinnamic acid, vanillic acid, and chrysin. These polyphenols are found in the PSO with varying concentrations depending on the species, variety, and method of extraction (Can-Cauich et al., 2019; Potoˇcnik et al., 2018). 14.3.2.3 Carotenoids in pumpkin seed oil Carotenoids are a group of compounds exclusively found in photosynthetic organisms including, plants, algae, certain fungi, and bacteria. These are the components responsible for the pigmentation of species and organisms such as the red, orange, and yellow colors of many fruits, vegetables, flowers, and microorganisms (Britton et al., 2012; Gedi et al., 2017; Gedi et al., 2019). These pigments constitute a group of over 700 structures belonging to the C40-based isoprenoid family, known as tetraterpenes. Carotenoids are classified into two main groups which are carotenes (e.g., α-carotene, β-carotene, and lycopene) and xanthophylls (e.g., β-cryptoxanthin, lutein, zeaxanthin, neoxanthin, and violaxanthin). Carotenes are purely hydrocarbons and are well recognized for their lack of oxygen whereas, xanthophylls possess oxygen within their carbon chain (Britton et al., 2012; Gedi et al., 2019). Like tocopherols and phenolic compounds carotenoids are considered as bioactive components with protective properties and biological activity against various diseases, particularly the reduction of the incidence of cancers and eye disease (Jomova & Valko, 2013). Carotenoids of xanthophyl family, namely lutein, zeaxanthin and β-cryptoxanthin and those of nonoxygenated carotenoids (e.g., β-carotene, a provitamin A) are the major carotenoids in PSO (Can-Cauich et al., 2019; Procida et al., 2013; Akin et al., 2018). 14.3.2.4 Phytosterol and squalene in pumpkin seed oil Phytosterols are the cholesterol (animals) equivalents found in plants and consist of sterols and stanols. Those phytosterols commonly found in our diet include, campesterol, stigmasterol, and β-sterol. They are widely found in the unsaponifiable lipid fraction of foods such as, grains, seeds, nuts, and vegetable oils (Ryan et al., 2007). Studies suggest that phytosterols reduce low density lipoproteins (LDL-C) or the bad cholesterol by about 10% (recommended: 2 g/day intake of phytosterols) and thus, may decrease cardiovascular diseases (Katan et al., 2003; Abumweis et al., 2008; Gylling et al., 2014; Kaur & Myrie, 2020). Paradoxically based on other studies, phytosterols may contribute to the risk of

Multiple Biological Activities of Unconventional Seed Oils

178

14. Pumpkin seed oil components and biological activities

coronary diseases (Sudhop et al., 2002; Rajaratnam et al., 2000; Assmann et al., 2006), showing that there is a big controversy on phytosterols prevention effect against cardiovascular diseases. Numerous other biological activities of phytosterols have also been reported, including anticancer, antiinflammatory, and antidiabetic properties (Woyengo et al., 2009; Miras-Moreno et al., 2016; Bae et al., 2020). Squalene, on the other hand, is an isoprenoid compound with a similar structure as β-carotene and intermediates in the formation of cholesterol. Squalene which can be sourced from both animals and plants is abundant in nature. Considered as a strong antioxidant, squalene possesses a protective effect against certain cancers such as chemically induced colon, lung, and skin cancers (Smith, 2000). PSO is one of the good sources of phytosterols and squalene. Ryan et al. (2007) who investigated phytosterol, squalene, and other bioactive compounds in selected seeds, grains, and legumes reported that pumpkin seed contained high concentrations of both compounds (24.9 mg/100 g and 89.0 mg/100 g seed, respectively for phytosterol and squalene; the basis of the values, i.e., dry weight basis vs fresh weight basis or the moisture content of the samples were not reported within the study). Phytosterols and squalene are further concentrated in the oil of pumpkin seeds (Can-Cauich et al., 2019; Rabrenovi´c et al., 2014). Major bioactive components in PSO with proven biological activity and health promotion are presented in Table 14.4.

14.4 Antimicrobial, antiinflammatory and antidiabetic properties of pumpkin seed oil Due to its richness in potent bioactive compounds including tocopherols, phenolic compounds, carotenoids, phytosterols, and squalene, PSO exhibits numerous biological functionalities including antimicrobial, antiinflammatory, and antidiabetic properties.

14.4.1 Antimicrobial property of pumpkin seed oil PSO samples screened against several standard bacterial, fungal, and viral strains showed high antimicrobial activity on Klebsiella pneumoniae and Acinobacter baumannii at a concentration of 16 μg/mL, but with insignificant inhibition against the rest of the bacteria. The oil samples also exerted a selective inhibitory effect on the fungal species, Candida albicans and the virus, Parainfluenza virus (Type-3), while they were completely inactive against Herpes simplex (virus). However, the range of activity on Parainfluenza virus (Type-3) was quite narrow (16
8 μg/mL) when compared to oseltamivir (32- , 0.25 μg/mL) (Sener et al., 2007). Bardaa et al. (2016) evaluated the impact of PSO on the wound healing of rats and reported the efficient inhibition of oil from pumpkin seeds against Gram-positive but not Gram-negative bacteria, and named Bacillus subtilis as the inhibiting bacteria. They concluded that PSO is a potential candidate to prevent spoilage caused by Bacillus. However, a different study on the antimicrobial activity of 52 plant oils and extracts

Multiple Biological Activities of Unconventional Seed Oils

179

14.4 Antimicrobial, antiinflammatory and antidiabetic properties of pumpkin seed oil

TABLE 14.4

Composition of major bioactive compounds in pumpkin seed oil.

Tocopherols (mg/kg oil)

Cucurbita maxima

Cucurbita pepo

Cucurbita moschata

α-Tocopherol

1280

51
98

ϒ-Tocopherol

1136a

356
619c

15.24h

Lutein

93
121d

0.556h

Zeaxanthin

98
116d

-

a

c

28.39h

Carotenoids (mg/kg oil)

β-Carotene

b

36.2

β-Cryptoxanthin

e

7.63h

4.3
4.9e

0.15h

0.78
3.87f

137.68h

5.19
10.0f

35.90h

5.4
6.0

Sterols (mg/100 g oil) Sitosterol

50.64a

Stigmasterol

3.17a

β-Sterol

197.3h

Fucosterol Phenolic acids (mg/kg oil) Caffeic acid

38.8a

0.03
0.09c

Syringic acid

79.6a

76
80e

Vanillic acid

24.6a

0.37
0.96c

a

c

p-Coumaric acid

25.0

Ferulic acid

49.9a

Trans-cinnamic acid

-

Squalene (mg/kg oil)

0.60
0.96

0.99h 0.37h

0.61
0.96c 1645
1795g

3290h

a

Rezig et al. (2012), bCuco et al. (2019), cPotoˇcnik et al. (2018), dProcida et al. (2013), eAkin et al. (2018), fHrabovski et al. (2012), Naziri et al. (2016), hCan-Cauich et al. (2019).

g

(agar dilution method was used) suggested that PSO failed to inhibit any of the selected organisms (Hammer et al., 1999).

14.4.2 Antiinflammatory property of pumpkin seed oil The in vivo biological activity (antiinflammatory property) of PSO and of other seed oils (prickly pear and linseed) was examined on a group of rats and results demonstrated that seed oils, pumpkin included, were efficient in acute inflammation treatment (Bardaa et al., 2020). This study suggested that the antiinflammatory property of PSO is mainly due to its antioxidant properties and the bioactive compounds in its composition, including unsaturated fatty acids, tocopherols, and phytosterols.

Multiple Biological Activities of Unconventional Seed Oils

180

14. Pumpkin seed oil components and biological activities

A similar study by De Oliveira et al. (2013) evaluated the efficiency of PSO as a remedy for acute and chronic skin inflammation and reported that due to the unsaturated fatty acids present, PSO is an alternative therapy for the treatment of skin diseases caused by inflammation. Based on this study, the oil also showed similar efficacy as that of dexamethasone, a steroid medicine, and a copy of a hormone that humans produce naturally. The mechanism of the oil’s action was attributed to the alteration of inflammation response by means of cellular and molecular modulation, in which inflammatory pathways are activated by phlogistic agents (xylene, 12-O-tetradecanoylphorbol acetate (TPA) and oxazolone) (De Oliveira et al., 2013). An earlier study by Fahim et al. (1995) employed PSO for the treatment of rat arthritis and compared it with reference antiinflammatory drug called indomethacin. Findings of this study indicated that PSO successfully modulated most of alterations caused by arthritis and was as effective as indomethacin.

14.4.3 Antidiabetic property of pumpkin seed oil Fruit pulp and the seed of pumpkin have exhibited antidiabetic activity in animal studies including alloxan-induced diabetic rabbits and rats. Powders from pumpkin significantly decreased blood glucose whilst increasing plasma insulin in the blood (Caili et al., 2006b; Zhang & Bai, 2004; Chen et al., 2005). One study employing type 2 diabetic Wistar rats accounted for the antidiabetic property of pumpkin for the tocopherols in the seed composition of C. pepo, and concluded that the seed tocopherols reduced prediabetics to progress into diabetics (Bharti et al., 2013). PSO from C. pepo and C. maxima has also alleviated urinary disorders during oral administration of a human study (Nishimura et al., 2014).

14.5 Conclusion PSO is an edible oil with nutritional and medicinal functionalities that can be included in our daily diets. Health-promoting properties of PSO include its anticholesterol, anticancer, antimicrobial, antiinflammatory, and antidiabetic activities. These biological activities by PSO are largely due to its bioactive components such as its high unsaturated fatty acids (mainly linoleic and oleic), tocopherols (including α- and ϒ-tocopherols), carotenoids (e.g., lutein, zeaxanthin, β-carotene, and β-cryptoxanthin), phenolic compounds (e.g., phenolic acids and flavonoids), and phytosterols plus squalene. Although pumpkin seed is a rich source of these valuable bioactive compounds, it is thrown away as a waste in many parties of the world, hence, greater attention needs to be paid to pumpkin seed valorization in agro-food industry.

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7058. Montesano, D., Blasi, F., Simonetti, M. S., Santini, A., & Cossignani, L. (2018). Chemical and nutritional characterization of seed oil from Cucurbita maxima L.(var. Berrettina) pumpkin. Foods, 7, 30. ´ Nawirska-Olszanska, A., Kita, A., Biesiada, A., Soko´ł-Łe˛towska, A., & Kucharska, A. Z. (2013). Characteristics of antioxidant activity and composition of pumpkin seed oils in 12 cultivars. Food Chemistry, 139, 155
161. Naziri, E., Miti´c, M. N., & Tsimidou, M. Z. (2016). Contribution of tocopherols and squalene to the oxidative stability of cold-pressed pumkin seed oil (Cucurbita pepo L.). European Journal of Lipid Science and Technology, 118, 898
905. Nishimura, M., Ohkawara, T., Sato, H., Takeda, H., & Nishihira, J. (2014). Pumpkin seed oil extracted from cucurbita maxima improves urinary disorder in human overactive bladder. Journal of Traditional and Complementary Medicine, 4, 72
74. De Oliveira, M. L. M., Nunes-Pinheiro, D. C. S., Bezerra, B. M. O., Leite, L. O., Tome´, A. R., & Gira˜o, V. C. C. (2013). Topical anti-inflammatory potential of pumpkin (Cucurbita pepo L.) seed oil on acute and chronic skin inflammation in mice. Acta Scientiae Veterinariae, 41, 1
9. Paris, H. S. (2016). Overview of the origins and history of the five major cucurbit crops: Issues for ancient DNA analysis of archaeological specimens. Vegetation History and Archaeobotany, 25, 405
414. Potoˇcnik, T., Ogrinc, N., Potoˇcnik, D., & Koˇsir, I. J. (2016). Fatty acid composition and δ13C isotopic ratio characterisation of pumpkin seed oil. Journal of Food Composition and Analysis, 53, 85
90. Potoˇcnik, T., Rak Cizej, M., & Koˇsir, I. J. (2018). Influence of seed roasting on pumpkin seed oil tocopherols, phenolics and antiradical activity. Journal of Food Composition and Analysis, 69, 7
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Multiple Biological Activities of Unconventional Seed Oils

C H A P T E R

15 Antioxidant and pharmacological activity of watermelon (Citrullus lanatus) seed oil Abdel Moneim Elhadi Sulieman1,2 and Salwa Elamin Ibrahim3 1

Department of Food Engineering and Technology, University of Gezira, Wad Medani, Sudan Department of Biology, College of Science, University of Hail, Hail, Kingdom of Saudi Arabia 3 Department of Home Economic, College of Home Economic, King Khalid University (KKU), Abha, Kingdom of Saudi Arabia

2

15.1 Introduction It is believed that watermelon originated and spread from Africa or from hot valley regions in southwestern Asia, particularly Iran and India, and from there it gradually began to appear in Europe with the near end of the Western Roman Empire (Jules, 2012). It is known that the ancient Egyptians cultivated watermelons, however, recent discoveries of melon seeds dating from between 1350 and 1120 BC and discovered in the sacred Nuragic Wells, have shown that watermelon was first brought to Europe by the Nuragic civilization in Sardinia during the Bronze era (Vaughan et al., 2009). There is an urgent and continuous need to uncover new antimicrobials with diverse chemical compositions and mechanisms of action valuable because there is an increase in the incidence of new and recurrent infectious diseases and another big reason is the increase in resistance to antibiotics. Biotechnology is used continuously, and at the present time scientists have resorted to conducting new research on plants to overcome microbial resistance to antibiotics and access to natural immune-boosting remedies, plants have the potential to manufacture compounds as secondary metabolites found in seeds, leaves, or roots (Ajeena et al., 2007; Aqil et al., 2006; DeSouza et al., 2005).

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00027-1

185

© 2022 Elsevier Inc. All rights reserved.

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15. Antioxidant and pharmacological activity of watermelon (Citrullus lanatus) seed oil

Watermelon was among the oldest plants brought from the wild and cultivated on farms in the ancient world and also among the first types of crops that Westerners brought to the New World. According to records, early European settlers in the New World cultivated honeycomb and casaba melons as early as the 17th century. It is also reported that a number of Native American tribes in New Mexico preserve the tradition of cultivating varieties of watermelon distinctive and their own, which dates back to watermelons that were brought by the Spaniards in the past and preserved (Denise, 2008). It is known that antioxidants are positively charged molecules that merge with a group of free, negatively charged atoms, making them harmless: We define antioxidants as natural or chemical substances added to food to prevent fat oxidation (fat spoilage) and this is the action of antioxidants if they are added to food. It is to prevent the formation of raw materials from oxidation, which is called free radicals, and among the antioxidants found in food are vitamin C, vitamin E, and citric acid (lemon). These antioxidants work to protect food from corruption and rancidity and protect the body from many different diseases such as heart disease, atherosclerosis, and cancer. Therefore, it is advised to consume foods that contain these vitamins and minerals, such as vegetables and fruits (http://site.iugaza.edu.ps/rhashish/). Watermelon seed is one of the neglected seed on the planet which is regularly disposed of in the wake of eating the fruit. Explores show that these seeds contain supplements like protein, fundamental unsaturated fats, nutrients and minerals (Sarfaraz et al., 2020). Oil content in the seeds is between 35% and 40% and the unsaturated fat in oil is 78%
86% prevalently linoleic acid (45%
73%). Watermelon seeds are utilized for oil extraction. The seeds are dried and oil is separated by squeezing them. This practice is regular in West Africa and the watermelon seed oil is prominently known as Ootanga oil or Kalahari oil. Oil is utilized as searing? oil in different African countries (Reetapa et al., 2018). Watermelon contains small amounts of phenolics as well as low vitamin C content compared with other fruits (Maria, 2006). Intake of lycopene containing-products has been associated with a reduced incidence of coronary heart disease and some types of cancer (Naz et al., 2014). Researchers believe that there is still a huge number of antiinfection materials that have not been discovered in nature. In addition, to date, only 10% of all vascular plants (containing vessels to transport fluids inside) have been examined to search for medicinal compounds that may contain them. In addition, researchers face difficulties in identifying previously discovered plants because plants that have been identified as sources of active compounds are not consistently documented. Plants and their metabolites are often given names that differ from one region to another. The objectives of the present study was to evaluate the antioxidant and pharmacological activity of watermelon seed.

15.2 Significance of medicinal plants Since prehistoric times, medicinal plants have been an important resource for fighting disease and infection. One of the biggest challenges in developing natural medicines is finding new herbs with protective health effects. It is known that humans rely specifically on medicines from natural sources for disease control, because pathogens are constantly

Multiple Biological Activities of Unconventional Seed Oils

15.5 Fatty acids content

187

evolving and producing new strains (Reference). The proportion of antibiotics used today were originally obtained from natural compounds found in plants, fungi, bacteria, and marine organisms is estimated to be more than 70%. Seeming well and good for looking through the new wide range antimicrobial to treat the microbial illness much consideration has been engaged toward plant extracts and biologically active compounds confined from famous plant species. The utilization of medicinal plants plays a unique role in covering the essential health needs in developing countries and these plants may offer a new source of antibacterial, antifungal, and antiviral agents with noteworthy activity against infective microorganisms (Rana et al., 2014).

15.3 Proximate chemical composition of watermelon The proximate chemical composition of watermelon plant seed is presented in Table 15.1. As shown in the table, the content of moisture, ash, crude protein, crude fiber, ash, lipids and carbohydrate ranged between 10.3 6 0.1%, 16.20 6 0.3%, 5.64 6 0.1%, 7.72 6 0.02%, 3.12 6 0.2%, and 57.02 6 0.1%, respectively.

15.4 Minerals content Watermelon plant seed contained variable amounts of macro-minerals potassium (K), Calcium (Ca) and Magnesium (Mg) which was 421.5
70.9 μg/mL, 343.1
2.46 μg/mL and 72.1
11.911.9 μg/mL (Table 15.2) (Fig. 15.1).

15.5 Fatty acids content Table 15.2 revealed the identification of the fatty acids and the dicarboxylic acids of seeds of the oil watermelon by gas chromatography/mass spectrometry (GC-Ms). The fatty acids which were found in various amounts included: Octadecanoic acid methyl ester, dodecanoic acid methyl ester, methyl tetradecanoate methyl ester, TABLE 15.1

Chemical composition of watermelon (Citrullus vulgaris) Seeds.

Parameter

Content (%)

Previous results from literature

Moisture (%)

10.30 6 0.1

3.08
9.45 (Anthony, 2015; Zubairu et al., 2018)

Crude protein

16.20 6 0.3

15.49
21.46 (Anthony, 2015; Zubairu et al., 2018)

Ash (%)

5.64 6 0.1

1.0
6.46 (Anthony, 2015; Zubairu et al., 2018)

Crude fiber (%)

7.72 6 0.02

2.73
55 (Anthony, 2015; Zubairu et al., 2018)

Lipid (%)

3.12 6 0.2

1.101
41.84 (Anthony, 2015; Zubairu et al., 2018)

Carbohydrates (%)

57.02 6 0.1

19.45
59.03 (Anthony, 2015; Zubairu et al., 2018)

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15. Antioxidant and pharmacological activity of watermelon (Citrullus lanatus) seed oil

TABLE 15.2 Identification of dicarboxylic fatty acids in watermelon seed by gas chromatography/mass spectrometry. Peak Name 1

Structure

GC-MC analysis O

Octadecanoic acid

CH3

O

2

Dodecanoic acid O

H3 C

3

Methyl tetradecanoate

O

6 O

4

O

Pentadecanoic acid

7 O

5

O

Hexanoic acid

O

6

O

Hexadecanoic acid O

7

8

8
11-Octadecadienoic acid,

O

O

O

Eicosanoic acid

O

9

Hexadecanoic acid, 15-methyl

O oH

O

pentadecanoic acid methyl ester, hexanoic acid methyl ester, hexadecanoic acid methyl ester, 8
11-octadecadienoic methyl ester, eicosanoic acid methyl ester, and hexadecanoic acid, 15-methyl-, methyl ester. The most abundant fatty acid was hexanoic and eicosanoic acids with a concentration percentage of 15%, followed by Hexadecanoic, methyl tetradecanoate and Pentadecanoic acids with a concentration percentage of 14%. On the other hand, the least detected fatty acid was octadecanoic acid with a percentage of 9%.

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15.6 General phytochemical screening of the watermelon plant seeds

15.6 General phytochemical screening of the watermelon plant seeds The results for the general phytochemical screening of all parts of the watermelon plant seeds are shown in Table 15.3. Phytochemical screening of the aqueous and other organic solvents extracts show that, sterols and triterpenes, carotenoids, reducing compounds, saponinns, glycosides, alkaloids compounds, and carbohydrates were present in the extracts with varying amounts. In the present study, results showed that various parts of watermelon plant contain different phytochemical compounds such as sterols triterpenes, glycosides, and saponinns. Plants are a noteworthy source of medication from which most medication mixes exude. Therapeutic phytochemicals have utilized as model possibility for the blend of concoction medications and pharmaceuticals. Late increment in logical knowledge of the chemical composition and action of plant mixes brought about potential chances to fix a wide assortment of diseases (Jaison Jeevanandam et al., 2016). FIGURE 15.1 Mineral contents (μg/mL) of watermelon (Citrullus vulgaris) seeds.

TABLE 15.3

General phytochemical screening of all parts of SP1. Class of chemical compounds

Watermelon seed 111

1

Sterols and triterpenes

2

Carotenoids

3

Reducing compounds

4

Saponinns (saponosides)

5

Glycosides

6

Alkaloids compounds

-

7

Phenoloic compounds

-

8

Carbohydrates

1

Multiple Biological Activities of Unconventional Seed Oils

1 11 111

190

15. Antioxidant and pharmacological activity of watermelon (Citrullus lanatus) seed oil

The role of these phytochemicals as antimicrobial has been reported by many researchers (Bello et al., 2016; Hassan et al., 2011; Okorondu et al., 2010; Saxena, et al., 2013). Presence of phytochemical in watermelon plant was reported by many authors including (Bello et al., 2016; Braide et al., 2012; Godwin et al., 2015; Nwankwo et al., 2014). However, the variation in the types and amounts of phytochemicals and other active ingredients could be affected by the geographical location. Existence of these phytochemicals in the extract was an unmistakable sign of antimicrobial possibilities of the various parts of watermelon plant. Antibacterial activity of the plant extracts demonstrated that all tested microorganisms were susceptible. Watermelon seeds have been reported by many investigators to possess powerful pharmacological activities (Fig. 15.2). The potency of the oil compared with standard diclofenac (10 mg/kg) showed a significant reduction of edema in carrageenan-induced rat paw edema model maximum at 3 hours [percentage reduction in paw volume 44.44%, 55.56%, and 63.11% for CLSO (50 mg/kg), CLSO (100 mg/kg) and diclofenac (10 mg/kg)(Erhirhie & Ekene, 2013; Madhavi, et al., 2012). An in vitro antigiardial activity of watermelon fruits, petroleum ether, ethyl acetate, butanol crude extracts was investigated by Loiy et al. (2011), based on the results, they concluded that C. lanatus var. citroides might be recommended as new source for the treatment of giardiasis. The antioxidant, antiinflammatory and analgesic potential of watermelon seed extract in rodent model was carried out by Erhirhie and Ekene (2013). The free radical scavenging activity of all extracts was measured by DPPH and H2O2 methods. They found that the methanolic extract of the seeds showed highest antioxidant activity. 200 mg/kg of the seed extract showed significant, antiinflammatory and angels tic activity. Their findings might be used as a future food medicine (Gill et al., 2010).

FIGURE 15.2

Pharmacological properties of watermelon seed.

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191

15.7 Antimicrobial activity of the watermelon plant

15.7 Antimicrobial activity of the watermelon plant The antimicrobial activities of the water and solvents extracts of all parts of the watermelon seeds are shown in Table 15.4 and Figs. 15.3 and 15.4. The highest antimicrobial TABLE 15.4

Antimicrobial activity of watermelon plant seeds extracted with ethanol.

Microorganism

Inhibition zone diameter (mm)

E. coli

22

Bacillus subtilis

18

Staphylococcus aureus

15

Candida albican

11

FIGURE 15.3 Growth inhibition of Staphylococcus aureus (A) and Bacillus subtilis (B) bacteria against watermelon plant seeds. FIGURE 15.4 Growth inhibition of Candida albicans yeast against watermelon seed extract.

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15. Antioxidant and pharmacological activity of watermelon (Citrullus lanatus) seed oil

activity was only against the E. coli bacteria. Their respective inhibition zones had diameters of 20 and 22 mm. However, the methanol extracts of the watermelon plants seeds of the watermelon plants showed very low antimicrobial activity against the fungus Candida albicus. On the other hand, the antimicrobial activities of methanol extracts of the seeds was highest against the E. coli. Their respective inhibition zones had diameters of 20 and 22 mm. However, the methanol extracts of the watermelon plant seed showed very low antimicrobial activity against the fungus, Candida albicus. As shown in Fig. 15.5, the petroleum ether exhibited more potency on Bacillus subtilis and E. coli bacterial in contrast to the aqueous water extract which produced less impact on Bacillus subtilis and the yeast Candida albicans. On the other hand, other solvents extracts (chloroform, ethanol, butanol, and methanol) exhibited high potency on E. coli, Bacillus subtilis (B.s), staphylococcus aureus (S.a) bacteria, and Candida albicans yeast (Ca. a). In addition, C. albicans was the most inhibited microorganism compared with the other tested microorganisms. Moreover, the ethanol extract was the most efficient solvent. When comparing with the findings of other researchers, Braide, et al. (2012) observed that aqueous extracts shows a better response to the antibacterial activities than the ethanol whereas Nwankwo et al. (2014) reported the contrary. This inconsistency may be a component of methodological contrasts and strain inconstancy. The present study, demonstrated antimicrobial activity of petroleum ether, chloroform, ethanol, ethyl alcohol, butanol methanol of roots, stems, leaves, green crus, white crust, kernel, and seeds from watermelon against bacteria [Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and fungi (Candida albican)]. These results were in agreement with those reported by Adelani et al. (2015) and Gupta et al. (2018). Almost all extracts of watermelon plant including water extract except ether extract showed significant antifungal activity. Earlier study on the primary phytochemical screening of these extracts demonstrated the presence of wide range of phytoconstituents along with antifungal compounds.

FIGURE 15.5

Antimicrobial activity of watermelon plant seeds using various solvents.

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References

193

Susceptibility of Staphylococcus aureus and E. coli showed in the present study agreed with that Joana Monte et al. (2014) who demonstrated the potential of phytochemicals to control the growth of these microorganisms in both planktonic and biofilm states. Adunola et al. (2015) attributed susceptibility of S. aureus to presence of saponins in watermelon plant. Therefore, our findings therefore, support the view that other phytochemicals are active against Gram-positive bacteria also. Several researchers examined the impact of plants extracts and their active ingredients like antimicrobial agents to control harmful bacterial development. Some researchers proposed that antimicrobial compounds of the plant extracts such as terpenoid, alkaloid, and phenolic compounds, interface with proteins and enzymes of the cell membrane making its disruption to disperse a flux of protons toward the cell exterior which prompts cell death or may restrain enzymes vital for amino acid biosynthesis (Burt, 2004; Gilland Holley, 2006).

15.8 Conclusion The present investigation legitimizes that extracts of all parts of the watermelon plant have promising activity against a wide scope of microorganisms in charge of most common microbial diseases and infections and thus give the prospect of finding new clinically powerful antimicrobial mixes. In this manner, further research is important to recognize the capable mixes inside these plants and to decide their full range of adequacy too. Moreover, as plants contain an assortment of phytochemicals, proficient extraction, isolation, and purification procedures are required to get the ideal antimicrobial phytochemical so as to explicitly describe its potential adequacy. Isolation and purification of phytochemicals in the extract may likely exert more effect like the commercial antibiotic.

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9. Gill, N. S., Bansal, R. K., Garg, M., Sood, S., Muthuraman, A., & Bali, M. (2010). Evaluation of antioxidant, antiinflammatory and analgesic potential of Citrullus lanatus seed extract in rodent model. The Internet Journal of Nutrition and Wellness, 9(2). Godwin, O. O., Williams, A. U., Andrew, N. A., Atoyebi, B., Ezeh, P. A., & Udosen, I. J. (2015). An assessment of the phytochemicals and antibacterial activity of seed extract of Citrullus lanatus (watermelon). International Journal of Research & Review, 2, 148
156. Gupta, A., Singh, A., & Prasad, R. (2018). A review on watermelon (Citrullus lanatus) medicinal seeds. Journal of Pharmacognosy and Phytochemistry, 7(3), 2222
2225. Hassan, L. E. A., Sirat, H. M., Yagi, S. M. A., Koko, W. S., & Abdelwahab, S. I. (2011). In vitro antimicrobial activities of chloroformic, hexane and ethanolic extracts of Citrullus lanatus var. citroides (watermelon). Journal of Medicinal Plant Research, 5, 1338
1344. Jaison Jeevanandam., Aing, Y. S., Chan, Y. S., Pan, S., & Danquah, M. K. (2016). Chapter 3 - Nanoformulation and application of phytochemicals as antimicrobial agents. antimicrobial nanoarchitectonics. From Synthesis to Applications 2017 (pp. 61
82). Elsevier. Joana Monte., Abreu, A. C., Borges, A., Simo˜es, L. C., & Simo˜es, M. (2014). Antimicrobial activity of selected phytochemicals against Escherichia coli and Staphylococcus aureus and their biofilms. Pathogens, 3(2), 473
498. Jules, Janick. (2012). Plant Breeding Review. Volume 9511181004843535: 35 (p. 88, 978111810048688). John Wiley & Sons. Loiy, E. A. H., Hasnah, M. S., Yagi, S. M. A., Koko, W. S., & Abdelwahab, S. I. (2011). In vitro Antimicrobial activities of chloroformic, hexane and ethanolic extracts of Citrullus lanatus var. citroides (Wild melon). Journal of Medicinal Plants Research, 5(8), 1338
1344. Madhavi P., et al. (2012). Hepatoprotective activity of Citrullus lanatus seed oil on CCl4 induced liver damage in rats, Scholars Academic Journal of Pharmacy, 1(1), 30
33 Maria Cecilia do Nascimento Nunes. (2006). Color Atlas of Postharvest Quality of Fruits and Vegetables. Wiley.com. https://books.google.com.sa/books?id=hvNCSnihtf8C&hl=ar&source=gbs_navlinks_s. Naz, A., Butt, M. S., Sultan, M. T., Qayyum, M. M., & Niaz, R. S. (2014). Watermelon lycopene and allied health claims. EXCLI J., 13, 650
660, Published 2014 Jun 3. Nwankwo, I. U., Onwuakor, C. E., & Nwosu, V. C. (2014). Phytochemical analysis and antibacterial activities of citrulluslanatus seed against some pathogenic microorganisms. Global Journal of Medical Research, 14, 17
22. Okorondu, S. I., Sokeri, T. G., Akujobi, C. O., & Braide, W. (2010). Phytochemical and antimicrobial properties of musa paradisiacal stalk plant. International Journal of Biological Sciences, 2, 128132. Reetapa Biswas et al. (2017). A comprehensive review on watermelon seed oil – an underutilized product. IOSR Journal of Pharmacy, 7(11). Rana, S. M. R., Billah, M. M., Barua, S., Moghal, M. M. R., Raju, G. S., & Islam, M. M. (2014). A study on Erioglossumrubiginosum for evaluation of biological properties. Journal of Health Science, 4(1), 18
23. Sarfaraz Athar, Abullais Ghazi, Osh Chourasiya, Dr. Vijay Y. Karadbhajne. (2020). Watermelon seed oil: its extraction, analytical studies, modification and utilization in cosmetic industries. International Research Journal of Engineering and Technology (IRJET). 7(2). Feb 2020. Saxena, M., Saxena, J., Rajeev, N., Dharmendra, S., & Gupta, A. (2013). Phytochemistry of medicinal plants. Journal of Pharmacognosy and Phytochemistry, 1, 168
182. Vaughan, J. G., Geissler, Catherine; Nicholson, Barbara. (2009). Food crops in; Oxford book of food plants. New York : Oxford University Press. Isbn: 9780199549467-019954946X. Zubairu, A., Gimba, A. S. B., Mamza, W. J., & Highina, B. K. (2018). Proximate analysis of dry watermelon (Citrullus lanatus) rind and seed powder. Journal of Scientific and Engineering Research, 5(3), 473
478.

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C H A P T E R

16 Rice bran oil main bioactive compounds and biological activities Norazalina Saad1, Norsharina Ismail2, Siti Nurulhuda Mastuki2, Sze Wei Leong1, Suet Lin Chia1,3 and Che Azurahanim Che Abdullah1,4,5 1

UPM - MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 2Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 3Department of Microbiology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, Serdang, Malaysia 4Department of Physics, Faculty of Science, Universiti Putra Malaysia, Serdang, Malaysia 5Materials Synthesis and Characterization Laboratory, Institute of Advanced Technology (ITMA), Universiti Putra Malaysia, Serdang, Malaysia

Abbreviations CAT cyt C CLA DISC FADD GPx HDL-C LDL-C MUFA NF-κB PUFA PPAR RB RBO ROS SFA

Catalase Cytochrome C Conjugated linoleic acid Death-inducing signal complex Fas-associated protein with death domain Glutathione peroxidase High density lipoprotein cholesterol low density lipoprotein cholesterol Monounsaturated fatty acids nuclear factor-κB Polyunsaturated fatty acids Proliferator-activated receptor Rice bran Rice bran oil Reactive oxygen species Saturated fatty acid

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00017-9

195

© 2022 Elsevier Inc. All rights reserved.

196 SOD TC TG VLDL-C γ-T3

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Superoxide dismutase Total cholesterol Triglycerides Lipoproteins include very low density lipoprotein cholesterol γ-tocotrienol

16.1 Introduction Rice (Oryza sativa L.) is the predominant staple food of almost half the global population, representing for about 20% of the caloric consumption of the worldwide community (Cordero-lara, 2020). It was anticipated that the global rice production would achieve 497.8 million tons throughout 2019 and 2020 (Nathanchildsusdagov, 2019). Rice is the primary cereal in majority of Asian countries, and feeds more people over a longer period than any other crops (OECD-FAO Agricultural Outlook 2020
2029, 2020). The whole grain is milled after the harvesting stage is completed, in relation to supply the white rice that is the most widely eaten worldwide. However, approximately 40% of the grain is lost as a by-product in the milling process, and this amount typically varies, including rice variety, cultivation procedures and technology applied (Bodie et al., 2019). Husks, bran, germ and broken rice, that are normally removed or utilized as food for animals, are the by-products from different milling stages. Rice bran (RB) is the outer layer of rice grains that comprises up to 15%
25% lipids and potentially be a nature source of a variety of biologically active compounds. Rice bran oil (RBO) is a lipid found in RB that has a great balance of unsaturated and saturated fatty acids (Tong & Bao, 2018). RBOs are high in bioactive phytochemicals like oryzanol, tocotrienols, and tocopherols, which have been shown to have nutritional benefits. Rice lipids, which are mostly found in the bran, embryo, and endosperm fractions, are essential in influencing rice storage, processing, and cooking quality (Liu et al., 2013). Therefore, many believe that RBO is one of the healthiest and very valuable edible oils, because it has considerable nutritional values and functional properties that are useful for the food industry.

16.2 Rice milling and by-products The method of obtaining edible white rice kernels after extracting the outermost layer of grains and any potential impurities is the rice milling process (Bodie et al., 2019). This method is commonly intended for commercial purposes as it involves a complex process that focuses on producing a higher number of good-quality outputs. The whole grain is known as “rice” and typically consists of a husk, bran, rice grain or starchy endosperm, and rice germ or germ (Fig. 16.1). The outer shell is the outer layer that, during development, protects the inner core. It is not nutritious and the rice can be quickly removed (peeling or peeling process). Rice husk is used primarily by thermal processes, such as gasification and combustion, for the production of energy.

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16.3 Rice bran

FIGURE 16.1

Illustration of rice plant (left) and rice grain (right). Adapted from BioRender.com.

The rice milling step can be distributed into three phases. A one-step milling process occurs when the husk and bran layer is separated in a single process and white rice is generated directly from the paddy. On the other hand, a two-step milling process involves the separate removal of the husk and the bran layer, producing brown rice as an intermediate product (Bodie et al., 2019). Rice undergoes a few separate operations, and the machine from rice to white rice is called a multistage milling process (Prabhakaran et al., 2017). The entire milling process produces over 30% of the by-products, consisting of rice husk, bran, germ, and broken rice, which are abundant in nutrients and valuable molecules (Fraterrigo Garofalo et al., 2020). Some of the wheat grains are broken during the complete milling step. Broken grains are usually recognized by their length, in which not more than three-quarters of the entire grain is counted to be broken grains, and are normally converted to flour afterward further used in food production (Dhankhar, 2014).

16.3 Rice bran RB is a part of the grain, composed of peel or hull and aleurone layer, located in the middle of the shell and endosperm (Fig. 16.2), and is detached when the brown rice is refined to get white rice (Sonia Cozzano et al., 2018). RB contains 5%
8% of the total weight of rice grains and comprises 11%
13% crude protein, B11.5% fiber, and B20% fat (Sonia Cozzano et al., 2018). RB includes carbohydrates (34%
62%), lipids (15%
20%), protein (11%
15%), fiber (7%
11%), additional minerals, and trace elements (Sivamaruthi et al., 2018). The composition depends on several external factors, including plant species, environmental agronomic conditions, and processing (Sonia Cozzano et al., 2018). RB, which is commonly used in the food industry, has recently been introduced into the nutrition, healthcare and pharmaceutical industries due to its advantages for human wellbeing (Gul et al., 2015). However, RB can only be utilized to inactivate lipase after the

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FIGURE 16.2 Diagram of rice bran layers comprising of pericarp and aleurone layer. Adapted from Raghav, P. K., Agarwal, N., & Sharma, A. (2016). Emerging health benefits of rice bran—A review. International Journal of Multidisciplinary Research and Modern Education, II (I), 367
382.

stabilization process. Such steps limit rancidity and help to sustain the value of RB throughout storage (Fraterrigo Garofalo et al., 2020). Therefore, several technologies for bran stabilization have been introduced and studied: these technologies include boiling, chemical method, oven baking method, ohmic heating technology, residual moisture heating, additional moisture heating, and dry heating at atmospheric pressure, extrusion cooking, microwave heating and infrared heating. The most effective method, according to many researchers, is the microwave heating, which is a cheap and fast process that can generate products with a small amount of free fatty acids and remain stable over time. RB can be used directly or processed in other ways after stabilization to generate high-value products for the food, nutraceutical, and pharmaceutical industries. RB oil is one of the most prevalent commercial goods obtained in the processing of RB (Fraterrigo Garofalo et al., 2020; Jiang, 2019).

16.4 Rice bran oil Depending on the type of rice, milling process, and stabilization system, RB can contain up to 25% RBO. It’s an edible oil with a numerous health benefits that’s widespread in India, Korea, Japan, and the United States (Fraterrigo Garofalo et al., 2020). There are three general techniques used for the extraction of RBO, such as hydraulic pressing, X-M milling, and solvent extraction (Nagendra Prasad et al., 2011). Solvent extraction is the most normally applied technique for the extraction of oil. This is due to the yield has been shown to achieve as 0.549 g RBO/g bran and the solvent be able to simply eliminated via a number of purification phases (Chiou et al., 2013). Most commercial extractions use hexane, an organic petroleum-derived solvent as it yields the most oil, compared to other types of solvent. Although hexane is widely accepted, it possesses some drawbacks, in which it be able to influence the color and is deliberated harmful (Nagendra Prasad et al., 2011). Following the extraction, the RB is separated into two categories: crude RB oil and defatted rice. Crude RBO contains of 4% unsaponified (wax, fat, and oil), 4% free fatty acids

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and 90% lipids. Crude RBO can be enhanced by removing free fatty acids, which is essential for improving rancidity and sensory characteristics (Siddiqui et al., 2010). In addition, innovative technologies can also be used to extract and refine RBO (Punia et al., 2021). Innovative green extraction technologies usually include technology that enhances the procedure, for example ultrasound, microwave, supercritical fluid, subcritical water, pulsed electric field, enzyme extraction, ultrafiltration, and pressurized hot water (Fraterrigo Garofalo et al., 2020). Most of these emerging technologies have achieved encouraging results in extracting highly effective bioactive compounds (especially natural antioxidants) from various resources (such as plants or food processing by-products) (Selvamuthukumaran & Shi, 2017). Mariod et al. (2020) compared supercritical fluid extraction (SFE) and Soxhlet extraction (SE) system and discovered oryzanol in RBO possesed a significant difference between diverse fractions of RBOs. Besides, extraction by SFE demonstrated a high impact on the sum, component, and antioxidant of lipid in RBOs. RB oil is also processed after extraction to boost its consistency and commercial value. One of the best resources of tocol and oryzanol is RBO. Tocopherols (tocopherols and tocotrienols) which are a type of vitamin E active elements, are commonly consumed in the food, cosmetics and pharmaceutical industries as plant-based ingredients (Pengkumsri et al., 2015). Table 16.1 lists the percentage of fatty acids in RBO (Fraterrigo Garofalo et al., 2020). Oleic acid, linoleic acid, and linolenic acid are the main unsaturated fatty acids, while palmitic acid, myric acid, and stearic acid are the principal saturated fatty acids. The free fatty acid value of RBO is greater than that of types vegetable oils. The most optimal saturated fatty acid for RBO:monounsaturated fatty acid:polyunsaturated fatty acid ratio is approximately 1:2.2:1.5, which is very close to the recommendations of the World Health Organization owing to its balanced fatty acid composition (Mas’ud et al., 2017). Besides being a nutritious vegetable oil, RB oil is also a rare oil including exclusive properties and health advantages. A high quality and marketability of edible RBO is typically distinguished based on its light appearance, with high levels of oryzanol and unsaturated fatty acids, as well as low levels of nontriacylglycerols.

TABLE 16.1

Fraction of fatty acids in rice bran oil.

No

Fatty acids

Percent

1.

Myristic acid C14:0

0.4
1.0

2.

Palmitic acid C16:0

17.0
21.5

3.

Stearic acid C18:0

1.0
3.0

4.

Oleic acid C18: 1

38.4
42.3

5.

Linoleic acid C18:2

33.1
37.0

6.

Linoleic acid C18:3

0.5
2.2

7.

Saturated fatty acid (SFA)

18.4
25.5

8.

Monounsaturated fatty acids (MUFA)

38.4
42.3

9.

Polyunsaturated fatty acids (PUFA)

33.6
39.2

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16.5 Bioactive phytochemicals in rice bran oil RBO comprises wax (1.5%
4%), phospholipids (0.5%
1.5%) and free fatty acids in large quantities (59.19%). It is also abundant in various compounds that are biologically active. For example, about 4% of the nonsaponified portion includes phytosterols (1.5%
2%), oryzanols (1.2%
1.8%), tocopherols, and tocotrienols (0.15%
0.2%) (Liang et al., 2014). Triterpene alcohols, other phenolic compounds, and phospholipids are other biologically active compounds obtained from the RBO. The extraction method, however, might reduce the quality of some of these micronutrients (Maurya & Kushwaha, 2018). Gama-Oryzanol or C40H58O4 is the main and unique component of RBO. It is a combination of triterpene alcohols containing ferulic acid and sterol esters. The extraction of γ-oryzanol from RB oil was initially accepted to be a single component. However, after separation using reversed-phase HPLC and determination using GC-Ms, cycloalkenyl ferulic acid, 24-methylene cyclopentyl ferulic acid and camphor ferulic acid were recognized as the main elements of γ-oryzanol (Picchio et al., 2020). Main components of oryzanols are shown in Fig. 16.3. The major phytosterols in RBO are sitosterol, campesterol, and stigmasterol (Raghav et al., 2016). The chemical structures of sitosterol and campesterol are presented in Fig. 16.4. They are known to have a variety of biologically active qualities and impact on human health. Vitamin E tocols (tocotrienol and tocopherol) are natural antioxidants that could possibly be beneficial to human health. They are lipid-soluble compounds that are randomly spread in the grain (α-tocotrienol is mainly found in the endosperm, while α-tocopherol is found in the germ). The major forms of tocotrienol are α-tocotrienol (5,7,8-trimethyltocotrienol),

(A)

(B)

(C)

FIGURE 16.3 The main components of oryzanols; cycloartenyl ferulate, 24 methylene cycloartanyl ferulate, campesteryl ferulate. (A) Cycloartenyl ferulate, (B) 24 methylene Cycloartanyl ferulate, and (C) campesteryl ferulate. Adapted from Dhankhar, P. (2014). Rice milling. IOSR Journal of Engineering, 4 (5), 34
42. https://doi.org/ 10.9790/3021-04543442.

FIGURE 16.4 Chemical structures of sitosterol and campesterol. Adapted from Raghav, P. K., Agarwal, N., & Sharma, A. (2016). Emerging health benefits of rice bran—A review. International Journal of Multidisciplinary Research and Modern Education, II (I), 367
382. ß-Sitosterol

Campesterol

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201

Chemical structures of different forms of tocotrienols and α-tocopherol. Adapted from Raghav, P. K., Agarwal, N., & Sharma, A. (2016). Emerging health benefits of rice bran—A review. International Journal of Multidisciplinary Research and Modern Education, II (I), 367
382.

FIGURE 16.5

γ-tocotrienol (7,8-dimethyltocotrienol), and δ-tocotrienol (8-methyltocotrienol), while the main structure of tocopherol are α-tocopherol (5,7,8-trimethyltocol), γ-tocopherol (7,8dimethyltocol), and δ-tocopherol (8-methyltocol) (Maurya & Kushwaha, 2018). Fig. 16.5 demonstrates the chemical structures of different forms of tocotrienols and α-tocopherol. Their biological activity produces from their capability to transfer phenolic hydrogen atoms to free radicals, consequently breach damaging sequence of reaction.

16.6 Role of bioactive components and activities Natural products obtained from plants have been consumed as a major resource of disease prevention and treatment agents for humans and animals (Sofowora et al., 2013). Nutraceuticals, such as phytochemicals, are known to have some of the significant ptentials for enhancing human well-being. Phytochemicals of both dietary and nondietary sources have recently inspired researchers’ interest due to their potential to combat a variety of diseases (Saikia & Deka, 2011). One of the plant oils is RBO, which is highly nutritious and stable (Sardarodiyan & Salehi, 2016). The important roles of RBO bioactive compounds are reviewed in the next section.

16.6.1 Antioxidant potential of rice bran oil Oxidative stress increases due to excessive production or insufficient elimination of free radicals accompanied by disease. ROS are produced by a number of mechanisms consisting of enzymatic, nonenzymatic, and mitochondrial pathways (Periyasamy, 2015). ROS able to alter nucleic acids, including 8-hydroxy-20 -deoxyguanosine (8-OhdG), further affecting their specific relation and mutational function. 8-OhdG is a responsive biomarker

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of DNA oxidative damage in the liver, kidney, pancreas, brain, and heart during oxidative stress (Liang et al., 2014). Nevertheless, ROS can be removed via critical scavenging enzymes for example glutathione peroxidase (GPx), superoxide dismutase (SOD), and catalase (CAT) (Kurutas, 2016). RBO comprises a selection of research-proven antioxidant components, for example, γ-oryzanol, tocotrienol, tocopherol, and squalene (Rahmania et al., 2020). Both tocopherol and tocotrienol, which are the natural structure of vitamin E, are considered the most important natural antioxidants. However, tocotrienols have been shown to have greater biological efficacy and biological activity than tocopherols (Maurya & Kushwaha, 2018). They function to eliminate free radicals and thus prevent from reacting with harmful biological molecules in the human body. The ferulic acid in oryzanol can inhibit ferulic acid esters, and be used as an antioxidant and “scavenger” for methyl linoleate and multiphase lipid systems (Liang et al., 2014). A number of research have also been published that RBO has higher oxidation stability than soya bean and rapeseed oils (Maszewska et al., 2018; Rahmania et al., 2020). Srivastava and Singh (2015) have shown that the thermal constancy of RBO is better than that of palm oil when both are exposed to repeated frying. The high oxidative stability of RBO indicates it suitable for fried and baking purposes (Fan et al., 2013). Research reported by Kaur et al. (2012) proves the effectiveness of RBO in baking application, where they showed that high quality cookies can be manufactured by substituting regular bakery shortening with different levels of RBO. In addition, Sharif et al. (2003) those RBO-based products have an extended shelf life as RBO is very stable and resistance to rancidity and oxidative deterioration. Several epidemiological studies also demonstrated the ability of RBO to serum cholesterol and possess few effective antioxidant properties. Supplementation of RBO to diabetic rats offered a beneficial effect through reducing oxidative stress and upregulating the total of liver antioxidant defense mechanisms (Ghatak & Panchal, 2012; Liang et al., 2014). RBO is believed to reduce the increasing frequency of 8-OHdG possibly via the mechanism of γ-tocotrienol (γ-T3) that possesses antioxidant properties. As a consequence, lipid oxidation and protein oxidative damage are prevented. By inhibiting ROS generation and scavenging ROS, Juliano et al. (2005) discovered that oryzanol from RBO can resist oxidation and inhibit the development of peroxides. RBO’s tocopherols, tocotrienols, and phytosterols all play separate roles in facilitating oryzanol oxidation. Nevertheless, although there may be a synergistic effect of these substances that promotes the antioxidant activity of RBO, the mechanism has not been completely understood (Juliano et al., 2005). The functional mechanism of RBO in the alleviation of oxidative damage is summarized in Fig. 16.6.

16.6.2 Hypercholesterolemia Despite the fact that oil contains important fatty acids and fat-soluble vitamins, several epidemiological studies have concluded that excessive utilization of edible oil can lead to non-communicable diseases. In the blood, lipids primarily consist of free total cholesterol (TC) and triglycerides (TGs). very low density lipoproteins (VLDLs), low density lipoproteins (LDLs), and high density lipoproteins (HDLs) are the major types of lipoproteins

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203

FIGURE 16.6 Antioxidant activities of rice bran oil (RBO). A responsive marker of mtDNA damage in mitochondria is 8-OHdG. The DNA chain’s eighth carbon of guanine is simply hydroxylated to 8-OHdG. In the mtDNA replication process, 8-OHdG is incorporated with adenine to form a point mutation. 8-OHdG, which functions to reduce oxidative DNA damage can be significantly reduced by RBO. Adapted from Liang, Y., Gao, Y., Lin, Q., Luo, F., Wu, W., Lu, Q., & Liu, Y. (2014). A review of the research progress on the bioactive ingredients and physiological activities of rice bran oil. European Food Research and Technology, 238 (2), 169
176. https://doi.org/10.1007/ s00217-013-2149-9.

(Langlois et al., 2020). Excessive production of VLDL or conversion of VLDL to LDL can lead to a serious medical problem, known as hyperlipidemia (Kadandale et al., 2019). This health condition is seen as a critical global concern due to its potential risk of developing heart disease, stroke and even causing death (Nelson, 2013). Therefore, it is particularly essential to combat hyperlipidemia by controlling the level of cholesterols (Adiels et al., 2008). Cheng Chia-Wen and Hsing-Hsien (2006) described that the phytosterols in RBO are closely related in structure to cholesterol, and they can prevent the cholesterol absorption in the intestine by interfering with its movement to micelles. It was also discovered that the effect of RBO sterol relative to lipoproteins is anticipated to β-sitosterol and other 4-desmethylsterols. The structure of the latter is more identical to the cholesterol compared

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to any other sterols (such as 4,40 -dimethylsterol). Hence, it can be concluded that 4-desmethylsterol portrays a greater effectiveness in reducing cholesterol absorption (Vissers et al., 2000). A research performed by Igel et al. (2003) similarly validated this hypothesis, in which they discovered that the absorption efficiency of plant sterols is inversely proportional to that of cholesterol. In comparison to cholesterol, 4-desmethylsterol does not have side chain to be substituted, so, it is easier to be absorbed than the cholesterol. Wilson et al. (2007) demonstrated that RBO oryzanol capable to decrease plasma non-HDL-C levels and thereby elevate HDL-C level by improving the emission of cholesterol and its metabolites. In another experiments by Sakamoto et al. (1987) and Seetharamaiah and Chandrasekhara (1988), it was also revealed that the administration of oryzanol in rat models significantly suppressed the upregulation of serum TC, phospholipids (PL), TG and free cholesterol. Apart from that, the cholesterol-lowering effect of RBO and the possible mechanism of its effect on the formation of aortic fat streaks (early atherosclerosis) were also studied. Findings from the study concluded that supplementation of 5%
10% (w/w) RB oil in hamsters significantly lowered the plasma total cholesterol and LDL cholesterol. The same study also reported that the excretion of neutral sterols increased significantly by 30%, indicating that lipid-lowering property of RBO was correlated with limited absorption of cholesterol in the intestine. Furthermore, the study also suggested that the reduction of fatty streak formation might be related to the nontriacylglycerol components of the oil. Another study reported by Cheng Chia-Wen and Hsing-Hsien (2006) revealed that the consumption of RBO increased the expression of LDL receptors in the liver. Reduction of LDL-C level can be done by increasing the expression of cholesterol 7-α hydroxylase (CYP7A1) and stimulating cholesterol catabolism. The expression of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase can enhance the synthesis of cholesterol, thereby balancing cholesterol in the body (Cheng Chia-Wen & Hsing-Hsien, 2006). Ausman et al. (2005) revealed that RBO could significantly reduce HMG-CoA reductase activity by 300%
500% in comparison to coconut oil. Furthermore, Minhajuddin et al. (2005) also reported that RBO tocotrienols was able to decrease the activity of HMG-CoA reductase. Mixing RBO with another edible oils can similarly show a great cholesterol-lowering effect, as demonstrated in experiments by Koba et al. (2000) and Malve et al. (2010), where they revealed that consuming RBO and safflower oil (SFO) simultaneously were more effective than taking the RBO alone. A probable explanation might be that the SFO has a special additional structure consisting of triglycerides and unsaturated fatty acids (Reena & Lokesh, 2007). In addition to the RBO
SFO combination, RBO can also be mixed with coconut oil or sesame oil to balance out the different fatty acid content. These examples of mixed oil can potentially reduce blood lipids, aside from plasma and liver lipids (Reena & Lokesh, 2007). A more detailed explanation on the mechanism of RBO in inhibiting hypercholesterolemia is summarized in Fig. 16.7.

16.6.3 Anticancer aspects Cancer is a major health issue involving men and women worldwide. Despite the fact that the current chemopreventive drugs are able to inhibit the proliferation of cancer cells,

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205

FIGURE 16.7 Hypercholesterolemia inhibition of rice bran oil (RBO). RBO can minimize the activity of HMGCoA, thus preventing cholesterol synthesis. On the other hand, it can also promote the synthesis of cholesterol by increasing the activity of CYP7A1. Increased production of cholesterol subsequently stimulates the synthesis of bile acids. Consequently, more bile acids will be excreted, and level of cholesterol in plasma will be lowered. Adapted from Liang, Y., Gao, Y., Lin, Q., Luo, F., Wu, W., Lu, Q., & Liu, Y. (2014). A review of the research progress on the bioactive ingredients and physiological activities of rice bran oil. European Food Research and Technology, 238 (2), 169
176. https://doi.org/10.1007/s00217-013-2149-9.

they can cause several drawbacks. Both in vitro and in vivo findings that proved that RBO has shown encouraging results in preventing the disease. RBO could stimulate multiple anticancer mechanism by augmenting biologically active compounds including vitamin E, γ-oryzanol, and phenolic compounds (Tan & Norhaizan, 2017). Apoptosis is a tightly controlled self-destruction mechanism that causes cells to die (Elmore, 2007). Exogenous (death receptor apoptotic pathway) and endogenous (mitochondrial apoptotic pathway) apoptosis signaling pathways can be activated depending on the source of the signaling cells involved in the process. Extracellular death signaling molecules or ligands bind to death receptors in the external pathway, triggering a series of downstream metastasis steps (Tourneur & Chiocchia, 2010). The actions begins with death ligands (i.e., Dr4/5 and TNF-) binding to related receptors on the cell membrane, followed by the recruitment of adaptor proteins like Fas-associated protein with death domain (FADD) and activation of the death-inducing signal complex (DISC) (Mongiat et al., 2007; Tabas & Ron, 2011).

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After that, the procaspase-8, which separates the DISC, is initiated, releasing the caspase-8 tetramer. Then, it continues stimulates the downstream activity of caspase-3, from caspase-cascade to cell apoptosis (Chang et al., 2003). Several apoptosis-associated gene products (proteins or enzymes) which may improve the permeability of the mitochondrial membrane following the secretion of pro-apoptotic factors may induce apoptosis. Examples of factors include cytochrome C (cyt C) and caspase-9, apoptotic peptidase activator 1 (Apaf-1), and apoptotic body development, stimulated caspase-9, and stimulated caspase-3 (Bratton & Salvesen, 2010). Kannappan et al. (2010) have revealed that γ-T3 in RBO is able to reduce tumor cell growth, particularly in human colon cancer cells by inducing TNF-related apoptosisinducing ligand (TRAIL) death receptor Dr4/5 expression. Although the stimulation possessed by γ-T3 is not specific, it has a particular effect on pancreatic, renal and blood cancer cells. The membrane-FADD complex may stimulate Dr4/5 to activate caspase-8 and caspase-3, which subsequently induce a cascading reaction and eventually promote tumor cell apoptosis. At the same time, γ-T3 can trigger mitochondria-mediated apoptosis (Sun et al., 2008). According to Zhang et al. (2012) ferulic acid (FA) can selectively induce cell apoptosis by promoting the secretion of cyt C. Furthermore, when cyt C is excreted into the cytosol, it is further binds to Apaf-1 via the WD40 domain, forming an apoptotic complex with caspase 9. The autocatalytic stimulation of caspase-9 then directs to the downstream activation of caspase-3, causing the release of pyrolytic caspase-activated DNase (CAD) (Timmer & Salvesen, 2007). CAD then migrates to the nucleus, where it triggers tumor cell apoptosis (Kunnumakkara et al., 2010; Yu et al., 2002). A study conducted by Kannappan et al. (2010), demonstrated that the γ-T3 signaling pathway, which is mediated by JAK-STAT, has a therapeutic effect on tumor cells. Apart from γ-T3, δ-tocotrienol (δ-T3) possessed as an anticancer potential to the human colorectal adenocarcinoma (DLD-1) cells in both normoxia and hypoxia. Tumor cells may produce reactive oxygen species that may destroy cell integrity. Cyclopentenyl ferulic acid is a major element of γ-oryzanol. Due to its antioxidant activity, the spread of colorectal adenocarcinoma SW480 cell line was successfully inhibited (Justo et al., 2013). Conjugated linoleic acid (CLA), a type of monounsaturated fatty acids (MUFA) which is typically found in RBO also possess antitumor effects. The role of CLA in immune response stimulation is mediated through PPAR regulation (Evans et al., 2010). Several cancer cell lines, including high-expressing lipoma, breast cancer, colon cancer, pancreatic cancer, bladder cancer, prostate cancer, and gastric cancer, contain an isomer of PPAR known as PPARγ. Evidence indicates that CLA can boost PPARγ activity by controlling PPARγ0 s N-terminal phosphorylation and inhibiting nuclear factor-κB (NF-κB) p65 activation. As a result, cell apoptosis is increased while cell proliferation is reduced. Therefore, by modifying the arachidic acid signal to control TNF-α, CLA will prevent inhibition of c-myc and induce the expression of p53 and caspase simultaneously (Evans et al., 2010). TNF-α can be used as a possible tumor therapy solution, despite the fact that the process of destroying tumor cells by TNF-α is relatively slow and the mechanism is not completely understood. The anticancer mechanism of RBO is summarized in Fig. 16.8.

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FIGURE 16.8 A probable anticancer mechanism of rice bran oil (RBO). RBO is concluded to play a role in generating antitumor activity by apoptosis via three pathways. The first pathway is through stimulation of death receptors, which then activates caspase cascade reaction and promotes the secretion of mitochondrial cytochrome C. The second pathway is by blocking JAK-STAT signal pathway through activation of SHP-1. The third pathway is through prevention of mtDNA mutation and oxidative stress caused by ROS. These pathways can result in the fundamental change of the nuclear genome, thereby cause tumor cell apoptosis. Adapted from Liang, Y., Gao, Y., Lin, Q., Luo, F., Wu, W., Lu, Q., & Liu, Y. (2014). A review of the research progress on the bioactive ingredients and physiological activities of rice bran oil. European Food Research and Technology, 238 (2), 169
176. https://doi.org/10.1007/ s00217-013-2149-9.

16.6.4 Antidiabetic properties of rice bran oil A number of experiments have been conducted to determine the antidiabetic properties of RBO. In one of the studies, intervention was done in type 1-DM rats using RBO’s tocotrienol-rich fraction (200 mg/kg body weight per day) and the rats were measured for the levels of reduced fasting blood glucose, HbA1c and serum nitric oxide (Siddiqui et al., 2010). Through the study, it was discovered that supplementation of tocotrienol-rich RBO was able to protect the kidney tissue of the experimental animals from nitrosation and oxidative damage by decreasing the level of nitric oxide in the urine and enhancing the level

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of antioxidant enzymes. Cheng Chia-Wen and Hsing-Hsien (2006) also reported the protective effect of RBO in type 2-DM rats induced by streptozotocin/nicotinamide. In another study, the supplementation of RBO (150 g RBO per kilogram of diet for 5 weeks) showed increased type 2 HDL-cholesterol, decreased excretion levels of bile acids and neutral sterols in feces, and decreased liver cholesterol, atherosclerosis index, and hyperinsulinemic response mouse. Eun Hee et al. (2007) reported the effectiveness of phenolic acid component of RB in inducing hepatic glucokinase activity and lowering the blood glucose level in C57BL/KsJ db/db mice. Meanwhile, a study by Ghatak and Panchal (2012) revealed that the intervention (11 days) of oryzanol (50
100 mg/kg body weight) extracted from crude RBO on DM rats induced by streptozotocin increased the antioxidant capacity by increasing the total of antioxidant enzymes in the liver. The diabetic rats supplemented with oryzanol in the study demonstrated a reduced level of blood glucose and a dose-dependent reduction in lipid peroxidation. In another research by Apichai et al. (2012) reported that the Thai purple glutinous RB supplement (50 g/kg; 8 weeks) effectively improved the health of streptozotocin-induced diabetic rats by reducing plasma glucose, free fatty, acid and triglyceride levels and enhancing insulin sensitivity. Posuwan et al. (2013) also validated this observation in which they reported a reduction of serum MDA levels at 12 weeks and improvement of catalase, coenzyme Q10, glutathione peroxidase in streptozotocin, superoxide dismutase and oxygen-free radical absorption capacity in diabetic rats consumed a high-fat diet with supplementation of Thai colored RB oil. Besides, the intervention of RBO effectively restored the damaged heart, kidney, liver, and pancreas of rats supplied with a high-fat diet to a normal morphology/anatomy (Posuwan et al., 2013). Thus, it can be presumed that the regulation of glycogen-regulating enzymes by RBO is one of the key mechanisms behind the antidiabetic properties of RBO. Findings from another study also observed an increase in glucokinase activity and a reduction of phosphoenolpyruvate carboxykinase and glucose-6-phosphatase activities in C57BL/6 N mice on a high-fat diet, incorporated with RBO (30% RBO supplemented for 7 weeks (Son et al., 2011). Kozuka et al. (2012) asserted that gamma oryzanol (20 or 80 μg/g body weight; intervention for 13 weeks) and brown rice (30% brown rice in the Chow diet) can improve glucose metabolism, as well as reduce the hypothalamic endoplasm stress response in a C57BL/6J mouse model on a high-fat diet. Oryzanol affects insulin secretion, blood glucose levels, glycogen regulating enzyme activity, and reduces the risk of hyperglycemia (Ghatak & Panchal, 2012). Ohara et al. (2009) revealed that oryzanol can control adiponectin excretion by preventing the activation of NF-κB. Apart from that, Wahyuni et al. (2016) demonstrated the antidiabetic property of black RB ethanol extract in Sprague Dawley rats induced by alloxan (150 mg/kg body weight). In the study, intervention of ethanol RB extract (100 or 200 mg/kg body weight) which lasted for 4 weeks, successfully showed higher hypoglycemic ability and insulin levels by regenerating pancreatic β cells in DM rats (Wahyuni et al., 2016).

16.7 Conclusion and future perspectives RB, a by-product of rice milling, is particularly loaded in oils and rich in phytochemicals. In particular, RBO comprises many fat-soluble vitamins, sitosterols, and additional

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plant sterols that provide multiple health benefits. For example, vitamin E and oryzanol in RBO have an antioxidant effect, while the fatty acid, vitamin E, sterol, and oryzanol components in RBO are good for absorption. Oryzanol, which is one of the RBO compositions, is capable of blocking the synthesis of autologous cholesterol, reducing the concentration of serum cholesterol, promoting blood circulation, regulating endocrine, and autonomous functions, as well as promoting human and animal growth and development. Collectively, RBO in general, has the ability to reduce the serum cholesterol and it has a high oxidation stability, making the storage for RBO to be convenient. Other than that, RBO is also stable and which makes it suitable to be utilized as frying oil, and to make margarine, shortening and a high-grade nutritional oil. In short, RB has been shown to have important nutritional and therapeutic values, which can eventually decrease the risk of disease and subsequently advance the quality of life. Considering the potential values of RBO to human health, it is necessary to strengthen and accelerate the development of RBO, especially by promoting continuous research on its benefits. Moreover, the current advancement of biotechnological techniques used to develop functional RBO would pave the way for the discovery of a new application of RBO. Besides, to address the significant benefits of RBO to the public, entrepreneurs should be urged to take into consideration of RBO as the main source of bioactive ingredients in superfood development. Hence, through these approaches, it is believed that the potential of functional RBO can be fully explored and utilized in the future.

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72. Available from https://doi.org/10.1038/sj.cdd.4402059. Tong, C., & Bao, J. (2018). Rice lipids and rice bran oil. In Rice: Chemistry and technology. AACCI. Published by Elsevier Inc. in cooperation with AACC International. Available from https://doi.org/10.1016/B978-0-12811508-4.00005-8. Tourneur, L., & Chiocchia, G. (2010). FADD: a regulator of life and death. Trends in Immunology Vol.31, 31(7), 260
269. Available from https://doi.org/10.1016/j.it.2010.05.005. Vissers, M. N., Zock, P. L., Meijer, G. W., & Katan, M. B. (2000). Effect of plant sterols from rice bran oil and triterpene alcohols from sheanut oil on serum lipoprotein concentrations in humans. American Journal of Clinical Nutrition, 72(6), 1510
1515. Available from https://doi.org/10.1093/ajcn/72.6.1510. Wahyuni, A. S., Munawaroh, R., & Da’i, M. (2016). Antidiabetic mechanism of ethanol extract of black rice bran on diabetic rats. National Journal of Physiology, Pharmacy and Pharmacology, 6(2), 106
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112. Available from https://doi.org/10.1016/j.jnutbio.2006.03.006. Yu, Z., Zhang, W., & Kone, B. C. (2002). Signal transducers and activators of transcription 3 (STAT3) inhibits transcription of the inducible nitric oxide synthase gene by interacting with nuclear factor κB. Biochemical Journal, 367(1), 97
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C H A P T E R

17 Different biological activities (antimicrobial, antitumoral, and antioxidant activities) of grape seed oil Isabella Rosa da Mata, Simone Morelo Dal Bosco and Juliano Garavaglia Nutrition Department, Federal University of Health Sciences of Porto Alegre (UFCSPA), Porto Alegre, Brazil

List of Abbreviations ABTS FA CIA DCV DPPH FAMEs GPSO GSPE IgG IL-6 IL-17 MGSO MUFAs MyD88 NADPH NF-κB NO OA PCR-us PPARγ PUFA RCTs

2,20 -azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) fatty acid collagen-induced arthritis coronary vascular disease 2,2-difenil-1-picril-hidrazil fatty acid methyl esters grape seed oil grape seed proanthocyanidin extract immunoglobulin G interleucine-6 interleucine-17 muscadine grape seed oil monounsaturated fatty acids myeloid differentiation protein nicotinamide adenine dinucleotide phosphate reduced nuclear factor kappa B nitric oxide osteoarthritis ultra-sensitive C-reactive protein peroxisome proliferator-activated receptor gamma polyunsaturated fatty acids randomized clinical trials

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00029-5

215

© 2022 Elsevier Inc. All rights reserved.

216 RNA SFAs TLR4 TNF-α TRF UAE

17. Different biological activities (antimicrobial, antitumoral, and antioxidant activities) of grape seed oil

ribonucleic acid saturated fatty acids toll-like receptor 4 tumor necrosis factor alpha tocotrienol rich fraction ultrasound-assisted extraction

17.1 Introduction The by-products of winemaking process, in particular grape seed, represent a promising economic source and have demonstrated a beneficial use for human health. These by-products showing a great interest, since the expansion of wine production around the world, because presents bioactive compounds very relevant to the pharmaceutical, cosmetic and food industries (Felippi et al., 2012; Garcı´a-Lomillo & Gonza´lez-Sanjose´, 2016; Glampedaki & Dutschk, 2014; Peralbo-Molina & Luque De Castro, 2013; Shinagawa et al., 2015; Tanideh et al., 2020). After winemaking process, the coproduct obtained consists mainly of grape marc, formed by films, stems, and grape seeds, the last being, in particular, reused by the industry for the production of oil and its residues for flour production (Duba & Fiori, 2015; Shinagawa et al., 2015). This reuse process helps to increase the yield and, concomitantly, to reduce the problems of waste disposal (Lutterodt et al., 2011). More attention, however, is given to grape seed oil (GPSO), which is acquired from the extraction of the seeds left over from the production of grape juice and wine. The oil extract from grape seeds showed a complex composition and heterogeneity. In general, the grape seed oil is rich in phenolic compounds, fatty acids (FAs) and vitamins, also, has been studied as a possible source of lipids, considering the various properties beneficial to human health that exhibits, namely antioxidant, antitumor, and antimicrobial action. Table 17.1 shows the composition of GPSO. This oil composed by a great variety of FAs, as well as other lipophilic composites, the phytosterols, widely reached in this oil and responsible to inhibit the liberation of different proinflammatory mediators (Garavaglia et al., 2016). Besides, the GPSO composition is dependent of several factors, such as ambient conditions, grapevine cultivars, and the maturation level of grape seeds (Fiori et al., 2014; Garavaglia et al., 2016). The oil extraction method used has a great importance to define the oil yield, as well as its composition and preservation of these bioactive components, which outlined the human health properties. Among the oil extraction techniques, cold pressing is one of the oldest techniques. This procedure is carried out without using heat or any chemical treatment, minimizing the degradation of nutritional constituents and bioactive compounds of GPSO. Using this process, the oil yield is reduced when compared to solvent extraction method and high temperatures processing; however, the solvent residues in oil are reduced, making a product safer and more desired by the consumers (Karaman et al., 2015; Lutterodt et al., 2011). The cold processing is mandatory to the organic food market, since the use of petroleum derivative solvents (such as hexane,) is restricted (Zheng et al., 2003). In this way, the application of solvent-dependent

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17.1 Introduction

TABLE 17.1 Fatty acid composition of grape (V. vinifera L.) seed oil and other fats and main phytosterol content. Fatty acids

% of total FAMEs

C6:0

nd

C8:0

0.01

C10:0

nd

C12:0

0.01

C14:0

0.05

C15:0

0.01

C16:0

6.6

C17:0

0.06

C18:0

3.5

C20:0

0.16

C22:0

nd

C16:1 (n 2 7)

0.08

C17:1 (n 2 7)

nd

C18:1cis (n 2 9)

14.3

C18:1 trans (n 2 9)

nd

C20:1 (n 2 9)

0.40

C18:2 cis (n 2 6)

74.7

C18:3 (n 2 3)

0.15

C18:3 (n
6)

nd

SFAs

10.4

MUFAs

14.8

PUFAs

74.9

n 2 3 PUFAs

0.2

n 2 6 PUFAs

74.7

Phytosterols

mg/kg/oil

Cholesterol

nd
0.10

Cholestanol

nd

Brassicasterol

0.6
0.9

2,4 methylencholesterol

nd
0.18

Campesterol

0.1
9.3 (Continued)

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17. Different biological activities (antimicrobial, antitumoral, and antioxidant activities) of grape seed oil

TABLE 17.1

(Continued)

Fatty acids

% of total FAMEs

Campestanol

nd

Stigmasterol

10.2
10.8

Δ 2 7 campesterol

0.16
0.27

Δ 2 5 2,3 stigmastadienol

nd

Clerosterol

0.90
0.94

β-sitosterol

66.6
67.4

Sitostanol

3.92
4.70

Δ 2 5 avenasterol

1.98
2.09

Δ 2 5 2,4 stigmastadienol

0.41
0.47

Δ 2 7 estigmastenol

1.99
2.30

Δ 2 7 avenasterol

0.98
1.10

FAMEs, fatty acid methyl esters; nd, not determined. From Garavaglia, J., Markoski, M. M., Oliveira, A., & Marcadenti, A. (2016). Grape seed oil compounds: biological and chemical actions for health. Nutrition and Metabolic Insights, 9, 59
64. https://doi.org/ 10.4137/NMI.S32910.

methods required an adequate system to residue disposal and by-products management by the industries, to diminish the ambient impact (Karaman et al., 2015). An alternative process used to oil extraction from grape seeds is the ultrasoundassisted extraction (UAE), mainly due its potential application to food and pharmaceutical industries (Bo¨ger et al., 2018; Vilkhu et al., 2008). The main advantages of this extraction technique are the increasing of oil yield and reducing temperature and time to extraction, providing a reduced thermic degradation and higher preservation of structural and molecular proprieties of oil bioactive compounds (Bo¨ger et al., 2018; Tian et al., 2013). In order to obtain a higher yield in the process and to minimize the free radical content in the oil, the study conducted by Bo¨ger et al. (2018) optimized the UAE for GPSO. Comparing to the control process, an increase of 12% in the extraction process was observed, leading to the conclusion that the use of UAE can be advantageous, since there is greater productivity of oil extraction, in a shorter process time, in addition to the need to use less solvent, thus maintaining the quality of the extracted oil. The application of UAE increases the potential for recovery and reuse of by-products, which is based on its chemical, functional, and antimicrobial properties, and in view of this, improving the GPSO quality and purity (Karaman et al., 2015). This chapter aims to examine the main studies and their respective findings, developed on the use of GPSO, highlighting the benefits that different biological activities (antimicrobial, antitumor, and antioxidant) present and enable human health. Fig. 17.1 summarizes the main activities of GPSO.

Multiple Biological Activities of Unconventional Seed Oils

17.2 Antioxidant and antiinflammatory activity

219

FIGURE 17.1 Different polyphenols and main biological activities identified in grape seeds.

17.2 Antioxidant and antiinflammatory activity The grape seed is a residue of winemaking process characterized by a great number of compounds with high antioxidant activity (Benbouguerra et al., 2020; Peralbo-Molina & Luque De Castro, 2013; Shinagawa et al., 2015). From the dried grape marcs, 38%
52% of weight is represented by the seeds and this content is possibly produced 10%
15% of oil with a considered nutritional value (De Souza et al., 2020). The GPSO contains high level of polyunsaturated fatty acids (PUFAs), varied from 85% to 90% (Bail et al., 2008; Garavaglia et al., 2016; Maier et al., 2009; Shinagawa et al., 2015). From the PUFAs of oil, the linoleic acid makes up 58%
78% of the FA content and is responsible for the biological actions of the seed extract, being associated with the prevention and treatment of cardiovascular diseases, since it performs the control plasma lipid profile (Bail et al., 2008; Kim et al., 2010; Shinagawa et al., 2015). Even, the GPSO has natural antioxidant molecules, such as phenolic compounds (flavonols, flavans, anthocyanins, and stilbenes, mainly resveratrol) and vitamin E (tocopherols and tocotrienols), which contribute to the protection against free radical damages (Bo¨ger et al., 2018; Wen et al., 2016). Vitamin E, ranging from 1.0 to 53.0 mg per 100 g of oil (Garavaglia et al., 2016; Shinagawa et al., 2015), is directly related to the antioxidant activity of seeds extract and oil (Bail et al., 2008), besides antitumoral and neuroprotector properties (Bail et al., 2008; Fernandes et al., 2013). The content of vitamin E of GPSO has been reported to show a highest variability between grapevine cultivar and environmental conditions of cultivation (Garavaglia et al., 2016). A study conducted by Fernandes et al. (2013) characterized the oil extracted from seeds of 10 different grape varieties in relation to the FA and vitamin E contents, thus analyzing their antioxidant activity. The findings of this study showed a great prevalence of linoleic acid on oil composition (ranging 63%
73.1%), followed by oleic acid (C18:1), palmitic acid (C16:0), and stearic acid (C18:0). Regarding vitamin E, seven compounds were determined in the GPSO: α-, γ-, δ-, tocopherols and α-, β-, γ-, δ-, tocotrienols and all seed oils showed more tocotrienol than tocopherol compounds. The total content of tocotrienols and tocopherols ranging from 749 to 2192 mg/kg oil. In the study, the GPSOs of 10 varieties studied exhibited an excellent source of vitamin E (148
358 α-tocopherol equivalents), in addition to the vitamin bringing several health benefits, acting as a powerful fat-soluble antioxidant and preventing

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17. Different biological activities (antimicrobial, antitumoral, and antioxidant activities) of grape seed oil

premature aging, as well as the appearance of certain chronic diseases [such as coronary vascular disease (CVD)]. In order to characterize the antioxidant potential of oils, radical scavenging activities were measured by 2,2-difenil-1-picril-hidrazil and 2,20 -azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) methods, resulting in a variable radical scavenging activity, from 38.68% to 69.89%. To determine and evaluate the potential of phenolic compounds, a systematic review with metaanalysis was realized by Haghighatdoost et al. (2020). These authors demonstrated the effect of different phenolic compounds of grapes and its seeds on inflammatory mediators (IL-6, TNF-α, and PCR-us), considering that chronically increased inflammation is a risk factor for negative outcomes, such as the development of chronic diseases. Phenolic compounds from grape seeds have a great importance, mainly resveratrol, because they would reduce the inflammation by NO inhibition and antioxidant enzymes. Furthermore, the phenolic compounds from grape seeds extracts can be more effective to reduce PCR-us than any other grape fractions. In addition, doses greater than 200 mg per day showed a tendency to reduce serum concentrations of PCR-us. It is suggested that phenolics have more bioavailability and provide more beneficial metabolites. Finally, the study mentions the importance and the need to carry out randomized clinical trials with a longer treatment period, grape polyphenols from different sources, and a larger sample size. Tanideh et al. (2020) conducted a study to determine the effects of GPSO treatment on the prevention of knee osteoarthritis (OA) in male Sprague-Dawley rats. The oligomeric proanthocyanidins and catechins from grape seed are recognized molecules with antiinflammatory potential and factors necessary to control the development of OA. The GPSO, both in its intraarticular injectable form and in its orally administered form, had preventive effects for the development of OA. These beneficial effects corroborate with previous findings in the literature, such as that seen in the study conducted by Kim et al. (2018), which verified the influence of grape seed proanthocyanidin extract (GSPE) on signaling pathway mediated by TLR4 (receptor responsible for contributing to the induction of proinflammatory cytokines) in the regulation of arthritis autoimmune in a mouse model with collagen-induced arthritis. The GSPE is a standardized water-ethanol extract derived from red grape seeds, in which several antioxidants, including catechins and oligomeric proanthocyanidins, are concentrated. In this way, a reduction in serum levels of immunoglobulin G (IgG) and proinflammatory cytokines (TNF-α, IL-6, and IL-17) was observed in the mice treated with GSPE. Moreover, the administration of extract also reduced the expression of TLR4 and can attenuate autoimmune arthritis by regulating the TLR4, MyD88, and NF-κB signaling pathway. Furthermore, the extract effectively suppressed collagen type IIIgG and proinflammatory cytokines. Finally, the proanthocyanidin extract of grape seed can be effective on immunological diseases treatment, such as rheumatoid arthritis.

17.3 Antitumoral activity The diet would influence on chronic diseases, including cancer, diabetes, cardiovascular diseases, among others. Due to the association attributed to natural antioxidants of foods (such as vitamin E, polyphenols, and flavonoids) in preventing free radical damage, research with the wine industry by-product has gradually gained more prominence (Averilla et al., 2019; Choi & Lee, 2009).

Multiple Biological Activities of Unconventional Seed Oils

17.3 Antitumoral activity

221

The vitamin E, represented in GPSO by alfa (α-), beta (β-), gamma (γ-), delta (δ-) tocopherols and tocotrienols, provides important health benefits (Choi & Lee, 2009; Fernandes et al., 2013). Tocopherols and tocotrienols are molecules with widely varying degrees of biological activities. Choi and Lee (2009) evaluated the antioxidant and antiproliferative fraction rich in tocotrienol (TRF) from GPSO using tumoral human cells MCF7 (breast cancer), NCIH460 (lung cancer), HCT116 (colon cancer), and MKN45 (stomach cancer). As main results, the efficacy of TRF on neutralization of lipid peroxyl radicals (or lipoperoxide) and metal chelation prooxidants was confirmed. These properties of tocotrienols were related with the presence of an unsaturated side chain, which would facilitate the incorporation of this molecules into the cells and increasing the efficiency of radical recycling. Similarly, it was also observed that α-tocopherol has greater free radical scavenging activity than TRF, as for on antiproliferative effects of TRF on breast, lung, colon, and stomach cancer cells, these were quantified in terms of percentage of cytotoxicity; as a result, TRF showed greater cytotoxicity at a concentration of 1 mg/mL against breast cancer cells (81%) and lung cells (76%), while it had less antiproliferative activity against colon cancer cells (17%) and gastric cells (47%). The study mentioned the importance of tocotrienols, for preventing the formation of new blood vessels, thus preventing the growth and proliferation of cancer, and for inducing the apoptosis of cancer cells. In order to investigate the nutraceutical potential of grapevines, Xia et al. (2018) carried out a study to evaluate the total phenolic content, phenolic composition, antioxidant, and antiproliferative activities in vitro of seeds and skins of 31 different grape cultivars. According to their obtained data, the antiproliferative activity of grape seed extracts was very similar to that of the extracts of grape peels against human hepatocellular carcinoma cells (HepG2). In this way, was verified a positive correlation of phenolic and flavonoid compounds with greater antioxidant and antiproliferative activities. Moreover, this effect of phenolic compounds and its biological functions are dependent of consumed quantity in diet and bioavailability of extracts, being a limiting factor to potential application of hydrophilic polyphenols as therapeutic agents (Lei et al., 2020; Wang et al., 2016). Nevertheless, the grape seed extract showed a good solubility in aqueous medium; this hydrophilic characteristic can reduce the applications in lipophilic systems (fats, oils, and biological models), which make it unable to pass through the lipid bilayer membranes and, consequently, impairing its bioavailability (Lei et al., 2020). To improve the lipophilic properties of grape seeds extract disctinct process can be applied. For example the molecular hybridization techniques, which modify the molecules structure by bioactive compounds fractions combination to generate hybrid components with improved effectiveness and increased the biological affinity for specific targets (Lei et al., 2020; Liang et al., 2017; Wang et al., 2016). Through this process, a new and more efficient derivative of lipophilic grape seed extract can be obtained and used in the treatment of cancer (Lei et al., 2020; Liang et al., 2017). The phenolic compounds of grape seed extracts and GPSO can be used in a pure and isolated form, a modification as a hybridization technique, can be applied. Using hybrids with decanoic acid that exhibited higher lipophilicity, derivatives are effective lipophilic antioxidants and show the potential as adjuvant therapy for cancer, inducing cell cycle arrest in G1 phase and apoptosis (Lei et al., 2020). Regarding the GPSO, no modifications are necessary to improve its lipophilicity, representing an advantage in its application in biological models.

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17. Different biological activities (antimicrobial, antitumoral, and antioxidant activities) of grape seed oil

However, as the amount of phenolic compounds in the GPSO is reduced, enrichment processes or supplementation with isolated molecules can be applied in the oil, or else, the use of seeds from grapevines rich in polyphenols can be used. Against different cancers, GPSO has been evaluated as a nanocarrier, since the development of nanodosage forms of phytochemicals may represent a significant progress in counteracting free radicals and combating certain tumor cells lines (Garavaglia et al., 2016). Other compounds that exhibited great potential on prevention of different human cancer are the proanthocyanidins from grape and GPSO (Albogami, 2020; Kaur, Agarwal, & Agarwal, 2009; Lin et al., 2020). Besides, the mechanism of proanthocyanidins proliferation inhibition, in cellular and molecular levels, of different cancer types is not totally elucidated. The proanthocyanidin purified fractions inhibited the viability of human colorectal adenocarcinoma (HT29), human breast carcinoma (MCF-7), and human prostate adenocarcinoma (PC-3) cells and the action was dependent of exposition time and proanthocyanidin concentration (Albogami, 2020). There are two ways for proanthocyanidins to inhibit cancer cells, first by a way dependent of caspase and an independent of caspase and positively BAX in cancer cells, consequently inducing nuclear apoptosis (Albogami, 2020). Finally, in addition to inhibiting the viability of cancer cells and reducing proliferation, proanthocyanidins reduced the migration of cancer cells and can therefore be considered a potential chemotherapeutic and chemopreventive agent (Lei et al., 2020). A challenge is encountered during the treatment of different types of cancers, which is the multidrug resistance to the main classes of cytotoxic drugs. In view of this, studies were started in order to find mechanisms and agents that help the reversing of this situation. Treatment with proanthocyanidins reversed the multiresistance HL-60 and ADR cell lines (which overexpress MDR1, MRP1, and LRP), as it negatively regulated the expression of MRP1, MDR1, and LRP, inducing the apoptosis of HL-60 and ADR cells (Lin et al. 2020). In this way, the proanthocyanidins of GPSO would prevent the development of tumoral cells, thus inducing apoptosis and decreasing the cells proliferation by inducing cell cycle arrest. Numerous in vitro and in vivo evidences suggested these anticancer effects of GPSO (Albogami, 2020; Averilla et al., 2019; Choi & Lee, 2009; Garavaglia et al., 2016; Kaur et al., 2009; Lei et al., 2020).

17.4 Antimicrobial activity Nowadays, different industries (mainly pharmaceutical and medical) showed a great interest in the development of products that restrict the growth of pathogenic bacteria species resistant to antibiotics and toxin-producing fungi, due to the fact that, they condition the misdirection treatment of several diseases (Yadav et al., 2015). With the increase of grape and wine production and the application of by-products rich in phenolic compounds, as well as the GPSO, the evidence and relevance, regarding the biological properties of these compounds (antioxidant, antimicrobial, antiinflammatory action, among others) required to be verified (Leal et al., 2020). GPSO has a toxicity effect on some pathogens, suggesting an antimicrobial feature, displayed by phenolic compounds, such as resveratrol, and involves the induction of oxidative damage to bacterial membrane (Baydar et al., 2006; Garavaglia et al., 2016; Rotava

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17.4 Antimicrobial activity

223

et al., 2009). The phenolic compounds reached in GPSO, for example, can affect the bacteria metabolism and growth, which is related to its capacity of stimulating or inhibiting the microbial growth, according its cultures medium concentration and molecular structure (Leal et al., 2020; Vaquero et al., 2007). The composition of different phenolics in grape and GPSO (catechin, proanthocyanidin, quercetin, phenolic acids, resveratrol, and other molecules) is dependent of a great number of factors, including grapevines and the winemaking process (Averilla et al., 2019; Vaquero et al., 2007). Besides, the phenolic composition complexity and different classes of compounds (flavonoids, stilbenes, phenolic acids, tannins) of grape seeds can interfere on antimicrobial activity of seed extracts and GPSO (Garcı´a-Lomillo & Gonza´lez-Sanjose´, 2016; Singleton, 1992; Vaquero et al., 2007). In an experimental study carried by Vaquero et al. (2007), the antimicrobial properties of phenolic compounds from different Argentine grapevines against common food pathogens (Serratia marcescens, Proteus mirabilis, Escherichia coli, Klebsiella pneumoniae, Flavobacterium sp.) were investigated. They reported that grape seed extracts showed high levels of phenolic compounds, which inhibited bacterial development and thus confirming their potential for antimicrobial action. Also, the inhibitory effect of phenolic compounds can be justified by adsorption to cell membranes, interaction with enzymes, substrate, and deprivation of metal ions. In study conducted by Leal et al. (2020), the phytochemistry profile of different Portuguese grapevines was evaluated, as well as their antioxidant and antimicrobial activities (disk diffusion method) against human gastrointestinal pathogenic bacteria (Gram-positive bacterial isolates of Staphylococcus aureus and Enterococcus faecalis, and Gram-negative isolates of E. coli and K. pneumoniae). The potential antimicrobial action was observed against Gram-positive bacteria. Al-Mousawi et al. (2020) also evaluated the antibacterial action of seed extracts from red grapes to avoid the biofilm formation by S. aureus and Staphylococcus haemolyticus and as the grape seed extracts have a great concentration of phenolic compounds, the formation of biofilms by these two bacteria species was inhibited. As suggested, the phenolics of grapes seeds inhibited the synthesis of bacteria cell wall by suppressing the gene expression of cytoskeletal proteins which bind to the 30S subunit of the bacterial ribosome, preventing the binding of the transfer ribonucleic acid (tRNA) to the ribosome complex and, consequently, inhibiting bacterial protein synthesis. Another potential action of GPSO and other grape fractions from V. vinifera L. matrices is the antifungal activity (Fraternale et al., 2015). Because a reduced number of drugs against fungal diseases available on market, as well as the increasing resistance to these drugs, studies in this area were developed by Simonetti, Brasili, and Pasqua (2020), and Gintjee, Donnelley, and Thompson (2020). Simonetti, Brasili, and Pasqua (2020) were realized a review to examine the extraction method, chemical characterization, and antifungal activity of phenolic compounds from V. vinifera grapes against human pathogens. As reported, the seed extracts were rich in phenolic and polyphenolic compounds and would be useful and promising as functional ingredients, for use in formulations against various pathogenic fungi and, equally, for the development of new antifungals drugs. Thus, these observations, primarily based on in vitro studies, in which different cells are incubated with GPSO and tested for different properties, have been showed a potential application as an antimicrobial product. Also, the data analyzed demonstrate that the clinical and preclinical tests with GPSO can be extended to exploring its potential therapeutic use.

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17. Different biological activities (antimicrobial, antitumoral, and antioxidant activities) of grape seed oil

17.5 Other potential biological activities of grape seed oil Regarding the biological effects displayed by the GPSO and grape seeds extract, a great number of activities can be attributed, as described previously. Moreover, the complexity and variability of GPSO composition and a great number of different compounds can be reached, and, extended our potential use in distinct industries and sector, as pharmaceuticals, medical, agriculture, nutraceutical and food industries. For example in food industry, cold pressed GPSO stands out as a suitable alternative to other vegetable oils, because has a higher amounts of essential FA and others bioactive compounds is an environmentally friendly oil obtained as a by-product from wine and grape juice-making processes (Shinagawa et al., 2015). Martin et al. (2020) outlined the potential use of GPSO as a functional food and highlight that food and nonfood industries are becoming novel targets of oil obtained from grape seeds given its various properties. In addition to the activities already presented previously, other nutraceutical benefits can be attributed to the use of GPSO. A study conducted by Zhao et al. (2015)evaluated the antiadipogenic and antiinflammatory potential of muscadine GPSO (MGSO) using TRF and primary human stem cells derived from adipose (hASCs); it was observed that MGSO is a wide source of tocotrienols (40.7
68.9 mg of γ-tocotrienol per 100 g of oil and 30.1
48.1 mg of α-tocotrienol per 100 g of oil). In addition, the study also demonstrated the oil’s potential to attenuate the formation of new fat cells and adipose inflammation, since MGSO was able to reduce the expression of PPARγ and CEBPα mRNA (main transcription factors of adipogenesis). Other studies also suggest the potential for using grape seed extract to improve conditions associated with metabolic syndrome (Martin et al., 2020; Rameshrad et al., 2019).

17.6 Conclusions The GPSO, as well as the other by-products of winemaking industry, must be seen as potential alternatives for functional complementary therapy. Some investigations outlined to discover the relevance and composition of grape seeds oil and by-products demonstrated the great complexity and variability in the composition of phenolic compounds, FAs, phytosterols, and vitamins. In general, GPSO is composed of different chemical compounds, which has an important influence of grapevines and grapevines culture conditions (geographical area, soil, climate conditions, conduction systems and another cultural traits), the oil extraction methods adopted, storage conditions. These conditions directly affect the final quantification of oil compounds (mainly phenolic compounds) and, therefore, define the degree and potential nutrients action. Finally, given that the bioactive components of the GPSO are strongly correlated with a broad spectrum of beneficial effects (antioxidant, cardioprotective, antitumor, antiinflammatory, antimicrobial, and other health-promoting properties), further research and knowledge about the mechanisms that conditions to such properties should be encouraged, and thus, consequently, the application of these functional compounds as adjuvant agents in the treatment of illnesses is enhanced.

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C H A P T E R

18 Citrus seeds fixed oil, composition and its biological activities Rasheeda Hamid Abdalla Ahmed1 and Abdalbasit Adam Mariod2,3 1

Tuberculosis Reference Laboratory, National Public Health Laboratory, Ministry of Health, Khartoum, Sudan 2Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 3College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia

18.1 Introduction The origin of the different types of citrus is not completely known. But it can be said that citrus is a fruit of the old world, and it is believed that the original home of citrus is the tropical regions of Southeast Asia, India, Burma, and Western India. It is cultivated in many countries of the world, the most important of which are the United States of America, Spain, Brazil, Italy, Egypt, and Morocco. Citrus species belong to the Aurantioidea of the family Rutaceae and include about 1,600 species. These fruits are not only being expansively produced for natural consumption but are also extensively processed for their natural juices and extracts for manufacturing industries such as marmalade in canning industries and flavonoids and essential oils in chemical Industries. Citrus are also processed to use in perfumes, beverage industries, for their aromas, flavors, cosmetic, and medicinal uses8. Despite being one of the most important crops produced in the world, only about 18% of the citrus fruit is used, while 50%
70% of the raw fruits, consisting of peels, seeds (Fig. 18.1), and pulp, is considered waste by-product. The health benefits of citrus wastes (by-products) stem from their bioactive compounds. These said bioactive compounds have the ability to perform a variety of beneficial biological functions such as improving body functionality or preventing diseases by the action of stimulating the immune system, reducing platelet aggregation, and contain antioxidant, antibacterial, and antiviral activities to name a few (El-Adawy et al., 1999; Herna´ndez-Montoya et al., 2009; Schmidt & Pokorny´, 2005).

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FIGURE 18.1

Different citrus seeds.

18.2 What are fixed oils? Fixed oils are compounds with a fixed chemical composition that do not volatilize at room temperature and do not volatilize with water vapor and consist of a group of unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid, and other fatty acids. These oils are found in the seeds of many types of plants such as castor, jojoba, flax, sesame, watercress, olive, sunflower, corn, and citrus seeds. These oils are obtained in two main ways either using organic solvents or by hydraulic pressing (cold press) (Smith et al., 2009).

18.3 Composition of citrus seeds fixed oil Citrus seeds contain an astounding 26%
42% oil. They are a good source for many nutrients such as K, Mg, Na, Ca, and Fe, and their extracted oils are rich in phytochemicals, lipids, fiber concentrates, and essential fatty acids, having the ability to be efficiently used as food supplements or drugs, respectively. Citrus seed oil contains saturated and unsaturated acids with phospholipid levels range of 491
590 mg/100 g. Among the phytosterols, sitosterol is the predominant phytosterol. Many phytochemicals are found in oil seeds like the lipid-soluble tocopherols, carotenoids, and phenolic and polyphenolic compounds. Unsaturated fatty acids, such as alpha-linolenic acid, can also be detected in a variety of seed oils along with other important oil properties such as antioxidant activity and oil stability. Citrus seeds have also been found to be a rich source of vitamin C, folic acid, foliate, as well as thiamin, niacin, and vitamin B6 all contributing to the seeds’ immense potential to provide significant health benefits by efficiently extracting and utilizing these vitamins for pharmaceutical use (Adeyeye & Adesina, 2015). Many oils from the seeds of different types of fruits, including citrus, have medicinal value and are also used in the manufacture of confectionery, toiletry, and perfume. The economic, medical, and nutritional values of citrus seed oil were studied, and it was found that there are clear differences in the fatty acid content of seed oil of different types of

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citrus fruits. Several studies have measured the oil content in citrus seeds from different countries. The percentage of oil in Tunisian citrus seeds was 26.1%
36.1%, in Brazilian lemon seed oil it was 32.0%
38.3%, and in Egyptian citrus seed oil it was 40.2%
45.5%. The proportion of Pakistani citrus seed oil was 27.0%
36.5% (Anwar et al., 2008; Habib et al., 1986; Reda et al., 2005; Saı¨dani et al., 2004).

18.4 Biological activities of citrus fixed seed oil 18.4.1 Antioxidant activity The antioxidant activity of bitter orange and mandarin seed oils was studied using 1diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and bleaching test of B-carotene, and it was compared with ascorbic acid and butylated hydroxytoluene (BHT) as wellknown antioxidants. The results showed that ascorbic acid inhibits 80% of DPPH radicals. While bitter orange seed oil inhibited 84.5% at D2 and Mandarin resulted inhibited 79.9% of D2-marked DPPH radical removal activity, with an efficacy similar to that of reference ascorbic acid (80%). This result showed that bitter orange and mandarin seeds clean the radicals of DPPH better than the oilseeds of Opuntia dillenii (11.43%) (Tounsi et al., 2011). An in-depth study was conducted on the antioxidant compounds and antioxidant activities of the Oroblanco and pummelo
grapefruit hybrids (Fig. 18.2) and it was compared with the white grapefruit. Total and free phenols and phenolic acids were determined. Antioxidant activities were estimated with two free radicals [2,20 -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS)] and nitric oxide (NO). The free radical scavenging properties of hybrids and grapefruit were also evaluated by bleaching (β-carotene). The results showed that both fruits differed in their ability to quench these radicals, and the hybrids showed more antioxidant activity than white grapefruit. The study also showed that grapefruit contains caffeic, β-coumaric, ferulic, and sinapic, which were found in greater proportion than in hybrids. Both fruits contain high concentrations of natural antioxidants with antioxidant activities. The phenol content and antioxidant capacity are much higher in hybrids than in white grapefruit. The higher antioxidant capacity of hybrids makes these new types of citrus fruits highly nutritious (Gorinstein et al., 2004). Guneser and Yilmaz (2017) studied the active, aromatic, volatile, and biologically active compounds in addition to knowing the organoleptic properties of lemon seed oils for the possibility of creating new applications for this oil. The research team also compared the extraction method by cold pressing and hexane extraction. The study quantified catechin, eriocitrin, rutin, naringin, naringenin, hesperidin, neohesperidin, and kaempferol as flavonoids, ferulic, rosmaneric, and tr-2-hydrocinnamic as phenolic acids in these oils. Both naringenin and gallic acids were significantly higher in the cold-pressed sample. Lemon seed oil has been noted to be highly aromatic, mostly featuring citrusy qualities (Guneser & Yilmaz, 2017). The scientist Inan and his research group studied the effect of the location and type of citrus on the activity of phenols and antioxidants and the characteristic of the root scavenging of some Turkish citrus seeds and oils. By determining the total phenolic content, antioxidant activity, and root scavenging effect of seeds and seed oils for samples of

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FIGURE 18.2

Grape fruit seed oil.

tangerine, orange, and lemon collected from different regions in Turkey, the results ˙ showed that lower parameter levels were obtained in citrus seed oils than seeds (Inan et al., 2018). Recently, interest has increased in vegetable oils extracted from fruit seeds, which are originally a by-product during manufacturing processes. A group of scientists characterize the oils extracted from citrus seeds of Hamlin, Natal, Beira Rio, and Valencia orange (Citrus sinensis); they intend to know the amounts of total carotenoids and total phenolic compounds. Their results showed that orange seed oils can be used as specialized oils in the diet, as they contain large amounts of bioactive compounds and antioxidants. The results of the study showed that citrus oils have the ability to scavenge free radicals. And the oxidative oxidation efficiency of the analyzed oils followed a descending order: Pera-rio . Hamlin 5 Natal . Valencia. These results clearly show that there is a real value to the orange product industry waste, which increases the viable sources for obtaining specialized oils (Jorge et al., 2016).

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18.4.2 Different biological activities Citrus seeds are highly enriched with a lots of nutritional and health benefits. They can actually help prevent and cure some diseases. Citrus extracts have potential antioxidant, antiviral, antimicrobial, antiinflammatory, and anticancer activities, effects on capillarity, and cholesterol-lowering ability. In addition, some studies have also shown citrus seed extracts to contain hematological effects, cytotoxic and chemopreventive effects, hepatopreventive effects, and can even be beneficial in combating Covid-19 disease and Dengue fever. Citrus paradisi showed antibactericidal effect on Lactococcus lactis subsp. lactis with a dose low enough to be used as bio-preservative in food where this microorganism causes spoilage. It is likely that it will prove more difficult for bacteria to develop resistance to the multicomponent oils than to common antibiotics or to the generally single molecular-entitled chemical preservatives (Anwar et al., 2008). Adeneye (2008) evaluates the hematinic property of methanol seed extract of C. paradisi Macfad. This affect can be identified by chronic administration at the oral dose of 100
600 mg/kg/day of the extract on the hematological parameters in normal young adult female Wistar rats. Elevated level of total leukocyte count, lymphocyte differentials (Lymph.), red blood count, hemoglobin concentration (Hb), packed cell count (PCV), mean corpuscular volume, mean corpuscular hemoglobin (MCH), MCH concentration, and platelet count (PL) were resulting from the 30 days of oral administration with graded doses. The study concluded that the extract may account for the significant improvement in the hematological factors due to the presence of two vitamins. The study demonstrated that the methanol extract of C. paradisi Macfad can be used in the treatment of blood deficiency (Adeneye, 2008). Citrus seeds contain bioflavonoids with the bioactivities on apoptosis induction in human hepatocellular cancer cells. Neohesperidine, hespiridine, and naringin are active flavonone glycosides. Hesperidin can induce cell death in hepatic cancer cells. The HepG2 cell death was apoptosis in a dose-response manner because of externalization of phosphatidylserine without propidium iodide staining to the DNA, which was detected by annexin V-FITC/PI and flow cytometry. This cell apoptosis can be performed via mitochondrial and death receptor pathways. The HepG2 cells treated by hesperidin loss mitochondrial transmembrane potential. Caspase-9, -8, and -3 activities were activated and increased in HepG2 cell treated by hesperidin. Flavonoids from citrus seeds are beneficial and can be developed as anticancer drug or food supplement. Hesperidin from citrus seed induces human hepatocellular carcinoma HepG2 cell apoptosis via both mitochondrial and death receptor pathways (Banjerdpongchai et al., 2016). Bioactive compounds from citrus, such as limonoids, flavonoids (naringin), and carotenoids (lycopene, lutein), were determined to suppress the growth rate of human breast cancer. Bioactive components in lemon seed extracts could be a good source of antioxidants and induce apoptosis in MCF-7 breast cancer cells (Jinhee et al., 2011). The alcoholic extract of lemon seed and its ethyl acetate fraction (12
25) showed antifertility effect in female albino mice through its antizygotic action. Complete restoration of fertility was resulted from withdrawal of test drug (Kulkarni et al., 2005). Citrus seeds contain different compounds with varied levels of bitterness. These compounds have been tested against insects and proved to be effective. In laboratory, different citrus seed extracts were tested against Aedes albopictus larvae. These

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extracts provided satisfactory result. Ten varieties of citrus extracts carried out to test against the fourth instar larvae of dengue fever mosquito, A. albopictus. The extracts from Citrus jambhiri and Citrus limon were more effective as larvicides with lowest LC50 (119.993 and 137.258 ppm, respectively, after 24 hours of exposure and 108.85 and 119.853 ppm, respectively, after 48 hours of exposure) and LT50 values (2.51 and 4.91 hours, respectively) and highest percent mortalities (95.6% and 88.9%, respectively), after 24 hours of exposure. The results indicate that C. jambhiri and C. limon being the most effective in terms of LC50, LT50, and percent mortalities. Citrus seed extracts are environment friendly and can be used for managing A. albopictus larvae (Bilal et al., 2017). A relationship of citrus hesperidin and COVID-19 disease was recently reported; it is found to be based on the performance of hesperidin and its interaction to receptors SARS-CoV-2 main protease (PDB:6Y84) and crystal structure main protease (PDB:6LU7), Spike glycoprotein-RBD (PDB:6LXT), and PD-ACE2 (PDB:6VW1), which could have an inhibitory effect against virus infection and replication. Since hesperidin is abundant in citrus peel, several studies presented citrus waste as a good option to obtain this compound from a natural source. Based on the interactions with receptors of SARS-CoV-2, clinical trials should be carried out with this product to establish its prophylactic or therapeutic activity against COVID-19.

18.5 Conclusion It is no surprise that waste management has grown more important and necessary in the past decades, with increase in industrial scale productions due to the rise in population all over the world. Citrus fruits, despite being one of the most important crops grown and processed worldwide, had only 18% of the fruit utilized while 50%
70% of the raw fruit was being disposed of. When the use of these residues was looked into, it was found that citrus residues could be utilized for oil production.

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1299. ˙ ¨ ., O ¨ zcan, M. M., & Aljuhaimi, F. (2018). Effect of location and Citrus species on total phenolic, antioxidant, and Inan, O radical scavenging activities of some Citrus seed and oils. Journal of Food Processing and Preservation, 42(3), e13555. Jinhee, K., Jayaprakasha, G. K., Uckoo, R., & Patil, B. S. (2011). Evaluation of chemopreventive and cytotoxic effect of lemon seed extracts on human breast cancer (MCF-7) cells. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 50(2), 423
430. Jorge, N., da Silva, A. C., & Aranha, C. P. M. (2016). Antioxidant activity of oils extracted from orange (Citrus sinensis) seeds. Anais da Academia Brasileira de Cieˆncias, 88(2), 951
958. Kulkarni, T. R., Kothekar, M. A., & Mateenuddin, M. (2005). Study of anti-fertility effect of lemon seeds (Citrus limonum) in female albino mice. Indian Journal of Physiology and Pharmacology, 49(3), 305
312. Reda, S. Y., Leal, E. S., & Batista, E. A. C. (2005). Characterization of Rangpur lime (Citrus limonia Osbeck) and “sicilian” lemon (Citrus limon) seed oils, an agro-industrial waste. Cieˆncia e Tecnologia de Alimentos, 25(4), 672
676. Saı¨dani, M., Dhifi, W., & Marzouk, B. (2004). Lipid evaluation of some Tunisian citrus seeds. Journal of Food Lipids, 11(3), 242
250. Schmidt, S., & Pokorny´, J. (2005). Potential application of oil seeds as sources of antioxidants for food lipids
A review. Czech Journal of Food Sciences, 23, 93
102. Smith, J., Garcia-Perez, M., & Das, K. C. (2009). Producing fuel and specialty chemicals from the slow pyrolysis of poultry DAF skimmings. Journal of Analytical and Applied Pyrolysis, 86(1), 115
121. Tounsi, M. S., Moulehi, I., Ouerghemmi, I., Mejri, H., Wannes, W. A., Hamdaoui, G., Limam, F., & Marzouk, B. (2011). Changes in lipid composition and antioxidant capacity of bitter orange (Citrus aurantium. L) and mandarin (Citrus reticulata. Blanco) oilseeds on different stages of maturity. Journal of the American Oil Chemists’ Society, 88, 961
966.

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C H A P T E R

19 Biological activities of tea seed (Camellia oleifera Abel.) oil Fong Fong Liew1, Kim Wei Chan2 and Der Jiun Ooi1 1

Department of Oral Biology and Biomedical Sciences, Faculty of Dentistry, MAHSA University, Jenjarom, Selangor, Malaysia 2Laboratory of Natural Medicines and Products Research, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Malaysia

19.1 Introduction Being a genus of evergreen flowering plants in the Theaceae family, Camellia comprises more than 200 described species. While most species are valued for their ornamental appeal, selected species are of great economic importance as they are the raw materials for beverages and edible oils (WFO, 2021). Among others, Camellia sinensis is commercially grown for the manufacturing of green, white, and black tea products following different degrees of fermentation using the leaves and buds. Camellia oleifera, on the other hand, is mainly cultivated as a promising source of edible oil made by pressing the seeds. To a lesser extent, Camellia japonica, Camellia sasanqua, Camellia reticulata, and C. sinensis are also propagated for oil production. Adding to the confusion, these edible oils are often also marketed as “tea oil” or “tea seed oil” (Liang et al., 2017). In the present book chapter, however, tea seed oil referred to the edible oil derived from the seeds of C. oleifera. The C. oleifera seed oil is also known as camellia oil or camellia seed oil in the literature (Yang et al., 2016). C. oleifera, having primarily a subtropical and warm temperate distribution, is represented in China, India, Japan, Brazil, South Korea, and Southeast Asia. This tree shrub could reach up to 6 m (20 feet) in height with the extensive, fine branching, and multiple vertical trunks. The broad evergreen leaves are between 5 and 10 cm (2
4 inches) in length and they are well loved for the large single white flowers with pleasant fragrance (Gilman & Watson, 1993; WFO, 2021). Today, tea seed oil serves as the major edible cooking oil at southern provinces of China and is slowly gaining popularity globally. The global camellia oil market is forecasted to grow with a compound annual growth rate of 24.3% within the 5-year period from 2020 to 2025. By 2025, the oil is estimated to reach a market size of USD 93.97 billion, from USD 39.35 billion in 2019 (Marketquest.biz, 2020).

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00022-2

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© 2022 Elsevier Inc. All rights reserved.

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19. Biological activities of tea seed (Camellia oleifera Abel.) oil

19.2 Chemical composition of tea seed oil Often referred to being the “Eastern Olive Oil,” tea seed oil shared a similar fatty acid profile of olive oil. Both edible oils are rich in the monounsaturated oleic acid, with concentrations ranging around 60%
80%. This contributes to the high monounsaturated fatty acids (MUFAs) in the lipid fraction of tea seed oil and possibly relate to its health-promoting properties (Wang et al., 2017a; Zeng & Endo, 2019). As listed in Table 19.1, the other major fatty acid composition of tea seed oil includes palmitic acid, linoleic acid, and stearic acid. TABLE 19.1 Chemical composition of tea seed oil. Component Fatty acid

Common name

Concentration %

References

C14:0

Myristic acid

0.03
0.07

(Ma et al., 2011; Wang et al., 2017a)

C16:0

Palmitic acid

7.92
11.42

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

C16:1

Palmitoleic acid

0.00
0.25

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

C18:0

Stearic acid

1.70
2.71

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

C18:1

Oleic acid

67.74
82.10

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

C18:2

Linoleic acid

6.61
13.18

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

C18:3

α-Linoneleic acid

0.20
0.51

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

C20:0

Arachidic acid

0.03
0.06

(Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Zeng & Endo, 2019)

C20:1

Gadoleic acid

0.41
0.81

(Fang et al., 2015; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016)

C22:1

Erucic acid

0.03
0.50

(Ma et al., 2011; Wang et al., 2017a; Zeng & Endo, 2019)

C24:0

Lignoceric acid

0.03
0.10

(Ma et al., 2011; Wang et al., 2017a; Zeng & Endo, 2019)

C24:1

Nervonic acid

0.05
0.14

(Ma et al., 2011; Yang et al., 2016)

Total SFA

6.65
11.82

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

Total UFA

81.93
90.18

(Fang et al., 2015; Hu & Yang, 2018; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

Total MUFA

68.43
82.67

(Fang et al., 2015; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019) (Continued)

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19.2 Chemical composition of tea seed oil

TABLE 19.1 Component Fatty acid

239

(Continued) Common name

Concentration %

References

Total PUFA

6.53
13.50

(Fang et al., 2015; Ma et al., 2011; Wang et al., 2017a; Yang et al., 2016; Zeng & Endo, 2019)

Tocopherols and Tocotrienols

mg/kg

α-Tocopherol

59.60
250.00

(Fang et al., 2015; Fazel et al., 2008; Hu & Yang, 2018; Wei et al., 2016; Wen et al., 2020; Zeng & Endo, 2019)

β-Tocopherol

N.D.
50.00

(Fang et al., 2015; Fazel et al., 2008; Hu & Yang, 2018; Wei et al., 2016; Wen et al., 2020)

γ-Tocopherol

6.20
24.05

(Fazel et al., 2008; Hu & Yang, 2018; Wei et al., 2016; Wen et al., 2020)

δ-Tocopherol

N.D.
11.53

(Fazel et al., 2008; Hu & Yang, 2018; Wei et al., 2016; Wen et al., 2020)

α-Tocotrienol

N.D.
120.9

(Fazel et al., 2008; Wei et al., 2016; Wen et al., 2020)

β-Tocotrienol

N.D.
2.28

(Fazel et al., 2008; Wei et al., 2016; Wen et al., 2020)

γ-Tocotrienol

N.D.
23.55

(Fazel et al., 2008; Wei et al., 2016; Wen et al., 2020)

δ-Tocotrienol

N.D.

(Fazel et al., 2008; Wei et al., 2016; Wen et al., 2020)

Other compounds

mg/kg

Lanosterol

715.19
1202.80 (Wang et al., 2017a; Zeng & Endo, 2019)

β-Amyrin

520.00
913.15

(Wang et al., 2017a; Zeng & Endo, 2019)

Stigmast-7-en-3ol

269.73
552.87

(Wang et al., 2017a; Zeng & Endo, 2019)

Betulin

165.57
330.56

(Wang et al., 2017a)

Cycolartenol

164.00
1093.67 (Wang et al., 2017a; Zeng & Endo, 2019)

β-sitosterol

123.23
240.12

(Wang et al., 2017a)

Squalene

122.02
248.24

(Fang et al., 2015; Wang et al., 2017a)

Lupeol

121.00
381.17

(Wang et al., 2017a; Zeng & Endo, 2019)

Canophyllol

110.66
179.97

(Wang et al., 2017a)

Campesterol

27.50
60.45

(Wang et al., 2017a)

Total phenolic compounds

6.32
39.47

(Fang et al., 2015; Wang et al., 2017b)

N.D., Not detected; SFA, saturated fatty acid; UFA, unsaturated fatty acid; MUFA, monounsaturated fatty acids; PUFA, polyunsaturated fatty acid.

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19. Biological activities of tea seed (Camellia oleifera Abel.) oil

Triacylglycerol profiling revealed that the principal triacylglycerols detected in tea seed oil are oleic
oleic
oleic (OOO; 52.19%
63.87%), palmitic
oleic
oleic (POO; 15.57%
24.18%), linoleic
oleic
oleic (LOO; 7.29
8.98), palmitic
oleic
palmitic (POP; 1.55%
3.78%), linoleic
oleic
linoleic (LOL; 1.66%
3.15%), and palmitic
linoleic
linoleic (PLL; 0.88%
1.59%). It was not surprising that unsaturated fatty acid (UFA), specifically the high percentage of oleic acid, is the predominant fatty acid at sn-2 position of triacylglycerol in tea seed oil. This is followed by linoleic acid as the second abundant fatty acid at triacylglycerol sn-2 position (Wei et al., 2016). Literatures have shown that the positional distribution of fatty acids in triacylglycerol may relate to the absorption efficiency and metabolism (Cheng et al., 2019; Teh et al., 2018). Analysis on the tocopherol and tocotrienol contents showed that tea seed oil contains considerable amount of α-tocopherol and α-tocotrienol (Fang et al., 2015; Fazel et al., 2008; Hu & Yang, 2018; Wei et al., 2016). However, when compared to the other edible vegetable oils, the total tocols content appears to be insignificant (Wen et al., 2020). The main minor compounds present in tea seed oil include the pentacyclic triterpenoids, β-Amyrin and lanosterol, as well as the free and bound phenolic compounds that potentially account for some of the antioxidant activities of this oil (Wang et al., 2017a; Zeng & Endo, 2019). Among the main phenolic acids detected are benzoic acid (10.38%
30.89%) and cinnamic acid (17.30%
27.84%) (Wang et al., 2017b). Importantly, it is noted that the different parameters including variety, geographical region, and farming condition might not exert a major impact on the fatty acid profile and physicochemical properties of tea seed oil (Hu & Yang, 2018; Wang et al., 2017a; Yang et al., 2016). Nevertheless, the extraction and process of refining, bleaching, and deodorizing can hugely affect the chemical composition of the final tea seed oil product (Fang et al., 2015; Lee et al., 2014; Qizhi et al., 2008; Wei et al., 2015). In particular, oil extraction from tea seed is challenging due to the foaming tendency of the tea saponin that accounts for 7.28%
16.24% of the tea seed on dry weight basis (Li et al., 2010; Wang et al., 2008). While different techniques including organic solvent extraction, ultrasound-assisted and microwave puffing-pretreated aqueous enzymatic process, supercritical fluid extraction, subcritical water extraction, and steam explosion extraction have been proposed and used industrially, the search for a low-cost and highly efficient tea seed oil extraction technique continues (Fang et al., 2016; Wu & Li, 2011; Wu et al., 2018; Zhang & Jin, 2011; Zhang et al., 2019; Zhou et al., 2012).

19.3 Biological activities Present knowledge on the biological activities of tea seed oil is reviewed and discussed in present chapter (Fig. 19.1).

19.3.1 Improve lipid profiles It has been well established that dietary fatty acid composition is a major determinant affecting the regulation of lipid metabolism. Although the relationship between ingested

Multiple Biological Activities of Unconventional Seed Oils

19.3 Biological activities

241

FIGURE 19.1 Summary of biological activities of tea seed (Camellia oleifera Abel.) oil [CC BY-NC-SA 2.0].

lipid and blood cholesterol or lipid markers is uniquely complicated, data from both animal and clinical studies have demonstrated the potential of tea seed oil to improve lipid metabolism. Both Huang’s and Suanarunsawat’s research teams investigated the effect of supplementing tea seed oil in rat fed with either a high-fat or high-fat high-carbohydrate diet. The dosages of tea seed oil treatment were in the range of 1.5
9.0 g/kg body weight (Huang et al., 2011; Suanarunsawat et al., 2014). Following seven consecutive weeks of tea seed oil intervention, the Huang’s team reported lower serum triglycerides and cholesterol levels, along with mild liver pathological fatty change, when comparisons were made to the control group (Huang et al., 2011). The study by Suanarunsawat and co-authors was conducted over a period of 3 months. Similar findings of having lower total cholesterol, triglycerides, LDL-cholesterol, and atherogenic index in comparison to the high-fat high-carbohydrate diet control group were recorded at the end of the treatment period. At the same time, although the fasting blood glucose level at the end of the study was similar to the control, tea seed oil appeared to afford protective effect by preventing glycemic spike. A gradual rise and steady return to normal range of blood glucose was observed in the oral glucose tolerance test (Suanarunsawat et al., 2014). A single-blind, randomized, controlled crossover clinical study involving the participation of 12 healthy men volunteers was performed to further validate the cardioprotective effect of tea seed oil. The volunteers were all having normal body weight and age between 19 and 31 years old. During the 3-week intervention period (with a 3-week washout period in between), the participants were restricted to consume only the provided diet. A total of 40 g per day of tea seed oil or virgin olive oil were being spread out across the breakfast, lunch, and dinner meals. It was interesting to note that there were no significant differences in plasma lipid peroxidation, antioxidant enzyme activities, and anthropometrics parameters, either between or within the groups and even

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242

19. Biological activities of tea seed (Camellia oleifera Abel.) oil

prior to or after intervention. Furthermore, no significant differences in baseline plasma lipids and between-group differences were noted at the end of the treatment. When compared to the baseline, however, lower total cholesterol and LDL-cholesterol levels, as well as systolic blood pressure, were observed in the tea seed oil treatment group (Suealek et al., 2021). In 2020 a research team in China had planned for a three-arm, randomized, double-blind, placebo-controlled feeding trial focusing on the usage of tea seed oil in traditional Chinese cooking methods (Wu et al., 2020). It is expected that all these findings will further substantiate the potential of tea seed oil to improve lipid metabolism. On the contrary, despite the fact that tea seed oil demonstrated potential cardioprotective properties in several animal and clinical studies, a recent 12-week in vivo study by Li and Shen did not find any statistical difference on serum lipids and lipoproteins of the tea-seed-oil-rich high-fat-diet-fed rats. In this study, the rats were first fed high-fat diet for 5 weeks, followed by the tea-seed-oil-based high-fat-diet intervention (Li & Shen, 2020). It remains unclear, however, if the experimental treatment or condition might have contributed to the differences observed. In particular, tea seed oil was administered by oral gavage in the studies by Huang et al. (2011) and Suanarunsawat et al. (2014), where Li and Shen (2020) incorporated tea seed oil in the preparation of high-fat diet directly. Li and Shen have suggested that the observation might relate to the PUFA n-6/n-3 ratio and some other factors that worth further investigation (Huang et al., 2011; Li & Shen, 2020; Suanarunsawat et al., 2014).

19.3.2 Ameliorate hypercholesterolemia-induced ocular disorder It has been proposed that buildup of cholesterol deposits contribute toward atherosclerosis and macular degeneration. The onset or progression of macular degeneration could be delayed or prevented with improved lipids and lipoproteins metabolism (Van Leeuwen et al., 2018). The Li’s research team had previously investigated the protective effect of tea seed oil against vascular degeneration in the ocular fundus and atherosclerosis induced by high-fat diet. New Zealand rabbits were used as the animal model. The report demonstrated that the administration of tea seed oil for 2 months alleviated vascular changes in the ocular fundus artery, mostly associated with the cholesterol-lowering mechanism afforded by tea seed oil (Li et al., 2012).

19.3.3 Improve physical performance and prevent fat accumulation Another study performed on ovariectomized animal model investigated the effect of tea seed oil against menopause-related metabolic syndromes. The different groups of ovariectomized mice were fed high-fat diet with different composition of tea seed oil, soybean oil, and lard. After 12-weeks intervention period, it was reported that the tea seed oil treatment group recorded lower body weight as well as relative uterus peripheral fat mass and total fat. Histopathological analysis revealed a reduction of adipocyte sizes in brown adipose tissue and uterus fatty peripheral, along with decreased hepatic lipid accumulation (Tung et al., 2019). Similar to the study by Suanarunsawat team, improved glucose tolerance was also observed in the animals and may account for the attenuation of body fat

Multiple Biological Activities of Unconventional Seed Oils

19.3 Biological activities

243

accumulation (Suanarunsawat et al., 2014). It is worth noticing that even the hot water extract of defatted C. Oleifera seed meal may exert effect on regulating adipokine secretion and thereby decrease abdominal fat accumulation (Yang et al., 2019). In addition, the Tung’s research team had also investigated the effect of tea seed oil consumption on physiological adaptations to exercise. It was interesting to discover that tea seed oil consumption improved endurance performance with a longer exhaustive swimming time when compared to the animals fed with diet rich in either polyunsaturated or saturated fatty acids. The reduced physical fatigue might relate to the lower concentrations of fatigue-associated biochemical indices including ammonia, blood urea nitrogen (BUN), and creatine kinase (CK) (Tung et al., 2019).

19.3.4 Mediate hepatoprotective activity The hepatoprotective mechanisms of tea seed oil were investigated using both high-fatdiet-induced hepatic lipid accumulation and carbon tetrachloride (CCl4)-induced hepatotoxicity models. Suanarunsawat et al. (2014) conducted the animal experimentation using high-fat high-carbohydrate diet. At the end of the 3-month intervention, it was noticed that the high levels of cardiac marker (CK-MB), kidney function marker (BUN), as well as liver function markers (aspartate aminotransferase, AST, alanine aminotransferase, ALT, and lactate dehydrogenase, LDH) in the high-fat high-carbohydrate-fed control group were improved with the administration of tea seed oil. Another study by Huang et al. (2011) was carried out on high-fat-diet-induced nonalcoholic fatty liver disease (NAFLD) animal model. The authors showed that tea seed oil intervention reduced fat accumulation in the liver, where a modest liver steatosis was observed in comparison to the high fat control. It is interesting to note that the extract prepared from the defatted tea seeds may also alleviate hepatic steatosis through the regulation of adipokines and energy homeostasis. Contrarily, a more recent report by Li and Shen demonstrated equal or increased risk of tea seed oil consumption in inducing NAFLD when compared to cocoa butter, soybean oil, and olive oil. While there were no significant differences in the recorded body weights following ad libitum high-fat diet rich in the respective edible oils, enlarged liver of more than 100% in comparison to regular and control diet groups was noticed. Cytological study of the hepatic cells showed moderate predominant of microvesicular fatty change and scattered macrovesicular fat droplets for the tea seed oil group. Specific accumulation of hepatocellular lipid droplets in tea seed oil group was greater than that of cocoa butter and soybean oil but lesser when compared to olive oil. Further ultrastructural analysis associated the lipid droplets accumulation to the degree of damage on mitochondria and endoplasmic reticulum integrity (Li & Shen, 2020). On the other hand, the studies by Lee et al. (2007) and Lei et al. (2020) demonstrated hepatoprotective effects of tea seed oil administration against CCl4-induced liver damage. In the study by Lee et al. (2007), rats were fed tea-seed-oil-incorporated diet for six consecutive weeks. On the last day of treatment, CCl4 was administered intraperitoneally and the animals were sacrificed at 24 h postinjection. The results demonstrated that tea seed oil inhibited fatty degeneration, reduced the serum levels of hepatic enzyme markers (ALT,

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19. Biological activities of tea seed (Camellia oleifera Abel.) oil

AST, and LDH) and peroxidation product malondialdehyde, while elevated the antioxidant enzymes activities [glutathione peroxidase (GPx), glutathione reductase (GR), and glutathione-S transferase (GST)] and hepatic glutathione content. Lei and coauthors performed similar experimentation on C57BL/6J mice. The mice received intraperitoneal injections of CCl4 twice weekly for a total of 6 weeks. After the first 2 weeks of CCl4 intervention, the mice were concomitantly treated with daily intragastrical administration of tea seed oil (2 mL/kg body weight) for 1 month. Likewise, tea seed oil was found to improve liver function and antioxidant capacity. Histopathological liver lesions were ameliorated. Further investigations into the mechanisms of action suggested that tea seed oil may exert its action by regulating TGF-β/SMAD signaling in the control of cell growth, differentiation, and apoptosis (Lei et al., 2020).

19.3.5 Modulate gastrointestinal protective effect It has been established that the frequent exposure of HCl, pepsin, bile acids, ethanol, nonsteroidal antiinflammatory drugs (NSAIDs), Helicobacter pylori toxins, and other noxious substances are associated with increased risk of gastrointestinal (GI) injuries and complications. The adverse events vary from the asymptomatic endoscopic lesions to bleeding, perforation, and stenosis of ulceration. Maintaining a proper balance between exposures to aggressive factors and mucosal defensive mechanisms has been proposed to reduce or limit GI mucosal injury (Sharifi-Rad et al., 2018). Tea seed oil was reported to exert GI protective effect in both in vitro and animal studies. Briefly, the treatment of HeLa-derived human intestinal epithelial (Int-407) cell line with tea seed oil (25
75 μg/mL) increased the mRNA expression of antioxidant markers [HO-1, GPx, and superoxide dismutase (SOD)]. A concentration-dependent enhancement of cell migration, along with the elevated production of vascular endothelial growth factor (VEGF) and prostaglandin E2 (PGE2) proteins were also observed. Increased expression of VEGF and PGE2 functions to maintain mucosal integrity and protect the GI track against oxidative injury (Cheng et al., 2014). Another in vitro study using the rat gastric mucosal (RGM-1) cell line showed similar result findings of enhanced cellular migration ability following the treatment of tea seed oil. Furthermore, pretreatment of RGM-1 cell line with tea seed oil for 6 hours significantly decreased ethanol-induced stress, where heat shock proteins (HSP32, HSP60, HSP70, and HSP90) were induced to maintain cellular homeostasis. The expressions of apoptosisrelated proteins (Bax, cytochrome c, and caspase-3) were also reduced, while an increase in antiapoptosis-related protein (Bcl-2) expression was discovered. Further cell cycle analysis revealed decrease in sub-G1 peaks, thereby suggesting protecting role of tea seed oil against ethanol-induced stress and apoptosis (Tu et al., 2017). For animal study, both ketoprofen- and alcohol-induced GI mucosal damage models were employed. In the study by Cheng et al. (2014), the animals received daily oral dosage of tea seed oil, in the range of 1
4 mL per kg bodyweight, for a period of 3 weeks. Ketoprofen (50 mg per kg bodyweight) was administered orally on the last day of treatment and the animals were sacrificed at 24 hours postinjection. The results demonstrated that tea seed oil reduced oxidative impairment in the GI mucosa by reversing the impairment of the antioxidant system. Increased antioxidant enzymatic activities,

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245

including CAT, GPx, GR, GST, and SOD, as well as oxidized/reduced glutathione ratio were reported. Concomitantly, tea seed oil also reduced the excess NO and inhibited the production of IL-6 and COX-2 protein expressions (Cheng et al., 2014). As for the ethanol-induced gastric injury model, the mice were also pretreated for 3 weeks with daily oral gavage of tea seed oil (0.5
2 mL per kg bodyweight). At the end of the study, 5 mL per kg bodyweight of absolute ethanol was orally administered, and the animals were sacrificed after 1 hour. Histopathological evaluation revealed that pretreatment with tea seed oil ameliorated ethanol-induced acute injury of the gastric mucosa. There was a significant decrease in histological injury and hemorrhage scores, along with moderate submucosal edema and leukocytes infiltration. This was coupled with dosedependent improvement in antioxidant enzyme activities, heat shock proteins, and PGE2 production, as well as suppression of NO production, lipid peroxidation, and expression of pro-inflammatory cytokines and apoptosis-related proteins (Tu et al., 2017).

19.3.6 Exert antihypertension effect A compelling body of scientific research and evidences has indicated that multiple dietary factors are major determinants in the pathogenesis of hypertension. Effect of salt, potassium, and fiber consumption on blood pressure is well established but remains unclear for the other nutrients and foods (Appel, 2017). In vivo experimental study using spontaneously hypertension rats showed that the administration of tea see oil significantly lowered the systolic blood pressure in both the acute 24-hour and 4-week experimentations. The low and high dosages (1.5 and 4.5 g/kg body weight, respectively) of tea seed oil were used in the study (Guo et al., 2020). Angiotensin-converting enzyme (ACE) is involved in the conversion of inactive decapeptide angiotensin I into octapeptide angiotensin II. Being the active peptide of the reninangiotensin system (RAS), angiotensin II exerts a central function in regulating blood pressure and homeostasis of fluid and electrolyte. Analysis on ACE activity in the different organs of the spontaneously hypertension rats revealed that the low dosage of tea seed oil significantly reduced the ACE activities in the aorta, heart, lung, liver, and kidney. Meanwhile, a marked descent in ACE activities is only observable in heart, lung, and liver for the high dosage treatment. The serum angiotensin II concentrations, however, are significantly lower for both treatment groups when compared to the control. Further serum biochemical indices analysis showed that tea seed oil modulated the concentrations of tumor necrosis factor-α (TNF-α), endothelin 1 (ET-1), endothelial nitric oxide synthase (eNOS), nitric oxide (NO), GST, and lactate dehydrogenase isoenzyme (LDH-1). It is hence postulated that tea seed oil may exert antihypertension effect by regulating the delicate balance between endotheliumderived vasodilators and vasoconstrictors (Guo et al., 2020).

19.3.7 Serve as potential neuroprotective agent Accumulating evidences have asserted the importance of microbiota
gut
brain axis in affecting the progression of Alzheimer’s disease (AD). Alterations of gut microbiota composition, occurring through diet, disease, or other environmental influences, lead to the

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19. Biological activities of tea seed (Camellia oleifera Abel.) oil

increased permeability of gut barrier. This is followed by immune activation and systemic inflammation, which further impair the blood
brain barrier function, induce neuroinflammation and a consequent neurodegeneration (Megur et al., 2021). In vivo study using aluminum-chloride-induced rat model showed the potential of tea seed oil in mitigating the progression of AD-like behavioral disturbances. Both low- and high-dose tea-seed-oil-treated rats (1.5 and 3.0 mL/kg body weight, respectively) demonstrated better learning and memory capacity in comparison to the aluminum-chloridetreated group when assessed via the Morris water maze test. Further investigation revealed reduced biomarkers highly linked with AD progression, while autophagyassociated proteins were upregulated. Specifically, the protein levels of amyloid precursor protein (APP), beta-site APP-cleaving enzyme 1 (BACE1), beta-amyloid peptide 1
42 (Aβ 1
42), and TAU-5 were dramatically reduced by tea seed oil administration. On the other hand, increased expression of autophagy-related protein 5 (ATG5), microtubule-associated protein 1 light chain 3 isoform (LC3II), and Beclin-1 may revert the repression of autophagy as a result of tau protein accumulation (Weng et al., 2020). It is also interesting to note that the oral administration of tea seed oil significantly suppressed the receptor of advanced glycation end product (RAGE)-dependent NF-kB neuroinflammatory processes. The antioxidant enzyme levels, including SOD, GPx, and catalase, were improved. Contrarily, oxidative stress biomarker malondialdehyde (MDA), microglial activation, and pro-inflammatory cytokines induced in aluminum-chloridetreated rats were reduced following the administration of tea seed oil. In addition, the Enterobacteriaceae-dominant intestinal microbiota in the aluminum-chloride-treated rats shifted toward the increased abundance of Lactobacillus by the oral gavage of tea seed oil. It is hence proposed that the administration of tea seed oil may restore and remodel gut microbiome dysbiosis, resulting in the modulation of neuroinflammation and ultimately, the amelioration of AD pathogenesis (Weng et al., 2020). While preclinical data seems promising, detailed causal and functional therapeutic interventions in human are still necessitated to explore clinically relevant effects of tea seed oil usage in the prevention of AD.

19.3.8 Mediate antimicrobial activity The study by Fea´s et al. (2013) depicted the antimicrobial properties of tea seed oil on clinically isolated strains of gram-positive and gram-negative bacteria (Bacillus cereus and Escherichia coli, respectively), as well as yeast (Candida albicans). In particular, it was reported that the oil exerts greater growth inhibition on gram-negative bacteria in comparison to the gram-positive bacteria. While the mechanisms of action of the antimicrobial attributes remain to be elucidated, the report further substantiated the potential use of tea seed oil for food uses and industry applications. Other than antioxidant activity that immensely affects oxidative stability, the relatively long shelf life of tea seed oil may also dependent upon its antimicrobial activity (Sahari et al., 2004; Xuan et al., 2018).

19.3.9 Exert bone-protective role Owing to major hormonal changes in triggering estrogen deficiency, postmenopausal women are at increased risk for developing osteoporosis. Studies have shown that diet

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may play a role to improve osteoporosis fracture healing (Chiavarini et al., 2020). The study by Li and co-authors reported the protective effect of tea seed oil on ovariectomyinduced bone loss animal model. Specifically, the consumption of 5 mL/kg body weight of tea seed oil for a period of 12 weeks increased the serum concentration of calcium and phosphorus. Elevated serum estradiol coupled with a decrease in follicle-stimulating hormone levels was observed. In addition, the concentration of alkaline phosphatase, an important indicator for bone mineralization, was increased along with pathological improvement in osteoporotic changes (Li et al., 2012).

19.3.10 Exhibit antioxidant and anti-inflammatory properties The in vitro antioxidant and anti-inflammatory activities of tea seed oil had been studied using various methodologies. Rajaei et al. (2008) reported the peroxide and thiobarbituric values as the indicators of antioxidant efficacy. The DPPH (2,2-diphenyl-1picrylhydrazyl) free radical scavenging activity of tea seed oil was earlier described by Wang et al. (2011), where the oil extracted using supercritical carbon dioxide depicted a stronger scavenging ability in comparison to Soxhlet extraction. Chaikul et al. (2017) described the protective effect of tea seed oil on 3T3-L1 cell line after hydrogen peroxideinduced damage. It is proposed that the presence of oleic acid, polyphenols, vitamin E, sesamin, and 2,5-bis-benzo dioxol-5-yl-tetrahydro-furo [3,4-d] dioxine (compound B) might contribute synergistically in the antioxidant activity of tea seed oil (Lee & Yen, 2006; Sahari et al., 2004). The antioxidant and anti-inflammatory efficacies of tea seed oil were further evaluated in a randomized, single-blind controlled trial. Briefly, women with hypercholesterolemia (n 5 50) were randomly assigned to receiving either tea seed oil or soybeanoil-enriched diet. Forty-five milliliter of tea seed oil or soybean oil was incorporated into the daily provided three meals over the 8-week study period. At the end of the trial, remarkable reductions in the biomarkers of oxidative stress (malondialdehyde and oxidized LDL-C) were noted. While the levels of inflammatory biomarkers (TNF-α and IL-6) remain unchanged, the significant reduction of high-sensitivity C-reactive protein was observed after the intervention (Bumrungpert et al., 2016). Zhang and co-authors attributed the antiinflammatory effects of tea seed oil to the free, esterified, glycosylated and insoluble phenolic compounds present in tea seed oil (Zhang et al., 2021).

19.3.11 Suppress melanogenesis Being the main determining factor of skin and hair color, melanin functions to afford protection against UV-induced photodamage. However, pigmentation abnormalities might not be desirable. The modulation of melanin biosynthesis is considered as a crucial strategy for the treatment of abnormal pigmentation. The inhibitory effect of tea seed oil on melanogenesis was studied using the B16-F10 murine melanoma cell line. The in vitro assays revealed that tea seed oil significantly reduced the melanin content via the suppression of tyrosinase and tyrosinase-related protein 2 (TRP-2) activities (Chaikul et al., 2017).

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19.3.12 Potential lactogenic effect Traditionally, tea seed oil is also being consumed as a galactagogue food that promotes lactation in breastfeeding mothers. In vitro study using differentiated bovine mammary epithelial cells (MAC-T) demonstrated that tea seed oil upregulated de novo fatty acid synthesis via the sterol regulatory element-binding protein 1 (Srebp1) signaling pathway. The activated genes included Srebp1, acetylCoA carboxylase 1 (Acc), fatty acid synthase (Fasn), lipoprotein lipase (Lpl), and stearoyl-CoA desaturase (Scd). Concurrently, upregulated β-casein and downregulated αS1-casein mRNA expressions were observed, where it may be attributable to the activation of both PI3K-AKT-mTOR-S6K1 and JAK2-STAT5 signaling pathways. Nevertheless, further in vivo studies are still required to corroborate the lactogenic uses of tea seed oil (Zhong et al., 2020).

19.4 Concluding remarks and future trends Advances in understanding food and nutrient metabolism allow consumers to demand for healthier food products. Investigations on the biological activities of tea seed oil and its impacts on human health deserved notable attention. In this regard, the consumption of tea seed oil demonstrated nutritional balance and potential functional effects in multiple preclinical and clinical studies. These positive effects may relate to the oleic-acid-rich MUFA composition and the presence of varying bioactive compounds in tea seed oil. Nevertheless, it is also worth noticing that a recent study reported contradictory findings. Owing to increasing interest and evolving demands on tea seed oil, more intensive research activities are required to address vulnerabilities and challenges. It is suggested that future tea seed oil research should take consideration into four main core issues including (i) environmental sustainability in the farming and production; (ii) effective method of oil extraction; (iii) oil quality, purity, authenticity, and geographical traceability; as well as (iv) human consumption pattern of oil for evaluation on health and nutrition impact. It is hopeful that more active and engaging participation in tea seed oil research would improve the understanding and address the controversy over time.

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C H A P T E R

20 Biological activities of rubber (Hevea brasiliensis) oil Abdalbasit Adam Mariod1,2 and Haroon Elrasheid Tahir3 1

Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 2College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia 3School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China

20.1 Introduction Rubber (Hevea brasiliensis) is a plant species that follows the genus Alhevea of the Euphorbia family. The Brazilian Hevea is the rubber tree, also called the weeping tree, the tears tree, or the cauchuk, which means rubber in many modern languages. This tree was called the weeping tree, a clear reference to the way that the tree secretes the original rubber material. It is shed by drops in a way that the eyes shed tears. Wounds are made to facilitate the fall of those drops from them and workers tie at the end of the trunk a small vessel that receives these falling drops. The original wound is white in color and the tree does not start giving until after 7 years and continues to do so until it reaches 30 years. This tree grows in the south of the Asian continent, all located in the equatorial region. The world’s production of rubber is two million tons annually, and rubber is used in many things, including the manufacture of industrial and agricultural machinery and others, and it cannot run without tires (http://www.ilocis.org/documents/chpt80e.htm). Rubber tree is an evergreen tropical tree, ranging in height from 13 to 50 m, with a relatively slender stem and sharp-angled upward facing branches. Its leaves are three-leafed compound, its flowers are small, yellow, clustered, single-sex and lodging, and its fruit is a three-lobed box, each containing a seed. Its pollination is mixed with insects. Its seeds are large, oval-shaped, and hard-coated, up to 3 cm long (Fig. 20.1). About 11
12 species grow in the humid tropical forests of South America, producing rubber. The most important of these are the Brazilian rubber H. brasiliensis and two other types that are grown in humid tropical areas to produce natural rubber.

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FIGURE 20.1

Hevea brasiliensis seeds.

The rubber tree is of great industrial importance, as it produces latex, which is converted into rubber at a rate of 3
7 kg/tree annually at the age of 10
12 years, up to 25
30 years. About 90% of natural rubber is produced from rubber plantations and the rest from natural forests. Several millions of tons of natural rubber are produced annually, which is used as a basic material in many industries, and its volumetric weight (density) is estimated at 920 kg/m3. Onoji et al. (2016) extracted rubber seed oil by solvents and the oil content was found as 43%. These authors reported that the seeds contain low ash content (0.001%) and low moisture content (1.73%) by weight. The oil contains a high percentage of saturated fatty acids (30.67%) and monounsaturated fatty acids. Moderately low polyunsaturated (69.33%) was reported. This negligible presence of polyunsaturated fatty acids supported the higher thermal stability, and a slower rate of oxidation of the oil compared to other vegetable oils (Onoji et al., 2016).

20.2 Biological activities of rubber seed oil Rubber latex and its seed oil show many potentials in various biological activities such as antifungal, antioxidant, antimelanogenesis as well as a biomaterial in relation to angiogenesis (Ramarao et al., 2021). The oils produced from the seed oil bearing plants are considered a means to develop a new group of drugs that have the ability to control a wide range of diseases related to oxidative stress, as well as several types of infectious and pathogenic diseases. Many regions of the world offer various seed oil-producing plants, which can also be explored for their antioxidant activity and antimicrobial properties. Thus the seed oils can be used to increase the shelf life of food and industrial products. The antioxidant property of seed oils is a source of some applications such as the preservation of food products and the prevention of diseases related to oxidative stress, such as cancer and cardiovascular disorders. The antimicrobial property of seed oil enables it to be used to produce biologically active compounds that can be isolated, which leads to the discovery of new antimicrobials and compounds to combat various multidrug resistant microbial strains of infections in general (Saha et al., 2015). A study carried out by Chaikul et al. (2017) showed that the unsaturated fatty acid composition of rubber seed oil has biological activity and thus qualifies it for use in cosmetics. The study evaluated the cytotoxicity by sulforhodamine B assay and the biological

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activities, including the assay for melanogenesis and antioxidant activity, in cell culture. This study showed that the noncytotoxic concentrations of rubber seed oil were at the concentration of 0.0001
0.1 mg/mL and that the cell viability was above 80% in melanoma cells. The results of the study also showed that the concentration of rubber seed oil that inhibits cell viability at 50% is (IC50) 0.29 mg/mL in melanoma cells. Melanin formation assay showed that there is an inhibitory effect of rubber seed oil on melanin content and both tyrosinase activity and tyrosinase-related protein-2 activity. The study concluded that rubber seed oil has antioxidant activity, and these results supported the possibility of using rubber seed oil as a functional raw material used in personal care and cosmetics (Chaikul et al., 2017). The results of some studies (Singh & Kumar, 2015) indicated the presence of secondary metabolites such as flavonoids, alkaloids, tannins, cardiac glycosides, and stimulants with rubber H. brasiliensis extract, which turned out to have antimicrobial activity against many microbes such as E. coli, Pseudomonas aeruginosa, and Klebsiella. Kittigowittana et al. (2013) studied the cytotoxic effect of rubber seed oil on human dermal fibroblasts. The study showed that H. brasiliensis rubber seed oil is nontoxic to human skin cells and therefore may be suitable as an antioxidant for topical cosmetic applications and may be safe compared to synthetic materials and thus as a natural raw material for the cosmetic industry. Rubber seed oil consists of fatty acids that are beneficial for skin health. In this study, Lee et al. (2013) and his research group indicated that the total antioxidant capacity of rubber seed oil was very low or none at all. This may be due to the process of drying the seeds at 105 C, which may destroy the antioxidants within the seeds. It may be that the destruction of vitamin E and beta-carotene, which are the most active oxidizing factors, and therefore the destruction by heating for long periods and becomes inactive, which reduces the ability of antioxidant. Ahmed and his group in 2020 studied the analgesic and antidiarrheal activity of the rubber methanolic extract. The analgesic activity was evaluated by meta-analysis induced by acetic acid and antidiarrheal by gastrointestinal motility method (charcoal meal test) in mice. The researchers conducted a phytochemical evaluation and their results showed a large presence of alkaloids, carbohydrates, glycosides, saponins, phytosterols, proteins, amino acids, fats, and fixed oils. The results of the analgesic evaluation showed a significant activity in comparison with the control group diclofenac Na. On the other hand, the study showed that the antidiarrheal activity significantly reduces the thrust of charcoal (Ahammed et al., 2020).

20.3 Conclusion H. brasiliensis tree produces a milky colored rubbery sap with different industrial uses. The seeds which considered as a by-product contain 43% of nonedible oil with high amount of saturated and monounsaturated fatty acids, but moderately low polyunsaturated fatty acid. The seed oil shows various biological activities such as antifungal, antioxidant, antimelanogenesis as well as a biomaterial in relation to angiogenesis.

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7. Lee, N. Y., Setapar, S. H. M., Sharif, N. S. M., Ahmad, A., Khatoon, A., Azizi, C. Y. M., & Idayu, M. I. (2013). Extraction of rubber (Hevea brasiliensis) seed oil using supercritical carbon dioxide and soxhlet extraction. Research Journal of Chemistry and Environment., 17, 46
52. Onoji, S. E., Iyuke, S. E., & Igbafe, A. I. (2016). Hevea brasiliensis (rubber seed) oil: Extraction, characterization, and kinetics of thermo-oxidative degradation using classical chemical methods. Energy & Fuels, 30(12), 10555
10567, 2016. Ramarao, M. D. R., Thong, O. M., & Elumalai, S. (2021). Therapeutic potential of rubber latex: A review. Agricultural Reviews (42), 99
104. Saha, P., Talukdar, A. D., Ningthoujam, S. S., Choudhury, M. D., Nath, D., Nahar, L., & Basar, N. (2015). Chemical composition, antimicrobial and antioxidant properties of seed oil plants of North-East India: A review. CELLMED, 5(3), 17.1
17.22. Available from https://doi.org/10.5667/TANG.2015.0010. Singh, S. K., & Kumar, S. S. (2015). Phytochemical and antibacterial efficacy of Hevea brasiliensis. Journal of Chemical and Pharmaceutical Research., 7(12), 777
783.

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C H A P T E R

21 Biological activities of pequi (Caryocar brasiliense Camb.) pulp oil Daniele Paula (de Almeida)1, Arthur da Capela (Pompilio)2, Alisson Felipe Martins (Lima)2, Nataly Costa (de Almeida)2 and Carini Lelis (Aparecida)3 1

Federal Institute of Sa˜o Paulo (IFSP), Sa˜o Paulo, SP, Brazil 2Department of Food Technology, Federal University of Vic¸osa (UFV), Vic¸osa, MG, Brazil 3Center for Food Analysis (NAL), Technological Development Support Laboratory (LADETEC), Federal University of Rio de Janeiro (UFRJ), Cidade Universita´ria, Rio de Janeiro, RJ, Brazil

21.1 Introduction Pequi (Caryocar brasiliense Camb.) belonging to the family Caryocaraceae is a typical Brazilian Cerrado fruit. The Brazilian Cerrado e´ composed by states of the Minas Gerais, Para´, Mato Grosso, Mato Grosso do Sul, Goia´s, Distrito Federal, Sa˜o Paulo, Parana´ and Piauı´, Tocantins, Ceara´ e Maranha˜o with great economic importance in these regions (Lea˜o et al., 2018). The part more consumed and commercialized of the fruit is the pulp being utilized in the preparations such as typical prats, liquors, and candy. The pequi pulp is rich in vitamins, proteins, lipids, and vitamins. The nutritive valor pulp is determined mainly by lipid fraction, for example, unsaturated fatty acids, such as, oleic acid, linoleic acid, and linolenic acid. Besides, pequi (Caryocar brasiliense Camb.) has natural antioxidants in its composition, such as phenolic and carotenoid compounds. These compounds are associated with the development and maintenance of human health and the reduction of the risk of degenerative diseases (Azevedo-Meleiro & Rodriguez-Amaya, 2004; Mariana et al., 2013). According to studies previously developed, these compounds confer health benefits due to the high antioxidant capacity (Santana et al., 2013). Due to functionality, this fruit can promote some benefits as protection against degenerative diseases such as cancer, cardiovascular and cerebrovascular diseases (Mendonc¸a et al., 2017).

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The Pequi can be considered “gold cerrado” the application of pequi goes beyond culinary use, with oils and essences being the main products obtained from processing. The pequi pulp can be extracted mainly from the cooking of the fruits, via mechanical extrusion and the use of solvents. The pequi pulp use is carried out in the cosmetic industry in the production of soaps and creams for the skin; and in the food industry, benefited for the production of new foods, in the preparation of fried foods, the manufacture of liquors and seasonings, this due to its chemical properties and characteristic aroma. However, popular use has shown that pequi oil has a traditional use for medicinal purposes, treatment of some types of disorders, such as respiratory diseases, edema, ophthalmic problems related to low vitamin A intake, burns, wound healing, bruising, and swelling (Ombredane et al., 2020). In this regard, some studies report evidence that corroborates these antiinflammatory, cardioprotective, and antigenotoxic effects. Currently, studies have shown that pequi pulp oil in animal models has demonstrated antioxidant, antiinflammatory, cardioprotective, hepatoprotective, anticarcinogenic and antigenotoxic activity. Thus, it is necessary to expand the knowledge and the importance of this plant for the dissemination and awakening of new scientific interests in this natural product with an enriching potential.

21.2 Pequi The pequi (Caryocar brasiliense Camb.) belongs to the family Caryocaraceae and represents a typical fruit of the Brazilian Cerrado with significant economic importance for the population of this region (Lea˜o et al., 2018). The Cerrado Biome is the second-largest Brazilian plant formation after the Amazon and stands out for the heterogeneity of the vegetation, containing a high number of elements of fauna and, mainly, of flora. The vegetation comprises, from the high cerrada˜o (trees about 20 m high), a more common savanna (a dense thicket and with tree species 8
10 m high) up to the forms of open pasture (Leite et al., 2006), the occurrence of each type of vegetation being greatly influenced by the characteristics of the environment. In this biome, several species stand out due to the production of fruits of exotic colors and flavors, constituting alternative sources of nutrients, in addition to providing other bioactive compounds with antioxidant potential (Roesler et al., 2007; Silva et al., 2008). The pequizeiro, whose scientific name is Caryocar brasiliense, is a medium-sized tree, typical of the Cerrado, whose fruits are called pequi (Washington Luis de Oliveira e AldicirScariot, 2011). Among the genus Caryocar, Caryocar brasiliense Camb. is the most abundant in Brazil and can be found in the Cerrado, Amazon Forest, Caatinga, and Atlantic Forest (Almeida et al., 2018). The popular name of pequi (Caryocar brasiliense Camb.) varies from region to region and is popularly known as piqui, piquia´-bravo, almond-of-thorn, horse-grain, pequia´, pequia´-pedra, pequerim, suari, and piquia´. The name of indigenous origin, where “py” means skin and “qui,” thorn, is due to many thorns in the fruit’s endocarp (Magalha˜es, 1988). The pequizeiro fruit (Caryocar brasiliense Camb.) is classified as a drupe and generally contains between 1 and 4 seeds per fruit and consists of greenish-brown epicarp, external mesocarp formed by a white pulp and internal mesocarp (an edible portion of the fruit), light yellow to dark orange (Alves et al., 2014). It has a strong odor and contains a prickly

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FIGURE 21.1

(A) Pequizeiro fruit (Caryocar brasiliense Camb.). (B) External mesocarp formed by a white pulp. (C) Internal mesocarp (edible portion of the fruit) light yellow to dark orange. (D) Prickly endocarp. (E) The seed which is also called “Almond.”

endocarp protecting the seed, also called “Almond” (Fig. 21.1) (De Oliveira Sousa et al., 2011). Although the almond is edible, it is less consumed due to a large number of thorns. As can be seen, this agricultural by-product has technological potential; however, few applications have been reported in the literature, such as pectin extraction (Lea˜o et al., 2018) and flour production (Lea˜o et al., 2018). The most consumed and commercialized part of the pequi fruit is the pulp, for being highly caloric and for having a strong flavor, characteristic of regional cuisine, making it a valued spice and, thus, used in different preparations, such as rice with pequi, chicken ´ vila, 2010). However, the use of with pequi, farofa, liqueurs, among others (Carraza & A pequi goes far beyond cooking, considered as gold from the Cerrado, and essences and oils can be extracted from it (do Nascimento, 2008). Popularly, the leaves and flowers of the pequizeiro and the pulp oil of the pequi are used in the treatment of respiratory and ´ vila, 2010). liver diseases and are used as an aphrodisiac substance (Carraza & A

21.3 Nutritional composition The fruit’s pulp stands out for the number of lipids (8
33 mg/100 g) in terms of nutrients. This content is influenced by its native region (Nascimento-Silva & Naves, 2019). The pulp’s fatty acid profile comprises about 60% of unsaturated fatty acids, the pulp and almond being characterized by the high concentration of monounsaturated fatty acids, mainly oleic acid (54
60 g/100 g and 45 g/100 g, respectively). The high concentration of lipids in its pulp makes this fruit of great economic importance for the Cerrado population and has expressive for application in the food and cosmetics industry. According to the Brazilian Food Composition Table (TBCA, 2020), the pulp provides 185 kcal/100 g, constituting a good energy source. The pequi oil (pulp and almond), in contrast, contains a high content of saturated fatty acids, predominantly palmitic acid (33
44 g/100 g of total lipids) (Barra et al., 2013; Nascimento-Silva & Naves, 2019).

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Another relevant aspect is its considerable content of dietary fibers, including pectin (rhamnogalacturonan) and hemicellulose (arabinogalactans, xylans, and glucomannans) (Lea˜o et al., 2018). The pequi pulp has high dietary fiber levels (8
15 g/100 g), mainly insoluble fibers (Nascimento-Silva & Naves, 2019). Still, according to Sousa et al. (2011) and Monteiro et al. (2015), the pequi almond has a high content of total dietary fiber, while the shell has dietary fiber (6.52 g/100 g) and insoluble fiber (5.05 g/100 g). Regarding the mineral profile, the pequi pulp has many levels of magnesium, zinc, and phosphorus (Ramos & Souza, 2011). Also, the pequi pulp contains a high content of vitamin C (78.3 mg/100 g) and vitamin E (Palmeira et al., 2015) and carotenoids with pro-vitamin A activity (Vilas Boas et al., 2013).

21.4 Bioactive compounds of pequi As discussed earlier, pequi consists of an excellent source of proteins, lipids, and fibers needed in daily food. These fruits also have bioactive compounds in their composition that can be used as functional ingredients in foods for nutraceutical purposes (Batista & De Sousa, 2019). Thus, pequi has great acceptability in Brazil and has also aroused researchers’ interest due to its potential to explore different compounds important for health (Magalha˜es et al., 2019). The yellow-orange fruit has phenolic compounds and a high content of carotenoids, about 5.4
27 mg of total carotenoids per 100 g of pulp, such as β-carotene, zeaxanthin, violaxanthin, and lutein, which are capable of promoting benefits to human health due to its antioxidant capacity (Machado et al., 2015; Pinto et al., 2018). Also, the average vitamin C content is 45 mg of vitamin C per 100 g of pulp (Cordeiro et al., 2013; Preedy, 2012). The consumption of 100 g of pequi pulp is enough to meet 57.3%
66.9% of the daily vitamin A recommendation (Torres et al., 2018) (Fig. 21.2). FIGURE 21.2 Internal mesocarp (edible portion of the fruit) light yellow to dark orange.

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Among the products obtained, pequi pulp oil is the most used because of the content of natural antioxidants such as different carotenoids, vitamin C, and phenolic compounds. Besides, it is composed of different fatty acids, including unsaturated fatty acids (58%), such as oleic acid (omega-9) (51%), linoleic acid (omega-6) (0.8%
3%), and acid linolenic (omega-3) (0.2%
0.4%) (Comunian et al., 2020). However, these compounds’ quantity is influenced by factors such as the region, the type of cultivation, and the plant’s genetics. These compounds can be recovered from the fruit through different extraction processes that allow full use of the fruit, such as the endocarp, which also have functional compounds (Machado et al., 2013). Products obtained from pequi can be used as ingredients in the food industry and replace synthetic antioxidants. However, the exploitation of most native plants in the Cerrado is taking place in a predatory and unsustainable manner, threatening the preservation of species, which makes their study of great importance for proper management and better use in human food (Batllebayer et al., 2010; Novaes et al., 2013) and add value to the Brazilian product (Machado et al., 2013). The valorization of the rational use of native fruits by rural communities can contribute to local development.

21.5 Pequi pulp oil Generally to obtaining the oil from the pequi pulp two are mainly used two methods: extraction by cooking and extraction with solvents (Ribeiro, 2010). The extraction of oil from the pequi pulp by cooking consists mainly of an artisanal way, widely used by local communities, and produced in the middle of the forest, in fires lit with wood from the forest, in bonfires lit with wood from the forest. The extraction process is carried out under precarious conditions of hygiene and safety, and the process is very laborious. In this method, the fruits boil intensely, without the skin, for a prolonged period (Facioli & Gonc¸alves, 1998). Figueiredo et al. (1989) described that the oil comes off the fruit pulp during boiling, leaving the supernatant due to its low density and insolubility in water. However, the extraction process is very rudimentary, and the main disadvantages are its low yield, high-temperature requirements, and the fact that the oil is not filtered. According to Aquino (2007), to obtain approximately 2 L of pequi oil, 100 dozen fruit are needed. Due to the lack of storage space for the fruits and the exhaustive production cycle, obtaining 1 L of oil requires 10 hours of work, resulting in low production. However, researchers at EMBRAPA in 2020 (Brazilian Agricultural Research Corporation) presented a new methodology for extracting pulp oil more safely, quickly, and with a greater yield than the traditional scheme. The relatively simple method consists of removing the pulp, heating it in a water bath at 45 C, and centrifuging in equipment suitable for small agro-industries. Among the of this method advantages stands out the preservation of nutritional compounds sensitive to high temperatures, which would be lost during the long cooking traditionally used in production, superior yield because in the traditional method, the amount of oil extracted is less than 10% of the pulp mass, already the process presented by Embrapa obtains a 20% yield. Also, it is essential to highlight the reduction of environmental risk since extraction by centrifugation eliminates the furnaces made of wood from the forest.

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In the solvent extraction method developed by Aquino (2007), the fruits are first pulped with a stainless steel knife, and the pulps are taken to the greenhouse. After drying, the pulps are crushed until flour is obtained. Then, the obtained flour is placed in balloons next to the nonpolar solvent, and the extraction takes place by a batch system in an incubator in equipment that performs the Soxhlet method. Subsequently, the oil is filtered and taken to the oven to separate the solvent. The extraction process can be optimized by treating the raw material (cooking, rolling, drying), by selecting the most appropriate solvent or a mixture of solvents, and other operating conditions, for example, agitation, time, and extraction temperature. The quality of pequi oil, like that of vegetable oils, is directly related to several different factors, for example, type of processing, the form of storage, exposure to light and oxygen in the air, addition of adulterants (mixture with cheaper oils) heat and humidity. Besides, the oil content of the pequi pulp varies according to climatic and regional factors (cultivation area, altitude) and the extraction process. Pequi oil is yellow-orange (due to carotenoids) and has a very heterogeneous concentration of fatty acids. Thus, as the most relevant components, oleic, palmitic, linoleic fatty acids, and carotenoids can be mentioned. However, the pequi pulp oil’s main fatty acids are oleic and palmitic, 60% and 34%, respectively (Azevedo-Meleiro & Rodriguez-Amaya, 2004). It has a lower degree of unsaturation than other edible oils, and, consequently, it has better stability concerning oxidative rancidification. Oleic acid is a monounsaturated fatty acid and research reports that its beneficial activity is to reduce LDL cholesterol oxidation (Agibert & Lannes, 2018), thus contributing to the prevention of the development of heart diseases. Some studies demonstrate the beneficial effect of the application in the treatment of wounds, with the characteristic of forming a protective barrier against microorganisms and preventing tissue dehydration in addition to an essential immunomodulatory character (Ferreira et al., 2012). Carotenoids are natural antioxidants that can prevent or reduce oxidative damage since they can react with free radicals, presenting properties beneficial to health, acting mainly in the prevention of carcinomas, cardiovascular, ophthalmological, pulmonary, and neurodegenerative (Alo´s et al., 2016; Lima et al., 2012; Rao et al., 2007). The pequi pulp oil has a high content of carotenoids, and due to the significant instability of these compounds, that is, greater susceptibility to isomerization and oxidation, conditions during processing and storage must be controlled (Rodriguez-Amaya, 1993). For example, exposure of carotenoids to heat, oxygen, light, acidity, and low water activity are factors that can lead to structural changes, thus reducing their activity (Rodriguez-Amaya, 1993). In addition to carotenoids, pequi pulp oil is a source of vitamin C, phenolic compounds, and essential oils. All of these components have antioxidant properties, attenuating the effects of mutagens and carcinogens. The pequi pulp oil is used in the cosmetic industry in the production of soaps and creams for the skin; and also, in food (in the preparation of fried foods, manufacture of liqueurs and seasonings), due to their chemical properties and characteristic aroma. The general use, due to the teachings of ancient people, transmitting knowledge between generations, showed that pequi oil, in turn, has a traditional use for medicinal purposes, healing, and treatment, for example, of respiratory diseases, edema, ophthalmic problems related to low intake of vitamin A, and menstrual disorders (Ombredane et al., 2020).

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However, positive results from studies already carried out show that pequi pulp oil has several biological activities, such as antiinflammatory, antimicrobial, antioxidant, healing, antifungal, and reduction of cardiovascular problems. In humans, for example, there is already evidence to support the antiinflammatory, cardioprotective, and antigenotoxic effects. Animal research has also shown antioxidant, antiinflammatory, cardioprotective, hepatoprotective, antigenotoxic, and anticarcinogenic effects. Therefore, in-depth research must be carried out both in terms of chemical composition and pharmacological activity.

21.6 Biological activities of pequi pulp oil (Caryocar brasiliense Camb.) Studies show the effects of pequi oil in the prevention and treatment of cancer. Researchers at the Laboratory of Bioactive Compounds and Nanobiotechnology (LCBNano-FCE/UnB) at UnB to expand the possibility of using pequi oil for therapeutic purposes have used nanotechnology as a tool. Due to the hydrophobicity of pequi oil, there is a reduction in the possibilities of administration routes and interaction with cells and tissues. Therefore, Ombredane et al. (2020) used nanotechnology as a strategy to project and characterize a pequi oil-based nanoemulsion and estimate the anticarcinogenic effects. The results showed that pequi oil-based nanoemulsion could be considered to be used as a supporting breast cancer treatment tool. Colombo et al. (2015) found that pequi oil has the beneficial function of improving the defense system. The authors verified that this occurs due to the increase in the activity and expression of antioxidant enzymes, and, therefore, there is a reduction in oxidative stress and inhibition of the expression of transcription factors. Also, the results obtained also showed that pequi oil has the capacity to block the development of early lesions or inhibit the progression of cancer to an invasive form. According to the studies carried out by Miranda-Vilela et al. (2014), the use of pequi oil was able to contain tumor growth and increase immunity, additionally to reducing the side effects induced by chemotherapy. In the studies by Palmeira et al. (2015), the authors found that pequi pulp oil had a chemopreventive effect in mice subjected to preneoplastic liver induction lesions by the administration of carcinogenic diethylnitrosamine. The administration of pequi oil reduced the development of NLP and hepatic adenoma and made the remodeling of the lesions. The results found are probably related to the antioxidant compounds present in the oil. Thus, according to the findings, the authors report that the oil from the pequi pulp has the capacity to act in the preventive treatment of liver cancer. Carotenoids have a high antioxidant capacity, especially in conditions of low exposure to O2 (Gomes et al., 2005). Thus, supplementation with pequi oil can prevent oxidative damage induced by exercise for athletes who exceed their antioxidant defenses or who were born genetically less favored for the antioxidant defense system (Nascimento, 2018). According to the results obtained by Miranda-Vilela, Pereira, et al. (2009), MirandaVilela, Akimoto, et al. (2009), due to its diverse antioxidant content, many studies indicate that the use of pequi oil has anti-inflammatory properties. The authors evaluated the pequi pulp oil used to decrease inflammation caused by exercise and blood pressure and, in

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addition, modulate postprandial lipidemia in runners. This theory was tested by measuring blood pressure before the race; blood samples were collected after the races and subjected to analysis of leukocytes and platelets, highly sensitive C-reactive protein values, and postprandial lipids. According to the results obtained, the authors verified that the oil prevented the increase of lipid peroxidation and reduced the damage to DNA and tissues, as well as muscles, reduced liver damage markers significantly decreased total cholesterol and LDL cholesterol, increased HDL cholesterol, decreased blood pressure values, and showed antiinflammatory activity. Thus, pequi oil can be a good supplement for athletes. Bezerra et al. (2015) analyzed the use of pequi oil on skin lesions’ healing process in rats treated with topical oil use. For this, macroscopic and histopathological analysis of the healing process was performed until the 14th postoperative day. According to the results obtained, they verified that pequi oil has a beneficial role in the face of tissue repair. The authors were also able to note the decrease in inflammatory characteristics and the formation of new blood vessels when compared to the treated group compared to the control group, factors that contribute to accelerated wound repair in the treated rats. According to Vieira et al. (2019), phenolic compounds can act as antioxidants and fight free radicals and modulate the immune system’s activity, antimicrobial activity, and antiinflammatory action that favors the effectiveness of the healing process of injuries and ulcers. Nascimento et al. (2015) used pequi oil to heal the skin of incised and sutured rats and observed a significant influence on skin healing, producing more mechanical resistance of the injured tissue. The results were caused due to the increase in type I collagen synthesis, which allowed for scar repair in less time. Rabbers et al. (2019), incorporating pequi oil into collagen and gelatin membranes, found that the oil attenuated the inflammatory process in rats and stimulated more outstanding collagen production than membranes without pequi oil. The pequi pulp oil showed a chemopreventive effect in mice submitted to the induction of preneoplastic hepatic lesions using carcinogenic diethylnitrosamine. Aguilar (2010) in his study showed that pequi oil had a protective effect due to the antioxidant action of pequi in earlier stages of atherogenesis since the animals that consumed pequi oil had a lower percentage of lesion area in the aorta. The oil extracted from the pulp of C. brasiliense showed antibacterial activity through diffusion in a solid medium. The oil showed to be effective against strains of Pseudomonas aeruginosa ATTC27853 (Ferreira et al., 2011). Studies on antifungal oil activity (Passos et al., 2002) reduce inflammatory processes and blood pressure in runners (Miranda-Vilela, Pereira, et al., 2009; Miranda-Vilela, Akimoto, et al., 2009).

21.7 Final considerations Among the typical species of the Cerrado, Caryocar brasiliense Camb., or popularly, pequi, is commonly used by the local population, being considered by many as the king of the Cerrado. The pequi, indispensable in feeding the regional population, constitutes one of the main sources of income for the inhabitants of the serta˜o and the development of these regions. It provides part of the energy and nutritional inputs needed for healthy eating. Oil is extracted from the pulp of the fruit, which, in addition to cooking, is used in the

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References

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cosmetic industry in the production of soap, and its potential use in the pharmacological industry, because of its high antioxidant power. Through studies and research carried out, it is possible to verify that pequi pulp oil has numerous biological activities such as antiinflammatory, antimicrobial, healing, antifungal, and cardiovascular risk reduction. However, an in-depth research must be carried out with the aim of expanding knowledge regarding the chemical composition and biological activity of pequi oil.

21.8 Conclusion Pequi, traditionally found in Brazil, is an essential ingredient in regional cuisine, and the fruit is highly valued. Furthermore to the characteristic flavor, compounds extracted from the pequizeiro have been associated with the treatment of disease, the high concentration of lipids makes it a good source of energy, the presence of oleic acid is associated with the reduction of LDL cholesterol, in addition to high fiber content, vitamins and carotenoids in their composition. Given these characteristics, the consumption of pequi makes it a healthy option for the population. Its composition and the benefits it can present, associated with the disposal of various parts of pequi (bark, seeds), leaves and flowers, have aroused interest in research related to the extraction of constituents due to the possible benefits of its use as functional and nutraceutical ingredient. These compounds vary depending on climatic and regional issues and depending on the different extraction processes. The extraction process has also been the subject of research to improve it since it still proves to be rudimentary and not carried out industrially on a large scale. Thus, an extraction process that preserves nutritional and bioactive compounds, which are fast, low cost, and on a large scale, is of interest. The Nanotechnology is an area of great prominence in recent years in the food, pharmaceutical, and cosmetic industry, has also been used as a strategy to improve the use of various constituents found in pequi and thus reduce the limitations related to its application, making it with potential application for replacing synthetic antioxidants with antioxidants extracted from pequi, application as an anticancer compound, avoid oxidative stress, relieving the effects of chemotherapy and acting as antiinflammatories. Many studies must be carried out to improve the use of pequi and its constituents. However, despite the need for improvements in extraction and use as functional and nutraceutical ingredients, it represents an essential fruit in Brazilian cuisine.

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457. Machado, M. T. C., Mello, B. C. B. S., & Hubinger, M. D. (2015). Evaluation of pequi (Caryocar brasiliense Camb.) aqueous extract quality processed by membranes. Food and Bioproducts Processing, 95, 304
312. Magalha˜es, F. S., Sa´, M. S. M., Cardoso, V. L. C., & Reis, M. H. M. (2019). Recovery of phenolic compounds from pequi (Caryocar brasiliense Camb.) fruit extract by membrane filtrations: Comparison of direct and sequential processes. Journal of Food Engineering, 257, 26
33. Magalha˜es, H. G. (1988). Structural study of the pequizeiro Caryocar brasiliense Camb. Caryocaraceae, under the pharmacochemical and botanical aspect. Revista Brasileira de Farma´cia, 69(3), 31
41. Mendonc¸a, K. S., Correˆa, J. L. G., Junqueira, J. R. J., Cirillo, M. A., Figueira, F. V., & Carvalho, E. E. N. (2017). Influences of convective and vacuum drying on the quality attributes of Osmo-dried pequi (Caryocar brasiliense Camb.) slices. Food Chemistry, 224, 212
218. Miranda-Vilela, A. L., Akimoto, A. K., Alves, P. C. Z., Pereira, L. C. S., Gonc¸alves, C. A., Klautau-Guimara˜es, M. N., & Grisolia, C. K. (2009). Dietary carotenoid-rich pequi oil reduces plasma lipid peroxidation and DNA damage in runners and evidence for an association with MnSOD genetic variant -Val9Ala. Genetics and Molecular Research, 8, 1481
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858. Miranda-Vilela, A. L., Grisolia, C. K., Longo, J. P. F., Peixoto, R. C. A., de Almeida, M. C., Barbosa, L. C. P., Roll, M. M., Portilho, F. A., Estevanato, L. L. C., Bocca, A. L., Ba´o, S. N., & Lacava, Z. G. M. (2014). Oil-rich in carotenoids instead of vitamins C and E as a better option to reduce doxorubicin-induced damage to normal cells of Ehrlich tumor-bearing mice: Hematological, toxicological and histopathological evaluations. The Journal of Nutritional Biochemistry, 25(11), 1161
1176. Monteiro, S. S., Silva, R. R., Martins, S. C. S., Barin, J. S., & Rosa, C. S. (2015). Phenolic compounds and antioxidant activity of extracts of pequi peel (Caryocar brasiliense Camb.). International Food Research Journal, 22, 1985
1992. Nascimento, W. M., Filho, A. L. M. M., da Costa, C. L. S., Martins, M., & de Arau´jo, K. S. (2015). Study of skin scarring resistance of rats treated with pequi oil (Caryocar brasiliense). ConScientiaeSau´de, 14(3), 449
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962. Ombredane, A. S., Araujo, V. H. S., Borges, C. O., Costa, P. T., Landim, M. G., Pinheiro, A. C., Szlachetka, I. O., Benedito, L. E. C., Espindola, L. S., Dias, D. J. S., Oliveira, D. M., Chaker, J. A., da Silva, S. W., de Azevedo, R. B., & Joanitti, G. A. (2020). Nanoemulsion-based systems as a promising approach for enhancing the antitumoral activity of pequi oil (Caryocar brasiliense C.) in breast cancer cells. Journal of Drug Delivery Science and Technology, 58, 101819. Palmeira, S. M., Silva, P. R. P., Ferra˜o, J. S. P., Ladd, A. A. B. L., Dagli, M. L. Z., Grisolia, C. K., & HernandezBlazquez, F. J. (2015). Chemopreventive effects of pequi oil (Caryocar brasiliense Camb.) on preneoplastic lesions in a mouse model of hepatocarcinogenesis. European Journal of Cancer Prevention, 25(4), 299
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1.793. Sousa, A. G. O., Fernandes, D. C., Alves, A. M., Freitas, J. B., & Naves, M. M. V. (2011). Nutritional quality and protein value of exotic almonds and nut from the Brazilian Savanna compared to peanut. Food Research International, 44, 2319
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C H A P T E R

22 Biological activities of Allanblackia (Allanblackia parviflora) oil Siti Nurulhuda Mastuki1,4, Siti Munirah Mohd. Faudzi1,2, Norsharina Ismail1 and Norazalina Saad3 1

Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 2Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 3UPM - MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 4Department of Biological Sciences and Biotechnology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi, Selangor, Malaysia

Abbreviations DPPH GCMS MIC Rf SEO SPO

2, 2-Diphenyl-1-picrylhydrazyl gas chromatography
mass spectrometry minimum inhibitory concentration retention factor solvent extraction oil screw press oil

22.1 Introduction Allanblackia species originate from the Guttiferae family and Clusiaceae subfamily. The nine species of Allanblackia genus which native to tropical Africa (extending from Sierra Leone to Tanzania regions) including; A. gabonensis (Pellegr.) Bamps, A. floribunda Oliv., A. kimbiliensis Spirl, A. kisaonghi Vermoesen, A. marienii Staner, A. parviflora A. Chevalier, A. stanerana Exell & Mendonc¸a, A. stuhlmannii Engl., and A. ulugurensis Engl. (Bamps et al., 1978). Among these, A. paviflora, A. floribunda, A. stuhlmannii, and A. ulugurensis are well recognized due to their valuable uses in oil, soap, functional food and cosmeceuticals industries. A. parviflora, commonly known as the vegetable Tallow tree or Sonkyi, is

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00018-0

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FIGURE 22.1 The distribution of Allanblackia parviflora (Wikimedia Commons, 2020a). Source: From Wikimedia Commons. (2020a). Blank map World.png - Wikimedia commons. Wikimedia Commons. Available from https://commons.wikimedia.org/wiki/File:BlankMap-World-noborders.png).

greatly used as traditional herbal medicines by the local community. This wild dioecious and uncultivated fruit tree is distributed from the humid forest of Guinea, Sierra Leone, Liberia, Cote Dı´voire, and Ghana (Rompaey, 2003) (see Fig. 22.1). Not only in the forest, A. parviflora was also found as the primary species in cocoa-growing areas of Ghana, providing shades for the cocoa trees (Peprah et al., 2009). This oil-rich tree often misidentified as A. floribunda, but can be distinguished by its distribution area where the A. floribunda usually found in Benin and Nigeria east regions to Congo and Angola area (Adubofuor et al., 2013). Further discrimination can be determined from the botanical morphologies, in which A. parviflora male flower has smooth glands with short pedicels, in comparison to A. floribunda with folded disk glands and longer pedicels (Orwa & Oyen, 2007).

22.2 Ethnobotany 22.2.1 Vernacular names Allanblackia was found and named after Allan Black, a botanist from Scotland. Besides being generally known as the vegetable Tallow tree, due to its oil content, A. parviflora also called kagna butter or mkanyi fat (FAO, 2014). It has various vernacular names influenced by many regions, including Sonkyi (Brong Ahafo), Atrodua (Eastern of Ghana), Sonkyi, Osono dukono, Kusie adwe, Kusie aduane, Dufufui, Akosobolo, Krupi, and Bohe (Western of Ghana), and Sonkyi (Ashanti) (Siaw et al., 2003). According to folklore, the Kusie aduane represents the meaning of rat (kusie) and food (aduane), which is believed

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22.2 Ethnobotany

to be the “emergency” food for the wild rat and porcupines during the drought and deprivation seasons. Meanwhile, the plant was named Osono dukono, bringing the meaning of elephant kenkey (a local staple food) presumably explained by the large size of A. parviflora fruit that resembles the shape of kenkey balls (Antwi et al., 2014; Kwasi et al., 2016).

22.2.2 Botanical description A. parviflora grows between 25 and 30 m tall, with 80 cm of trunk diameter (see Fig. 22.2). The outer layer of bark described as yellow or red-brown in color with small irregular scales. Meanwhile, the inner layer consists of yellow streaks on the reddish-brown color bark with colorless sap. It composes of either blade elliptical or narrowed obovate (12
25 cm long 3 5
9 cm width) shape leaves, with 1
1.5 cm petiole (see Fig. 22.3). The A. parviflora flowers are approximately 2 cm in length, consist of five pink or red fragrant petals and green ovate or obovate unequal sepals with 6
18 mm 3 4
15 mm in size. Opposite the petals, the five obtriangular stamens attached to star-formed disk with smooth or slightly folded glands. On the other hand, the fruit is huge and identified as a ripe brown ellipsoid berry with a 10
50 cm range size that consists of approximately 40
100 embedded seeds in the pink pulp (Orwa & Oyen, 2007). Up to 300 fruits can be produced by a single A. parviflora tree and the seeds are extracted from the fallen fruits and leave to dry. Approximately ten fruits are needed to yield 3.0 kg of dried seeds, and about 1/3 (weight/weight; w/w) of oil is yielded from that sun-dried seed (Pye-Smith, 2009). FIGURE 22.2 Allanblackia parviflora tree (Wikimedia Commons, 2019). Source: From Wikimedia Commons. (2019, December 20). Category: Allanblackia parviflora Wikimedia commons. Wikimedia Commons. Available from https://commons.wikimedia.org/ wiki/Category:Allanblackia_parviflora.

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22. Biological activities of Allanblackia (Allanblackia parviflora) oil

FIGURE 22.3 Allanblackia parviflora leaves (Wikimedia Commons, 2020b). Source: From Wikimedia Commons. (2020b, October 9). File:Allanblackia parviflora nursery.jpg - Wikimedia Commons. Wikimedia Commons. Available from https:// commons.wikimedia.org/wiki/File: Allanblackia_parviflora_nursery.jpg.

22.3 Nutritional and chemical compositions of Allanblackia parviflora 22.3.1 Nutritional and chemical compositions of Allanblackia parviflora oil In general, the Allanblackia sp. seeds compose of approximately 67%
73% oil. The oil is characterize as white fat at room temperature and its components were dominated by the stearic and oleic acids (Sefah, 2018), suitable for margarine and cosmetic productions, hence generate industrial and consumer interests over times. Adding to its nutritional values, both essential fatty acids were documented to reduce the risk of heart attack by lowering the plasma cholesterol (Atangana et al., 2011). Remain as the only species of Allanblackia in the Ghana region with growing evidence of nutritional benefits, A. parviflora seed oil has become the main focus in a project called “Novella African Project,” initiated by the corporate company (Unilever Public Limited Company), research institutes, nongovernment organizations (NGO) and local farmers (Buss & Tissari, 2010). This novel project was firstly developed to produce high-quality functional foods include vegetables-based dairy, ice cream and bread spread products of the household. The oil usually extracted from the seeds powder using the manual compress method at the minimum temperature, to protect the bioactive compounds in seeds oil from the degradation process (Nederal et al., 2012). Research on A. parviflora oil began as early as the year 1940, revealed that stearic acid and oleic acid are the most abundant components at 52% and 43.9% respectively, showing a similar component ratio as in A. floribunda (Meara & Zaky, 1940). Whilst, fatty acids composition analysis reported the content of myristic acid, palmitic acid and arachidonic acid at the minimum percentage of 1.5%, 2.3%, and

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0.2% only. This study as well discovered 2-oleostearin (60.1%) as the domain triglyceride, followed by the 1-stearo-diolein (26.9%), and 2-oleopalmitostearin (6.9%). On the other note, Adubofuor et al. (2013) have determined the nutrient and chemical compositions of A. parviflora seed oil and kernel collected from New Edubease, Ashanti, Ghana, in comparisons with palm kernel and oil. The seeds sample was divided into two groups distinguished by their oil extraction methods. The screw press oil (SPO) group was obtained via 2 hours of the mechanical extraction process, meanwhile the solvent extraction oil (SEO) group was soaked in petroleum ether underwent an extraction process for 16 hours. The fatty acid compositions were determined through gas chromatography, and reported considerable discrimination variation of fatty acids profile in A. parviflora seed oil in comparison with other oils. The results indicated that the most abundant fatty acids in A. parviflora seed oil were stearic acid (45%
58%) and oleic acid (40%
51%), relatively higher than the palm oil (stearic acid; 1%
8% and oleic acid; 26%
52%) and palm kernel oil (stearic acid; 1%
3% and oleic acid; 10%
23%). In contrast, A. parviflora seed oil consists minor components of palmitic acid (0%
2%), myristic acid (0%
1%) and lauric acid (0%
1%). These findings are parallel with previous data (Meara & Zaky, 1940; Orwa & Oyen, 2007). Even though A. parviflora seed oil is a stearic acid-rich component, this saturated fatty acid is highly unique unlike other saturated fatty acids (more than 10 carbon chains). Stearic acid was demonstrated to has no effects on blood total, low density cholesterol (LDL) and high density cholesterol (HDL) levels, as well as associated with low risk of cardiovascular diseases (Adubofuor et al., 2013). However, despite its potential nutritional values, there is limited information on phytochemicals profile of A. parviflora seed oil. On the same note, Adubofuor et al. (2013) indicated the carotenoids, terpenes, saponins, and tannins were not present or low in quantities to be detected in both samples of SPO and SEO of the oil-of-interest. As A. parviflora often mistaken as A. floribunda, similar results were expressed in another study performed by Dike and Asuquo (2012), reported that saponin and tannin component were found in very minimum amount as in A. floribunda oil.

22.3.2 Nutritional, mineral, and chemical compositions of Allanblackia parviflora seeds The proximate composition of A. parviflora seeds showed relatively high crude fat and energy compositions at 67% and 2863.4 kJ/100; significantly higher than the shea kernel and cocoa beans (Ugese et al., 2010). Therefore explaining its traditional usage as an energy-boosting snack among Africa children (Orwa & Oyen, 2007). These seeds were also reported low in moisture (3.4%), protein (4.27%), ash (1.98%), crude fiber (5.7%), and moderate level of carbohydrates (17.06%) (Adubofuor et al., 2013). In further research, reports revealed the same pattern in the mineral content of A. parviflora seeds, where mean values of sodium (5.24 mg/kg), copper (0.04 mg/kg), manganese (0.13 mg/kg), and calcium (0.10 mg/kg) were low in comparison with the shea kernels. Apart from that, both phosphorus and potassium levels were detected higher in A. parviflora seeds at 8.34 and 8.41 mg/kg, respectively, exceeding the shea kernel composition level (Adubofuor et al., 2013; Alhassan et al., 2011).

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Phytochemicals are defined as a chemical substance produced by plants that provide desirable health benefits against certain diseases through their biological activities (Jimenez-Garcia et al., 2018). In more recent years, Sefah, Sefah, and Ofori (2020) studied the phytochemicals of A. parviflora seeds from 16 various regions in Ghana. They have specifically collected fruit samples from the moist semi deciduous forest (New Edubeasem Adansi Akrofuom, Fenaso, Anwonam Afosu, Atwereboanna, Akoase, and Wassa Akropong), moist-evergreen areas (Daboase, Sefwi Bodi, Samreboi, and Benso) and wet evergreen areas (Kwansima, Asont, Banso, and Nzema Akropong) on December 2014 and April 2015. The extracted seeds were sun-dried for 7 days to reduce 10% of moisture and milled to obtain a 1.18 mm particle size. Under this research, the optimal experimental condition was determined as; approximately 2.0 g sample was extracted twice in methanol-water (80:20 v/v) for 30 min, and HPTLC mobile phase of ethyl acetate: methanol: water at the ratio of (100:16, 5:13.5 v/v) with 7 minutes of plate heating period treated with vanillic acid for derivatization. The phytochemical profiling disclosed similar key bands at 0.12, 0.35, and 0.39 retention factors (Rfs) monitored at 254 nm wavelength. Consistent data also reported at 366 nm wavelength for the derivatized samples, replications of all different region samples demonstrated no intense band variations at 0.12, 0.29, 0.37, and 0.4 Rf, indicating that the extraction and separation methods optimized are robust and reproducible. Even though key bands of A. parviflora seeds were successfully detected in this particular research, there is no bioactive secondary metabolites have been isolated and reported to date.

22.3.3 Chemical compositions of Allanblackia parviflora leaves Onilimor (2016) has conducted works to determine the phyto-constituents of A. parviflora leaves cultivated in Afosu, Ghana. The respective plant part was undergoing 14 days of air drying prior to 72 hours of maceration extraction using methanol, water and petroleum ether solvents to yielded 14.4%, 2.21%, and 6.52% (w/w) of crude extract, respectively. The reported phytochemicals including flavonoids, tannins, reducing sugars, glycosides, terpenoids, anthraquinones, and cardiac glycosides in methanolic crude extract. The aqueous crude extract had similar phytochemical contents as the methanolic crude extract with additional alkaloids-class of metabolites. Nonetheless, data revealed that petroleum ether was only composed of the reducing sugars, glycosides, terpenoids, and cardiac glycosides. This research was the first one to published with regards to phytochemicals of A. parviflora leaves and no further isolation and characterization of bioactive components reported in any reports thus far.

22.3.4 Chemical compositions of Allanblackia parviflora stem Despite a growing number of researches performed on A. parviflora, there is limited information available on phytochemical constituents of A. parviflora stem. Nonetheless, to date, the first bioactive compounds screening from stems were described by Kwasi et al. (2016). Samples were obtained from several farms in Afosu of Ghana, cut, washed and airdried for 14 days at room temperature before milled into fine particles. Samples were

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subjected to 72 hours of solvent extraction via the cold maceration technique using methanol, petroleum ether and distilled water, to produced 7.3%, 6.52%, and 2.21% of crude extracts, respectively. They have mentioned all samples were qualitatively screened for the presence of secondary metabolite classes such as tannins, flavonoids, reducing sugar, saponins, triterpenoids, phytosterol, anthraquinones, general alkaloids, cardiac glucosides, and cyanogenic glycosides. Among these classes, the reported data showed that methanolic crude extract was enriched with listed phytochemicals except for cardiac glucosides and cyanogenic glycosides. Likewise, the aqueous crude extract showed similar secondary metabolites to the pulverized sample. However, saponins, phytosterol, and cyanogenic glycosides groups were not detected in both samples. On the other hand, petroleum ether crude extracts consisted of tannins, reducing sugars and cardiac glucosides only. The different of phyto-constituents in the respective extracts may be attributed to the polarity factor of secondary metabolites embedded in the stem. Most chemical components are higher in polarity by nature, hence insoluble in nonpolar solvents such as petroleum ether.

22.4 Biological activity of Allanblackia parviflora A. parviflora has been claimed to possess therapeutic values, supporting the traditional uses of this plant in treating various diseases. The leaves either were chewed to alternatively treat respiratory illnesses such as asthma and chronic bronchiolitis or were taken as an infusion for chest pain treatment (Chevalier, 1905). Meanwhile, in Coˆte d’Ivoire region, the fruit pulp of A. parviflora decoction was used to reduces scrotum elephantiasis (Orwa & Oyen, 2007). Notwithstanding the traditional evidence, none have described the complete phytochemicals composition and pharmacological properties of A. parviflora seed oil. Nevertheless, being similar to A. parviflora, numerous data have shown the pharmacological potential of A. floribunda seed oil as an antihypertension and antioxidant agent (Bilanda et al., 2010; Crockett, 2015; Srivastava et al., 2021). On another plant part, Onilimor (2016) has focused on and screened the antimicrobial activity of A. parviflora leaves. The respective plant part was collected from the Afosu region of Ghana and allowed to room temperature air-dried for 14 days prior to pulverization and 72 hours’ maceration of diverse solvent extraction (methanol, aqueous, and petroleum ether). Antimicrobial testing was conducted using agar well diffusion and broth dilution method against various microorganisms including nine bacteria (Staphylococcus aureus; ATCC25923, Enterococcus faecalis; ATCC29212, Bacillus subtillis; ATCC10073, Streptococcus pyogenes; clinical strain, Eschariccia coli; ATCC25922, Klebsiella pneumonia; clinical strain, Pseudomonas aeruginosa; ATCC4853, S. paratyphi A; clinical strain, and Neisseria gonorrhoea; clinical strain) and a fungus (Candida albican; clinical strain). The aqueous extracts exerted the highest antimicrobial activity in C. albicans with 15.75 mm of inhibition zone and minimum inhibitory concentration (MIC) value at 20.00 mg/mL; followed by K. pneumonia (13.75 mm), P. aeruginosa (13.50 mm), and S. aureus (13.50 mm). Meanwhile, the methanol extract demonstrated moderate antimicrobial activity on S. aureus (12.00 mm), S. pyogenes (11.00 mm), and both E. coli and S. paratyphi A (10.75 mm). Interestingly, less polarity extract of petroleum ether was insignificantly active against all tested microorganisms.

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Kwasi et al. (2016) have examined the potential of stem bark of A. parviflora for antimicrobial activity. The findings revealed that the methanolic stem extracts actively inhibited the E. faecalis, S. aureus, and C. albicans growth at 20.0 mm, 17.5 mm, and 17.0 mm of diameters, respectively, in comparison to the standard control, ciprofloxacin (E. faecalis; 16.0 mm, S. aureus; 21.5 mm, and C. albicans; 21.5 mm). These noteworthy results are in-line with the traditional claims of A. parviflora usage in treating tooth and chronic bronchial infections, as E. faecalis, S. aureus, and C. albicans were known related to tooth and respiratory pathogens. Meanwhile, aqueous stem extracts showed notable inhibition in E. faecalis (15.0 mm) and S. aureus (15.0 mm), whereas the petroleum ether was found inactive against all microorganisms. A. parviflora leaves extracts were also tested for their antioxidant potential using the 2,2diphenyl-1-picrylhydrazyl (DPPH) radical scavenge assay. Results demonstrated that all extracts were able to scavenged the DPPH free radicals in a concentration-dependent manner (Onilimor, 2016). The results showed the methanolic leaves extract with the lowest 50% maximum inhibitory concentration (IC50) at 48.97 μg/mL, suggesting the highest antioxidant capacity when compared to the positive reference, ascorbic acid at IC50 value of 29.91 μg/mL. Contrarily, both aqueous and petroleum ether leaves extracts exhibited IC50 values at 158 μg/mL and 1479 μg/mL, respectively. On the same data, the antiinflammatory activity of the same leaves extracts was first evaluated via in vivo carrageenaninduced paw edema model in seven days old of chicks (Onilimor, 2016). Briefly, 10 μL of 2% carrageenan was injected into the chick’s left footpad for edema induction. Extracts were administered via oral route at different concentrations (30, 100, and 300 mg/kg). The foot volume was measured using a digital clipper at various time points during both prophylactic and therapeutic analyses. Prophylactic is defined as a process of guarding or preventing the occurrence of a specific disease by the introduction of drug/treatment before the onset of disease, while if the drug/treatment is administered after the disease occurred, it can be considered as therapeutic (Da Silva & Willmore, 2012). In this work, the administration of A. parviflora leaves extracts was given an hour before inflammation induction. Generally, the diclofenac (positive reference) and A. parviflora leaves extracts showed significant concentration-dependent activity on the inflammation reduction. The highest percentage inhibition of edema was recorded in the methanolic extract group with 57.2% (P , 0.001) at 300 mg/kg of dosage, whereas slightly lower inhibitions were determined in the aqueous and petroleum ether (50.9% and 50.12%) based on the therapeutic analyses. Meanwhile, in terms of before onset of action, the effects of dose-dependent were successfully observed in all extracts, as an example, the aqueous extract in the prophylactic analysis had the inhibition percentage of 25.4% (30 mg/kg), 30.0% (100 mg/kg), and 52.3% (300 mg/kg), respectively. A similar dose-dependent manner was recognized in diclofenactreated group with data of prophylactic analyses of 65.8% (30 mg/kg), 70.3% (100 mg/kg), and 77.8% (300 mg/kg), respectively. Onilimor (2016) described the methanolic leaves extract exerted better action as curative (300 mg/kg; P , 0.001) than preventive (300 mg/kg; P , 0.01). This potent activity was the first report published for A. parviflora leaves. Even though A. parviflora has been under a high degree of attention for its nutritional values and commercialization exploitation, their medicinal evidence over the folklore claims are not well-proven just yet. The specific mechanisms underlying the screened events such as antimicrobial, antioxidant and antiinflammatory activities are still remained unknown especially on the main A. parviflora product, the oil. Thus further in-depth

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research on the isolation and characterization of potential bioactive compounds with welldesigned pharmacological tests are required to unlock the hidden potential of A. parviflora.

References Adubofuor, J., Sefah, W., & Oldham, J. H. (2013). Nutrient composition of Allanblackia paviflora seed kernels and oil compared with some plant fats and oils and application of the oil in soap preparation. Journal of Cereals and Oil Seeds, 4(1), 1
9. Alhassan, E., Agbemava, S. E., Adoo, N. A., Agbodemegbe, V. Y., Bansah, C. Y., Della, R., Appiah, G. I., Kombat, E. O., & Nyarko, B. J. B. (2011). Determination of trace elements in Ghanaian shea butter and shea nut by neutron activation analysis (NAA). Research Journal of Applied Sciences, Engineering and Technology, 3(1), 22
25. Antwi, K., Effah, B., Adu, G., & Adu, S. (2014). Strength and some physical properties of Allanblackia parviflora for furniture production in Ghana. IJST, 4(1), 1
8. Atangana, A. R., Van Der Vlis, E., Khasa, D. P., Van Houten, D., Beaulieu, J., & Hendrickx, H. (2011). Tree-to-tree variation in stearic and oleic acid content in seed fat from Allanblackia floribunda from wild stands: Potential for tree breeding. Food Chemistry, 126(4), 1579
1585. Available from https://doi.org/10.1016/j.foodchem.2010.12.023. Bamps, P., Robson, N., & Verdcourt, B. (1978). Flora of tropical East Africa: Guttiferae. Crown Agents for Overseas Governments & Administrations. Bilanda, D. C., Dimo, T., Dzeufiet Djomeni, P. D., Bella, N. M. T., Aboubakar, O. B. F., Nguelefack, T. B., Tan, P. V., & Kamtchouing, P. (2010). Antihypertensive and antioxidant effects of Allanblackia floribunda Oliv. (Clusiaceae) aqueous extract in alcohol- and sucrose-induced hypertensive rats. Journal of Ethnopharmacology, 128(3), 634
640. Available from https://doi.org/10.1016/j.jep.2010.02.025. Buss, C. & Tissari, J. (2010). Allanblackia
An ingredient for poverty reduction? In Rural 21 international platform. Available from https://www.doc-developpement-durable.org/file/Arbres-Bois-de-Rapport-Reforestation/ FICHES_ARBRES/Allanblackia/Allanblackia_aningredientforpovertyreduction_Rural21.pdf. Chevalier, A. (1905). Les ve´ge´taux utiles de l’Afrique tropicale franc¸aise. Archives de parasitologie (Vol. 1). De´pot des publications. Available from https://books.google.com.my/books/about/Les_ve´ge´taux_utiles_de_l_Afrique_tropi. html?id 5 S3XfxwEACAAJ&redir_esc 5 y. Crockett, S. (2015). Allanblackia oil: Phytochemistry and use as a functional food. International Journal of Molecular Sciences, 16(9), 22333
22349. Available from https://doi.org/10.3390/ijms160922333. Da Silva, A. M., & Willmore, L. J. (2012). Posttraumatic epilepsy, . Handbook of clinical neurology (Vol. 108, pp. 585
599). Elsevier B.V. Available from https://doi.org/10.1016/B978-0-444-52899-5.00017-4. Dike, M. C., & Asuquo, M. E. (2012). Proximate, phytochemical and mineral compositions of seeds of Allanblackia floribunda, Garcinia kola and Poga oleosa from Nigerian rainforest. African Journal of Biotechnology, 11(50), 11096
11098. Available from https://doi.org/10.5897/ajb11.4054. FAO. (2014). Minor oil crops
Individual monographs (Allanblackia-Almond). Available from http://www.fao.org/ docrep/x5043e/x5043e0d.htm. Jimenez-Garcia, S. N., Vazquez-Cruz, M. A., Garcia-Mier, L., Contreras-Medina, L. M., Guevara-Gonza´lez, R. G., Garcia-Trejo, J. F., & Feregrino-Perez, A. A. (2018). Phytochemical and pharmacological properties of secondary metabolites in berries. In A. M. Holban, & A. M. Grumezescu (Eds.), Therapeutic foods (pp. 397
427). Academic Press. Available from https://doi.org/10.1016/b978-0-12-811517-6.00013-1. Kwasi, A. J., Eunice, A., Isaac, A., Samuel, O.-D., & Jagri, P. (2016). Phytochemical screening and antimicrobial activities of the stem bark of Allanblackia parviflora Chev. (Clusiaceae). The Journal of Phytopharmacology, 5(Issue 6), http://www.phytopharmajournal.com. Meara, M. L., & Zaky, Y. A. H. (1940). Fatty acids and glycerides of the seed fats of Allanblackia floribunda and Allanblackia parviflora. J. Soc. Chem. Ind, 59, 25
26. ˇ Nederal, S., Skevin, D., Kralji´c, K., Obranovi´c, M., Papeˇsa, S., & Bataljaku, A. (2012). Chemical composition and oxidative stability of roasted and cold pressed pumpkin seed oils. JAOCS, Journal of the American Oil Chemists’ Society, 89(9), 1763
1770. Available from https://doi.org/10.1007/s11746-012-2076-0. Onilimor, P.J. (2016). Phytochemical screening, antimicrobial, antioxidant and anti-inflammatory activities of methanolic, aqueous and pet ether extracts of the leaves of Allanblackia parviflora (A. Chevalier). Kwame Nkrumah University of Science and Technology. Available from http://dissertation.com/abstracts/2101297.

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Orwa, C., & Oyen, L. P. A. (2007). Allanblackia parviflora A. Chev. In H. A. M. Van Der Vossen, & G. S. Mkamilo (Eds.), Plant resources of tropical Africa 14 vegetable oils. PROTA Foundation (pp. 28
30). Backhuys Publishers. Peprah, T., Ofori, D. A., Siaw, D. E. K. A., Addo-Danso, S. D., Cobbinah, J. R., Simons, A. J., & Jamnadass, R. (2009). Reproductive biology and characterization of Allanblackia parviflora A. Chev. in Ghana. Genetic Resources and Crop Evolution, 56(7), 1037
1044. Available from https://doi.org/10.1007/s10722-009-9475-6. Pye-Smith, C. (2009). Seeds of hope: A public-private partnership to domesticate a native tree Allanblackia, is transforming lives in rural Africa. Rompaey, R.V. (2003). Distribution and ecology of Allanblackia spp. (Clusiaceae) in African rain forests with special attention to the development of a wild picking system of the fruits. Available from http://www.rbgkew.org.uk/peopleplants/wp/wp4/bwindi.htm. Sefah, W. (2018). Spatial variation of Allanblackia parviflora seed products in Ghana: Chemical and ethnobotanical exploration. Theses: Doctorates and Masters. Available from https://ro.ecu.edu.au/theses/2098. Sefah, W., Sefah, L., & Ofori, H. (2020). Development of a HPTLC method to profile the phytochemicals in Allanblackia parviflora (tallow tree) kernel and seed cakes. Journal of Planar Chromatography - Modern TLC, 33(1), 33
41. Available from https://doi.org/10.1007/s00764-019-00009-9. Siaw, D.E.K.A., Cobbinah, J.R., Kankam, B.O., Derkyi, S.A., Oduro, K.A., Agyili, J., & Peprah, T. (2003). Final report on Allanblackia floribunda.Novella Project, Submitted to Unilever Ghana Ltd. by Forestry Research Institute of Ghana. Srivastava, Y., Semwal, A. D., & Dhiman, A. (2021). A comprehensive review on processing, therapeutic benefits, challenges, and economic scenario of unconventional oils. Journal of Food Processing and Preservation, e15152. Available from https://doi.org/10.1111/jfpp.15152. Ugese, F. D., Baiyeri, K. P., & Mbah, B. N. (2010). Proximate traits of the seed and seed cake of shea butter tree (Vitellaria paradoxa C. F. Gaertn.) in Nigeria’s savanna ecozone. Journal of Applied Biosciences, 31, 1935
1941. https://www.cabdirect.org/cabdirect/abstract/20113087828. Wikimedia Commons. (2019, December 20). Category: Allanblackia parviflora - Wikimedia commons. Wikimedia Commons. Available from https://commons.wikimedia.org/wiki/Category:Allanblackia_parviflora. Wikimedia Commons. (2020a). Blank map World.png - Wikimedia commons. Wikimedia Commons. Available from https://commons.wikimedia.org/wiki/File:BlankMap-World-noborders.png. Wikimedia Commons. (2020b, October 9). File:Allanblackia parviflora nursery.jpg - Wikimedia Commons. Wikimedia Commons. Available from https://commons.wikimedia.org/wiki/File:Allanblackia_parviflora_nursery.jpg.

Multiple Biological Activities of Unconventional Seed Oils

C H A P T E R

23 Biological activities of pistachio (Pistacia vera) oil Norsharina Ismail1, Kim Wei Chan1, Siti Nurulhuda Mastuki1, Norazalina Saad2 and Ahmad Faizal Abdull Razis1 1

Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia 2UPM - MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

Abbreviations DPPH FTIR Ifit-2 NFKB PCOS PEGNLPUOs

2, 2-diphenyl-1-picrylhydrazyl Fourier transform infrared INF-induced protein with tetratricopeptide repeats 2 nuclear factor kappa-light-chain-enhancer of activated B polycystic ovary syndrome PEGlated nanoliposome of pistachio unsaturated oils

23.1 Introduction Nuts are promoted as an essential health food in human societies all over the world. Various kinds of nuts, including the pistachio nut (Pistacia vera L.), are eaten raw or toasted unsalted or salted besides being used as food ingredients. The pistachio nut has distinctive organoleptic characteristics as well as a high nutritious value. It contains a lot of fat, mostly monounsaturated fatty acids, vitamins, minerals, and bioactive components like tocopherols, sterols, and phenolics (Yahyavi, Alizadeh-Khaledabad & AzadmardDamirchi, 2020). The pistachio nut was rated one of the top 50 foods with the most antioxidant potential, thus it can be considered to be a functional food (Halvorsen et al., 2006). According to the Dietary Guidelines, eating nuts such as pistachios, hazelnuts, walnuts, almonds, pecans, and peanuts on a daily basis is beneficial to human wellbeing (John & Shahidi, 2010). Depending on its origin, pistachio oil contains a number of unsaturated fatty

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© 2022 Elsevier Inc. All rights reserved.

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23. Biological activities of pistachio (Pistacia vera) oil

acids, including oleic and linoleic acids. Additionally, it encompasses greater amounts of natural antioxidants, namely phenolics with notable source of phytosterols and tocopherols in comparison to other nut oils. To produce a high-grade product, the extraction process, including drying and roasting, should be carefully controlled (Catala´n et al., 2017).

23.1.1 Pistacia vera plant description and distribution The pistachio nut (Pistacia vera L.) is a valued crop and the only edible commercial plant in the Anacardiaceae family. The pistachio kernel is a drupe that is semidry with a single edible pod, coated by a thin soft layer of testa, surrounded by endocarp with a lignified, creamy shell, and enclosed by mesocarp and epicarp, a green to yellow-red colored fleshy ¨ stu¨ndag, ˘ Carle & Schweiggert, 2016). hull, based on the state of ripeness (Er¸san, Gu¨c¸lu¨ U Fig. 23.1 depicts a pistachio tree, fruits, kernels, and shells. The largest pistachio farmers are Iran, followed by the United States, Turkey, Syria, Greece, Italy, and Spain, with the pistachio nut serving as an important agricultural commodity (Rodrı´guez-Bencomo et al., 2015). Turkish varieties are favored in European and American marketplaces due to their superior flavor and more uniform green kernels, despite their smaller shell and kernel sizes when compared to Iranian and American varieties (¸Sahan & Bozkurt, 2020). Because of their nutritive and pleasing sensory properties, plant-derived oils have seen industry rise due to increasing use and demand for novel edible oils (Salvador, OjedaAmador & Fregapane, 2019). Depending on geographic area, crop year, and cultivar, the pistachio kernel oil content differs from 50% to 60% by dry weight. Despite the fact that the Codex Alimentarius on Fats and Oils has not set specific standards for pistachio oil, it is believed to be a niche product (Tsantili et al., 2010; Ojeda-Amador, Fregapane & Salvador, 2018). Pistachio oil has gained global attention due to its high antioxidant capacity displayed by health promoting compounds (Martorana et al., 2013), as well as its unique organoleptic characteristics (Acen˜a, Vera, Guasch, Busto & Mestres, 2010). The majority of pistachio

FIGURE 23.1 Pistachio (Pistacia vera) tree and fruits (A); pistachio shells and kernels (B); pistachio shells (C). Source: https://commons.wikimedia.org.

Multiple Biological Activities of Unconventional Seed Oils

23.2 Pistacia vera chemical composition

281

by-products are from leaves, green hull, residual kernel, clusters, and hard woody shell (Mohammadi Moghaddam, Razavi, Malekzadegan & Shaker Ardekani, 2009).

23.2 Pistacia vera chemical composition Variety, growing origin, and climate are factors that affect the pistachio nut quality (Yahyavi et al., 2020). The fatty acids and terpenes, which are the key compounds accountable for pistachios’ nutritious and sensory properties, are affected by the microclimate in pistachio kernels (Polari, Zhang, Ferguson, Maness & Wang, 2019). Pistachio production in Australia, for example, has been affected by a series of cold winters, resulting in late bloom and crop reduction (Ranford & Zhang, 2018). The discovery of variants and their sources, on the other hand, is crucial in ensuring ´ lvarez-Ortı´, Go´mez, de Miguel, & these nut oils’ commercial future prospects (Rabada´n, A Pardo, 2018). Wild and cultivar pistachio nuts varied greatly in physical and pomological properties, but there was less variance in oil content and nutritional composition (Pourian, Bakhshi, Hokmabadi & Aalami, 2019). Despite considerable variability in pistachio oil due to crop year interaction with genotype, genotype remains a major factor determining oil chemometrics. Nonetheless, the crop year had an impact on certain minor nutritional components, such as total polyphenols and phytosterols. Finally, for oil extraction, some pistachio genotypes should be given priority. During programs for breeding, chemical parameters primarily determined by genotype should be concentrated on improving particular features of pistachio oil (Rabada´n et al., 2018). Bioactive compound variations, such as fatty acid composition, tocopherol content, and phenolic compounds, are influenced by extraction processes. The oleic acid contents were found higher when extracted by cold pressed oils in comparison to soxhlet extraction. The cold press extraction system avoids the damage of compounds that are sensitive to heat, thus may preserve the important nutrients and improve its bioactive contents. Furthermore, systems for extracting oil that use less hazardous organic solvents are advantageous. Cold pressing processes, for example, avoid the use of heat and organic solvents, making this technique a cost-effective option. Aside from oil extraction methods, the nut oil composition and nutrient content is determined by origin, species, variety, harvest time, and agro-technical interventions ¨ zcan, Ghafoor, Babiker & Hussain, 2018). (Al Juhaimi, O The chemical composition of harvested pistachio nuts from various regions was determined (Table 23.1). The nuts’ oil content ranged from 45.81% to 58.5%, the protein content ranged from 13.7% to 31.7%, and the moisture content ranged from 35.2% to 47.9%. The values for peroxide and acidity were 5.7 and 0.03% to 0.3%, respectively. The main fatty acid in the oil samples was oleic acid (46%
77.6%), subsequently linoleic acid (9.42%
38.6%), palmitic acid (4.6%
16.26%), palmitoleic acid (0.54%
1.2%), stearic acid (0.1%
4.21%), linolenic acid (0.27%
0.88%), arachidic acid (0.19%
0.33%), with more than 85% of triacylglycerols. The oil contains a cumulative of 125
258 mg/kg oil of tocopherol content, with the most abundant being γ-tocopherol (36.17
232 mg/kg oil), followed by δ-tocopherol (0.45
19.3 mg/kg oil), α-tocopherol (1.2
26.93 mg/kg oil), α-tocotrienoid (0.96
3.76 mg/kg), and γ-tocotrienoid (2.33
37.72 mg/kg). The average sterol content of the oils varied from 1125 to 2784 mg/kg oil. β-sitosterol (966
2419 mg/kg oil) was the most prevalent sterol in the oils, followed by

Multiple Biological Activities of Unconventional Seed Oils

282

23. Biological activities of pistachio (Pistacia vera) oil

TABLE 23.1 Chemical composition. Compounds

Chemical composition

References

Oil content

45.81%
58.5%

Aliakbarkhani et al. (2017), Dogan, C ¸ elik, Balta, Javidipour and ¨ zcan and AL Juhaimi (2014), Yavic (2010), Harmankaya, O Pourian et al. (2019), Roozban, Mohamadi and Vahdati (2006), Yahyavi et al. (2020)

Protein content

13.7%
31.7%

Aliakbarkhani et al. (2017), Harmankaya et al. (2014), Pourian et al. (2019), Seferoglu, Seferoglu, Tekintas and Balta (2006)

Moisture content

35.2%
47.9%

Yahyavi et al. (2020)

Mn

5.73
17.33 mg/kg

Aliakbarkhani et al. (2017), Harmankaya et al. (2014)

Fe

17
62.4 mg/kg

Aliakbarkhani et al. (2017), Harmankaya et al. (2014)

Zn

6.76
30.3 mg/kg

Aliakbarkhani et al. (2017), Harmankaya et al. (2014)

Cu

12.81 mg/kg

Harmankaya et al. (2014)

B

11.31 mg/kg

Harmankaya et al. (2014)

Mo

0.106 mg/kg

Harmankaya et al. (2014)

Cr

0.511 mg/kg

Harmankaya et al. (2014)

Ni

1.67 mg/kg

Harmankaya et al. (2014)

Na

0.06%
0.126%

Aliakbarkhani et al. (2017)

K

0.68%
1.35%

Aliakbarkhani et al. (2017)

P

0.42%
0.73%

Aliakbarkhani et al. (2017)

N

2.6%
4.29%

Aliakbarkhani et al. (2017)

Mg

0.11%
0.17%

Aliakbarkhani et al. (2017)

Ca

0.23%
0.47%

Aliakbarkhani et al. (2017)

Peroxide value

5.7

Allaith, Alfekaik and Alssirag (2019)

Acidity values

0.03%
0.3%

Allaith et al. (2019), Yahyavi et al. (2020)

Oleic acid

46%
77.6%

Allaith et al. (2019), Ballistreri, Arena and Fallico (2011a), Dogan ¨ zrenk, Javidipour, Yarilgac, et al. (2010), Mohamadi (2006), O ˘ Balta and Gu¨ndogdu (2012), Polari et al. (2019), Roozban et al. (2006), Seferoglu et al. (2006), Yahyavi et al. (2020)

Linoleic acid

9.42%
38.6%

Allaith et al. (2019), Ballistreri et al. (2011a), Dogan et al. (2010), ¨ zrenk et al. (2012), Polari et al. (2019), Roozban Mohamadi (2006), O et al. (2006), Seferoglu et al. (2006), Yahyavi et al. (2020)

Palmitic acid

4.6%
16.26%

Allaith et al. (2019), Ballistreri et al. (2011a), Dogan et al. (2010), ¨ zrenk et al. (2012), Polari et al. (2019), Mohamadi (2006), O Roozban et al. (2006), Yahyavi et al. (2020)

Minerals content

Fatty acid composition

(Continued)

Multiple Biological Activities of Unconventional Seed Oils

23.2 Pistacia vera chemical composition

TABLE 23.1

283

(Continued)

Compounds

Chemical composition

References

Palmitoleic acid

0.54%
1.2%

¨ zrenk et al. (2012), Yahyavi et al. (2020) Dogan et al. (2010), O

Stearic acid

0.1%
4.21%

¨ zrenk et al. (2012), Ballistreri et al. (2011a), Dogan et al. (2010), O Yahyavi et al. (2020)

Linolenic acid

0.27%
0.88%

¨ zrenk et al. (2012), Seferoglu et al. (2006), Dogan et al. (2010), O Yahyavi et al. (2020)

Arachidic acid

0.19%
0.33%

¨ zrenk et al. (2012), Seferoglu et al. (2006) Dogan et al. (2010), O

(OLO, OLL, OOO, LLL, OLP, LLP, and OOP)

.85%

Ballistreri, Arena, and Fallico (2010)

Total tocopherol content

125
258 mg/kg

Yahyavi et al. (2020)

γ-tocopherol

36.17
232 mg/kg

¨ zrenk et al. (2012), Yahyavi et al. (2020) O

δ-tocopherol

0.45
19.3 mg/kg

¨ zrenk et al. (2012), Yahyavi et al. (2020) O

α- tocopherol

1.2
26.93 mg/kg

¨ zrenk et al. (2012), Yahyavi et al. (2020) O

α-tocotrienoid

0.96
3.76 mg/kg

¨ zrenk et al. (2012) O

γ-tocotrienoid

2.33
37.72 mg/kg

¨ zrenk et al. (2012) O

Total carotenoid

1.01
4.93 mg/kg

¨ zrenk et al. (2012) O

Total sterol content

1125
2784 mg/kg

Yahyavi et al. (2020)

β-sitosterol

966
2419 mg/kg

Yahyavi et al. (2020)

Cholesterol

8.3
39 mg/kg

Yahyavi et al. (2020)

Campesterol

47.4
128 mg/kg

Yahyavi et al. (2020)

Stigmasterol

12.3
27.8 mg/kg

Yahyavi et al. (2020)

Δ5-avenasterol

72.6
170 mg/kg

Yahyavi et al. (2020)

α-Pinene

105
2464 mg/kg

Polari et al. (2019)

Total phenolics

1359
4507 mg/kg

Ojeda-Amador, Salvador, Fregapane and Go´mez-Alonso (2019)

Triacylglycerols

Terpenes

Flavanols (procyanidinB1 90% and gallocatechin)

Ojeda-Amador et al. (2019)

Anthocyanins

54
218 mg/kg

Ojeda-Amador et al. (2019)

Flavanols

76
130 mg/kg

Ojeda-Amador et al. (2019)

Flavanones

12
71 mg/kg

Ojeda-Amador et al. (2019)

Gallotannins

4
46 mg/kg

Ojeda-Amador et al. (2019)

Multiple Biological Activities of Unconventional Seed Oils

284

23. Biological activities of pistachio (Pistacia vera) oil

Δ5-avenasterol (72.6
170 mg/kg oil), campesterol (47.4
128 mg/kg oil), stigmasterol (12.3
27.8 mg/kg oil), and cholesterol (8.3
39 mg/kg oil). The most common volatile compounds in pistachio oil were discovered to be terpenes, aldehydes, and alcohols, out of 50 aroma compounds identified. Meanwhile, pistachio oil extract contains 14 aroma-active zones, and its phenolic fraction contains 12 phenolic compounds, seven of which are being initially discovered. The most dominant components of phenolics were identified to be eriodictyol-7-O-glucoside and protocatechuic acid (Sonmezdag, Kelebek & Selli, 2018). Phenolic components including flavonoids, anthocyanins, and trans-resveratrol, as well as other antioxidants, namely tocopherols, chlorophylls, and xanthophylls, are abundant in Italian pistachios. It contained approximately 185 mg of gallic acid equivalent (GAE)/ 100 g dry matter (DM), with anthocyanins (24 mg/100 g DM) contributing the majority of the polyphenols. Pistachios contain 0.2 mg/100 g DM trans-resveratrol, the same concentration present in red wines. It also had flavonoids at a concentration of 10 mg/100 g DM, such as daidzein, genistein, quercetin, daidzin, genistin, eriodictyol, luteolin, and naringenin (Ballistreri, Arena & Fallico, 2011b). Furthermore, virgin pistachio oils have an advantage over refined vegetable oils because they have unique and pleasant sensory qualities, providing consumers with more value. Its virgin oil contains a plentiful of oleic acid (55%
74%), γ-tocopherol (550
720 mg/kg), and phytosterols (3200
7600 mg/kg). Furthermore, its residual cakes have a high phenolic content of approximately 8600
15000 mg/kg GAEs and the antioxidant activities of 2,2-diphenyl-1picrylhydrazyl (12
46 mmol/kg) and oxygen radical absorbance capacity (155
496 mmol/kg). This highlights their functional ingredients’ potential and reservoirs of bioactive components (Ojeda-Amador et al., 2018). Boiling significantly reduced the antinutritive properties (tannins, saponins, oxalate, and alkaloids), ensuring that the samples are safe for human and animal use. The flour is high in macrominerals, which are beneficial in food formulation. The oil’s physicochemical characteristics revealed that the acid value was within the range of acceptable edible oils, and the peroxide and iodine content make the oil suitable for soap production (Amoo, Atasie & Akinola, 2012).

23.3 Uses of Pistacia vera The pistachio nut is among the world’s tastiest and nutritive nuts. New products must be developed to enhance the value of pistachio nuts and fulfill market demands. Pistachio halva, for instance, was produced with pistachio paste as the primary ingredient, as well as egg white, citric acid, sugar, and glucose. A combination of 0.10% of each soapwort root extract and commercially obtained Glycyrrhizin was added to the formulation to eliminate oil separation and improve consumer acceptance of the product. As a result, the formulation of pistachio halva provides customers with a healthy non-animal snack food made from nuts (Shakerardekani & Shahedi, 2015). Pistachio spreads were made with pistachio paste as the primary ingredient, icing sugar, and various ratios of soy protein isolate and red palm oil. The viscoelastic behavior of pistachio spreads was altered in the presence of palm oil (Shakerardekani, Karim,

Multiple Biological Activities of Unconventional Seed Oils

23.4 Biological activities of Pistacia vera oil

285

Ghazali & Chin, 2013). Pistachio butter was formed by mixing crushed pistachios and sugar paste, and the resulting substance is highly nutritious. According to the results, the treatments containing each 2% of lecithin and mono-diglycerides have the least amount of oil leakage. Furthermore, the addition of BHT antioxidant increased the peroxide benefit and shelf life of pistachio butter (Ardakani, Shahedi & Kabir, 2006). The emulsification process was used to create novel edible emulsified films from pistachio saturated fatty acids and globulin protein (Zahedi, Ghanbarzadeh & Sedaghat, 2010). The effect of pistachio hull ethanolic extract on common carp, Cyprinuscarpio, body structure, growth performance, total phenolic compound, and peroxide value was studied. As reported, an ethanolic extract of pistachio hull may be added to a fish pellets to retard oxidative damage in typical carp fillets (Motamedi-Tehrani, EbrahimiDorcheh & Goli, 2016). The soft shell bio-oil from pistachios has the ability to be introduced as both a renewable fuel and a chemical feedstock (Demiral, Atilgan & S¸ enso¨z, 2009).

23.4 Biological activities of Pistacia vera oil 23.4.1 Antioxidant capacity and oxidative stability Biological activities of pistachio oil were listed (Table 23.2). In regards to antioxidant capacity, pistachio was first ranked among nut oils, followed by hazelnut, walnut, almond, and peanuts. Since these nuts have the potential to be a great dietary fat source, determining their free radical scavenging capacity was valuable. There was a significant correlation between the DPPH activity and the oxidative stability (Rancimat method) assays. Tocopherols are the compounds that are responsible for this antioxidant ability, with polyphenols playing a minor position (Arranz, Cert, Pe´rez-Jime´nez, Cert & Saura-Calixto, 2008). The oxidative stability of the selected nut oils from almond, Brazil nut, hazelnut, pecan, pine nut, pistachio, and walnut was determined. The findings depicted that pecan and pistachio oils are the most stable, while pine nut and walnut oils are the least stable. Notably, in both the accelerated autoxidation and photo oxidation tests, oils extracted by chloroform/ methanol were more stable than oils extracted by hexane (Miraliakbari & Shahidi, 2008). Mono- and poly-unsaturated, saturated, and triglyceride esters are the most abundant fatty acids in pistachio oil (Salvador et al., 2019). Fatty acid composition can change as a result of oxidation caused by poor farming practices, improper harvesting time, and storage conditions. The pistachio oil quality determinant can be used to distinguish its quality and is associated with potential adulteration (Houshia, Zaid, Shqair, Zaid & Fashafsheh, 2014). Furthermore, pistachio oil’s antioxidant activity acts as its own natural preservative against the formation of oxidized compounds. Furthermore, the spectrum of phenolic compounds in pistachio oil has increased its shelf life, and cell death has been hindered and decreased in response to free radical insults. The determination of pistachio oil’s total antioxidant capacity is desirable in order to ensure the most important health benefits and sensory qualities are preserved. Furthermore, clinical evidence has linked the content of tocopherols to those health benefits (Servili & Montedoro, 2002).

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23. Biological activities of pistachio (Pistacia vera) oil

TABLE 23.2 Biological activities of Pistacia vera oil and its by-products. Pistacia vera

Extraction methods

Yield

Biological activities

Bioactive compounds

References

Pistachio kernel

Soxhlet (petroleum ether)

Pistachio oil

Antioxidant capacity

Tocopherol

Valasi et al. (2020)

Pistachio kernel

Methanolic extraction

Pistachio oil

Free radical Tocopherol scavenging capacity and Oxidative stability

Arranz et al. (2008)

Pistachio kernel

Hexane and chloroform/ methanol extractions

Pistachio oil

Oxidative stability Fatty acid tocopherol

Miraliakbari and Shahidi (2008)

Pistachio kernel

Hydrodistillation Essential oil

Scolicidal activity

Limonene, α-pinene, α-thujene and α-terpinolene

Mahmoudvand, Kheirandish, et al. (2016)

Pistachio kernel

Hydrodistillation Essential oil

Antileishmanial activities

Limonene, α-pinene, α-thujene and α-terpinolene

Mahmoudvand, Saedi Dezaki, et al. (2016)

Pistachio kernel

Commercial virgin pistachio oil

Pistachio oil

Antiinflammatory properties

Linoleic acid and β-sitosterol

Zhang et al. (2010)

Pistachio hull

Hydrodistillation Hull essential oil 0.25% (v/w fresh material)

Antioxidant, cytoprotective, and antimicrobial properties

40 volatile constituents; Smeriglio et al. monoterpene hydrocarbons (2017) and oxygenated monoterpenes (4-Carene, α-Pinene, D-Limonene, 3-Carene)

Pistachio hull

Hydrodistillation Essential oil

Antimicrobial activity

D-limonene and 3-carene

Alma et al. (2004)

Pistachio leaves

Hydrodistillation Essential oil

Herbicidal potential

α-Terpinene, α-pinene, limonene, α-terpineol

Ismail et al. (2012)

Through Fourier transform infrared (FTIR) spectroscopy and multivariate analysis, a simple, fast, economical, and environmentally friendly method for discriminating pistachio oils of the Greek variety, “Aegina,” according to their quality profile was developed. As a result, oil samples from different harvesting years showed significant variations that were successfully differentiated using the FTIR spectral area, and total antioxidant scavenging capabilities of 2,20-azinobis (3-ethylbenzothiazoline-6-sulforic acid diammonium salt) (Valasi, Arvanitaki, Mitropoulou, Georgiadou & Pappas, 2020).

Multiple Biological Activities of Unconventional Seed Oils

23.4 Biological activities of Pistacia vera oil

287

23.4.2 Scolicidal activity This study discovered a new compound of the pistachio with less toxicity and potential scolicidal activity, implying that it could be applied as a safer scolicidal agent. More research is needed to verify these results by studying the pistachio essential oil as a new scolicidal agent in a clinical environment. Various scolicidal agents are currently used to inactivate protoscoleces during hydatid cyst surgery. However, serious adverse effects such as liver necrosis, sclerosing colangititis, and methaemoglobinaemia were noticed (Mahmoudvand, Kheirandish, Dezaki, Shamsaddini & Harandi, 2016).

23.4.3 Antileishmanial activities Pistachio essential oil exhibited substantial effectiveness via preclinical testing against Leishmaniatropica and Leishmania major in comparison to the meglumine antimoniate drug (Glucantime). Furthermore, J774 cells were not harmed by this essential oil. Plant resources can be utilized in conventional medicine to treat cutaneous leishmaniasis, according to scientific evidence (Mahmoudvand, Saedi Dezaki, et al., 2016).

23.4.4 Antiinflammatory properties Genes involved in immune response including INF-induced protein with tetratricopeptide repeats 2 (Ifit-2), bacteria defense, and gene silencing are significantly reduced by pistachio oil. Since pistachio oil and bioactive molecules of linoleic acid and β-sitosterol reduce Ifit-2 expression, this gene may be used as a biomarker to monitor diet-induced changes in inflammation (Zhang, Kris-Etherton, Thompson & Heuvel, 2010). The ability of PEGlated nanoliposomes of pistachio unsaturated oils (PEGNLPUOs) to reduce inflammation in the autoimmune encephalomyelitis animal model was studied. The intervention of PEGNLPUOs (10% v/v) markedly reduced the gene expression related to the nuclear factor kappa-light-chain-enhancer of activated B (NFKB) and oxidative stress signaling pathways (Jebali et al., 2020).

23.4.5 Anxiety and depressive-like behaviors Polycystic ovary syndrome (PCOS) is associated with a variety of complications, including neurobehavioral deficits in women who have PCOS, which reduces their quality of life. It is beneficial to find a safe herbal medicine for these complications. This research aims to determine the pistachio oil effects on depression and anxiety-like behaviors in female rats with letrozoleinduced PCOS. To induce PCOS, letrozole (1 mg/kg) was administered orally. Letrozole was given with pistachio oil (1 and 4 mL/kg). Elevated plus-maze, forced swimming test, and open field testing were completed 21 days later. To summarize, the findings of this study indicated that administering pistachio oil to female rats with PCOS could reduce depression and anxiety. More research is needed to determine pistachio oil’s potential protection against PCOS and other complications, as well as its likely mechanistic of action (Mohammadreza et al., 2019).

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23. Biological activities of pistachio (Pistacia vera) oil

23.5 Biological activities of Pistacia vera by-products The biological activities of pistachio oil by-products have been listed (Table 23.2). Despite its antioxidant and health-promoting properties, as well as abundant of bioactive compounds, pistachio hull is considered as a waste and may cause environmental issues. Nonetheless, subsequent in vivo and in vitro experiments revealed that pistachio hull extract is an antioxidant, cytoprotective, and photoprotective agent, as well as having antibacterial, antiinflammatory, antimelanogenic, and antimutagenic attributes (Arjeh, Akhavan, Barzegar & CarbonellBarrachina, 2020). The Pistacia vera L. variety Bronte hull displayed great free-radical scavenging ability as measured by iron chelating activity against hydroxyl radical, but only weak results against DPPH radical. Furthermore, tert-butyl hydroperoxide had a remarkable cytoprotective effect on lymphocytes, increasing cell viability and decreasing lactate dehydrogenase release. Meanwhile, the antimicrobial properties of this essential oil were identified, as it was bactericidal against all strains studied except Pseudomonas aeruginosa ATCC 9027. Its high concentration of monoterpene derivatives of 4-Carene, α-Pinene, D-Limonene, and 3-Carene led to its exceptional antioxidant and cytoprotective properties. As a result, this mixture may be a worthy natural components to be incorporated in food preservation, pharmaceutics, cosmetics, and biotechnology (Smeriglio et al., 2017). The essential oil extracted from the Turkish pistachio hull was found more efficient than Nystatin, a synthetic yeastcide. Moreover, under the conditions tested, the oil’s antibacterial activity was less than that of normal antibiotics, ampicillin sodium, and streptomycine sulfate (Alma et al., 2004). Multiple reports have confirmed the potential of pistachio hull as a nutritious source for pharmaceutical and food industries to increase the consistency and nutritional characteristics of their drugs. However, further research is required to expand the benefits of this natural by-product (Arjeh et al., 2020). The antifungal action of pistachio hull essential oil may be attributed to the prevention of Candida species resistance. Nonetheless, further research is necessary to ascertain the processes underlying the operation of pistachio hull essential oil (D’Arrigo et al., 2019). On the other hand, the phytotoxic action of the pistachio leaves essential oil against seed germination and seedling growth of four weed species, Sinapisarvensis, Trifoliumcampestre (dicots), Loliumrigidium, and Phalariscanariensis (monocots), as a result of its comparatively high content of monoterpene hydrocarbons, making it potentially useful as a bioherbicide. However, further research is needed to evaluate the price, suitability, safety, and phytotoxicity of these agents as potential herbicides against cultured plants (Ismail, Lamia, Mohsen & Bassem, 2012). Pistachio flour, another oil industry by-product, can be extended as a food constituent in functional foods due to its nutritive quality. Furthermore, this flour was rich in unsaturated fatty acids, mostly oleic and linoleic, in addition to potassium, phosphorus, magnesium, and calcium. The protein secondary structure was primarily formed by parallel β-sheet and α-helix. Pistachio protein is in its natural state in the by-product and can be denatured at 100 C and above. As a consequence, food processing of this constituent can alter the components structure (Salinas et al., 2020). The substitution of pistachio by-products instead of alfalfa hay in the diet of dairy Saanen goats has no harmful effects on ruminal fermentation or blood metabolites. Furthermore, pistachio by-products have the ability to alter the fatty acid profile of milk in dairy goats (Ghaffari, Tahmasbi, Khorvash, Naserian & Vakili, 2014).

Multiple Biological Activities of Unconventional Seed Oils

References

289

23.6 Safety concern Since conventional crop plants produce edible oils that are believed to be healthier than animal-based fats and oils, demand for this oil is growing. More emphasis has been put on the utilization of the oils derived from pistachios, almonds, and walnuts in salad dressings as well as in the fragrance oil, soap, and cosmetics industries. Contrary to popular belief, aflatoxins are a significant problem in relation to these seed oils. To establish and evaluate the safety of dietary supplements or cosmetics containing such oils, a certified analytical method for the study of aflatoxins of these plant-derived oils is needed (Mahoney & Molyneux, 2010). Antimicrobial packaging is designed to prolong the shelf life of foods while also providing microbial protection for customers by inhibiting fungal growth on pistachios and the formation of aflatoxins. As a result, the alcoholic extract of Zatariamultiflora had a 90 ppm inhibition concentration. The findings have revealed that when whey protein concentrate coating was combined with 2500 ppm Zatariamultiflora extracts, A. flavus growth was fully inhibited (Javanmard & Ramazan, 2009). Gamma radiation was also applied to peeled and unpeeled pistachios to investigate aflatoxin B1 inactivation in food and feed crops (Ghanem, Orfi & Shamma, 2008). The bleaching method was used to whiten nut shells for antifungal and cosmetic purposes on the one hand. Unfortunately, the bleaching procedure has a detrimental effect on the food content and health issues. A bleach containing hydrogen peroxide and transit metals increased lipid peroxidation levels as well as decreased the phytosterol content. Since the resulting pistachio oil was discovered to be harmful to cells, bleaching pistachios was strongly discouraged (Racicot, Craven & Chen, 2012).

23.7 Conclusion Numerous experiments on the chemical structure of pistachio oil have been performed, but there have been few studies on its biological activities. Despite being regarded as a waste that may cause environmental issues, pistachio by-products are increasingly being recognized as a beneficial waste. The dynamic matrix of pistachio by-products essential oil may be a good natural source of nutraceutical compounds for use in food processing, pharmaceutics, cosmetics, and biotechnology. Nonetheless, more research is required to support the use of both pistachio oil and its by-product.

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197. Available from https://doi.org/10.1007/978-3-030-12473-1_7. Seferoglu, S., Seferoglu, H. G., Tekintas, F. E., & Balta, F. (2006). Biochemical composition influenced by different locations in Uzun pistachio cv. (Pistacia vera L.) grown in Turkey. Journal of Food Composition and Analysis, 19(5), 461
465. Available from https://doi.org/10.1016/j.jfca.2006.01.009. Servili, M., & Montedoro, G. F. (2002). Contribution of phenolic compounds to virgin olive oil quality. European Journal of Lipid Science and Technology, 104(9
10), 602
613. Available from https://doi.org/10.1002/1438-9312 (200210)104:9/10602:AID-EJLT6023.0.CO;2-X. Shakerardekani, A., & Shahedi, M. (2015). Effect of soapwort root extract and glycyrrhizin on consumer acceptance, texture, and oil separation of pistachio halva. Journal of Agricultural Science and Technology, 17(6), 1495
1505. Shakerardekani, A., Karim, R., Ghazali, H. M., & Chin, N. L. (2013). Development of pistachio (Pistacia vera L.) spread. Journal of Food Science, 78(3). Available from https://doi.org/10.1111/1750-3841.12045. Smeriglio, A., Denaro, M., Barreca, D., Calderaro, A., Bisignano, C., Ginestra, G., & Trombetta, D. (2017). In vitro evaluation of the antioxidant, cytoprotective, and antimicrobial properties of essential oil from Pistacia vera L. Variety Bronte Hull. International Journal of Molecular Sciences, 18(6). Available from https://doi.org/10.3390/ijms18061212. Sonmezdag, A. S., Kelebek, H., & Selli, S. (2018). Pistachio oil (Pistacia vera L. cv. Uzun): Characterization of key odorants in a representative aromatic extract by GC-MS-olfactometry and phenolic profile by LC-ESI-MS/MS. Food Chemistry, 240, 24
31. Available from https://doi.org/10.1016/j.foodchem.2017.07.086. Tsantili, E., Takidelli, C., Christopoulos, M. V., Lambrinea, E., Rouskas, D., & Roussos, P. A. (2010). Physical, compositional and sensory differences in nuts among pistachio (Pistachia vera L.) varieties. Scientia Horticulturae, 125(4), 562
568. Available from https://doi.org/10.1016/j.scienta.2010.04.039. Valasi, L., Arvanitaki, D., Mitropoulou, A., Georgiadou, M., & Pappas, C. S. (2020). Study of the quality parameters and the antioxidant capacity for the Ftir-chemometric differentiation of Pistacia vera oils. Molecules (Basel, Switzerland), 25(7). Available from https://doi.org/10.3390/molecules25071614. Yahyavi, F., Alizadeh-Khaledabad, M., & Azadmard-Damirchi, S. (2020). Oil quality of pistachios (Pistacia vera L.) grown in East Azarbaijan, Iran. NFS Journal, 18, 12
18. Available from https://doi.org/10.1016/j. nfs.2019.11.001.

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C H A P T E R

24 Biological activities of argan (Argania spinosa L.) oil: Evidences from in vivo studies Nicholas M.H. Khong1 and Kim Wei Chan2 1

School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor, Malaysia 2Natural Medicines and Products Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Selangor, Malaysia

24.1 Abbreviations Apo A1 AO BW CAT CVD FA GPx HDL i.p. LOOH LDL MUFA MDA ORAC PUFA TBARS

apolipoprotein A1 argan oil body weight catalase cardiovascular disease fatty acids glutathione peroxidase high-density lipoprotein intraperitoneal lipoperoxides low-density lipoprotein monounsaturated fatty acids malondialdehyde oxygen radical absorbance capacity polyunsaturated fatty acids thiobarbituric acid-reacting substances

24.2 Introduction Argan oil (AO) is an oil product obtained from the kernels of the argan (Argania spinosa) fruits. Depending on how these kernels are processed, different grades of AOs are produced. Argan oil extraction has come a long way from being obtained from the kernels

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00008-8

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24. Biological activities of argan (Argania spinosa L.) oil: Evidences from in vivo studies

manually to the current advancements in machines and automations that have helped save time and ensure high-quality production. While only being classified by traditionally processed oil, cold-pressed or virgin oil and solvent-extracted oil previously (Monfalouti et al., 2010), AO are more often marketed as edible and cosmetic grade oils, nowadays. In this current setting, cosmetic grade argan oil is obtained by unroasted kernels while the edible grade oil by roasted kernels prior to grinding, with the former being sold at higher price. Though with the advancement of technology nowadays, most edible grade argan oils areconsidered cold-pressed oil with improved machinations that allows extraction without the application of heat. As reported extensively elsewhere, AO contains 80% unsaturated fatty acids and is exceptionally rich in natural tocopherols, phenols, phenolic acid, carotenes and sterols. Although the plant origin and the processing method involved are major quality criterion to many other vegetable oils, some studies suggested otherwise in the case of argan oil especially on its polyphenol and tocopherol content (Hilali et al., 2005). By and large, the quality criterion of argan oil grades are generally specified by a Moroccan standard (Norme Marocaine 08.5.090, 2002) elaborated in 2003. In the past, AO was extensively used only in Morocco as argan trees are reportedly endemic in Morocco. Indigenously, argan oil is an ethnobotanical medicine used to topically treat all kind of dermatological ailments, particularly pimples, juvenile acne and chicken pox pustules, dry skin conditions, wrinkles, rheumatism; while orally prescribed as choleretic, hepatoprotective agent, and in the case of hypercholesterolemia and atherosclerosis (Charrouf & Guillaume, 1999). Although some other biological applications have been reported of argan-derived products from other parts of the tress, argan oil is by far still the most valuable product derived from the argan tree. Originally, the pharmacological properties of argan oil have simply been deduced by considering of the properties of its major constituents, which have been isolated and biochemically evaluated, often in simple models. The chemical constitutent of argan oil has already been detailed elsewhere and this aspect will therefore not be discussed here. One element which contrast the current review with previous reports would be the depth of scientific knowledge employed, where instead of the many in vitro benefits claimed of argan oil, cohort or clinical studies from the 2000s will be prioritized. Forthcoming development of argan oil will also be discussed using preclinical studies involving different animal models of the past one decade.

24.3 Biological effects on human health Argan oil was found to exert health-promoting properties both through ingestion, as a food ingredient, and through topical application.

24.3.1 Clinical evidences Argan oil has been clinically shown to prevent degradation of cardiovascular and metabolic health, skin aging and other negative consequences contributed by oxidation (Table 24.1). The trend of the oil in clinical trials involving skin regeneration and esthetic effects have also been steadily increasing due to high market demands of skin enhancing products and emergence of quantitative noninvasive analytical procedures. Most studies

Multiple Biological Activities of Unconventional Seed Oils

TABLE 24.1 Clinical evidences of argan oil impact on human health promotion. Health Ailments

Inclusion and randomization

Intervention

Outcome

References

Hyperlipidemia

Healthy nonsmoking subjects (N 5 96, 79.2% women), into 2 groups: AO group (n 5 62) and control group (n 5 34)

Cardiovascular disease risk

Healthy male subjects, aged 20
43 years (N 5 60) in 2 groups: AO (n 5 30) and olive oil group (n 5 30)

• Plasma lipid profile improved Drissi et al. (2004) (k LDL-C, k Lp(a), k Apo B) • Plasma antioxidant level improved (k LPO, m Vit. E) • Molar ratio of a-tocopherol/total cholesterol increased. Consumption of AO or olive oil (25 g/ • Serum Lipid Values improved Derouiche et al. day) for 3 weeks after consumption of (k TAG, k TC, m HDL-C, m (2005) butter (25 g/day) for 2 weeks prior ApoA1)

Atherosclerosis

Healthy male subjects (N 5 60), in 2 groups: AO group (n 5 30) and olive oil group (n 5 30)

Type-2 Diabetes complications

Type-2 diabetic patients with dyslipidemia, aged 40
80 years, (N 5 86) randomized into 2 groups: AO (n 5 43) and control (butter, n 5 43) group

Cardiovascular disease risk

Healthy subjects (N 5 40), aged 25
45 years, in 2 groups: AO group (n 5 20) and control group (n 5 20)

Consumption of AO (15 g/day)

Consumption of AO or olive oil • Plasma lipid peroxidation (25 mL/day) in a single dose every the decreased (k LPO, k Mr, k MDP) morning with toasted bread for • LDL susceptibility to lipid 3 weeks peroxidation decreased (m LP) • Plasma antioxidant enzyme activity increased (m PON1, m PON1-NaCl, m AE) • Plasma Vit E concentration significantly increased only in argan oil group. Consumption of AO (25 mL/day) • Blood lipid profile improved conmpared to butter (20 g/day) in the (k TAG, k TC k LCL-C) morning with toasted bread for 3 • Susceptibility of LDL to lipid weeks peroxidation reduced (m LP) Consumption of AO (15 g/day) in the morning with toasted bread for 30 days

• Plasma lipid profile improved (kTAG, k TC, k LDL-C) • Circulating and cellular lipid and protein oxidation decreased (kTBARS, k TBARS erythrocytes, kLOOH, k LOOH erythrocytes, k PC) • Susceptibility of LDL oxidation decreased (m LP, k MDP) • Plasma antioxidants increased (m Vit E, m CAT erythrocytes)

Cherki, Derouiche, Drissi, El Messal, Bamou, IdrissiOuadghiri, and Diseases (2005)

Ould Mohamedou et al. (2011)

Sour et al. (2012)

(Continued)

TABLE 24.1 (Continued) Health Ailments

Inclusion and randomization

Intervention

Outcome

Dyslipidemia

Hypercholesterolemia or/and hypertriglyceridemia patients (79% women) in 2 groups (N 5 39): AO group (n 5 21) and control group, i.e., butter (n 5 18)

Postmenopausal Oxidative Stress

Postmenopausal women not taking estrogen, steroids, or osteoporosis medication with the average age of 55.5 6 6.2 years (N 5 151) in an exploratory, randomized trial of 2 groups: AO group (n 5 74) and olive oil group (control, n 5 77)

• Atherogenic lipid parameters improved (k TC, k LDL-C, m HDL-C) • Platelet hyperactivity lowered (k PA) • Oxidative status was enhanced (m MDA, m GPx) Daily consumption of 25 g of AO for 8 • Significant increase of vitamin E weeks, after a 2-week diet based of concentration in the blood as early 25 g of nonhydrogenated margarine as as Week 4 and continue to increase the only lipid source till Week 8

Dry skin

Healthy-skin Caucasian volunteers of Application of AO skin formulation, once a day, on one forearm while the both sexes aged between 21 and 30 years separated into 2 groups (N 5 10): other acts as control for 1 month Group 1 (n 5 5) applied the AO nanostructured lipid carrier-based hydrogel (HG-NLC) formulation while Group 2 (n 5 5) applied the AO hydrogel (HG) formulation

Progression of chronic renal failure

End-stage renal disease on maintenance hemodialysis for at least 12 months (N 5 37) in a crossover, controlled trial, of group A (n 5 19) or group B (n 5 18) where each period lasted for 4 weeks. No placebo was used

Consumption of AO (25 mL/day) in the morning for 3 weeks

• Skin hydration increased

Group A consumed 30 mL/day of AO • Lipid profile in hemodialysis in a single dose with bread every patients improved (k TAG, k TC, morning in the first period while k LDL-C, m HDL-C) group B was the control group. • Hemodialysis-caused oxidative Groups were reversed as in crossover stress reduced (k MDA, m Vit. E) design, after 8 weeks as a washout period

References Haimeur, Messaouri, Ulmann, Mimouni, Masrar, Chraibi, and Disease. (2013)

Monfalouti et al. (2013)

Tichota et al. (2014)

Eljaoudi et al. (2015)

Postmenopausal skin degeneration

Postmenopausal women (N 5 60) were randomly divided into 2 dietary groups: AO and control (olive oil) group (n 5 30 each) while at the same time, both groups also received cosmetic AO to be used in parallel with the dietary study

•Consumption of AO (25 mL/day) for • Consumption of argan oil 60 days after consuming 25 g/day of increased elasticity of the skin butter for 2 weeks (m gross-elasticity, m net elasticity, m biological elasticity, m RRT) • All subjects applied cosmetic AO (10 drops) in the left volar forearm during • Application of argan oil led increase elasticity of the skin a 60-day period (m gross-elasticity, m net elasticity, m biological elasticity, m RRT) Argan oil was prepared into water-in- • Significant improvement in skin oil cream. The cosmetic product was elasticity (k skin retraction time) applied twice daily, by massage, at the • No adverse effects (erythema and upper arms level on the area pruritus) predisposed to stretch marks occurrence, for 7 days

Boucetta et al. (2015)

Striaedistensae

Healthy female subjects, with age between 22 years and 60 years, (N 5 12) in a pilot study

Inflammaging

Elderly subjects (N 5 138, age 65
85 years old, equal number of males and females) in a multicenter, “open-label” randomized study of 4 arms all of RISTOMED diet: Arm A (n 5 34), control; Arm B (n 5 35), Probiotic blend; Arm C (n 5 34), d-Limonene; and Arm D (n 5 35), AO

Nutraceuticals were provided with • Inflammatory status decreased AO in 12.5 mL monodose sachets. The (k ESR) daily recommended intake was 25 mL taken as two monodoses per day at each person’s convenience with breakfast, lunch and/or dinner, for a period of 56 6 2 days

Ostan et al. (2016)

Knee osteoarthritis

Knee osteoarthritic patients of 58.24 6 7.2 years (N 5 100, 93% women) into 2 groups: AO group (n 5 51) and control group (n 5 49)

Consumption of AO every morning (30 mL/day) for 8 weeks

Hepatic steatosis Obese, hypertensive, hypercholesteraemic, and Type-2 diabetes patients (N 5 29, aged 61.28 6 11.73 years old, 79.3% women) randomly divided into 2 groups: AO group (n 5 17) and control group (n 5 12)

Consumption of AO (25 mL/day) for 3 weeks

• Significant improvements in clinical knee osteoarthritis parameters (k pain VAS, k WOMAC pain index, m WOMAC function index, m Lequesne index, m Walking distance) • No side effects • Lipid levels improved (k TAG, m ApoA1, k ApoB100, k ApoB100/ ApoA1 ratio) • Risk of chronic liver disease decreased (k A2M)

Bogdan et al., 2016

Essouiri et al. (2017)

Mouhib et al. (2020)

(Continued)

TABLE 24.1 (Continued) Health Ailments

Inclusion and randomization

Intervention

Outcome

References

Depression symptoms

Elderly subjects (N 5 125, age 65
85 years old, equal number of males and females) in a multicenter, open-label, randomized study of 4 parallel arms all with RISTOMED diet: Arm A (n 5 31), control; Arm B (n 5 31), Probiotic blend; Arm C (n 5 30), dLimonene; and Arm D (n 5 33), AO

A personalized diet intervention given • Inflammatory profile decreased through a web platform with AO (k ESR) provided in 12.5 mL monodose • Depressive symptoms decreased sachets. The daily recommended (kCES-D) intake was 25 mL taken as two monodoses per day at each person’s convenience, in substitution for a comparable amount of fat in the RISTOMED diet for 2 months

BourdelMarchasson et al. (2020)

Hormonal imbalance (male)

Young and healthy male subjects of a mean age of 23.42 6 3.85 years (N 5 60) in controlled nutritional intervention of 2 groups: AO group (n 5 30) and olive oil group (n 5 30)

Consumption of AO or olive oil • Androgen hormonal profiles (25 g/day) for 3 weeks, upon a 2-week improved (m testosterone, m LH) baseline consumption of butter (25 g/day)

Derouiche et al. (2013)

Key: TAG, triacylglycerol; TC, total cholesterol; HDL-C, HDL cholesterol; LDL-C, LDL cholesterol; Lp(a), lipoprotein (a); Apo B, apolipoprotein B; PC, protein carbonyls; LP, lag phase; Mr, maximal rate; IDP, initial conjugated diene production; MDP, maximum conjugated diene production; Mr, maximal rate of dienes production; CAT, catalase; PA, platelet aggregation; MDA, malondialdehyde (MDA is commonly determined by TBARS); TBARS, thiobarbituric acid reactive substance; pl, plasma; LOOH, lipoperoxides; GPx, glutathione peroxidase; LPO, lipid peroxides; PON1, Paraoxonase 1; PON1-NaCl, salt-stimulated paraoxonase; AE, Arylesterase; A2M, α-2 macroglobulin; Apo B100, Apolipoprotein B100; Apo A1, Apolipoprotein A1; VAS, visual-analog scale; WOMAC, The Western Ontario and McMaster Universities index; ESR, Erythrocytes Sedimentation Rate; CES-D, Center for Epidemiologic Studies Depression Scale; RRT, resonance running time; LH, luteinizing hormone.

24.3 Biological effects on human health

301

linked these health-promoting effects to the antioxidant properties of the oil. Note worthily, one major shortcoming of the currently available clinical trials are they are mostly consisted of prospective studies conducted in a uni-center setting. Hence, the sample size number of subjects is also low albeit statistically acceptable. Till date, AO has been most successfully proven to prevent risk of adverse CVD outcomes and promotes dermatological improvements in human subjects. Not surprisingly, some earliest studies investigating the application of AO were mostly based on the chemical composition of the oil which is rich in unsaturated fatty acids, phenolic compounds, phytosterols and tocopherols
all that is well known as effective antioxidants in the alleviation of hypercholesterolemia, hypertension, fatty liver and coronary artery disease,. Earlier, Ursoniu et al. (2018) synthesized evidence from 5 clinical trials concluding that supplementation of AO reduces plasma total cholesterol, LDL cholesterol, and triglycerides; while increases plasma HDL cholesterol levels. Most clinical trials performed on AO would include an antioxidant or oxidation prevention component as a primary outcome. So far, the positive effects of AO tested on human health is linearly linked to the protective effects against oxidative stress and high contents of antioxidants. Drissi et al., 2004 demonstrated a significant correlation between lower plasma lipoperoxide and LDL cholesterol levels with higher Vitamin E concentrations in healthy subjects regularly consuming AO. Haimeur, Messaouri, Ulmann, Mimouni, Masrar, Chraibi, and Disease. (2013) also attributed the prevention of prothrombotic complications associated with dyslipidemia, which are a major risk factor for cardiovascular disease, to the enhancement of oxidative status after a 3-week consumption of AO in dyslipidemic patients. In another study, consumption of AO was proven to improve plasma paraoxonase (PON1) activities and antioxidant status while decreasing lipoperoxide and conjugated diene formation in healthy subjects (Cherki, Derouiche, Drissi, El Messal, Bamou, Idrissi-Ouadghiri & Diseases, 2005). Besides, the consumption of AO was also found to increased plasma Apo A1 concentrations, while decreased plasma Apo B100 (Mouhib et al., 2017; Mouhib et al., 2020). These outcomes from separate studies aligned well with the finding of Hine et al. (2012) where both HDL associated proteins, Apo A1 and PON1 were found to inhibit LDL oxidation in the absence of HDL and enhance the ability of HDL to inhibit LDL oxidation. Apo A1 and PON1 can also contribute to the antioxidant activity of HDL in vitro.

24.3.2 Preclinical studies and imminent developments of argan oil In the past decade, AO was preclinically tested over an extensive variety of emerging health ailments, away from the oil’s traditional usages, for both prevention as well as treatment purposes. Some interesting studies that exhibited promising preclinical outcomes includes antidiabetic (Type 1 and II), neuroprotective, hepatoprotective, and nephroprotective activities. Table 24.2 listed the preclinical studies of AO tested using various animal models from the past decade. Although cardiovascular protective effects of AO are the most longstanding claimed pharmacological effects of argan oil, only protective effect of Type-2 Diabetes is proven due the recruitment of Type-2 diabetes patients in the clinical trials of the former (Ursoniu

Multiple Biological Activities of Unconventional Seed Oils

TABLE 24.2 Health-promoting activities of argan oil in animal models. Health-promoting activity

Animal Treatment/model

Outcome

Reference

Antihypertension

Rat

Male Sprague-Dawley rats (230
250g, N 5 40) were divided into 4 groups & treated for 5 weeks: Group 1 (n 5 10) had free access to a drinking solution of 10% D-glucose & to a normal chow diet; Group 2 (n 5 10) had free access to 10% D-glucose & was treated daily by gavage with AO (5 mL/kg BW); Group 3 (n 5 10) had free access to 10% D-glucose & was treated daily by gavage with corn oil (5 mL/kg BW); & Group 4 (n 5 10) as a control group with tap water ad libido.

• • • •

Anti-thrombosis

Mice

Mice (20
30 g) were r&omLy distributed into 3 groups (n 5 8
10) treated orally for 1 week with dH2O (1 mL/100 g BW/day, control group), AO (1 mL/100 g BW/day, treated group), or acetyl salicylic acid (ASA; 100 mg/kg BW/day, positive control). Acute pulmonary thromboembolism was induced, after AO treatment, by a thrombogenic mixture (collagen, 80 mg/kg 1 epinephrine, 1 mg/kg) by a rapid intravenous injection in the tail vein.

• Protection against Mekhfi et al. (2012) thromboembolism (paralysis or death) attack m • Density of occluded blood vessels k

Rat

Male Sprague-Dawley rats (70
80 g) were r&omLy divided into 4 groups (n 5 10) & treated for 12 weeks as follows: Group 1 had free access to a drinking solution of 10% D-glucose & a st&ard chow diet; Group 2 had free access to 10% D-glucose & AO (5 mL/kg BW/day); Group 3 had free access to 10% D-glucose & corn oil (5 mL/kg BW/day); Group 4 is a control group & had free access to tap water only & to the same st&ard chow diet.

• The final BW & BW gain in El Midaoui, Haddad, glucose-fed rats k Filali-Zegzouti, & • the rise in blood glucose levels Couture (2017) & insulin resistance effect in glucose-fed rats k • The plasma adiponectin level m • the increase in epididymal fat weight per body weight k • the plasma TG & leptin levels k • epididymal adipocyte cells size k • Prevented occurrence of tactile allodynia in glucose-fed rats • Cold allodynia in glucose-treated rats k • Oxidative stress parameters k • Kinin B1 receptor protein expression in thoracic aorta & gastrocnemius k

Cardiovascular risk prevention

the increase in SBP k El Midaoui, the increase in glucose levels k Haddad, & Couture (2016) the rise in the IR index k normalization of superoxide anion production • the increase in NADPH oxidase activity in glucose-fed rats prevented

Cardiovascular risk prevention

Rat

Male Wistar rats (120 6 10 g) were r&omLy assigned to 4 groups (n 5 6) as follows: control group, fed a st&ard diet with 16 kcal % fat; a high-fat (HF) group fed a high-fat diet with 64 kcal % fat (essentially coprah); a high-fat diet supplemented with 5% (w/w) fish oil &; the last group received a high-fat diet supplemented with 5% (w/w) AO.

• The plasma TC & TG levels k Haimeur et al. (2019) • Total MUFAs & ω-6 PUFAs, oleic acid (18: 1 ω-9) & the linoleic acid (18: 2 ω-6) levels in plasma m • The oleic acid (18: 1 ω-9) & the linoleic acid (18: 2 ω-6) levels in liver phospholipids m • Prevented high fat-induced oxidative status in the liver (MDA level k & GPx activity m). • ADP-induced platelets & collagen-induced platelets k

Anti-Type II diabetes & antihypertensive

Rat

Streptozotocin induced Type-2 Diabetic Wistar male & female rats with glucose levels . 1.50 g/l were used in the study. They were divided into 5 groups (n 5 6): Group 1 control group; Group 2 diabetic-hypertensive received L-NAME at 30 mg/kg/day; Group 3 diabetic rats treated with L-NAME (30 mg/kg/day) & AO (2 mL/kg/day); Group 4 diabetic rats treated with L-NAME (30 mg/kg/day)& olive oil (2 mL/kg/day); & Group 5 diabetic animals received L-NAME (30 mg/kg/day) 1 glibenclamide (GLI, 2 mg/kg/day) & captopril (CAP, 10 mg/kg/day). All the treatments were given orally in a volume of 0.1 mL/kg body mass.

• RPAT m • EDL muscle massm • Body mass m Increased SBP k in 3 weeks • Significant reduction in blood glucose levels (p , 0.01). • Significant increase in hepatic glycogen levels (p , 0.01).

Bellahcen et al. (2013)

Anti-diabetes

Rat

Wistar rats (180
210 g) were subjected to Alloxan to induce diabetes mellitus (i.p. 75 mg/kg BW/day & for 5 consecutive days). AO was provided in 2 modes: Mode1 Pretreatment with VAO before the administration of alloxan where the animals (n 5 6) received 2 mL/kg of AO orally for 7 consecutive days, before injection of alloxan; Mode 2 Simultaneous treatment with AO & alloxan where the animals (n 5 6), received 2 mL/kg AO orally & simultaneously, i.p. injections of alloxan for 5 consecutive days. Along these, appropriate controls were also used.

• Loss of body mass k • Increased blood glucose levels k • Reduced hepatic glycogen levels m

Bellahcen et al. (2012)

(Continued)

TABLE 24.2 (Continued) Health-promoting activity

Animal Treatment/model

Outcome

Reference

Anti-hyperglycemic

Rat

Wistar rats were i.p. injected by a single dose of Streptozotocin (60 mg/kg) & for the induction of diabetes mellitus. Normal & diabetic Wistar rats (glycaemia . 1.5 g/L) (150
250 g) & were divided into 4 groups (n 5 6). Control group: Received the distillate water (10 mL/kg; p.o.). Drug group: Received Acarbose (10 mg/kg; p.o.). Roasted AO group: Received roasted AO (2 mL/kg; p.o.). Unroasted AO group: Received Unroasted AO (2 mL/kg; p.o.). After 30 min of oral administration of the products to be tested, the animals were orally loaded with 2 g/kg of sucrose.

• postpr&ial glycaemia k • postpr&ial glucose upon oral starch overload k • postpr&ial blood glucose upon sucrose administration k • intestinal glucose absorption k

Daoudi et al. (2020)

Anti-obesity

Rat

Adult male Wistar rats (180
200 g, N 5 20) were r&omly distributed into 4 groups: The normal diet (ND) group was fed with ND for 12 weeks; the ND-AO group was fed with ND for 8 weeks followed by 4 other weeks a normal diet in which 30 g of corn oil were replaced by argan oil; the high-fat diet (HFD) group was fed for 12 weeks high-fat diet; the HFD-AO group was fed for 8 weeks a high-fat diet, then for 4 other weeks high-fat diet in which 50 g of corn oil were replaced by AO.

• Plasma markers of lipid peroxidation (TBARS & LOOH) k • Susceptibility of LDL to copper-induced oxidation k • Plasma vitamin E, CAT & SOD m • Weight gain in both normal & obese rats k • Plasma glucose & insulin concentrations k

S Sour et al. (2015)

Prevention of Anxiety & Neurodegeneration

Rat

Wistar rats (34 6 2g, 21 days old, N 5 35) were divided into 3 groups: Control group: untreated, normal saline (n 5 11); Stress group: submitted to Unpredictable Chronic Mild Stress (UCMS, n 5 12); AO 1 Stress group: supplemented by AO (10 mL/kg) & submitted to UCMS (n 5 12). Animals were administered AO mL & normal saline (control) orally for 10 weeks, from weaning 21th to 93 Post-natal Day (PND) while UCMS were subjected for 6 weeks: from 43th to 85 PND.

• • • •

Hicham et al. (2018)

Body weight loss k Relative adrenal weight gain k Sucrose preference m latency to feed after 24 h of food-deprivation m • time of immobility of stressed rats in the Forced Swimming Tests m • the time spent in open arms in the Elevated Plus Maze test m

Neuroprotective effect from ethanol intoxication

Rat

Male Wistar rats (N 5 50) assigned r&omLy to 3 groups: Control group: untreated (n 5 16); Ethanol group: submitted to adolescent IEI (n 5 17); AO-Ethanol group: supplemented with AO & submitted to adolescent IEI (n 5 17). Rats were 21 days old (at weaning) when AO was administered daily by intragastric gavage (10 mL/kg BW) before, during, & after ethanol administration.

• ethanol intake & preference El Mostafi et al. ratio k (2020) • vulnerability to adolescent IEIinduced voluntary ethanol intake k • controlled the manifestation of ethanol withdrawal signs • anxiogenic-like effect k • Oxidative stress markers (MDA, NO, CAT & SOD) k • neuronal loss in the CA3 hippocampal subregion k • number of neurons per mm2 in the BLA & PrL brain subregions m

Neuroprotection effect from arylamide

Rat

Female Sprague Dawley rats (225
275 g) were exposed to ACR (50 mg/kg i.p. three times a week), AO (6 mL/kg BW orally/day) or together for 30 days, in 4groups (n 5 5): Group 1 (Control), orally gavages with 0.9% NaCl; Group 2, ACR (50 mg/kg i.p. 3 times a week); Group 3, AO (6 ml/kg, p.o. per day); Group 4, ACR 1 AO. At the end of 4 weeks rats were killed by decapitation without stunning.

• ACR-affected cytosolic XO, Aydın (2017) G6PD & GST restored. • Mitochondrial oxidative stress k (MnSOD, GSH, LP & PC restored) • Mitochondrial OXPHOS and TCA enzymes normalised • AChE k • ATP and MTT levels m

Anticonvulsant

Rat

Adult rats (260
280 g, 3 months old) were divided into 4 groups where status epilepticus was induced by pilocarpine (PC, 400 mg/kg i.p.): Group 1, AO plus PC (n 5 20); Group 2, PC plus saline treatment (n 5 20); Group 3, AO pretreated (n 5 10, 1 ml/100 g/day p.o. for 2 months); and Group 4, saline treatment (negative control, n 5 10).

• • • •

latency to first seizures m weight loss k animal survival m lipid peroxidation level in animal hippocampus k • Nitrite content in animal hippocampus k • Hippocampal CAT activity m

Bahbiti et al. (2018)

(Continued)

TABLE 24.2 (Continued) Health-promoting activity

Animal Treatment/model

Outcome

Reference

Nephroprotection

Rat

Male Sprague Dawley rats (N 5 50) were r&omLy assigned to one of 5 equal groups, where all the rats were daily administered orally for 30 days: Control group (dH2O), AO-treated group (6 mL/kg BW), NaF-treated group (20 mg/kg BW), AO pretreated group (pretreatment of AO at 6 mL/kg BW p.o. for 15 consecutive days followed by NaF at 20 mg/kg BW p.o. daily for 30 days.), & AO-NaF co-treated group (NaF, 20 mg/kgBW & AO 6 mL/kg BW p.o. daily for successive 30 days).

• Decreased body weight m Saber et al. (2020) • Elevated BUN & creatinine levels k • Renal oxidative stress biomarkers (SOD, GPx & GSH) mm • Renal TAC level m • Renal MDA concentration k • Increased renal levels of inflammatory markers (TNF-α, IL-1β, NO & IL-10) k • Renal MCP-1, TGF-β1, IL-6, & IL-8 m • Expression of intermediate filament protein genes (desmin, nestin, & vimentin) m

Nephroprotective

Rat

Male albino Wistar rats (N 5 48) were divided into 6 groups (n 5 8) & treated for 3 successive weeks where nephrotoxicity was induced by intramuscular injection of 1 mg/kg betamethasone (BM). The control group was given dH2O p.o. daily; the BM group received BM day after day; AO/0.5 & AO/1 groups received AO (0.5 mL/kg, 1 mL/kg p.o., daily, respectively), BM 1 AO/0.5 group & BM 1 AO/1 group where AO was administered concomitantly with BM.

• Reduced RBCs, Hb, PCV & MCHC m • Increased TWBCs, neutrophils, monocytes & platelets k • Increased serum urea & creatinine levels k • renal MDA & NO levels k • renal GSH content m • improvement in damaged renal tissue architecture • increased Bax/Bcl-2 ratio k • increased caspase-3 k • decreased PCNA m

Orabi et al. (2020)

Oxidative stress

Rat

Wistar rats (200 6 20.18 g, N 5 36) were divided into 6 groups & treated for 21 days daily via oral gavage: Group 1: received dH2O (10 mL/kg BW); Group 2: received Syzygium aromaticum essential oil prepared in AO (100 mg/kg BW); Group 3: received AO (10 mL/kg BW); Group 4: received 1% H2O2 (10 mL/kg BW) with dH2O (10 mL/kg BW); Group 5: received 1% H2O2 (10 mL/kg BW) with Syzygium aromaticum essential oil prepared in AO (100 mg/kg BW); & Group 6: received H2O2 (10 mL/kg BW) with AO (10 mL/kg BW).

• Liver toxicity markers (LDH, ALT & AST) k • Blood urea & creatinine levels k • Prevent H2O2-induced brain congestion • & haemorrhage • Prevent H2O2-induced liver inflammation & binucleation • Prevent H2O2-induced kidney tissue congestion

Bakour et al. (2018)

Anti-inflammation

Mice

Inflammatory paw oedema test were carried out on mices that were divided into 6 groups (n 5 3) where 2 groups received AO p.o., at 5 g/kg & 8 g/kg BW, respectively; 2 groups received unsaponifiable extract of AO at 10 g/kg & 15 g/kg BW, respectively; a control group & a Diclofenac (50 g/kg) group. One hour after oral administration, oedema was induced by the injection of 0.1mL of carrageenan solution (0.5%) into the subplantar region of the right hind paw of all mice. The size of the oedema was measured by a plethysmometer from 1 to 6 h after injection.

• Paw volume k after 5h • Anti-inflammatory activity were slightly stronger than those of reference drug, diclofenac

Menni et al. (2020)

Anti-inflammation

Rat

Adult male Wistar rats (180
220 g) were used in paw edema test performed by experimental trials using two stimuli: chemical stimuli (1% carrageenan in normal saline) (n 5 6) & mechanical stimuli (n 5 6). After the stimuli, all animals fasted for 18 hr before the anti-inflammatory test & received 5 mL of water with gastric gavages. The right hind paw is considered as a control without treatment. Indomethacin was used as control for both groups (n 5 6).

• edema in the first & second phases of carrageenan inflammation k • edema in the different phases of the trauma-induced inflammatory k

Kamal et al. (2019)

Protection of acrylamide-induced tissue injury

Rat

Female Spraque Dawley rats (225
275 g, N 5 20) was divided into 4 groups (n 5 5). Control group received normal saline solution p.o. Experimental groups were treated with ACR (50 mg/kg BW i.p, 3 times a week), AO (6 mL/kg BW p.o., per day) & ACR 1 AO for 30 days.

• Liver & kidney MPO & NOx k Er, Aydın, ˘ • Liver & kidney MnSOD & S¸ ekeroglu, & Atlı ˘ (2020) GPx m S¸ ekeroglu • Cytosolic enzymes m • Tissue injury markers k • GSH m • LP & PC k

Protection of acrylamide -induced toxicity

Rat

Female Sprague- Dawley rats (12
14 weeks old, 225
275 g, N 5 20) • Decreased levels of were divided into 4 groups (n 5 5): Group 1, Control group (1 mL/kg hematological parameters m BW of normal saline); Group 2: ACR was administered i.p. at • Lipid peroxidation & protein 50 mg/kg/day 3 times per week for 30 days; Group 3: AO was carbonyl levels in spleen & administered p.o. at 6 mL/kg per day for 30 days; & Group 4: animals thymus k were treated with ACR (50 mg/kg/day 3 times per week) & AO • GSH levels in almost all the (6 mL/kg/day) together for 30 days until they were euthanized. lymphoid organs m • Increased urinary 8-OHdG k • Decreased MPO levels m • The formation of MN & ME k

˘ S¸ ekeroglu, Aydın, & ˘ (2017) S¸ ekeroglu

• Serum urea, creatinine & uric Male Wistar rats, (6 200 g, 8 weeks old) were divided into 4 groups acid level k (n 5 8). The first group served as the control; second group was given AO (5 mL/kg BW); third group (HgCl2) was given mercuric chloride • Serum IL1, IL6 & TNFα k (0.25 mg/kg BW i.p.); fourth group was given combined treatment • reduced glutathione level, GPx with AO & HgCl2. The treatment of all groups was lasted for & GST m 3 consecutive weeks.

Neciba et al. (2013)

Protection of HgCl2 induced toxicity

Rat

(Continued)

TABLE 24.2 (Continued) Health-promoting activity

Animal Treatment/model

Outcome

Reference

Protection of LPSinduced toxicity

Mice

Swiss OF1 mice (12 to 16 weeks-old) were supplemented with AO prior to injection with bacterial lipopolysaccharide (LPS). Eight groups of mice (n 5 6) received, for 25 days: a standard chow (2 groups, control); a standard chow supplemented with 6% (w/w) AO (2 groups) & a standard chow supplemented with 6% (w/w) olive oil (2 groups). Oils were included in the diets by direct mixing with the standard animal chow.

• increase in circulating glucose levels k • rise in blood TC k • increase in uremia k • SOD activity k • GPx activity m • hepatic TNF-α & IL-6 k • hepatic IL-4 m

El Kamouni et al. (2017)

Prevention of LPSassociated metabolic dysregulation

Mice

Swiss OF1 mice (12
16 weeksold) were divided into 6 groups (n 5 5) & treated for 25 days prior LPS injection: Control groups, a standard chow (2 groups); AO groups, 6% (w/w) AO into standard chow (2 groups); & olive oil groups, 6% (w/w) olive oil into standard chow (2 groups). During the fed state & 16 h before euthanasia, 1 group from each treatments received 100 μg i.p. Escherichia coli 0111:B4 LPS or PBS alone at 5 mg/kg.

• Hepatic PPARα, ERRα, & PGC-1α m • Reduced ACOX1, ACADS (C4:0) & ACADM (C16:0) activities m • PEPCK, G6PH & & Glut4 mRNA m

El Kebbaj et al. (2015)

Immunomodulation & anti-inflammatory

Rat

Adult Albinos Wistar rats were exposed to HgCl2(0.25 mg/kg • Combination of AO 1 Bahi & Necib (2014) BW i.p.) or AO (5 mL/kg BW p.o.), or sodium selenite (Na2SeO3, Na2SeO3 p.o. results in gradual 0.25 mg/kg BW p.o.), or a combination of both, in 8 groups (n 5 8). recovery in phagocytic activity Group 1 is the control group, whereas the remaining groups were • Combination of AO 1 respectively treated with AO (5 mL/kg BW), Na2SeO3 (0.25 mg/kg Na2SeO3 p.o. decreases t1/2 of BW), AO 1 Na2SeO3, HgCl2 (0.25 mg/kg BW), AO 1 HgCl2, carbon in blood • The level of IL1, IL6 & TNFα Na2SeO3 1 HgCl2, and HgCl2 1 AO 1 Na2SeO3. Experimental change in phagocytic activity was determined by injection of restored to near normal carbon ink suspension (0.1 ml/10 g) via the tail vein to each rat.

Immunomodulation

Rat

Adult Albinos Wistar rats were divided into 4 groups: the first served as a control, while the rest as treatment groups that were given AO at dose of: 2.5, 5.0 & 10.0 mL/kg BW, respectively. AO were orally gavaged to the animals 10 days before injection of the carbon ink suspension.

• Phagocytic activity m • Half-time of carbon in blood k

Youcef Necib, Bahi, Zerizer, Abdennour, & Boulakoud (2013)

Immunostimulatory effect against mercuric chloride

Rat

Male Albinos Wistar rats were divided into 4 groups: the first served as a control, while the remaining groups were treated with: AO (0.5 mL/kg BW by gavage), HgCl2 (0.25 mL/kg BW i.p.) & combination of AO & HgCl2. Change in phagocytic activity was determined after 48 h injection of carbon ink suspension.

• Decreased in phagocytic activity m • Increased half-time of carbon in blood k

Youcef Necib, Bahi, & Zerizer (2013)

Colorectal anastomosis

Rat

30 female Wistar Albino rats (250 6 25 g) were divided in 3 groups: Group 1 (sham), laparotomy was performed & the colon was mobilized. In the control (Group 2) & AO (Group 3) groups, colonic resection & anastomosis were applied. To the control & sham groups, 2 mL of 0.9% NaCl was administred rectally, & in the AO group, 2 mL/day argan oil was applied rectally for 7 days.

• mean colonic bursting Barlas et al. (2018) pressure m • colonic tissue hydroxyproline content m • colonic tissue prolidase k • inflammatory cell infiltration k • colonic wound healing m • MDA & FOP levels k • Total sulfhydryl level m

Wound healing effect

Rat

Adult male albino Wistar rats (N 5 30) divided into 5 equal groups: a sham group, a control group (burned but no topical agent), a group in which AO was applied once a day, a group in which AO was applied twice a day, & a group treated with 1% silver sulfadiazine once a day. Second-degree burns were created by scalding hot water (85 C for 15 seconds). Treatment began 24 hours after the burn injury; in the argan oil groups, 1 mL of argan oil was administered via syringe to the wound. The rate of wound healing was quantified by wound measurements on days 1, 7, & 14 after burn injury.

• • • •

TGF-β expression m Healing/contraction m Contraction rate m Greater contraction rate than the positive control, silver sulfadiazine

Avsar et al. (2016)

Key: 8-OHdG, 8-hydroxydeoxyguanosine; ACADL, acyl CoA dehydrogenase long-chain; ACADM, acyl CoA dehydrogenase medium-chain; ACADS, acyl CoA dehydrogenase shortchain; AChE, acetylcholinesterase; ACOX1, acyl-CoA oxidase 1; ACR, acrylamide; ADP, adenosine diphosphate; ALT, alanine aminotransferase; AST, aspartate aminotransferase; ATP, adenosine triphosphate; Bax, Bcl-2-associated X; Bcl-2, B-cell lymphoma-2; BLA, Basolateral amygdala; BM, betamethasone; BUN, blood urea nitrogen; BW, body weight; CAT, catalase; dH2O, distilled water; EDL, extensor digitorium longus; ERRα, estrogen related receptor α; FOP, fluorescent oxidation product; G6PD, glucose 6-phosphate dehydrogenase; G6PH, glucose-6-phosphatase; Glut4, glucose transporter 4; GPx, glutathione peroxidase; GSH, glutathione; GST, glutathione-S-transferases; H2O2, hydrogen peroxide; Hb, hemoglobin concentration; HF, high fat; HNF-4α, hepatic nuclear factor-4α; i.p., intraperitoneally; IEI, intermittent ethanol intoxication; IR, insulin resistance; LDH, lactate dehydrogenase; L-NAME, L-nitroarginine methylester; LOOH, lipoperoxides; LP, lipid peroxidation; LPS, lipopolysaccharide; MCH, mean corpuscular hemoglobin; MCHC, mean corpuscular hemoglobin concentration; MCV, mean corpuscular volume; MDA, malondialdehyde; ME, megakaryocytic emperipolesis; MN, micronucleus; Mn-SOD, Mangan SOD; MPO, myeloperoxidase; MUFA, monounsaturated fatty acids; NADH, nicotinamide adenine dinucleotide; NADPH, nicotinamide adenine dinucleotide phosphate; ND, normal diet; NO, nitric oxide; NOx, NO2 1 NO3 level; OXPHOS, oxidative phosphorylation; p.o., per os/orally; PC, protein carbonyls; PCNA, proliferating cell nuclear antigen; PCV, packed cell volume; PEPCK, phospoenolpyruvate carboxykinase; PGC-1α, peroxisome proliferator-activated receptor γ coactivator-1α; PPARα, peroxisome proliferator-activated receptor α; PrL, prelimbic cortex; PUFA, polyunsaturated fatty acids; RBCs, red blood cell count; RPAT, retroperitoneal adipose tissue; RPAT, retroperitoneal adipose tissue; SBP, systolic blood pressure; SOD, superoxide dismutase; TAC, total antioxidant capacity; TBARS, thiobarbituric acid reactive substance; TC, total cholesterol; TCA, tricarboxylic acid; TG, triglyceride; TWBC, total white blood cell count; XO, xanthine oxidase.

310

24. Biological activities of argan (Argania spinosa L.) oil: Evidences from in vivo studies

et al., 2018). So far, however, the only scientific demonstration of a possible antidiabetic activity, especially diabetes mellitus, has still been in rats. Bnouham et al. (2008) is among the earliest to prove antidiabetic properties of AO in vivo. Samane et al. (2009) attributed diabetic control of AO to the restoration of insulin signaling in fat and liver. Neuroprotection activity is one of the latest research interest in AO for both treatment and prevention of neurodegenerative diseases, particularly Alzheimer’s disease. Just as the other health-promoting effects of AO, the high antioxidant molecules in the oil were hypothesized to contribute to the prevention of neurodegenerative diseases. Neuroprotective potential of AO in neuropsychiatric disorders has most recently been reviewed (ELMostafi et al., 2020). Surprisingly, there is yet to be any preclinical study on the anticancer activity of AO reported, thus far. Amidst all the sensational claims, anticancer and cancer chemoprotective effects of AO remains in the in vitro stage. Again, many assumptions and hypothesis of AO’s anticancer properties are based on the oil’s similarity to olive oil in terms of fatty acid and polyphenol composition. High content of Vitamin E, phytosterol and polyphenol contents in AO have been the basis of AO’s anticancer evaluation. Cancer chemopreventive effects of AO are also expected from the oil due to its high contents of γ-tocopherols, squalene and phenolic compounds. Khallouki et al. (2003) reported that consumption of AO should confer cancer chemopreventive properties due to the unique profile of fatty acids, tocopherols, squalene, sterols, and phenolic compounds in AO. However, anticancer and cancer preventive properties of AO has yet to be proven in vivo. Speculations on the cytotoxic properties of AO are highly associated with the antioxidative compounds reported in the oil. The effectiveness of AO in affecting lipid metabolism is relatively apparent. However, it’s effectiveness in other preclinical studies listed Table 24.2 are not well understood and their mechanism of actions are yet to be explained. Quite revealing is the demonstration that argan oil significantly affects the nuclear receptors peroxisome proliferator activating receptors alpha (PPARα) (El Kebbaj et al., 2015). In lipid metabolism, the stimulation of PPARα increases the synthesis of HDL and Apo A1. In this way, the reverse transport of cholesterol is promoted. In addition to this, PPARγ were also key regulators of lipid and carbohydrate metabolism which is crucial for regulating gene networks involved in glucose homeostasis and inflammation (Varga et al., 2011) which may provide some hints to its efficacy in ameliorating diabetes, immunostimulatory and antiinflammatory activities. El Kebbaj et al. (2015) also found that argan oil can stimulate PPARα and Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PGC-1α) signaling, and help to stimulate the oxidation of fatty acids via the impact of PGC-1α as a coactivator of HNF-4α that preserves gluconeogenesis.

24.4 Biological effects on animal health Traditionally, pressed argan fruits cake was used to feed the cattle and complemented the forage furnished by the leaves and fruits of this same plant (Charrouf & Guillaume, 1999). In ram husbandry, Allai et al. (2015) found that inclusion of 1% (w/w) AO in Tris and 5% (w/w) in skim milk significantly improved sperm viability, progressive motility and

Multiple Biological Activities of Unconventional Seed Oils

24.5 Bioactive compounds contributing to the biological activity of argan oil

311

membrane integrity of ram semen until study endpoint storage at both 5 C and 15 C. The study attributed the positive effects of AO to the corresponding antioxidant effects demonstrated through decreased the level of spontaneous and induced malondialdehyde (MDA) and DNA fragmentation of the sperm. Argan oil was also reported to improved some nonspecific immune parameters, survival rate against the pathogen Lactococcus garvieae, besides increased the growth performance of tilapia when added 1%
2% (w/w) into the diet (Baba et al., 2017). Following escalation of argan oil’s price due to increasing demands as human nutraceutical and cosmetic ingredient, AO have been applied as supplements and an ingredient for coat/ hair/ mane and fur management following the pet industry boom and the existing animal show and sports industry. Otherwise, it would be more practical to valorize byproducts from the oil extraction for applications mend directly for animal feeding and husbandry, considering the elevated price of the oil. Lakram et al., 2019 incorporated detoxified argan press cake into the diet of Alpine goats and found raised amounts of total phenolic compounds and total flavonoids, with antioxidant activity in milk produced.

24.5 Bioactive compounds contributing to the biological activity of argan oil Antioxidants contained in argan oil were continuously reported to contribute to the functionality of AO in human clinical trials (Table 24.3). Two notable compounds that were suggested are unsaturated fatty acids and Vitamin E (α- and γ-tocopherols). It has also been suggested that the balanced ratio of MUFA and PUFA (both B40%) within the total 80% unsaturated fatty acids in AO is the uniqueness that is distinctive from other oils. Most clinical protocols would choose to standardize the argan oil used in the study using the composition of fatty acids and tocopherols. More recent studies would include sterols and phenolic compounds along. A notable property of AO worth mentioning is that their extraction method does not alter either the chemical composition of AO or its physicochemical characteristics (Hilali et al., 2005). Presently, many workers are studying sterols especially schottenol and spinasterol, phenolic compounds and melatonin from AO to further understand and develops the health-promoting properties of the oil. Quite significantly, many clinical trials performed chose olive oil as a comparison to the health-promoting effects of AO. The major difference between argan and olive oil is the large chemical variability often found in olive oil. As the quality of olive oil is dependable on its geographic origins, olive oil’s fatty acid composition and lipophilic antioxidants varies greatly. In contrast, AO’s fatty acid composition and lipophilic antioxidants are much more homogenous and, thus, its nutritional value is less variable. Vitamin E (tocopherols) was mostly suggested to be responsible to the bioactivities studied clinically, mostly due to the detection of a higher plasma content of the vitamin accompanied with lower lipid peroxidation and higher antioxidant status in the plasma of the subjects consuming AO. Tocopherols, in the unsaponifiable fraction of AO are present in a higher proportion compared to olive oil (approximately 3 times), particularly in its γ-isoform. Derouiche et al. (2013) showed a significantly higher Vitamin E and also molar ratio of Vitamin E/ total cholesterol observed in the subjects that consumed AO, suggesting better protection of human plasma against oxidation. They also

Multiple Biological Activities of Unconventional Seed Oils

312

24. Biological activities of argan (Argania spinosa L.) oil: Evidences from in vivo studies

TABLE 24.3 Bioactive compounds potentially contributing to the biological activities of argan oil on human. Studies

Health-promoting Potential attributing effects bioactive compounds

Correlation

Hyperlipidemia

Tocopherols

r2 5 0.8443, P 5 0.0096

Polyphenols

r2 5 0.9913, P , 0.0001

Sterols

r2 5 0.8000, P 5 0.0410

Clinical studies Drissi et al. (2004)

Derouiche et al. (2005)

CVD risk

MUFA and PUFA

N/A

Cherki, Derouiche, Drissi, El Messal, Bamou, Idrissi-Ouadghiri and Adlouni (2005)

Atherosclerosis

Vitamin E (α- & γ-tocopherol)

Significant increase of plasma α-tocopherol

Ould Mohamedou et al. (2011)

Type-2 Diabetes complications

Fatty acid composition

N/A

Antioxidant compounds

N/A

Cardiovascular disease risk

PUFA & MUFA

N/A

Vitamin E

Significant increase in plasma

Haimeur, Messaouri, Ulmann, Mimouni, Masrar, Chraibi, and Disease. (2013)

Dyslipidemia

Unsaturated fatty acids N/A

Monfalouti et al. (2013)

Sour et al. (2012)

Sterols

N/A

Postmenopausal oxidative stress

Vitamin E (γ-tocopherol)

N/A

Tichota et al. (2014)

Dry skin

N/A

N/A

Eljaoudi et al. (2015)

Progression of chronic renal failure

Vitamin E (α-tocopherol)

Significant increase in plasma

Postmenopausal skin degeneration

Linoleic acid

N/A

Unsaponifiable fractions

N/A

Bogdan et al. (2016)

Striaedistensae

N/A

N/A

Ostan et al. (2016)

Inflammageing

N/A

N/A

Essouiri et al. (2017)

Knee osteoarthritis Tocopherols

N/A

Mouhib et al. (2020)

Hepatic steatosis

PUFA

N/A

Tocopherols

N/A

Boucetta et al. (2015)

Polyphenols

Bourdel-Marchasson et al. (2020)

Depression symptoms

N/A

N/A

Derouiche et al. (2013)

Hormonal imbalance (male)

Tocopherols

N/A

N/A, not available.

Multiple Biological Activities of Unconventional Seed Oils

References

313

found a consistent dose-dependent antioxidant effect of tocopherols, polyphenols and sterols, extracted from AO, by measuring the resistance of LDL to oxidation.

24.6 Safety and allergenicity of argan oil The consumption of AO in Morocco since its first report in the 1970s or way before that is a societal norm and therefore its acute and chronic toxicity has been assumed to be none, particularly when orally administered at ordinary doses. Report of toxicity or allergy in currently available controlled clinical trials is rare and uncommon. So far, Ostan et al. (2016) in the RISTOMED study reported one case of adverse effect (bowel discomfort) in the AO intervention group of 35 individuals. No serious adverse event (SAE) or suspected unexpected serious adverse reaction (SUSAR) have been reported in any clinical trials involving AO till date. However, cases of allergic contact dermatitis and anaphylaxis caused by AO have been reported (Astier et al., 2009; De ´ lvarez et al., 2021; Foti et al., 2014; Veraldi, Mascagni, Tosi & Brena, 2016). las Marinas A Due to the increased reach and use of AO worldwide, it should be noted that it is also possible that more cases of AO allergy would be reported in the future.

24.7 Conclusion The use argan oil have been widely accepted worldwide as a healthy oil and a beauty promoting oil. Nowadays, AOs are standardised for their fatty acid, sterols, Vitamin E and phenolic compositions. Increasing clinical studies have been conducted in the last decade to evaluate the health-promoting properties of AO to human health. The application of the oil in the prevention of cardiovascular risk is increasingly proven through human clinical trial where most trials agreed that consumption of 25 mL/day of AO significantly reduced plasma or serum total cholesterol and LDL cholesterol. Almost all human trials concluded that AO enhanced antioxidant status where all subjects experienced significant rise of Vitamin E in blood and reduction in the susceptibility of LDL oxidation. On the other hand, research on antidiabetic, antineurodegeneration, and anticancer properties of AO are still not sufficient to ascertain the clinical potential of the oil. The major active compounds contributing to the health-promoting bioactivities of AO clinically are suggested to be its unique fatty acid composition and Vitamin E.

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24. Biological activities of argan (Argania spinosa L.) oil: Evidences from in vivo studies

¨ nta¸s, C., & Kesbic¸, O. S. (2017). Pre-challenge and post-challenge haemato-immu¨ ., Yılmaz, S., O Baba, E., Acar, U nological changes in Oreochromis niloticus (Linnaeus, 1758) fed argan oil against Lactococcus garvieae. Aquaculture Research, 48(8), 4563
4572. Bahbiti, Y., Ammouri, H., Berkiks, I., Hessni, A. E., Ouichou, A., Nakache, R., & Mesfioui, A. (2018). Anticonvulsant effect of argan oil on pilocarpine model induced status epilepticus in Wistar rats. Nutritional Neuroscience, 21(2), 116
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215. Bakour, M., Soulo, N., Hammas, N., FATEMI, H. E., Aboulghazi, A., Taroq, A., & Lyoussi, B. (2018). The antioxidant content and protective effect of argan oil and Syzygium aromaticum essential oil in hydrogen peroxideinduced biochemical and histological changes. International Journal of Molecular Sciences, 19(2), 610. Barlas, A. M., Kuru, S., Kismet, K., Cavusoglu, T., Bag, Y. M., Senes, M., & Hucumenoglu, S. (2018). Rectal application of argan oil improves healing of colorectal anastomosis in rats. Acta Cirurgica Brasileira, 33(7), 565
576. Bellahcen, S., Hakkou, Z., Ziyyat, A., Legssyer, A., Mekhfi, H., Aziz, M., & Bnouham, M. (2013). Antidiabetic and antihypertensive effect of virgin argan oil in model of neonatal streptozotocin-induced diabetic and l-nitroarginine methylester (l-NAME) hypertensive rats. Journal of Complementary and Integrative Medicine, 10(1), 29
36. Bellahcen, S., Mekhfi, H., Ziyyat, A., Legssyer, A., Hakkou, A., Aziz, M., & Bnouham, M. (2012). Prevention of chemically induced diabetes mellitus in experimental animals by virgin argan oil. Phytotherapy Research, 26(2), 180
185. Bnouham, M., Bellahcen, S., Benalla, W., Legssyer, A., Ziyyat, A., & Mekhfi, H. (2008). Antidiabetic activity assessment of Argania spinosa oil. Journal of Complementary and Integrative Medicine, 5(1). Bogdan, C., Moldovan, M. L., Man, I. M., & Cri¸san, M. J. C. (2016). Preliminary study on the development of an antistretch marks water-in-oil cream: ultrasound assessment, texture analysis, and sensory analysis. 9, 249. Boucetta, K. Q., Charrouf, Z., Aguenaou, H., Derouiche, A., & Bensouda, Y. J. C. I. I. A. (2015). The effect of dietary and/or cosmetic argan oil on postmenopausal skin elasticity. Clinical Interventions in Aging, 10, 339. Bourdel-Marchasson, I., Ostan, R., Regueme, S. C., Pinto, A., Pryen, F., Charrouf, Z., & Durrieu, J. (2020). Quality of life: Psychological symptoms—effects of a 2-month healthy diet and nutraceutical intervention; a randomized, open-label intervention trial (RISTOMED). Nutrients, 12(3), 800. Charrouf, Z., & Guillaume, D. J. J. O. E. (1999). Ethnoeconomical, ethnomedical, and phytochemical study of Argania spinosa (L.) Skeels. Journal of Ethnopharmacology, 67(1), 7
14. Cherki, M., Derouiche, A., Drissi, A., El Messal, M., Bamou, Y., Idrissi-Ouadghiri, A., & Diseases, C. (2005). Consumption of argan oil may have an antiatherogenic effect by improving paraoxonase activities and antioxidant status: Intervention Study in Healthy Men. Nutrition, Metabolism, and Cardiovascular Diseases, 15(5), 352
360. Daoudi, N. E., Bouhrim, M., Ouassou, H., Legssyer, A., Mekhfi, H., Ziyyat, A., & Bnouham, M. (2020). Inhibitory effect of roasted/unroasted Argania spinosa seeds oil on α-glucosidase, α-amylase and intestinal glucose absorption activities. South African Journal of Botany, 135, 413
420. ´ lvarez, M. D., Martorell Calatayud, C., Castillo Ferna´ndez, M., Alvarin˜o Martı´n, M., Fe´lix De las Marinas A Toledo, R., Pineda de la Losa, F., & Martorell Aragone´s, A. J. J. I. A. C. I. (2021). Anaphylaxis after the epicutaneous application of argan oil. Journal of investigational allergology & clinical immunology, 31(4). Derouiche, A., Cherki, M., Drissi, A., Bamou, Y., El Messal, M., Idrissi-Oudghiri, A., & Adlouni, A. (2005). Nutritional intervention study with argan oil in man: effects on lipids and apolipoproteins. Annals of Nutrition and Metabolism, 49(3), 196
201. Derouiche, A., Jafri, A., Driouch, I., Khasmi, M. E., Adlouni, A., Benajiba, N., & Benouhoud, M. (2013). Effect of argan and olive oil consumption on the hormonal profile of androgens among healthy adult Moroccan men. Natural Product Communications, 8(1), 1934578X1300800112. Drissi, A., Girona, J., Cherki, M., Goda`s, G., Derouiche, A., El Messal, M., & Masana, L. (2004). Evidence of hypolipemiant and antioxidant properties of argan oil derived from the argan tree (Argania spinosa). Clinical Nutrition, 23(5), 1159
1166. El Kamouni, S., El Kebbaj, R., Andreoletti, P., El Ktaibi, A., Rharrassi, I., Essamadi, A., & Nasser, B. J. I. J. O. M. S. (2017). Protective effect of argan and olive oils against LPS-induced oxidative stress and inflammation in mice livers. International Journal of Molecular Sciences, 18(10), 2181.

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9. Hicham, E., Tariq, T., Abderrahim, L., Bilal, E., Ali, O., Aboubake, E., & Abdelhalim, M. (2018). Argan oil supplementation reverses anxiety and depressive-like behaviors, neurodegeneration and oxidative stress in amygdala induced by chronic mild stress in rats. Journal of Depression and Anxiety, 7, 319. Hilali, M., Charrouf, Z., Aziz Soulhi, A. E., Hachimi, L., & Guillaume, D. (2005). Influence of origin and extraction method on argan oil physico-chemical characteristics and composition. Journal of Agricultural and Food Chemistry, 53(6), 2081
2087. Hine, D., Mackness, B., & Mackness, M. (2012). Coincubation of PON1, APO A1, and LCAT increases the time HDL is able to prevent LDL oxidation. IUBMB Life, 64(2), 157
161. Kamal, R., Kharbach, M., Vander Heyden, Y., Doukkali, Z., Ghchime, R., Bouklouze, A., & Alaoui, K. (2019). In vivo anti-inflammatory response and bioactive compounds profile of polyphenolic extracts from edible Argan oil (Argania spinosa L.), obtained by two extraction methods. Journal of Food Biochemistry, 43(12)e13066. Khallouki, F., Younos, C., Soulimani, R., Oster, T., Charrouf, Z., Spiegelhalder, B., & Owen, R. J. E. J. O. C. P. (2003). Consumption of argan oil (Morocco) with its unique profile of fatty acids, tocopherols, squalene, sterols and phenolic compounds should confer valuable cancer chemopreventive effects. European Journal of Cancer Prevention, 12(1), 67
75. Lakram, N., Mercha, I., El Maadoudi, E. H., Kabbour, R., Douaik, A., El Housni, A., & Naciri, M. (2019). Incorporating detoxified Argania spinosa press cake into the diet of Alpine goats affects the antioxidant activity and levels of polyphenol compounds in their milk. International Journal of Environmental Studies, 76(5), 815
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1675. Mouhib, M., Benhilal, A., & Ouazane, R. (2017). Argan oil improves dyslipidemia of metabolic syndrome: Human interventional study. Insights in Nutrition and Metabolism, 1(2), 56
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148. Orabi, S. H., Allam, T. S., Shawky, S. M., Tahoun, E. A. E.-A., Khalifa, H. K., Almeer, R., & Mousa, A. A. (2020). The antioxidant, anti-apoptotic, and proliferative potency of argan oil against betamethasone-induced oxidative renal damage in rats. Biology, 9(11), 352. Ostan, R., Be´ne´, M., Spazzafumo, L., Pinto, A., Donini, L., Pryen, F., & Bourdel-Marchasson, I. (2016). Impact of diet and nutraceutical supplementation on inflammation in elderly people. Results from the RISTOMED study, an open-label randomized control trial. Clinical Nutrition, 35(4), 812
818. Ould Mohamedou, M., Zouirech, K., El Messal, M., El Kebbaj, M., Chraibi, A., & Adlouni, A. (2011). Argan oil exerts an antiatherogenic effect by improving lipids and susceptibility of LDL to oxidation in type 2 diabetes patients. International Journal of Endocrinology, 2011. Saber, T. M., Mansour, M. F., Abdelaziz, A. S., Mohamed, R. M., Fouad, R. A., & Arisha, A. H. (2020). Argan oil ameliorates sodium fluoride
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383. Varga, T., Czimmerer, Z., & Nagy, L. (2011). PPARs are a unique set of fatty acid regulated transcription factors controlling both lipid metabolism and inflammation. Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1812(8), 1007
1022. Veraldi, S., Mascagni, P., Tosi, D., & Brena, M. J. D. (2016). Allergic contact dermatitis caused by argan oil. Dermatitis, 27(6), 391.

Multiple Biological Activities of Unconventional Seed Oils

C H A P T E R

25 Biological activities of evening primrose oil Haroon Elrasheid Tahir1, Gustav Komla Mahunu2, Abdalbasit Adam Mariod3,4, Zou Xiaobo1 and Newlove A. Afoakwah5 1

School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China Department of Food Science & Technology, Faculty of Agriculture, Food and Consumer Sciences, University for Development Studies, Tamale, Ghana 3Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 4College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia 5Department of Food Science & Technology, University for Development studies, Tamale, Ghana 2

25.1 Introduction Evening primrose (Oenothera biennis L.), belongs to the family Onagraceae, is a wild plant which widely utilized as medicine and now it is one of the most frequently utilized herbal medicines in many countries (Montserrat-de la Paz et al., 2014; Munir et al., 2017). The evening primrose oil (EPO) has gained great attention due to the high concentrations of γ-linolenic acid (8%
14%) and linoleic acid (60%
80%), precursors of the series-1 prostaglandins (Mahboubi, 2019; Montserrat-de la Paz et al., 2014). Fig. 25.1 shows the flower, seed, and EPO products. Many studies have demonstrated the efficacy of EPO in the treatment of diseases such as atopic eczema (Bamford et al., 2013), breast problem (Balci et al., 2020), antineuropathic activity (Rock & DeMichele, 2003), rheumatoid arthritis (RA) (El-Sayed et al., 2014), antioxidant activity (Koo et al., 2010), anticancer (Montserrat-de la Paz et al., 2015), and other diseases (Mahboubi, 2019; Munir et al., 2017). These effects are mostly attributed to polyunsaturated fatty acids (PUFAs) of EPO. Besides these triacylglycerol fractions, other specific compounds (e.g., triterpenoid esters) existing in EPO might have a significant role in these positive effects (Knorr & Hamburger, 2004; Zaugg, Potterat, et al., 2006).

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25. Biological activities of evening primrose oil

FIGURE

25.1

Evening

primrose

products.

EPO Flowers

EPO capsules

EPO Oil EPO seeds

EPO-Efamol

25.2 Biological activities 25.2.1 Treatment of rheumatoid arthritis Many trials have demonstrated that EPO can play a significant role in the treatment of inflammation and RA (Belch & Hill, 2000; Hauben, 1994; Horrobin, 1989). About 1% of the population of adults suffering from RA (Tyagi et al., 2020). RA is an autoimmune-mediated joint-based chronic inflammation ailment and more prevalent among women than in men (Abdulkhaleq et al., 2018). Up to now, the medicine of RA is still beyond our reach and inflammatory mediators are controlled by using artificial antiinflammatory compounds. Nowadays, the therapeutic protocols for inflammatory disease are steroidal (corticosteroids), nonsteroidal antiinflammatory drugs (NSAIDs), disease-modifying antirheumatic drugs, biological drugs, and natural agents (Burmester & Pope, 2017; Tyagi et al., 2020). Recently, plant
extracted bioactive compounds have also been used for the treatment of RA disorder. Traditionally, EPO has been utilized for many biological activities and reported in the literature. The therapeutic effect of EPO is attributed to its various bioactive compounds such as linoleic acid, (gamma) linolenic acid, and vitamin E (Kleijnen, 1994). A study was conducted on 40 patients with RA and upper gastrointestinal injuries as a result of nonsteroidal antiinflammatory drugs joined a prospective 6 months double-blind placebo-controlled study of dietary supplementation with γ-linoleic acid 540 mg/day (Brzeski et al., 1991). A treatment group (90 patients) received EPO (6 g/day) while the control group (21 patients) received olive oil 6 g/day (placebo). During this study, no participant stopped the nonsteroidal antiinflammatory medication; however, three participants in each group lower their dose. The findings indicated that only 23% of the treatment group could lower their NSAID dose and none could stop, similar to that observed in the control group. This contrary to the previous work (Belch et al., 1988) where the same treatment of EPO allowed 25% to stop and a further 38% to reduce their NSAID dosage after six months without

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25.2 Biological activities

319

negative effects. Although that study continued for 12 months, most of the positive effects were achieved at 6 months. The participates in that trial have less severe RA and none was no one second-line therapy. This study showed that EPO could be only useful in mild RA while some earliest studies showed there no positive results of EPO (Darlington & Stone, 2001; Hansen et al., 1983). In the study of Brzeski et al. (1991), EPO showed a decrease in morning stiffness and articular index, although only the former obtained statistical significance. The authors do not recommend EPO for severe RA. Furthermore, the study has not demonstrated the potential of substituting EPO for NSAIDs in participants with NSAID-induced upper gastrointestinal side-effects. In a clinical study on RA with γ-linoleic acid in the form of EPO, it was observed that the patients were enhanced without side effects (Leventhal et al., 1993). Cytokines aid from free radicals is accountable for the development and maintenance of RA. Some prostaglandins suppress cytokine formation. Thus, EPO, which provides γ-linoleic acid, the precursor of prostaglandin E1, ameliorates arthritic symptoms (Darlington & Stone, 2001). In a study, the consumption of fish oil alone or enriched with EPO showed higher incorporation of n-3 PUFA precursors for the antiinflammatory lipid mediators in plasma phospholipids (Veselinovic et al., 2017). This further prompt substantial enhancement in the clinical status of patients with RA disease. The authors suggested further trials with a large number of participants for a long period to approve the long-term effectivity of these supplementations. Several small studies in animals have suggested benefits from EPO for rheumatoid treatment. In a study on animals (n 5 114), arthritis was induced by subcutaneous injection of complete Freund’s adjuvant (CFA) in the right hind paw of male albino rats. All treatments were administered orally from day 0 (EPO, 5 g/kg b.w.) or day 4 (celecoxib, 5 mg/kg; aspirin, 150 mg/kg) until day 27 after CFA treatment (El-Sayed et al., 2014). The results showed that EPO substantially depressed synovial hyperplasia and inflammatory cells invasion in joint tissues and the result was improved by combining with aspirin or celecoxib. This study showed that the combined use of EPO, which contains antiangiogenic, antiinflammatory, and antioxidant activities, is a promising approach to inhibit the development of RA.A systematic overview of 11 medical studies evaluated the use of oil rich in γ-linolenic acid (GLA) (including borage seed oil, blackcurrent seed oil, and EPO) revealed that it showed significantly lower pain as compared with placebo (Stonemetz, 2008). In a meta-analysis of seven clinical studies oils from borage, blackcurrant, and EPO containing GLA were used to treated RA. GLA dosages equal or bigger than 1400 mg/day presented benefits in the mitigation of rheumatic complaints while doses lower than 500 mg/day were ineffective (Cameron et al., 2009). In Cochrane updated systematic review of 22 studies investigated the use of herbal therapies in RA (Cameron et al., 2011). Results from seven studies specify the potential positive effect of GLA from EPO, borage seed oil, or blackcurrent seed oil, concerning reduce pain severity (Cameron et al., 2011).

25.2.2 Treatment of Mastalgia Approximately 70% of women complain of breast pain at some stages of their life (Ader& Browne, 1997). Cyclic breast pain or Mastalgia is a common condition among

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25. Biological activities of evening primrose oil

women of reproductive ages. It occurs due to changes in hormones during the menstrual cycle, whereas noncyclical breast pains are not related to the menstrual period (Gautam et al., 2016). The deficiency in GLA causes the breast tissues sensitive to sex hormones, which is accompanying by breast pain (Graham et al., 1994). Parveen et al. (2007) compared the effect of Danazol and EPO on the management of cyclic breast pain. The findings showed that Danazol provides good pain management in mastalgia however with severe adverse effects, whereas OEP also presented better Mastalgia control but without severe adverse effects. Another study on the effect of EPO and vitamin E on the severity of cyclical breast pain was conducted by Fathizadeh et al. (2009). The findings indicated that EPO reduced the severity of pain and it was more beneficial and better than vitamin E. Other authors combined EPO and vitamin E for treating cyclical mastalgia (Pruthi et al., 2010). The results indicated that the daily doses of 1200 IU vitamin E, 3000 mg EPO or the combination of both treatments at the same dosage administered for 6 months might decrease the severity of periodical breast pain. Randomized clinical trial administered on 90 participants complaining of Mastalgia showed (Jaafarnejad et al., 2017). The results evidence the use of flaxseed powder, EPO, or vitamin E may decrease cyclical breast pain, and the former achieved statistical significance. Since flaxseed powder was more effective compared to the other two treatments. Therefore, the authors recommended using this herbal medicine which is characterized by the higher content of omega-3 essential fatty acids, contains phytoestrogens and antioxidants, due to its fewer adverse effects. In contrast to the study carried out by Farzaneh et al. (2016) who found the use of flaxseed powder, EPO, and vitamin E lead to a reduction in the severity of mastalgia; however, there were no significant differences among the three treatments. In a study, 120 participants were divided into four groups and treated with: (1) EPO and control oil, (2) fish oil and control, (3) fish and EPO, or (4) both control oils for six months (Blommers et al., 2002). Overall, EPO and fish oil had no better effect than the inexpensive wheat-germ oil and corn oil. Several research articles and reviews have demonstrated the potential use of EPO for the management of mastalgia with good response and minimal side effects (Balci et al., 2020; Cheung, 1999; Farzaneh et al., 2013; Mirzaiinajmabadi et al., 2017; Morvarid et al., 2020; Qureshi & Sultan, 2005) while some trials showed no significant effect (Goyal & Mansel, 2005; Sharma et al., 2012). Table 25.1 summarizes some clinical trials on EPO in the treatment of mastalgia.

25.2.3 Antiinflammatory activity Patients with inflammatory diseases generally use complementary and alternative medicine, particularly herbal therapy. In a study, sterols were extracted from the EPO and accounted for about 49.40% from other fractions and nearly 1% from EPO. These results showed that the EPO is one of the richest sources of phytosterols as compared with other oils such as corn oils (0.95%), sunflower (0.73%), and olive oil (0.17%) (Montserrat-de la Paz et al., 2012; Richard et al., 2002). In a study, the ability of sterols extracted from EPO to impede the release of some proinflammatory mediators by cells involved in inflammation like macrophages was evaluated (Montserrat-de la Paz et al., 2012). The results showed that the extracted sterols may exert a substantial protective effect against the release of proinflammatory mediators. Multiple sclerosis is the most chronic inflammatory

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25.2 Biological activities

TABLE 25.1

Some clinical studies on EPO in the treatment of mastalgia.

Trial/ailments

Intervention

Results

References

Prospective clinical trial

Participants (n 5 66) received six EPO capsule (240 mg/d GLA) for 6 months

Cheung (1999)

Double-blind placebo-controlled parallel multicenter clinical trial

Participants (n 5 555) were treated with 500 mg EPO (providing 40 mg GLA) plus 10 mg natural vitamin E. Placebo fatty acid capsule contained 500 mg hydrogenated coconut oil and 10 mg natural vitamin E. The active antioxidant vitamin and mineral capsule contained 3 mg betacarotene, 100 mg vitamin C, 25 mg vitamin B6, 10 mg zinc, and 10 mg niacin, and 455 μg selenium. Placebo antioxidant vitamin and mineral capsule contained 255 mg of fractionated coconut oil.

• Results showed EPO as the source of Gamolenic acid could be used for treatment for Oriental women with disturbing cyclical mastalgia. • An overall useful response rate was 97% after 6 months of intervention. • Adverse effects was12% but all were insignificant. No effectiveness of EPO in mastalgia

Randomized doubleblind

Participants (n 5 50) were treated • Piroxicam gel: excellent response with Piroxicam gel 0.5%, twice a day (56%), substantial response or 505 mg twice daily EPO, for 3 (35%), poor response (8%) months. • EPO capsule: substantial response (64%), poor response (32%). • Only one participant reported adverse effects with OEP to include abdominal bloating, nausea, weight gain, headache, depression, giddiness, rash, and bad taste. The patients (15
35 years old) were • Results proved Danazol to be treated with 500 mg EPO (n 5 50 significantly effective (76%) in the patients) or 100 mg oral danazol treatment of mastalgia as (n 5 50 patients), twice daily, for 3 compared to 68% effectiveness of months. The effect of treatment was EOP, which is relatively assessed at baseline 4 and 12 weeks comparable. However, the higher after treatments. adverse effect of Danazol (32%) hinders it is used for the treatment of mastalgia and encourages the usage of EPO due to its lower adverse effect (%). • Adverse effects of EPO were 20% while for Danazol was 24%.

Open nonrandomized comparative clinical study

Goyal and Mansel (2005)

Qureshi and Sultan (2005)

Parveen et al. (2007)

(Continued)

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25. Biological activities of evening primrose oil

TABLE 25.1 (Continued) Trial/ailments

Intervention

Results

Randomized clinical study

Participants treated with 2.5 mg Response to treatment 63.9% versus Saied et al. bromocriptine plus 3 mg EPO 82.5% (2007) (n 5 36) daily, LILT (n 5 40), for three consecutive menstrual cycles.

Single-blind clinical study

Participants received 3 g EPO (n 5 31) or 600 mg vitamin E (n 5 30) daily, for one month

Double-blind randomized placebo controlled trial

Patients were treated with 400 IU vitamin E (n 5 21), 1000 mg EPO (n 5 21), the combination of vitamin E (4001 U) and EPO (1000 mg) (n 5 21), or placebo (two capsules) (n 5 22) three times daily, for 6 months.

Quasirandomized clinical trial

Participants received 30 g of powdered flaxseed (n 5 28), 1000 mg capsules of EPO (n 5 28), 400 IU Vitamin E (n 5 30), daily, for 2 months.

• The severity of cyclical breast pain in both groups reduced significantly before and after the treatment. • Reduction in pain severity 61.3% versus 26.7% The results showed that EPO, vitamin E, and the combination of the dosage of vitamin E and EPO could be used to manage cyclical breast pain.

References

Fathizadeh et al. (2009)

Pruthi et al. (2010)

flaxseed powder significantly Jaafarnejad decreased the breast pain during et al. (2017) the two months of treatment, but despite reducing the duration of pain in the EPO group and Vitamin E, this reduction was not significant

Double-blind Participants treated 2 g/day EPO Vitamin E and EPO presented randomized placebo- (n 5 25), 400 IU/day vitamin E similar therapeutic effect in the controlled trial (n 5 25), EPO plus vitamin E (n 5 25), treatment of mastalgia placebo (n 5 25) daily, for 6 month

Alvandipour et al. (2011)

A randomized, Participants treated with EPO 3 g/ double-blind factorial day (n 5 68), centchroman 30 mg controlled trial (n 5 67) for 6 months

Sharma et al. (2012)

The results showed that the centchroman providing relief from mastalgia and nodularity with minimal side effects

disorder. Rezapour-Firouzi et al. (2013) evaluated the effect of EPO on multiple sclerosis patients. The results showed that EPO treatment has inhibited multiple sclerosis and numerous other inflammatory disorders. In another study, the long-chain fatty alcohols (LCFAs) of EPO demonstrated it is in vitro antiinflammatory effect (Montserrat-de la Paz et al., 2014). It is clear from the above-mentioned two studies both LCFAs and sterols are minor biological active compounds that might synergize the activity ascribed to the PUFAs of the EPO assisting to the overall antiinflammatory influence of this natural biologically active product. In a recent study, an attempt has been made to discover new antiinflammatory therapy to recover remyelination and possibly prevent and reverse the development of the disease (Rezapour-Firouzi et al., 2020). The results demonstrate the potential therapeutic properties on the improve the structure of cell membranes and suppression of inflammation by EPO in experimental autoimmune encephalomyelitis.

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In a double-blind, randomized trial, the activity of liver enzymes in multiple sclerosis participants treated with cosupplemented hemp seed, EPO, and hot-natured diet were assessed (Rezapour-Firouzi et al., 2014). The findings showed that the cosupplemented oil chemical components have positive effects on enhancing extended disability status score and activity of liver enzymes in relapsing-remitting multiple sclerosis patients. The active components of EPO have been shown to have antiinflammatory activities and effects. Another study was conducted to assess the effects of EPO and hemp seed oil on enhancing the membrane fatty acids composition of spleen and blood cells and immunologic factors in comparison to rapamycinin the experimental autoimmune encephalomyelitis model (Rezapour-Firouzi et al., 2020). The results showed EPO alone presents a targeted treatment for remyelinate whereas the combination of EPO and hemp seed oil suppresses any attempt for remyelination.

25.2.4 Antioxidant activity Antioxidant activity is one of the functional properties that EPO can provide. Oils rich with biologically active agents are desirable by consumers, food processors, and pharmaceuticals. EPO is rich in sources of GLA (8%
10%) and linoleic acid (LA) (70%
74%) and it is assumed that this compound activity is the major contributing factor to the therapeutic assistance of this oil (Timoszuk et al., 2018). De La Cruz et al. (1999) were studied the influence of enrichment (15% wt./wt.) of a hyperlipemic diet (1.33% cholesterol) with EPO for six weeks in 10 rabbits. The results demonstrated that the EPO might be useful as an antioxidant defense factor, and possibly reducing lipid substances, in processes of hyperlipemia or atherosclerosis. However, further trials in humans are required to prove that EPO presents a similar action in less aggressive forms of hyperlipemia such as that examined in these experimental animals. In a study, the antioxidant effect of saponified EPO against isobutylmethylxanthine (IBMX)-induced melanogenesis in B16 melanoma cells was examined (Koo et al., 2010). In their study, saponified EPO successfully decreased melanogenesis in B16 melanoma cells and reduced pigmentation of UV exposed skin. It was concluded that saponified-EPO exhibits a pigment-whitening effect by preventing the expression of tyrosinase and associated enzymes; consequently, the authors believed that this action might be associated with the high concentrations of linoleic acid in EPO. In experimental animal, it has been demonstrated that both EPO and fish oil, can affect papilloma development which can be attributed, at least in part, to their capability to inhibit benzo(a)pyrene binding to DNA and to increase the lipid peroxidation process (Ramesh & Das, 1998). Another study on thoroughbred horses showed that EPO is useful and it enables horses to compensate with the maximal load without substantial disruption of the musculoskeletal. The study indicated that intake of EPO (150 mL/horse) significantly influenced aspartate aminotransferase and lactate dehydrogenase in the blood serum of the horses. However, this result needed further experiments to prove the usage of EPO as an effective agent for the improvement of the health condition of horses in load (Mikesova et al., 2014). In the year 2011, the antioxidant activity of EPO in cases of subacute aflatoxin intoxication induced in mice was studied (Kanbur et al., 2011). It was found that EPO has a significant positive effect on aflatoxin-induced lipid peroxidation.

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Hamburger et al. (2002) studied the compounds with radical scavenging, cyclooxygenase, and neutrophil elastase inhibitory activities in EPO. The results showed EPO rich in biologically active materials such as 3-O-trans-caffeoyl derivatives of betulinic, morolic, and oleanolic acid. These identified compounds evident antioxidant activity against the stable 2,2-diphenyl-1-picrylhydrazyl radical and were effective inhibitors of neutrophil elastase and cyclooxygenase-1 and -2 in vitro. The authors found that the commercial samples of EPO presented only traces of these biologically active materials. Thus, cold-pressed EPO is recommended to be used as a supplementary agent. Khodeer et al. (2020) investigated the chemoprotective effects of EPO against the cytotoxicity of chemotherapeutics in the liver and pancreas of cyclophosphamide-intoxicated mice. It was noticed that EPO has strong antioxidant, antiinflammatory, and genoprotective properties against the toxic impacts of cyclophosphamide in mice hepatic and pancreatic tissues. In human patients, it was observed that oral administration of the combination of EPO, vitamin C, vitamin E, and pycnogenol significantly prevented wrinkle development produced by chronic ultraviolet B irradiation (UVB) through significant inhibition of UVB-induced mitogen-activated protein activity along with improvement of collagen synthesis. In a previous study, the efficacy of EPO against arsenic-induced oxidative stress in rats was investigated (Kaya & Eraslan, 2013). EPO did not show any side effect and even prevented oxidative stress when administered in association with arsenic. Hence, the authors suggested that the applied dosage (0.1 mL/rat/day) and study period (30 days) are determined accurately, EPO might be employed either to assist primary therapy or directly for prophylaxis or as a food additive in intoxication cases with arsenic or circumstances where such a risk arises.

25.2.5 Anticancer and antitumor activity From the past years, the utilization of herbal medicines for the prevention and management of cancer has gained great attention. Nowadays, it has been found that GLA is cytotoxic to glioma cells, and it can improve gamma radiosensitivity (Antal et al., 2015). A previous study indicated that EPO (as a source of GLA) may be beneficial in nutritional methodologies of mammary gland tumor therapies (Mun˜oz et al., 1999). In 2015, it was reported for the first time that EPO phytosterols might be involved in phytosterolactivated liver X receptor (LXR) serving a cancer-protective role (Montserrat-de la Paz et al., 2015). In this study, the effect of phytosterols (namely, β-sitosterol and campesterol) isolated from EPO on proliferation, cell death, and the cell cycle of human colon adenocarcinoma (HT-29) cells was evaluated. The results demonstrated that the extracted phytosterols were effective antiproliferative mediators in a dose- and time-dependent manner, with an IC50 of 62.9 μg/mL after 48 h, lower than β-sitosterol and campesterol (79.0 and 71.6 μM respectively). Flow cytometry revealed that the extracted phytosterols have a stimulatory effect on apoptosis and necrosis, raising the number of cells in G0/G1 phase. The extracted phytosterols generated a significant upregulation in LXR gene expression that could be one of the basic mechanisms of the tumor reduction by EPO phytosterols.

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25.2.6 Preventing and treatment of pain Fibromyalgia is a chronic pain disease that is described by the existence of mechanical hyperalgesia and prevalent pain consistently felt in deep tissues (Montserrat-de la Paz et al., 2013). Besides pain, patients also commonly complain of other symptoms such as fatigue, sleep disorder, and illness like irritable bowel RA, and systemic lupus erythematosus (Wolfe et al., 1990). In a study conducted on experimental animals showed that dietary-EPO can change the nociceptive response and other symptoms related to fibromyalgia syndrome and also it can decrease the release of the inflammatory state (Montserratde la Paz et al., 2013).

25.2.7 Antiulcerogenic effects Benefits of plant oil from their recorded medicinal uses as antiulcerogenic and gastroprotective properties (Azab et al., 2017). In 1997, the effect of EPO on a study on gastric ulceration and secretion induced by many ulcerogenic and necrotizing mediators in rats was evaluated. It was found that EPO has substantial antiulcer and cytoprotective effects on numerous experimentally prompted (aspirin or indomethacin) gastric lesions (Al-Shabanah, 1997).

25.2.8 Thrombolytic activity Oils have numerous biological active agents that have antithrombotic activity (Deng et al., 2001; Mekhfi et al., 2012). Villalobos and coauthors found that the dietary supplementation with EPO the antithrombotic capability of the endothelium, decreased subendothelial thrombogenicity, and reduced the extent of vascular wall lesions resulting from the hyperlipemic diet (Villalobos et al., 1998).

25.2.9 Antibacterial activity Lodhia et al. (2009) compared the antibacterial of EPO with palmarosa oil, lavender oil, and tuberose oil. Various levels of each oil ranging from 10% to 100% were examined. The results demonstrated that the lower concentrations of EPO have more effect on gramnegative conversely higher concentration presented more effect on gram-positive bacteria.

25.2.10 Antidiabetic activity The global incidence of cases of diabetes mellitus has been increased rapidly (102.9%) (Liu et al., 2020). Many medicines are available for the management of diabetes mellitus; however; no perfect therapy has been reported yet. The herbal remedies are thought to provide better management of diabetes by enhancing the immunity of the body. A study of the antidiabetic activity of EPO was conducted by Takahashi et al. (1993). These results suggest that EPO treatment is beneficial in enhancing abnormal lipid and thromboxane (TX) A2 metabolism in diabetic patients. Gestational diabetes occurs during pregnancy. It can affect pregnancy and the baby’s health. After giving birth, gestational pregnancy returns to a normal level rapidly. In the

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clinical study, the efficacy of 1000 mg EPO and 1000 IU vitamin D (n 5 30) by comparison with placebo for six weeks on women with gestational diabetes was assessed on biochemical parameters at baseline and after treatment. Treatments with EPO and vitamin reduced in serum high sensitivity C-reactive protein level and malondialdehyde significantly, whereas the increase in plasma nitric oxide and total antioxidant activity level was detected in the combination of EPO and vitamin D as compared with the placebo group. Thus, women with gestational diabetes can use EPO as a source of natural antioxidant compounds (Jamilian & Afshar, 2017; Jamilian et al., 2016). Recently, a study was carried out to evaluate the potential use of EPO as an antiinflammatory, antioxidant, and vasodilating effect in type 2 diabetic patients (Safaa Hussain et al., 2016). In this study, the first group (n 5 13) treated with metformin (500 mg) tablets twice daily alone, and the second group (n 5 13) treated with the combination of metformin (500 mg) and EPO (2 mg) capsule twice daily for three months treatment. The outcome of the study showed that early treatment with EPO with traditional hypoglycemic drugs could enhance therapeutic benefits and represent a good protocol to control the increase of diabetes complications. Another study on rats conducted to evaluate the effects of 14 days of oral administration with EPO (1.25 g/kg) and was compared to that of alpha-lipoic acid (ALPA) (100 mg/kg) and insulin (2 IU/day), administered individually or in a mixture (El-kossi et al., 2011). Compared with control diabetic rats, the combination of EPO and ALPA enhanced glycemic control, lipid abnormalities, and antioxidant activity; therefore recover the damaged functional properties of peripheral nerves greatly.

25.2.11 Treatment against kidney disorders In 2009, the effects of EPO on calcium oxalate urinary stone risk factors in eight black and eight white healthy male (treated with 1000 mg EPO daily for 20 days while following a free diet) was investigated (Rodgers et al., 2009). It was reported that citraturia increased substantially in each group. Urinary oxalate revealed a trend to decline in the black group. Calciuria and the Tiselius risk index reduced significantly in each group. Carryover effects were detected.

25.2.12 Atopic eczema/dermatitis Since 1980, great attention had been given to natural plant oil extract as a potential substitute to topical corticosteroids for the management of atopic dermatitis (Lovell et al., 1981; Wright & Burton, 1982). Although EPO was previously approved in the United Kingdom as medicine for atopic dermatitis, marketing approval was withdrawn in 2002 due to the lack of confirmation of effectiveness (Bayles & Usatine, 2009). In an earlier study, patients with atopic dermatitis were randomized to treated with EPO, EPO plus fish oil, or placebo for 16 weeks (Berth-Jones & Graham-Brown, 1993). No enhancement with active treatment was proved. In 1994, reports showed that EPO does not affect atopic dermatitis (Berth-Jones & Graham-Brown, 1994). In 2008, a randomized placebo-controlled study exhibited a significant difference in the outcome of treatment between the EPO group and the placebo group. No significant adverse effect was observed by any

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patient/guardian at any stage of evaluation (Senapati et al., 2008).A meta-analysis indicated that EPO (efamol) positive effect on itch, pruritis, crusting, edema, and redness (erythema) that becomes apparent between 4 and 8 weeks after treatment is started. Nevertheless, the extent of this influence decreases in relation with the increasing rate of potent steroid use (Morse & Clough, 2006). There are numerous review articles on the effectiveness of EPO alone or along with other oils on atopic eczema (Bamford et al., 2013; Kerscher & Korting, 1992). A recent review concluded that treatment with EPO significantly improved atopic dermatitis as compared to the placebo and is presently suggested for management of atopic dermatitis (Schlichte et al., 2016). The previous review, published in 2012, had demonstrated no strong evidence of the effect of EPO in eczema, and they cannot be recommended for the public or for clinical practice at that time (Bath-Hextall et al., 2012). Overall, some studies showed that EPO is a nontoxic and effective treatment for atopic dermatitis, however, since there are some conflicting results further large trials are required.

25.2.13 Antineuropathic activity It was reported that breast cancer survivors who have been treated with adjuvant chemotherapy might experience suffer from late effects of chemotherapy, namely, congestive heart failure, neuropathy, premature menopause, and osteoporosis. The study conducted by Rock and DeMichele (2003) showed that EPO is beneficial for patients suffering from chemotherapy-induced neuropathy. Patients who received EPO showed enhancements in nerve function assessments and symptoms.

25.2.14 Hypocholesterolemic activity In a study, the hypocholesterolemic effects of Oenothera biennis Linn oil, EPO, bioγ-linolenic acid oil, safflower oil, palm oil, and soybean in cholesterol-fed rats was evaluated (Fukushima et al., 1997). The findings demonstrated that EPO prevents the increase of serum total cholesterol and very-low-density lipoprotein, intermediate-density lipoprotein, and low density-cholesterol concentrations in the existence of surplus cholesterol in the diet after 13 weeks of treatment. Later systematic and meta-analysis of randomized clinical trials found that the oral administration of EPO at a dose of # 4 g/day considerably decreases serum triglyceride concentration and substantially increases high-density lipoprotein concentration in hyperlipidemic subjects (Khorshidi et al., 2020). The authors suggested that large-scale and high-quality clinical studies are needed to demonstrate the efficiency of EPO on lipid profile levels. Also, further studies can apply a higher dosage of EPO and expand the study period.

25.2.15 Antiretroviral activity Numerous patients who are treated with antiretroviral drugs also utilize alternative medicine involving dietary supplements such as EPO. A systematic review was carried out to explore the evidence for dietary supplement interactions with antiretrovirals

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(Jalloh et al., 2017). This review showed that the EPO significantly increases the levels of antiretrovirals and patients should be examined for side effects whereas taking EPO with antiretrovirals. Furthermore, this review indicates the importance of monitoring all human immunodeficiency virus patients for dietary supplement receive to avoid treatment failure or side effects associated with an interaction.

25.3 Conclusion This chapter has shown there is increasing scientific data for the utilization of dietary supplement of EPO as an integral part of the management of many diseases such as atopic eczema, cancer, antitumor activity, inflammatory, and prevention or treatment of pain. Although EPO has been utilized for centuries for much treatment of diseases, further studies regarding its effectiveness need to be strengthened. This does not mean that the effectiveness is insufficient, but it does mean that further studies are required to be completed.

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´ ngel-Martı´n, M., Pe´rez-Camino, M. C., & Ferna´ndez Arche, A. Montserrat-de la Paz, S., Garcı´a-Gime´nez, M. D., A (2014). Long-chain fatty alcohols from evening primrose oil inhibit the inflammatory response in murine peritoneal macrophages. Journal of Ethnopharmacology, 151(1), 131
136. Morse, N. L., & Clough, P. M. (2006). A meta-analysis of randomized, placebo-controlled clinical trials of Efamol evening primrose oil in atopic eczema. Where do we go from here in light of more recent discoveries? Current Pharmaceutical Biotechnology, 7(6), 503
524. Morvarid, I., Sedigheh, S., Khadivzadeh, T., Masoumeh, G., & Fatemeh, N. S. (2020). Comparative evaluation of evening primrose oil and vitamin E on the severity of cyclic mastalgia: A systematic review and metaanalysis. The Iranian Journal of Obstetrics, Gynecology and Infertility, 23(3), 91
98. Munir, R., Semmar, N., Farman, M., & Ahmad, N. S. (2017). An updated review on pharmacological activities and phytochemical constituents of evening primrose (genus Oenothera). Asian Pacific Journal of Tropical Biomedicine, 7(11), 1046
1054. Mun˜oz, S. E., Piegari, M., Guzma´n, C. A., & Eynard, A. R. (1999). Differential effects of dietary Oenothera, Zizyphus mistol, and corn oils, and essential fatty acid deficiency on the progression of a murine mammary gland adenocarcinoma. Nutrition (Burbank, Los Angeles County, Calif.), 15(3), 208
212. Parveen, S., Sarwar, G., Ali, M., & Channa, G. A. (2007). Danazol vs oil of evening primrose in the treatment of mastalgia. Pakistan journal of surgery, 23(1), 10
13. Pruthi, S., Wahner-Roedler, D. L., Torkelson, C. J., Cha, S. S., Thicke, L. S., Hazelton, J. H., & Bauer, B. A. (2010). Vitamin E and evening primrose oil for management of cyclical mastalgia: A randomized pilot study. Alternative Medicine Review: A Journal of Clinical Therapeutic, 15(1), 59
67. Qureshi, S., & Sultan, N. (2005). Topical nonsteroidal anti-inflammatory drugs vs oil of evening primrose in the treatment of mastalgia. The Surgeon: Journal of the Royal Colleges of Surgeons of Edinburgh and Ireland, 3(1), 7
10. Ramesh, G., & Das, U. N. (1998). Effect of evening primrose and fish oils on two stage skin carcinogenesis in mice. Prostaglandins, Leukotrienes, and Essential Fatty Acids, 59(3), 155
161. Rezapour-Firouzi, S., Arefhosseini, S. R., Ebrahimi-Mamaghani, M., Baradaran, B., Sadeghihokmabad, E., Torbati, M., Mostafaei, S., Chehreh, M., & Zamani, F. (2014). Activity of liver enzymes in multiple sclerosis patients with Hot-nature diet and co-supplemented hemp seed, evening primrose oils intervention. Complementary Therapies in Medicine, 22(6), 986
993. Rezapour-Firouzi, S., Arefhosseini, S. R., Mehdi, F., Mehrangiz, E.-M., Baradaran, B., Sadeghihokmabad, E., Mostafaei, S., Fazljou, S. M. B., Torbati, M.-A., Sanaie, S., & Zamani, F. (2013). Immunomodulatory and therapeutic effects of Hot-nature diet and co-supplemented hemp seed, evening primrose oils intervention in multiple sclerosis patients. Complementary Therapies in Medicine, 21(5), 473
480. Rezapour-Firouzi, S., Mohammadian, M., Sadeghzadeh, M., & Mazloomi, E. (2020). Effects of co-administration of rapamycin and evening primrose/hemp seed oil supplement on immunologic factors and cell membrane fatty acids in experimental autoimmune encephalomyelitis. Gene, 759144987. Richard, E., Ostlund, J., McGill, J. B., Zeng, C.-M., Covey, D. F., Stearns, J., Stenson, W. F., & Spilburg, C. A. (2002). Gastrointestinal absorption and plasma kinetics of soy Δ5-phytosterols and phytostanols in humans. American Journal of Physiology-Endocrinology and Metabolism, 282(4), E911
E916. Rock, E., & DeMichele, A. (2003). Nutritional approaches to late toxicities of adjuvant chemotherapy in breast cancer survivors. The Journal of Nutrition, 133(11 Suppl. 1), 3785s
3793s. Rodgers, A., Lewandowski, S., Allie-Hamdulay, S., Pinnock, D., Baretta, G., & Gambaro, G. (2009). Evening primrose oil supplementation increases citraturia and decreases other urinary risk factors for calcium oxalate urolithiasis. The Journal of Urology, 182(6), 2957
2963. Safaa Hussain, M., Abdulridha, M. K., & Khudhair, M. S. (2016). Anti-inflammatory, anti-oxidant, and vasodilating effect of evening primrose oil in type 2 diabetic patients. International Journal. of Pharmaceutical Sciences Review and Research, 39, 173
178. Saied, G. M., Kamel, R. M., & Dessouki, N. (2007). Low intensity laser therapy is comparable to bromocriptineevening primrose oil for the treatment of cyclical mastalgia in Egyptian females. Tanzania Health Research Bulletin, 9(3), 196
201. Schlichte, M. J., Vandersall, A., & Katta, R. (2016). Diet and eczema: A review of dietary supplements for the treatment of atopic dermatitis. Dermatology Practical & Conceptual, 6(3), 23
29. Senapati, S., Banerjee, S., & Gangopadhyay, D. N. (2008). Evening primrose oil is effective in atopic dermatitis: A randomized placebo-controlled trial. Indian Journal of Dermatology, Venereology and Leprology, 74(5), 447
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Sharma, N., Gupta, A., Jha, P. K., & Rajput, P. (2012). Mastalgia cured! Randomized trial comparing centchroman to evening primrose oil. The Breast Journal, 18(5), 509
510. Stonemetz, D. (2008). A review of the clinical efficacy of evening primrose. Holistic Nursing Practice, 22(3), 171
174. Takahashi, R., Inoue, J., Ito, H., & Hibino, H. (1993). Evening primrose oil and fish oil in non-insulin-dependentdiabetes. Prostaglandins, Leukotrienes, and Essential Fatty Acids, 49(2), 569
571. Timoszuk, M., Bielawska, K., & Skrzydlewska, E. (2018). Evening primrose (Oenothera biennis) biological activity dependent on chemical composition. Antioxidants (Basel, Switzerland), 7(8), 108. Tyagi, V., Singh, V. K., Sharma, P. K., & Singh, V. (2020). Essential oil-based nanostructures for inflammation and rheumatoid arthritis. Journal of Drug Delivery Science and Technology, 60101983. Veselinovic, M., Vasiljevic, D., Vucic, V., Arsic, A., Petrovic, S., Tomic-Lucic, A., Savic, M., Zivanovic, S., Stojic, V., & Jakovljevic, V. (2017). Clinical benefits of n-3 PUFA and ɤ-Linolenic acid in patients with rheumatoid arthritis. Nutrients, 9(4). Villalobos, M. A., De La Cruz, J. P., Martı´n-Romero, M., Carmona, J. A., Smith-Agreda, J. M., & de la Cuesta, S. F. (1998). Effect of dietary supplementation with evening primrose oil on vascular thrombogenesis in hyperlipemic rabbits. Thrombosis and Haemostasis, 80(10), 696
701. Wolfe, F., Smythe, H. A., Yunus, M. B., Bennett, R. M., Bombardier, C., Goldenberg, D. L., Tugwell, P., Campbell, S. M., Abeles, M., Clark, P., Fam, A. G., Farber, S. J., Fiechtner, J. J., Michael Franklin, C., Gatter, R. A., Hamaty, D., Lessard, J., Lichtbroun, A. S., Masi, A. T., . . . Sheon, R. P. (1990). The american college of rheumatology 1990 criteria for the classification of fibromyalgia. Arthritis & Rheumatism, 33(2), 160
172. Wright, S., & Burton, J. L. (1982). Oral evening-primrose-seed oil improves atopic eczema. Lancet, 2(8308), 1120
1122. Zaugg, J., Potterat, O., Plescher, A., Honermeier, B., & Hamburger, M. (2006). Quantitative analysis of antiinflammatory and radical scavenging triterpenoid esters in evening primrose seeds. Journal of Agricultural and Food Chemistry, 54(18), 6623
6628.

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26 Biological activities of Sclerocarya birrea kernel oil Abdalbasit Adam Mariod1,2 and Haroon Elrasheid Tahir3 1

Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 2College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia 3School of Food and Biological Engineering, Jiangsu University, Zhenjiang, P.R. China

26.1 Introduction The marula tree is a large tree with circular branches. It is 13 meters high, and some may reach 20 meters. The light yellow fruit has a diameter of 3
4 cm. The fruit has a simple hard rind and a juicy, mucous flesh. Marula fruits are wild edible fruits. It is a fruit with a large amount of sweet sour juice and contains a brown seed that is very hard and difficult to break except with a sharp bale. The kernel has a smooth white core 1.0
1.5 cm long and 0.5
0.75 cm wide. The marula tree produces very large numbers of more than thousands of fruits annually (Mariod et al., 2005). The bark of the mariola tree has a rough, light gray mottled, with pale brown spots. The leaves are dark green the leaf is 60 mm long. The flowers are small with yellow petals and red sepals, and the males are separated from the females. The tree often produces fruits with a diameter of 3 cm. They are green and turn yellow when ripe. The weight of the ripe fruit is between 15 and 25 g. The fruit begins in the summer and usually settles in the winter (Mariod & Abdelwahab, 2012). The marula fruit contains one young seed that itself contains 2
3 edible kernels with a creamy taste similar to the taste of sweet almonds (Fig. 26.1). The approximate analysis of the kernel shows that it contains 53.0%, 28.0%, and 8.0% of oil, protein, and carbohydrates, respectively. It is noted that the percentage of oil in the kernel is very high, and thus marula is an important source of oil and protein and is suitable for commercial exploitation, as in some countries such as South Africa (Mariod et al., 2005). Mariod et al. (2005) examined marula kernel oil samples collected from western Sudan, and studied the physical and chemical properties of the extracted oil. The results of the study were that, the specific gravity was 0.9224, the color of the oil was slightly pale

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FIGURE 26.1 Sclerocarya birrea tree and fruits. Source: https://commons.wikimedia.org.

yellow, the refractive index was 1.4685, and the value of saponification was 193.54, while the percentage of nonsaponifiable substances was 0.72, the acid value was 05.16, the iodine value of the oil was 64.20, and its phosphorus content was 0.110. The results of the study concluded that, marula kernel oil is considered an edible oil with high stability and is a rich source of important fatty acids such as mainly conjugated linoleic acid, which is used as an antioxidant, anticancer, and antiatherogenic effect. Deep chemical analysis of the marula nucleus content of the minerals showed that it contains high levels of copper, magnesium, and zinc. The results also indicated that 36.4% of the dry weight of the kernel was protein, which contained relatively low levels of lysine, phenylalanine, leucine, and threonine amino acids. Fatty acids also formed a high percentage in the kernels, with oleic acid accounting for more than 70%, followed by linoleic acid, which represented 24% of the fatty acid weight (Glew et al., 2004). A study showed that the tocopherol content of marula kernel oil was affected by the oil storage time, as it was observed that the total tocopherol level decreased by 25.0% (Mariod et al., 2008). Mariod et al. (2004) clarified that marula oil contains 13.7 mg/100 g of tocopherol and that gamma-tocopherol represents the majority of the component as 95% of tocopherols, and that tocopherols are minor components responsible for the stability of the oil and that the sterols content in the oil was 286.6 mg/100 g. Sitosterol is the predominant type, and 16% of the total sterols were 5-avenasterol, and the study also showed that this type of sterols act to strengthen cells and act as an antipolymerization agent in frying oils (Mariod et al., 2004).

26.2 Marula oil uses and biological activities Sclerocarya birrea oil is extracted from the kernel of the marula tree, and this oil is characterized by its moisturizing properties as it is quickly absorbed by the skin, and it does not leave greasy or shiny effects, because it is rich in fatty acids, which dermatologists say it calms dry skin. The reason why marula oil contains a good percentage of antioxidants,

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and because of its natural antibacterial properties, applying this oil topically to cuts and scrapes may help sterilize wounds and reduce the chances of their infection, by preventing any germs or pollutants from entering the body through these wounds.

26.2.1 Antioxidant and antibacterial activity of marula oil Marula oil contains monounsaturated fatty acids, tocopherol, and amino acids. Therefore it is said to offer many benefits for skin, hair, and health. Besides the use of marula oil, many other parts of the marula tree are used in folk medicine and for cooking purposes in Africa. Marula oil has many properties such as: antioxidant properties, antifungal properties, and antiaging properties. Therefore it helps moisturizing the skin and protecting it from drying out, prevent premature aging, reducing scars and spots, treating weak and cracked nails, and improve hair health. Mariod et al. (2006) studied the antioxidant effect of marula kernel oil cake methanolic extract using magnetic stirring and the contents of the total phenolic compounds in the extract were determined. The antioxidant activity of the extracts was evaluated according to the carotenoid and linoleic acid assay, as the extracts and their parts showed a significant effect. Also, when the extracts were added to sunflower oil at a temperature of 70 C in the dark and compared with a widely used synthetic antioxidant and the effect of this on the oxidative stability of the oil, it became clear that the addition of the extracts was better than the synthetic antioxidant for a specific period. This oil has antimicrobial properties. Hence, it may be effective against bacteria that contribute to the formation of pimples and blackheads. Marula oil also has analgesic and antiinflammatory properties. Therefore it may help reduce the inflammation, redness, itching, and dryness associated with acne. The antibacterial effects of marula seed kernel oil from different harvest periods were investigated. The results of the study showed that this oil has a high ability at different harvest dates to inhibit methicillin-resistant Staphylococcus aureus, P. aeruginos, and E. coli. These results also indicated that this oil has low antibacterial activity against these three bacterial strains compared to fungi (Mariod et al., 2010). Brominated vegetable oil has extensively been used as a food additive in soft drink manufacture, where it has been used as an emulsifying agent. The brominated marula oil showed a broad spectrum activity against E. coli, Salmonella sp., Staphylococcus aureus, and Streptococcus epidermidis microorganism which gave the inhibitions zones of 19.50 mm, 20.50 (Ibrahim et al., 2020). Marula oil may act as an effective moisturizer for dry or aging skin as it absorbs quickly. Ethnomedicinal reports have indicated that marula nut oil has been used for moisturizing and hydrating the skin (Komane et al., 2015). It is also said to be beneficial for treating acne, blurring fine lines, and preventing stretch marks from appearing. The nongreasy property of marula oil may help treat different types of acne and can be used as a good moisturizer for oily skin.

26.2.2 Antiaging activity of marula oil Marula oil has the natural ability to fight various signs of aging. It helps prevent and treat the damage caused by aging skin. Certain enzymes such as: elastase and collagenase

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accelerate the appearance of signs of aging these enzymes can be inhibited by marula antioxidants (Shoko et al., 2018). Marula oil blocks the activity of these enzymes to protect the skin from losing its youth and elasticity. Therefore it may help fight signs of aging such as: fine lines, wrinkles, dryness, and a lack of skin elasticity. It may also increase skin’s natural ability to renew and repair cells on its own. Marula oil can penetrate deeply into the skin, even in thicker areas. The oil’s content of fatty acids and polyphenols improves skin elasticity when used regularly. Thus it may help enhance skin health and appearance. There is also some scientific evidence that marula oil (with the help of some other ingredients) may help treat cuts and scars and prevent blemishes. So it has the power to make skin flawless smooth.

26.2.3 The role of marula oil in protecting against environmental damage Marula oil may protect the skin from the harmful effects of environmental elements such as harsh sunlight, cold winds, and pollution. It is also said to aid in the skin’s natural regeneration process to reverse damage from environmental factors. Marula oil is high in linoleic (an essential omega-6 fatty acid) and oleic acid. Hence, it has many skin moisturizing properties. This means that it can help prevent and treat a variety of skin conditions such as: psoriasis, eczema, and acne. However, there is no direct evidence to prove this. It is said that the abundance of oleic acid in marula oil makes it suitable for all skin types. Where oleic acid is an active ingredient in skin repair. Marula oil is an extremely absorbent oil that does not clog the skin’s pores. Aside from all skin types (dry, oily, and normal), it is also suitable for sensitive skin. Men can also use it to soften their rough skin due to its moisturizing properties. Some studies have indicated the ability of marula oil to aid in wound healing, due to its antiinflammatory effect. Also, the oil contains fatty acids, which make it extremely moisturizing, which helps fight inflammation and redness

26.3 Conclusion The marula tree is one of the African trees of great economic importance, the marula fruits contain most of the important biological components, the kernel contains a high percentage of oil and protein, and its oil is considered to be of great biological importance because it contains oleic and linoleic acids higher than most of the known edible oils, in addition to the presence of micro-components such as tocopherols, sterols, and phenolic compounds, which make it have biological properties such as being antibacterial, antiinflammatory, and others.

References Glew, R. S., VanderJagt, D. J., Huang, Y. S., Chuang, L. T., Bosse, R., & Glew, R. H. (2004). Nutritional analysis of the edible pit of Sclerocarya birrea in the Republic of Niger (Daniya, Hausa). Journal of Food Composition and Analysis, 17(1), 99
111. Ibrahim, J. S., Adamu, H. M., & Shakede, O. I. (2020). Antibacterial activity of marula (Sclerocarya birrea) and brominated marula seed oil. International Journal of Innovative Science and Research Technology, 5(8), 1120
1124.

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Komane, B., Vermaak, I., Summers, B., & Viljoen, A. (2015). Safety and efficacy of Sclerocarya birrea (A.Rich.) Hochst (Marula) oil: A clinical perspective. Journal of Ethnopharmacology, 176, 327
335. Available from https:// doi.org/10.1016/j.jep.2015.10.037. Mariod, A., Ali, A. O., Elhussein, S., & Hussien, I. (2005). Quality of proteins and products based on Sclerocarya birrea (marula) seed. Journal of Science and Technology, 6(1), 0-0. Mariod, A., Mattha¨us, B., & Eichner, K. (2004). Fatty acid, tocopherol and sterol composition as well as oxidative stability of three unusual Sudanese oils. Journal of Food Lipids, 11(3), 179
189. Mariod, A., Mattha¨us, B., Eichner, K., & Hussein, I. H. (2008). Long-term storage of three unconventional oils. Grasas y aceites, 59(1), 16
22. Mariod, A. A., & Abdelwahab, S. I. (2012). Sclerocarya birrea (Marula), an African tree of nutritional and medicinal uses: A review. Food Reviews International, 28(4), 375
388. Mariod, A. A., Mattha¨us, B., Eichner, K., & Hussein, I. H. (2006). Antioxidant activity of extracts from Sclerocarya birrea kernel oil cakes. Grasas y Aceites, 57(4), 361
366. Mariod, A. A., Matthaus, B., Idris, Y. M., & Abdelwahab, S. I. (2010). Fatty acids, tocopherols, phenolics and the antimicrobial effect of Sclerocarya birrea kernels with different harvesting dates. Journal of the American Oil Chemists’ Society, 87, 377
384. Shoko, T., Maharaj, V. J., & Naidoo, D. (2018). Anti-aging potential of extracts from Sclerocarya birrea (A. Rich.) hochst and its chemical profiling by UPLC-Q-TOF-MS. BMC Complementary and Alternative Medicine, 18(1), 54. Available from https://doi.org/10.1186/s12906-018-2112-1.

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C H A P T E R

27 Biological activities of Balanites aegyptiaca (Heglig) kernel oil Abdalbasit Adam Mariod1,2 and Essa Mohammed AhmedIsmail3 1

Indigenous Knowledge and Heritage Center, Ghibaish College of Science & Technology, Ghibaish, Sudan 2College of Sciences and Arts-Alkamil, University of Jeddah, Alkamil, Saudi Arabia 3Department of chemistry, College of Science, Sudan University of Science & Technology, Khartoum, Sudan

27.1 Introduction Balanites aegyptiaca Heglig tree, which is characterized by its economic importance besides being a desert tree. It grows abundantly in a similar African desert environment. Heglig is a medium-sized tree, its height ranges from seven to 15 m. It is an evergreen that loses its leaves when drought intensifies, but quickly restores it and spreads in most parts of Africa. It is widely spread in Sudan, where it is found in various types of sandy and clay soils. Heavy and cracked types. Sudan is considered a major producer of Heglig, which is considered one of the resilient trees that suit different climatic conditions, and its root system is deep in the soil, and it is characterized by strong bark that protects them from drought, and its fruits resemble dates (Fadl, 2015). Heglig is a medium-sized tree 7
15 m evergreen that loses its leaves only when severe drought, but quickly restores it blooms. Usually in the two periods of November and April, and bears fruit in December and January, and another period is March and June (Fig. 27.1). India, Pakistan, Iran, and Sudan are considered the main producing countries. Sudan is one of the country’s most producing and using its fruit (laloop) due to the large spread of Heglig trees. The fruits are usually picked after maturity and are similar in shape to dry dates. It grows in clay and sandy soils and needs a lot of water, so it abounds in places of rain. All parts of the tree, including branches, leaves, and stems, are used in various works. The fruit produced by the tree is very important and eaten by humans and has several different benefits and is used in the treatment of many diseases (Chothani & Vaghasiya, 2011).

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FIGURE 27.1 Balanites aegyptiaca tree with fruits. Source: https://commons.wikimedia.org.

FIGURE 27.2 Balanites aegyptiaca dry seeds.

27.2 Economic outlook of Balanites aegyptiaca About 400 tons of Heglig fruits can be produced in the natural forests of Kordofan, Darfur, Blue Nile, and Kassala regions, Sudan. These fruits provide large quantities of ethanol (5 million gallons), carbonic acid (1500 tons), diosgen (1200 tons), oil (13600 tons), seedcake, which is the residue left after extracting oil from the kernel (2400 tons), firewood (200,000 tons), and other waste (2500 tons). The total revenue from these products is about 80,000 million dollars, and the net profits are 25 million dollars. These natural sources of Heglig in Sudan can cover about 50% of the world’s needs of steroids. The inner kernel of the seed (Kurnaka) (Fig. 27.2) after removing its bitterness with water is sold for about 16 dollars, and a sack that contains 22 mL is sold for 352 dollars, and this karnaka is used to increase the sexual ability of men. The saponin extracted from the fruits of the Heglig

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reaches about 95%
98% of the total content of the saponin found in the pulp of the fruit, which is a high percentage. It also proved that these saponin are of high purity and can be used in pharmaceutical industries such as sex hormones, cortisone, and others (Elfeel and Hindi, 2014).

27.3 Balanites aegyptiaca different uses The fruits leaves, stems, and and roots of the Heglig (desert date), are used in soap making in the laundry. The fruit is considered a natural laxative for the stomach, as well as a repellent for worms, and desert date treat indigestion and neurological and psychological diseases. Heglig kernel oil is used in the cosmetic industry and is also used in the treatment of rheumatism, as well as some diseases that affect the reproductive system, sex hormones, infertility, and fertility diseases (Osman-Bashir & Elhussein, 2017). The fruits of the desert dates are a source of alcohol such as ethanol. The ancient Indians used it to treat some skin diseases, such as vitiligo, and nursing mothers ate the fruit of this tree, which resembles dates, but it is bitter in taste to generate milk. The fruits and seeds were used as a laxative, and the leaves were used to treat wounds. The roots were used in folk medicine as a laxative, as well as in stomach diseases, infertility, and epilepsy. The Egyptians used the seeds for intestinal colic, the leaves for treating fever, and the fruits as a repellent for worms. Research has proven the ability of bark extracts of Heglig to kill schistosomiasis snails, but with caution, that bark extract may cause abortion in pregnant women. Research has also proven the ability of desert dates to kill worms and expel them outside the digestive system that infect the digestive system. Because the seeds contain diosgenin, which has a hormone-like effect, it was used as a contraceptive and as an antiinflammatory for the skin, and as a treatment for some cases of diabetics. A researcher also separated two compounds from the desert dates used as an analgesic and antiinflammatory (Azene, 2015).

27.4 Balanites aegyptiaca Heglig as a medicinal tree Medicinal plants differ from others in that they contain active ingredients, which are volatile oils, soaps, oils, carbohydrates, greases, gums, and steroids. Heglig is considered a medicinal plant because it contains these chemicals. Heglig tree is considered one of the most important saponin trees because it contains a significant percentage of saponins in all its parts (leaves, fruits, stems, bark, and roots) (Chothani & Vaghasiya, 2011). The saponins in Heglig act as a natural immune system for the human body. It also prevents cancer, treats heart disease, and treats AIDS. In addition, it lowers cholesterol by absorbing fats from the body in the same way that drugs used to treat cholesterol work, and cholestyramines clean the body of it by throwing it away. It was found that the level of cholesterol is usually low among African tribes who depend on eating natural herbs in their diet despite eating fatty foods rich in cholesterol. Soaps are used recently in the manufacture of detergents, shampoos and are considered the most suitable for their absence of alkaline substances.

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27.5 Chemical composition of Balanites aegyptiaca Heglig The Heglig fruit consists of four parts: the rind, the pulp, the woody layer, and the kernel, and each layer is of great importance and benefit to the human being. It is a woody layer that contains the nucleus, which contains 50% of oils and 50% of protein, as well as a good amount of beneficial acids and carbohydrates (Elfeel and Hindi, 2014). The fruits of Heglig are called (Lalob) eaten fresh. The fruit consists of four parts: the peel, followed by the pulp layer, which contains estimated amounts of sugars and saponins, and then the hard woody layer that breaks to remove the kernel that contains oil content of more than 50%, as well as a high percentage of protein up to 50%. This tree contains active ingredients such as protein, vitamins and mineral salts. It also contains saponins and steroids (Azene, 2015).

27.6 Balanites aegyptiaca seed composition The seed oil is extracted from the seed kernel, which is used in industry (cosmetics) and is used as a food oil and in the treatment of rheumatism, jaundice, influenza and headaches. The oil percentage ranges between 30% and 60%. The residues remaining from the kernel after extracting the oil (kernel cake) is considered a high-protein stock (50%) suitable for humans and animals. The fruits contain oil, protein, sugar, vitamin, mineral salts, soap, and diosgenin. It is also an important source of steroids, and glucomides that have a high foam when dissolved in water and are similar to soap and are used for various hygiene purposes and washing cotton and silk clothes. It is an important source of many steroidal drugs (four steroid products) that are used as an intermediate in the manufacture of sex hormones and are inexpensive compared to those of animal origin. An example of these medical drugs is corticosteroids, and it is also a source of some contraceptives and sex hormones such as progesterone, cortisone and others. This soapy content increases when the fruit is fermented, and when it decomposes, it gives the substance diosgenin used in medicinal drugs (Chapagain & Wiesman, 2005). There is a percentage of sugars in the fruits that are used locally in the manufacture of a kind of sweet called Al-Sirni in South Kordofan, Sudan. It also contains a seedcake from the kernel that can be used to obtain a meal of special nutritional value to strengthen the nursing mothers to generate milk, and it was found that the fruits have an effect on the treatments related to women and obstetrics. The branchlet is used as smoke for the treatment of rheumatism, the bark is used in the treatment of malaria, the extract of the roots in vitiligo, and the bark decoction was used in the treatment of jaundice, and it was found in experiments that it lowers the percentage of uric acid in the blood, meaning it removes the high urea. It is used in dental treatment. The leaves and bark are used as a wound cleanser and a splint for fractures with wounds (Chothani & Vaghasiya, 2011).

27.7 Balanites aegyptiaca kernel oil Balanite oil is extracted from the seed, and used in the cosmetics industry and in the treatment of some diseases. The residues remaining from the kernel after extracting the oil contain high-protein stock for human and animal food (Alexander, 2017). Heglig is a

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medicinal tree that is distinguished by its containment of active ingredients, namely oils, volatile oils, soaps, greases, and dyes. Balanites aegyptiaca seed kernel oil is a vegetable oil because it is extracted from Heglig trees. Vegetable oils, including balanite oil, are of high nutritional value. The kernel of the balanite seed is edible and very useful. It is rich in oil, protein and minerals and has been used for thousands of years (Vonmaydell, 1986). The results of the physical analysis of blanite seed oil showed that the oil content was 45.32%, the specific gravity was 0.90, the refractive index was 1.45%, and the moisture content was 0.04%. The results of the chemical analysis of the oil showed that the saponification value (200.02 mg KOH/g), the acid value (2.14 mg KOH/g), the iodine number (104.39 100/g), the value of the peroxide number (2.95 μg/kg) and free fatty acids (0.82%). The oil quality evaluation test indicated that the percentage of free fatty acids was equal to 0.84%, and the study of the fatty acid composition of the oil using GC-Ms showed; that the oil contains about 47.52% unsaturated fatty acids (Zang et al., 2018). In a study by Elbadawi and others in 2017, they studied the effect of both roasting and boiling processes on the approximate composition of the kernel of Heglig fruits, as well as the physical, chemical and stability properties of the oil extracted from them. The results of the study showed that the roasting process had a significant positive impact on the value of the peroxide number and the stability of the extracted oil; While the boiling process has the opposite effect. In addition, the study showed that the fatty acids present in Heglig oil are linoleic, oleic, and palmitic with a percentage of up to 96%, and they mostly contain alpha and beta-tocopherols. This study concluded that the kernel oil extracted from the roasted Heglig can be used as a natural antioxidant that can enhance the properties of other edible oils by mixing (Elbadawi et al., 2017).

27.8 Biological activities of Balanites aegyptiaca oil Many scientific reports mention the biological activities antioxidant, anticancer, antidiabetic, antiinflammatory, antimicrobial, hepatoprotective, and molluscicidal activities of balanite extracts from desert date. There are new trends in the use of plant pesticides for pest control because they are safe and environmentally friendly, unlike synthetic chemicals. A study was conducted last year by Mokhtar et al. (2021), which aimed to verify the effectiveness of desert date oils against the red flour beetle (Tribolium castaneum Herbst) and to identify the oil chemical compounds by GC, Ms. The oil was extracted by chloroform, hexane, and ethanol and tested on lesions by film residue method with varying doses and different time. The results showed that chloroform had a 100% mortality rate and hexane extract gave a similar effect at the same doses. Also, chloroform extract recorded the lowest lethal dose against the pest and was the most toxic for T. castaneum compared to other extracts. These results indicated that chloroform and hexane extracts have strong insecticidal activity and can be used in grain storage for pest control (Mokhtar et al., 2021). The balanite kernel oil revealed a good inhibition against Candida albicans and Staphyloccous as it is rich in stearic, oleic, and linoleic acids in addition to β-sitosterol, also a virucidal activity of B. aegyptiaca kernel oil against Herpes simplex virus type 1 (HSV1) was reported. The kernel oil of B. aegyptiaca showed an anthelmintic activity against Schistosoma mansoni and Fasciola gigantica (Al Ashaal et al., 2010).

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27. Biological activities of Balanites aegyptiaca (Heglig) kernel oil

27.9 Conclusion Research has confirmed that the fruits of B. aegyptiaca contain 32% protein and a fixed oil between 45% and 46%, and the effective value in the oil made it treat cancerous tumors, and microbes. The oil showed many biological activities.

References Al Ashaal, H., Farghaly, A., Abd El Aziz, M., & Ali, M. (2010). Phytochemical investigation and medicinal evaluation of fixed oil of Balanites aegyptiaca fruits (Balantiaceae). Journal of Ethnopharmacology, 127, 495
501. Alexander, J. A. (2017). Physicochemical and Phytochemical Characterization of Seed Kernel oil From Desert Date (Balanites Aegyptica). Journal of Chemical Engineering And Bioanalytical Chemistry, 2(1). Azene, T. (2015). Balanites (Balanite aegyptiaca) Del., Multipurpose tree a prospective review. International Journal of Modern Chemistry and Applied Science, 2(3), 189
194. Chapagain, B., & Wiesman, Z. (2005). Variation in diosgenin level in seed kernels among different provenances of Balanites aegyptiaca Del (Zygophyllaceae) and its correlation with oil content. African Journal of Biotechnology, 4 (11), 1209
1213. Chothani, D. L., & Vaghasiya, H. U. (2011). A review on Balanites aegyptiaca Del (desert date): phytochemical constituents, traditional uses, and pharmacological activity. Pharmacognosy Reviews, 5(9), 55
62. Available from https://doi.org/10.4103/0973-7847.79100. Elbadawi, S. M. A., Ahmad, E. E. M., Mariod, A. A., & Mathaus, B. (2017). Effects of thermal processing on physicochemical properties and oxidative stability of Balanities aegyptiaca kernels and extracted oil. Grasas Y Aceites, 68(1), 1
7. Elfeel, A. A., & Hindi, S. Z. (2014). Balanites aegyptiaca (L.) Del. var. aegyptiaca seed composition and variability among three different intra-specific sources. Life Science Journal, 11(7), 160
166. Fadl, K. E. M. (2015). Balanites aegyptiaca (L.): A multipurpose fruit tree in Savanna Zone of Western Sudan. International Journal of Environment, 4, 166
176. Mokhtar, M. M., Jianfeng, L., Du, Z., & Cheng, F. (2021). Insecticidal efficacy and chemical composition of Balanites aegyptiaca (L.) Delile seed oils against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae). ChilliJournal of Agricultural Research, 81(1). Available from https://doi.org/10.4067/S0718-58392021000100102, Chilla´n mar. 2021. Osman-Bashir, N. A., & Elhussein, S. A. A. (2017). Variation in the levels of steroidal sapogenins within the mature fruit of Balanites aegyptiaca and among kernels of balanites fruit accessions collected from different geographical localities in Sudan. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 8(1), 768. Vonmaydell, H. J. (1986). Trees and shrubs of the Sahel: Their characteristics and uses (p. 525) Germany: Eschborn, GTZ. Zang, C. U., Jock, A. A., Garba, H. I., & Chindo, Y. I. (2018). Application of desert date (Balanites aegyptiaca) seed oil as potential raw material in the formulation of soap and lotion. American Journal of Analytical Chemistry, 9 (9), 2018.

Multiple Biological Activities of Unconventional Seed Oils

C H A P T E R

28 Factors affecting the quality of produced unconventional seed oils Ying Qian and Magdalena Rudzi´nska ´ Poland Poznan´ University of Life Sciences, Poznan,

List of abbreviations RI IV AV PV AnV TBA FA FFA SFA UFA PUFA MUFA BHA BHT LDL

refractive index iodine value acid value peroxide value anisidine value thiobarbituric acid fatty acid free fatty acid saturated fatty acid unsaturated fatty acid polyunsaturated fatty acid monounsaturated fatty acid butylated hydroxyanisole butylated hydroxytoluene low-density lipoprotein

28.1 Introduction In recent years, unconventional seed oils have attracted increasing research attention due to their diverse tastes and rich nutritional properties. Unconventional seed oil production means that many kinds of seeds and kernels gain more usable value. The global production of apricots was four million tons in the year 2012 and a significant number of the apricot (Prunus armeniaca L.) pit by-products was wasted; however, by dried weight basis, apricot kernels contain 27.2%
61.4% (w/w) of the fruit’s total oil content (Go´rna´s et al., 2017). In Africa, the use of marula (Sclerocarya birrea L.) fruit can be traced back thousands of years, and recent studies have shown that its kernels are as much as 53.0% oil

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28. Factors affecting the quality of produced unconventional seed oils

(Mariod et al., 2010). Sweet cherries (Prunus avium L.) are not only consumed as fresh fruits, but are also processed into jams, canned foods, and juices in large scale, so the pits ´ constitute a considerable by-product (Go´rna´s & Rudzinska, 2016). The oil yield of mature sweet cherry seeds, apple seeds, redcurrant kernels, pomegranate seeds, honeydew seeds, and watermelon seeds is 37.7%, 22.0%, 22.8%, 25.4%, 27.6%, and 28.5%, respectively (Go´rna´s et al., 2017, 2016). The oil yield of these kernels is generally higher than those in the Fabaceae family (at 1.2%
20.2% in dry weight) (Go´rna´s et al., 2018). The unconventional seed oils produced from such by-products can serve as potential dietary sources. The agriculture factors of genotype and species, ambient climate, and temperature, and sowing and harvesting time all affect the synthesis of substances in the plant and its seeds. The majority of unconventional plant oils are produced from seeds, whose nutritional value is thus indirectly affected by these agricultural factors (Sipeniece, Miˇsina, Grygier, ´ et al., 2021; Rudzinska et al., 2017; Miˇsina et al., 2020). The production of oil strongly affects the quality of vegetable oil. A range of extraction solvents and extraction methods are used in the production process, and the levels of bioactive components in vegetable oil, such as total phenols, will change accordingly (Corbu et al., 2020; Mohammad et al., 2019). The refining process reduces the content of free fatty acid (FFA) and oxidation products, but often leads to the loss of biologically active substances (Hakme et al., 2018). Blending oil with plant oils possessing good antioxidant properties can promote antioxidant stability (Mohammad et al., 2019). The storage conditions of seed oils, such as storage time, light, and temperature, directly affect their quality and can promote the formation of oxidation products. Tocochromanols and phytosterols have been found to decrease over storage time (Qian et al., 2018; Wroniak et al., 2016). The nutritional value of vegetable oils is related not only to their physical and sensory parameters but also to their fatty acid (FA) composition, as well as to their content of bioactive compounds. The quality of vegetable oils is usually estimated with physiochemical parameters such as refractive index (RI), iodine value (IV), acid value (AV), and peroxide value (PV). AV and PV represent the degree of rancidity and oxidation of oils, which intuitively reflect the quality of the vegetable oil. IV is related to the degree of unsaturation of oils (Hamm et al., 2013; Carbone & Charrouf, 2004). Tocochromanols, phytosterols, squalene, carotenoids, essential FAs, and so on are widely considered natural bioactive compounds in plant oils (Go´rna´s et al., 2016; Qian et al., 2018; Sipeniece, Miˇsina, Grygier, et al., 2021). Vegetable oils are a good source of FA intake. Seed oils rich in polyunsaturated fatty acid (PUFA) are linked with the health benefits of lowered low-density lipoprotein (LDL) and cholesterol, and especially in hypertensive patients can decrease blood pressure and the risk of cardiovascular heart disease (CHD) (World Health Organization, 2008; Yu et al., 2016). Tocochromanols, including tocopherols and tocotrienols, are efficient natural antioxidants found throughout most of the plant, which can protect unsaturated fatty acids against oxidation (Burton, 1994). Phytosterols are natural compounds found in plants that belong to the group of cholesterol analogs; they are associated with an antipolymerization function and can extend shelf life and reduce LDL cholesterol in some individuals (Moreau et al., 2018). Squalene, caroten´ oid, phenolic, and other bioactive compounds promote human health (Kulczynski et al., 2017; Lou-Bonafonte et al., 2018). In this chapter, factors affecting the quality of unconventional seed oils are summarized.

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28.2 Agricultural factors

347

28.2 Agricultural factors A large number of studies have shown that agricultural factors (climate, ambient temperature, genotype and species, harvest date, etc.) have a great effect on the quality of ´ vegetable oil (Sipeniece, Miˇsina, Grygier, et al., 2021; Rudzinska et al., 2017; Miˇsina et al., 2020). Plant species and genotypes are the primary factors affecting seeds and seed oils. Previous studies have detected squalene and sterols in the kernel oils of 15 apricot cultivated varieties. Nine sterols were found in apricot kernel oils and the predominant sterol in each variety was β-sitosterol, which made up 76%
86%. It is worth noting that the content of individual sterols and squalene varies greatly in different cultivated apricot kernel ´ oils (Rudzinska et al., 2017). Variety and ambient temperature also affect FA composition, which further influences chemical and physical characteristics (Carbone & Charrouf, 2004; Sipeniece, Miˇsina, Grygier, et al., 2021). Sipeniece, Miˇsina, Grygier, et al. (2021), Sipeniece, Miˇsina, Qian, et al. (2021) collected the seeds of three varieties of Japanese quince (Chaenomeles japonica), each August for 4 years (2015
2018). They found that genotype had significant impact on myristic acid (C14:0), oleic acid (C18:1), linoleic acid (C18:2), and linolenic acid (C18:3), and the contents of C18:1, C18:3 and arachidic acid (C20:0) were also affected by temperature in summer. However, when summer ambient temperature was high, the increase in C18:2 content was accompanied by a decrease in C18:1. This may be due to the high temperature being beneficial to the oil yield of seeds, thus affecting FA synthesis. Similar results have been found in rapeseed, sunflower, and linseed oils (Sipeniece, Miˇsina, Grygier, et al., 2021). According to the results of Miˇsina (2020), for the same spices of Japanese quince seed oil, the genotype has a very great effect on FA (especially variation between C18:1 and C18:2) (Miˇsina et al., 2020). It was shown that species had a greater effect on FA than cultivar or other factors (Miˇsina et al., 2020; Sipeniece, Miˇsina, Grygier, et al., 2021). Genotype also affects the range of tocochromanol content and the concentration of individual phytosterols (Miˇsina et al., 2020). Time of sowing and harvesting was another very important factor in agricultural planting and also affects seed quality. Phosphate fertilization is one of the most important ways of ensuring a high grains yield (Mohammad et al., 2019). This study of Mohammad et al. (2019) showed that sowing time has a greater impact on crop nutrients than the use of phosphate fertilizers. The total levels of carotenoids, tocochromanols, and phenols were associated only with sowing time and not with use of phosphate fertilization. The low availability of phosphate fertilizer had no negative effect on the synthesis of these substances. Thus, from a nutritional point of view, sowing time has a greater impact on seeds and plant seed oils (Mohammad et al., 2019). Phenolic contents were also affected by plant ¨ nal, 1991; Pancorbo et al., 2004). variety and genotype (Lux et al., 2020; Nergiz & U The harvest time also affected the composition of FAs, tocopherols, and other bioactive compounds in the seeds. Oil was extracted from marula kernels (Sclerocarya birrea subsp. Caffera) and used to explore the relationship between harvest time on one hand and FA, tocopherol, and phenolic contents of the oils, as well as their antimicrobial activity, on the other. The study observed that levels of palmitic acid (C16:0) and stearic acid (C18:0) dramatically decreased with later harvesting time, while the oleic acid (C18:1) and linoleic

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acid (C18:2) content increased with later harvesting. The levels of α-tocopherols and γ-tocopherols decreased in a clear manner with harvesting date, and σ-tocopherols had even disappeared by the end of harvest time. The total phenolic and flavonoid contents increased with the degree of seed maturity (Mariod & Abdelwahab, 2012).

28.3 Processing and handling of seed oils Seed oil processing involves the storage, preparation, and handling of seed materials, followed by oil pressing, extraction, and refining (Hamm et al., 2013). Appropriate methods can improve the oil yield and enhance the nutritional value of vegetable oil. In addition to the cold-pressed oil, many seed materials are treated before pressing to increase the oil yield. Microwave pretreatment of hazelnuts modified their microstructure, helped the cell wall to rupture, and allowing oil to pass through the permeable cell wall, thus increasing oil yield and the concentration of bioactive compounds. Moreover, by measuring the AV, PV, FA composition, α-tocotrienol content, and oxidation stability, it has been showed that oil from the hazelnuts that underwent microwave pretreatment was of better quality (Uquiche et al., 2008). The extraction method and the solvent used in processing seed oils affect the nutritional value of the oil. Loypimai et al. (2015) used two stabilization methods (steaming and ohmic heating of rice bran) and three extraction methods (immersion stirring, Soxhlet extraction, and enzymatic extraction) combined with an F-test to study the chemical properties and biological activities of different extraction methods and stabilization methods on rice bran oil. It was found that the oil obtained from the rice bran stabilized by steaming and ohmic heating, combined with enzymatic extraction, had the best quality, the lowest value of FFA, the highest level of γ-oryzanol, and strongest total antioxidant activity (Loypimai et al., 2015). The study showed that the choice of processing method can have a positive effect on the quality of seed oils. Both extraction solvent and plant cultivars can affect the antioxidant properties of plant oils. Studies have used 80% and 100% ethanol, methanol, and isopropanol solvent to extract winter melon seed oil to determine the antioxidant ability of the oils, finding that for the same cultivar, high levels of phenol were found in the oil extracted with 80% isopropanol aqueous solution, while the oil extracted with 100% methanol solvent had the strongest ability to 2,2-diphenyl-1-picrylhydrazyl-free radical scavenging ability (Mohammad et al., 2019). Oil refining involves degumming, neutralization, bleaching, and deodorization. Undesirable compounds, such as FFA, gums, waxes, and phosphates, are removed during refining, but some nutrition compounds like sterols and tocopherols are also lost. Most vegetable oil parameters change during refining (Chew et al., 2016). Some researchers have studied the effects of refining on kenaf seed oil (Hibiscus cannabinus). FFAs are generally removed by neutralization (Chew et al., 2016). Pesticide is widely used in modern agriculture and sometimes exists in seed materials. The residue of pesticide is rinsed off by washing (Duijn, 2008) but also removed from crude oil using soap during the neutralization step; the bleaching and deodorization steps can also help (Chew et al., 2016). Pigment oxidation causes oil darkness, and some studies have used the CIELab method to

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28.4 Seed oil storage conditions

349

detect oil pigments. Interestingly, the bleaching and deodorization steps mainly remove the yellow pigments (b* value) and the red pigment (a* value), respectively. 65.3% of total carotenoids were removed by all refining steps. A total of 79.2% hydroperoxides were removed, and PV and total oxidation values decreased from 2.64 to 0.55 mEqO2/kg and 7.70 to 4.51mEq O2/kg, respectively, after refining (Chew et al., 2016). Total phenolic, phytosterol, and tocopherols contents were also reduced. One study has shown that phytosterol content is reduced during refining, and particularly during the neutralization step, ´ by as much as 20% (Rudzinska et al., 2004).

28.4 Seed oil storage conditions Storage conditions, such as packaging, temperature, light, and storage time, are all significant factors affecting the quality of seed oils (Qian et al., 2018; Wroniak et al., 2016; Wroniak & Re˛kas, 2016). Studies have explored the effects of storage time on various components of unconventional oils, showing that AV and FA composition were both stable, while the PV, sterol content, and tocochromanol content clearly decreased during storage. This might be because phytosterols and tocopherols, as natural antioxidation compounds, were consumed during storage (Qian et al., 2018). The total phenolic content of olive oil decreased by 10.62%
27.44% after storage in the dark for 12 months (Torre-Robles et al., 2019). It is interesting that various plant oils had different level of degradation. The phytosterol level of blackcurrants was observed to decrease sharply by 50% after 6 days and by 72% after 12 days. Meanwhile, avocado fruit oil and macadamia nut oil have low sterol degradation, with decrease in only 4%
6% and 5%
6% at 6 and 12 days, respectively. The lowest degradation of tocochromanols was for argan oil (2% at 6 days and 7% at 12 days). On the other hand, avocado fruit oil had lost as much as 58% at 6 days and 71% at 12 days (Qian et al., 2018). The container in which plant oils are held during storage plays an important role and should be hermetic and light proof. The most common packaging for edible vegetable oils on the market is plastic film and glass bottles of different shapes and colors. Brown glass bottles reduce the negative effect of light on the quality of vegetable oils. Glass bottles prevented oxygen permeability, which would otherwise cause accelerated oxidation, as in polyethylene terephthalate bottles (Torre-Robles et al., 2019; Wroniak & Re˛kas, 2016). Under the same storage conditions, the composition of FA and AV was little affected by contact with oxygen. Unlike FA, the PV and sterols were most negatively affected by oxygen contact; tocopherols were also diminished, but less so than sterols by percentage. This might be because tocopherols degraded earlier than sterols to protect the PUFA from oxidation (Wroniak & Re˛kas, 2016). Storage temperature also affects the concentration of tocopherols and PV, but oxygen factor has a greater impact on PV. The storage of oil at 4 C could effectively prevent this loss (Wroniak & Re˛kas, 2016). Vegetable oil exposed to light can cause automatic proto-oxidization, reducing oil quality (Torre-Robles et al., 2019). When vegetable oils were stored under the same temperature and for the same length of time, but with varied light conditions, the total phenol content was decreased only with storage time but there was significant difference as the

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28. Factors affecting the quality of produced unconventional seed oils

light conditions changed. FFA and AV were only slightly affected by light during storage (Torre-Robles et al., 2019). Chlorophyll decreased a little in the dark samples, but totally disappeared from oils exposed to light. Tocopherols, carotenoids, and chlorophyll were all decreased by storage time and reduced more in the oil samples exposed to light. The effect of light on sterols was as important as the effect of oxygen on sterols, both of which most strongly accelerate the decomposition of sterols (Caponio et al., 2005; Torre-Robles et al., 2019; Wroniak & Re˛kas, 2016). In addition to the above factors, it is easy to overlook the existence of metals. Vegetable oil contains trace metal elements, which are indispensable nutrients for the human body. Iron, nickel, and copper have been shown to accelerate autoxidation to further impact on the shelf life of plant oils (Ansari et al., 2008; Konuskan et al., 2019). The quality of seed oils during storage is affected by all these factors, which lead to a decline in quality. Some methods can thus be used to improve the antioxidant capacity of vegetable oils. The PV and anisidine value (AnV) increased with the storage time, while the AV remained stable. Nitrogen can be flushed into the seed oil to inhibit oxidation. However, oil with higher polyenoic FA contents may undergo faster oxidization even with nitrogen flushing (Wroniak et al., 2016). Similarly, antioxidants are often added to industrially produced vegetable oils to extend their shelf life. ´ Rudzinska et al. (2004) selected four antioxidants (BHT, α-tocopherol, ethanolic extracts of rosemary, and green tea) and added them to sunflower oils to further analyze stigmasterol resistance against degradation and formation of its oxidation products. The results demonstrated that the most effective antioxidant in the prevention of stigmasterol degradation is BHT, followed by ethanolic extract of green tea, α-tocopherol, and ethanolic extracts of rosemary. Tocopherols, as natural antioxidants, also effectively inhibited the formation of stigmasterol oxidation products. Meanwhile, the FA composition underwent fewer changes even without oxidation (Caponio et al., 2005; Qian et al., 2018; Wroniak et al., 2016). These results confirm that antioxidants can effectively prevent plant oils from oxidation and extend their shelf life.

28.5 Quality characteristics Determining the physical and chemical characteristics of unconventional oils is a useful way to identify the quality of these oils. RI, IV, AV, and PV are the most often tested index in evaluating oil quality (Carbone & Charrouf, 2004). IV reflects the degree of unsaturation of oil. Lower IV oil contains a smaller number of double bonds and has better oxidative stability. This results in a lower melting point. The RI value depends not only on testing temperature but also on FA composition, and also decreases with the degree of saturation of oils (Carbone & Charrouf, 2004). When measured at temperatures above 40 C, the RI of saturated fatty acid (SFA) increases proportionally to the chain length, while the IR is proportional to the unsaturation of plant oils (Loypimai et al., 2015). FFAs are unesterified form of FA, which represent the acidity level. The formation of some FFAs is associated with enzymatic or microbial hydrolysis during seed harvest and even ripening; the other FFAs are formed during the storage and transportation of crude

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28.5 Quality characteristics

oils (Carbone & Charrouf, 2004). Oxidation of FAs produces peroxide; the main source of oxidation is contact with the air during handling, transport, processing, and especially storage. This creates an off-flavor in the oil (Hamm et al., 2013). The Codex Alimentarius suggests that a good AV in cold-pressed and refined oils is 4.0 mg KOH/g oil and 0.6 mg KOH/g oil, respectively, and that the PV should not exceed 10 mEq O2/kg oils in refined oil and 15 mEq O2/kg oils in cold-pressed oil (Codex, 2005). Based on previous studies, the physical and chemical properties of selected vegetable oils are summarized in Table 28.1 (Codex, 2005; Chew et al., 2017; Qian et al., 2018; Rokosik et al., 2020). Table 28.1 summarizes the reagent data and all of the cold-pressed oils. The AV of wheat germ oil (5.60 mg KOH/g), borage oil (8.27 mg KOH/g), grape seed oil (4.10
7.80 mg KOH/g), hemp seed oil (6.67 mg KOH/g), and dill seed oil (6.60 mg KOH/g) were all exceeded than the limit of Codex Alimentarius suggestion (4.0 mg KOH/g oil). The PV of black cumin oil (65.40 mEq O2/kg oils), blackcurrant oil (29.81mEq O2/kg oils), and wheat germ oil (18.65 mEq O2/kg oils) was over 15 mEq O2/kg oils, the maximum recommended by the Codex Alimentarius. In cold-pressed vegetable oil, high AV means more FFA in the oils, probably due to its high-water content; hydrolysis makes oils more prone to rancidity during handling. Compared to refined oil, cold-pressed oil lacks neutralization and the other refining processes, so high-quality raw materials should be used (Sahu et al., 2020). TABLE 28.1 seed oil

a

Iodine-value, refractive index, acid value and peroxide value of selected unconventional

Oil

IVb (g/100 g)

RI (at 20 C)

AV (mg KOH/g oil)

PV (meq O2/kg oils)

Argan kernel oil

114.72

ND

0.95

4.30

Black cumin seed oil

128.04

1.47

1.99

65.40

Blackcurrant seed oil

162.81

ND

2.01

29.81

Borage seed oil

143.76

ND

8.27

8.28

Camelina seed oil

171.27
177.03

ND

0.51
0.89

1.10
2.07

Chia seed oil

218.41

1.48

0.68

0.10

Dill seed oil

193.35

ND

6.60

12.84

Grape seed oil

114.72
126.60

1.47

4.10
7.80

13.83
14.84

Milk thistle seed oil

112.41
119.30

1.47

2.15
8.34

1.17
4.20

Poppy seed oil

145.16

1.48

1.03
3.05

0.30
0.78

Walnut oil

145.6

ND

0.40
0.52

1.34
5.87

Wheat germ oil

155.52

ND

5.60

18.65

Hemp seed oil

197.80

ND

6.67

10.07

The data in Table 28.1 were summarized from relevant research (Gao et al., 2019; Gu¨naErgo¨nu¨l & AksoyluO¨zbek, 2018; Meddeb et al., 2017; Qian et al., 2018; Raczyk et al., 2016; Rokosik et al., 2020; Sabudak, 2007; Yilmaz et al., 2019). b IV was summarized from relevant research and calculated based on FA composition according to Nikolaos and Theophanis method (Kyriakidis & Katsiloulis, 2000). a

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28. Factors affecting the quality of produced unconventional seed oils

In addition to the physical and chemical indicators, which are often tested above, melting point, mineral acidity, soap density, viscosity, solubility, AnV, Crismer value, and other parameters can also be used to evaluate oil quality.

28.6 Fatty acid composition Triacylglycerols are the main compounds in vegetable oil, accounting for more than 95% of the oil. These consist of a glycerol backbone connected to three FA acyls (Qian et al., 2020). FAs can be divided into SFAs, monounsaturated fatty acids (MUFA), and PUFAs, depending on the number of double bonds. Vegetable oil is also a significant means of providing dietary essential FAs, such as α-linolenic acid (C18:3Δ9,12,15) and linoleic acid (C18:2Δ9,12), which cannot be synthesized by the human body due to the absence of the necessary enzymes (Sipeniece, Miˇsina, Qian, et al., 2021; Yu et al., 2016). Previous studies determined that palmitic acid (C16:0), stearic acid (C18:0), oleic acid (C18:1), linoleic acid (C18:2), and linolenic acid (C18:3) are common in plant oils (Sahu et al., 2020; Sipeniece, Miˇsina, Qian, et al., 2021). The ratio between omega-6 and omega-3 oils (ω-6/ω-3) also plays an important role in nutritional diet, with recommendations of 4:1 to 5:1 being common (Carbone & Charrouf, 2004). The ω-6/ω-3 of many oils is, however, rather far from such recommended values, as in black poppy oil (90:1) and nigella oil (364:1) (Rokosik et al., 2020). According to our previously unpublished data, many oils (apricot kernel oil, argan oil, pine nut oil, hemp oil, safflower oil, and watermelon seed oil) even had undetectable levels of ω-3 FA. On the contrary, chia seed oil, wheat germ oil, blackcurrant oil, hemp oil, and flax seed oil have quite good ω-6/ω-3 values of 1:4, 6:1, 2:1, 2:1, and 1:3, respectively (Guimara˜es et al., 2013; Qian et al., 2018; Rokosik et al., 2020). In view of the vastly different proportions and composition of FAs in various vegetable oils, it is necessary to introduce a nutritional quality index to evaluate the health value based on the functional properties of FAs (Ulbricht & Southgate, 1991). The atherogenic index (AI) and the thrombogenic index of vegetable oils are based on the level of MUFA (Santos-Silva et al., 2002). The ratio of ω-6/ω-3 can be used to calculate the hypocholesterolemia-to-hypercholesterolemic (HH) ratio (Santos-Silva et al., 2002). Oils with higher HH values can be regarded as good quality from the standpoint of nutrition. In contrast, it is better for oil to have low AI and TI values, because these indices are considered cardiovascular disease risk factors (Guimara˜es et al., 2013; Santos-Silva et al., 2002; Ulbricht & Southgate, 1991). The FA compositions and nutritional quality indices of unconventional seed oils are summarized in Table 28.2. Hemp oil and black raspberry seed oil are very rich in PUFA, at 80.7% and 87.1%, respectively. The highest level of α-linolenic acid, an essential FA, was found in seed oil (35.4%
36.1%) (Li et al., 2016; Raczyk et al., 2016) and black raspberry seed oil (33.7%), followed by hemp seed oil (24.1%), dill seed oil (25.45%), and blackcurrant oil (23.7%) (Qian et al., 2018). The data obtained similar nutritional quality indices in these unconventional oils, with AI ranging from 0.02 to 0.60 and the TI ranging from 0.04 to 0.88. The HH values in these oils were 2.38
48.40. Black raspberry seed oil has very attractive parameters, with a HH value of 48.40, a low AI of 0.02, and a low TI of 0.04

Multiple Biological Activities of Unconventional Seed Oils

TABLE 28.2

a

Fatty acid composition and nutritional quality index of selected unconventional seed oils. Fatty acid

Oils

C16:0

C16:1

Nutritional index

C18:0

C18:1

C18:2

C18:3

48.9

32.9

ND

C20:0

C20:1

Others

AI

TI

HH

0.45

5.69

Argan kernel oil

14.4

ND

3.9

ND

ND

ND

0.18

Black cumin oil

11.8
12.0

0
0.4

2.6
2.9 20.5
24.1 56.6
58.3 0.16
0.4

0.1
7.4

ND

ND

0.14
0.15 0.34
0.36 6.41
7.02

Blackcurrant oil

11.8

0.4

3.6

20.5

35.4

23.7

ND

3.9

ND

0.10

0.23

13.82

Dill seed oil

6.1

ND

1.9

10.2

55.3

25.4

0.6

0.5

ND

0.08

0.22

12.56

Hemp seed oil

1.2

10.5

1.8

2.3

55.7

24.1

1

1.3

ND

0.09

0.23

14.88

Wheat germ oil

18.7

ND

0.5

12.7

57.3

9.4

1.2

ND

ND

0.26

0.53

4.24

Borage seed oil

6.9

ND

2.7

29.4

56.5

0.5

ND

ND

ND

0.12

0.45

6.77

Chia seed oil

6.7

0.1

2.7

6.0

18.4

65.6

0.2

ND

ND

0.08

0.05

13.50

Milk thistle seed oil

5.5
11.4

ND

2.9
4.8 15.5
22.4 57.0
60.3 ND

2.5
2.9

0.7
0.9

,1

0.10
0.14 0.23
0.39 13.18
15.04

Poppy seed oil

8.7
8.9

ND

1.8
1.9 13.6
19.0 69.6
74.7 0.5
0.8

ND

ND

ND

0.12
0.09 0.23
0.23 10.11
10.86

Camelina seed oil c

5.9
6.2

0.10
0.11 2.5
2.9 14.6
16.6 18.4
18.7 35.4
36.1 1.16
1.53 13.6
14.5

,1

0.11
0.07 0.14
0.15 11.57
12.06

Grape seed oil

28.19
28.66 0.4
0.8

3.8
3.8 20.7
20.8 40.8
41.0 5.5
5.7

ND

ND

ND

0.42
0.60 0.88

2.38
2.39

Walnut seed oil

6.33
6.51

ND

2.8
3.0 16.6
19.3 62.7
64.3 8.2
8.7

ND

0.2
0.2

ND

0.09
0.07 0.19

13.81
14.56

Blackberry seed oil

3.3

ND

1.6

14.4

63.4

16.5

ND

ND

ND

0.04

0.09

28.58

Black raspberry seed oil

2

ND

0.6

9.7

53.4

33.7

ND

ND

ND

0.02

0.04

48.40

Blueberry seed oil

5.2

ND

1.3

22.2

41.9

28.1

ND

ND

ND

0.07

0.11

17.73

H. suaveolens

6.7

ND

1.3

6.2

85.2

ND

ND

ND

, 0.5

0.08

0.18

13.64

L. nepetifolia

10.1

0.8

2.6

58.3

15.1

0.9

0.1

0.7

ND

0.60

0.33

7.36

O. sanctum

8.1

ND

2.8

14.3

26

48.6

ND

ND

# 0.1

0.11

0.16

10.98

The data in Table 28.2 were summarized from relevant study (Gao et al., 2019; Gu¨naErgo¨nu¨l & AksoyluO¨zbek, 2018; Meddeb et al., 2017; Qian et al., 2018; Raczyk et al., 2016; Rokosik et al., 2020; Sabudak, 2007; Yilmaz et al., 2019).

a

354

28. Factors affecting the quality of produced unconventional seed oils

(Li et al., 2016). The FA of black raspberry consisted mainly of C18:2 and C18:3, and its ω-6/ω-3 ratio was 1.6:1 (Li et al., 2016). Apricot kernel oil also had a higher HH value of 21.49, and lower AI (0.05) and TI (0.11) (Qian et al., 2018). This suggests that such unconventional cold-pressed oils may play a positive role in preventing CHD. It was also possible to use as a functional food to reduce atherosclerosis, thrombosis, and coronary heart ¨ zdemir, 2012). disease (Qian et al., 2018; Uluata & O FA testing shows that not all unconventional seed oils are suitable for consumption. The total MUFA content of radish seed oil is as high as 62.28%, but the level of erucic acid (C22:1), which has cardiotoxic properties, is 40.83% of the total FA (Szulczewska-Remi et al., 2019). Similarly, though mustard oil is widely consumed in Bangladesh due to its unique flavor, it contains 11.38% erucic acid and is not as healthy often thought (Islam et al., 2020; Konuskan et al., 2019).

28.7 Bioactive compounds 28.7.1 Tocochromanols Tocochromanols, including tocopherol and tocotrienol, are efficient natural antioxidants that widely exist in various of plant oils, and in the diet can improve immunity and reproductive functions (Mohammad et al., 2019). Eight isomers of tocochromanols are commonly detected in unconventional oils: α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, α-tocotrienol, β-tocotrienol, and γ-tocotrienol (Qian et al., 2018). Tocotrienol is associated with physiological maintenance, and γ-tocopherol can decrease the risk of cancer. γ-Tocopherol has the greatest antioxidant properties, followed by γ-, β-, and α-tocopherol (Birringer & Lorkowski, 2019). Wheat germ oil is rich in tocochromanols (1551 μg/g); the most abundant tocochromanols were, in order, α-tocopherols (835 μg/g), β-tocopherols (609 μg/g), γ-tocotrienol (637 μg/g), β-tocotrienol (180 μg/g), and α-tocotrienol (5 μg/g). The total tocochromanol content of blackcurrant seed oil was also high, at as much as 1129 μg/g. γ-Tocopherol was detected at levels as high as 797 μg/g, followed by α-tocopherols (222 μg/g), δ-tocopherol (93 μg/g), and α-,β-,γ- tocotrienol, all less than 10 μg/g (Qian et al., 2018). Five isomers of tocochromanol were detected in winter melon seed oil, with β-tocopherol in the highest concentration (478.98
593.3 μg/g oil), followed by γ-tocopherol (236.41
239.2 μg/g oil), α-tocopherol (19.3
30.87 μg/g oil), δ-tocopherol (44.2
196.96 μg/g oil), and γ-tocotrienol (65.80
84.38 μg/g oil). The total tocochromanol content of winter melon was 961.80
1027.60 μg/g (Mohammad et al., 2019). The concentration of tocopherols in Japanese quince seed oils ranged from 1053.7 to 1242.7 μg/g oil (Sipeniece, Miˇsina, Grygier, et al., 2021). Oil from sacha inchi (Plukenetia volubilis) was rich in tocopherols (2450.1 μg/g oil), mainly γ-tocopherol (64.7%) and δ-tocopherol (35.3%) (Rodrı´guez et al., 2021). These unconventional oils may be good sources of tocochromanols. Several other unconventional seed oils were poor in tocochromanols, such as macadamia seed oil (14 μg/g), black cumin oil (250 μg/g), and pine nut oil (185 μg/g) (Qian et al., 2018).

Multiple Biological Activities of Unconventional Seed Oils

28.7 Bioactive compounds

355

28.7.2 Phytosterols Plant sterols or phytosterols are important components of plant membranes that are also common in seeds. Most of the unsaponifiable matter in vegetable oils is phytosterols, and these have a strong antioxidant ability and impact on human health (Piironen et al., 2000). It is widely known that phytosterols can lower serum cholesterol and LDL and prevent heart disease. Phytosterols are harmless to the body and can effectively inhibit absorption of cholesterol from the diet, as well as that of biliary cholesterol (Piironen et al., 2000). Phytosterols such as campesterol, β-sitosterol, and stigmasterol are most common vegetable oils (Go´rna´s et al., 2016). Unconventional seed oils like wheat germ and blackcurrant seed oils are rich in phytosterols, at 858 and 254 mg/100 g oil, respectively. β-Sitosterol was the main sterols constituting 64% of wheat germ oil and 67% of blackcurrant seed oil. Campesterol (225.3 mg/100 g), stigmasterol (17.5 mg/100 g), avenasterol (31.6 mg/100 g), and cycloartenol (8.5 mg/100 g) were also detected in wheat germ oil. The most abundant sterol in blackcurrant oil was campesterol (21.7 mg/100 g), followed by cycloartenol (16.3 mg/100 g), avenasterol (6.6 mg/100 g), and 24-methylene cycloartenol (2.7 mg/100 g), stigmasterol (1.6 mg/100 g), respectively (Qian et al., 2018). Sea buckthorn oil was also rich in phytosterol, which can be considered a functional food that reduces LDL and cholesterol levels. The total level of sterols ranges from 6.2 to 13.4 mg/100 mL in various cultivars, and β-sitosterol (26.64 2 42.57%) was the main sterol in sea buckthorn oils, followed by 24-methylenecycloartanol (1.5
4.0 mg/ 100 mL) (Teleszko et al., 2015). The following oils also contained high levels of phytosterol: O. sanctum seed oils (576.3 mg/100 g), C. uniflora (351.2 mg/100 g), C. alata (289.3 mg/100 g), and I. tinctoria (444.8 mg/100 g) in the Fabaceae family (Go´rna´s et al., 2018; Sahu et al., 2020) and in walnut (174
205 mg/100 g) (Gao et al., 2019; Qian et al., 2018). Other unconventional seed oils, such as black cumin seed oil (44 mg/100 g), dill seed oil (62 mg/100 g), and apricot kernel oil (67 mg/100 g), contain small amounts of sterols (Qian et al., 2018).

28.7.3 Other bioactive compounds 28.7.3.1 Carotenoids and chlorophyll These are natural pigments in plants, which play an important role in antioxidant and photosynthesis. Studies have shown that the consumption of large amounts of carotenoids can reduce the incidence of cardiovascular diseases and certain cancers. As the predominant color pigments in plant oils, carotenoids and chlorophyll may cause oil darkening during oxidation (Mohammad et al., 2019). The carotenoids in apricot kernel oils of various cultivars range from 0.15 to 0.53 mg/100 g (Go´rna´s et al., 2017), in Fabaceae family seed oils from 0.3 to 43.1 mg/100 g (Go´rna´s et al., 2018), and in legumes seed oils from 0.2 to 9.2 mg/100 g (Sipeniece, Miˇsina, Qian, et al., 2021). Camelina was found to contain β-carotene at 7.8
11.2 mg/100 g oil (Raczyk et al., 2016), while the level of carotenoids in pumpkin seed oil was 6.95
7.60 mg/100 g (Akin et al., 2018).

Multiple Biological Activities of Unconventional Seed Oils

356

28. Factors affecting the quality of produced unconventional seed oils

28.7.3.2 Squalene (2,6,10,15,19,23-hexamethyl-2,3,10,14,18,22-tetracosahexene) is a triterpenic hydrocarbon with a positive effect on the immune system; it exists in olive oils and also in shark livers (Carbone & Charrouf, 2004). Sea buckthorn berries are rich in squalene, whose concentration ranges from 885.71 mg to 2714.37 mg/100 mL (Teleszko et al., 2015). Interestingly, squalene is found in some unconventional seed oils: its abundance in Japanese quince seed oils was 1035.9
1497.3 mg/100 g (Sipeniece, Miˇsina, Grygier, et al., 2021), in O. sanctum seed oil 45.8 mg/100 g (Sahu et al., 2020), in Fabaceae family seed oils 0.9
56.0 mg/ ´ 100 g (Go´rna´s et al., 2018), and in apricot oils 12.6
43.9 mg/100 g (Rudzinska et al., 2017). Pumpkin seed oil has been found to have 591.3
632.5 mg/100 g squalene (Akin et al., 2018), while walnut has 0.33
0.60 mg/100 g (Gao et al., 2019). 28.7.3.3 Phenolic compounds They are natural antioxidants found in seeds (Corbu et al., 2020). There are various classes of phenolic compounds, such as phenolic acid, phenolic alcohols, flavonoids, secoiridoids, and lignans (Carbone & Charrouf, 2004). The phenolic compositions of some unconventional oils are very attractive. Eight phenolic substances were detected in winter melon seed oil: calculated as equivalents of gallic acid (GAE μg/g oil), the total phenolic concentration was 12.27
17.24 μg/g, which included gallic acid (0.65 μg/g), 3,4-dihydroxybenzoic acid (0.56 μg/g), 3,4-dihydroxybenzaldehydev (0.44
0.45 μg/g), vanillic acid (0.68
0.87 μg/g), vanillin acid (4.78
8.86 μg/g), p-coumaric acid (1.92
2.02 μg/g), transcinnamic acid (1.35
1.58 μg/g), and ferulic acid (1.88
2.26 μg/g), respectively (Mohammad et al., 2019). In marula oils, the total phenolic content was 1.7
35.7 GAE μg/g, and the total flavonoids content was 122
126 rutin equivalents μg/g oil (Mariod et al., 2011). Total polyphenols detected in pumpkin seed oil were 3.96
5.82 mg GAE/100 g (Akin et al., 2018), in grape seed oil 6.43
9.81 (mg GAE/100 g) (Yilmaz et al., 2019), in milk thistle seed oil 3.59
8.12 mg/100 g (Meddeb et al., 2017), and in walnut oil 2.83
4.48 mg/100 g (Gao et al., 2019).

28.8 Frying Frying, the most common use for plant oils, is a traditional cooking process using a high temperature, typically around 150 C
200 C and involves a series of physical and chemical changes (Akoh, 2017). The quality of food is associated with frying time and temperature and also relates to the type of food and oil (Park & Kim, 2016). Chemical compositions, such as FA and endogenous minor components, are the most significant factors ´ affecting oil degradation during frying (Rudzinska et al., 2018). Air and moisture in oils can cause problems of thermal and oxidative decomposition, leading to the formation of polymers, which are unhealthy (Park & Kim, 2016). In the frying process, it has been shown that the decrease in USFA and the increase in SFA are accompanied by an increase in AV and PV, indicating that the FA is undergoing ´ hydrolyzation and the initial reactions of oxidation (Rudzinska et al., 2018). PV and AV

Multiple Biological Activities of Unconventional Seed Oils

28.9 Conclusions

357

are both very significant indicators of oil quality. During frying, hydroperoxide breaks down and secondary oxidation occurs at high temperatures, so the increase in PV was only related to the frying time, and not to the type of oil (Park & Kim, 2016). It has been reported that the PV and AV of palm oil increased significantly after frying chickens. The PV of palm oil increased from 7.08 to 15.48 mEq O2/kg after frying, which was much better than the increase from 1.46 to 66.03 mEq O2/kg seen for soybean oil and the increase from 9.39 to 62.92 mEq O2/kg seen for canola oil. AV is only increased by frying times without related to the type of oil (Park & Kim, 2016). Frying always deteriorates the quality of vegetable oils, and total oxidation can be used as an objective indicator of oil ´ quality during frying (Rodrı´guez et al., 2021; Rudzinska et al., 2018). The AV and PV of the fresh cold-pressed oils mentioned above exceeded the recommended values, and the frying process would thus produce more FFA and peroxide, negatively affecting the quality of the oil. Tocochromanols have a positive effect on the stability of the frying process. The tocochromanols content had decreased by frying time. The total polar compounds can be used to assess the level of oil degradation and tends to increase exponentially during frying. Palm oil produced smaller amounts of polar compounds than soybean oil and sunflower ´ oil (Rudzinska et al., 2018). As the main oil crop in Bangladesh, mustard oil is widely consumed for its flavor and is also used for frying in many counties. However, the quality of mustard oil decreases after frying. When mustard oil is heated to 180 C for 3
10-minute rounds of frying, its IV decreased; this indicates that the level of unsaturation decreases, which can have a negative effect on the maintenance of high-density lipoprotein in the blood. Hydrolysis, oxidation, polymerization, and other reactions in the repeated frying process reduce the quality of mustard oil, causing damage to the liver, kidneys, and intestines and producing carcinogenic by-products (Islam et al., 2020). Fresh mustard seed oil contained 11% erucic acid, and the quality after frying was further reduced. It is thus not recommended to ingest mustard oil, and especially not to use it for deep-frying (Islam et al., 2020; Konuskan et al., 2019). Unlike mustard oil, the oil of sacha inchi (Plukenetia volubilis) is very good for brief frying of potato fries, due to its high PUFA and tocopherol contents, which promote oil stability. Tocopherols are natural antioxidants that protect PUFAs from degradation, making oils more stable (Rodrı´guez et al., 2021).

28.9 Conclusions The factors relating to agriculture, oil processing and storage, physiochemical indices, bioactive compounds, and the frying process all affect the quality of unconventional seed oils and were summarized in this chapter. Agricultural factors, such as plant species and genotype, ambient temperature, and harvest time greatly affect seed quality and oil yield and further influence the bioactive substances in oils. Oil processing involves seed storage and handling, oil pressing, extraction, and refining. The use of appropriate methods can not only enhance oil yield but also improve oil antioxidant capacity, while reducing the loss of active substances and increasing nutrient quality.

Multiple Biological Activities of Unconventional Seed Oils

358

28. Factors affecting the quality of produced unconventional seed oils

During the storage of seed oils, temperature, light, packaging materials, and storage time can lead to undesirable changes in the oil, such as oxidation and the reduction of bioactive substances. The oxidation of seed oil can be effectively inhibited by adding antioxidants or flushing with nitrogen. Many physical and chemical parameters serve as good indicators of seed oil quality. FA composition is a significant factor affecting the quality of oils. Many unconventional seed oils are good sources of FAs, for example, hemp oil has a high level of PUFA, apricot kernel oils have good nutritional quality indices, and blackcurrant oil has a good ω-6/ω-3 ratio. Unconventional seed oils can be considered as functional foods due to their rich bioactive compounds. Attractively, wheat germ oil and blackcurrant oils contain high level of both phytosterols and tocochromanols. Squalene has been detected in some unconventional oils, such as Japanese quince seed oil, O. sanctum seed oil, Fabaceae family seed oil, and apricot oil. Frying involves a large number of very complex chemical and physical changes, and many vegetable oils are not suitable for frying, though sacha inchi has excellent frying properties.

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C H A P T E R

29 Chemical and compositional structures (fatty acids, sterols, and tocopherols) of unconventional seed oils and their biological activities Saeid Hazrati1, Saeed Mollaei2 and Farhad Habibzadeh3 1

Department of Agronomy, Faculty of Agriculture, Azarbaijan Shahid Madani University, Tabriz, Iran 2Department of Chemistry, Faculty of Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran 3Department of Genetics and Plant Breeding, Faculty of Agriculture and Natural Resources, Imam Khomeini International University, Qazvin, Iran

29.1 Introduction Oil as the main part of diets, provides the highest calorie compared to carbohydrates and protein. They have a main role in the diet as salad oil, cooking, food product formulation and also concerning the economy. In the world, many unfamiliar or underexplored plant seeds exit which have high amount of oil economically good for industrial purposes or consumable. These oils are known as unconventional oil (Sabikhi & Sathish Kumar, 2012). Generally, the demand and supply of oils are dependent on oils like soybean, cotton, coconut, olive, palm, and groundnut. However, due to different factors such as climatic conditions, inflation, and population, the need for new source of oils such as unconventional oils have been increased (Choudhary et al.,2014). Unconventional oils are the new boosting area to up thrust the production of edible oils and reduce the dependence of oil import from other countries. The consumer awareness about food and health may directly impact the producers to work in that direction. Because of food habits and daily lifestyle, some diseases such as periodontal disease, cancer, osteoporosis, coronary heart disease, obesity, etc. could generate (Sonodaet al., 2018). The compounds of vegetable oils like tocopherols, sterols, and

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fatty acids (FAs) possess nutraceutical properties (Va´zquez et al., 2019). So, it is important to know the compounds of unconventional oils and their biology activities.

29.2 Pyrus glabra and Pyrus syriaca The pear trees and shrubs belong to the genus Pyrus (family Rosaceae) that are tolerable at different temperatures and in favorable conditions. The wild pears Hermo (Pyrus syriaca) and anchochek (P. glabra) as perennial plants are from the Rosaceae family (Jalilian et al., 2018). They are found in the southwest of Iran (Sepidan region) and are 6 m in height and have smooth and gray leaves with prickly branches (Zamani et al., 2009). They are characterized by oblong and lanceolate leaves, small and white flowers and the green fruit that following ripening are brownish to black. The spherical fruits are 2.5 cm consisting of nearly six large seeds (thousand seed weight is 120 g) (Hazrati-Yadekori et al., 2012; Sharifani et al., 2017). From August to September the fruits ripe and following the fruit collection, the seeds (black) are isolated (Hashemi et al., 2018). The seeds oils have long been applied for body empowerment and also as a diuretic (Hashemi et al., 2018; HazratiYadekori et al., 2012). The fruits of pear, similar to different members of the Rosaceae family have few seeds (about ten tiny seeds per fruit) that could furnish 15%
31% oleaginous attributes. The Anchochek seed oil content collected from Sepidan area, Fars, Iran, was 22%
33% (Hashemi et al., 2018; Hazrati et al., 2020; Hazrati-Yadekori et al., 2012). In various species of pear seed oil unsaturated fatty acids (UFAs), tocochromanols, and phytosterols are the most attractive oleaginous compounds. Oil of Anchochek is rich in monoand polyunsaturated FAs. Anchochek and Hermo seed oils have FAs such as oleic, linoleic, palmitoleic, palmitic, α-linolenic, stearic, arachidic, gondoic acids, and Heneicosanoic acid methyl ester (Hashemi et al., 2018; Hazrati et al., 2020; Hazrati-Yadekori et al., 2012). The major FAs in the P. syriaca are linoleic acid (C18:02; 46.99%) and oleic acid (C18:01; 41.43%), whereas in the P. glabra these values are 49.51% and 37.47%, respectively. Moreover, palmitic acid composes a significant percentage of P. syriaca and P. glabra seeds oil by 7.89% and 8.7%, respectively. Stearic, palmitoleic, alpha-linolenic, linoleic, arachidic, methyl ester henicosanoeic acids are other FAs in P. glabra oil whereas P. syriaca oil includes palmitoleic, alpha-linoleic, palmitic, stearic, arachidic, and gondoic acids (Hashemi et al., 2018; Hazrati et al., 2020). The total UFAs content available in P. syriaca and P. glabra oils is 89.33% and 87.68%, respectively, while and the amounts of Stearic and palmitic acid (SFA) were 10.66% and 12.58%, respectively. Based on the acquired consequences, the monounsaturated fatty acids (MUFAs) have been more than polyunsaturated fatty acids (PUFAs) in both species. The results of the quantity of linoleic acid FA (omega 6) indicated that P. syriaca seed oil (46.99 6 0.07%) had more omega 6 than P. glabra (37.47). The ratio of MUFAs to PUFAs as an index for the tendency of auto-oxidation was measured to be 1.31 and 0.89 in the seeds of P. syriaca and P. glabra, respectively. This value was 2.89 for Pistacia khinjuk fruits (Asnaashari et al., 2015), and 0.89 for P. glabra (Hashemi et al., 2018). The amount of SFAs, MUFAs, PUFAs, and ΣMUFAs/ ΣPUFAs for Anchochek is 12.588, 49.743, 37.94, 1.31 and for Hermo 10.663, 42.177, 47.16, 0.89, respectively (Hazrati et al., 2020; Mushtaq et al., 2019). Different identified FAs in the pear species seeds are palmitic, palmitoleic,

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alpha-linolenic, and stearic acids (Mushtaq et al., 2019). Hashemi et al. (2018) showed that the yield of P. glabra oil was 22.40% and the main FAs were linoleic and oleic acids.

29.2.1 Tocopherol composition The total content of tocopherols in P. syriaca (45.50 mg/100 g oil) has been reported smaller compared with P. glabra oil (69.80 mg/100 g oil). The seed oils of P. syriaca and P. glabra have high levels of total tocopherols, which is more than edible oils, such as Helianthus annuus Sesamumindicum, Arachishypogaea, Vitisvinifera, Elaeis guineensis, and Carthamustinctorius based on the Codex Alimentarius Commission (1999,2009). Four tocopherols were reported and quantified in the P. syriaca and, P. glabra. Also, α-tocopherol is the major tocopherol in the P. syriaca and P. glabra oils(40.5 and 60.2 mg/100 g, respectively). According to Hashemi et al. (2018), the total tocopherol level in the P. glabra was highly lower compared with those declared by Go´rna´s et al. (2016) in the seed oils of P. communis. Likewise, the individual amount of tocopherols (α, ß, γ, and δ) was also not consistent, as Go´rna´s et al. (2016b) reported γ-tocopherols as the major tocopherols and Hashemi et al. (2018) announced P. glabra rich in α-tocopherol. They reported that the seed oil of P. glabra is rich α- tocopherols and the amounts of other tocopherols (ß, γ, and δ) were traces. Tocopherols are produced in seeds at different concentrations, and the antioxidative effect is different among individual compounds. Tocopherols are defensive against oxidative stress and seem important for fixed neurological performance (Aggarwal et al., 2010). Antioxidants are effective in strengthening the body’s antioxidant defense system for controlling, preventing, or treatment of diseases and their use has been widely increased because of the side effects of synthetic compounds (Kurutas et al., 2016). Natural antioxidants can be observed in fruits, flowers, leaves, stems, and roots. There is a biological balance between them and other compounds in plants (Memvanga et al., 2015).

29.2.2 Biological activity of seed oils In a research on the antioxidant properties of P. syriaca and P. glabra oils, it was reported that the inhibitory activities of oils are associated with the oil concentration and an increase in the inhibitory percentage. P. syriaca and P. glabra oils were found with the IC50 of 46.3 and 43.4 μg/mL, respectively. P. syriaca oil possesses a smaller antioxidant effect compared with P. glabra oil. The highest reducing capacity was related to the seed oil of P. glabra (39.8 μM), whereas the oil of P. syriaca was 28.7 μM (Hazrati et al., 2020). The higher antioxidant effect of P. glabra in comparison with the P. syriaca oil may be related to greater contents of tocopherols and reducing compounds. Such compounds possibly include phenolic proton dissociation and hydroxyl groups on the aromatic ring results in a phenolate anion, leading to reducing FCR (Box, 1983). Therefore, the reaction happens by the mechanism of electron transfer. Thus, antioxidant compounds significantly affect the reduction of free radicals as well as the suppression of hydroxyl conversion to free radicals, as a main factor to develop cancer in humans. According to Varela (2016), the antioxidant effects of phenolic compounds are because of the reduction of free radicals, like superoxides, fat peroxides, hydroxide radicals, and anions. Nimse and Pal (2015)

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reported that antioxidants can also trap single oxygen. Measuring the reducing capacity declared that the P. glabra possibly includes the highest content of antioxidants, which act as the reduction factor reacting with radical compounds through electron release and converting them into resistant compounds, leading to the removal of the free radical chain (Leopoldini et al., 2004). The antibacterial effect of the P. syriaca and P. glabra oils has been assessed against two Gram-negative and five Gram-positive bacteria. Based on the disk diffusion technique and minimum inhibitory concentration (MIC) results, the seed oils showed inhibitory effects against the evaluated bacteria. These findings indicated that Bacillus cereus (MIC: 7.5 mg/mL) was the most vulnerable bacterium against P. glabra oil.

29.2.3 Sterols Phytosterols or sterols are alike to cholesterols and essential for stabilizing phospholipid bilayer of cell membranes and different structures of cell. Phytosterols absorb cholesterol in the intestinal mucosa and reduce its levels in the blood by 10
15 (Chen et al., 2008). They have long also been applied as cholesterol-lowering agents. According to the Drug and Food Administration of the United States, phytosterols are “part of a dietary strategy for reducing the risk of coronary heart diseases.” Kritchevsky and Chen (2005) reported that the daily intake of phytosterol (3 g) is linked to a consistent and reproducible decrease in lowdensity lipoprotein (LDL) cholesterol levels up to 10% and decreases the risk of coronary heart disease by 20%. The Pyrus seed oil is rich in phytosterols depending on the extraction method and fruit species. Also, the sterol level of the pear seed oil is comparable with some cultivars of its relative “apple seeds.” In general, seven sterols, such as gramisterol, cholesterol, β-sitosterol, campesterol, citrostadienol, Δ7-stigmasterol, and Δ5-avenasterol are available in Pyrus seed oils. β-sitosterol constituted over 80% of total sterols followed by campesterol (13.9
29.7 mg/100 g oil), and Δ5-avenasterol (Mushtaq et al., 2019).

29.3 Chrozophora tinctoria Chrozophora is a member of the family of Euphorbiaceae and has nine species (Marzouk et al., 2015). It is used for the warts and fever (Delazar et al., 2004). Its seeds, leaves, and stems have been applied in industrial and food products. Fruits are the most conspicuous organ of C. tinctoria and are strange-looking capsules with three spherical bodies fused in a rather rounded-triangular structure. Each fruit has three obovate angular seeds that are surrounded by a thin, the latter carunculate apically, embryo flat; endosperm copious. The fruits are 4 mm and gray to light brown (Van Welzen, 1999).The seed contains 5% as moisture, 21.7 crude fiber,14% protein, and 1.15% as ash. C. tinctoria seed is rich in yellow oil (26.40%).

29.3.1 Fatty acid compositions FAs available in the C. tinctoria seeds are palmitoleic, stearic, palmitic, linoleic, oleic, and linolenic acids. The major FAs are the UFAs that consist 91.45% of the total oil, such

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as MUFAs(palmitoleic and oleic acid) and PUFAs (linolenic and linoleic acid). Thus, C. tinctoria oil has a high content of PUFAs, such as linoleic acid as the major FA. The main FAs were linoleic, oleic acid, palmitic, and stearic acids with the percentage of 76.68, 13.99, 5.32, and 3.15, respectively (Hazrati et al., 2019).The amount of Σ UFAs, SFAs, PUFAs, MUFAs, ΣUFAs: ΣSFAs, and ΣMUFAs/ ΣPUFAs for C. tinctoria are 91.45, 8.43, 14.10, 77.35, 10.85, and 0.18. According to these results, this plant is rich in edible oil. SFA compose 8.43% of the total oil. Linoleic, stearic, oleic, and palmitic acids are the major FAs in C. brocchiana oil (Ahmed,2015). Alike results have been reported in other species, like C. orinocense and C. plicata which had linoleic acid in the percentage of 75.13 and 59.3, respectively (Alfaro,1994; EL Bassam,2013). The linoleic content in C. tinctoria oil is remarkably higher in comparison with other oilseeds. MUFAs and PUFAs as indicators for oil autoxidation are 0.18 much less than other oils (Asnaashari et al., 2015; Hashemi et al., 2018).

29.3.2 Tocopherol and sterols composition The main tocopherol in the C. tinctoria seed oils is α, δ- and γ-tocopherols with the levels of 4.20, 70, and 12.30 mg/100 g, respectively. The C. tinctoria oil has a high level of total tocopherols (87.35 mg/100 g). C. tinctoria oil is high in tocopherols, which is higher than other oils such as palm, sunflower, sesame, grape, groundnut, and saffron, as reported by the Codex Alimentarius Commission (1999, 2009). Tocopherols have protective activity against oxidative stress associated with metabolic syndrome and are important for fixed neurological activities (Dias, 2012). Phytochemical assessment of the genus Chrozophora led to the isolation of different types of chemical constituents, such as sterols (Ahmed et al., 2014).

29.3.3 Biological activity of seed oils C. tinctoria oil is a suitable source of antioxidants. Hazrati et al. (2019) measured the antioxidant activity of C. tinctoria by the DPPH and β-Carotene linoleic acid inhibition method and revealed that C. tinctoria had high antioxidant activity. DPPH percentage after 30 minutes was 45%, which can indicate high activity to neutralize free radicals. The β-carotene/linoleate model assesses the effectiveness of antioxidative constituents to inhibit linoleic acid-induced oxidation of β-carotene. C. tinctoria oil could retard the β-carotene oxidation in the emulsion method. The inhibition rate of β-carotene degradation defined by the rate of discoloration of C. tinctoria oil extract was reported to be 42%. Phenolic compounds are used to make the taste and extend the oil shelf life (Jorge et al., 2015). The phenolic content of our research was higher compared with that of several other oilseeds. Kozlowska et al. (2016) reported the phenolic content of caraway, coriander, white mustard, nutmeg, and anise as follows: 0.78, 0.20, 1.50, 3.21, and 2.52 mg/g oil, respectively. Also, higher phenolic content is protected against oxidation (Kozlowska et al., 2016). Flavonoids are compounds with antioxidant properties. Pigments are important compounds in auto-oxidation as well as photo-oxidation processes (Mı´nguez-Mosquera et al., 1991).

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They act as antioxidants in dark locations (Psomiadou & Tsimidou,2002) and possess biological and medicinal activities (Ranalli et al., 2000). Also, the oil of C. tinctoria is yellow because of the high carotenes, apocarotenals, and annatos content that are applied in oil industries (Oomah et al., 2000). In a report, the antiinflammatory property of phenolic compounds collected from C. tinctoria was examined through the measurement of the concentrations of IL-6, IL-1b, TNF-a, and PGE2 in the supernatant media of human peripheral blood mononuclear cells stimulated by phytohaemagglutinin. At the level of 100 mM, these compounds caused a significant decrease in Il-1b, Il-6, and PGE2 to closely standard values (Abdallah et al., 2015).

29.4 Pistacia spp The genus of Pistacia (Anacardiaceae family) contains about 15 species of which three, including P. atlantica, P. vera, and P. khinjuk grow naturally in Iran (Mozaffarian, 2005). P. atlantica and P. khinjuk, also known in Persian as “Baneh” and “Kolkhoun,” respectively, are extensively dispersed in the Zagrossian region of Iran (Bozorgi et al., 2013; Ezatpour et al., 2015). Different organs of these plants, including the fruit, leaf, resin, bark and aerial parts, have been largely used as folk medicines for the treatment of different situations such as cutaneous, respiratory, gastrointestinal, infectious, and renal diseases (Ezatpour et al., 2015; SoleimanBeigi & Arzehgar, 2013). Their fruits and oil are eaten as nuts and are used in the treatment of heart, stomach, and respiratory system disorders, for wound healing and gastrointestinal disorders (Hatamnia, Rostamzad, Hosseini et al., 2016 and Hatamnia, Rostamzad, Malekzadeh et al., 2016). The predominant reasons for increased attention to Pistacia nuts are their high oil content and their healthy FA composition. According to the results, the two species of Pistacia investigated can be considered as a good source of vegetable oils. Although the amount of oil is lower when compared to yields from P. vera, it generally contains 50%
62% of oil (Satil et al., 2003; Ojeda-Amador et al., 2018). The same results were obtained by other researchers on, P. atlantica, P. khinjuk, and P. vera (Mortazavi et al., 2015; Dini et al., 2016; Labdelli et al., 2019; Mohammadi et al., 2019). The high amount of oil in the kernels of these plants, especially when compared with the other oil seed crops, means that they can be considered as a possible commercial source of plant oil. These species of Pistacio grow 5
15 m tall. The leaves are alternate and pinnate and could be evergreen or deciduous. These important species of Pistacia are known as the origin of Pistachio. The P. khinjuk and P. atlantica fruits utilized as edible wild nuts. From ancient times, the fruits of these plants have been used as snacks and in cooking (Ghasemi ˘ et al., 2015). Pirbalouti and Aghaee, 2011; Bozorgi et al., 2013; Hacıbekiroglu Vegetable oils are normally extracted from plant fruits and have high nutritional value. In addition to widespread uses in human diet and also in industry, the oils have many applications in the pharmaceutical industry because of the numerous therapeutic effects of their natural ingredients. Lack of essential FAs in the human diet can be responsible for the development of disorders such as cardiovascular disease, viral infections, certain types of cancers, eczema, diabetes mellitus, rheumatoid arthritis, and autoimmune diseases (Moazzami et al., 2015). In the study they gave higher oil yield for Pistacia khinjuk (31.00%) when compared to Pistacia atlantica (24.33%).

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29.4.1 Fatty acid composition Numerous studies have stated the FA composition of pistachio oils. Results indicated that kernels of Pistacia species are identifiable by the incidences of Palmitic, Oleic, Stearic, Linoleic, and Palmitoleic acids. Gas chromatography analysis indicated that oils of both the species investigated contained high amounts of MUFAs followed by SFAs, while PUFAs were present in lower contents. As can be seen from the following results, UFAs comprised around 80% of the FAs in both of the assayed oils. The most dominant FAs in P. khinjuk and P. atlantica are oleic acid (51.49% and 53.15%), Linoleic acid (16.43% and 20.41%), and palmitic acid (23.32% and 20.20%), respectively. SFA contents of P. khinjuk and P. atlantica were 25.22% and 22.59%, respectively. The results of researches showed that P. atlantica and P. khinjuk are rich in this type of FA with amounts of 21.12% and 17.32%, respectively. USFA/SFA ratio is as a normative of the tendency of oils to selfoxidative reactions. These amounts in P. atlantica and P. khinjuk were 3.43 and 2.97, respectively. Several investigates have described that the FA composition of Pistacia oils shows a high Oleic acid content, from 51% to 81% (Arena et al., 2007; Esteki et al., 2019; SenaMoreno et al., 2015) which is higher than several other seed oils (FAO-WHO Codex Stan 210-1999). An investigation into the FA composition of three Pistacia species revealed that the main FA components found in P. khinjuk, P. vera, and P. Atlantica oils were Oleic acid (Tavakoli and Pazhouhanmehr, 2010). Among nuts, Pistacia (Pistacia spp.) had interesting nutritional value due to the existence of cardioprotective compounds such as phenolics, tocopherols, oleic acid, and phytosterols which lead to a high potential antiinflammatory and antioxidant food product (Tavakoli and Pazhouhanmehr, 2010). Oleic acid is a main FA that plays a key and effective role in the maintenance of the human body. Its high oxidative stability is due to low PUFAs contents. The important role of this essential FA in the human body means that natural materials containing this FA may be of strategic importance. Essential FAs are only absorbed by the human body from food stuffs; the human body is not capable of synthesizing them. One of the most important FAs for lowering blood cholesterol is α-linolenic acid (ω-3 FA). Today, foods containing ω-3 are recommended for health, especially for the inhibition of cardiovascular disease. Due to the existence of α-linolenic acid, P. atlantica and P. khinjuk can also be identified as a ω-3 plant source. The FA composition of Pistacia oil is vital for edible source seed oils. FAs that contain several unsaturated bunches play a vital and effective role in lowering blood plasma cholesterol levels (Mattson and Grundy, 1985). Pistacia is rich in UFAs. The high UFA/SFA ratio found in P. atlantica (3.43) and P. khinjuk (2.97) shows them to be a worthwhile source of UFAs. Regarding the well-documented harmful effects of SFA and food values of PUFAs, the optimum oil here, in terms of food value, was P. atlantica.

29.4.2 Biological activity of seed oils Pistacia are a good bioactive compounds, due to their high important UFAs content, as well as phenolic compounds (Ghasemynasabparizi et al., 2015; Martinez et al., 2016). Plant oil antioxidants play a key role in protecting health. Among seed oils, Pistacia spp. exhibits

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interesting dietary properties because they have cardio-protective constituents, such as high phytosterols, phenolics, oleic acid, tannins, flavonoids, and tocopherols (Amarowicz ¨ zcan, 2006; Ramadan, 2019). et al., 2004; Mattha¨us & O 29.4.2.1 DPPH radical scavenging assay In study the DPPH radical scavenging assay, there were significant differences between the two species of Pistacia. The concentration of P. atlantica and P. khinjuk extracts resulted in 50% of radical inhibition. The range of antioxidant potential revealed in the research showed P. khinjuk extract with 15.733 6 0.689 mg/g as having higher inhibitory power than P. atlantica extract, with a value of 4.545 6 0.655 mg/g. Antioxidants available in the solution can inhibit the destruction of β-carotene reaction with the linoleate free radical. The inhibition ratios of the oxidation of linoleic acid by P. khinjuk and P. atlantica were 62 6 1.20% and 38 6 0.57% respectively. Both species P. atlantica (2.79) and P. khinjuk (2.40) can be considered as sources of stable oils. A similar result has been reported in P. khinjuk (Tavakoli et al., 2016). The relationship between the PUFAs/SFAs ratio and the oxidizability value from oils and their oxidative stability are the opposite (Tavakoli et al., 2016). According to the obtained findings, it can be expected that P. atlantica oil shows proper oxidative stability compared with P. khinjuk. A positive correlation is observed between phenols and antioxidant activity in different oils (Hatamnia et al., 2014; Hatamnia, Rostamzad, Malekzadeh et al., 2016). High amounts of PUFAs lead to lesser oxidative durability and shorter shelf life of oils (Bodoira et al., 2017). The high levels of phenolic compounds are a major cause of the antioxidant activity of seed oils. Phenolic compounds as natural antioxidants are main factors for estimating the quality of edible seed oils. According to this study, P. atlantica and P. khinjuk fruits are good sources of phenolic compounds well known for their antioxidant activities. P. atlantica seed oil, with high antioxidant activity than the P. khinjuk kernel oil, possibly has a high level of phenolic content. DPPH scavenging activity was improved by the total phenolic content. Found results are in line with study done by Won et al. (2013) and Dong et al. (2015), who declared a positive correlation between antioxidant effect and phenol contents. The β-carotene-linoleic acid assay is based on the changes in the color of β-carotene against linoleic acid free radical. The antioxidant activity of P. khinjuk is higher than that of P. atlantica. In the β-carotene/linoleic acid system, consequences were consistent by the data achieved from the DPPH assay.

29.4.3 Sterol composition In a study, β-sitosterol, campesterol, Δ5-avenasterol, cholesterol, and stigmasterol sterols were recognized for the P. khinjuk and P. atlantica oils. The total sterol amount of the oil extracted from P. atlantica and P. khinjuk samples was 1125
2784 mg/kg oil. β-sitosterol, followed by campesterol, -avenasterol, stigmasterol, brassicasterol, and cholesterol were the more important sterols in the oils (Bozorgi et al., 2013; Yahyavi et al., 2020). In another investigation on the sterol composition of seed oil of P. atlantica (mg/100 g of

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oil), beta-sitosterol (as the main sterol, 189.9 mg/100 g oil) was amounting for about 87% of the total content of sterols. Campesterol (9.4 mg/100 g oil) and avenasterol (4.9 mg/ 100 g oil) comprised about 4% and 2% of the total sterols, respectively. Cholesterol (0.9 mg/100 g oil) as a minor sterol, included 0.4% of the total content of sterols (SaberTehrani et al., 2013). Phytosterol can lessening serum LDL levels and protect against cardiovascular diseases; therefore, it can be used for improving functional foods. Betasitosterol is the most abundant sterol in nuts with the total sterol contents ranging from 99.12 to 207.17 mg/100 g oil (Lagarda et al., 2006). P. atlantica is rich in beta-sitosterol (189.9 mg/100 g oil).

29.4.4 Tocopherols P. atlantica and P. khinjuk fruit oils appear to have high rates of tocopherols. Tocopherols are naturally occurring constituents that are available in different amounts in vegetable oils. Among the tocopherols recognized in Pistacia seeds, α, β, and γ forms and tocotrienol are well known, the predominant tocopherols fruit oils were α- and γ-tocopherol, depending on the species, the location, the method, and the stage of growth (Chelghoum et al., 2020; Gong et al., 2017; Guenane et al., 2015; Martinez et al., 2016). Saber-Tehrani et al. (2013) evaluated the tocopherol content of Iranian P. atlantica cold-pressed oil by a C-18 Lichrospher RP-100 a polar column and declared a high amount of tocopherols in P. atlantica cold press oil (409.97 mg/kg oil). α-tocopherol had the highest concentration (379.68 mg/kg). α-tocopherol as an antioxidant reduces the risk of cancer and cardiovascular diseases. The (γ 1 β)-tocopherol and δ-tocopherol content was 20.70 and 9.59 mg/kg oil, respectively. P. atlantica fruit oils were γ-and α-tocopherol with values ranging from 10.1 to 34.8 mg/100 g and from 7.5 to 32.6 mg/100 g, respectively. γ-Tocopherol as a functional compound displays a bioavailability similar to α-tocopherol (Jiang et al., 2001), and acts in vivo and in vitro. It is an effective antioxidant in food lipid matrices (Wagner et al., 2004).

29.5 Nigella sativa N. sativa L. (black cumin) belong to Ranunculaceae family. This plant is one of herbal plants that extensively distributed around the world. This plant is generally applied as a spice in food industries and modern pharmaceutical. The seeds of this plant is mainly produced the oils, which are utilized for various purposes such as production of oil. The composition of Nigella seed oils cultivated from different ecological origin has been extensively researched. Al-Jassir (1992) described that oleic and linoleic acids were the main unsaturated FAs in the seeds of N. sativa growing in Saudi Arabia, while palmitic acid was the major saturated one. Nickavar et al. (2003) extracted N. sativa seed oils using different solvents and studied their FA profiles. As a result of his study, eight FAs, which represented almost 99.5% of the total FA composition, were recognized in the oil. The FAs of oil contained four unsaturated and four saturated FAs, which represented 82.5% and 17.0% of the FAs, respectively. The main constituents of N. sativa seed oil were linoleic acid, oleic acid, and palmitic acid with percentage of 55.6, 23.4, and 12.5, respectively.

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According to the research done by Dinagaran et al. (2016), the main compounds of black cumin seed oils were 9-eicosyne (63.0%), linoleic acid (13.5%), and palmitic acid (9.7%). Also, 63.04% of the N. sativa seed oil extract were saturated aliphatic FA. In Parhizkar et al.’s study (2011), the FA compositions of different extracts of N. sativa were investigated. According to their results, linoleic acid was the main FA present in the methanol, hexane, SFE extracts of N. sativa, which contain 56.82%, 53.14%, and 52.66% of total FAs, respectively. Oleic acid was the other main FA, which gave 24.40%, 23.04%, and 22.74% of total FA in the oil extracts of methanol, hexane, and SFE, respectively. The total percentage of saturated FA in the oil extracts of SFE, hexane, and methanol were 21.31, 20.05, and 15.38, respectively, while the total percentage of unsaturated FAs in the three different extracts were 78.68, 79.94, and 84.62, respectively. Kaskoos (2011) obtained oil from N. sativa seed which had 28.2% yield. He could identify 26 FAs in the oil, which was 95% of total FA composition. They consisted of eight saturated FAs and eighteen unsaturated FAs with percentage of 15.1 and 79.9, respectively. Docosahexaenoic acid DHA (2.97%), eicosapentaenoic acid EPA (5.98%), eicosatrienoic acid (4.71%), palmitic acid (8.51%), oleic acid (16.59%), and linoleic acid (42.76%) were the main components of N. sativa seed oil. Tulukcu (2011) collected N. sativa seed oils from eight different regions and reported their FA profiles. As a result of his study, the main FAs were linoleic acid (54%
70%), oleic acid (15%
24%), and palmitic acid (8.2%
13.3%). In another study, 13 FA compounds which comprise 96% to 99% of total oil were identified from different areas. The results showed that three valuable unsaturated Fas, that is, oleic, linoleic, and palmitic acid were the main FAs of seed oil. The percentage of linoleic acid changed from a range of 51.84%
55.67% in the first year and 51.67%
54.59% in the second year (Hosseini et al., 2019). So, these studies confirmed that N. sativa seed oil could be applied as a rich source of linoleic acid. Also, the changes among the percentages of FA seed oil could be probably because of climatic, environmental conditions, growing, localities, and analytical conditions.

29.5.1 Sterol composition Phytosterols are important compounds which have many biological activities (Awad & Fink, 2000; Trautwein & Demonty, 2007). According to previous researches, the major sterols of N. sativa seed oil were campesterol, β-sitosterol, and stigmasterol (Menounos et al., 1986; Gharby et al., 2015). In Salama’s research (1973), the N. sativa seed oil has been found to have β- sitosterol, stigmasterol, campesterol, cholesterol, and α-spinasterol as sterols. Menounos et al. (1986) indicated that cholesterol, sitosterol, campestanol, campesterol, stigmasterol, stigmastanol, Δ5-avenasterol, Δ7-avenasterol, and Δ7-stigmasterol were the sterols of N. sativa oil. Abd Alla (1997) identified campesterol, sitosterol, and stigmasterol in the seed oil of N. sativa. In other report, β-stesterol was the major constituent of phytosterols followed by Δ5-avenasterol, and Δ7-avenasterol (Ramadan & Morsel,2002). The sterol compositions of Some N. Sativa collected from Germany and Turkey were recognized, and the results indicated that the total amounts of sterols changed from a range of 1993.07 to 2182.17 mg/kg. Moreover, the major sterols were β-sitosterol, 5-avenasterol, campesterol, ¨ zCaN, 2011). Gharby et al. (2015) studied the sterol comand stigmasterol (Matthaus & O position of N. sativa grown in Morocco. The results indicated that stigmasterol, β-sitosterol,

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and campesterol were the major sterols, and no significant difference was detected among the extracted methods. Also, the minor sterols were Δ5-avenasterol, cholesterol, Δ7-avenasterol, and Δ7-stigmasterol. From these studies, it is clear that the oils of N. sativa seeds from different areas are similar in their major sterol compositions, and the differences between the amounts of the major sterols could be likely due to localities, growing, and environmental conditions.

29.5.2 Tocopherols Tocopherols are natural antioxidants which have many biological properties (Nergiz & ¨ tles,1993). Among the main tocopherols identified in N. sativa seed oils, α, β, and γ O ¨ zCaN, 2011). Zeıtoun and Neff forms and tocotrienol are well identified (Matthaus & O (1995) indicated that the α, β, δ, and γ-tocopherol amounts in the Egyptian N. sativa seed oil were 42.90, 26.30, 4.83, and 118.70 mg/kg, respectively. Al-Saleh et al. (2006) showed that N. sativa seeds collected from different places have α and γ-tocopherols with the ¨ zCaN (2011) amounts of 5.65
11.39, and 2.26
6.95 mg/kg, respectively. Matthaus and O showed that the oils of N. sativa contained α and γ- tocopherols, and β-tocotrienol. Hassanein et al. (2011) indicated that the γ-tocopherol was main tocopherols in the oil of N. sativa seed. In another research, Hassanien et al. (2014) investigated on the tocopherol contents of nontraditional plant oils, and it was shown that the N. sativa seed oil has the highest amount of tocotrienols and γ-tocopherols. A research in N. sativa oils indicated that α-tocopherol was 45% of the total tocopherols followed by γ-tocopherol (40%) (Ramadan & Wahdan, 2012). In another research, Egyptian N. sativa oils had considerable amounts of ß- and γ-tocotrienol isomers with the amounts of 284 and 376 μg/g, respectively (Rudzinska et al., 2016). Change in the percentage of tocopherols could be because of variety of seed, storage conditions, plant cultivation, and different extraction method (Cheikh-Rouhou et al., 2007; Kiralan et al., 2014).

29.5.3 Biological activity of seed oil The seed oil of N. sativa showed stronger antioxidant activity, due to the special FA composition. Ramadan and Wahdan (2012) described that the mixtures of 10 and 20% N. sativa oil with Maize oil could improve the oxidative stability. Moreover, the addition of N. sativa oil enhanced the radical scavenging activity (RSA) of mixed oils than to Maize oil. According to the results, the inhibition of DPPH radicals was 12%
22%. Ramadan et al. (2012) estimated the RSA of the N. sativa oil using DPPH and galvinoxyl radicals. The results showed that the N. sativa oil had high RSA with approximately 57%. A similar behavior was detected in galvinoxyl radical test, N. sativa oil had antiradical activity with deactivating of 45% radicals after 1 hour. In another study, RSA of N. sativa seed oils was investigated using galvinoxyl and DPPH radicals. After one hour, N. sativa oil could deactive 25.1% of DPPH radical. N. sativa oil reduced 23.3% galvinoxyl radicals (Ramadan et al., 2003). N. sativa oil has antimicrobial property and could be recommended as natural antimicrobials. Nair et al. (2005) revealed that N. sativa oil indicated high antibacterial activity on

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Listeriamonocytogenes strains. Based on the disk diffusion method, the average zone of inhibition were between 28.2 and 39.5 mm. Ramadan et al. (2012) tested antimicrobial property of N. sativa oil against some Gram-negative and Gram-positive bacteria, and molds (yeasts and fungi). The oil of N. sativa inhibited the growth of tested microorganisms except A. lavus and A. niger. The maximum of inhibition zone for N. sativa oil was against C. albicans and S. cerevisiae (21 mm and 23 mm, respectively). According to Ugur et al. (2016) study, Turkish N. sativa oil was active against 45 isolates of S. aureus and 75 isolates of Staphylococci.

29.6 Cucurbita pepo C. pepo L. is an annual climber and its seeds oil is a source of bioactive compounds such as FAs, tocopherols, and sterols. These compounds could be applied as a potential nutraceutical or edible oil.

29.6.1 Fatty acid composition The FA composition of C. pepo oils depends on several factors, such as soil nature, and humidity, locality of cultivation, variety, climate, and development stage (Murkovic & Pfannhauser, 2000). Several studies have been done on the elucidation of the FA content of C. pepo seed oils of several areas. These investigates have indicated that the main FAs are oleic, palmitic, linoleic, and stearic acids. In a research done by Murkovic et al. (1996), the main FAs in the seed oil of C. pepo collected from Austria, Slovenia, and Hungary were oleic, palmitic, stearic, and linoleic acids with the percentages of 9.5
14.5, 3.1
7.4, 21.0
46.9, and 35.6
60.8, respectively. These four FAs represented 98% of the total identified FAs. In another study, linoleic, oleic, palmitic, and stearic acid with the amounts of 21.0
67.4, 13.7
65.2, 9.5
15.9, and 3.1%
7.4%, respectively, were the major FAs found in the seeds oil of C. pepo. The total percentages of the four FAs were between 98.1% and 98.7%. Also, the yield of oil changed from 39.5% to 54.9% (Murkovic et al., 1997). The dominant FAs found in the oil of seeds growing in Africa were palmitic (11.2%), stearic (8.0%), oleic (28.2%), and linoleic (43.0%) acids. The amount of these main FAs was between 97.7% and 99.0% of the total FA composition of the oil (Younis et al., 2000). In Gohari et al. study (2011), oleic, stearic, linoleic, and palmitic acids were the major FAs, which identified in the C. pepo seed oil and these FAs constituted up to 97% of the total FAs. The major category of identified FAs was unsaturated FAs with a total percentage of 80.7, while it had saturated FAs with the amount of 19.4%, which palmitic acid (10.7%) was the major one followed by stearic acid (7.7%). Rezig et al. (2012) indicated that palmitic acid (15.97%), linoleic acid (34.77%), and oleic acid (44.11%) were the main FAs in the seed oil of C. pepo. The indication of FAs in the different samples of C. pepo seed oil was studied by Rabrenovi´c et al. (2014). Based on the FAs composition, seed oil belongs to the oleic-linoleic type of oil. The amounts for these two main FAs changed from 37.3 to 44.5 for linoleic acid, and from 37.1 to 43.6 for oleic acid. Also, palmitic and stearic acids with the amounts of 11.2
15.5, and 5.2
6.2 g/100 g of total FAs were the two saturated FAs.

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Moreover, a small amounts of behenic, arachidonic, linolenic, palmitoleic, and myristic were detected in the C. pepo oil. The research on the FAs compositions of eight seeds oil cultivated in Algeria showed that the seeds were rich in oil and the major saturated FAs were palmitic, while the main unsaturated FAs were linoleic acid followed by oleic acid (Benalia et al., 2015). Bardaa et al. (2016) showed that the main FAs in the C. pepo L. oil seeds were palmitic acid (13.91%
20.00%), oleic acid (18.4%
39.6%), and linoleic acid (42.1%
48.5%) which account in total for about 90%.

29.6.2 Tocopherols Tocopherols are compounds which represent antioxidant molecules, and naturally found in many vegetable oils. The analysis of four tocopherols in the C. pepo seed oils indicated that the amount of gamma-tocopherol, which is the main tocopherol, was between 41 and 620 mg/kg. Also, the amount of α-tocopherol was 0 to 91 mg/kg, and δ and β are very low (Murkovic et al., 1996). In Younis et al.’s report (2000), seeds were found to be rich in α-tocopherols (3 mg/100 g). Gohari et al. (2011) resulted that the pumpkin seed oil had a high amount of tocopherols, which could give good oxidative stability during storage and processing of the oil. According to Rabrenovi´c et al. (2014) research, total tocopherol content in six samples of seed oil ranged from 38.03 to 64.11 mg/100 g. The study showed the presence of beta and gamma tocopherols in seed oil. βand gamma tocopherols contents changed from 29.92 to 53.60 mg/100 g, making 79%
84% of the total tocopherol content. Benalia et al. (2015) evaluated tocopherols content of 8 C. pepo seeds oil collected from Algeria. The data showed that the seed oils of pumpkin had high amount of tocopherols with the amount of 104.7
221.2 mg/kg of oil. The amount of β and gama tocopherols were very high in all studied C. pepo seed oils (more than 40% of total tocopherols). Moreover, δ-tocopherol with the amount of 39.1
103.0 mg/kg of oil content was the other main constituent in all oil samples. Bardaa et al. (2016) quantified the tocopherol amount in pumpkin seeds oil which was in the order of 280 mg/kg.

29.6.3 Sterols composition Sterols in vegetable oils can be either free or esterified with FAs. Based on the double bond position in the ring, sterols may be divided in Δ5- and Δ7-sterols. Most of the plants have dominant Δ5-sterols, while Δ7-sterols are presented only at small amounts of plant families such as Cucurbitaceae. The high amount of Δ7-sterols in the oils extracted from both husk and naked C. pepo seeds is an abundant advantage and could be utilized to identify the oils falsely marketed as C. pepo ones. In these researches, five Δ7-sterols were identified. According to Rezig et al. (2012) study, Sitosterol was the main sterol in the seed oil, followed by D 5,24-stigmastadienol. Also, sitosterol was the sterol marker in pumpkin seed oil, in Kalahari melon and bitter melon seed oil (Nyam et al., 2009). Rabrenovi´c et al. (2014) researched the content and composition of sterols in cold pressed pumpkin seed oils cultivated in Serbia. The results indicated that the most abundant form was Δ7,22,25stigmastatrienol. Spinasterol was the other most abundant Δ7sterol. The amount of

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spinasterol was between 18.2 and 23.3 g/100 g of the total sterol content. Spinasterol together with β-sitosterol composed 41.1
53.6 g/100 g of total sterol content. The results for sterols’ content and composition of pumpkin oil conducted by Bardaa et al. (2016) indicated that the amount of the total sterols was about 2087 ppm. β-sitosterol had about 44% of the total sterols. It was followed by Δ-5
24- Stigma stadienol and Δ-7-stigmastenol. The difference between the amount of Δ5-and Δ7-sterols could be related to the solvent applied in the extraction procedure and the maturity stage of seeds.

29.6.4 Biological activity of seed oils Cucurbita pepo seed oils have many biologically active substances such as tocopherols, sterols, and FAs. Because of these bioactive compounds, the C. pepo seed oils had antioxidant, antibacterial, antifungal, anticancer, etc. properties. Bardaa et al. (2016) showed that the seed oil obtained by cold pressure indicated high antioxidant properties because of the presence of tocopherols in higher amounts. According ´ to Nawirska-Olszanska et al. (2013) investigation, the oil extracted from the varieties of C. pepo showed well antioxidant activities irrespective of the extraction solvent used. For antimicrobial assays, Bardaa et al. (2016) research resulted that pumpkin seeds oil had higher antibacterial activity against Gram positive bacteria than Gram negative. The pumpkin oil inhibited Bacillus subtilis, and the inhibition diameter, MIC and MBC were 12 mm, 6.25 and 25 mg/mL, respectively. The oils obtained from the pumpkin seed collected from Turkey had a good antibacterial activity against Acinobacter baumannii and Klebsiella pneumonia. Also, the oil had moderate antiviral activity against Parainfluenza virus type-3, and good antifungal activity against Candida albicans (Sener et al., 2007). Research report have proven that the seed oil of C. pepo show inhibition for cancer cell breast carcinoma (MCF7) and liver carcinoma (HEPG2). The seed oil shows probable cytotoxicity against MCF7 with IC50 values in the range of 0.40
1.01 mg. Abou Seif (2014) showed that pumpkin oil could has protective effect against oxidative stress and alcohol induced hepatotoxicity.

29.7 Lallemantia spp Plants belonging to the genus Lallemantia sp. are known because of their economic features. These plants can be either served as food, industrial crop, or medicinal plant. The genus Lallemantia sp. (Balangu) belongs to the Lamiaceae family and comprises five species. Of these, L. iberica and L. royleana are mainly noticeable because of their high concentration of oil seed (approximately 30%
45%).

29.7.1 Fatty acid composition According to Khare report, the yield of oil in Lallemantia royleana seeds was 18.27%, and FA including stearic, oleic, linoleic, and palmitic acid was the constituents of seed oil. Samadi et al. (2007) determined the oil content of six Lallemantia iberica (Bieb.) varieties and concluded that palmitic, stearic, linoleic, linolenic, and oleic were the main

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constituents of the oil, and the mean amount of them were 8.07, 2.48, 17.24, 17.33, and 51.22%, respectively. From the data obtained by Komartin et al. (2019), it appears that the main components of the Lallemantia iberica oil were Linolenic (64.36%), cis-9-Oleic (13.31%), Linoleic (12.98%), and Palmitic (6.63%), which determines the remarkable properties of the oil. The FA composition of the seed of three varieties of L. iberica collected from Bulgaria was investigated (Zlatanov et al., 2012). According to the results, the content of linolenic acid was about 60%. Moreover, the amount of omega-6 linoleic acid in the oil was 12%
13%. Also, the total amount of octadecenoic FAs changed between 15% and 17%. So, linolenic, omega-6 linoleic, and octadecenoic acids comprised about 90% of the total FAs. Also, 17 FAs were recognized in sterol esters (oleic, palmitic and linoleic acids being the main components).

29.7.2 Tocopherols The tocopherol constituents of three varieties of L. iberica collected from Bulgaria were investigated and the data indicated that gamma-tocopherol were the major constituent, and alpha- and delta-tocopherols were found in trace amounts (Zlatanov et al., 2012).

29.7.3 Sterol composition In the study on the L. iberica oil by Zlatanov et al., 2012 the composition of sterol of was investigated and the results indicated that free sterols comprised almost 60% of the total sterols. Also, β-sitosterol was the main component in all studied varieties. Free and esters sterols contained the same sterols composition with only difference in their amount. Stigmasterol was significantly higher in free sterols compared to sterol esters. Hamedi et al. (2018) investigated the sterol contents of Lallemantia royleana seeds applied in Asian nutrition culture. The results indicated that the levels of phytosterols (β-sitosterol, and stigmasterol) in seed oil ranged from 4.19 mg/100 g to 9.32 mg/100 g. β-sitosterol were the major composition.

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C H A P T E R

30 Chemistry and composition of coconut oil and its biological activities Rindengan Barlina1, Kun Tanti Dewandari2, Ira Mulyawanti2 and Tjahjono Herawan3 1

Indonesian Palm Crops Research Institute (IPCRI), Ministry of Agriculture, Manado, Indonesia 2Indonesian Centre for Agriculture Postharvest Research and Development, Ministry of Agriculture, Bogor, Indonesia 3PT Riset Perkebunan Nusantara (Indonesia Plantation Institute), Bogor, Indonesia

List of abbreviations VCO ICOPRI IPCRI NYD NGD NYD RBD SKD MTT TAT PUT BIT TKT DME-FBD DME-OD DME-SD HEVCO CEVCO CCO

=Virgin Coconut Oil =Indonesian Coconut and Palmae Research Institute =Indonesian Palm Crops Research Institute =Nias Yellow Dwarf =Nias Green Dwarf =Bali Yellow Dwarf =Raja Brown Dwarf =Salak Dwarf =Mapanget Tall =Tenga Tall =Palu Tall =Bali Tall (BIT), =Takome Tall =Direct Micro Expelling-Fluid Bed Dried =Direct Micro Expelling-Oven Dried =Direct Micro Expelling-Sun Dry =Hot Extracted Virgin Coconut Oil =Cold Extracted Virgin Coconut Oil =Crude Coconut Oil

Multiple Biological Activities of Unconventional Seed Oils DOI: https://doi.org/10.1016/B978-0-12-824135-6.00025-8

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30. Chemistry and composition of coconut oil and its biological activities

30.1 Introduction Coconut is a social commodity whose development in Indonesia has traditionally been passed down from generation to generation throughout the archipelago. Coconut plants have various advantages, because all parts of the coconut plant can be used as both food and industrial raw materials. Starting from the roots, stems, midribs, leaves/sticks, spadix, coir, shells, and coconut water and moreover coconut meat, all of them can provide or increase added value. Therefore, the coconut tree is nicknamed the tree of life (Haryono, 2014; Rindengan, 2016). Coconut area in the world reaches 11.9 million ha with a production of 9.3 million metric tons of copra. Indonesia has the largest coconut area in the world, which is 3.7 million ha and produces 12 billion coconuts per year, while the Philippines has an area of 3.1 million ha and the Pacific countries around 607,000 ha (Bulai, 2015; Rethinam, 2006). Although it is called the tree of life, the kernel of the coconut is the most used. In Indonesia, coconut kernel is mainly processed into copra, crude coconut oil, desiccated coconut, and coconut milk. Coconut kernel has a very good nutritional composition, especially containing medium chain fatty acids (MCFAs), which is higher than other types of vegetable oil-producing commodities. Besides that, it contains protein and dietary fiber which are very good for health. Therefore, coconut kernel, apart from being used as raw material for cooking oil/edible oil, also has the potential to be processed into various food products. The main product with the superior health benefits of coconut is virgin coconut oil (VCO). VCO is the purest form of coconut oil, and it looks colorless, clear like water. The Asian Pacific Coconut Community (APCC) in 2003 defined VCO as oil produced from old and fresh coconut meat by mechanical and natural means, whether heated or not, without changes or damage to the oil produced. The VCO extraction process does not involve the use of chemicals, high temperatures, or ultraviolet light treatment, so it is more beneficial because all natural active components such as antioxidants, vitamins, and polyphenols can be retained. VCO has been known as the healthiest vegetable oil and can be used for various needs such as food, beverage, medicine, pharmaceuticals, nutraceuticals, and cosmetics.

30.2 Varieties of coconut According to Thampan (1981), there are two coconut varieties, namely dwarf and tall. Tall coconut varieties can reach a height of about 15
18 m and start producing at the age of 7 years. Meanwhile, dwarf coconut can reach a height of 4
5 m and start producing at the age of 3
4 years. Indonesian Coconut and Palmae Research Institute (ICOPRI) has about some of Dwarf coconut varieties, such as Nias Yellow Dwarf, Nias Green Dwarf, Bali Yellow Dwarf, Raja Brown Dwarf, Salak Dwarf. Whereas, tall coconut varieties like as Mapanget Tall (MTT), Tenga Tall (TAT), Palu Tall (PUT), Bali Tall (BIT), Takome Tall (Balai Penelitian Tanaman Kelapadan Palma Lain Balitka,2003).

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385

Fruits of dwarf coconut are small, the average ripe fruit weighs only 748
907 g, and the meat/kernel ranges from 260 to 344 g. While fruit of tall coconut around 974
2063 g and the kernel 362
976 g (Balai Penelitian Tanaman Kelapadan Palma Lain Balitka, 2003). Furthermore, the kernel after being processed into copra has an oil content of 64% at TAT (Novarianto, 2003), PUT 69.29% (Tulalo, 2003), and BIT 65.6% (Tenda, 2003). Generally, the kernel of tall coconut is processed into copra, desiccated coconut, and coconut milk, while dwarf coconut fruit has been developed as a source of sap for sugar raw materials. At this time, kernel of dwarf coconut has begun as raw material for processing ball copra or edible copra.

30.3 Processing of coconut oil In principle, there are two ways to produce coconut oil, namely the wet method with fresh coconut raw materials and the dry method with copra as raw material. Dry processing uses copra as raw material. The quality of the oil produced depends on the quality of the copra used. Dry processing is usually carried out on a medium and large industrial scale. However, the pressed oil is not ready for consumption, so it must be purified first because the quality of the raw material is not uniform and sometimes contains harmful compounds that dissolve in oil.

30.3.1 Wet process Wet oil processing through the coconut milk production stage, with gradual heating at controlled temperatures, has been carried out by the ICOPRI. Coconut oil has a water content of 0.02%
0.03%, a free fatty acid content of 0.02%, is colorless, and smells good (Lay &Rindengan, 1989). Then in coconut oil processing where the testa is not removed, the moisture content and free fatty acid content up to 2 months of storage are still around 0.03% (Karauw et al.,2014). According to Hagenmaier (1977), the oil conditions are categorized as natural or clear oil. In a further development, the coconut oil produced is called VCO. Bawalan (2002) states that VCO is a coconut oil product that is naturally processed from fresh coconut kernel or its derivatives (coconut milk and fresh residue) which have not gone through further processing such as refining. Wet oil processing with gradual heating is as follows: (Rindengan, 2000). 30.3.1.1 Prepare of raw material The coconuts that will be processed into oil are old coconuts, which are 11
12 months old, which is marked by brown coir skin. Ripe coconut fruit will produce high oil yield. We recommend using the type of tall coconut. 30.3.1.2 Processing of milk Mature coconut fruit is peeled, split then shredded manually, or the kernel is removed from the shell and then the kernel is ground using a coconut milling machine or shredded.

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30. Chemistry and composition of coconut oil and its biological activities

Crushed fruit kernel added with water in a ratio of 1: 2. Then the extract is shaken and then squeezed and filtered until coconut milk is obtained. We recommend that grate and squeeze the coconut milk using a coconut grater and a coconut press. 30.3.1.3 Separation cream (rich in oil) The coconut milk obtained is poured into a transparent plastic bucket, then let stand for 3 hours. During this time, coconut milk will be divided into three layers, namely the top layer is the cream (rich in oil), the middle layer is the skimr (rich in protein), and the bottom layer is the sediment. Based on the results of research from 30 MTT fruit, obtained 16 kg of kernel (average kernel weight 500 g/fruit). After making coconut milk (in the same way as above), coconut milk obtained about 48 L. Furthermore, during the 3 hours of incubation, the cream that is in the middle layer is removed by suctioning it using a plastic tube. The cream obtained is about 10 L. 30.3.1.4 Gradual heating Heating milk

The cream obtained is heated using a frying pan until it boils with a heating temperature ranging from 100 C to 110 C. After the oil is rather cooked, it is indicated by the separation of the “blondo” and oil (the blondo is still white), cooled and then filtered so that the oil is obtained. The results showed that from 10 L of cream heated obtained 3,750 mL oil, the duration was around 3 hours, using 3 L of kerosene fuel (Rindengan, 2000). Furthermore, the “blondo” is separated by filtering. Blondo which is a by-product still contains about 10%
15% oil. Heating oil

Uncooked oil is heated to the same heating temperature as cream. At this stage, it is done until a slightly clear oil is obtained and if there is still blondo the color must be light brown. Furthermore, the oil is cooled and filtered using filter paper. The final product obtained is VCO.

30.3.2 Dry process Processing of coconut oil in the dry method begins with the kernel being processed into copra, both copra which is obtained through smoking and drying using an oven or direct heating in the sun. In general, copra that is processed at the farmer level is by means of a smoking process, so to obtain coconut oil that is ready for consumption, further processes such as Refined, Bleaching, and Deodorization (RBD) are needed. The RBD process has an impact on decreasing the quality of oil, including the destruction of health-supporting micro-constituents (Dewi & Hidajati,2012). If processing coconut oil using white copra, it takes 27 hours to dry the copra (Lay & Maskromo, 2016). Currently, developing oil processing technology with the Direct Micro Expelling-Oven Dried (DME-OD) system with a temperature of 40OC requires oven time for 4 hours once the process is obtained with a moisture content of 0.10% and Direct Micro Expelling-Sun Dry (DME-SD) with a water content of 0.17% (Ghani et al.,2018).

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30.4 Physico-chemical properties of coconut oil

Meanwhile, Direct Micro Expelling-Fluid Bed Dried (DME-FBD) is a method of processing coconut oil with a flat bed drying system. The DME method has been developed by Dan Etherington (2016) in Vanuatu, Solomon Island, Fiji, and Asia Pacific. The advantage of this method is that it is hygienic, the energy comes from biomass waste such as shells, coir, and wood waste so that it is environmentally friendly and cheap. Indonesian Palm Crops Research Institute (IPCRI), since 2018, has adopted Direct Micro Expelling-Fluid Bed Dried (DME-FBD) technology. The results of the study using Coconut In Mapanget (DMT) yielded a VCO yield of 18.39% from 16 coconuts and Quick Salak (GSK) coconuts, 16.38% VCO yield of 26 coconuts (Pradhana, et al., 2019).

30.4 Physico-chemical properties of coconut oil The physical and chemical properties of oil are very useful parameters to determine the proper use of the oil or to evaluate the stages of a processing and the quality of the oil (Fardiaz, 1991). The various uses of oil in products are largely determined by both physical properties and their chemical properties. The physical properties of oil include color, boiling point, softening point, slipping point, specific gravity, refractive index, smoke point, solubility, melting point, odor, and flavor (Kirchenbauer, 1960). Furthermore, based on chemical properties, oil is a triglyceride consisting of glycerol groups and fatty acids. Thus, the chemical properties of oil are largely determined by the glycerol properties of these fatty acids. The most important chemical properties are the hydrolyzed and oxidized properties, which are determined by measuring the acid value and the peroxide value, respectively. Another chemical property is the type of fatty acid, determined by the saponification number and the characteristic of saturation is the iodine value. In Table 30.1, we can see some of the physicochemical properties of coconut oil compared to palm oil, palm kernel oil, and soybean oil.

TABLE 30.1

Physicochemical properties of coconut, soybean, palm, and palm kernel oil.

Properties

Coconut oila

Palm oilb

Palm kernel oilb

Soybeanc

Density (g/kg)

0.920

0.900

0.900
0.910

0.910
0.920

Refractive index

-

1.456
1.458

1.415
1.495

1.471
1.475

17










Melting point ( C)

14










Iodine value

7.95

48
56

14
20

117
141

Saponification value

261.50

196
205

244
254

189
195

Unsaponifiable matter (%)

-







0.50
1.60

Acid value (%)

0.46







0.30
3.00



Cloud point ( C) 

Source: aRindengan and Novarianto (2004), bKirchenbauer (1960), cKetaren (1986).

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30. Chemistry and composition of coconut oil and its biological activities

30.5 Composition of coconut oil 30.5.1 Fatty acids composition Fatty acids are distinguished according to the degree of unsaturation of the carbon atom bonds and the chain length of the carbon atoms. The following shows the types and content of fatty acids in coconut oil compared to other vegetable oils (Table 30.2). Based on the number of carbon atoms, fatty acids can be divided into MCFAs (C6
C12) and long chain fatty acids (C14
C24). From Table 30.2, it can be seen that coconut oil and palm kernel oil are classified as medium chain triglycerides (MCTs) and are also often referred to as types of lauric oil. Meanwhile, palm oil and soybean oil are classified as long chain triglycerides (LCTs) (Rindengan, 1993). Furthermore, based on the degree of unsaturation, fatty acids can be classified as monounsaturated fatty acids, for example, oleic acid which is found in palm oil and soybean oil, and polyunsaturated fatty acids, such as linoleic and linolenic fatty acids which are found in soybean oil. Coconut oil is classified as saturated fatty acids.

30.5.2 Micronutrient component of coconut oil Considering that coconut oil has various health benefits, in current developments it is more directed as a health product. Therefore since 2003, various processing processes have been developed to produce higher quality coconut oil. Coconut oil that is processed under control is called VCO. In 2005, the APCC issued a quality standard for VCO (Table 30.3). Therefore, VCO is intended for consumption as a nutraceutical. Although until now the functional components contained in VCO are still being studied, the health role of VCO TABLE 30.2 Kinds and content of fatty acids coconut, soybean, oil palm, and palm kernel oil. Fatty acids

Atom C number

Coconut (%)a

Soybean (%)b

Oil palm (%)b

Palm kernel oilc

Caproic

C6










0.3

Caprylic

C8

0.25







3.9

Capric

C10

5.05







4.0

Lauric

C12

55.90







49.6

Myristic

C14

22.20




1.23

16.0

Palmitic

C16

8.88

14.04

41.78

8.0

Stearic

C18

2.21

4.07

3.39

2.4

Oleic

C18:1,n-9

4.38

23.27

41.90

13.7

Linoleic

C18:2,n-6

1.18

52.18

11.03

2.0

Linolenic

C18:3,n-3




5.63







Arachidonic

C20













Source: aRindengan, et al. (2011), bChowdhury, et al. (2007), cKintanar (1990).

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30.5 Composition of coconut oil

TABLE 30.3

Quality of virgin coconut oil (Asian & Pacific Coconut Community APCC, 2005).

No.

Parameter

Amount

1.

Characteristic -Relative density

0.919
0.920 

-Refractive index 40 C

1.4480
1.4492

-Moisture content (%)

0.1
0.5

-Insoluble impurities (%)

0.05

-Soap value,

250
260

-Iodine number

4.10
11.00

-Unsaponifiable matter (%), max

0.20
0.50



2.

3.

4.

-Density/30 C

0.915
0.920

-Free fatty acid/(%), max

0.50

-Polenske number, min

13

Fatty acid composition(%): C6:0

0.4
0.6

C8:0

5.0
10.0

C10:0

4.5
8.0

C12:0

43.0
53.0

C14:0

16.0
21.0

C16:0

7.5
10.0

C18:0

2.0
4.0

C18:1

5.0
10.0

C18:2

1.0
2.5

C18:3-C24:1

,0.5

Quality characteristic -Color

no

-Free fatty acid (%)

0.5

-Peroxide number (meq/kg sample), max

3

-Microbe total

,10 cfu

-Odor

Rancid odor free

Metal contamination (mg/kg) -Fe

0.5

-Cu

0.4

-Pb

0.1

-As

0.1

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30. Chemistry and composition of coconut oil and its biological activities

has been widely reported. Dr. Mary Enig and Dr. Bruce Fife and several other researchers reported that the functional properties of VCO are from MCTs, especially laurine. Furthermore, some researchers suspect that there is a synergistic effect of laurine and trace compounds contained in VCO, so that it has a higher health effect than coconut oil processed from copra. Several researchers reported the micronutrient components in coconut oil, both processed by heating and without heating (cold process) (Table 30.4). According to Table 30.4, higher temperatures favor the incorporation of more phenolic substances which may be the reason for higher phenolic substances in HEVCO. It has already been reported that due to application of temperature (100 C) during extraction leads to evaporation of water from coconut milk emulsion and incorporation of phenolic substances (Marina et al., 2009; Seneviratne & Sudarshana,2008). In the CEVCO, the phenolic substances are not incorporated due to the mild temperature condition. However, in the extraction method the temperature of the coconut milk emulsion reaches above 100 C.

30.6 Virgin coconut oil composition Coconut oil has a high content of MCFAs, which is about 90% with a lauric acid content of about 50% followed by other fatty acids. The fatty acid content of coconut oil is strongly influenced by the processing process. Karauw et al. (2014) used two coconut varieties, Salak Hibrida and Dalam Mapanget. VCO extraction from coconut milk used the centrifugation method. The results of this study indicate that Salak Hibrida does not produce VCO, while Dalam Mapanget has a VCO yield of 7.43% and contains high amounts of lauric acid (Tables 30.5 and 30.6). The peroxide value is a measure of the concentration of peroxides and hydro peroxide forms in the initial stage of lipid oxidation. The number shows the oxidative level and rancidity. VCO has low content of unsaturated fatty acids, so it has low oxidation. Unsaturated fatty acids are unstable because of its peroxide and easily become rancid. The iodine value is expressed as the number of grams of iodine absorbed by 100 g of the fat under the test conditions used. The iodine value of VCO samples is 7.24, this is shows that VCO has high degree of saturation. The value of iodine in the VCO of Mapanget Tall (MTT) is still within the range of values recommended by the APCC TABLE 30.4 Tocopherol, polyphenol, antioxidant activity of virgin coconut oil by different process (Srivastava et al., 2016). Chemical parameter

HEVCO

CEVCO

CCO

Tocopherol (ug/g)

17.87

27.65

3.72

Polyphenol (ug/g)

650.35

401,.23

182.82

Antioxidant activity

85.12

68.33

39.32

Monoglyceride (%)

1.65

2.89

0.31

Phytosterol (ug/g)

2.86

2.25

0.24

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30.6 Virgin coconut oil composition

TABLE 30.5

Physical and chemical characteristics of VCO from Mapanget Tall coconut.

Parameter

Mapanget Tall

APCC standard

Color

Clear

Clear

Odor

Not rancid

Not rancid

Number of peroxides (meq/kg)

0.73

# 3.0

Moisture content (%)

0.11

# 0.5

Iodine number (g iod/100 g)

7.24

4.1
11.0

Saponification value

255.67

250
260

TABLE 30.6

Coconut fatty acid profile of Mapanget Tall.

Fatty acid

% Fatty acid Mapanget Tall

APCC standard

C8:0

7.2

5
10

C10:0

6.2

4.5
8.5

C12:0

48.6

43
53

C14:0

19.5

16
21

C16:0

9.1

7.5
10

C18:0

2.4

2
4

C18:1

5.6

5
10

C18:2

1.4

1
2.5

standard. The saponification shows the average molecular weight of all the fatty acids. High saponification value shows the shorter fatty acids. Table 30.6 shows that lauric acid (C12: 0) is the most dominant fatty acid in coconut oil, which is 48.6% followed by myristic fatty acid (C14) of 19.5%. Marina et al. (2009) explained that the content of commercial VCO from Indonesia showed levels of lauric acid around 46.64%
47.85% and myristic acid around 17.03%
18.90%.

30.6.1 Lauric acid Lauric acid is a type of MCFAs that is dominant in coconut oil. In the body, lauric acid will change its form to monolaurin to make it more functional in maintaining health. Several studies have shown that lauric acid and other fatty acids such as capric acid, palmitic acid, myristic acid, linoleic acid, and linolenic acid can inhibit the growth of Pneumococcus, Streptococcus, Micrococcus, Candida, S. aureus, S. epidermis. Lauric acid only requires a concentration of 0.062 micro mol/mL to inhibit Pneumococcus. As for capric acid and myristic acid, respectively, 1.45 and 0.218 micro mol/mL are needed to inhibit

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the same microbes. The results of the lauric acid antibacterial activity test from coconut endosperm showed that the minimum inhibitory concentration of lauric acid against Salmonella sp., E. Coli, and Staphylococus aureus bacteria was at a concentration of 3.13%. As for Micrococcus 10%, Bacillus stearothermophilus 30%, and Pseudomonas 50% (Su’i and Sumaryati, 2014). Several studies have suggested that some MCFAs disrupt the bacterial cell wall or membrane to protect host cells against infection (Matsue et al., 2019).

30.7 Biological activities of coconut oil Various health role has been widely reported VCO, VCO reportedly contains medium chain triacylglycerol (medium chain triacylglycerol/MCT) in particular has a coefficient digestibility laurin the maximum so that this component is more quickly digested than other types of fat. This is because MCT has a smaller size than the LCT (long chain triacylglycerols) which may facilitate the action of pancreatic lipase that will be hydrolyzed faster and more completely than other fats. Therefore, the VCO more quickly absorbed body (Oopik et al., 2001 and Nevin & Rajamohan, 2006). Although many reported health benefits of VCO, but the taste VCO "oily" and a little sour causing VCO unacceptable of consumer. Therefore, it must be another product processing technology that is derived from the basic ingredients of VCO, to increase consumer acceptance. As a basic ingredient in food and pharmaceutical products, processing VCO into such products must not damage the functional. VCO functionality lies in the content of MCT, in particular laurin and unsaponification components such as vitamin E, provitamin A, polyphenols, and phytosterol. The results of the research by Fatimah and Rindengan show that the use of 25% VCO and 25% fruit juice in the processing of pineapple flavored VCO emulsion, fat content is 26.5%, iodine value 9.76 and peroxide value 0.39 meq/kg of oil, and the composition of fatty acids as in Table 30.7. Furthermore, in the processing of ice cream with the use of 15% VCO, it produces a product with a fat content of 16.19%, and a fatty acid composition as in Table 30.7. With the availability of products that have been substituted with VCO, it is expected to have an impact on consumer health. Furthermore, the results of VCO-emulsion testing on body weight and lipid profile of white rats have been reported by Fatimah and Rindengan (2011).

30.7.1 Weight development of white rats The results of the study on body weight of treated rats, both VCO and VCO emulsion, experienced a smaller increase in body weight than the control (VCO 5 13.25 g, VCO emulsion group 5 4.4 g, while the control group 5 38.22 g). This is in accordance with the opinion of Fife (2005) which states that the VCO diet can maintain body weight. Furthermore, it is said that VCO is an oil that contains high MCTs so that it is not stored in the body as fat. Furthermore, it is said that MCT, especially laurine, has a maximum digestibility coefficient so that this component is digested and absorbed by the digestive system faster than other types of fat (Nevin & Rajamohan, 2006; Oopik et al., 2001). Of the three diet groups,

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393

30.8 Summary

TABLE 30.7

Kinds and content of fatty acids VCO-emulsion and ice cream-VCO.

Fatty acids

Atom C number

VCO-emulsion (%)a

Ice cream-VCO (%)b

Caproic

C6







Caprilic

C8

5.51

3.28

Caproic

C10

5.72

2.28

Lauric

C12

47.14

18.05

Miristic

C14

19.46

7.49

Palmitic

C16

10.37

9.69

Stearic

C18

3.10




Oleic

C18:1,n 2 9

7.13

9.95

Linoleic

C18:2,n 2 6

1.55

3.83

Linolenic

C18:3,n 2 3




0.09

Arahidonic

C20







Source: aFatimah and Rindengan (2011), bRindenganet al. (2011).

the group with the lowest weight gain was the group of rat with the VCO emulsion diet. This is thought to be due to the fiber content of pineapple juice.

30.7.2 Cholesterol profile of white rat The VCO-Emulsion and VCO diets with the same VCO levels have the same effect in reducing total cholesterol levels, increasing HDL cholesterol levels, lowering LDL cholesterol levels, and lowering rat blood triglyceride levels. The health role of VCO-Emulsion is thought to be due to the presence of medium chain triacylglycerol (MCT), especially laurine which has a maximum digestibility coefficient so that this component is digested more quickly than other types of fat and is not synthesized in the body into cholesterol (Nevin & Rajamohan, 2006; Oopik et al., 2001). Furthermore, Fife (2005) states that laurine can encourage LCT to be metabolized more quickly. Furthermore, Supriatna (2008) reports the effect of VCO processing on blood glucose in diabetic rats. The results showed that the difference in the process did not affect the percent change in glucose levels in rats with diabetes mellitus, but it could reduce the blood glucose levels of rats with diabetes mellitus to a level below 200 mg/dL, while coconut cooking oil did not reduce blood glucose levels in rats with diabetes mellitus to a level below 200 mg/dL.

30.8 Summary Coconut plants have various advantages, because all parts of the coconut plant can be used both as food and industrial raw materials. The kernel of the coconut is the most

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used. Coconut kernel has a very good nutritional composition, especially containing MCFAs, which is higher than other types of vegetable oil-producing commodities. Besides it contains also protein and dietary fiber which are very good for health. Lauric acid is a type of MCFA that is dominant in coconut oil which is 48.6% followed by myristic fatty acid (C14) of 19.5%. MCT, especially laurine, has a maximum digestibility coefficient so that this component is digested and absorbed by the digestive system faster than other types of fat. Diets with the MCT levels reducing total cholesterol levels, increasing HDL cholesterol levels, lowering LDL cholesterol levels, and lowering blood triglyceride levels.

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9, Nomor. Bulai, S. (2015). Use of coconut oil amongst the Pacific Islands. Cocoinfo International, 22(2), 38
41. Chowdhury, K., Banu, L. A., Khan, S., & Latif, A. (2007). Studies on the fatty acid composition of edible oil. Bangladesh Journal of Science and Industrial Research, 43(3), 311
316. Dewi, M. T. I., & Hidajati, N. (2012). Peningkatan mutu minyak goreng curah menggunakan adsorben bentonit teraktivasi. Journal of Chemistry, 1(2), 47
53. Etherington, D. (2016). Coconut comeback-sea change? Innovation to realise the potential of virgin coconut oil. XLVII APCC cocotech conference and exhibition, 26
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368. Fardiaz, D. (1991). Instrumental analysis of edibel fats and oils. An overview. BPIHP. Bogor. Fatimah, F., & Rindengan, dB. (2011). Pengaruh diet emulsi virgin coconut oil (VCO) terhadap profil lipid tikus putih (Rattus norvegicus). Jurnal Littri, 17(1), 18
24. Fife, B.C.N.N.D. (2005). Coconut oil miracle. PT. Bhuana Ilmu Populer. Kelompok Gramedia, Jakarta. Hal35
138. Ghani, N. A. A., Chammip, A. A., Hwa, P. C. H., Ja’afar, F., Yasin, H. M., & Usman, A. (2018). Physicochemical properties, antioxidant capacities, and metal content of virgin coconut oil produced by wet and dry processes. Food Science and Nutrition, 6, 1298
1306. Hagenmaier. H. (1977). Coconut aqueous processing. University of San Carlos, Cebu City, Philippines. Haryono (2014). Penelitian pengembangan bioindustri kelapa berkelanjutan mendukung ketahanan pangan yang tangguh dan berdaya saing. Prosiding Konperensi Nasional kelapa VIII. 21
22 Mei 2014. Halaman 11
18. Karauw, S., Indrawanto, C., & Kapuallo, M. L. (2014). Karakteristik virgin coconut oil dengan metode sentrifugasi pada dua tipe kelapa. Buletin Palma, 15(2), 128
133. Ketaren, S. (1986). Pengantar teknologi minyak dan lemak pangan. Jakarta: Ui Press, 315 Halaman. Kintanar, L. K. (1990). Coconut oil: A source of metabolic energy. Coconut Today. Special edition. Manila. Kirchenbauer, H. G. (1960). Fats and oils (Second edition). New York: Reinhold Publ. Corp. Lay, A., & Maskromo, I. (2016). Kinerja alat pengering kopra sistem oven skala kelompok tani dan karakteristik produk. Buletin Palma, 17(2), 175
183. Lay, A., & Rindengan, d. B. (1989). Pengolahan minyak kelapa dengan pemanasan bertahap. Terbitan Khusus No.15/ VIII/1989. Balitka Manado. Hlm. 89
90. Marina, A. M., Man, Che, Nazimah, Y. B., & Amin, I. (2009). Antioxidat capacity and phenolic acids of virgin coconut oil. International Journal of Food Sciences and Nutrition, 60, 114
123. Available from https://doi.org/ 10.1080/09637480802549127. Nevin, K. G., & Rajamohan, T. (2006). Virgin coconut oil supplemented diet increase the antioxidant status in rats. Food Chemistry., 99, 260
266. Novarianto, H. (2003). Monograf Plasma Nutfah Kelapa Indonesia. Badan Penelitian dan Pengembangan PertanianPusat Penelitian dan Pengembanagn Perkebunan. pp. 56
60.

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Oopik, V., Timpmann, S., Medijainen, L., & Hemberg, H. (2001). Effect of medium chain triglyceride ingestion on energy metabolism and endurance performance capacity in well-trained runners. Nutrition Research (New York, N.Y.), 21, 1125
1135. Pradhana, A. Y., Maskromo, I., Utomo, N., Manaroinsong, E., Karouw, S., & Rindengan, B. (2019). Optimasi produksi virgin coconut oil dengan metode direct micro expelling. Buletin Palma, 20(2), 91
99. Rethinam. P. (2006). Coconut water natures health drink. APCC. Jakarta. pp. 35. Rindengan, B. (1993). Kontroversi isu minyak tropis, Balai Penelitian Kelapa Buletin Balitka, 20, 1
12. Rindengan, B. (2000). Pengolahan minyak kelapa murni. Makalah Disampaikan pada Pelatihan Petugas dan petani ADP II Loan OECF IP—454 Dinas Perkebunan Propinsi Sulawesi Utara 22
23 Nopember 2000. Rindengan, B. (2016). Processing of some food products based on coconut. Paper in international training on coconut product development. 27 May
4 June 2016. Manado-Indonesia. Rindengan, B., Karouw, S., & Pasang, P. (2011). Penggunaan virgin coconut oil (VCO) sebagai substitusi lemak pada pengolahan es krim. Buletin Palma, 12(1), 66
73. Rindengan, B., & Novarianto, d.H. (2004). Pembuatan dan pemanfaatan minyak kelapa murni (Virgin Coconut Oil). Seri Agritekno. Penerbit Penebar Swadaya. 79 Halaman. Seneviratne, K. N., & Sudarshana, D. D. M. (2008). Variation of phenolic content in coconut oil extracted by two conventional methods. International Journal of Food Science and Tecknology, 43, 597
602. Available from http:// doi.org/10.1111/ifs.2008.43.issue-4. Srivastava, Y., Semwal, A. D., & Majumdar, A. (2016). Quantitative and qualitative analysis of bioactive components present in virgin coconut oil. Cogent Food & Agriculture, 2, 1
13. Available from http://doi.org/10.1080/ 23311932.2016.1164929. Supriatna, D. (2008). Pengaruh proses pembuatan Virgin Coconut Oil (VCO) terhadap aktivitasnya sebagai penurun kadar glukosa darah pada tikus diabetes melitus. Tesis Sekolah Pascasarjana, IPB. Bogor. 120 Halaman. Tenda, M. (2003). Monograf Plasma Nutfah Kelapa Indonesia. Badan Penelitian dan Pengembangan Pertanian-Pusat Penelitian dan Pengembangan Perkebunan. p66
70. Tulalo, M. (2003). Monograf Plasma Nutfah Kelapa Indonesia. Badan Penelitian dan Pengembangan Pertanian-Pusat Penelitian dan Pengembanagn Perkebunan. p61
65.

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C H A P T E R

31 Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil Serkan Selli1,3, Gamze Guclu1, Onur Sevindik2,4 and Hasim Kelebek2 1

Department of Food Engineering, Faculty of Agriculture, Cukurova University, Adana, Turkey Department of Food Engineering, Faculty of Engineering, Adana Alparslan Turkes Science and Technology University, Adana, Turkey 3Department of Nutrition and Dietetics, Faculty of Health Sciences, Cukurova University, Adana, Turkey 4Central Research Laboratory (CUMERLAB), Cukurova University, Adana, Turkey

2

31.1 Introduction Hazelnut (Corylusavellana L.), belonging to Betulaceae family, is the second most produced nut among hard-shelled fruits in the world after almond. It was first cultivated in the Anatolian region of Turkey. It is known to expand to Greece and to Italy afterwards through the Roman Empire following an outspreading all over Europe around Middle Ages. In the late 1500s, Spain presented it to America continent (Lemoine, 1998). Although there exist various types of hazelnut trees belonging to the Corlyus genus (such as; Corylus americana, C. avellana, C. heterophylla, C. yunnanensis, C. colchica, C. cornuta, C. maxima, C. sieboldiana, (syn. C. mandshurica) C. chinensis, C. colurna, C. fargesii, C. jacquemontii, C. wangii, and C. ferox.), many of them are wild and do not possess any economic importance (Botta et al., 2019). The most common and important member of Corylus genus, Corylusavellana, namely Turkish hazelnut, is mainly grown in the coastal areas of the Black Sea region of Turkey. Italy, Spain, the USA, Georgia, Chile, Azerbaijan, and Iran are the other hazelnut producer countries where the risk of frost is rare and the average temperature does not get below 28 C in winters and above 36 C
37 C in summers. According to data released in 2019, Turkey (776,046 ton), Italy (98,530 ton), Azerbaijan (53,793 ton), and the USA (39,920 ton)

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© 2022 Elsevier Inc. All rights reserved.

398

31. Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil

are the most leading countries in shelled hazelnut production. Turkey met about 75% of the total worldwide hazelnut production within same year (FAO, 2019). Hazelnut is used as a snack and also as an ingredient in many food stuffs like confectionery and patisserie in different forms. It is mostly consumed after roasting with their distinguished burnt, coffee-like, roasty, and chocolate-like odor characteristics. As a result of roasting treatment, numerous reactions and significant changes occur both in its textural properties and organoleptic characteristics. Lipids, proteins, carbohydrates, vitamins, minerals and sterols are the main components of hazelnut and the amounts of them differ with the hazelnut cultivar. The seed kernels accumulate a significant amount of oil (more than 60%) especially during the second phase of its maturation (Brufau et al., 2006). There have been various studies to elucidate the health-promoting activities of lipophilic bioactive compounds existed in hazelnuts with different cultivars (Alasalvar et al., 2009; Mercanligil et al., 2007). Hazelnuts are also processed into edible oil due to its lipid content, bioactive compounds, and powerful flavors in hazelnut producer countries in recent years. Hazelnut oil is progressively taking interest by using as an incipient oil product rich in oleic acid and beneficial dietary properties. This product is broadly used in cooking, deep frying, salad dressing, and as flavoring ingredient. Current chapter reviews the research work carried out in recent years on the biochemical properties (fatty acids, aroma, aroma-active and phenolic compounds) of hazelnut oils in addition to their antioxidant capacity and antimicrobial activities.

31.2 Fatty acid composition of hazelnut oils Edible oils are biological blends of different origins consisting of esters consisting glycerol with fatty acids. The physicochemical composition of these oils is significantly affected from the form and ratio of the fatty acids on the triglyceride form. The amount and profile of the fatty acids with the ratio of unsaturated and saturated fatty acids is a key factor for the nutritive value of the oil. Fatty acids are classified into two groups including saturated, mono-unsaturated (MUFA), and polyunsaturated (PUFA) fatty acids depending upon the existence of double bonds. The unsaturated groups are divided into classes known as omega, of which the ω-9 is considered as nonessential for humans and the ω 2 3 and ω 2 6 as essential fatty acids since these are not synthesized by mammals and hence, they must be regularly taken into the human body (Dorni et al., 2018; Kostik et al., 2013). Cis-structure fatty acids are nutritionally significant and through the hydrogenation process of fats and oils, some of the cisforms can be transformed into trans form which have negative effect on serum lipoproteins and raise coronary heart disease risk (Aro et al., 2006). Thus, the metabolism, profile, and concentration of the fatty acids have a substantial role in terms of health. Hazelnut oil is a good source of MUFA and PUFA and relatedly have valuable impacts for the inhibition of heart diseases and therefore, consistent eating of nuts can decrease the occurrence of such diseases and increase longevity (Crews et al., 2005). Comparing hazelnut oils from different countries in Table 31.1, hazelnut oil is seen to be a better source for oleic acid (18:1ω9) having more than 80% of all fatty acids; linoleic (C18:2), palmitic (C16:0), and stearic (C18:0) acids are followed. Oleic acid is known to be an important cholesterol reducing bioactive compound in blood while linoleic acid has preventive effects against intravascular narrowing Multiple Biological Activities of Unconventional Seed Oils

399

31.2 Fatty acid composition of hazelnut oils

TABLE 31.1

Fatty acid composition of hazelnut oils in important producer countries.

Compounds

China

France b

Italy

Spain

Turkey

Miristic acid (C14:0)

nd

tr-0.1

nd

nd

0.04f

Palmitic acid (C16:0)

4.34a

5.0
6.3b

5.8
6.6b

4.80
6.48c,d

3.84
4.86e,f

Margaric acid (C17:0)

nd

tr-0.1b

tr-0.1b

nd

0.03f

Heptadecenoic acid (C17:1)

nd

0.1b

0.1b b

nd b

nd c,d

Stearic acid (C18:0)

nd

1.6
2.9

2.4
2.8

1.64
3.05

1.73
2.72e,f

Palmitoleic acid (C16:1)

0.22a

0.2
0.3b

0.2
0.3b

0.17
0.40c,d

0.09
0.12e,f

Oleic acid (C18:1)

84.57a

75.6
81.9b

80.3
83.4b

77.05
84.05c,d

84.30
84.51e,f

Linoleic acid (C18:2)

10.06a

9.4
17.1b

6.2
10.6b

6.62
14.99c,d

7.43
10.04e,f

Linolenic acid (C18:3)

0.11a

tr-0.4b

0.1
1.0b

0.08
0.25c,d

0.06
0.12e,f

Arashidic acid (C20:0)

0.20a

0.1b

0.1
0.2b

0.11
0.16c,d

0.08
0.16e,f

Eicosenoic Acid (C20:1)

nd

0.1
0.2b

0.1
0.2b

0.13
0.22c,d

0.06
0.13e,f

Behenic acid C22:0

nd

nd

nd

0.02
0.20c,d

0.04
0.05e,f

Tetracosenic acid (C24:1)

nd

nd

nd

nd

0.04f

a

Cui et al. (2020) China. Crews et al. (2005). c Bada et al. (2004). d Parcerisa et al. (1995). e Dumanand O¨zcan (2020). f Turan (2018). nd, Not detected; tr, trace. b

(Alasalvar et al., 2009). The oleic acid proportion in Chinese, French, Italian, Spanish, and Turkish hazelnut oils differs within 75.6 and 84.6 while the ratio of linoleic acid is between 6.2 and 17.1 (Table 31.1). Owing to its oleic acid content and antioxidant components, this oil can be very resistant to oxidation reactions through processing or storing (Alasalvar et al., 2009; Choe & Min, 2006). Solak et al. (2018) investigated the oxidation kinetics of the refined hazelnut oil heated from 80 C to 180 C and reported that its fatty acid and minor components affected the oxidative stability of the oil and chemical refining process did not resulted in any important changes in its fatty acid profile. Durmaz and Go¨kmen (2019) elucidated the impact of refining on fatty acids, phytochemicals, antioxidant activity, and oxidative stability of hazelnut oil samples. The main fatty acids of hazelnut oil in this study were found to be oleic, linoleic, palmitic, and stearic acids and these compounds were not decreased significantly during the five steps of the refining process. Cittadini et al. (2020) studied the oil composition of some hazelnut cultivars in an innovative, nonconventional crop environment in north-western Patagonia from Argentina. Authors reported that oil contents of the samples were between 66% and 72% and oleic acid prevailed (78.4%
84.4%) in hazelnut oils. As a result of the study, it was reported that the level of oleic acid in the oils of different hazelnut oil cultivars used in the analysis had small differences between them depending on geographical origin. Multiple Biological Activities of Unconventional Seed Oils

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31. Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil

31.3 Volatile composition and key odorants of hazelnut oil The main criteria taken into account by consumers in evaluating the quality of foods are obviously the appearance, color, taste, and aroma. Aroma compounds generally perceived through the nose and nasal passages have a substantial role in these quality parameters and are known also to have an effect the flavor (Guichard, 2002). The most important properties of aroma compounds, whose amount varies between nanograms and milligrams, are the sensory perception they create even at minor amounts that play a decisive role in quality. The aroma of a product can be evaluated by sensory methods, however, since this evaluation is subjective and depends on the person, the results may be inaccurate. For this reason, precise instrumental devices such as gas chromatography and mass spectrometry (GC-Ms) should be used in the qualitative and quantitative detection of aroma compounds reliably and the results should be supported by sensory analysis (Buttery, 1981; Pino & BarzolaMiranda, 2020). Hazelnut (Corylusavellana L.) in the tree nut class has attracted both the producers and the researchers in terms of the study of its characteristic flavor comprised of taste and aroma and hence it is a product preferred broadly in the food sector (Kiefl et al., 2013). Hazelnut is a nut that can be eaten both raw and roasted, but the latter counterpart is mostly the favored form. Its characteristic odor is due to the mixture of different volatiles. Ketones, aldehydes, alcohols, aromatic hydrocarbons, and furans constitute a significant part of these compounds (Alasalvar et al., 2004; Wickland et al., 2001). An eminent characteristic key odorant of roasted hazelnut is filbertone (5-methyl-(E)-2-hepten-4-one) having a “roasted hazelnut like” note and occurs as a result of roasting (Langourieux et al., 2000; Pfnuer et al., 1999). This compound is of high importance due to its extremely low odor threshold value which is 5 ng/kg. In a comparison study of aroma compounds in hazelnuts both in raw and roasted form displayed that a great amount of volatiles were detected in roasted sample (71) that of in the raw sample (39), and both samples had considerable amounts of lipid-derived aldehydes, ketones, and alcohols (Alasalvar et al., 2003). Thermally derived compounds, including Strecker aldehydes and pyrazines, were detected abundantly in roasted hazelnut. Particularly, filbertone was determined at 10-fold greater amount in the roasted hazelnut in comparison with the raw one. The study directed by Pfnuer et al. (1999) revealed the occurrence of this compound not only in hazelnuts but also in their oils. Similarly in this study, oils obtained from roasted hazelnuts were reported to have at least 30 times higher amount of filbertone than that of the raw hazelnut oils. As the volatiles are significant indicators of the characteristic odor along with the quality in edible oils, there are a few studies investigating the hazelnut oil aroma (Caja et al., 2000; Kiefl et al., 2013; Kiralan & Kiralan, 2015; Matsui et al., 1998). The aroma of hazelnut oils comprises of diverse groups of volatiles with terpenes, aldehydes, alcohols, acids, furans, etc. This diversion depends on the geographical conditions, oil production techniques, the processes applied to oil before and after extraction like thermal treatments and refining and so on (Kiralan & Kiralan, 2015). For example, Bail et al. (2009) revealed that raw and roasted hazelnuts oils had a quite different volatile profile. According to the results, acetic acid and hexanal were common to both oil sample while compounds like 2-methylpyrazine, furfural, furfuryl alcohol, dimethyl pyrazine derivatives, 5-methylfurfural, and further pyrazine derivatives known to have effect on roasted notes were determined only in oils from roasted hazelnuts.

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31.3 Volatile composition and key odorants of hazelnut oil

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Another critical point affecting the aroma composition of hazelnut oils is the application of refining process. Refined hazelnut oil is produced by means of removal all of the unwanted substances in crude oil. Especially, in deodorization stage of refining process, because of high temperature is applied, volatile aldehydes, ketones, fatty alcohols, and sulfur compounds can be drastically diverged (Karabulut et al., 2005). The findings from a comparison study of volatiles in crude and refined hazelnut oils revealed the absence of several compounds in refined oil which are found originally in the crude oil like acetic acid, 1-hexanol, octanoic acid, etc. (Ogras et al., 2018). Additionally, after refining process the formation of furan compounds was reported in hazelnut oils. Enzymatic reactions (lipoxygenase [LOX] effect) and auto-oxidation have a critical role in the formation of volatiles in oils (Angerosa, 2002; da Silva et al., 2012). The volatile compounds formed by the chemical oxidation of oils are responsible for the undesirable taste and odor in oils, and this mechanism is defined as oxidative rancidity. On the other hand, enzymatic oxidation through LOX metabolic pathway, which has been mentioned in many studies, provides the desired aroma in oils. The LOX metabolic pathway begins with LOX enzyme activity and continues with the formation of 13-hydroperoxides from linoleic and linolenic acid (Calı´n-Sa´nchez et al., 2012; Haddada et al., 2007). The oxidation-induced volatile compounds detected in hazelnut oils were reported as 2-heptenal, nonanal, and (E,E)-2,4-decadienal (Kiralan & Kiralan, 2015). It was also implied in the same study that the formation of these compounds increases with the application of thermal treatments including microwave heating. Additionally, the difference of the cultivar has a great effect on the volatiles of oils. In previous studies comparing the hazelnut oil with other nut oils revealed that the volatile profile differed highly according to the raw material. For example, Kesen et al. (2018) compared Iranian nut oils such as almond, hazelnut, and walnut oils in terms of their volatile composition. According to the findings, it was reported that walnut oil was characterized with alcohols and furans; hazelnut oil with acids, lactones, pyrazines, and ketones; and finally almond oil with terpene and aldehydes. Benzaldehyde was the characterizing aldehyde in almond oils expectedly, while hexanal dominated the profile in hazelnut oils. γ-Caprolactone and γ-heptalactone in addition to the pyrazine derivatives were specific to hazelnut oils as they were not detected in other nut oils. Similarly, in other studies; furfural, (E)-5-methyl-hept-2-en-4-one, phenylacetaldehyde, sabinene, octanol, decanal, 2-acetyl pyrrole, and terpineol were reported to be found only in hazelnut oil between walnut, peanut, almond, and olive oils (Caja et al., ´ 2008). 2000; Mildner-Szkudlarz & Jelen, The precise and accurate analysis of aroma compounds is a complex procedure. The first step in the analysis of aroma compounds should be the selection of the most appropriate extraction method to be used for the isolation of these compounds to provide the most similar extract to the hazelnut oil sample. The selection and reliability of the extraction method is determined by sensory analysis using representative tests. In the second stage, the identification (GC-Ms) and quantification (GC-FID) of aroma compounds should be done using sensitive instrumental techniques (Ebeler et al., 2000; Selli et al., 2008). Additionally, the precise determination of these compounds is not enough in evaluating the unique odor of a food has. There are hundreds of aroma compounds in foods, very few of these have an effect in the creation of odor of that particular product. Aroma compounds responsible for the formation of the characteristic odor are called aroma-active compounds or key odorants and these are analyzed by the application of GC-Ms-Olfactometry (GC-Ms-O) technique.

Multiple Biological Activities of Unconventional Seed Oils

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31. Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil

GC-Ms-O analysis is the only technique that combines the precision and selectivity of the human nose with the separating power of gas chromatography. This method is used extensively to determine the aroma-active compounds among the volatile components in foods (Acree et al., 1984). Determination of aroma-active compounds is a very critical issue in aroma studies. GC-Ms-O technique is basically performed with three different methods. These include (1) the determination of the detection concentration of the aroma compounds (AEDA and CHARM techniques), (2) the determining the frequency of detection of the aroma compound, and (3) the expression of detection density of that particular compound. Among these methods, aroma extract dilution technique (AEDA) is the most commonly used technique in olfactometry analysis. The biggest advantage of AEDA is the low number of panelists performing the analysis compared to other methods (Ferreira et al., 2002). This technique is expressed by the flavor dilution (FD) factor. AEDA involves assessing an aroma extract by GC-Ms-O so as to detect all aroma-active compounds found in the extract and then continuing a set of serial dilutions until the aroma could not be detected. The volatiles persevering through the final dilutions are estimated as contributing to the odor of the food stuff. The method is applied by sniffing until the odor is not felt in GC-Ms-O analysis by diluting the aromatic extract step by step. The flavor compound with the highest FD value is expressed as the strongest aroma-active compound in that food (Grosch, 2001; Van Ruth, 2001). There are very few studies investigating the key odorants of hazelnut oils. The earliest study conducted by Matsui et al. (1998) identified the aroma-active compounds using AEDA and GC-Olfactometry techniques in hazelnut oils. A total of 28 aroma-active compounds were identified which nine of them showed FD factors of 1000 or higher. 2-ethyl3,5-dimethylpyrazine (roasty), 2,3-diethyl-5-methylpyrazine (roasty), vanillin (vanilla like), d-limonene (lemon like), hexanoic acid (sweaty), 2-methoxy-4-vinylphenol (spicy, phenolic), 3-methylbutanoic acid (sweaty), γ-octalactone (fruity, coconut-like), and (E)-5-methyl2-hepten-4-one (filbertone) (sweet, hazelnut like) were detected as the characterizing odorants in hazelnut oils (Fig. 31.1). Among these compounds, the most impressive odorant was reported to be the filbertone as it elicited the hazelnut-like odor. Eleven of the 26 FIGURE 31.1 Key odorants found in hazelnut oils (Matsui et al., 1998). (1) 2-Ethyl-3,5-dimethylpyrazine; (2) 2,3-Diethyl-5-methylpyrazine; (3) dLimonene; (4) Hexanal; (5) (E)-5-methyl-2-hepten4-one (filbertone); (6) γ-Octalactone.

Multiple Biological Activities of Unconventional Seed Oils

31.4 Phenolic composition of hazelnut oils

403

identified odorants have been already reported for roasted hazelnuts in other studies (Alasalvar et al., 2003, 2004; Caja et al., 2000). Pyrazine derivatives stand out in the oils obtained from roasted hazelnuts (Matsui et al., 1998). These compounds have a relatively low odor threshold allowing them to be sensed even at minor amounts. These compounds are generally formed as a result of Maillard reaction by prolysis of hydroxyamino acids and reduction of sugars (Mu¨ller & Rappert, 2010). 2-ethyl-3,5-dimethylpyrazine (roasty) and 2,3-diethyl-5-methylpyrazine (roasty) were the compounds found in abundance in hazelnut oils. In addition to pyrazines, aldehydes, with their low threshold values, are also important compounds in the formation of odor in both hazelnut and its oil. Hexanal and benzaldehyde were generally reported to have the highest FD factors among the aldehydes with green and almond like odor. Hexanal has been detected in the previous researches as both aroma and aromaactive compound hazelnut and its oil (Alasalvar et al., 2003; Burdack-Freitag & Schieberle, 2012; Kiefl et al., 2013; Matsui et al., 1998; Nicolotti et al., 2013). As mentioned above, the information detailing the composition of volatiles in hazelnut oils can be ascertained from existing literature. However, the key odorants of hazelnut oils have rarely been studied. Hence, further investigation of the aroma-active compounds and the effects of refining, extraction, and analysis parameters on these components should be carried out to have an enhanced information.

31.4 Phenolic composition of hazelnut oils Hazelnut, due to its phenolic composition, has a main role in nutrition and health. Phenolic compounds are secondary metabolites in plants and classified as phenolic acids and polyphenols. These compounds have at least one phenolic group or form as derivatives like an ester or methyl esters (Quideau et al., 2011). Among the phenolics; phenolic acids, flavonoids, and tannins are known as the major components of hazelnuts (Di Nunzio, 2019). Many studies reported a positive correlation between the phenolic compounds and the anti¨ zcan et al., 2018; oxidant activity of hazelnut and hazelnut oils (Alasalvar et al., 2009; O Shahidi et al., 2007). The antioxidant mechanism has a crucial part in reducing lipid oxidation process which can prevent the aging process, inflammation, some chronic diseases caused from oxidative stress in diet rich hazelnut and hazelnut oil (Kelebek et al., 2020). Hazelnut phenolics had a range between 491 and 1700 mg GAE/kg in kernels, 848
1149 mg GAE/kg in pellets, and only 0.14
0.25 mg GAE/g in oils. Several phenolic acids including gallic, caffeic, p-coumaric, ferulic, sinapic, caffeoyl tartaric, and caffeoylquinic acids were reported in hazelnuts (Amaral et al., 2005; Oliveira et al., 2008). Jakopic et al. (2011) investigated the phenolic compounds in hazelnut kernels. They found flavan-3-ols, benzoic acids, flavonols, and a phloretin glycoside in the samples. Al Juhaimi et al. (2018) 16 phenolics, including gallic, protocatechuic, catechin, caffeic, ferulic, sinapic, naringenin, chlorogenic, p-coumaric, rutin, resveratrol, vanillic, kampferol, quercetin, luteolin, and pinocembrin were determined in different cold pressed nut oils. Among these, protocatechuic acid (0,47 μg/100 g), catechin (0,89 μg/100 g), caffeic acid (0,67 μg/100 g), ferulic acid (0,38 μg/100 g), sinapic acid (0,42 μg/100 g), naringenin (1,13 μg/100 g), and luteolin (0,97 μg/100 g) were reported as the major compounds in hazelnut oils (Fig. 31.2).

Multiple Biological Activities of Unconventional Seed Oils

404

31. Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil

FIGURE 31.2 Phenolic compounds of nut oils obtained (μg/100 g) (Al Juhaimi et al., 2018). (1: Protocatechuic acid, 2: Catechin, 3: Chlorogenic acid, 4: Naringenin, 5: Caffeic acid, 6: Luteolin, 7: Sinapic acid).

In another study, four phenolics were determined in hazelnut oils. Their content ranged from 0.97 to 0.01 μg/g (Slatnar et al., 2014). Wu et al. (2004) also reported that one serving (28.4 g) of hazelnuts contains approximately 237 mg of total phenol content (in gallic acid equivalent) and 2739 mmol Trolox equivalent (ORAC method) of total antioxidant capacity. Interestingly, they noted that the main fraction responsible for antioxidant capacity was the hydrophilic fraction, not the lipophilic fraction (containing tocopherols). In another study, the total phenolic content of hazelnut oils reported between 0.1 and 0.2 mg GAE/g of oil (Slatnar et al., 2014). Similarly, Arranz et al. (2008) elucidated phenolics in hazelnut by UV-Vis spectrophotometry and determined as 0.08 mg GAE/g of oil. Kesen

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31.5 Antioxidant properties of hazelnut oil

TABLE 31.2

Main phenolic compounds of hazelnut oils by HPLC-DAD-ESI-Ms/MS.

Compound identity

λmax (nm)

[M-H]2(m/z)

Ms2 (m/z)

MRM transitions

Quantification (mg/kg)a Crude oil

Refined oil

Protocatechuic acid

294

153

137, 109

153 . 109

0.74 6 0.02

0.24 6 0.01

p-Hydroxybenzoic acid

415

138

223, 193

138 . 193

0.22 6 0.00

0.00 6 0.00

Caffeic acid

327

179

135

179 . 135

0.16 6 0.00

0.00 6 0.00

Vanillic acid

291

168

108

168 . 108

0.58 6 0.00

0.19 6 0.01

Ferulic acid

324

193

178, 149, 134

193 . 134

0.12 6 0.01

0.00 6 0.00

a

Quantification: Results were reported as the means of three repetitions as mg/kg.

et al. (2021) reported protocatechuic acid, p-hydroxybenzoic acid, caffeic acid, vanillic acid, and ferulic acid in hazelnut oil (Table 31.2). Among the determined compounds, protocatechuic acid and vanillic acid were reported as the most dominant compounds. When evaluated in general, it is notable that the amount of phenolic compounds in oils is low. This can be explained because of the refining in industrial-scale oil production. Refining has a diminishing effect in the bioactivity of hazelnut oil (Bhosle & Subramanian, 2005; Joki´c et al., 2016; Karabulut et al., 2005; Vaisali et al., 2015). During the neutralization treatment, oil is washed with water and this may have effects on the decreasing in the amounts of phenolics from oil (Pal et al., 2015). Soap formed could also contribute to this decrement in the oil (Durmaz & Go¨kmen, 2019). Additionally, the thermal procedure applied in deodorization can reason in the carotenoid degradation (Chew et al., 2016).

31.5 Antioxidant properties of hazelnut oil The continuous reaction between organic components and excessive molecular oxygen in the atmosphere results in several changes in biochemical structures of a food via formation of unstable harmful free radicals. Free radicals are known to be the waste substances causing the oxidation by disrupting the natural structure of biomolecules such as DNA, amino acids proteins, and lipids. There exist several internal and external factors in the formation or accumulation of free radicals in the body. Antioxidants are compounds that substantially postpone or inhibit the oxidation of oxidizable cells by scavenging the free radicals in the matrix. These compounds are in common use of food industry with the aim of the prevention of quality loss of a foodstuff and maintaining its nutritional value. Antioxidants are not only vital for the food and biochemistry sectors but also medicine as they provide protective effect to a cell itself against injuries caused by reactive oxygen species (Seifried et al., 2007). In light of this information, it is widely agreed that antioxidants are health-promoting substances neutralizing and inactivating the free radicals which are considered as important reasons of many human diseases. Their role in deterioration of living cells needs to be measured precisely to determine the oxidative damage that they cause (Halliwell & Whiteman, 2004).

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31. Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil

A large number of existing studies in the broader literature have examined the link between oxidative stress and several diseases, such as cardiovascular disorders, respiratory dysfunctions, cancer, mutagenesis, arthritis, DNA genesis, stroke, immune deficiency, Parkinson’s disease, and other vital anomalies (Saravia et al., 2013; Vaidya et al., 2020). In order to prevent these serious health problems, an antioxidant-rich diet is suggested. Fruits and vegetables are known to be rich sources of important antioxidants such as polyphenols, vitamin C, and carotenoids. These compounds are considered as the potential inhibitors of above-mentioned chronic diseases via scavenging the free radicals. Among antioxidant rich foods and crops, edible tree nuts and nut oils are considered as important source of various bioactive constituents. Nuts have long been an important part of Mediterranean diet and their frequent consumption has been proved to be an effective weapon against the risk of cardiovascular heart disease. The main reason of this health promoting effect of nut consumption is mostly associated with its cholesterol lowering property deriving from favorable lipid profile and naturally low-glycemic form of nuts. Apart from that, tree nuts are well-known natural antioxidant source due to their remarkable nutrients and phytochemicals. Among many important nutrients, vitamin E is the most abundant antioxidant component of nuts followed by selenium (Nora et al., 2020). Although there exist several studies based on the phenolic profiles and antioxidant capacities of dry nuts (Gentile et al., 2007), it is quite difficult to perform a comparative evaluation between their results due to changes in extraction methods (Chukwumah et al., 2007). Furthermore, there is a limited number of studies focused on the antioxidant activity of hulls of nuts and antioxidant potential of fresh nuts and their crude oil. However, nuts are mostly dried just after the harvest until they are processed or consumed since the drying prevents the microbial growth (Aktas & Polat, 2007). Besides, thermal processing of nuts, like drying or roasting, may also induce some enzymatic or nonenzymatic oxidative reactions that significantly changes their phenolic profile and antioxidant potential as well as their taste and aroma. On the other hand, a significant amount of nuts is also harvested as unripened and consumed freshly. Among nuts, walnut (the genus Juglans), cashew (Anacardium occidentale), and hazelnut (the genus Corylus) are considered as prominent nuts regarding their high antioxidant activity. Vinson and Cai (2012) investigated the antioxidant potential of several nuts including peanut, hazelnut, Brazil nut, macadamia, walnut, pistachio, pecan, cashew, and almond. According to results, researchers concluded that the walnut possessed the highest antioxidant capacity among other nuts followed by cashew and hazelnut. In another study Arranz et al. (2008) compared the antioxidant activity and oxidative stability of walnut, pistachio almond, hazelnut, and peanut oils. The authors found a correlation between antioxidant activity analyzed by DPPH procedure and oxidative stability in nut oils and tocopherols were reported to be effective for the oxidative stability in the samples. In most of the nuts, compounds that exhibit high antioxidant activity located in the skin and so dehulling of those nuts considerably decreases their antioxidant potential. Therefore, antioxidant potential of nuts should not only be considered as the nut itself, but also the skin, kernel, and other by-products (Chandrasekara & Shahidi, 2011). Hazelnut is rich in vitamin E, which is a kind of lipid soluble antioxidant. Oliveira et al. (2008) examined the antioxidant activity of three different hazelnut cultivar kernels,

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31.5 Antioxidant properties of hazelnut oil

407

Coutard, Bollwiller, and Daviana using different well-known methods, such as; lipid peroxidation inhibition, DPPH, β-carotene bleaching, and reducing power. According to results, cv. Daviana possessed greater amounts of phenolics that showed relatedly a better antioxidant activity on DPPH radical method. However, cv. Coutard showed the highest antioxidant activity in the inhibition of β-carotene bleaching. In another study, Shahidi et al. (2007) examined the antioxidant potential of hazelnut kernels and hazelnut products by means of total antioxidant activity, DPPH, hydrogen peroxide, and superoxide radical and β-carotene bleaching methods. Revealed results displayed that the kernel possessed the lowest total antioxidant concentration as 29 μmol of TE/g while hazelnut tree leaf exhibited the highest TA concentration having 148 μmol of TE/g in the ethanolic extract. Similarly, Alasalvar et al. (2009) carried out different experiments to determine antioxidant potential of fractional extracts of hazelnut skin. According to the results, researchers declared that the fraction high in tannins possessed the greatest activity in terms of antioxidants. Another remarkable by product is the hazelnut oil which is mainly characterized by its oleic acid rich structure providing it a high oxidative stability and nutritional value. Additionally, hazelnut oil was declared to have an important tocopherol and phytosterol content, particularly α-tocopherol and β-sitosterol (Alasalvar et al., 2003). Altun et al. (2013) studied the total oxidative stabilization of 15 different hazelnut cultivars by means of ABTS/persulfate, DPPH, and conventional CUPRAC methods. In general aspect, CUPRAC results were found to be twofold higher that ABTS/persulfate values due to possible inability of oxidation of lipophilic compounds in ABTS radical cation. The DPPH method showed that the percentage values were between 51% and 86% for oils and 42% and 59% for methanolic extracts. In another study, Durmaz and Go¨kmen (2019) evaluated the effect of refining on the antioxidant potential of hazelnut oil and methanolic extract by measuring their radical scavenging capacity. Researchers found that the bleaching and deodorization processes dramatically decreasing both the number of detected antioxidant compound and their concentrations and activity. Carotenoids are the main antioxidant compounds which undergo a significant degradation especially due to high temperatures applied in the oil processing. Similarly, Assumpc¸a˜o et al. (2014) mentioned that the zeaxanthin, lutein, and β-carotene were the main carotenoid compounds of grape seed oil and their concentrations were decreased significantly during oil processing. In another interesting study on hazelnut oil was carried out by ¨ zcanand Arslan (2011) in that they performed a comparative evaluation between some O spice essential oils (such as, cinnamon, rosemary, and clove) used for the oxidative stabilization of hazelnut oil. According to results of the study, researchers declared that the cinnamon essential oil was reported to have the highest affect among spice oils in oxidative stabilization of hazelnut oil. As a conclusion, although the crude hazelnut oil contains remarkable amounts of health-promoting antioxidants, its oxidative stability needs to be supported by the addition of some natural agents like essential oils of MAPs or spices. Besides, thermal processing of crude hazelnut oil for the industrial purposes, particularly; roasting, bleaching, and deodorization, decreases its important antioxidant potential, and so its added value.

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31. Biochemistry, antioxidant, and antimicrobial properties of hazelnut (Corylus avellana L.) oil

31.6 Antimicrobial activity of hazelnut oil Nut oils are known to be their remarkable potential as a good alternative to chemical synthetic antimicrobial agents for food preservation and their crucial role against a variety of microorganisms has been limitedly cited in the extant literature (Barta et al., 2020; Oliveira et al., 2008; Ramalhosa et al., 2011; Riahi et al., 2013). Fatty acid content and discrepancy, determines the antimicrobial effect and inhibition potential of nut oils (Kotmakc¸ı et al., 2015). As previously reported by some authors, the discrepancy of unsaturated fatty acids, particularly the linoleic and oleic acids, plays a substantial role to provide antimicrobial property to a nut oil (Dilika et al., 2000). In the same line with this information, Zheng et al. (2005) obtained a significant difference among individual fatty acids against microbial growth. The revealed data from this study showed that the palmitic acid has much less active in the inhibition of microbial growth when compared to oleic and linoleic acid in soybeans. Antimicrobial activity analysis comprises the inhibitory effect (MIC: minimal inhibitory concentration) of oil measured against a selected individual pathogenic strain and results given as the size of inhibition zone. Oliveira et al. (2008) determined the antimicrobial effect of several hazelnut cultivars against some gram positive (Staphylococcus aureus, Bacillus subtilis, and B. cereus) and gram negative (Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae) and fungi (Cryptococcus neoformans and Candida albicans). According to results, for all tested concentrations, researchers obtained that the hazelnut only showed a strong antimicrobial property against gram positive bacteria while had no significant effect against gram negative bacteria and fungi growth. Interestingly, in another study performed in order to obtain antimicrobial activities of hazelnut oil and husk extracts, researchers could not find any antimicrobial effect of American variety hazelnut oil, while the husk of the same nuts exhibited an important inhibition against almost 16 pathogenic strains, particularly on gram negative bacteria (Barta et al., 2020). It is thought that the main reason of the unexpected results for the hazelnut oil in antimicrobial analysis is caused by the varietal difference and detection limits of the used analyze method.

31.7 Conclusion It is evident that hazelnut oil consumption has a great potential for increase in the coming years worldwide. The fatty acid content, aroma, key odorants, phenolic composition, antioxidant characteristics, and antimicrobial activity of hazelnut oils were reviewed in current chapter. Hazelnut oil aroma is shown to be comprised of several volatile groups belonging various chemical classes and within these groups, aldehydes, alcohols, and furans are the highest contributors to the overall aroma. These findings are supported with GC-O methods that are used to determine the key odorants in oil samples. According to applied studies, key odorants including pyrazine derivatives with roasty odor notes, hexanal with green notes and d-limonene and α-pinene as terpenes with spicy and citrus

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References

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notes appear to participate to the characteristic aroma of hazelnut oils. Additionally, this oil is rich in phenolic compounds responsible for their its bioactive properties. The specific phenolics present in abundance in hazelnut oil are protocatechuic acid, catechin, caffeic acid, ferulic acid naringenin, and luteolin. The presence of these phenolics is also the reason for the high antioxidant capacity of the oil. Additionally, the antioxidative properties and antimicrobial activity of hazelnut oil were reviewed. The outcomes of this current study are to be thought as providing beneficial information regarding the aroma and phenolic composition and bioactive properties of hazelnut oils.

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234. Shahidi, F., Alasalvar, C., & Liyana-Pathirana, C. M. (2007). Antioxidant phytochemicals in hazelnut kernel (Corylus avellana L.) and hazelnut byproducts. Journal of Agricultural and Food Chemistry, 55(4), 1212
1220. Slatnar, A., Mikulic-Petkovsek, M., Stampar, F., Veberic, R., & Solar, A. (2014). HPLC-MS n identification and quantification of phenolic compounds in hazelnut kernels, oil and bagasse pellets. Food Research International, 64, 783
789. Solak, R., Turan, S., Kurhan, S., Erge, H. S., & Karabulut, I. (2018). Thermal oxidation kinetics of refined hazelnut oil. Journal of the American Oil Chemists’ Society, 95(4), 497
508. Turan, A. (2018). Effect of drying methods on fatty acid profile and oil oxidation of hazelnut oil during storage. European Food Research and Technology, 244(12), 2181
2190. Vaidya, F. U., Chhipa, A. S., Sagar, N., & Pathak, C. (2020). Oxidative stress and inflammation can fuel cancer. Role of oxidative stress in pathophysiology of diseases (pp. 229
258). Singapore: Springer. Vaisali, C., Charanyaa, S., Belur, P. D., & Regupathi, I. (2015). Refining of edible oils: A critical appraisal of current and potential technologies. International Journal of Food Science & Technology, 50(1), 13
23. Van Ruth, S. M. (2001). Methods for gas chromatography-ol factometry: A review. Biomolecular Engineering, 17 (4
5), 121
128. Vinson, J. A., & Cai, Y. (2012). Nuts, especially walnuts, have both antioxidant quantity and efficacy and exhibit significant potential health benefits. Food & Function, 3(2), 134
140. Wickland, S. E., Johnston, J. J., & Stone, M. B. (2001, June). Evaluation of roasted and natural hazelnut volatiles by purge-and-trap/gas chromatography/mass spectrometry. In Institute of Food Technologists Annual Meeting and Food Expo (pp. 23
27). Wu, X., Beecher, G. R., Holden, J. M., Haytowitz, D. B., Gebhardt, S. E., & Prior, R. L. (2004). Lipophilic and hydrophilic antioxidant capacities of common foods in the United States. Journal of agricultural and food chemistry, 52(12), 4026
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5162.

Multiple Biological Activities of Unconventional Seed Oils

C H A P T E R

32 Production process, methods of extraction, and refining technologies of unconventional seed oils Ramo´n Piloto-Rodrı´guez1 and Yosvany Dı´az-Domı´nguez2 1

Center for the Studies of Renewable Energies, Technical University of Havana, Havana, Cuba 2 Faculty of Chemical Engineering, Technical University of Havana, Havana, Cuba

32.1 Introduction Vegetable oils which are extracted from seed oils are considered one of the main components of our food and are also used for the production of alternative fuels (mainly biodiesel). Due to the food crisis in several regions, the huge demand of vegetable oils, and the growing production of biofuels, it becomes necessary to increase the world production but the seed oil sources. In this respect, several nonconventional seed oils are playing an active role (ElBassam, 2010). There are different agricultural crops that bring a significant production of conventional and unconventional seed oils. From them, several applications and industrial demands exist such as pharmaceutical and energy applications, among others. Four conventional vegetable oils are almost entirely covering the world market: soybean in USA, palm in Asia, canola, and sunflower oil. However, many underutilized seed oils, including those from Jatropha curcas and Moringa oleifera, are becoming more popular, contributing to meet the increasing demand for edible or nonedible oils in multiple applications (Boukandoul et al., 2018; Piloto-Rodrı´guez et al., 2020). Key issues arising from the exploitation of seed oils are: availability, oil content, extraction yield, quality, and purity of the oil. Seed oil yield depends on: oil seed variety and strain, soil, and environmental conditions as well as the technology, extraction method, and procedure. Unlike animal oils that are composed mainly by saturated fatty acids, vegetable oils (with few exceptions) have different proportions of saturated and unsaturated fatty acids (UFA) bonded to the triacylglycerol (TAG) molecule in a wide range. The

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physicochemical properties of TAG are strongly dependent on the nature of the bonded fatty acids that varied from oil to oil. Many developing nations are seeking new seed oil sources, through plants suitable in their climate and soil conditions, reducing the dependence on imported oils. There is also a search for novel oils with unique health properties and functional characteristics. The rising demand of vegetable oils both for human consumption and industrial applications has driven the evolution of routes for obtaining oil and the optimization of processes for a diverse but efficient production of vegetable oils (Demirbas, 2010). In this context, several nonconventional oil sources are under study, depending on availability, culture surrounding it, world region, and potential demand. Unconventional or special oils are vegetable oils used for a variety of purposes, such as flavoring food, health benefits, cosmetics, an bioenergy. Plants cultivation and harvesting, oil extraction and refining technologies are part of the life cycle of oil production for any application. In this respect, this chapter will bring an overview of all these subjects.

32.2 Production process The production process of unconventional oils is too wide to be analyzed in a limited number of pages. There are features that are common in at least all unconventional seed oils based on regular harvesting, and also compared to conventional oils. The activity is based on culture and harvesting of the seed and crushing seeds to extract the oil. Crops have become an important part of many arable rotation systems. This way, unconventional sources are becoming real alternatives to conventional ones in several ways (ElBassam, 2010; Sanjay, 2013). The key factors for oil seed production are: land availability, adequate weather and soil conditions (linked to the oil seed), water supply, and basic agroeconomy conditions for the development of the agroindustry, beside incentives for their production. Special attention must be paid to germination, growing, pesticides, availability of its specific water demand, and sunlight, besides harvesting season and cycles (ElBassam, 2010). Several sources of unconventional oils are the by-products of major agro industrial tasks, and then their production starts with the management of the by-products. For instance, rice bran oil is produced from the outer coating or bran of rice (Oryza sativa). It does not represent an attractive source of oil but more than 500 million tons of rice is produced worldwide each year (FAO, 2016). On the other side, are some nonconventional oils which are not coming from a by-product, but from a culture based on the production of the oil as a main target. Examples of it are J. curcas and M. oleifera (less frequent the target is oil production) (Martin et al., 2010). Since the oil is produced through cultivation of conventional or unconventional seeds, the harvesting, separation of seeds, and oil extraction are the next steps.

32.3 Methods of extraction Before extraction, oil seed pretreatment is necessary. The basic pretreatment steps are: dehulling (in many cases), seed coat removal (husk and shell), cleaning, milling, and preheating. Crushing of seeds before extraction is also important to ensure the brake of oil

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cells embedded in fibrous structures, enhancing the oil releasing. Heating is also an important step because it facilitates the oil release (Dı´az et al., 2021; Mwithiga & Moriasi, 2007; Takadas & Doker, 2017). Oil seed pretreatment before the oil extraction strongly influences yield and quality. Usually a preheating step is established. Traditionally it is developed by the use of hot air, but is being replaced by microwave-assisted heat treatment, and more recently by ultrasound assisted (Boukandoul et al., 2018; Piloto-Rodrı´guez et al., 2020). The particle size of solids, type of solvent for extraction and its volume, extraction temperature, and time are key factors of the oil extraction technology (Dı´az et al., 2021; Mwithiga & Moriasi, 2007; Takadas & Doker, 2017). Oil seeds must be cleaned of foreign matter before dehulling. The kernels are ground to reduce size and then cooked with steam, and the oil is extracted in a mechanical screw or hydraulic press. After sterilization, oil fruits are digested before mechanical pressing often in a screw. The pressed cake could be later used for extraction of the residual fat with solvents as n-hexane (Dı´az et al., 2021; Martin et al., 2010). There are three main methods for oil extraction despite the seed oil source. These are mechanical extraction (cold or hot pressing), wet extraction (steam or hot water extraction), and solvent extraction. With regard to the wet extraction method, up to nine operations that are involved in the extraction of oil by the old traditional methods are identified (Oluwole et al., 2015). These cover from the collection of seed up to the drying of the extracted oil by heating. The conventional oil extraction methods are the mechanical and solvent extraction. Nevertheless, it is quite often to use both in the same extraction task or a combination of conventional and nonconventional methods (Bokhari et al., 2015; Soto-Leon et al., 2014; Uquiche et al., 2008).

32.3.1 Solvent extraction of oil The solvent extraction method is often applied to oil seeds with low oil content (, 20%) (Sinha et al., 2015; Yusuf, 2017). It is one of the most efficient methods for vegetable oil extraction, with low residual oil in the cake or meal, but attention must be paid to the handling and recovery of the organic solvent. Regardless of solvent selection, a high solventsolute ratio, volatility of solvent to oil, oil viscosity and polarity, as well as cost are taking into account (Takadas & Doker, 2017). Its main advantage compared to mechanical extraction is the highest oil extraction yield, repeatability, and reproducibility of results. The drawbacks of the solvent extraction method are: long extraction times, high solvent consumption, higher energy requirements, safety concerns, emission of volatile organic compounds, high operational costs, possible decrease of product quality caused by high processing temperatures, and a relatively high number of processing steps (Takadas & Doker, 2017). Soxhlet extraction process is a primary way for extracting vegetable oils from oleaginous materials. The Soxhlet process is widely used at labscale, but large-scale operation requires a commercial solvent extractor (Ogunniyi, 2006). The major advantage of the Soxhlet process is solvent recycling during extraction (Yusuf, 2017) and relative high extraction yields. Seeds extracted by Soxhlet in different solvents are widely reported. The extraction with petroleum ether yields between 40% and 50% of oil from the seed (Lourith et al., 2014), with optimal conditions of the extractive to produce biodiesel for instance. Soxhlet extraction of the oil regularly implies the use of petroleum ether or n-hexane, being an

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effective way to extract the oil from the seed at laboratory scale; also in industrial practice n-hexane is used. Different extraction solvents and methods may vary the fatty acid composition of the oil and the extraction yield. Nevertheless when the oil content in relative fatty acids composition is important, for cosmetics or biological applications for instance, the extraction could be developed by compression, reflux, or maceration. A gathered sample of publications applying different extraction methods to unconventional seed oils is shown in Table 32.1. According to the information in Table 32.1, solvent extraction is widely reported for the extraction of many unconventional seed oils, regardless the long time for the process and the solvent-related problems. Solvent extraction is more often applied and reported for analytical purposes and at laboratory scale, but less used at industry, because of the restrictions in the use of chemicals in food industry mainly. This is not a concern for energy applications but is a main issue when the oil will be used in biological applications.

32.3.2 Mechanical extraction of oil Mechanical pressing is one of the easiest, ancient, and cheapest ways to extract oil from seeds and plant elements. Mechanical extraction involves the application of pressure (hydraulic or screw press) to force oil out. Mwithiga and Moriasi (2007) found that oil yield is linearly increased with compression pressure, duration of pressing, and increase in the temperature of preheated oil, reaching a peak yield at about 75 C. Nevertheless, the heating temperature is something to carefully adjust to avoid partial oil thermal decomposition in certain conditions and depending on oil thermal properties and its thermal degradation profile (Piloto-Rodriguez et al., 2012). With regard to oil yield, screw press has an advantage over hydraulic press. Mechanical press is very simple and ideal for laboratory work. It is quite popular in developing countries due to simplicity, achieving similar oil yields as other routes. At industrial scale, industrial machines or expellers are used for the purpose of extracting vegetable oils mechanically (Yusuf, 2017). There are two types of mechanical press methods: cold press and hot press. Cold press is carried out below 50 C. Oils prepared without the application of heat and in the absence of further processing are described as cold pressed. This method has the advantage of keeping oil flavor, depending on the quality of the seeds used as raw material, but relatively low oil yields are obtained and are therefore more expensive. Because the preserving of purity and natural properties of seed oils by this method, there is a growing global demand for cold-pressed oils. In contrast, hot-press methods bring higher oil yields due to decreased seed oil viscosity at high temperatures, enhancing oil flow. High temperature increases the efficiency of the extraction and yields of up to 80% of available oil (Patel et al., 2016), but it also increases oil degradation, reducing extracted oil quality. Conventional processing starts with a conditioning step by warming to 50 C
60 C. Seeds are then flaked to increase the surface area helping the release of oil, with a cooking step lasting 20
60 min, with temperatures up to 90 C
120 C. This step generates cell

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32.3 Methods of extraction

TABLE 32.1

Oil content and extraction methods applied to some unconventional seed oils.

Botanical name

Common name

Oil content (%)

Extraction method

solvent

Extraction time (h)

Yield (%)

References

Hevea brasiliensis

Para rubber

40
50

Reflux

n-hexane

9

20.84

Soxhlet

n-hexane

6

19.02

Lourith et al. (2014), Sanjay (2013)

Maceration

n-hexane

0.5

17.83

Cyperus esculentus

Yellow nutsedge

28

Soxhlet

n-hexane

6




Sidohounde et al. (2018)

Ceiba pentandra

Kapok tree

-

Soxhlet

n-hexane

2.5

25.95

Bokhari et al. (2015)

Carthamus tinctorius

Safflower

26
45

Soxhlet

n-hexane

2




ElBassam(2010), Nogala-Kalucka et al. (2010)

Moringa oleifera

Ben tree

31
48

Soxhlet

n-hexane

6

40
42 Boukandoul et al. (2018), Dı´az et al. (2021)

Nigella sativa

Black cumin

35
40

Soxhlet

n-hexane

0.5
2.5

39
44 Ma et al. (2019)

Jatropha cinerea




65.80

Soxhlet

n-hexane

6

57

Soto-Leon et al. (2014)

Carica papaya

Papaya seed

14
31

Soxhlet

n-hexane

10

25.27

Zhang et al. (2019)

Ultrasound




,1

32.27

Zhang et al. (2019)

Caesalpinia spinosa

Tara







petroleum ether

1

8

Li et al. (2016)

Capsicum annuum L.

Red pepper seed

18.39

Cold pressing







14.60

Soxhlet

n-hexane

6

18.39

Chouaibi et al. (2019)

Supercritical CO2 at 100 MPa, 0.40 L/min and 40 C




2

25.27

MAE at 1150 W and 2450 MHz

n-hexane

0.33

32.87

disruption causing oil droplets to merge and migrate across cell walls. As a result, the mechanical extraction by pressing that follows the cooking step removes 65%
70% of the oil contained in seeds (Anne-Gae¨lle et al., 2016). It lets to continue the cell wall disruption needed to obtain a high oil recovery in press cake ending with solvent extraction. Another traditional method for extraction of the oil involves boiling the peeled fruits in water with stirring. The collected oil is dried by heating and is filtered. This method is quite effective and suitable in rural areas in countries with no agro industrial development, because it is more artisanal than industrial, but it has the limitation of volume

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extracted. The traditional method of extraction is time and energy consuming, low in yield and quality but has several advantages.

32.3.3 Microwave-assisted extraction Microwave-assisted extraction (MAE) is used for extraction of seed and essential oils. A pretreatment of seed oil is done in a microwave oven, which uses radio waves to convey energy and convert it to heat at a frequency range of about 300
300 GHz (Singh & Heldman, 2001). The microwave radiation results in the rupture of cell membranes, increasing the extraction yield and mass transfer coefficients (Azadmard-Damirchi et al., 2011). Cellular membrane of oil seeds is the major barrier to oil extraction by pressing, which could be enhanced by microwave method, thus leading to improvement of oil extraction (Anne-Gae¨lle et al., 2016; Azadmard-Damirchi et al., 2011; Chouaibi et al., 2019; Mwithiga & Moriasi, 2007; Patel et al., 2016; Piloto-Rodriguez et al., 2012; Singh & Heldman, 2001; Uquiche et al., 2008). Moreno et al. (2003) report the use of MAE for oil extraction and found 97% of extraction by Soxhlet n-hexane extraction coupled to microwave pretreatment, compared with a single Soxhlet-hexane extraction (54%). Balasubramanian et al. (2010) found that microwave-pretreated oil has a higher composition of UFA, enhancing the oil quality. Advantages of MAE include: higher oil extraction yield and quality, lower energy consumption, faster processing time and reduction of the amount of solvent used, availability of phytosterols, tocopherols, carotenoids, and phenolic compounds in the extracted oil compared to cold-pressing or Soxhlet extraction. One disadvantage of MAE is that it may not be suitable for some plants, since high microwave energy disrupts the plant structure (Uquiche et al., 2008). MAE could degrade the polyunsaturated fatty acids, substantially varying the fatty acid profile. This could be negative when the oil will be used in biological applications. One problem associated with high temperatures during oil extraction is that they may enhance thermal decomposition processes, substantially varying oil composition and quality. However, despite claims that short exposure time to microwaves as compared to oven heating preserves most thermolabile compounds from degradation reactions (Amarni & Kadi, 2009).

32.3.4 Ultrasonic-assisted extraction Ultrasonic-assisted extraction (UAE) is based on the use of ultrasonic sound waves to increase vibration and heat, resulting in the destruction of plant cell walls and bonds, enhancing contact between the solvent and the lipids (Takadas & Doker, 2017). UAE application with solvent extraction is an effective route of increasing extracted oil yield (Yusuf, 2017). Samaram et al. (2014) analyzed oil production from papaya seeds by coupling both UAE and solvent extraction, and reported that while conventional solvent extraction lasted 12 hours, UAE method lasted only 30 minutes. Li et al. (2016) studied oil production from soybean by the UAE method, using n-hexane as extraction solvent, improving oil extraction efficiency and reducing the process time, which may have a significant impact on edible oil industry. The benefits of ultrasound assisted are attributed to acoustic cavitation: bubbles created in a liquid phase when applying ultrasound, which grow and oscillate

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419

quickly before collapsing due to pressure changes. These implosions disrupt the solid surface of the solid matrix, enhancing mass transfer and diffusion. Sicaire et al. (2016) reported a detailed study of the oil extraction on rapeseed applying ultrasounds, reporting an extraction yield over 30% after half an hour of ultrasounds. The use of ultrasound as cell disruptor can be also combined with the possibility of producing biodiesel (in case of a final energy use of the oil extracted) because it is a very efficient way to produce biodiesel by transesterification, instead of conventional stirring and heating, saving energy and time. Nevertheless, the experimental reaction conditions must be adjusted when ultrasounds are used to avoid over temperature and vaporization of reactants.

32.3.5 Supercritical fluid extraction This technique has as a main characteristic that since the solvating power of the fluid can be strongly influenced by small changes in pressure and temperature, it favors oil extraction and the precipitation of the solutes dissolved in the supercritical fluid (Rostagno & Prado, 2013). The technique is based on the use of a fluid at temperature and pressure beyond its critical point. At this critical thermodynamic stage, the significant change in its physical properties drastically changes its capacity as solvent. Among the solvents used in Supercritical fluid extraction (SFE), CO2 is the most used. The use of CO2 brings several advantages: it is inexpensive, environmentally friendly, and safe. Supercritical CO2 is attractive because of its high diffusivity and its solvent strength. Additional feature is that it makes recovery process simple and solvent-free extracts are obtained, being ideal for applications in food, pharmacy and cosmetic industries, with the possibility of working at low temperatures, allowing the extraction of thermally labile or easily oxidized compounds. It is known that supercritical CO2 extraction leads to extract more polar substances attributed to the action of lipolytic enzymes, resulting in higher free fatty acids (FFA) and peroxide values than using other methods (Soto-Leon et al., 2014). In fact it is well known that the FFA profile is influenced by the extraction method applied. By SFE, there is also a significant increase in the extraction of tocopherols, carotenoids, and total phenolic compounds compared to cold-pressing or Soxhlet extraction. Supercritical fluid technology brings significant improvements to the extraction of oil from natural sources. The application of it in oil industry can minimize wastewater compared to conventional mechanical extraction, and it is a cost-effective technique at laboratory and industrial scale (Akanda et al., 2012). The SFE is not only limited to the use of CO2;water, methanol, ethylene, ethane, n-butene, and n-pentane are also widely used (Pilar-Sanchez et al., 2014).

32.3.6 After extraction oil conditioning In large-scale production, oil seeds are dried to less than 10% of moisture. They may be stored for long time periods under adequate conditions of aeration. Such storage reduces mycotoxin and external contamination, minimizing biological degradation processes which

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increase FFA and color in the oil. Anyway the oil must be treated as quickly as possible. For long time storage, the application of a nitrogen atmosphere is suggested (Piloto-Rodriguez et al., 2012).

32.4 Refining process and related technologies Crude vegetable oil is mainly composed by TAGs and also contains numerous nonedible compounds that need to be removed by a refining process prior to human consumption. The purpose of refining is a maximum reduction of non-TAG, retaining the maximum amount of TAG, natural antioxidants, and vitamins, and to maintain or improve the organoleptic characteristics of the oil. The saving of antioxidants and vitamins is not applied to the case when the oil will be used for energy purposes, which is an important output for the production of conventional and unconventional seed oils. In the refining process, many organic compounds must be removed: FFA, phosphoacylglycerols, sterols, pigments, glucosides, waxes, hydrocarbons, glyceridic and nonglyceridic lipids. All these products affect oxidative stability of the oil and its flavor. The oil refining process has four main steps: degumming, deacidification (neutralization), bleaching, and deodorization. For the refining of crude vegetable oils, there are two main routes: the chemical and the physical refining. Some by-products of low commercial value are obtained through these refining processes. Important amounts of by-products such as soapstock, deodorizer fatty acid distillates, and acid oil are produced from the oil refining processes (Piloto-Rodriguez et al., 2014). Chemical refining is the most widely used technique to purify vegetable oils since it successfully decreases the level of FFA, phospholipids, waxes, aldehydes, and ketones among other components, but physical refining is also widely used. Physical refining has advantages since it reduces the loss of triglycerides, chemicals, and water consumption and enables the recovery of high quality FFA, reducing environmental impact. In the particular case of Malaysia for instance, more than 95% of the crude palm oil is refined through the physical route (Haslenda & Jamaludin, 2011). The physical refining uses steam instead of chemical neutralization. A general flow chart of the oil extraction and refining process following both physical and chemical routes is shown in Fig. 32.1. Physical refining or refining by bleaching and distillation phases follows the same steps as chemical refining except that there is no neutralization step. Chemical refining removes FFA by neutralization with NaOH and is developed under vacuum with steam injection. A detailed processes flow chart for chemical refining is shown in Fig. 32.2, and the corresponding physical refining is shown in Fig. 32.3. Chemical refining is more expensive that physical refining and some neutral TAGs are lost during the process. By physical refining, steam refining is the only method used in industry, and it is related to efficient degumming and bleaching. During the refining process, fatty substances can be structurally altered by different chemical reactions like hydrolysis, oxidation, dehydration, dimerization, polymerization, and esterification. The type of chemical reaction depends on the process used for the refining process (Piloto-Rodriguez et al., 2014). There are several compounds that are desirable to maintain in the oil after refining because they bring particular characteristics to the final

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421

FIGURE 32.1 Full processing flow chart for a general vegetable oil refining process.

product. Tocopherols protect the oil from oxidation, while sterols are inert, colorless, and stables to heat, so it is not necessary to separate them from the oil. The elimination of FFA in the oil is a main issue. FFA and some polar compounds can be easily removed by washing the oil with a solution of NaOH or Na2CO3. Phospholipids could be removed in this step together with FFA, but is more recommended and usually to separate in other step. In this case, a particular step of heating the oil in an aqueous solution of H3PO4 is often applied. The sediments (gums) are removed by centrifugation. The pigments are removed by bleaching with bleaching clay or charcoal, and the volatiles are removed by distillation with steam at high temperatures and under reduced pressure (deodorization). The resulting product is nearly colorless, flavorless, and with good storage stability (Piloto-Rodriguez et al., 2014).

32.4.1 Degumming The most important used degumming method is water degumming, which is the treatment of crude oil with hot water, and acid degumming, defined as treatment of crude oil with

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FIGURE 32.2 Stages and compounds eliminated by chemical refining.

FIGURE 32.3 Stages and compounds eliminated by physical refining.

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423

H3PO4 or citric acid (C6H8O7). It is relatively easy to remove hydratable phospholipids from crude oils since they absorb water and become insoluble in oil. Acid degumming process is preferred for processing rapeseed and sunflower oils (Cmolik & Pokorny, 2000). Water degumming is sufficient for the treatment of several types of vegetable oils, removing up to 99% of phospholipids by heating oil with water to 80 C
85 C and a further filtering. However, water degumming does not destroy nonhydratable salts of phosphatidic acids. The use of H3PO4 is particularly effective in the case of palm oil, but not for many other vegetable oils. In the case of degumming of soybean oil, the application of H3PO4 and water is recommended, first with concentrated acid and then with diluted acid. Citric acid is an alternative to H3PO4; it is more expensive than H3PO4 but the removal is more efficient. There are several types of degumming: water degumming, acidic degumming, dry degumming, enzymatic degumming, membrane degumming, and EDTA degumming. Therefore, the selection of a degumming method is depending on several factors such as available technologies, process cost, and characteristics of the oil to be processed but also the final quality. More recently, an enzymatic degumming has been developed and it represents a recommended route to degumming of oils which the quality but the chemical composition must be kept as the original one been suitable for biological applications. A process based on enzymes is very specific for the action they are selected, easy to neutralize their action, and inert to the main components of the oil. Also its environmental impact is quite lower than traditional methods.

32.4.2 Neutralization FFA can be easily removed by washing crude oil with a solution of NaOH or Na2CO3; the process is called alkali refining. The NaOH added to the oil is determined based on the percentage of FFA in the degummed oil. For physical refining, first an acid pretreatment with a dilute solution at 100 C is applied, followed by bleaching up to 2%
3% clay. Alkali refining works on nontriglyceride components except carotene and sulfur, but both are easily removed in the deodorization step. Alkali refining is the only step other than deodorization that removes FFA. Neutralization also eliminates soaps, phospholipids, metals, pigments, oxidation products, and some contaminants (Zio et al., 2020).

32.4.3 Bleaching Bleaching of edible fats and oils is developed between 90 C and 120 C. Around 0.2%
2% of bleaching earths are introduced and brought into contact for 30 min with stirring and under vacuum. The function of the bleaching earth is not only based on its adsorptive effect, but acts also as a solid acid, a cation exchanger and as a catalyst for several reactions. At this step, due to the relative low temperatures, only a small quantity of nonconjugated isomeric trans fatty acids is being formed. In the presence of an acidic bleaching earth, the formation of steradienes ethers is catalytically supported at temperatures below 100 C. The adsorbents could be activated carbon (from many sources) or naturally activated clays. The bleaching of oil is a fundamental step in refining (Baranowsky et al., 2001).

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32.4.4 Deodorization Deodorization is the last major processing step in the refining of edible oils. It is implemented to remove the undesirable ingredients in the oil, and those which may be conveyed by prior processes such as caustic refining, bleaching, hydrogenation, or even storage. Deodorization removes the volatile compounds, flavors, hydroperoxides, and some contaminants in the oil, in a process that takes place at 180 C
240 C. It is a process correlated with the reduction of FFA in the oil. Deodorization consists of steam-stripping the oil for FFA removal, depending on stripping steam rate, pressure, and temperature. The negative effects resulting of high temperatures during deodorization must be taken into account. The process can be developed at 240 C for 2 h or 270 C for 30 min. The degree of removal depends on the physical properties of the components: vapor pressure, temperature, and volume of steam passing through the oil. The removal of certain chemical compounds is quite important, for instance, the removal of off-flavors, pesticides and polycyclic aromatic hydrocarbons. Nevertheless, the undesirable loss of nutritional compounds (tocopherols and sterols) takes place during high temperature deodorization and physical refining, but the losses may be minimized if the processing conditions are optimized (Carvajal & Mozuraityle, 2019; Dijkstra & van Duijn, 2016; Snyder & Wilson, 2003).

32.4.5 Oil modification technologies Hydrogenation of edible oils and fats has been applied on a large scale where the unsaturation presented in the organic compound is reduced by reaction with hydrogen. The process is developed in a three-phase system at temperatures ranging from 120 C to 220 C; pseudo-first order reaction kinetics characterized the process. In it, not only reduction of double bounds takes place, but also isomerization. For this process, the catalyst is composed of nickel crystallites supported by an inorganic oxide, usually silica or alumina. The hydrogenation of oils is important because stabilizes the oil, improves flavor, and reduces oxidation (Dijkstra & van Duijn, 2016). There are two other important modification technologies. The first is interesterification, the rearrangement of the fatty acids in the triglyceride molecule under the influence of a moderately alkaline catalyst. It modifies the melting behavior of a fat without changing the nature of the fatty acids. The second is fractionation, which represents the controlled separation of oil/fat fractions at low temperature (dry fractionation) or solvents (solvent fractionation) without changing the chemical nature of the fatty acids (Dijkstra & van Duijn, 2016). There is also possible interrelationship of modification technologies. In industrial process, several oils of fats may be interchanged retaining product quality, where a combination of costs and quality is taken into account. Hydrogenation extends the number of fats available with specified melting behavior and this increases interchangeability and lowers the costs. In nonhydrogenation, a combination of interesterification, fractionation, and selection of the starting oil may be acceptable for limiting the formation of isomers; however, the costs are higher (Asif, 2011). The above-described steps, operational conditions, and the flow processes must be modified according to the oil to be processed but it will depend on the final use of the oil.

Multiple Biological Activities of Unconventional Seed Oils

32.5 Issues related to unconventional seed oil production for biological applications

425

For instance for the production of biodiesel from neat seed oil (unconventional or conventional), some steps could be avoided such as deodorization. If biodiesel production is fed with waste cooking oil, all the described chemical and physical steps certainly took place for the basic oil processing before human consumption. Nevertheless in this case some of them should be addressed again (Piloto, 2010). All processes and routes described in this section and in Figs. 32.1
32.3 are not depending on if the target is to process a unconventional oil or a conventional one, but adjust in processes and steps must be attended depending on the neat oil characteristics and chemical composition. This is why the section is presented in general terms for any vegetable oil. The above-described technologies are based on a vegetable oil which is conditioned for food, and not for medicinal or biological purposes.

32.5 Issues related to unconventional seed oil production for biological applications The huge genetic variability of the flora in our planet brings a phytochemical diversity, which is possible to use in a wide range of applications in health, nutrition, and cosmetics among others. In this respect, unconventional vegetable oils are a valuable feedstock. A vegetable oil is composed by triglycerides of fatty acids and glycerol, but the fatty acids profile defines the particularities of the oil (Bechkri et al., 2017). The accurate identification of this profile is important for assessment of oil quality but for identification of potential benefits and applications in health and cosmetics. There are two categories of vegetable oils as function of extraction and postextraction processes: refined oils as was previously described and virgin oils (Piloto, 2010). The virgin oils are only obtained by mechanical pressing or other physical devices and mainly using cold-pressing, under conditions which do not alter the composition. This extraction without any further refining keeps mostly intact the unsaponifiable fraction which lets to retain several bioactivities and potential benefits (Piloto, 2010). R. communis is nonedible oil grown extensively in tropical and subtropical regions. It produces a highly valued oil mainly composed by 80%
85% of ricinoleic acid which is used as raw material for the development of several industrial products: biolubricants, additives, coatings, surfactants, plastics, resins, waxes, soaps, drugs, and cosmetics. The reduction of its level of toxin is reported, spreading the biological applications. Researches have been developed for the obtaining of insect resistant or ricin-free genotypes (Villanueva-Mejia & Correa, 2017). Phytochemical compounds with bioactive properties (polyphenols, flavonoids, carotenoids, and phytosterols) are presented in many vegetable oils; these bioactive components are presented in virgin oils but during the refining process are eliminated. Similar to the restrictions to use solvent extraction when the oil will be used for food, its application in cosmetics or any biological activity constrains the use of this extraction technique in this context. One suggested extraction technique for oil that will be used in biological applications is the enzymatic. It is more simple and economic than traditional methods and techniques,

Multiple Biological Activities of Unconventional Seed Oils

426

32. Production process, methods of extraction, and refining technologies of unconventional seed oils

and due to the nonuse of solvents either high temperatures, the physical and chemical changes in the oil can increase the extraction yield but also avoid undesirable oxidation.

32.6 Rural vegetable oil production Rural oil extraction usually occurs near the areas where the raw material is produced or is available. This provides the small-scale farmers with access to raw materials, helping to reduce costs and processing time. For rural communities and low developed urban places, unrefined vegetable oils contribute significantly to the total amount of oil consumed. Crude oils are affordable to low-income groups and serve as important sources of carotenes and tocopherols. In this context, unconventional seed oils play an important role, providing a wide range of products locally generated and consumed, in many cases based on local traditions (ElBassam, 2010; Martin et al., 2010; Piloto, 2010; Piloto-Rodrı´guez et al., 2020). In many countries, traditional processes and technologies for producing oil are very important, especially among communities which have easy access to raw oleaginous materials. Traditional processing tends to be environmentally friendly but involves several people in the activities, which normally are relatives or neighbors and sometimes also are the final consumers. These advantages contrast with several negative issues related to traditional processing such as small production capacities, low industrial developed economies, low energy efficiency, and high time consumption for the full process, and the cost of transporting oils to markets (if is not in situ consumed). After harvesting, seed storage conditioning is an important issue that may affect further processes, the final oil quality, and its features. The moisture content of oil seeds strongly influences the quality of raw materials over time. In most rural operations, sun-drying reduces the moisture content of oil seeds to below 10%, as a very cheap way but not efficient due to the fluctuation of sunlight. Adequate aeration of the seed and other storage conditions of the seeds assure that moisture and microbial levels stay according to the needs. Shelling separates the oil-bearing portion of the raw material and eliminates the parts that have little or no nutritional value. Small-scale mechanical speller machines are available for kernels and nuts although manual cracking is still used. To increase the surface area and maximize oil yield the oil bearing is reduced in size. In oil extraction, the milled oil seed is mixed with hot water to make a paste until oil separation through an emulsion. For some oils, salt is usually added to coagulate the protein and enhance oil separation; it is well known that salts are good for decreasing the emulsion stability of many dispersed systems. For pressing, a plate or a piston is manually or mechanically activated, and the oil is collected below a perforated chamber. A variety of mechanical expellers can be finding in the market, mainly based on simple designs and accessible technologies. By boiling in basic devices, the traces of water in crude oil are removed after settling. This procedure is common in rural areas, by knowing the catalytic role of water in the development of rancidity and the reduction of oil quality. A by-product of the oil extraction is the pressed cake or seed cake. This by-product is generally useful in the agroindustry sector in several applications. Cake from extracted oil

Multiple Biological Activities of Unconventional Seed Oils

32.7 Transesterification for biodiesel production

427

is usually used as a source of nutrients. Nevertheless, it is suitable as biofertilizer and also can be used for combustion and for biogas and charcoal production. The cake contains proteins and carbohydrates, and depending on the unconventional oil treated, could be used as animal feed (Patel et al., 2016), mainly those obtained by mechanical oil extraction. Concerning the storage, transport, and packaging of the extracted oil, it must be protected against oxidative and thermal degradation, contamination with water, dirt, absorption of foreign odors, thermal deterioration, and foreign substances from packaging. Temperature, oxygen content, products generated by oxidation processes, trace metals content, enzymes, reduction in natural antioxidants, and the exposure to visible and ultraviolet light are key factors influencing oil deterioration. The use of low storage temperatures, nitrogen or vacuum packaging; the avoidance of copper, copper alloys, and iron as materials in containers, and the use of additives are elements helping to prevent deterioration of oil during storage.

32.7 Transesterification for biodiesel production The usefulness of vegetable oils as raw materials for biodiesel production is conditioned, among others to species and variety, oil/fat yield and energy efficiency. Several unconventional seed oils have been studied for biodiesel production (AmbrosewiczWalacik et al., 2017). The conversion of conventional and unconventional seed oils into a biofuel is well known and widely applied. The conversion of these oils to biodiesel passed through two basic reactions: esterification and transesterification. Most oil refining and biodiesel plants use the conventional NaOH/CH3ONa and/or H2SO4-based transesterification processes (Dı´az et al., 2021; Piloto, 2010). Esterification is applied when the FFA content in the oil is higher than 2%. After this process where the FFA are converted into methyl or ethyl esters, the transesterification is applied to reduce several chemical compounds in the oil that may affect engines performance and impact on parts, and basically converts the glycerides into methyl or ethyl esters and glycerol as a by-product. The critical parameter is to download the kinematic viscosity to the acceptable levels to fuel a diesel engine. This industry is based on the concept that the fuel (derived from seed oil) must be adapted to its use in diesel engines and not vice versa (ElBassam, 2010). Nevertheless, the oil may be direct used blended with diesel fuel or using preheating systems to reduce viscosity, but there is still a negative impact on the engine. The Elsbett engine is a variant of the diesel engine that lets the direct use of vegetable oils without transesterification. One of the key issues to be attended when seed oil is selected as feed for biodiesel production is its fatty acid profile (attached to the glycerides). The fatty acid composition and relative amounts are strongly related to the cetane number, a fundamental parameter of the combustion process (Piloto-Rodrı´guez et al., 2013). In this respect, any unconventional oil must be studied before selection, but in many cases they are more suitable than conventional ones based on chemical composition, not based on availability. The energy sector of biodiesel and its blends with diesel fuel is mainly based in bioenergy crops that produce conventional oils such as palm, soybean, sunflower, and

Multiple Biological Activities of Unconventional Seed Oils

428

32. Production process, methods of extraction, and refining technologies of unconventional seed oils

rapeseed. Nevertheless, the use of nonconventional seed oils to cover a growing demand of this sector at industrial scale or local (rural) scale is also based on unconventional seed oils as J. curcas, M. oleifera, neem, and R. communis among others (Martin et al., 2010; Pereira et al., 2015; Salaheldeen et al., 2014).

32.8 Conclusions The number of unconventional seed oils around the world is vast. The extraction, refining, and storage conditions are strongly related to the final use for this oil or its derivate. If the final use is the production of vegetable oil food quality, then the chemical or physical refining may be applied. An effective way to increase oil extraction yield is combining classic extraction processes with ultrasounds, supercritical, or microwave assisted. The use of the oil for health or biological purposes is conditioning the use of mechanical extraction alone or with supercritical fluid extraction with CO2 or any nonchemical process. In opposite, the use of the extracted oil for energy applications reduces the number of steps and oil requirements.

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47.

Multiple Biological Activities of Unconventional Seed Oils

Index Note: Page numbers followed by “f” and “t” refer to figures and tables, respectively.

A Allanblackia oil, biological activities of chemical compositions, 274
275 distribution of, 270f ethnobotany, 270
271 botanical description, 271, 271f, 272f vernacular names, 270
271 nutritional and chemical compositions, 272
275 Allelopathic activities of cucurbit seed oils, 122 Alzheimer’s disease (AD), 245
246 Angiotensin-converting enzyme (ACE), 245 Animal health, biological effects on, 310
311 Antiaging activity, 23
24 of Sclerocarya birrea kernel oil, 335
336 Anti-arthritic properties, of CPSO, 36
38 Antibacterial activity, 19 of evening primrose oil, 325 of fenugreek oil, 116 of Sclerocarya birrea kernel oil, 335 Anticancer activity, 22
23 of black cumin seed oil, 50 of black mahlab, 107 of evening primrose oil, 324 of Moringa seeds oil, 70
71 of niger seed oil, 85
86 Antidiabetic activity of black cumin seed oil, 47
48 of colocynth seed oil, 143
144 of evening primrose oil, 325
326 of pumpkin seed oil, 180 Antifertility properties, of CPSO, 36 Antifungal activity, 19 of fenugreek oil, 116 of Moringa seeds oil, 67
68 of niger seed oil, 85 Antihypercholesteremic properties, of black cumin seed oil, 45
47 Antihypercholesterolemic activity, of Cucumis melo L. seed oil, 132 Antihyperlipidemic properties, of black cumin seed oil, 45
47 Antihypertensive activity, 25
26

of black cumin seed oil, 47 Anti-inflammatory activity, 21
22 of black cumin seed oil, 49 of CPSO, 36
38 of Cucumis melo L. seed oil, 131 of cucurbit seed oils, 120
121 of evening primrose oil, 320
323, 321t of grape seed oil, 219
220 of niger seed oil, 86 of pistachio oil, 287 of pumpkin seed oil, 179
180 Antileishmanial activities, of pistachio oil, 287 Antimalarial activity, 24 of black mahlab, 106 Antimicrobial activity, 18
19, 408 of black mahlab, 104
105 of colocynth seed oil, 142
143 of Cucumis melo L. seed oil, 132 of cucurbit seed oils, 121
122 of grape seed oil, 222
223 of Moringa seeds oil, 65
67 of niger seed oil, 84
85, 85t of pumpkin seed oil, 178
179 of Roselle, 97
98 of watermelon seed oil, 191
193, 191f, 191t, 192f Antineuropathic activity, of evening primrose oil, 327 Antiobesity properties, of black cumin seed oil, 49 Antioxidant activity, 19
20, 405
407 of black cumin seed oil, 45 of black mahlab, 103
104 of citrus seeds fixed oil, 231
232, 232f of colocynth seed oil, 141
142 of CPSO, 36
38 of Cucumis melo L. seed oil, 130
131 of evening primrose oil, 323
324 of fenugreek oil, 115
116 of grape seed oil, 219
220 of Moringa seeds oil, 68
69 of niger seed oil, 86
88 of pistachio oil, 285
286, 286t of Sclerocarya birrea kernel oil, 335 Antiproliferative activity, 24

431

432

Index

Antiretroviral activity, of evening primrose oil, 327
328 Antitubercular activity, 20
21 of Moringa seeds oil, 69
70 Antitumor activity, 26 of evening primrose oil, 324 of grape seed oil, 220
222 Antiulcerogenic effects, 325 Anxiety and depressive-like behaviors, 287 Argan oil (AO), biological activities of animal health, biological effects on, 310
311 bioactive compounds contributing to, 311
313, 312t human health, biological effects on, 296
310 clinical evidences, 296
301, 297t preclinical studies and imminent developments of, 301
310, 302t safety and allergenicity, 313 Asian Pacific Coconut Community (APCC), 384, 388
390 Atopic eczema/dermatitis, 326
327

B Balanites aegyptiaca, 340
343, 340f Bioactive compounds, 355
356 Biodiesel production, transesterification for, 427
428 Biological activities, 17
18 types of, 18
26 antiaging, 23
24 antibacterial and antifungal activity, 19 anticancer activity, 22
23 antihypertensive activity, 25
26 anti-inflammatory activity, 21
22 antimalarial activity, 24 antimicrobial activity, 18
19 antioxidant activity, 19
20 antiproliferative activity, 24 antitubercular activity, 20
21 antitumor activity, 26 hypocholesterolemic activity, 25 hypoglycaemic activity, 25 Black cumin (Nigella sativa) seed oil biological activities of, 45
50 anticancer properties, 50 antidiabetic properties, 47
48 antihyperlipidemic and antihypercholesteremic properties, 45
47 antihypertensive properties, 47 anti-inflammatory properties, 49 antiobesity properties, 49 antioxidant properties, 45 potential toxicity of, 50 chemical composition, 44
45, 45t

C Carotenoids and chlorophyll, 355 Celastrus paniculatus seed oil (CPSO), 31f biological activities and therapeutic effects of, 33
39 antifertility properties, 36 antioxidant, anti-inflammatory and anti-arthritic properties, 36
38 cosmeceutical and wound healing properties, 38 gastroprotective properties, 38
39 neuroprotective properties, 34
36 botanical description, 30
31 chemical composition of, 31
33, 32t geographical distribution, 30
31 toxicological assessment of, 39 traditional medicinal uses of, 30
31 Chemical and compositional structures of, unconventional seed oils/biological activities Chrozophora tinctoria, 366
368 biological activity of seed oils, 367
368 fatty acid compositions, 366
367 tocopherol and sterols composition, 367 Cucurbita pepo, 374
376 biological activity of seed oils, 376 fatty acid composition, 374
375 sterols composition, 375
376 tocopherols, 375 Lallemantia spp, 376
377 fatty acid composition, 376
377 sterol composition, 377 tocopherols, 377 Nigella sativa, 371
374 biological activity of seed oil, 373
374 sterol composition, 372
373 tocopherols, 373 Pistacia spp, 368
371 biological activity of seed oils, 369
370 fatty acid composition, 369 sterol composition, 370
371 tocopherols, 371 Pyrus glabra and Pyrus syriaca, 364
366 biological activity of seed oils, 365
366 sterols, 366 tocopherol composition, 365 Chemical refining, 420 Chrozophora tinctoria, 366
368 Citrullus colocynthis seed oil biological activity, 141
144, 142t antidiabetic activity, 143
144 antimicrobial activity, 142
143 antioxidant activity, 141
142 plant and fruits, 140f pulp and seeds, 140f seed chemistry, 139
141

Index

Citrus seeds fixed oil biological activities of, 231
234 antioxidant activity, 231
232, 232f different biological activities, 233
234 composition of, 230
231, 230f Coconut oil biological activities of, 392
393 cholesterol profile of white rat, 393 weight development of white rats, 392
393, 393t composition of, 388
390 fatty acids composition, 388 micronutrient component, 388
390, 388t, 389t, 390t physico-chemical properties of, 387, 387t processing of, 385
387 dry process, 386
387 wet process, 385
386 varieties of coconut, 384
385 virgin coconut oil composition, 390
392, 391t lauric acid, 391
392 Cold-pressing technique, 3
4 Conjugated linoleic acid (CLA), 206 Cosmeceutical properties, of CPSO, 38 Crude vegetable oil, 420 Cucumis melo L. seed oil biological activities, 130
132 antihypercholesterolemic activity, 132 anti-inflammatory activity, 131 antimicrobial activity, 132 antioxidant activity, 130
131 botanical, morphology, and cultivation, 126
127 composition, 127
130 fatty acids, 127
128 phenolic compounds, 129
130 phytosterols, 128
129 vitamin E, 128 taxonomic classification of, 126t Cucumis melo var. cantaloupe antioxidant and pharmacological properties, 160
164 leaves, 161 peels, 162
163 pulp, 161
162 seeds, 163
164 botanical description, distribution, and cultivation regions of melon, 148
160 peels, 152
154 bioactive composition, 153
154 nutritional composition, 152 pulp, 150
152 bioactive composition, 150
152 nutritional composition, 150 seeds, 154
160

433

bioactive composition, 155 nutritional composition, 154
155 oils, 155
160, 156t, 157t, 158t, 159t Cucurbit seed oils allelopathic activities of, 122 anti-inflammatory activities of, 120
121 antimicrobial activity of, 121
122 Cucurbita pepo, 374
376

D Degumming method, 421
423, 422f Deodorization, 424 Direct Micro Expelling-Fluid Bed Dried (DME-FBD), 387 Direct Micro Expelling-Oven Dried (DME-OD), 386 Direct Micro Expelling-Sun Dry (DME-SD), 386 Dry process, 386
387

E Edible fats and oils, bleaching of, 423 Enzymatic procedure, extraction of oil using, 3
4 Ethnobotany, 270
271, 271f, 272f Evening primrose oil, biological activities of antibacterial activity, 325 anticancer and antitumor activity, 324 antidiabetic activity, 325
326 antiinflammatory activity, 320
323, 321t antineuropathic activity, 327 antioxidant activity, 323
324 antiretroviral activity, 327
328 antiulcerogenic effects, 325 atopic eczema/dermatitis, 326
327 hypocholesterolemic activity, 327 preventing and treatment of pain, 325 thrombolytic activity, 325 treatment for kidney disorders, 326 mastalgia, 319
320 rheumatoid arthritis, 318
319

F Factors affecting the quality of produced, unconventional seed oils agricultural factors, 347
348 bioactive compounds, 354
356 bioactive compounds, 355
356 phytosterols, 355 tocochromanols, 354 fatty acid composition, 352
354, 353t frying, 356
357 processing and handling of seed oils, 348
349 quality characteristics, 350
352, 351t seed oil storage conditions, 349
350

434 Fatty acid composition, 352
354, 353t, 388, 398
399, 399t Fenugreek (Trigonella foenum-graecum), 112f antibacterial and antifungal effect of oil, 116 antioxidant activity, 115
116 botanical description, 113 chemical composition, 113 different uses of, 113
114 seed composition, 114
115, 114f seed oil composition, 114f, 115 Fixed oils, 230 Free fatty acid (FFA), 346, 350
351, 419
421, 423
424, 427 Frying, 356
357

Index

volatile composition and key odorants, 400
403, 402f Hevea brasiliensis seeds, 254f Human health, biological effects on, 296
310, 297t, 302t Hypocholesterolemic activity, 25 of evening primrose oil, 327 Hypoglycaemic activity, 25

I Indonesian Coconut and Palmae Research Institute (ICOPRI), 384 Indonesian Palm Crops Research Institute (IPCRI), 387

K G Gama-Oryzanol/C40H58O4, 200 Gastroprotective properties, of CPSO, 38
39 Gram-negative and Gram-positive bacteria, 366, 373
374 Grape seed oil, different biological activities of antimicrobial activity, 222
223 antioxidant and anti-inflammatory activity, 219
220 antitumoral activity, 220
222 fatty acid composition, 217t potential biological activities of, 224 Grape seed proanthocyanidin extract (GSPE), 220 Guizotia abyssinica (niger) seed oil bioactivities of, 80
83 tocopherols in, 81, 81t total carotenoids, 82
83 total phenolics, 81
82 total sterols, 82 vitamin K1, 83 biological activities of, 84
88 anticancer activity, 85
86 antifungal activities, 85 anti-inflammatory activity, 86 antimicrobial activity, 84
85, 85t antioxidant activity, 86
88 chemical composition and properties of, 78, 79t effect of extraction solvent on bioactive composition and antioxidant activity, 83
84 fatty acid profile of, 78
80, 79t phytochemicals in, 80

H Hazelnut oils antimicrobial activity, 408 antioxidant properties, 405
407 fatty acid composition, 398
399, 399t phenolic composition, 403
405, 404f, 405t

Kidney disorders, treatment against, 326

L Lallemantia spp, 376
377 Lauric acid, 391
392

M Mastalgia, treatment of, 319
320 Mechanical press technology, 3
4 Mechanical pressing, 416
418, 417t Medium chain fatty acids (MCFAs), 384, 388, 390 Microwave-assisted extraction (MAE), 418 Monechma ciliatum (black mahlab), 101
102, 102f anticancer activity, 107 antimalarial activity, 106 antimicrobial activity, 104
105 antioxidant activity, 103
104 cosmetical uses of, 107 nutritional value and chemical composition of, 102
103, 103f uterotonic property of, 105
106 Monounsaturated fatty acids (MUFAs), 364
367, 369 Moringa seeds oil, 60
71 biological activities of, 64
71, 65t anticancer activity, 70
71 antifungal activity, 67
68 antimicrobial activity, 65
67 antioxidant activity, 68
69 antitubercular activity, 69
70 botanical descriptions and geographical distribution, 56
58, 58t cultivation for leaves and seed production, 58
59 fatty acid composition, 60
61, 60t, 61f oxidative stability, 62
63, 62t phytochemistry, 56, 57t seeds of Moringa species, 59
60, 59t sterol and tocopherol composition, 63, 64t

Index

N

Q

Neuroprotective properties, of CPSO, 34
36 Neutralization, 423 Nigella sativa, 371
374 Nonalcoholic fatty liver disease (NAFLD), 243 Nut oils, 408

Quality characteristics, 350
352, 351t

O Oil seed pretreatment, 414
415

P Pain, preventing and treatment of, 325 Pequi, 258
259, 259f, 265 bioactive compounds of, 260
261, 260f nutritional composition, 259
260 pulp oil, 261
265 biological activities of, 263
264 Phenolic composition, 403
405, 404f, 405t Phosphate fertilization, 347 Phytosterols, 32
33, 355 Pistachio oil, biological activities of antiinflammatory properties, 287 antileishmanial activities, 287 antioxidant capacity and oxidative stability, 285
286, 286t anxiety and depressive-like behaviors, 287 by-products, 288 chemical composition, 281
284, 282t plant description and distribution, 280
281, 280f safety concern, 289 scolicidal activity, 287 uses of, 284
285 Pistacia spp, 368
371 Polycystic ovary syndrome (PCOS), 287 Polyunsaturated fatty acids (PUFAs), 364
367, 369
370 Pumpkin seed oil antidiabetic property, 180 anti-inflammatory property, 179
180 antimicrobial property, 178
179 bioactive compounds, 176
178, 179t carotenoids, 177 phenolic compounds, 177 phytosterol and squalene, 177
178 tocopherols, 176 composition of, 175
178 fatty acid profile, 175
176, 175t macro and micronutrient composition, 173t production in different countries, 172t pumpkin botany, 172
174 Pyrus glabra and Pyrus syriaca, 364
366

435

R Radical scavenging activity (RSA), 373 Rheumatoid arthritis, treatment of, 318
319 Rice bran oil main bioactive compounds/biological activities bioactive phytochemicals, 200
201, 200f, 201f rice bran oil, 198
199, 199t rice bran, 197
198, 198f rice milling and by-products, 196
197, 197f role of bioactive components and activities, 201
208 anticancer aspects, 204
206, 205f, 207f antidiabetic properties, 207
208 antioxidant potential, 201
202 hypercholesterolemia, 202
204, 203f Roselle (Hibiscus sabdariffa L.) seed oil, 96 antibacterial activity of, 93f antimicrobial activity, 97
98 distribution, ecology, and cultivation, 93
94 fatty acid composition of, 92f important phytochemicals in, 93f microbiology of, 96
97 nutritional and phytochemical composition, 94
95 physicochemical characteristics, 96 proximate chemical composition of, 94t uses of, 95 Rubber seed oil, biological activities of, 254
255 Rural vegetable oil production, 426
427

S Sclerocarya birrea kernel oil, biological activities of marula oil uses and biological activities, 334
336 antiaging activity of, 335
336 antioxidant and antibacterial activity of, 335 protecting against environmental damage, role of, 336 Scolicidal activity, of pistachio oil, 287 Seed oil processing and handling of, 348
349 storage conditions, 349
350 Solvent extraction method, 3
4, 415
416 Squalene, 356 Stearic and palmitic acid (SFA), 364
365, 367, 369
370 Supercritical fluid extraction (SFE), 419

T Tea seed oil, biological activities of biological activities, 240
248 ameliorating hypercholesterolemia-induced ocular disorder, 242 exerting antihypertension effect, 245

436

Index

Tea seed oil, biological activities of (Continued) exerting bone-protective role, 246
247 exhibiting antioxidant and anti-inflammatory properties, 247 improving lipid profiles, 240
242, 241f improving physical performance and preventing fat accumulation, 242
243 mediating antimicrobial activity, 246 mediating hepatoprotective activity, 243
244 modulating gastrointestinal protective effect, 244
245 potential lactogenic effect, 248 serving as potential neuroprotective agent, 245
246 suppression of melanogenesis, 247 chemical composition, 238
240, 238t Thrombolytic activity, of evening primrose oil, 325 Tocochromanols, 354 Triacylglycerol (TAG), 420

U Ultrasonic-assisted extraction/ultrasound-assisted extraction (UAE), 218, 418
419 Unconventional seed oils biodiesel production, transesterification for, 427
428 biological applications, issues related to unconventional seed oil production for, 425
426 methods of extraction, 414
420 after extraction oil conditioning, 419
420 mechanical extraction of oil, 416
418, 417t microwave-assisted extraction, 418 solvent extraction of oil, 415
416 supercritical fluid extraction, 419 ultrasonic-assisted extraction, 418
419 oil production methods, 3
4 production methods and oil content, 2t

production process, 414 refining process and related technologies, 420
425, 421f, 422f bleaching, 423 degumming, 421
423, 422f deodorization, 424 neutralization, 423 oil modification technologies, 424
425 rural vegetable oil production, 426
427 unconventional oil worldwide, 4
6 utilization of, 6
10, 6f potential biodiesel fuels uses, 9
10 potential cosmetic uses, 8 potential food uses, 7
8 potential medicinal uses, 6
7 Unsaturated fatty acids (UFAs), 364
367, 369
370, 418

V Virgin coconut oil (VCO), 384
385, 387
393, 393t composition, 390
392, 391t Volatile composition and key odorants, of hazelnut oil, 400
403, 402f

W Water degumming, 423 Watermelon (Citrullus lanatus) seed oil antimicrobial activity, 191
193, 191f, 191t, 192f fatty acids content, 187
188, 188t general phytochemical screening of, 189
190, 189t minerals content, 187 pharmacological properties of, 190f proximate chemical composition of, 187, 187t significance of medicinal plants, 186
187 Wet process, 385
386 Wheat germ oil, 354 Wound healing properties, of CPSO, 38