Applications of Natural Products in Food [1 ed.] 9781616683702, 9781608769988

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Copyright © 2010. Nova Science Publishers, Incorporated. All rights reserved. Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan, Nova

Copyright © 2010. Nova Science Publishers, Incorporated. All rights reserved. Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan, Nova

FOOD SCIENCE AND TECHNOLOGY

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APPLICATIONS OF NATURAL PRODUCTS IN FOOD

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Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

FOOD SCIENCE AND TECHNOLOGY

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APPLICATIONS OF NATURAL PRODUCTS IN FOOD

SUPAYANG PIYAWAN VORAVUTHIKUNCHAI AND

WUMI IFESAN

Nova Science Publishers, Inc. New York

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

Copyright © 2011 by Nova Science Publishers, Inc. All rights reserved. No part of this book may be reproduced, stored in a retrieval system or transmitted in any form or by any means: electronic, electrostatic, magnetic, tape, mechanical photocopying, recording or otherwise without the written permission of the Publisher. For permission to use material from this book please contact us: Telephone 631-231-7269; Fax 631-231-8175 Web Site: http://www.novapublishers.com NOTICE TO THE READER The Publisher has taken reasonable care in the preparation of this book, but makes no expressed or implied warranty of any kind and assumes no responsibility for any errors or omissions. No liability is assumed for incidental or consequential damages in connection with or arising out of information contained in this book. The Publisher shall not be liable for any special, consequential, or exemplary damages resulting, in whole or in part, from the readers’ use of, or reliance upon, this material.

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Independent verification should be sought for any data, advice or recommendations contained in this book. In addition, no responsibility is assumed by the publisher for any injury and/or damage to persons or property arising from any methods, products, instructions, ideas or otherwise contained in this publication. This publication is designed to provide accurate and authoritative information with regard to the subject matter covered herein. It is sold with the clear understanding that the Publisher is not engaged in rendering legal or any other professional services. If legal or any other expert assistance is required, the services of a competent person should be sought. FROM A DECLARATION OF PARTICIPANTS JOINTLY ADOPTED BY A COMMITTEE OF THE AMERICAN BAR ASSOCIATION AND A COMMITTEE OF PUBLISHERS.

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Library of Congress Cataloging-in-Publication Data Applications of natural products in food / editors, Supayang Piyawan Voravuthikunchai and Wumi Ifesan. p. cm. Includes index. ISBN H%RRN 1. Food additives. 2. Natural products. I. Voravuthikunchai, Supayang Piyawan. II. Ifesan, Wumi. TX553.A3A67 2009 641.3'08--dc22 2010002975

Published by Nova Science Publishers, Inc. © New York

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

CONTENTS

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Preface

vii

Chapter 1

Introduction

Chapter 2

Herbs and Spices Commonly-Used in Foods

11

Chapter 3

Bioactive Compounds from Plants

29

Chapter 4

Common Foodborne Pathogens

39

Chapter 5

Natural Products as Antioxidants in Foods

73

Chapter 6

Antibacterial Activity of Natural Additives in Foods

95

Chapter 7

Incorporation of Natural Additives into Flexible Films

129

Chapter 8

Combination of Natural Additives with Other Preservatives or Preservation Methods

133

Chapter 9

Organoleptic Assessments of Natural Additives

143

Chapter 10

Future Work and Conclusions

147

Index

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

1

151

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PREFACE

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This book is focused on new researches pertaining to the following areas: herbs and spices commonly-used in foods, bioactive compounds derived from plants with specific focus on applications of natural products as antibacterial agents and antioxidants in foods. The data recorded through ethnopharmacological field studies are invaluable as these provide information on medicinal plants used to treat foodborne diseases. Pharmacognostic studies on certain plants have been included which provides basic data to help fixing-up their pharmacopoeial standards, thereby ensuring quality food additives. Other interesting topics include reviews on proposed mechanisms of actions of natural products as well as applications in the food industry.

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

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Chapter 1

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INTRODUCTION A variety of microorganisms may cause food spoilage or food poisoning which is major concerns for food industries. Use of chemicals to enhance food safety has been of great interest. Chemical preservatives vary in their effectiveness in eliminating microorganisms depending on the types as well as physical and chemical characteristics of foods (Cherry, 1999). Most commonly-used chemical preservatives include weak acids or their salts or esters such as lactic acid, citric acid, acetic acid, sodium benzoate, potassium sorbate, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and tertiary-butyl hydroquinone (TBHQ). However, consumers have grown serious awareness on health risks associated with the use of these chemicals. Concerns over the safety of some chemical preservatives and negative consumers’ reaction to these preservatives they perceive as chemical and artificial, have prompted an increased interest in natural alternatives. Moreover, the use of chemical-based antimicrobials in the treatment of many infectious diseases had inevitably resulted in multiple-drug or chemical resistance in both animal and plant pathogens (Davis, 1994). Although the antimicrobial properties of herbs and spices have been long recognized, recent researches in naturally-derived antimicrobials have led to a renewed scientific interest in these substances. A possible alternative to synthetic antimicrobials is the use of plants and their products, together with the essential oils which are thought to be generally effective for food safety and preservation (Lanciotti et al., 2004). Western society appears to be experiencing a trend of ‘green’ consumerism (Smid and Gorris, 1999), desiring fewer synthetic food additives and products with a less impact on the environment. Furthermore, the use of natural preservatives to improve the shelf life of meat products is a promising technology as many herbs, spices,

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

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Supayang Piyawan Voravuthikunchai and Wumi Ifesan

and their essential oils have demonstrated both antioxidant (Rey et al., 2005; Bañón et al., 2007; Carpenter et al., 2007; Jayathilakan et al., 2007; Juntachote et al., 2007; Ifesan et al., 2009d) and antimicrobial properties (Ahn et al., 2004; Gutierrez et al., 2008; Solomakos et al., 2008; Ifesan et al., 2009d). It is estimated that there are 250,000 to 500,000 species of plants on Earth (Borris, 1996), while about 1 to 10% of these have been used as foods by humans and other animal species. Plants have an almost limitless ability to synthesize aromatic substances, most of which are phenols or their oxygensubstituted derivatives (Geissman, 1963). Populations consuming diets rich in fruits and vegetables have shown to have lower incidences of many oxidationlinked chronic diseases such as cancer, cardiovascular diseases, and diabetes. This has led to a recent surge in interest in the use of diet as a potential tool to manage oxidation-linked diseases. Phenolic phytochemicals with antioxidant properties are now believed to be an important component in fruits and vegetables responsible for these beneficial health effects (Vattem, 2004). The substances serve as plant defense mechanisms against predation by microorganisms, insects, and herbivores. These include compounds such as terpenoids, which give plants their odours, quinones and tannins which are responsible for plant pigments. More importantly, a wide range of herbs and spices used by humans to season food yield useful medicinal compounds. ‘Herb’ is a plant grown for medicinal value or for flavouring food. On the other hand, Food and Drug Administration (FDA) stated a definition for ‘spice’ as an aromatic vegetable substance in the whole, broken, or ground form, the significant function of which in food is seasoning rather than nutrition and from which no portion of any volatile oil or other flavouring principle has been removed (FDA, 1980). Some plants are considered to be both herb and spice as there are no clear distinctions between them in most of the scientific literatures. Many spices are herbal products and their essential oils extracts have been reported. The essential oils and terpenoid alcohols of spices contribute to their taste and tactile sensation. Menthol, from mint, has a cooling effect as well as characteristic fresh taste (Shelef, 1983; Aktug and Karapinar, 1986; Arora and Kaur, 1999; Delgado et al., 2004; Nassar-Abbas and Hakman, 2004). Cardamom, cloves, oregano, and some other spices and herbs contain eugenol of which is fragrant and aromatic. Ginger contains gingerols, zingiberene, and other characteristic agents that make it an important flavour in Asiatic and Arabic herbal traditions (Kovacs et al., 2004). Naturally-sourced substances are becoming more widely used in the food industry both as flavouring and tenderizing agents (Sinku et al., 2003; Rajkovic et al., 2005; Rey et al., 2005; Garg and Mendiratta, 2006;

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

Introduction

3

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Jayathilakan et al., 2007; Naveena et al., 2008; Ifesan et al., 2009c, 2009d). In addition, antimicrobial properties of a number of medicinal plants have been extensively reported (Murakami et al., 1994; Murakami et al., 1995; Voravuthikunchai et al., 2002; Alzoreky and Nakahara, 2003; Voravuthikunchai and Kitpipit, 2003; Voravuthikunchai et al., 2004a, 2004b, 2004c; Siripongvutikorn et al., 2005; Voravuthikunchai and Kitpipit, 2005; Voravuthikunchai et al., 2005a, 2005b, 2005c; Oonmetta-aree et al., 2006; Valero and Frances, 2006; Voravuthikunchai and Limsuwan, 2006; Voravuthikunchai et al., 2006a, 2006b, 2006c, 2006d, 2006e; Voravuthikunchai, 2007; Voravuthikunchai et al., 2007; Limsuwan and Voravuthikunchai, 2008; Saising et al., 2008; Voravuthikunchai and Mitchell, 2008; Voravuthikunchai and Suwalak, 2008; Voravuthikunchai et al., 2008a, 2008b, Del Nobile et al., 2009; Ifesan and Voravuthikunchai, 2009; Ifesan et al., 2009a, 2009b, 2009c, 2009d, 2009e; Limsuwan and Voravuthikunchai, 2009; Voravuthikunchai and Suwalak, 2009; Voravuthikunchai et al., 2009). However, selection of a natural antimicrobial should be based on the sensory and chemical compatibility of the antimicrobial with the food, its stability considering the type of primary preservative system used, and the safety of the consumers.

REFERENCES Ahn, J., Grun, I.U. and Mustapha, A. 2004. Antimicrobial and antioxidant activities of natural extracts in vitro and in ground beef. J. Food Prot. 67: 148-155. Aktug, S.E. and Karapinar, M. 1986. Sensitivity of some common food poisoning bacteria to thyme, mint and bay leaves. Int. J. Food Microbiol. 3: 349-354. Alzoreky, N.S. and Nakahara, K. 2003. Antimicrobial activity of extracts from some edible plants commonly consumed in Asia. Int. J. Food Microbiol. 80: 223-230. Arora, D.S. and Kaur, J. 1999. Antimicrobial activity of spices. Int. J. Antimicrob. Ag. 12: 257-262. Bañón, S., Diaz, P., Rodriguez, M., Garrido, M.D. and Price, A. 2007. Ascorbate, green tea and grape seed extracts increase the shelf life of low sulphite beef patties. Meat Sci. 77: 626-633. Borris, R.P. 1996. Natural products research: perspectives from a major pharmaceutical company. J. Ethnopharmacol. 51: 29-38.

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Carpenter, R., O’Grady, M.N., O’Collaghan, Y.C., O’Brien, J.P. and Kerry, J.P. 2007. Evaluation of the antioxidant potential of grape seed and bearberry extracts in raw and cooked pork. Meat Sci. 76: 604-610. Cherry, J.P. 1999. Improving the safety of fresh produce with antimicrobials. Food Technol. 53: 54-59. Davis, J. 1994. Inactivation of antibiotics and the dissemination of resistance genes. Science 264: 375-382. Delgado, B., Palop, A., Fernado, P.S. and Periago, P.M. 2004. Combined effect of thymol and cymene to control the growth of Bacillus cereus vegetative cells. Eur. Food Res. Technol. 216: 188-193. Del Nobile, M.A., Di Benedetto, N. Suriano, N. Conte, A., Lamacchia, C., Corbo, M.R. and Sinigaglia, M. 2009. Use of natural compounds to improve the microbial stability of amaranth-based homemade fresh pasta. Food Microbiol. 26: 151-156. Food and Drug Administration. 1980. Chapter 5: Foods, colors and cosmetics, sub chapter 525: condiment industry. Compliance policy guide. . Garg, V. and Mendiratta, S.K. 2006. Studies on tenderization and preparation of enrobed pork chunks in microwave oven. Meat Sci. 74: 718-726. Geissman, T.A. 1963. Flavonoid compounds, tannins, lignins and related compounds. In: Florkin, M. and Stotz, E.H. eds., Comprehensive Biochemistry, Vol. 9. Pyrrole Pigments, Isoprenoid Compounds and Phenolic Plant Constituents. Elsevier, New York, p. 265. Gutierrez, J., Barry-Ryan, C. and Bourke, P. 2008. The antimicrobial efficacy of plant essential oil combinations and interactions with food ingredients. Int. J. Food Microbiol. 124: 91-97. Ifesan, B.O.T. and Voravuthikunchai S.P. 2009. Effect of Eleutherine americana Merr. extract on enzymatic activity and enterotoxin production of Staphylococcus aureus in broth and cooked pork. Foodborne Pathog. Dis. 6: 699-704. Ifesan, B.O.T., Hamtasin, C., Mahabusarakam, W. and Voravuthikunchai, S.P. 2009a. Inhibitory effect of Eleutherine americana Merr. extract on Staphylococcus aureus isolated from food. J. Food Sci. 74: M31-M36. Ifesan, B.O.T., Hamtasin, C., Mahabusarakam, W. and Voravuthikunchai, S.P. 2009b. Assessment of antistaphylococcal activity of semi-purified fractions and pure compounds from Eleutherine americana. J. Food Prot. 72: 354-359.

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

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Introduction

5

Ifesan, B.O.T., Siripongvutikorn, S. and Voravuthikunchai, S.P. 2009c. Application of Eleutherine americana crude extract in homemade salad dressing. J. Food Prot. 72: 650-655. Ifesan, B.O.T., Siripongvutikorn, S., Hutadilok-Towatana, N. and Voravuthikunchai, S.P. 2009d. Evaluation of the ability of Eleutherine americana crude extract as natural food additive in cooked pork. J. Food Sci. 74: M352-M357. Ifesan, B.O.T, Siripongvutikorn, S., Thummaratwasik, P. and Kantachote, D. 2009e. Stability of antibacterial property of Thai green curry during chilled storage. J. Food Process. Preserv. 34: 308-321. Jayathilakan, K., Sharma, G.K., Radhakrishna, K. and Bawa, A.S. 2007. Antioxidant potential of synthetic and natural antioxidants and its effect on warmed-over-flavour in different species of meat. Food Chem. 105: 908-916. Juntachote, T., Berghofer, E., Siebenhandl, S. and Bauer, F. 2007. The effect of dried galangal powder and its ethanolic extracts on oxidative stability in cooked ground pork. LWT 40: 324-330. Kovacs, Gy., Kuzovkina, N., Szoke, E. and Kursinszki, L. 2004. HPLC determination of flavonoids in hairy-root cultures of Scutellaria baicalensis Georgi. Chromatographia 60 (Suppl. 1): S81-S85. Lanciotti, R., Gianotti, A., Patrignani, F., Belletti, N., Guerzoni, M.E. and Gardini, F. 2004. Use of natural aroma compounds to improve shelf life and safety of minimally processed fruits. Trends Food Sci. Tech. 15: 201208. Limsuwan, S. and Voravuthikunchai, S.P. 2008. Boesenbergia pandurata (Roxb.) Schltr., Eleutherine americana Merr. and Rhodomyrtus tomentosa (Aiton) Hassk. as antibiofilm producing and antiquorum sensing in Streptococcus pyogenes. FEMS Immunol. Med. Microbiol. 53: 429-436. Limsuwan, S. and Voravuthikunchai, S.P. 2009. Medicinal plants with significant activity against important pathogenic bacteria. Pharm. Biol. 47: 683-689. Murakami, A., Kondo, A., Nakamura, Y., Ohighasi, H. and Koshimizu, K. 1995. Glyceroglycolipids from citrus hystrix, a traditional herb in Thailand, potently inhibit the tumor-promoting activity of O-12tetradecanoylphorbol 13-acetate in mouse skin. J. Agric. Food Chem. 43: 2779-2783.

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Supayang Piyawan Voravuthikunchai and Wumi Ifesan

Murakami, A., Ohigashi, H. and Koshimizu, K. 1994. Possible anti-tumor promoting properties of edible Thai food items and some of their constituents. Asia Pac. J. Clin. Nutr. 3: 185-191. Nassar-Abbas, S.M. and Hakman, K.A. 2004. Antimicrobial effect of water extract of sumac (Rhus coriaris L.) on growth of some food-borne bacteria. Int. J. Food Microbiol. 97: 63-69. Naveena, B.M., Sen, A.R., Vaithiyanathan, S., Babji, Y. and Kondaiah, N. 2008. Comparative efficacy of pomegranate juice, pomegranate rind powder extract and BHT as antioxidants in cooked chicken patties. Meat Sci. 80: 1304-1308. Oonmetta-aree, J., Suzuki, T., Gasaluck, P. and Eumkeb, G. 2006. Antimicrobial properties of action of galangal (Alpinia galanga Linn.) on Staphylococcus aureus. LWT 39: 1214-1220. Rajkovic, A., Uyttendaele, M., Courtens, T. and Debevere, J. 2005. Antimicrobial effect of nisin and carvacrol and competition between Bacillus cereus and Bacillus circulans in vacuum-packed potato puree. Food Microbiol. 22: 189-197. Rey, A.I., Hopia, A., Kivikari, R. and Kahkonen, M. 2005. Use of natural food/plant extracts: cloudberry (Rubus Chamaemorus), beetroot (Beta Vulgaris “Vulgaris”) or willow herb (Epilobium angustifolium) to reduce lipid oxidation of cooked pork patties. LWT 38: 363-370. Saising J., Hiranrat A., Mahabusarakum, Ongsakul M. and Voravuthikunchai S.P. 2008. Rhodomyrtone from Rhodomyrtus tomentosa (Ait.) Hassk as an antibiotic for staphylococcal infections. J. Health Sci. 54: 589-595. Shelef, L.A. 1983. Antimicrobial effects of spices. J. Food Safety 6: 29-44. Sinku, R.P., Prasad, R.L., Pal, A.K. and Jadhao, S.B. 2003. Effect of plant proteolytic enzymes on physico-chemical properties and lipid profile of meat from culled, desi and broiler chicken. Asian-Aust. J. Anim. Sci. 16: 884-888. Siripongvutikorn, S., Thummaratwasik, P. and Huang, Y. 2005. Antimicrobial and antioxidant effects of Thai seasoning, Tom-Yum. LWT 38: 347-352. Smid, E.J. and Gorris, L.G.M. 1999. Natural antimicrobial for food preservation. In: Rahman, M.S. ed., Handbook of Food Preservation, CRC Press, New York, pp. 285-308. Solomakos, N., Govaris, A., Koidis, P. and Botsoglou, N. 2008. The antimicrobial effect of thyme essential oil, nisin, and their combination against Listeria monocytogenes in minced beef during refrigerated storage. Food Microbiol. 25: 120-127.

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Introduction

7

Valero, M. and Frances, E. 2006. Synergistic bactericidal effect of carvacrol, cinnamaldehyde or thymol and refrigeration to inhibit Bacillus cereus in carrot broth. Food Microbiol. 23: 68-73. Vattem, D.A. 2004. Phenolic antioxidants from plants and mechanism of action through redox metabolism. Bioactivities of Phytochemicals: Health Promotion, Human Nutrition and Food Supply II. The 56th Southeast Regional Meeting, Nov. 10-13, 2004. Texas State University, San Marcos. Voravuthikunchai, S.P. 2007. Family Zingiberaceae compounds as functional antimicrobials, antioxidants, and antiradicals. Food 1: 227-240. Voravuthikunchai, S.P. and Kitpipit, L. 2003. Activities of crude extracts of Thai medicinal plants on methicillin-resistant Staphylococcus aureus. 9 (Suppl. 1): 236. Voravuthikunchai, S.P. and Kitpipit, L. 2005. Effective medicinal plant extract against hospital strains of methicillin-resistant Staphylococcus aureus. Clin. Microbiol. Infec. 11: 510-512. Voravuthikunchai, S.P. and Limsuwan, S. 2006. Medicinal plant extracts as anti-Escherichia coli O157:H7 agents and their effects on bacterial cell aggregation. J. Food Prot. 69: 2336-2341. Voravuthikunchai, S.P. and Mitchell, H. 2008. Inhibitory and killing activities of medicinal plants against multiple antibiotic-resistant strains of Helicobacter pylori. J. Health Sci. 54: 81-88. Voravuthikunchai, S.P. and Suwalak, S. 2008. Antibacterial activities of semipurified fractions of Quercus infectoria against enterohemorrhagic Escherichia coli O157:H7 and its Verocytotoxin production. J. Food Prot. 71: 1223-1227. Voravuthikunchai, S.P. and Suwalak, S. 2009. Changes in cell surface properties of Shiga toxigenic Escherichia coli by Quercus infectoria G. Olivier. J. Food Prot. 72: 1699-1704. Voravuthikunchai, S.P., Lortheeranuwat, A., Ninprom, T., Popaya, W., Pongpaichit, S. and Supawita, T. 2002. Antibacterial activity of Thai medicinal plants against enterohaemorrhagic Escherichia coli O157:H7. Clin. Microbiol. Infec. 8 (Suppl. 1): 116-117. Voravuthikunchai, S.P., Brusentsev, S., O’Rouke, J. and Mitchell, H. 2004a. Efficacy of crude extracts of Thai medicinal plants on antibiotic-resistance Helicobacter pylori strains isolated from peptic ulcers. Clin. Microbiol. Infec. 10 (Suppl. 1): 334. Voravuthikunchai, S.P., Popaya, V. and Supawita, T. 2004b. Antibacterial activity of crude extracts of medicinal plants used in Thailand against pathogenic bacteria. Ethnopharmacologia 33: 60-70.

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Voravuthikunchai, S.P., Lortheeranuwat, A., Jeeju, W., Sririrak, T., Phongpaichit, S. and Supawita, T. 2004c. Effective medicinal plants against enterohaemorrhagic Escherichia coli O157: H7. J. Ethnopharmacol. 94: 49-54. Voravuthikunchai, S.P., Limsuwan, S. and Wanmanee, S. 2005a. The investigation of antimicrobial plant extracts against Escherichia coli strains. Clin. Microbiol. Infec. 11 (Suppl. 2): 525-534. Voravuthikunchai, S.P., Phongpaichit, S. and Subhadhirasakul, S. 2005b. Evaluation of antibacterial activities of medicinal plants widely used among AIDS patients in Thailand. Pharm. Biol. 43: 701-706. Voravuthikunchai, S.P., Sirirak, T., Limsuwan, S., Iida, T. and Honda, T. 2005c. Inhibitory effect of active compounds from Punica granatum on Verocytotoxin production by enterohaemorrhagic Escherichia coli. J. Health Sci. 51: 590-596. Voravuthikunchai, S.P., Chusri, S. and Kleiner, P. 2006b. Inhibitory activity and killing activity of extracts from the gall of Quercus infectoria against methicillin-resistant Staphylococcus aureus. Clin. Microbiol. Infec. 12 (Suppl. 4): R1885-R2270. Voravuthikunchai, S.P., Limsuwan, S. and Mitchell, H. 2006c. Effects of Punica granatum pericarps and Quercus infectoria nuthgalls on cell surface hydrophobicity and cell survival of Helicobacter pylori. J. Health Sci. 52: 154-159. Voravuthikunchai, S.P., Suwalak, S. and Supawita, T. 2006d. Antibacterial activity of fractions of Quercus infectoria (nut galls) against enterohaemorrhagic Escherichia coli. Clin. Microbiol. Infec. 12 (Suppl. 4): 679-940. Voravuthikunchai, S.P., Limsuwan, S., Supapol, O. and Subhadhirasakul, S. 2006e. Antibacterial activity of extracts from family Zingiberaceae against foodborne pathogens. J. Food Safety 26: 325-334. Voravuthikunchai, S.P., Bilasoi, S. and Supamala, A. 2006a. Antagonistic activity against pathogenic bacteria by human vaginal lactobacilli. Anaerobe 12: 221-226. Voravuthikunchai, S.P., Limsuwan, S. and Subhadhirasakul, S. 2007. Screening for medicinal plants with broad spectrum of antibacterial activity. Inter. J. Antimicrobial. Agents 29 (Suppl. 2): S599. Voravuthikunchai, S.P., Ifesan B.O.T., Mahabusarakam W. and Hamtasin C. 2008a. Antistaphylococcal activity of semi-purified fractions from Eleutherine americana. Clin. Microbiol. Infec. 14 (Suppl. 7): 580.

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Introduction

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Voravuthikunchai, S.P., Chusri, S. and Suwalak, S. 2008b. Quercus infectoria Oliv. Pharm. Biol. 46: 367-372. Voravuthikunchai, S.P., Kanchanapoom, T. and Sawangjaroen, N. 2009. Antibacterial, anti-giardial, and antioxidant activities of Walsura robusta. Nat. Prod. Res. doi:10.1080/1478641092819152.

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

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Chapter 2

HERBS AND SPICES COMMONLY-USED IN FOODS Many herbs and spices used to preserve and improve the flavour of foods may additionally play a role in increasing the appetite of the consumers. Bioactive components studies have revealed that the active compounds found in herbs and spices usually present in a wide range of plants (Table 1).

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Table 1. Culinary herbs and spices commonly employed in food and their bioactive components Herb/spice Allspice (Pimenta officinalis Lindl.) Basil (Ocimum basilcum L.)

Black pepper (Cymbopogon citratus (DC.) Stapf) Caraway (Carum carvi L.) Cardamom (Elettaria cardamomum (L.) Maton)

Bioactive components eugenol anthocyanins, apigenin, carvacrol, catechin, 1,8-cineole, cintronellol, p-coumaric acid, eugenol, farnesol, geraniol, kaempherol, limonene, menthol, methyl cinnamate, quercetin, rosmarinic acid, rutin, safrole, β-sitosterol, tannin, α-terpinene, ursolic acid limonene, α-pinene, β-pinene, piperidine, piperine carvone, kaempferol, limonene, α-pinene caffeic acid, limonene

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Table 1. (Continued) Herb/spice Cinnamon (Cinnamomum zeylanicum Blume) Cloves (Syzygium aromaticum (L.) Merr. & L.M. Perry) Coriander (Coriandrum sativum L.)

Bioactive components cinnamic aldehyde, eugenol, 2-hydroxycinnamaldehyde eugenol, gallic acid, isoeugenol

Cumin (Cuminum cyminum L.)

caffeic acid, β-carotene, carvacrol, carveol, carvone, 1,8-cineole, coumaric acid, cuminaldehyde, p-cymene, geranial, kaempferol, limonene, α-pinene, β-pinene, p-quercetin, β-sitosterol, tannin, γ-terpinene, thymol carvone, catechin, isorhamnetin, kaempferol, limonene, myricetin, quercetin allicin, allyl isothiocyanate, diallyl disulfide

Dill (Anethum graveolens L.) Garlic (Allium sativum L.) Ginger (Zingiber officinale Roscoe) Green tea (Camellia sinensis (L.) Kuntze)

borneol, caffeic acid, β-carotene, 1,8-cineole, cinnamic acid, p-coumaric acid, p-cymene, ferrulic acid, geraniol, kaempferol, limonene, myrcene, β-pinene, quercetin, rutin, β-sitosterol, α-terpinene, vanillic acid

curcumin, ingerol, paradol, shagoal, zingiberene, zingiberone (+)-catechin, (−)-epigallocatechin, (−)-epigallocatechin gallate, gallic acid, theanine, theophylline farnesol, geraniol

Lemongrass (Cymbopogon citratus (DC.) Stapf) Marjoram apigenin, carvacrol, 1,8-cineole, p-cymene, (Origanum majorana L.) eugenol, farnesol, geraniol, limonene, α-pinene, rosmarinic acid, sterols, α-terpinene, thymol, ursolic acid Mustard allyl isothiocyanate, β-carotene (Brassica juncea (L.) Czern.) Nutmeg caffeic acid, catechin (Myristica fragrans Houtt.) Onion dipropyl disulfide, quercetin (Allium sepa L.) Oregano apigenin, caffeic acid, carvacrol, p-coumaric acid, (Origanum vulgare L.) luteolin, myricetin, quercetin, rosmarinic acid, thymol Paprika or red pepper ascorbic acid, capsaicin, β-carotene, (Capsicum annuum L.) dihydrocapsaicin, lutein, α-tocopherol, vitamin E

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

Herbs and Spices Commonly-Used in Foods Peppermint (Mentha X piperita L.) Rosemary (Rosmarinus officinalis L.)

Sage (Salvia officinalis L.)

Thyme (Thymus vulgaris L.)

13

apigenin, eriodictyol, hesperitin, limonene, luteolin, menthol apigenin, caffeic acid, carnasol, carnosic acid, β-carotene, cineole, geraniol, limonene, luteolin, naringin, α-pinene, rosmarinic acid, rosmanol, vanillic acid apigenin, caffeic acid, carnosic acid, β-carotene, catechin, cineole, citral, eugenol, farnesol, ferulic acid, gallic acid, geraniol, limonene, luteolin, perillyl alcohol, α-pinene, rosemarinic acid, saponin, β-sitosterol, thymol, ursolic acid, vanillic acid apigenin, caffeic acid, carnosic acid, β-carotene, carvacrol, cineole, cismaritin, eugenol, gallic acid, hispidulin, limonene, luteolin, α-pinene, rosmarinic acid, thymol, ursolic acid curcumin, curcuminoids

Turmeric (Curcuma longa L.) Modified from Kaefer and Milner, 2008

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GALANGAL (Alpinia galanga (L.) Willd.), GINGER (Zingiber officinale Roscoe), AND TUMERIC (Curcuma longa L.) The rhizomes of the Zingiberaceae family are widely used as spices in many Asian countries. Their medicinal functions have been broadly discussed and accepted in a number of traditional recipes. Zingiberaceae plants contain many essential oil including alcohols, carotenoids, flavonoids, ketones, phytoestrogens, and terpenes (Habsah et al., 2000; Mau et al., 2003; Suhaj, 2006). Both antimicrobial (Mau et al., 2003, Oonmetta-aree et al., 2006; Voravuthikunchai et al., 2006; Mayachiew and Devahastin, 2007; Voravuthikunchai, 2007) and antioxidant (Mayachiew and Devahastin, 2007; Voravuthikunchai, 2007; Chen et al., 2008) properties of Zingiberaceae plants have been well-documented.

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Supayang Piyawan Voravuthikunchai and Wumi Ifesan

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Figure 1. Galangal (Alpinia galanga (L.) Willd).

Galangal, a member of the ginger family, is native to Southern China and Thailand. The rhizome is a hot, sweet, spicy aromatic root-stock like ginger with slightly sour and peppery notes. Galangal rhizome is primarily used as a flavouring agent, especially in the preparation of fresh Thai curry paste (Ifesan et al., 2009) and tom-yum soup (Siripongvutikorn et al., 2005). It has been demonstrated that essential oils from both fresh and dried rhizomes of galangal have antimicrobial activities against pathogenic bacteria (Oonmetta-aree et al., 2006; Voravuthikunchai et al., 2006), fungi, yeast, and parasite (Farnsworth and Bunyapraphatsara, 1992; Yang and Eilerman, 1999). Two phenolic compounds, p-hydroxycinnamaldehyde and di-(p-hydroxycis-styryl) methane (Barik et al., 1987) and 1’-acetoxychavicol acetate (Voravuthikunchai et al., 2005) were isolated from the chloroform extract of the rhizomes of Alpinia galanga. Jitoe et al. (1992) reported potent antioxidant activity of curcuminoids isolated from Alpinia galanga. Essential oils from the rhizomes of galangal comprising of camphene, camphor, 1,8-cineole, β-elemene, fenchyl acetate, guaiol, α-pinene, β-pinene, and α-terpineol were reported (Raina et al., 2002).

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Figure 2. Ginger (Zingiber officinale Roscoe).

Ginger has been used as spice for over 2,000 years (Bartley and Jacobs, 2000). The water extract of ginger exhibits 6-gingerol and its derivatives which is mostly found in the rhizome at concentrations of 130 to 7,138 ppm. It possesses high antioxidant activity (Chen et al., 1986). Furthermore, ginger has been shown to contain gingerol-related compounds and diarylheptanoids as the main antioxidant fraction (Nakatani, 2003). Ginger is known for its contribution to food, antioxidant (Nakatani, 2000; Voravuthikunchai, 2007), as well as antimicrobial activities (Martins et al., 2001; Wang and Ng, 2005; Voravuthikunchai et al., 2006; Voravuthikunchai, 2007). Leaves of ginger plants have also been used for food flavouring and in traditional medicine. As folk medicine, rhizomes of ginger plants are consumed by women during ailment, illness, and confinement (Chan et al., 2008). In addition to its aromatic contribution to foods, ginger tea has been used to improve circulation, aid digestion, and treat nausea from motion sickness, pregnancy or chemotherapy (Ernst and Pittler, 2000).

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Supayang Piyawan Voravuthikunchai and Wumi Ifesan

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Figure 3. Turmeric (Curcuma longa L).

Turmeric has been widely used as an orange-yellow colouring agent. It was found to be a rich source of phenolic compounds and curcuminoids (Govindarajan, 1980). Extracts from turmeric econtain curcumin, demethoxycurcumin, bis-demethoxycurcumin, and three different diarylheptanoids. Commercially available curcumin consists of a mixture of three naturally occurring curcuminoids with approximately 77% curcumin (Ahsan et al., 1999). Curcumin may be present at concentrations as high as 38,000 ppm in certain species (Suhaj, 2006). It has been shown to possess a wide range of therapeutic effects and employed as natural food preservative and as dye (Reddy and Lokesh, 1992). Turmeric in powdered form has been in continuous use for its flavouring, as a spice in both vegetarian and nonvegetarian food preparations and it also demonstrates digestive properties (Govindarajan, 1980). Applications of turmeric in canned beverages, baked products, ice cream, biscuits, sauces, sweets, and yoghurts are common worldwide.

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Herbs and Spices Commonly-Used in Foods

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GARLIC (Allium sativum L.) AND ONION (Allium cepa L.) The Allium family is composed of over 500 members, each different in appearance, colour, and taste but similar in biochemical, phytochemical, and nutraceutical properties. The Allium family although comprised principally of water, the most medically significant components are organosulfur-containing compounds (Benkeblia, 2004; Lanzotti, 2006). Garlic and onion are most commonly utilized ingredients as flavour enhancers for several foods. Both exhibited a number of biological activities including antibacterial, antiviral, antifungal, antiprotozoal, and anticancer as the result of the presence of sulfur, phenolic, and selenium compounds (Fleischauer and Arab, 2001; Sallam et al., 2004; Arnault and Auger, 2006; Tang and Cronin, 2007). They have been demonstrated to possess antimicrobial (Benkeblia, 2004) and antioxidant (Harber et al., 1995; Dwivedi et al., 1996; Aguirrezabal et al., 2000; Yeh and Liu, 2001; Fista et al., 2004; Iqbal and Bhanger, 2007) effects. Garlic contains nearly three times as much sulfur-containing compounds as onions, about 11 to 35 milligram per 100 gram of fresh weight (Lawson, 1996) whereas onion contains higher amount of flavonol compounds than garlic (Lanzotti, 2006). In addition, the quercetin (1,497 milligram per kilogram) in onion, which has been shown to protect low-density lipoprotein cholesterol from oxidation and to reduce the risk of cardiovascular diseases, demonstrates the most profound difference as compared to that (47 milligram per kilogram) in garlic (Lanzotti, 2006). Between 1970 and 2005, the United States Department of Agriculture (USDA) Economic Research Service (ERS), reported that garlic usage in the United States has increased more than six-fold (USDA/ERS, 2007). During maceration of garlic, enzyme allinase acts on precursor allin to form allicin which is responsible for the flavour of fresh garlic. Consequently, allicin undergoes non-enzymatic degradation to form methyl and allyl mono-, di-, and tri-sulphides (Lawson and Hughes, 1992).

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Supayang Piyawan Voravuthikunchai and Wumi Ifesan

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Figure 4. Garlic (Allium sativum L).

Figure 5. Onion (Allium cepa L.).

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Herbs and Spices Commonly-Used in Foods

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OREGANO (Origanum vulgare L.)

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Figure 6. Oregano (Origanum vulgare L).

The essential oil of oregano, in particular, which is obtained by a steamdistillation process of leaves and flowers of Origanum vulgare subsp. hirtum plants, is a very promising dietary supplement since it exhibits substantial antioxidant as well as antimicrobial activity in vitro (Sivropoulou et al., 1996; Skandamis and Nychas, 2001). Sahin et al. (2004) reported that the essential oil of Origanum vulgare subsp. vulgare can be used as natural preservatives in food against well-known causal agents of foodborne diseases and food spoilage such as Escherichia coli, Enterobacter spp., Bacillus spp., Salmonella spp., Staphylococcus aureus, Candida spp., Fusarium spp., Aspergillus spp., Rhizopus spp., and Penicillium spp. Several recent studies have shown that incorporation of the essential oils of oregano in chicken, turkey, and rabbit diets improved the oxidative stability of raw and cooked muscle tissues during refrigerated and long-term frozen storage (Botsoglou et al., 2002; Botsoglou et al., 2003; Botsoglou et al., 2004; Govaris et al., 2004). The antimicrobial (Dorman and Deans, 2000; Aligiannis et al., 2001; Dmetzos et al., 2001; Tabanca et al., 2001) and antifungal (Daferera et al., 2000; Sokovic et al., 2002; Daferera et al., 2003) abilities as well as the use of oregano as a traditional remedy to treat various ailments such as a digestive disorders, menstrual problems, whooping and convulsive coughs (Ryman, 1992) have been established.

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Supayang Piyawan Voravuthikunchai and Wumi Ifesan

ROSEMARY (Rosmarinus officinalis L.)

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Figure 7. Rosemary (Rosmarinus officinalis L).

One of the most important sources of natural antioxidants is rosemary from the Lamiaceae family. Many studies have been carried out to examine the antioxidant activities of crude rosemary and its purified compounds. The antioxidant efficiency of rosemary extracts is due to high content of phenolic compounds including flavonols, phenols, phenolic acids (rosmarinic acid), monoterpenes, diterpenes, and triterpene acids (Leung and Foster, 1996; Bauman et al., 1999). The effectiveness of rosemary extract in lowering lipid oxidation in various foods with high sensory scores have been documented (Stoick et al., 1991; Shahidi and Wanasundara, 1992; Huisman et al., 1994; SanchezEscalante et al., 2001; Yu et al., 2002; Estevez et al., 2005). Rosemary extracts possess antimicrobial activities against many microorganisms (Collins and Charles, 1987; Hao et al., 1998; Fernandez-Lopez et al., 2005; Fan et al., 2006; Rižnar et al., 2006). Natural products from rosemary are on the Generally Recognized as Safe (GRAS) list, which means that they are recognized as safe for use in food products (Gerard et al., 1995).

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Herbs and Spices Commonly-Used in Foods

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SAGE (Salvia officinalis L.)

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Figure 8. Sage (Salvia officinalis L).

Sage belongs to the Lamiaceae family, a perennial woody sub-shrub native to the Mediterranean region that is now extensively cultivated all over the world, mainly to obtain dried leaves to be used as raw material in medicine, perfumery, and food industry (Bruneton, 1999). Apart from general scientific curiosity, understanding the chemistry of Salvia plants is important for several commercial industries because these plants have been utilized for flavouring food, cosmetic formulations, aromatherapy, and insecticides. The positive benefits of sage to health are reputed throughout Ancient Romans times and the Middle Ages. A quote such as: ‘Cur moriatur homo cui Salvia crescit in horto?’(‘Why should a man die whilst sage grows in his garden?’) demonstrates the impact of sage on that society at the time (Kamatou et al., 2008). The leaves of sage contain high amounts of phenolic diterpenes such as carnosol and carnosic acid. Sage essential oil compositions include bornyl acetate (2.5%), camphene (1.5 to 7%), camphor (4.5 to 24.5%), 1,8-cineole (5.5 to 13%), cis-thujone (18 to 43%), α-humulene (0 to 12%), limonene (0.5 to 3%), linalool (1%), α-pinene (1 to 6.5%), and trans-thujone (3 to 8.5% (Bruneton, 1999). It has been reported that sage the affects central nervous system acetylcholine receptor activity, with demonstration of both nicotinic and muscarinic binding properties (Wake et al., 2000).

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In addition, it has been found that sage polysaccharides, crude or purified were strong scavengers of free radicals as well as inhibitors of liposomes peroxidation (Capek et al., 2009). The effectiveness of sage on the growth inhibition of the microorganisms is probably due to major substances such as thymol and carvacrol present in them (Akgul, 1993).

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raw and cooked chicken during refrigerated storage. Food Res. Int. 36: 207-213. Botsoglou, N.A., Florou-Paneri, P., Christaki, E., Giannenas, I. and Spais, A.B. 2004. Performance of rabbits and oxidative stability of muscle tissues as affected by dietary supplementation with oregano essential oil. Arch. Anim. Nutr. 58: 209-218. Bruneton, J. 1999. Pharmacognosy, Phytochemistry Medicinal Plants. 2nd ed. Intercept, London, 1119 pp. Burt, S. 2004. Essential oils: their antibacterial properties and potential applications in foods-a review. Int. J. Food Microbiol. 94: 223-253. Capek, P., Machova, E. and Turjan, J. 2009. Scavenging and antioxidant activities of immunomodulating polysaccharides isolated from Salvia officinalis L. Int. J. Biol. Macromol. 44: 75-80. Chan, E.W.C., Lim, Y.Y., Wong, L.F., Lianto, F.S., Wong, S.K., Lim, K.K., Joe, C.E. and Lim, T.Y. 2008. Antioxidant and tyrosinase inhibition properties of leaves and rhizomes of ginger species. Food Chem. 109: 477-483. Chen, C.C., Kuo, M.C., Wu, C.M.. and Ho, C.T. 1986. Pungent compounds of ginger (Zingiber officinale Rosc) extracted by liquid carbon dioxide. J. Agric. Food Chem. 34: 477-480. Chen, I-N., Chang, C-C., Ng, C-C., Wang, C-Y., Shyu, Y-T. and Chang, T-L. 2008. Antioxidant and antimicrobial activity of zingiberaceae plants in Taiwan. Plant Foods Hum. Nutr. 63: 15-20. Collins, M.A. and Charles, H.P. 1987. Antimicrobial activity of carnosol and ursolic acid: two antioxidant constituents of Rosmarinus officinalis L. Food Microbiol. 4: 311-315. Daferera, D.J., Basil, B.N., Ziogas, N. and Polissiou, M.G. 2003. The effectiveness of plant essential oils on Botrytis cinerea, Fusarium spp. and Clavibacter michiganensis subsp. michiganensis. Crop Prot. 22: 39-44. Daferera, D.J., Ziogas, B.N., and Polissiou, M.G. 2000. GC-MS analysis of essential oils from some Greek aromatic plants and their fungitoxicity on Penicillum digitatum. J. Agric. Food Chem. 48: 2576-2581. Dmetzos, C., Perdetzoglou, D.K. and Tan, K. 2001. Composition and antimicrobial studies of the oils of Origanum calcaratum Juss. and O. scabrum Boiss. et Heldr. from Greece. J. Essent. Oil Res. 13: 460-462. Dorman, H.J.D. and Deans, S.G. 2000. Antimicrobial agents from plants: Antibacterial activity of plant volatile oils. J. Appl. Microbiol. 88: 308316.

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Dwivedi, C., Abu-Ghazaleh, A. and Guenther, J. 1996. Effects of diallyl sulfide and diallyl disulfide on cisplantin-induced changes in glutathione and glutathione-S-transferase activity. Anti-cancer drugs 7: 792-794. Ernst, E. and Pittler, M.H. 2000. Efficacy of ginger for nausea and vomiting: A systematic review of randomized clinical trials. Br. J. Anaesth. 84: 367371. Estevez, M., Ventanas, S., Ramırez, R. and Cava, R. 2005. Influence of the addition of rosemary essential oil on the volatiles pattern of porcine frankfurters. J. Agric. Food Chem. 53: 8317-8324. Fan, X., Sommers, C.H. and Sokorai, K.J.B. 2006. Reduction of irradiationinduced quality changes by rosemary extract in ready-to-eat turkey meat product. Acta Hortic. 709: 61-67. Farnsworth, N.R. and Bunyapraphatsara, N. 1992. Thai Medicinal Plants: Recommended for Primary Health Care System. Prachachon Co. Ltd., Bangkok, 402 pp. Fernandez-Lopez, J., Zhi, N., Aleson-Carbonell, L., Perez-Alvarez, J.A. and Kuri, V. 2005. Antioxidant and antibacterial activities of natural extracts: application in beef meatballs. Meat Sci. 69: 371-380. Fista, G.A., Bloukas, J.G. and Siomos, A.S. 2004. Effect of leek and onion on processing and quality characteristics of Greek traditional sausages. Meat Sci. 68: 163-172. Fleischauer, A. and Arab, L. 2001. Garlic and cancer: A critical review of the epidemiologic literature. J. Nutr. 131: 1032S-1040S. Gerard, D., Quirin, K.W. and Schwarz, E. 1995. CO2-extracts from rosemary and sage. Int. Food Market Tech. 9: 46-55. Govaris, A., Botsoglou, N., Papageorgiou, G., Botsoglou, E. and Ambrosiadis, I. 2004. Dietary versus post-mortem use of oregano oil and/or αtocopherol in turkeys to inhibit development of lipid oxidation in meat during refrigerated storage. Int. J. Food Sci. Nutr. 55: 115-123. Govindarajan, V.S. 1980. Turmeric-chemistry, technology and quality. Crit. Rev. Food Sci. Nutr. 12: 199-301. Habsah, M., Amran, M., Mackeen, M.M., Lajis, N.H., Kikuzaki, H., Nakatani, H., Rahman, A., Ghafar, A. and Ali, A.M. 2000. Screening of Zingiberaceae extracts for antimicrobial and antioxidant activities. J. Ethnopharmacol. 72: 403-410. Hao, Y.Y., Brackett, R.E. and Doyle, M.P. 1998. Efficacy of plant extracts in inhibiting Aeromonas hydrophila and Listeria monocytogenes in refrigerated, cooked poultry. Food Microbiol. 15: 367-378.

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Harber, D., Siess, M.H. and Canivenc-Lavier, M.C. 1995. Differential effects of dietary diallyl sulfide and diallyl disulfide on rat intestinal and hepatic drug-metabolizing enzymes. J. Toxicol. Env. Heal. A 44: 423-434. Huisman, M., Madsen, H.L., Skibsted, L.H. and Bertelsen, G. 1994. The combined effect of rosemary (Rosmarinus officinalis L.) and modified atmosphere packaging as protection against warmed-over flavour incooked minced pork meat. Z. Lebensm. Unters. F. A. 198: 57-59. Ifesan, B.O.T, Siripongvutikorn, S., Thummaratwasik, P. and Kantachote, D. 2009. Stability of antibacterial property of Thai green curry during chilled storage. J. Food Process. Preserv. 34: 308-321. Iqbal, S. and Bhanger, M.I. 2007. Stabilization of sunflower oil by garlic extract during accelerated storage. Food Chem. 100: 246-254. Jitoe, A., Masuda, T., Tengah, I.G.P., Suprapta, D.N., Gara, I.W. and Nakatani, N. 1992. Antioxidant activity of tropical ginger extracts and analysis of the contained curcuminoids. J. Agric. Food Chem. 40: 13371340. Kaefer, C.M. and Milner, J.A. 2008. Reviews: The role of herbs and spices in cancer prevention. J. Nutr. Biochem. 19: 347-361. Kamatoua, G.P.P., Makungab, N.P., Ramogolab, W.P.N. and Viljoena, A.M. 2008. South African Salvia species: A review of biological activities and phytochemistry. J. Ethnopharmacol. 119: 664-672. Lanzotti, V. 2006. The analysis of onion and garlic. J. Chrom. 1112: 3-22. Lawson, L.D. 1996. Garlic: A review of its medicinal effects and indicated active compounds. In: Lawson, L.D. and Bauer, R. eds., Phytomedicines of Europe: Their Chemistry and Biological Activity. ASC Press, Washington DC, pp. 176-209. Lawson, L.D. and Hughes, B.G. 1992. Characterization of the formation of allicin and other thiosulfinates from garlic. Planta Med. 58: 345-350. Leung, A.Y. and Foster, S. 1996. Encyclopedia of Common Natural Ingredients Used in Foods, Drugs and Cosmetics. 2nd ed. John Wiley & Sons, Inc., New York, 648 pp. Martins, A.P., Salgueiro, L., Goncalves, M.J., da Cunha, A.P., Vila, R., Canigueral, S., Mazzoni, V., Tomi, F. and Casanova, J. 2001. Essential oil composition and antimicrobial activity of three Zingiberaceae from S. Tomé e Príncipe. Planta Med. 67: 580-584. Mau, J.L., Eric Lai, Y.C., Wang, N.P., Chen, C.C., Chang, C.H. and Chyau, C.C. 2003. Composition and antioxidant activity of the essential oil from Curcuma zedoaria. Food Chem. 82: 583-591.

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Mayachiew, P. and Devahastin, S. 2007. Antimicrobial and antioxidant activities of Indian gooseberry and galangal extracts. LWT 41: 1153-1159. Nakatani, N. 2000. Phenolic antioxidants from herbs and spices. Biofactors 13: 141-146. Nakatani, N. 2003. Biologically functional constituents of spices and herbs. J. Jpn. Soc. Nutr. Food Sci. 56: 389-395. Novak, J., Christina, B., Langbehn, B., Pank, F., Skoula, M., Gotsiou, Y. and Franz, C.M. 2000. Ratios of cis- and trans-sabinene hydrate in Origanum majorana L. and Origanum midrophyllum (Bentham) Vogel. Biochem. Systemat. Ecol. 28: 697-704. Oonmetta-aree, J., Suzuki, T., Gasaluck, P. and Eumkeb, G. 2006. Antimicrobial properties of action of galangal (Alpinia galanga Linn.) on Staphylococcus aureus. LWT 39: 1214-1220. Raina, V.K., Srivastava, S.K. and Syamasunder, K.V. 2002. The essential oil of ‘greater galangal’ [Alpinia galanga (L.) Willd.] from the lower Himalayan region of India. Flavour Frag. J. 17: 358-360. Reddy, A.C.P. and Lokesh, B.R. 1992. Studies on spice principles as antioxidants in the inhibition of lipid peroxidation of rat liver microsomes. Mol. Cell Biochem. 111: 117-124. Rižnar, K., Celan, S., Knez, Z., Skerget, M., Bauman, D., and Glaser, R. 2006. Antioxidant and antimicrobial activity of rosemary extract in chicken frankfurters. J. Food Sci. 7: 425-429. Ryman, D. 1992. Aromatherapy. The Encyclopaedia of Plants and Oils and How They Help You. Piatkus Books, London, pp. 163-165. Sahin F., Gulluce, M., Daferera, D., Sokmen, A., Sokmen, M., Polissiou, M., Agar, G. and Ozer, H. 2004. Biological activities of the essential oils and methanol extract of Origanum vulgare ssp. vulgare in the Eastern Anatolia region of Turkey. Food Control 15: 549-557. Sallam, K.I., Ishioroshi, M. and Samejima, K. 2004. Antioxidant and antimicrobial effects of garlic in chicken sausage. LWT 37: 849-855. Sanchez-Escalante, A., Djenane, D., Torrescano, G., Gimenez, B., Beltran, J.A. and Roncales, P. 2001. The effects of ascorbic acid, taurine, carnosine and rosemary powder on colour and lipid stability of beef patties packaged in modified atmosphere. Meat Sci. 58: 421-429. Shahidi, F. and Wanasundara, P.K. 1992. Phenolic antioxidants. CRC Crit. Rev. Food Sci. Nutr. 32: 67-103. Siripongvutikorn, S., Thummaratwasik, P. and Huang, Y. 2005. Antimicrobial and antioxidant effects of Thai seasoning, Tom-Yum. LWT 38: 347-352.

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Sivropoulou, A., Papanikolaou, E., Nikolaou, C., Kokkini, S., Lanaras, T. and Arsenakis, M. 1996. Antimicrobial and cytotoxic activities of Origanum essential oils. J. Agric. Food Chem. 44: 1202-1205. Skandamis, P.N. and Nychas, G.-J.E. 2001. Effect of oregano essential oil on microbiological and physico-chemical attributes of minced meat stored in air and modified atmospheres. J. Appl. Microbiol. 91: 1011-1022. Skerget, M., Kotnik, P., Hadolin, M., Hras, A.R., Simonic, M. and Knez, Z. 2005. Phenols, proanthocyanidins, flavones and flavonols in some plant materials and their antioxidant activities. Food Chem. 89: 191-198. Sokovic, M., Tzakou, O., Pitarokili, D. and Couladis, M. 2002. Antifungal activities of selected aromatic plants growing wild in Greece. Nahrung Food 46: 317-320. Stoick, S.M., Gray, J.I., Booren, A.M. and Buckley, D.J. 1991. Oxidative stability of restructured beef steaks processed with oleoresin rosemary, tertiary butylhydroquinone, and sodium tripolyphosphate. J. Food Sci. 56: 597-600. Suhaj, M. 2006. Spice antioxidants isolation and their antiradical activity: a review. J. Food Compost. Anal. 19: 531-537. Tabanca, N., Demirci, F., Ozek, T., Tumen, G. and Baser, K.H.C. 2001. Composition and antimicrobial activity of the essential oil of Origanum × dolichosiphon P.H. Davis. Chem. Nat. Compd. 37: 238-241. Tang, X. and Cronin, D.A. 2007. The effects of brined onion extracts on lipid oxidation and sensory quality in refrigerated cooked turkey breast rolls during storage. Food Chem. 100: 712-718. United States Department of Agriculture Economic Research Service (USDA/ERS). 2007. < http://www.ers.usda.gov/Data/Food>. Voravuthikunchai, S.P. 2007. Family Zingiberaceae compounds as functional antimicrobials, antioxidants, and antiradicals. Food 1: 227-240. Voravuthikunchai, S.P., Phongpaichit, S. and Subhadhirasakul, S. 2005. Evaluation of antibacterial activities of medicinal plants widely used among AIDS patients in Thailand. Pharm. Biol. 43: 701-706. Voravuthikunchai, S.P., Limsuwan, S., Supapol, O. and Subhadhirasakul, S. 2006. Antibacterial activity of extracts from family Zingiberaceae against foodborne pathogens. J. Food Safety 26: 325-334. Wake, G., Court, J., Pikering, A., Lewis, R., Wilkins, R. and Perry, E. 2000. CNS acetylcholine receptor activity in European medicinal plants traditionally used to improve failing memory. J. Ethnopharmacol. 69: 105-114.

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Wang, H. and Ng, T.B. 2005. An antifungal protein from ginger rhizomes. Biochem. Bioph. Res. Co. 336: 100-104. Yang, X. and Eilerman, R.G. 1999. Pungent principal of Alpinia galanga (L.) Swartz and its applications. J. Agric. Food Chem. 47: 1657-1662. Yeh, Y.Y. and Liu, L. 2001. Cholesterol-lowing effect of garlic extracts and organosulfur compounds: human and animals studies. J. Nutr. 131: 989S993S. Yu, L., Scanlin, L., Wilson, J. and Schmidt, G. 2002. Rosemary extract as inhibitors of lipid oxidation and colour change in cooked turkey products during refrigerated storage. J. Food Sci. 67: 582-585.

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Chapter 3

BIOACTIVE COMPOUNDS FROM PLANTS

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ESSENTIAL OILS AND TERPENOIDS Essential oils are aromatic oily liquids obtained from plant materials such as flowers, buds, seeds, leaves, twigs, bark, herbs, wood, fruits, and roots (Guenther, 1948). The compounds containing additional elements usually oxygen are called ‘terpenoids’ (Cowan, 1999). Essential oils can be obtained by expression, fermentation, enfleurage, or extraction. However, the method of steam distillation is most commonly preferred for commercial production of essential oils (Van de Braak and Leijten, 1999). It is well-documented in the literatures that some essential oils have antimicrobial properties (Guenther, 1948; Boyle, 1955; Shelef, 1983; Nychas, 1995; Dorman and Deans, 2000; Burt, 2004; Holley and Patel, 2005). In addition, essential oils are used as food flavourings, either extracted from plant materials or synthetically manufactured (Oosterhaven et al., 1995; Burt, 2004; Rajkovic et al., 2005). Examples of other common terpenoids are camphor (monoterpenes), artemisin and farnesol. Terpenes or terpenoids have been shown to possess antibacterial activities (Habtemariam et al., 1993; Tassou et al., 1995; Mendoza et al., 1997). Common essential oils are available in cilantro, coriander, cinnamon, oregano, rosemary, sage, clove, and thyme. Carvacrol is a major component of the essential oils of oregano and thyme (Lagouri et al., 1993; Arrebola et al., 1994). Cinnamic acid is structurally similar and occurs in cinnamon, cloves, black pepper, coriander and turmeric. Both compounds are GRAS and commonly employed as flavouring agents in baked goods, sweets, ice cream, beverages, and chewing gum (Burdock, 1995).

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FLAVONES, FLAVONOIDS, FLAVONOLS

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Flavones are phenolic structures containing one carbonyl group. Flavonoids are hydroxylated phenolic substances which are known to be synthesized by plants in response to microbial infections (Dixon et al., 1983). Plant phenolics, especially dietary flavonoids, are currently of growing interest owing to their supposed functional properties in promoting human health (Rauha et al., 2000) and may also exhibit useful antibacterial activity (Harborne and Williams, 2000). Flavonoids possess broad spectrum pharmacological activities which include anticarcinogenic (Lin et al., 2006; Pierini et al., 2008), anti-inflammatory, anti-allergenic, antiasthmatic, antiartherogenic, anti-thrombotic, antiallergic effects as well as cardiovascular and cerebrovascular actions (Manach et al., 2005; Urios et al., 2007). Flavonoids are the most abundant group of plant phenolic compounds which act as antioxidants (Rice-Evans and Miller, 1996). Flavonoids occur very widely in plants used as human foods (Hollman and Arts, 2000), and much of the colour, flavour, and aroma of chocolate, tea, coffee, and wine reflects the complex variety of phenolic compounds that they contain. Examples of herbs and spices with flavonoids include nutmeg, peppermint, onion, and rosemary.

ORGANOSULFUR COMPOUNDS The rich content of the numerous organosulfur compounds in garlic plays a key role in health-related functions (LeBon and Siess, 2000). Among the garlic organosulfur compounds, diallyl sulfide, diallyl disulfide, and diallyl trisulfide, which differ in their numbers of sulfur atoms, are the three major volatile allyl sulfides in garlic oil (Yu et al., 1989). Garlic displays diverse biological activities including antithrombotic, antiatherosclerotic, antidiabetic, antioxidant activities, and immune modulation (Lamm and Riggs, 2001; Ou et al., 2003; Peleg et al., 2003; Thomson and Ali, 2003). Ingestion of garlic has also been reported to lower the concentration of triglycerides, cholesterol, and low-density lipoproteins and increase the concentration of high-density lipoproteins in blood (Naidu, 2000). In addition, garlic oils and organosulfides obtained from plants have been demonstrated to inhibit carcinogenesis (Belman, 1983; Sparnins et al., 1986; Belman et al., 1987; Wargovich et al., 1987). The antibiotic activity of 1 mg of allicin, (+)-S-methyl-l-cysteine sulphoxide, has been equated to that of 15 international unit (IU) of penicillin, a β-lactam antibiotic (Han et al., 1995).

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PHENOLICS AND POLYPHENOLS Catechol and pyrogallol are hydroxylated phenols, and have been shown to be toxic to microorganisms. Highly oxidized phenols have been demonstrated to produce more inhibitory effect (Urs and Dunleavy, 1975; Scalbert, 1991). In addition, polyphenols belong to the category of natural antioxidants (Boskou and Visioli, 2003). Natural polyphenolics containing high percentage of phenols demonstrated their beneficial health effects by their antioxidant activity. These compounds are capable of removing free radicals, chelate metal catalysts, activate antioxidant enzymes, reduce α-tocopherol radicals, and inhibit oxidases (Amić et al., 2003). Cinnamic and caffeic acids, coriander, cumin, nutmeg, oregano, peppermint, rosemary, and tea are common representatives of a wide group of phenylpropane-derived compounds which are in the highest oxidation state.

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QUINONES Quinones are highly reactive and provide a source of stable free radicals. They are known to irreversibly complex with nucleophilic amino acids in proteins (Stern et al., 1996), leading to the inactivation of protein. Quinones are common constituents of biologically-relevant molecules including vitamin K1. Others serve as electron acceptors in electron transport chains such as those in Photosystems I and II of photosynthesis and aerobic respiration. Quinones can be partially reduced to quinols. Many natural or synthetic quinones show biological or pharmacological activity, and some of them show antitumoral (Bolognese et al., 2002) and antimalarial (De Andrade-Neto et al., 2004) activity. The largest subgroup of natural quinones are the napthoquinones. These include eleutherin, elecanacin, eleutherinoside A, eleuthoside B, hogconin, isoeleutherin, isoeleutherol, and naphthalene, which were isolated from Eleutherine americana (Zhengxiong et al., 1984; Hara et al., 1997; Qui et al., 2005; Xu et al., 2006; Paramapojn et al., 2008; Ifesan et al., 2009), and Eleutherine bulbosa (Alves et al., 2003).

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TANNINS

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Tannins are defined as naturally occurring water soluble polyphenols of varying molecular weight. They differ from most other natural phenolic compounds due to their ability to precipitate proteins from solutions (Spencer et al., 1988). They are group polymeric phenolic substances that can precipitate gelatin from solution, which is described as astringency. They are found in almost every plant parts including bark, wood, leaves, fruits, and roots (Haslam, 1989; Scalbert, 1991). Tannins are divided into two groups, namely, hydrolyzable and condensed tannins. Hydrolyzable tannins are based on gallic acid, esters of gallic acid (gallotannins) or ellagic acid (ellagitannins) while the more numerous condensed tannins are derived from flavonoid monomers (Bhat et al., 1998). In addition, tannins may be obtained by polymerization of quinone units (Geissman, 1963). They are common in tropical shrub legumes (MuellerHarvey et al., 2006) and tea leaves (Graham, 1992). Tannins inhibit the growth of a number of microorganisms, resist microbial attack, and are recalcitrant to biodegradation (Field and Lettinga, 1992). Plants with high tannins have been reported to be able to demonstrate a wide range of antibacterial (Voravuthikunchai and Suwalak, 2008; Chusri and Voravuthikunchai, 2009), and anti-infective actions (Haslam, 1996).

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Belman, S., Block, E., Pechellet, J.P., Perchellet, E.M. and Fischer, S.M. 1987. Onion and garlic oils inhibit promotion whereas oils enhance conversion of papillomas to carcinomas. Proc. Am. Assoc. Cancer Res. 28: 659. Bhat, T.K., Singh, B. and Sharma, O.P. 1998. Microbial degradation of tannins-A current perspective. Biodegradation 9: 343-357. Bolognese, A., Correale, G., Manfra, M., Lavecchia, A., Mazzoni, O., Novellino, E., Barone, V., La Colla, P. and Loddo, R. 2002. Antitumor agents. 2. Synthesis, structure-activity relationships, and biological evaluation of substituted 5H-pyridophenoxazin-5-ones with potent antiproliferative activity. J. Med. Chem. 45: 5217-5223. Boskou, D. and Visioli, F. 2003. Biophenols in table olives. In: Vaquero, M.P., Garcia-Arias, T. and Garbajal, A. eds., Bioavailability of Micronutrients and Minor Dietary Compounds. Metabolic and Technical Aspects. Research Signpost., Trivandrum. pp. 161-169. Boyle, W. 1955. Spices and essential oils as preservatives. Am. Perfum. Essent. Oil Rev. 66: 25-28. Burdock, G.A. 1995. Fenaroli’s Handbook of Flavor Ingredients. 3rd ed. CRCPress LLC, Boca Raton, 368 pp. Burt, S. 2004. Essential oils: their antibacterial properties and potential applications in foods-a review. Int. J. Food Microbiol. 94: 223-253. Chusri, S. and Voravuthikunchai, S.P. 2009. Detailed studies on Quercus infectoria Oliver (nutgalls) as an alternative treatment for methicillinresistant Staphylococcus aureus. J. Appl. Microbiol. 106: 89-96. Cowan, M.M. 1999. Plant products as antimicrobial agents. Clin. Microbiol. Rev. 12: 564-582. De Andrade-Neto, V.F., Goulart, M.O.F., da Silva Filho, J.F., da Silva, M.J., Pinto, M.C.F.R., Pinto, A.V., Zalis, M.G., Carvalho, L.H. and Krettli, A.U. 2004. Antimalarial activity of phenazines from lapachol, βlapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Bioorg. Med. Chem. Lett. 14: 1145-1149. Dixon, R.A., Dey, P.M. and Lamb, C.J. 1983. Phytoalexins: Enzymology and molecular biology In: Meister, A. ed., Advances in Enzymology and Related Areas of Molecular Biology, Vol. 55. John Wiley & Sons, Inc., New York, pp. 1-69. Dorman, H.J.D. and Deans, S.G. 2000. Antimicrobial agents from plants: Antibacterial activity of plant volatile oils. J. Appl. Microbiol. 88: 308316.

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Field, J.A. and Lettinga, G. 1992. Toxicity of tannic compounds to microorganisms. In: Hemingway, R.W. and Laks, E. eds., Plant Polyphenols: Synthesis, Properties, Significance. Plenum Press, New York, pp. 673-692. Geissman, T.A. 1963. Flavonoid compounds, tannins, lignins and related compounds. In: Florkin, M. and Stotz, E.H. eds., Comprehensive Biochemistry, Vol. 9. Pyrrole Pigments, Isoprenoid Compounds and Phenolic Plant Constituents. Elsevier, New York, p. 265. Graham, H.N. 1992. Green tea composition, consumption and polyphenol chemistry. Prev. Med. 21: 334-350. Guenther, E. 1948. The Essential Oils. D. Van Nostrand, New York, 427 pp. Habtemariam, S., Gray, A.I. and Waterman, P.G. 1993. A new antibacterial sesquiterpene from Premna oligotricha. J. Nat. Prod. 56: 140-143. Han, J., Lawson, L., Han, G. and Han, P. 1995. A spectrophotometric method for quantitative determination of allicin and total garlic thiosulfinates. Anal. Biochem. 225: 157-160. Hara, H., Maruyama, N., Yamashita, S., Hayashi, Y., Lee, K., Bastow, K.F., Chairul, M.R., Marumoto, R. and Imakura, Y. 1997. Elecanacin, a novel new naphthoquinone from the bulb of Eleutherine americana. Chem. Pharm. Bull. 45: 1714-1716. Harborne, J.B. and Williams, C.A. 2000. Advances in flavonoid research since 1992. Phytochemistry 55: 481-504. Haslam, E. 1989. Plant Polyphenols-Vegetable Tannins Revisited. Cambridge University Press, Cambridge, 230 pp. Haslam, E. 1996. Natural polyphenols (vegetable tannins) as drugs: possible modes of action. J. Nat. Prod. 59: 205-215. Holley, R.A. and Patel, D. 2005. Improvement in shelf life and safety of perishable foods by plant essential oils and smoke antimicrobials. Food Microbiol. 22: 273-292. Hollman, P.C.H. and Arts, I.C.W. 2000. Flavonols, flavones and flavanolsnature, occurrence and dietary burden. J. Sci. Food Agric. 80: 1081-1093. Ifesan, B.O.T., Hamtasin, C., Mahabusarakam, W. and Voravuthikunchai, S.P. 2009. Assessment of antistaphylococcal activity of semi-purified fractions and pure compounds from Eleutherine americana. J. Food Prot. 72: 354359. Lagouri, V., Blekas, G., Tsimidou, M., Kokkini, S. and Boskou, D. 1993. Composition and antioxidant activity of essential oils from oregano plants grown wild in Greece. Z. Lebens. Unters. Forsch. 197: 20-23.

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Lamm, D.L. and Riggs, D.R. 2001. Enhanced immunocompetence by garlic: role in bladder cancer and other malignancies. J. Nutr. 131: 1067S-1070S. LeBon, A. and Siess, M. 2000. Organosulfur compounds from Allium and the chemoprevention of cancer. Drug Metabol. Drug Interact. 17: 51-79. Lin, J., Zhang, S.M., Wu, K., Willett, W.C., Fuchs, C.S. and Giovannucci, E. 2006. Flavonoid intake and colorectal cancer risk in men and women. Am. J. Epidemiol. 164: 644-651. Manach, C., Mazur, A. and Scalbert, A. 2005. Polyphenols and prevention of cardiovascular diseases. Curr. Opin. Lipidol. 16: 77-84. Mendoza, L., Wilkens, M. and Urzua, A. 1997. Antimicrobial study of the resinous exudates and of diterpenoids and flavonoids isolated from some Chilean Pseudognaphalium (Asteraceae). J. Ethnopharmacol. 58: 85-88. Mueller-Harvey, I., Hartley, R.D. and Reed, J.D. 1987. Characterization of phenolic compounds, including flavonoids and tannins of ten ethiopian browse species by high performance liquid chromatography. J. Sci. Food Agric. 39: 1-14. Naidu, A.S. 2000. Natural Food Antimicrobial Systems. 3rd ed. CRC Press, Boca Raton, 818 pp. Nychas, G.J.E. 1995. Natural antimicrobials from plants. In: Gould, G.W. ed., New Methods of Food Preservation. Blackie Academic and Professional, London, pp. 58-89. Oosterhaven, K., Poolman, B. and Smid, E.J. 1995. S-carvone as a natural potato sprout inhibiting, fungistatic and bacteristatic compound. Ind. Crop. Prod. 4: 23-31. Ou, C.C., Tsao, S.M., Lin, M.C. and Yin, M.C. 2003. Protective action on human LDL against oxidation and glycation by four organosulfur compounds derived from garlic. Lipids 38: 219-224. Paramapojn, S., Ganzera, M., Gritsanapan, W. and Stuppner, H. 2008. Analysis of naphthoquinone derivatives in the Asian medicinal plant Eleutherine americana by RP-HPLC and LC-MS. J. Pharm. Biomed. Anal. 47: 990-993. Peleg, A., Hershcovici, T., Lipa, R., Anbar, R., Redler, M. and Beigel, Y. 2003. Effect of garlic on lipid profile and psychopathologic parameters in people with mild to moderate hypercholesterolemia. Is. Med. Asso. J. 5: 637-640. Pierini, R., Gee, J.M., Belshaw, N.J. and Johnson, I.T. 2008. Flavonoids and intestinal cancers. Brit. J. Nutr. 99: (E-Suppl. 1) ES53-ES59.

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Qui, F., Xu, J.Z., Duan, W.J., Qu, G.X., Wang, N.L. and Yao, X.S. 2005. New constituents from Eleutherine americana. Chem. J. Chinese Universities 26: 2057-2060. Rajkovic, A., Uyttendaele, M., Courtens, T. and Debevere, J. 2005. Antimicrobial effect of nisin and carvacrol and competition between Bacillus cereus and Bacillus circulans in vacuum-packed potato puree. Food Microbiol. 22: 189-197. Rauha, J.P., Remes, S., Heinonen, M., Hopia, A., Kahkonen, M., Kujala, T., Pihlaja, K., Vuorela, H. and Vuorela, P. 2000. Antimicrobial effects of Finnish plant extracts containing flavonoids and other phenolic compounds. Int. J. Food Microbiol. 56: 3-12. Rice-Evans, C.A. and Miller, N.J. 1996. Antioxidant activities of flavonoids as bioactive components of food. Biochem. Soc. Trans. 24: 790-795. Scalbert, A. 1991. Antimicrobial properties of tannins. Phytochemistry 30: 3875-3883. Shelef, L.A. 1983. Antimicrobial effects of spices. J. Food Safety 6: 29-44. Sparnins, V.L., Mott, A.W., Barany, G. and Wattenberg, L.W. 1986. Effects of allyl methyl trisulfide on glutathione S-transferase activity and BPinduced neoplasia in the mouse. Nutr. Cancer 8: 211-215. Spencer, C.M., Cai, Y., Martin, R., Gaffney, S.H., Goulding, P.N., Magnolato, D., Lilley, T.H. and Haslam, E. 1988. Polyphenol complexation-some thoughts and observations. Phytochemistry 27: 2397-2409. Stern, J.L., Hagerman, A.E., Steinberg, P.D. and Mason, P.K. 1996. Phlorotannin-protein interactions. J. Chem. Ecol. 22: 1887-1899. Tassou, C.C., Drosinos, E.H. and Nychas, G.-J.E. 1995. Effects of essential oil from mint (Mentha piperita) on Salmonella enteritidis and Listeria monocytogenes in model food systems at 4° and 10°C. J. Appl. Bacteriol. 78: 593-600. Thomson, M. and Ali, M. 2003. Garlic (Allium sativum): a review of its potential use as an anti-cancer agent. Curr. Cancer Drug Tar. 3: 67-81. Urios, P., Grigorova-Borsos, A.-M. and Sternberg, M. 2007. Flavonoids inhibit the formation of the cross-linking AGE pentosidine in collagen incubated with glucose, according to their structure. Eur. J. Nutr. 46: 139146. Urs, N.V. and Dunleavy, J.M. 1975. Enhancement of the bactericidal activity of a peroxidase system by phenolic compounds. Phytopathology 65: 686690.

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Van de Braak, S.A.A.J. and Leijten, G.C.J.J. 1999. Essential Oils and Oleoresins: A Survey in the Netherlands and Other Major Markets in the European Union. CBI, Centre for the Promotion of Imports from Developing Countries, Rotterdam, p. 116. Voravuthikunchai, S.P. and Suwalak, S. 2008. Antibacterial activities of semipurified fractions of Quercus infectoria against enterohemorrhagic Escherichia coli O157:H7 and its Verocytotoxin production. J. Food Prot. 71: 1223-1227. Wargovich, M.J. 1987. Diallyl sulfides, a flavour component of garlic (Allium sativum) inhibits dimethylhydrazine-induced colon cancer. Carcinogenesis 8: 487-489. Xu, J., Qui, F., Duan, W., Qu, G., Wang, N. and Yao, X. 2006. New Bioactive constituents from Eleutherine americana. Front. Chem. China 3: 320-323. Yu, T.H., Wu, C.M. and Liou, Y.C. 1989. Volatile compounds from garlic. J. Agric. Food Chem. 37: 725-730. Zhengxiong, C., Huizhu, H., Chengrui, W., Yuhui, L., Jianmi, D., Sankawa, U., Noguchi, H. and Iitaka, Y. 1984. Hongconin, a new naphthalene derivative from the rhizome of Eleutherine americana (Hong-Cong). Heterocycles 22: 691-694.

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Chapter 4

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COMMON FOODBORNE PATHOGENS Foodborne disease has been defined by the World Health Organization (WHO) as a disease of an infectious or toxic nature caused by, or thought to be caused by, the consumption of food or water (Adams and Moses, 1995). A variety of microorganisms have led to food spoilage that is encountered as one of the most important matter concerning the food industry. Bacteria can colonize a range of food preparation surfaces and kitchens (Scott et al., 1982; Scott and Bloomfield, 1990; Altekruse et al., 1995; Woodburn and Raab, 1997; Rusin et al., 1998; Sharp and Walker, 2003), utensils, domestic dishcloths, sponges, other cleaning materials (Spiers et al., 1995; Rusin et al., 1998; Sharp and Walker, 2003), and the interior surfaces of household refrigerators (Ryan et al., 1996; Michaels et al., 2001; Jackson et al., 2007) from which they can be transferred into foods (Rusin et al., 2002) through clothes, hands, utensils (Scott and Bloomfield, 1990; Rusin et al., 2002). Other studies have implicated environmental surfaces in the transmission of bacteria into foods (Bures et al., 2000; Manning et al., 2001). These agents are responsible for considerable morbidity and mortality in addition to costs for medical care, loss of productivity and control by the food industry. The increasing incidence of foodborne diseases, coupled with the resultant social and economic implications (Sockett and Roberts, 1991; Sockett, 1993) means there is a constant striving to search for new effective antimicrobial agents and to produce safer food. Most common foodborne bacteria include Bacillus cereus, Campylobacter jejuni, Clostridium botulinum, Clostridium perfringens, Escherichia coli, Listeria monocytogenes, Salmonella spp., Shigella spp., Staphylococcus aureus, Vibrio spp., and Yersinia enterocolitica. A list of foodborne pathogens together with their important characteristics is given in Table 2.

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Supayang Piyawan Voravuthikunchai and Wumi Ifesan Table 2. Important food poisoning organisms

Organisms Bacillus cereus (diarrhoeal type) Bacillus cereus (emetic type) Campylobacter spp. Clostridium botulinum Clostridium perfringens Escherichia coli (LT)# Escherichia coli (ST)# Listeria monocytogenes Salmonella spp.

Infective Incubation dose period 105-107 6-12 hours

Symptoms*

References

A, D, DH

Kramer and Gilbert, 1989

≥105

1-6 hours

A, V

Kramer and Gilbert, 1989

103-105 toxin

2-5 days BD, F 12-36 hours A, D, ND, V

108

6-16 hours

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A, D, DH Granum, 1990

105-108 16-18 hours

A, BD, DH

105-108

4-6 hours

D, F

107-108

1-90 days

I, M

10-106

A, D, DH, F, V

102-105

7 hours21 days 1-7 days

toxin

1-6 hours

108 103-104

2-5 days 9-24 hours

107

2-7 days

Doyle and Padhye, 1989 Doyle and Padhye, 1989 Schuchat et al., 1991

Shigella spp. Staphylococcus aureus Vibrio cholerae Vibrio parahaemolyticus Yersinia enterocolitica

Butzle and Oosterom, 1991 Hauschild, 1989

D’Aoust, 1989 A, BD, D, DH, F Wachsmuth and Morris, A, D, V 1989 Bergdoll, 1989 A, D, DH A, F, V Wachsmuth et al., 1994 Adams and Moses, 1995 A, D, DH, V Kapperud, 1991

*

A: abdominal pain, BD: bloody diarrhoea, D: diarrhoea, DH: dehydration, F: fever, I: influenza-like, M: meningitis, ND: neurological disturbances, V: vomiting # LT: heat-labile toxin, ST: heat-stable toxin

Bacillus cereus Bacillus cereus has been reported as one of the foodborne microorganisms of public health significance and foodborne illnesses (Kramer and Gilbert, 1989). The organism is a Gram-positive, facultatively aerobic spore-forming rod-shaped bacterium that is one of the most common foodborne pathogens causing both intoxications and infections. The growth domains of the Bacillus cereus genetic groups range from nearly thermophilic to psychrotrophic strains. The more thermophilic strains grow at 55°C or higher, the more psychrotrophic strains are able to grow at 5°C and seem to be

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less heat resistant (Guinebretiere et al., 2008). Different percentages in endospore germination at chilled temperatures among Bacillus cereus genetic groups was observed (Carlin et al., 2006). Contamination of food by Bacillus cereus is classified through emetic and diarrheoal symptoms (Granum, 2007). The symptoms are often associated with enterotoxin production which poses health hazard to consumers. Bacillus cereus causes two different types of gastrointestinal disorders, namely, emetic and diarrhoeal syndrome. Emetic syndrome is caused by a small cyclic heatstable peptide by ingestion of a preformed toxin in food which results in nausea and vomiting within one to six hours after ingestion. On the other hand, diarrhoeal syndrome is affected by enterotoxin production, a group of heatlabile protein that can be formed in food and also in small intestine, causing abdominal pain and diarrhoea after incubation for 8 to 16 hours (Granum 2007). This bacterium is commonly distributed in nature and it can easily contaminate many types of foods. Bacillus cereus food poisoning has been implicated as main hazards in raw rice (Ankolekar et al., 2009), rice-based products, farinaceous foods, pasta, noodles and cooked products such as spaghetti, cereals, infant milk, and rice (Becker et al., 1994; Sarrias et al., 2002; Duc et al., 2005; Reyes et al., 2006). Furthermore, Bacillus cereus has been isolated from a wide variety of foods including desert mixes (Warburton et al., 1987), ready to serve foods (Harmon and Kautter, 1991), cheese (Tham et al., 1990; Iurlina et al., 2006; Molva et al., 2008), meat and meat products (Güven et al., 2006; Konuma et al., 1988; Smith et al., 2004), milk and dairy products (Zhou et al., 2008), seafood (Wijnands et al., 2006; Rahmati and Labbe, 2008), spices (Konuma et al., 1988; Choo et al., 2007), and fresh vegetables, vegetable-based foods (Valero et al., 2007). Several outbreak reports in infant milk and milk products by endospore formers highlighted Bacillus cereus as an aetiologic agent which arouse concerns that products with extensive manufacturing processes can be contaminated with Bacillus cereus (Becker et al., 1994; Dierick et al., 2005; Reyes et al., 2006; Zhou et al., 2008). The occurrence of Bacillus cereus in pasteurized milk can be explained by the presence of their heat-resistant endospores in the raw milk or by milk recontamination, due to inadequately cleaned and sanitized surfaces (Zacarchenco et al., 2000; Boor, 2001; Hayes and Boor, 2001).

Campylobacter spp. Campylobacter is one of the most common causes of foodborne gastroenteritis worldwide. Campylobacteriosis is among the most frequently

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reported causes of bacterial gastroenteritis in humans in many developed and developing countries around the world (Bhaduri and Cottrell, 2004). In many industrialized countries, the incidence of Campylobacter disease is higher than Salmonella disease (European Food Safety Authority (EFSA), 2007). The frequency of Campylobacter infections generates numerous health care expenses. Furthermore, life-threatening systemic diseases are diagnosed more and more readily and the most severe Guillain Barre syndromes are the post infectious consequence, making the infection a major public health issue. The organism is a Gram-negative, motile, spiral-shaped bacterium that exists as a commensal organism in the gastrointestinal tracts of a variety of wild and domestic animals (Friedman et al. 2000). Many species are found in the intestinal tracts of many birds and mammals used for food production. Campylobacteriosis in humans is caused by thermotolerant species that can grow at 42°C. Campylobacter jejuni and Campylobacter coli are most frequently isolated from diarrhoeal patients (Friedman et al., 2000). Other species including Campylobacter lari (Simor and Wilcox, 1987) and Campylobacter upsaliensis (Goossens et al., 2002) are infrequently isolated from humans; however, both have been reported to cause human gastroenteritis. Poultry has been recognized as the primary reservoir of Campylobacter, hence poultry products may play an important role in the transmission of Campylobacter enteritis to humans (Humphrey et al., 2007). Surveys of raw agricultural products support epidemiologic evidence implicating poultry, meat, and raw milk as sources of human infections. Mishandling of raw poultry and consumption of undercooked poultry has been the major risk factors for human campylobacteriosis (Butzler and Oosterom, 1991; Altekruse et al., 1999; Nadeau et al., 2002; Kapperud et al., 2003; Friedman et al., 2004; Centers for Disease Control and Prevention (CDC), 2005; Wingstrand et al., 2006). Antibiotic resistance of Campylobacter is a growing concern for poultry (Zhang et al., 2003). Most retailed chickens are contaminated with Campylobacter jejuni (Morita et al., 2003; Ono et al., 2005; Shimizu et al., 2006; Watanabe et al., 2006; Fukushima et al., 2007; Sallam, 2007; Suzuki and Yamamoto, 2009; Wissessombat et al., 2009a; 2009b). Studies in the United States clearly showed that more than 80% of commercial chicken carcasses were positive for Campylobacter spp. (Kramer et al., 2000; Oyarzabal et al., 2004). Campylobacter is a frequent contaminant of many retail foods (Hood et al., 1988; Kramer et al., 2000), which poses public health challenges in terms of potential cross-contamination to food and food preparation surfaces during routine food preparation (Dawkins et al., 1984; Cogan et al., 1999). Cross-contamination of chickens may take place from raw chickens either directly to cooked chicken meat or some other components of the meal, or indirectly through knives, cutting board, or hands that have been in direct contact with raw meat or contaminated packages (Chen et al., 2001;

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Burgess et al., 2005; Luber et al., 2006). The bacterium can survive for extended periods on damp surfaces, especially at low temperature (Tholozan et al., 1999), but rapidly becomes undetectable in conditions of low water activity (Humphrey et al., 1995; Kusumaningrum et al., 2003). Its ability to transform into a viable but not culturable (VBNC) under such conditions does however mean that it may not be detected by culture-based methods.

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Clostridium spp. Several species of Clostridium have been isolated from soil, mud, sewage (Sinclair and Stokes, 1964), marine sediments (Liston et al., 1969; Finne and Matches, 1974), potatoes (Brocklehurst and Lund, 1982), milk (Bhadsavle et al., 1972), blown vacuum-packaged ready-to-eat roast beef meals, and beef primal cuts (Dainty et al., 1989; Kalchayanand et al., 1989; Broda et al., 1996). Clostridium perfringens (formerly known as Clostridium welchii) is a common infectious cause of outbreaks of foodborne illness in the United States, especially outbreaks in which cooked beef is the implicated source (Shandera et al., 1983; Bean and Griffin, 1990). Enterotoxigenic Clostridium perfringens has been associated with sporadic cases of diarrhoea and with some cases of sudden infant death syndrome (Lindsay et al., 1993; Murell et al., 1993; Mpamugo et al., 1995). In addition, Clostridium perfringens is the most important species of poultry infections (Hamdy et al., 1983; Brennan et al., 2003; Lovland et al., 2004; Thompson et al., 2006; Keyburn et al., 2008; Cooper and Songer, 2009). Clostridium botulinum causes severe food poisoning from botulinum neurotoxin production in the food (Lund and Peck, 2000). This pathogen produces the most potent natural toxin, the human lethal dose of type A toxin is approximately 1 μg per kg (Marks, 2004). Most human diseases are caused by types A, B, and E. Botulinum toxins A and B are often associated with home food preparation (Shapiro et al., 1998), home canning (Horwitz et al., 1975), and pickling (CDC, 2000a). The possible survival of its endospores after cooking and the ability of group II strains (non-proteolytic and psychrotrophic) to grow at refrigeration temperatures are the main hazards in refrigerated processed foods of extended durability (Peck, 1997; Gould, 1999; Carlin et al., 2000). Several studies have shown that bakery products are suitable substrates for the growth of Clostridium botulinum (Daifas et al., 1999a, 1999b; Daifas et al., 2004).

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A typical nine stage cows-to-consumers supply chain was examined, which accurately reflected a single milk-processing facility. The release of botulinum toxin was assumed to have occurred either at a holding tank at the dairy farm, in a tanker truck transporting milk from the farm to the processing plant, or at a raw milk silo at the plant. By the use of this model, it was predicted that 100,000 individuals could be poisoned with more than 1 g of toxin, and 10 g would affect about 568,000 milk consumers (Wein and Liu, 2005).

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Escherichia coli The bacteria constituting the species Escherichia coli are commonly found in the intestinal microbiota of man and animals. Not until late 1950s, they were recognized as non-pathogenic normal co-habitants (Olsvik et al., 1991). On the basis on their distinct virulence properties and the clinical symptoms of the host, pathogenic Escherichia coli strains have been broadly classified into two major categories: the enteric pathogens and the extra-intestinal pathogens. Enteric pathogenic Escherichia coli have been broadly divided into diffusely adherent Escherichia coli (DAEC), enteroaggregative Escherichia coli (EAEC), enteroinvasive Escherichia coli (EIEC), enteropathogenic Escherichia coli (EPEC), enterotoxigenic Escherichia coli (ETEC), and Shiga toxin-producing Escherichia coli (STEC) (Levine, 1987; Nataro and Kaper, 1998). The enteric pathogens have been implicated in various forms of diarrhoea. A common cause of diarrhoea in the third world countries is EPEC. The organisms are usually transmitted by contaminated food and colonize the small intestine where they attach tightly to the epithelial cells of the villus tips (Kaper, 1994). Nataro and Kapper (1998) reported ETEC as a major cause of diarrhoea in young children from developing countries. Faecal contamination of food and drinking water is the major route of infection of these pathogens for humans (Kuhnert et al., 2000). Shiga toxin-producing Escherichia coli or Verotoxin-producing Escherichia coli causes a broad range of symptoms in humans including haemorrhagic colitis and haemorrhagic uraemic syndromes (Griffin, 1999). Cattle is the main reservoir of STEC and faecal contamination of food represents the usual source of infection for humans, however, human to human transmission has also been observed in outbreaks (Kuhnert et al., 2000). Enteroinvasive Escherichia coli closely resemble Shigella and cause mainly watery diarrhoea and dysentery in severe cases. Enteroaggregative

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Escherichia coli causes a type of diarrhoea which persists often for more than 14 days (Nataro et al., 1998). Escherichia coli O157:H7 was first recognized as a pathogen as a result of an outbreak of unusual gastrointestinal illness in 1982 (Riley et al., 1983). Among the various diarrhoeagenic serotypes of Escherichia coli, enterohaemorrhagic Escherichia coli O157:H7 is implicated in large number of foodborne outbreaks in many parts of the world including developed nations (Mead et al., 1999). In 2002, 28 cases of Escherichia coli O157:H7 illnesses were linked to contaminated ground beef, and approximately 19 million pounds of raw ground beef was recalled (CDC, 2002). A major source of infection is undercooked ground beef, other sources include consumption of unpasteurized milk and juice, raw sprouts, lettuce, and salami, and contact with infected live animals. This pathogen is especially associated with comminuted beef products such as burgers in the United States and other foods including beef jerky, beansprouts, unpasteurised milk, apple ciders, and salad vegetables (Wong et al., 2009). Outbreaks have occurred from exposure to various Escherichia coli-tainted food items including alfafa (Ferguson et al., 2005), apple cider (Hilborn et al., 2000), unpasteurized gouda cheese (Honish et al., 2005), lettuce (Ackers et al., 1998), raw milk (Keene et al., 1997), contaminated pasteurized milk (Goh et al., 2002), parsley, sprouts, (Naimi et al., 2003), radish (Michino et al., 1999), and salami (MacDonald et al., 2004) as well as through petting zoos (David et al., 2004) and environmental transmission (Varma et al., 2003; Grif et al., 2005).

Listeria monocytogenes Listeria monocytogenes is among the most important pathogens that caused a significant number of outbreaks in ready-to-eat meat products (CDC, 1998; CDC, 2000c; Janes et al., 2002). The cost of acute illness from foodborne Listeria monocytogenes alone is $2.3 billion in the United States (Economic Research Service, United State Department of Agriculture (ERS/USDA); CDC, 2002). The organism can survive under extreme physicochemical conditions such as refrigeration temperatures, low pH, high salt concentration, and high temperatures (Vasseur et al., 1999; Lou and Yousef, 1999; Jay, 2000). These characteristics make it difficult to control this pathogen in the food industry (Lin et al., 2004). Listeria monocytogenes is often found in silage, water, and the environment of animal fodder (Weis and Seeliger, 1975), soft cheese (Zottola

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and Smith, 1991; Uyttendaele et al., 1999; Danielsson-Tham et al., 2004), raw or contaminated milk (Yoshida et al., 1998), contaminated refrigerated foods (Fernandez et al., 1997; Razavilar and Genigeorgis, 1998; Tham et al., 2000), and vegetables (Arumugaswamy et al., 1994). Most reports associated listeriosis with the consumption of contaminated ready-to-eat foods such as dairy products, processed or cured meat and poultry, salads, seafood, and uncooked eggs (Garcia et al., 2004). Pork meat products have been implicated in a number of listeriosis outbreaks (Frye et al., 2002; Mayrhofer et al., 2004). There have been a large number of recalls of ready-to-eat meat such as chicken, turkey, and beef due to the contamination by Listeria monocytogenes (Kathariou, 2000; Food Safety and Inspection Service, United State Dept. of Agriculture (FSIS/USDA), 2005). Foods can become contaminated with Listeria monocytogenes through cross-contamination during processing. Ready-to-eat cooked meats are frequently contaminated with Listeria monocytogenes during post processing steps (Beresford et al., 2001). Listeriosis has a 20-30% mortality rate which makes it vital to control in food sources (Farber and Peterkin, 1991; Datta, 2003). The infection can result in meningo-encephalitis and septicaemia in neonates and adults, fever and abortion in pregnant women (Vázquez-Boland et al., 2001). The newborn (McLauchlin, 1990), the elderly (Bula et al., 1995), and the immunocompromised (Rivero et al., 2003) hosts are at greatest risk for serious illness. The organism can form biofilms on floor drains, storage tanks, hand trucks, conveyor belts and other food-contact materials (Mafu et al., 1990; Kim and Frank, 1995).

Salmonella spp. Salmonella spp. are facultative, intracellular parasites that invade the mucous membrane and are transmitted to humans mainly through contaminated food products (D’Aoust, 1991; International Commission on Microbiological Specifications for Food (ICMSF), 1996). Gastrointestinal infections by Salmonella are one of the leading bacterial foodborne diseases (Park and Diez-Gonzalez, 2003). Salmonella spp. is one of the major pathogens transmitted via food ingestion, causing gastroenteritis, diarrhoea, vomiting, abdominal cramping, enteric fever, septicaemia, and in severe cases, death (Novotny et al., 2004). The incidence of salmonellosis appears to be rising both in the United States and in other industrialized nations (United States Food and Drug Administration (USFDA), 2006). Meat-producing

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animals are often regarded as important reservoirs of Salmonella (Wray and Davies, 2003). This pathogen is a common contaminant of raw pork (Escartin et al., 2000; Jordan et al., 2006; Prendergast et al., 2008) and can be hazardous to consumers if the meat is not thoroughly cooked. In addition, Salmonella spp. has been implicated in outbreaks of foodborne illness linked to the consumption of contaminated vegetables, including lettuce (Gillespie, 2004), tomatoes (CDC, 2007), contaminated minced meat (Korsak et al., 2003), ground beef, dairy products and fresh produce fertilized with cattle manure (Park and Diez-Gonzalez, 2003). Salmonella Enteritidis are considered to be the most important group of foodborne Salmonella causing gastrointestinal illness of varying severity in humans (Forshell and Wierup, 2006). Previous investigations identified Salmonella Enteritidis contaminated shell eggs as the major vehicle for infection in humans (Braden, 2006). Salmonella Typhimurium is of major concern to public health and represents one of the most important serovars implicated in the Salmonella gastroenteritis outbreaks throughout the world (Ray, 2001). It is the predominant serotype isolated from humans in Europe. Pigs are important reservoir of this particular serotype (Jordan et al., 2006; Foley et al., 2007; Boyen et al., 2008; Prendergast et al., 2008; Prendergast et al., 2009). Prevention of Salmonella Typhimurium infection in pigs has increasingly become a priority in public health concerns (Abrahantes et al., 2009). Adhesion of Salmonella to food surfaces was the first published report on foodborne bacterial biofilm (Duguid et al., 1966). Joseph et al. (2001) reported the ability of Salmonella spp. to form biofilm on three commonly-used food contact surfaces such as plastic, cement, and stainless steel. Attachment of the pathogens to chicken skin (Campbell et al., 1987) and food-contact surfaces (Shi and Zhu, 2009) was documented. This can lead to potential hygienic problems because pathogenic biofilms provide a reservoir of contamination. Bacterial cells present in biofilms on slaughtering plant surfaces due to inadequate cleaning may resist the effects of commercial sanitizers (Taormina and Beuchat, 2002; Stopforth et al., 2003a, 2003b; Gram et al., 2007; Taormina and Dorsa, 2007).

Shigella spp. Shigella spp. is a group of Gram-negative enteric bacilli that causes acute bacillary dysentery in humans (Bennish, 1991). They are classically known as

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water-borne pathogen, however, they can also be a significant cause of foodborne disease (June et al., 1993). Shigella is acid resistant, salt tolerant, and can survive at infective levels in many types of foods such as fruits and vegetables, low pH foods, prepared foods, and foods held in modified atmosphere or vacuum packaging (Smith, 1987). Shigella spp. have been isolated from food products such as salads (Lew et al., 1991; Rafii and Lundsford, 1997; Warren et al., 2007), ground beef (Warren et al., 2007), bean dip (CDC, 2000b), raw oysters (Reeve et al., 1989; Terajima et al., 2004), and vegetables (Martin et al., 1986; Davis et al., 1988; Public Health Laboratory Service (PHLS), 1997; CDC, 1999). The contamination can cause outbreaks associated with food, water, and milk. In addition, shigellosis has been associated with recreational swimming (Iwamoto et al., 2005). The main contributing factors that led to outbreaks of foodborne shigellosis or bacillary dysentery are poor personal hygiene of food handlers and improper holding temperature of contaminated food. The infection is readily transferred from person-to-person contact and through fomites (Islam et al., 2001). Occasionally, it can be transmitted by insect vectors, primarily flies (Levine and Levine, 1991). Shigella dysenteriae causes brisk and deadly epidemics, particularly in the developing world. Shigella flexneri and Shigella sonnei are responsible for the endemic form of the diseases especially in industrialized nations (Keusch, 1997; Sansonetti, 1999). The organisms are shed for 3 to 5 weeks after symptoms cease, ultimately contributing to a greater person-to-person spread than in other enteric pathogens such as Salmonella and Vibrio cholerae.

Staphylococcus aureus Staphylococcus aureus is one of the most common Gram-positive bacteria causing food poisoning. It can excrete an exotoxin which causes staphylococcal food poisoning (Jay, 2000). Staphylococcal enterotoxins are resistant to proteolytic enzymes such as rennin, papain, and chymotrypsin but sensitive to pepsin at pH 2 (ICMSF, 1996; Balaban and Rasooly, 2000; Jay, 2000). These toxins are produced during phases of growth, mainly during the middle and at the end of the exponential phase. Staphylococcal gastroenteritis is caused by ingestion of enterotoxins produced by some staphylococcal strains. Foods containing the enterotoxin usually appear and taste normal. In processed foods where Staphylococcus aureus should have been destroyed by processing, the reappearance of the

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bacterium can cause damages to food. Several studies were reported where Staphylococcus aureus was isolated from a range of food materials (Aycicek et al., 2005; Normanno et al., 2005; Normanno et al., 2007; Dewaal and Bhuiya, 2007; Schmid et al., 2007; Ifesan et al., 2009), while both animal and human have been suggested as sources of contamination. Cross-contamination, infected food handlers, and inappropriate storage temperatures have been reported as the contributory faults to staphylococcal foodborne outbreaks. Minor outbreaks of staphylococcal food poisoning are not usually reported and true incidence is probably underestimated (Dinges et al., 2000). Nevertheless, staphylococcal food poisoning represents a social burden considering hospital expenses, loss of patients’ working days, together with the cost of disposing the contaminated food (Normanno et al., 2005). Methicillin-resistant Staphylococcus aureus (MRSA) strains have been reported in major food animals. This was attributed to the extended use and misuse of antibiotics in animal husbandry (Lee, 2003; Kitai et al., 2005; Normanno et al., 2007; Pesavento et al., 2007; Schmid et al., 2007; Ifesan et al., 2009b). In the analysis of 1,913 specimens from milk, beef, pork and chicken meat, 15 strains of Staphylococcus aureus harboured mecA gene were reported (Lee, 2003). The presence of MRSA in foods may demonstrate its spread into the community and signify the increasing impact of health care-associated organisms among populations previously considered to be unaffected by this antimicrobial-resistant pathogen.

Vibrio spp. Despite the efforts of the Centers for Disease Control and Prevention there has been an estimated 126% increase in the incidence of vibrio-associated infections in the United States between 1996 and 2002 (CDC, 2003). Vibrio parahaemolyticus is a halophilic bacterium that causes acute gastroenteritis in humans. The organism inhabits seawater, and has been frequently isolated from fish, clams, and crustaceans (Wong et al., 1992). The major clinical symptoms of human gastroenteritis caused by Vibrio parahaemolyticus are characterized by diarrhoea, headache, vomiting, nausea, abdominal cramps and low fever (Su and Liu, 2007). Foodborne Vibrio parahaemolyticus infections occur commonly in the summer. Food poisoning caused by this pathogen is generally associated with

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the consumption of raw or undercooked seafood. Consumption of raw or undercooked seafood contaminated with Vibrio parahaemolyticus may lead to development of acute gastroenteritis. Food poisoning outbreaks associated with Vibrio parahaemolyticus have been reported throughout the world, especially in areas like Taiwan and Japan, where people often consume raw and semi-processed seafood in their daily diet (Honda and Iida, 1993; Mahmud et al., 2006). In addition, this pathogen is recognized as the leading cause of human gastroenteritis associated with seafood consumption in the United States (Su and Liu, 2007). Recent works suggest that the ability of Vibrio parahaemolyticus to survive and proliferate in its environmental niches, in shellfish, and in the human intestine may have resulted from the acquisition of regions encoding novel traits which are differentially regulated in different niches (GonzalezEscalona et al., 2005; McLaughlin et al., 2005; Fuenzalida et al., 2006). Vibrio cholerae is reported to be a natural component of various aquatic ecosystems (Islam et al., 1994). Vibrio cholerae is the causative agent of cholera, an acute dehydrating diarrhoea that occurs in epidemic and pandemic forms (Kaper et al., 1995; Faruque et al., 1998). Disease outbreaks in marine organisms appear to be escalating worldwide (Harvell et al., 2002). A growing number of human bacterial infections have been associated with recreational and commercial uses of marine resources (Tamplin et al., 1990). However, in light of heightened human dependence on marine environments for fisheries, aquaculture, waste disposal, and recreation, the potential for pathogen emergence from ocean ecosystems remains a cause for concern (Bahlaoui et al., 1997; Kirn et al., 2005). Seafood harvested from waters contaminated with pathogenic Vibrio cholerae can act as reservoirs and may spread the disease, thus they are of potential public health significance.

Yersinia enterocolitica Yersinia enterocolitica encompasses a spectrum of phenotypic and genotypic variants, of which only a few have been conclusively associated with human or animal disease (Mollaret et al., 1979). There is strong indirect evidence that food, especially pork products, and water are important sources of human infection (Tauxe et al., 1987; Scheimann, 1989; Blumberg et al., 1991; Kapperud, 1991).

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Yersinia enterocolitica is a common human pathogen which causes gastrointestinal syndromes of various severities, ranging from mild diarrhoea to mesenteric adenitis evoking appendicitis. Systemic involvement is unusual, but arthritis and erythema nodosum are common complications (Cornelis et al., 1989). Infections were more frequent for young children and infants than for other persons (CDC, 2004; Koehler et al., 2006). The presence of Yersinia enterocolitica has been demonstrated in fresh produce in various countries. In Italy, Cavazzini et al. (1982) isolated this bacterium from many horticultural products. Lee et al. (2004) reported 4% Yersinia spp. contamination of ready-to-eat vegetables in Korea. In Norway, Johannessen et al. (2002) detected Yersinia enterocolitica in 3% of lettuce. In Australia, Szabo et al. (2000) isolated Yersinia enterocolitica from minimally processed lettuce. An outbreak of food poisoning caused by salads contaminated with Yersinia enterocolitica was reported in Japan (Sakai et al., 2005). Epidemiologic data show that those infected with Yersinia enterocolitica have a history of exposure to raw pork (Ostroff et al., 1994; Abdel-Haq et al., 2000; Johannessen et al., 2000; Korte et al., 2004; Bhaduri et al., 2005; FredrikssonAhomaa et al., 2006; Kuehni-Boghenbor et al., 2006; Fredriksson-Ahomaa et al., 2007; Lambertz et al., 2007; Hudson et al., 2008), untreated drinking water (Ostroff et al., 1994; Ackers et al., 2000), and dairy products (Ackers et al., 2000).

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Chapter 5

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NATURAL PRODUCTS AS ANTIOXIDANTS IN FOODS Historical records indicate that herbs and spices were used for flavouring, food preservation, and medicinal purposes in ancient times, yet it is uncertain how herbs and spices first became incorporated into food preparation and how widespread their usage was in food and medicine until recent decades. Although spices are well-known for their medicinal, preservative, and antioxidant properties, they have been used with primary purpose of enhancing the flavour of foods rather than extending their shelf life (Tassou et al., 2000). Spices and herbs are valued for their distinctive flavours, colours, and aromas and are among the most versatile and widely used ingredient in food preparation and food processing throughout the world. Due to the economical impacts of food spoilage and contamination, and the consumers’ concerns over the safety of foods containing synthetic chemicals. A lot of attention has been paid to naturally-derived compounds or natural products (Shelef, 1983; Hsieh et al., 2001; Alzoreky and Nakahara, 2003; Burt, 2004; Owen and Palombo, 2007; Voravuthikunchai, 2007; Del Nobile et al., 2009; Ifesan et al., 2009a, 2009c). Herbs and spices are regarded as natural alternatives for chemical preservatives and their uses in foods meet the demands of consumers for mildly processed or natural products (Nychas, 1995). Countries with hot climate use multiple spices on a regular basis, compared with countries with cooler climate. The obvious reason for this being that foods in warmer zones are more susceptible to spoilage than foods in cooler areas. Addition of many spices produced synergistic effect together with displayed increased antibacterial activity when used in combination than when used alone (Billing and Sherman, 1998).

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Spices and herbs which possess antimicrobial activity include those containing simple phenols and phenolic acids (Dorman and Deans, 2000; Bergonzelli et al., 2003; Burt, 2004), alkaloids coumarins, and terpenoids (Cowan, 1999; Bergonzelli et al., 2003). Those which demonstrated antimicrobial activities were incorporated into food preparation for their antimicrobial properties rather than for purely organoleptic purposes (Billing and Sherman, 1998). The antimicrobial action of plant extracts (Mau et al., 2001; Ahn et al., 2004; Sallam et al., 2004; Kapoor et al., 2008; Park et al., 2008; Ifesan et al., 2009b) or their essential oils (Koutsoumanis et al., 1998; Skandamis and Nychas, 2000; Tsigarida et al., 2000; Burt, 2004; Fisher and Phillips, 2006; Raybaudi-Massilia et al., 2006; Gündüz et al., 2009; Gutierrez et al., 2009) in model food systems or in real food is well-documented in the literature. Extracts from bay (Smith-Palmer et al., 2001), clove (Menon and Garg, 2001; Mytle et al., 2006), oregano (Tsigarida et al., 2000; Mejlholm and Dalgaard, 2002; Giatrakou et al., 2008), rosemary (Sebranek et al., 2005; Theivendran et al., 2006), sage (Ahmed and Abd El-Rahman, 2002; Ayar et al., 2004; Hayouni et al., 2008), and thyme (Harpaz et al., 2003; Singh et al., 2003; Solomakos et al., 2008) are some of the natural additives that have been used to improve the sensory characteristics as well as extend the shelf life of foods.

LIPID OXIDATION IN MEAT AND MEAT PRODUCTS The growing interest in convenience foods is making ready-to-eat meat products become more desirable and well-known. There is increasing consumers’ demand for high quality meat products that are easy to prepare, nutritious, and taste good. As a result, the food industry has drastically increased the production of ready-to-cook and ready-to-eat meat products to be marketed at supermarkets or retail stores. Meat products typically spoil due to one or the two major causes, either microbial growth or chemical deterioration. Several processed meat products are particularly susceptible to oxidative rancidity due to exposure to oxygen and, or elevated temperatures during processing. Precooked meat, especially pork is susceptible to lipid oxidation, compared to those of beef and sheep (Kanner, 1994; Van Laack, 1994; Channon and Trout, 2002; Jayathilakan et al., 2007) due to its relatively high content of unsaturated fatty acids (Enser et al., 1996). In addition, the warmed over flavour develops within few hours when cooked meat is stored at 4°C

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(Tims and Watts, 1958), and frequently with microbial contamination (Delaquis et al., 1999). Oxidation of lipids, which occurs during storage, processing, and heat treatment, is one of the basic processes causing rancidity in products (Hudson, 1990), leading to their oxidative deterioration. Hydroperoxides as well as their products of decomposition are potentially reactive substances that can cause deterioration of food proteins and amino acids (Gardner, 1979). Oxidative rancidity in meat can vary greatly, ranging from extensive flavour changes, colour loss, and structural damage to proteins (Xiong, 1996) to a more subtle, loss of freshness that discourages repeated purchases by consumers. Karpinska et al. (2001) reported that products of lipid oxidation can cause pathological changes in the mucous membrane of the alimentary tract, inhibit activity of enzymes, and increase the content of cholesterol and peroxides in blood serum, thus activate the process of atherosclerosis. Furthermore, there have been some evidences that lipid oxidation products are commonly associated with aging, membrane damage, heart disease, and cancer (Ames, 1983; Cosgrove et al., 1987; Jacob, 1995). Therefore, there is a need to prevent lipid oxidation in meat and meat products. Application of antioxidants is one approach to reduce fat oxidation (Frankel, 1993; Karpinska et al., 2001).

SYNTHETIC ANTIOXIDANTS The use of chemicals to enhance food safety is of great interest to the food industry. Synthetic antioxidants, such as BHA, BHT, and TBHQ, are widely used in the food industry (Duh and Yen, 1997). However, there are concerns for the synthetic antioxidants by some human health professionals and consumers (Decker and Mei, 1996). While TBHQ is banned in Japan and certain European countries (Shahidi, 1997), BHA and BHT have been reported to be carcinogenic (Ito et al., 1982). It has been demonstrated that BHT may cause internal and external haemorrhaging at high doses which could cause deaths in some strains of mice and guinea pigs (Shahidi and Wanasundara, 1992).

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ALTERNATIVE ANTIOXIDANTS FROM NATURAL PRODUCTS Natural antioxidants are readily acceptable by the consumers. They are considered to be safe. Unlike the synthetic chemical antioxidant, antioxidants from natural sources are identical to the food that people eat regularly or mixed with food. They do not only stabilize the edible oils but also add to the nutraceutical value of the oil (Pokorny, 1991). Due to health problems associated with synthethic antioxidants, many food processors and consumers have been seeking alternative antioxidants. Extensive consumption of meat products with the need for safer and more effective preservatives has prompted investigators to seek natural preservatives of plant origin that could provide greater product safety to consumers. In addition, there has been a growing interest in natural ingredients because they have greater applications for increasing consumers’ acceptability, palatability, stability, and shelf life of food products (Naveena et al., 2008). The use of natural preservatives to improve the shelf life of meat products is a promising technology as many herbs, spices and their essential oils have demonstrated both antioxidant (Rey et al., 2005; Bañón et al., 2007; Carpenter et al., 2007; Jayathilakan et al., 2007; Juntachote et al., 2007; Naveena et al., 2008; Ifesan et al., 2009c, 2009d) and antimicrobial (Ahn et al., 2004; Gutierrez et al., 2008; Solomakos et al., 2008; Gutierrez et al., 2009; Ifesan et al., 2009a, 2009c) properties.

NATURAL ADDITIVES AS ANTIOXIDANTS IN MEAT AND MEAT PRODUCTS Substantial data exists in favour of use of polyphenols from green tea (Nissen et al., 2004; Bozkurt, 2006; Theivendran et al., 2006; Bañón et al., 2007), grape seed extract (Ahn et al., 2004; Pazos et al., 2004; Mielnik et al., 2006; Bañón et al., 2007; Carpenter et al., 2007; Sasse et al., 2009), oregano (Bhale et al., 2007; Giatrakou et al., 2008; Sasse et al., 2009), rosemary (McCarthy et al., 2001; Yu et al., 2002; Formanek et al., 2003; Ahn et al., 2004; Nissen et al., 2004; Estevez et al., 2005; Sebranek et al., 2005; Estevez et al., 2006; Fan et al., 2006; Rižnar et al., 2006; Bhale et al., 2007; Akarpat et al., 2008; Sasse et al., 2009), sage (McCarthy et al., 2001; Estevez et al., 2006), and tea catechins (McCarthy et al., 2001; Tang et al., 2002; Mitsumoto et al., 2005) as natural antioxidants in meat and meat products. There have

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been some reports on the use of plant extracts on a wide range of food products including cinnamon (Badei et al., 2002; Jayathilakan et al., 2007), garam masala spices (Vasavada et al., 2006), garlic and organosulfur compounds (Wong and Kitts, 2002; Yin and Cheng, 2003; Sallam et al., 2004), galangal (Juntachote et al., 2007), ginger and cucumis (Garg and Mendiratta, 2006), onion (Tang and Cronin, 2007), peppers (Karwowska and Dolatowski, 2007; Sun et al., 2007) and pomegranate (Naveena et al., 2008). Green tea extract, and Thymbra spicata oil decreased thiobarbituric acidreactive substances (TBARS) formation more than BHT in sucuk-Turkish dryfermented sausage (Bozkurt, 2006). It has been demonstrated that rosemary extract was more effective than BHA/BHT in preventing increased TBARS values or loss of red colour in raw frozen sausage (Beltran et al. 2004; Sebranek et al., 2005). Similarly, Naveena et al. (2008) reported that addition of pomegranate rind powder at a level of 10 mg equivalent phenolics per 100 g meat was sufficient to protect chicken patties against oxidative rancidity for periods longer than BHT.

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CONTRIBUTION OF NATURAL ADDITIVES AS COLOUR ENHANCER IN MEAT Colour is an important visual cue involved in consumers’ perception of acceptable meat quality (Faustman and Cassens, 1990) and attractive food colour could result in increased consumption. In addition to antioxidant activities demonstrated in meat by natural extract or their essential oils, the ability of some of them to improve the meat colour has been reported. Yu et al. (2002) reported that rosemary extracts improved the colour stability of cooked turkey rolls. Formanek et al. (2003) studied rosemary extracts in irradiated ground beef and found that colour change was inhibited by the addition of rosemary. Lawrence et al. (2004) observed improved colour stability as a result of rosemary extracts injected into beef loins. Improved colour properties have been reported with ostrich meat preserved with rosemary, an extract which is rich in phenolic compounds (Seydim et al., 2006). The ability of beetroot extract (Rey et al., 2005), and grape seed extract (Ahn et al., 2004; Carpenter et al., 2007) to increase meat colour in cooked pork patties were demonstrated. Pepper extracts increased redness of meat samples, compared to the control (Karwowska and Dolatowski, 2007). Similar observations were made when cooked beef was treated with pine bark extract (Ahn et al., 2004),

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low sulphite beef patties mixed with green tea extract (Bañón et al., 2007), and cooked pork with Eleuterine americana extract (Ifesan et al., 2009c). Relationship between colour stability with lipid oxidation and natural pigment was established (Jakobson and Bertelsen, 2000; Mancini and Hunt, 2005). The various extracts and the colour stability might be caused by phenolic acid compounds related to oxidation (Mazza and Miniati, 1993). A possible explanation for the observed meat colour stability after extracts or essential oil treatment may be due to high potential redox values that could preserve heme pigments at a reduced form (Karwowska and Dolatowski, 2007). In other contexts, the retention of the redness of meat was related to the amount of anthocyanins present in the extracts as some of the extracts possess natural red colour (Ahn et al., 2004; Carpenter et al., 2007; Ifesan et al., 2009c). The red colour imparted to the meat by beetroot is due to its high content in β-cyanins and β-xanthins (Elbe et al., 1974; Rey et al., 2005). Highpigment red phenotypes are most capable of inhibiting metmyoglobin-H2O2mediated oxidation (Wettasingle et al., 2002). The increase in colour was not perceived as negative by the sensory panels with respect to overall product quality (Bañón et al., 2007; Carpenter et al., 2007; Ifesan et al., 2009c).

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NATURAL ANTIOXIDANTS IN OIL Dechlorophyllized green tea extract exhibited antioxidant activity in equivalent or slightly higher than those of BHA and BHT in sealed blubber oil and menhaden oil. Apart from being an effective antioxidant, the extract did not impart any visible colour or perceivable odour change in the treated oils (Wanasundara and Shahidi, 1998). Higher antioxidant activity of rosemary extract in stabilizing peanut oil was found at 4% of the extract level, compared to sage and sumac extracts. However, considering the blends, the most effective ones were sage and sumac combinations (Ozcan, 2003). Antioxidant activity of methanolic extract of sesame cake was evaluated in soybean, sunflower, and safflower oils. The results showed that sesame cake extract at concentrations of 5 to 100 ppm in vegetable oils could significantly lower peroxide, diene, and p-anisidine values of oils during storage at 60°C. Moreover, sesame cake extract demonstrated antioxidant effectiveness better than BHT at 200 ppm (Suja et al., 2004). Sullivan et al. (2005) reported lower level of lipid oxidation in the oil from livers of white pollock and cod mixed with rosemary and tea catechins. The antioxidant activities of acetone, hexane, and methanol extracts from oat groat

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were investigated. Oat extracts at one to 10 milligram presented significantly greater capability in preventing cholesterol oxidation than the control during heating (Sun et al., 2006). Capabilities of methanol extracts from oregano and rosemary in retarding oxidation of long-chain polyunsaturated fatty acids, docosahexaenoic acid, and eicosapentaenoic acid in menhaden oil were investigated. Rosemary extract demonstrated higher 2,2-diphenyl-1picrylhydrazyl (DPPH) free radical scavenging capability than oregano extract (Bhale et al., 2007). The antioxidant efficiencies of rosemary and oregano were reported to be the same as the mixture of synthetic antioxidants, BHT and BHA, in reducing oxidation of soybean oil at 63°C over a seven day period (Almeida-Doria and Regitano-Darce, 2000).

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NATURAL ADDITIVES AS ANTIOXIDANTS IN CONFECTIONERIES Spices including cardamom fruits, cinnamon bark, clove bud powders, and volatile oils were applied as antioxidant agents to improve flavour and prevent rancidity in cookies. Reported data indicated that the threshold level of cardamom and cinnamon powder in cookies was 1% while that of clove powder was 0.5%. In addition, the threshold level of the volatile oils of cardamom and cinnamon was 0.05% while that of clove volatile oil was 0.075% (Badei et al., 2002). The additives of basil, oregano, and paprika on the properties of bread supplemented with flax seeds were evaluated for lipid hydrolysis and oxidation. The breads were made from wheat flour with 5% flax seeds and simultaneous addition of 1% of frozen herbs including oregano or basil or 5% dried red paprika fruits. It was shown that additions of herbs and paprika generally improved quality of bread, with oregano increased the tastiness, volume of bread, and elasticity of crumb (Rotkiewicz et al., 2007).

PROPOSED MECHANISMS OF ACTION OF NATURAL ANTIOXIDANTS Phospholipids are the primary substrates of lipid oxidation and the membrane phospholipids which are high in polyunsaturated fatty acids are responsible for the initial development of oxidation in cooked meat products during storage (Gray and Pearson, 1987). Natural antioxidants are believed to

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break free radical chains of oxidation by donation of hydrogen from the phenolic groups, thereby forming a stable end product (Sherwin, 1978). Polyphenolic compounds are primarily responsible for the antioxidant activity of natural extracts (Cuppett, 2001). Flavonoids are the most abundant and potent group of plant phenolic compounds that possess antioxidant, anticarcinogenic, anti-inflammatory, and antimicrobial activities (Rice-Evans and Miller, 1996; A’Herne and O’Brien, 1999; Friedman and Jurgens, 2000). They demonstrated antioxidant activity as metal chelator or free-radical scavenging activities (Ross and Kasum, 2002). Rosemary and its extract contain high levels of phenolic compounds such as carnosol and rosemarinic acid which exhibited very potent antioxidant activity (Wu et al., 1982; Inatani et al., 1983). Furthermore, antioxidant efficiency of rosemary extracts is due to high content of phenolic compounds which include monoterpenes (eteric olis), diterpene phenols (carnosic acid, carnosol, rosmanol, epirosmanol, isorosmanol, methyl carnosate), phenolic acids (rosmarinic acid), flavonols, and triterpene acids (ursolic acid, oleanolic acid, butilinic acid) (Leung and Foster, 1996). The inhibitory effects of watersoluble sage extracts on lipid peroxidation in cooked turkey products was attributed to the free radical scavenging and transition metal chelating activities of sage water extract (Huang et al., 1996; Lu and Foo, 2002). Antioxidant activity of pepper is based on the presence of specific alkaloidscapsaicinoids compounds (Lee at al., 1995; Kogure et al., 2002). We have demonstreated the ability of the extract of Eleutherine americana to act as an antioxidant in cooked pork. The activity is attributed to several naphthoquinones such as elecanacin, eleutherine, isoeleutherine eleutherinoside A, eleuthoside B, and naphthols or anthraquinone (Zhengxiong et al., 1984; Hara et al., 1997; Qui et al., 2005; Xu et al., 2006; Paramapojn et al., 2008; Ifesan et al., 2009b). These compounds possess OH groups which are likely to be responsible for its ability to retard lipid oxidation by scavenging free radicals as evidenced by DPPH and hydroxyl radical activities (Ifesan et al., 2009c).

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Singh, A., Singh, R.K., Bhunia, A.K. and Singh, N. 2003. Efficacy of plant essential oils as antimicrobial agents against Listeria monocytogenes in hotdogs. Lebensm.-Wiss. u.-Technol. 36: 787-794. Skandamis, P.N. and Nychas, G.-J.E. 2000. Development and evaluation of a model predicting the survival of Escherichia coli O157:H7 NCTC 12900 in homemade eggplant salad at various temperatures, pHs and oregano essential oil concentrations. Appl. Environ. Microbiol. 66: 1646-1653. Smith-Palmer, A., Stewart, J. and Fyfe, L. 2001. The potential application of plant essential oils as natural food preservatives in soft cheese. Food Microbiol. 18: 463-470. Solomakos, N., Govaris, A., Koidis, P. and Botsoglou, N. 2008. The antimicrobial effect of thyme essential oil, nisin, and their combination against Listeria monocytogenes in minced beef during refrigerated storage. Food Microbiol. 25: 120-127. Suja, K.P., Abraham, J.T., Thamizh, S.N., Jayalekshmy, A. and Arumughan, C. 2004. Antioxidant efficacy of sesame cake extract in vegetable oil protection. Food Chem. 84: 393-400. Sullivan, A.O., Mayr, A., Shaw, N.B., Murphy, S.C. and Kerry, J.P. 2005. Use of natural antioxidants to stabilize fish oil systems. J. Aquat. Food Prod. Tech. 14: 75-94. Sun, T., Xu, Z., Godber, J.S. and Prinyawiwatkul, W. 2006. Capabilities of oat extracts in inhibiting cholesterol and long chain fatty acid oxidation during heating. Cereal Chem. 83: 451-454. Sun, T., Xu, Z., Wu, C.T., Janes, M., Prinyawiwatkul, W. and No, H.K. 2007. Antioxidant activities of different colored sweet bell peppers (Capsicum annuum L.). J. Food Sci. 72: S98-S102. Tang, S., Kerry, J.P., Buckley, D.J. and Morrissey, P.A. 2002. Antioxidative effect of added tea catechins on susceptibility of cooked red meat, poultry and fish patties to lipid oxidation. Food Res. Int. 34: 651-657. Tang, X. and Cronin, D.A. 2007. The effects of brined onion extracts on lipid oxidation and sensory quality in refrigerated cooked turkey breast rolls during storage. Food Chem. 100: 712-718. Tassou, C.C., Drosinos, E.H. and Nychas, G.-J.E. 1995. Effects of essential oil from mint (Mentha piperita) on Salmonella enteritidis and Listeria monocytogenes in model food systems at 4° and 10°C. J. Appl. Bacteriol. 78: 593-600. Tassou, C.C., Koutsoumanis, K. and Nychas, G.-J.E. 2000. Inhibition of Salmonella enteridis and Staphylococcus aureus on nutrient both by mint essential oil. Food Res. Int. 33: 273-280.

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Theivendran, S., Hettiarachchy, N.S. and Johnson, M.G. 2006. Inhibition of Listeria monocytogenes by nisin combined with grape seed extract or green tea extract in soy protein film coated on Turkey frankfurters. J. Food Sci. 71: M39-M44. Tims, M.J. and Watts, B.M. 1958. Protection of cooked meat with phosphates. Food Techol. 12: 240-243. Tsigarida, E., Skandamis, P. and Nychas, G.-J.E. 2000. Behaviour of Listeria monocytogenes and autochthonous flora on meat stored under aerobic, vacuum and modified atmosphere packaging conditions with or without the presence of oregano essential oil at 5°C. J. Appl. Microbiol. 89: 901909. Van Laack, R.L.J.M. 1994. Spoilage and preservation of muscle foods. In: Kinsman D.M., Kotula, A.W. and Breidenstein, B.C. eds., Muscle Foods. Chapman and Hall, New York, pp. 378-405. Vasavada, M.N., Dwivedi, S. and Cornforth, D. 2006. Evaluation of garam masala spices and phosphates as antioxidants in cooked ground beef. J. Food Sci. 71: C292-C297. Voravuthikunchai, S.P. 2007. Family Zingiberaceae compounds as functional antimicrobials, antioxidants, and antiradicals. Food 1: 227-240. Wanasundara, U.N. and Shahidi, F. 1998. Antioxidant and pro-oxidant activity of green tea extracts in marine oils. Food Chem. 63: 335-342. Wettasingle, M., Bolling, B., Plhak, L., Xiao, H. and Parkin, K. 2002. Phase II enzyme-inducing and antioxidant activities of beetroot (Beta vulgaris L.) extracts from phenotypes of different pigmentation. J. Agric. Food Chem. 50: 6704-6709. Wong, P.Y.Y. and Kitts, D.D. 2002. The effects of herbal pre-seasoning on microbial and oxidative changes in irradiated beef steaks. Food Chem. 76: 197-205. Wu, J.W., Lee, M.H., Ho, C.T. and Chang, S.S. 1982. Elucidation of the chemical structures of natural antioxidants isolated from rosemary. J. Agric. Am. Oil Chem. Soc. 59: 339-345. Xiong, Y. 1996. Impacts of oxidation on muscle protein functionality. Proc. Reciprocal Meat Conf. 49: 79-86. Xu, J., Qui, F., Duan, W., Qu, G., Wang, N. and Yao, X. 2006. New bioactive constituents from Eleutherine americana. Front Chem. China 3: 320-323. Yin, M.C. and Cheng, W.S. 2003. Antioxidant and antimicrobial effects of four garlic-derived organosulfur compounds in ground beef. Meat Sci. 63: 23-28.

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Yu, L., Scanlin, L., Wilson, J. and Schmidt, G. 2002. Rosemary extracts as inhibitors of lipid oxidation and color change in cooked turkey products during refrigerated storage. J. Food Sci. 67: 582-585. Zhengxiong, C., Huizhu, H., Chengruui, W., Yuhui, L., Jianmi, D., Sankawa, U., Noguchi, H. and Iitaka, Y. 1984. Hongconin, a new naphthalene derivative from the rhizome of Eleutherine americana (Hong-Cong). Heterocycles 22: 691-694.

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Chapter 6

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ANTIBACTERIAL ACTIVITY OF NATURAL ADDITIVES IN FOODS Researchers have recorded a huge success in the study of antimicrobial activities of plant extracts or their essential oils in vitro (Table 3). However, inhibitory effect of plant extracts or their essential oils may be hindered by a number of factors present in foods (Shelef, 1983; Tassou et al., 1995; Burt, 2004). More nutrients are available in foods compared to laboratory media and this may enable bacteria to repair damaged cells faster (Gill et al., 2002). Generally, antimicrobial activities demonstrated by herbs and spices in food systems are lower than what obtained in vitro. Greater concentration of natural antimicrobials may be needed to achieve inhibitory effects in foods, compared to what obtained in broth systems (Shelef, 1983; Smid and Gorris, 1999). At high levels of fat or protein, bacteria are protected from the action of natural antimicrobials (Aureli et al., 1992; Pandit and Shelef, 1994; Tassou et al., 1995; Mejlholm and Dalgaard, 2002; Canillac and Mourey, 2004). In addition, lower water content of food compared to laboratory media may hamper the progress of antibacterial agents to the target site in the bacterial cell (SmithPalmer et al., 2001). Nevertheless, the literature abounds on the antibacterial activities of plant extracts or their essential oils in food systems (Table 4).

CHEESE AND BUTTER The antibacterial effects of plant essential oils against Listeria monocytogenes and Escherichia coli O157:H7 were evaluated in Spanish soft cheese stored at 7°C. The oil exerted bacteriostatic effect against Listeria monocytogenes at concentration of 2,500 ppm, but was ineffective to control

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan,

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Table 3. Selected herbs and spices tested in vitro against foodborne pathogens Plant species Allium sativum L. (Garlic)

Extract Essential oil Essential oil Ethanol (0.5%) Ethanol (0.5%) Methanol Methanol Methanol Water (1:2 w/v) Water (1:2 w/v) Water (1:2 w/v) Allium tuberosum Rottl. Ethanol (10 µg/disc) (Chinese chive) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Anetholea anisata (Vickery) Ethanol Ethanol Peter G. Wilson Ethanol (Anise or Aniseed myrtle) Ethanol Ethanol Ethanol Ethanol (0.5%) Alpinia galanga (L.) Willd. Chloroform (Galangal) Chloroform Ethanol Ethanol Ethanol (80 µl/disc) Bosenbergia rotunda Chloroform (Fingerroot or Krachai) Chloroform

Bacterial species Salmonella Enteritidis Staphylococcus aureus Bacillus cereus Bacillus stearothermophilus Escherichia coli Salmonella Typhimurium Staphylococcus aureus Escherichia coli O157:H7 Listeria monocytogenes Staphylococcus aureus Bacillus subtilis Escherichia coli Listeria monocytogenes Salmonella Typhimurium Vibrio parahaemolyticus Bacillus stearothermophilus Escherichia coli Listeria monocytogenes Salmonella Enteritidis Salmonella Typhimurium Staphylococcus aureus Staphylococcus aureus Bacillus cereus Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Bacillus cereus Bacillus cereus Staphylococcus aureus

Inhibition zone or MIC 11.3 ml/l 9.3 ml/l strong inhibition strong inhibition 1.38 mg/ml 1.61 mg/ml 2.66 mg/ml >20 mm >20 mm >20 mm 11 mm 15 mm 10 mm 20 mm 14 mm 0.01% 125 µg/ml 500 µg/ml 250 µg/ml 125 µg/ml 7.8 µg/ml strong inhibition 0.78 mg/ml 0.39 mg/ml 0.325 mg/ml 0.78 mg/ml 11 mm 0.01 mg/ml 0.01 mg/ml

References Benkeblia, 2004 Benkeblia, 2004 Liu and Nakano, 1996 Liu and Nakano, 1996 Ushimaru et al., 2007 Ushimaru et al., 2007 Ushimaru et al., 2007 Siripongvutikorn et al., 2005 Siripongvutikorn et al., 2005 Siripongvutikorn et al., 2005 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Liu and Nakano, 1996 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Liu and Nakano, 1996 Voravuthikunchai et al., 2006 Voravuthikunchai et al., 2006 Oonmetta-aree et al., 2006 Mayachiew and Devahastin, 2007 Oonmetta-aree et al., 2006 Voravuthikunchai et al., 2006 Voravuthikunchai et al., 2006

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Camellia japonica L. (Camellia)

Cinnamomum burmannii (Nees & T. Nees) Blume (Malaysian cinnamon) Cinnamomum cassia (L.) Presl (Chinese cinnamon)

Cinnamomum zeylanicum Blume (Cinnamon)

Citrus aurantium subsp. bergamia (Risso) Wight & Arn. (Bergamot) Citrus limon (L.) Burm. f. (Lemon)

Methanol Methanol Methanol Methanol Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Ethanol Ethanol (0.2%) Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil

Escherichia coli O157:H7 Listeria monocytogenes Salmonella Typhimurium Staphylococcus aureus Bacillus cereus Escherichia coli Listeria monocytogenes Staphylococcus aureus Bacillus subtilis Escherichia coli Listeria monocytogenes Salmonella Typhimurium Vibrio parahaemolyticus Bacillus cereus Escherichia coli Listeria monocytogenes Staphylococcus aureus Bacillus stearothermophilus Vibrio cholerae Bacillus cereus Bacillus subtilis Escherichia coli Salmonella Typhimurium Staphylococcus aureus Bacillus cereus Campylobacter jejuni Escherichia coli O157 Listeria monocytogenes Staphylococcus aureus Bacillus cereus Campylobacter jejuni Escherichia coli O157 Listeria monocytogenes

14-19 mm 14-19 mm 14-19 mm 14-19 mm 15 mm 9 mm 12 mm 16 mm 16 mm 18 mm 15 mm 9 mm 20 mm 10 mm 5 mm 9 mm 12 mm 0.1% strong inhibition strong inhibition strong inhibition strong inhibition strong inhibition strong inhibition 0.125% v/v >4% v/v 0.5% v/v 0.125% v/v 1% v/v 1% v/v >4% v/v 1% 0.25% v/v

Kim et al., 2001 Kim et al., 2001 Kim et al., 2001 Kim et al., 2001 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006

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Table 3. (Continued) Plant species Citrus sinensis (L.) Osbeck (Sweet orange)

Cornus officinalis Siebold & Zucc. (Corni fructus)

Curcuma longa L. (Turmeric)

Cymbopogon citratus (DC.) Stapf (Lemongrass) Eleutherine americana (Aubl.) Merr. ex K. Heyne (Eleutherine)

Extract Essential oil Essential oil Essential oil Essential oil Essential oil (20 µl/disc) Essential oil (20 µl/disc) Essential oil (20 µl/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol (10 µg/disc) Ethanol Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Ethanol (80 µl/disc) Methanol Methanol Methanol Methanol Methanol Methanol Methanol Ethanol

Bacterial species Staphylococcus aureus Bacillus cereus Escherichia coli O157 Listeria monocytogenes Escherichia coli Listeria monocytogenes Staphylococcus aureus Bacillus subtilis Escherichia coli Listeria monocytogenes Salmonella Typhimurium Staphylococcus aureus Vibrio parahaemolyticus Bacillus stearothermophilus Bacillus cereus Bacillus subtilis Staphylococcus aureus Staphylococcus aureus Escherichia coli Staphylococcus aureus Vibrio cholerae Vibrio parahaemolyticus Escherichia coli Salmonella Typhimurium Staphylococcus aureus Staphylococcus aureus

Inhibition zone or MIC >4% v/v >4% v/v 1% v/v 0.25% v/v 14 mm 17 mm 18 mm 13 mm 18 mm 15 mm 17 mm 18 mm 21 mm 0.1% strong inhibition strong inhibition strong inhibition 10 mm 0.26 mg/ml 0.26 mg/ml 0.26 mg/ml 0.06-0.51 mg/ml 30.60 mg/ml 30.65 mg/ml 16.35 mg/ml 0.25 mg/ml

References Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Fisher and Phillips, 2006 Celikel and Kavas, 2008 Celikel and Kavas, 2008 Celikel and Kavas, 2008 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Mau et al., 2001 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Oonmetta-aree et al., 2006 Rojsitthisak et al., 2005 Rojsitthisak et al., 2005 Rojsitthisak et al., 2005 Rojsitthisak et al., 2005 Ushimaru et al., 2007 Ushimaru et al., 2007 Ushimaru et al., 2007 Ifesan et al., 2009b

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Eucalyptus olida L.A.S. Johnson & K.D. Hill (Strawberry gum)

Eucalyptus staigerana F. Muell. ex F.M. Bailey (Lemon iron bark)

Helichrysum italicum G. Don f. (Curry plant) Laurus nobilis L. (Bay leaf)

Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol

Escherichia coli Listeria monocytogenes Salmonella Enteritidis Salmonella Typhimurium Staphylococcus aureus Escherichia coli Listeria monocytogenes Salmonella Enteritidis Salmonella Typhimurium Staphylococcus aureus

62.5 µg/ml 500 µg/ml 125 µg/ml 125 µg/ml 15.6 µg/ml >500 µg/ml 500 µg/ml 125 µg/ml 62.5 µg/ml 62.5 µg/ml

Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006

Diethy ether

Staphylococcus aureus

0.50 mg/ml

Nostro et al., 2001

Bacillus stearothermophilus Bacillus cereus Staphylococcus aureus Bacillus subtilis Bacillus stearothermophilus Bacillus cereus Staphylococcus aureus Vibrio cholerae Bacillus subtilis Escherichia coli O157:H7 Listeria monocytogenes Salmonella Enteritidis Salmonella Typhimurium Staphylococcus aureus Bacillus cereus Listeria monocytogenes Staphylococcus aureus

0.1% strong inhibition strong inhibition strong inhibition strong inhibition strong inhibition strong inhibition strong inhibition 125 µg/ml 500 µg/ml 125 µg/ml 1000 µg/ml 1000 µg/ml 125 µg/ml 8 mm 7 mm 10 mm

Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Bajpai et al., 2008 Bajpai et al., 2008 Bajpai et al., 2008 Bajpai et al., 2008 Bajpai et al., 2008 Bajpai et al., 2008 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007

Ethanol Ethanol (0.2%) Ethanol (0.2%) Ethanol (0.5%) Lavandula officinalis Chaix Ethanol (0.2%) (Lavender) Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Magnolia liliflora Desr. Essential oil (Lily magnolia) Essential oil Essential oil Essential oil Essential oil Essential oil Mentha canadensis L. (Mint) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml)

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Table 3. (Continued) Plant species Myristica fragrans Houtt. (Nutmeg)

Ocimum basilicum L. (Sweet basil) Origanum vulgare L. (Oregano)

Extract Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Ethanol Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Essential oil 10% Essential oil 10% Methanol (200 mg/ml) Methanol (200 mg/ml) Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well)

Bacterial species Bacillus subtilis Escherichia coli Staphylococcus aureus Yersinia enterocolitica Bacillus stearothermophilus Bacillus cereus Bacillus subtilis Staphylococcus aureus Escherichia coli Shigella flexneri Bacillus cereus Staphylococcus aureus Bacillus cereus Bacillus subtilis Bacillus subtilis Escherichia coli Escherichia coli Listeria monocytogenes Shigella flexneri Shigella sonnei Staphylococcus aureus Staphylococcus aureus Yersinia enterocolitica Bacillus subtilis Clostridium sporogenes Escherichia coli Staphylococcus aureus Yersinia enterocolitica

Inhibition zone or MIC 7 mm 10 mm 25 mm 7 mm 0.05-0.1% strong inhibition strong inhibition strong inhibition 5 mm 5 mm 6 mm 7 mm 20 µl/ml 31.25 µg/ml 20 µl/ml 31.25 µg/ml 40 µl/ml 80 µl/ml 40 µl/ml 20 µl/ml 62.5 µg/ml 20 µl/ml 20 µl/ml 21 mm >90 mm 30 mm 18 mm 34 mm

References Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Bagaboula et al., 2004 Bagaboula et al., 2004 Shan et al., 2007 Shan et al., 2007 Souza et al., 2006 Sahin et al., 2004 Souza et al., 2006 Sahin et al., 2004 Souza et al., 2006 Souza et al., 2006 Souza et al., 2006 Souza et al., 2006 Sahin et al., 2004 Souza et al., 2006 Souza et al., 2006 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000

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Origanum vulgare L. (Oregano)

Pimenta officinalis Lindl. (Allspice)

Piper nigrum L. (Black pepper)

Prostanthera incisa R. Br. (Native mint)

Psidium guajava L. (Guava)

Ethanol Ethanol (0.5%) Ethanol (0.5%) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Ethanol Ethanol (0.2%) Ethanol (0.5%) Ethanol (0.5%) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Ethanol Ethanol (0.2%) Ethanol (0.2%) Ethanol (0.5%) Ethanol (0.5%)

Bacillus stearothemophilus Bacillus cereus Staphylococcus aureus Bacillus cereus Escherichia coli Listeria monocytogenes Staphylococcus aureus Bacillus stearothemophilus Bacillus cereus Staphylococcus aureus Vibrio cholerae Bacillus subtilis Clostridium sporogenes Escherichia coli Staphylococcus aureus Yersinia enterocolitica Bacillus stearothemophilus Bacillus cereus Vibrio cholerae Bacillus subtilis Staphylococcus aureus

0.1% strong inhibition strong inhibition 11 mm 7 mm 14 mm 24 mm 0.1% strong inhibition strong inhibition strong inhibition 10 mm 9 mm 7 mm 15 mm 12 mm 0.1% strong inhibition strong inhibition strong inhibition strong inhibition

Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996

Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Methanol Methanol Methanol

Escherichia coli Listeria monocytogenes Salmonella Enteritidis Salmonella Typhimurium Staphylococcus aureus Escherichia coli Escherichia coli Salmonella Typhimurium Staphylococcus aureus

500 µg/ml 125 µg/ml 125 µg/ml 125 µg/ml 15.6 µg/ml 0.2 mg/ml 9.03 mg/ml 2.66 mg/ml 0.77 mg/ml

Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Dupont et al., 2006 Voravuthikunchai et al., 2004 Ushimaru et al., 2007 Ushimaru et al., 2007 Ushimaru et al., 2007

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Table 3. (Continued) Plant species Punica granatum L. (Pomegranate)

Rhus coriaria L. (Sumac)

Rosmarinus officinalis L. (Rosemary)

Extract Ethanol

Bacterial species Escherichia coli

Ethanol Ethanol Ethanol Methanol Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Water Water Water Water (0.5 mg/well) Water (0.5 mg/well) Water (0.5 mg/well) Water (0.5 mg/well) Alcohol (80% v/v) Alcohol (80% v/v) Alcohol (80% v/v) Alcohol (80% v/v) Alcohol (80% v/v) Ethanol (0.2%) Ethanol (0.5%) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml)

Salmonella Typhi Shigella sonnei Staphylococcus aureus Staphylococcus aureus Bacillus cereus Escherichia coli Listeria monogenes Staphylococcus aureus Salmonella Typhi Shigella sonnei Staphylococcus aureus Bacillus subtilis Escherichia coli Shigella dysenteriae Staphylococcus aureus Bacillus cereus Escherichia coli Salmonella Typhi Shigella flexneri Staphylococcus aureus Vibrio cholerae Staphylococcus aureus Bacillus cereus Listeria monocytogenes Vibrio cholerae

Inhibition zone or MIC References Voravuthikunchai and 0.19 mg/ml Limsuwan, 2006 Voravuthikunchai et al., 2004 6.25 mg/ml Voravuthikunchai et al., 2004 0.39 mg/ml Voravuthikunchai et al., 2004 0.39 mg/ml 0.01% v/v Braga et al., 2005 25 mm Shan et al., 2007 15 mm Shan et al., 2007 15 mm Shan et al., 2007 32 mm Shan et al., 2007 0.19 mg/ml Voravuthikunchai et al., 2004 12.5 mg/ml Voravuthikunchai et al., 2004 0.39 mg/ml Voravuthikunchai et al., 2004 18 mm Naz et al. 2007 11-13 mm Naz et al. 2007 13 mm Naz et al. 2007 Naz et al. 2007 20 mm 0.05 mg/ml Fazeli et al., 2007 0.2 mg/ml Fazeli et al., 2007 0.2 mg/ml Fazeli et al., 2007 0.2 mg/ml Fazeli et al., 2007 0.1 mg/ml Fazeli et al., 2007 strong inhibition Liu and Nakano, 1996 strong inhibition Liu and Nakano, 1996 8 mm Shan et al., 2007 7 mm Shan et al., 2007 9 mm Shan et al., 2007

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Salvia officinalis L. (Sage)

Syzygium aromaticum (L.) Merr. & L.M. Perry) (Clove)

Tamarindus indica L. (Tamarind)

Thymus vulgaris L. (Thyme)

Essential oil (20 µl/disc) Essential oil (20 µl/disc) Essential oil (20 µl/disc) Ethanol Ethanol Ethanol Ethanol (0.1%) Ethanol (0.2%) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Ethanol Ethanol (0.2%) Ethanol (0.2%) Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Ethanol (0.5%) Methanol Methanol Methanol Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Ethanol Ethanol Ethanol Ethanol Ethanol Essential oil 10% Essential oil 10%

Escherichia coli Listeria monocytogenes Staphylococcus aureus Bacillus cereus Bacillus stearothemophilus Bacillus subtilis Staphylococcus aureus Vibrio parahaemolyticus Bacillus cereus Listeria monocytogenes Staphylococcus aureus Bacillus stearothermophilus Bacillus cereus Vibrio cholerae Bacillus subtilis Escherichia coli Salmonella Typhimurium Staphylococcus aureus Escherichia coli Salmonella Typhimurium Staphylococcus aureus Bacillus cereus Escherichia coli Listeria monocytogenes Staphylococcus aureus Bacillus subtilis Escherichia coli Salmonella Typhi Shigella flexnieri Staphylococcus aureus Escherichia coli Shigella flexneri

19 mm 18 mm 20 mm 0.1% 0.05% 0.1% strong inhibition strong inhibition 8 mm 7 mm 9 mm 0.1% strong inhibition strong inhibition strong inhibition strong inhibition strong inhibition strong inhibition 1.60 mg/ml 1.67 mg/ml 0.46 mg/ml 14 mm 10 mm 14 mm 21 mm 8 mg/ml 15.5 mg/ml 10 mg/ml 8 mg/ml 8 mg/ml 5 mm 5 mm

Celikel and Kavas, 2008 Celikel and Kavas, 2008 Celikel and Kavas, 2008 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Ushimaru et al., 2007 Ushimaru et al., 2007 Ushimaru et al., 2007 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Doughari, 2006 Doughari, 2006 Doughari, 2006 Doughari, 2006 Doughari, 2006 Bagaboula et al., 2004 Bagaboula et al., 2004

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan, Nova Science

Copyright © 2010. Nova Science Publishers, Incorporated. All rights reserved.

Table 3. (Continued) Plant species

Zataria multiflora Boiss. (Avishan-e shirazi)

Zingiber officinale Roscoe (Ginger)

Zingiber zerumbet (Pinecone ginger)

Extract Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (15 µl/well) Essential oil (20 µl/disc) Essential oil (20 µl/disc) Essential oil (20 µl/disc) Essential oil (557 ppm) Essential oil (557 ppm) Ethanol Ethanol (0.2%) Ethanol (0.5%) Ethanol (0.5%) Methanol (200 mg/ml) Methanol (200 mg/ml) Methanol (200 mg/ml) Alcohol (80% v/v) Alcohol (80% v/v) Alcohol (80% v/v) Alcohol (80% v/v) Alcohol (80% v/v) Essential oil (557 ppm) Essential oil (557 ppm) Ethanol (80 µl/disc) Methanol Methanol Methanol Chloroform Chloroform

Bacterial species Bacillus subtilis Clostridium sporogenes Escherichia coli Staphylococcus aureus Yersinia enterocolitica Bacillus cereus Listeria monocytogenes Staphylococcus aureus Listeria monocytogenes Staphylococcus aureus Bacillus stearothemophilus Bacillus cereus Bacillus subtilis Staphylococcus aureus Bacillus cereus Listeria monocytogenes Staphylococcus aureus Bacillus cereus Escherichia coli Salmonella Typhi Shigella flexneri Staphylococcus aureus Listeria monocytogenes Staphylococcus aureus Staphylococcus aureus Escherichia coli Salmonella Typhimurium Staphylococcus aureus Bacillus cereus Staphylococcus aureus

Inhibition zone or MIC 23 mm >90 mm 32 mm >90 mm 26 mm 28 mm 23 mm 30 mm 24-46 mm 22 mm 0.1% strong inhibition strong inhibition strong inhibition 9 mm 8 mm 9 mm 0.4 mg/ml 0.4 mg/ml 0.8 mg/ml 0.4 mg/ml 0.4 mg/ml 6 mm 6 mm 11 mm 6.97 mg/ml 6.97 mg/ml 7.79 mg/ml 0.39 mg/ml 0.39 mg/ml

References Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Dorman and Deans, 2000 Celikel and Kavas, 2008 Celikel and Kavas, 2008 Celikel and Kavas, 2008 Nguefack et al., 2004 Nguefack et al., 2004 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Liu and Nakano, 1996 Shan et al., 2007 Shan et al., 2007 Shan et al., 2007 Fazeli et al., 2007 Fazeli et al., 2007 Fazeli et al., 2007 Fazeli et al., 2007 Fazeli et al., 2007 Nguefack et al., 2004 Nguefack et al., 2004 Oonmetta-aree et al., 2006 Ushimaru et al., 2007 Ushimaru et al., 2007 Ushimaru et al., 2007 Voravuthikunchai et al., 2006 Voravuthikunchai et al., 2006

Applications of Natural Products in Food, edited by Supayang Piyawan Voravuthikunchai, and Beatrice Olawumi T. Ifesan, Nova Science

Copyright © 2010. Nova Science Publishers, Incorporated. All rights reserved.

Table 4. Antibacterial activity of plant extracts or their essential oils in foods Food

Plant extract or essential oil

Organism

Reduction in population (log cfu/g or log cfu/ml)

References

Carvacrol 1 mM Carvacrol 1 mM Cinnamic acid 1 mM Cinnamic acid 1 mM Carvacrol 1 mM Carvacrol 1 mM Cinnamic acid 1 mM Cinnamic acid 1 mM

Total viable organisms Total viable organisms Total viable organisms Total viable organisms Total viable organisms Total viable organisms Total viable organisms Total viable organisms

4 (4°C, 5 days) 6 (8°C, 3 days) 4 (4°C, 5 days) 6 (8°C, 3 days) 4 (4°C, 5 days) 1.5 (8°C, 5 days) 4 (4°C, 5 days) 1.5 (8°C, 5 days)

Roller and Seedhar, 2002 Roller and Seedhar, 2002 Roller and Seedhar, 2002 Roller and Seedhar, 2002 Roller and Seedhar, 2002 Roller and Seedhar, 2002 Roller and Seedhar, 2002 Roller and Seedhar, 2002

Total viable organisms

3 (30°C, 4 days)

Mau et al., 2001

Pineapple juice Pineapple juice

Chinese chives, cinnamon, corni fructus 0.1% w/v Cinnamomum oil 10 µl Cinnamomum oil 10 µl

Total viable organisms Yeast and mold

1 (7 days) 1 (7 days)

Kapoor et al., 2008 Kapoor et al., 2008

MEAT Beef Beef Beef Beef Cooked beef Cooked beef Cooked beef Lean beef Lean beef Lean beef

Clove oil 1% Pine bark 1% Pine bark 1% Pine bark 1% Clove oil 7.5 ml/l Clove oil 7.5 ml/l Tea tree oil 15 ml/l Garlic paste 5% Ginger 7% Tumeric 3.5%

Listeria monocytogenes Escherichia coli O157:H7 Listeria monocytogenes Salmonella Typhimurium Aerobic organisms Escherichia coli O157:H7 Escherichia coli O157:H7 Salmonella Typhimurium Salmonella Typhimurium Salmonella Typhimurium

1-3 (7 or 30°C, 3 days) 1 (4°C, 9 days) 1 (4°C, 9 days) 1 (4°C, 9 days) 1 (8-10°C, 3 hours) 1.5 (8-10°C, 18 hours) 2.5 (8-10°C, 18 hours) >1 (8°C, 10 days)