Handbook of Active Marine Natural Products: Volume 2 Terpenoids, Part 2 9783110655155, 9783110653250

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Jiaju Zhou Handbook of Active Marine Natural Products

Handbook of Active Marine Natural Products Jiaju Zhou Volume : Terpenoids, Part  ISBN ----, e-ISBN (PDF) ----, e-ISBN (EPUB) ----

Volume : Alkaloids, Part  ISBN ----, e-ISBN (PDF) ----, e-ISBN (EPUB) ----

Volume : Alkaloids, Part  ISBN ----, e-ISBN (PDF) ----, e-ISBN (EPUB) ----

Volume : Polyketides and Steroids ISBN ----, e-ISBN (PDF) ----, e-ISBN (EPUB) ----

Volume : Aliphatic Metabolites ISBN ----, e-ISBN (PDF) ----, e-ISBN (EPUB) ----

Volume : O-Heterocycles and Aromatics ISBN ----, e-ISBN (PDF) ----, e-ISBN (EPUB) ----

Volume : Peptides and Others ISBN ----, e-ISBN (PDF) ----, e-ISBN (EPUB) ----

Jiaju Zhou

Handbook of Active Marine Natural Products Volume 2: Terpenoids, Part 2

Author Prof. Jiaju Zhou Chinese Academy of Sciences 1303 Department, 10 Building 31 Zhong Guan Cun Nan Dajie 100081 Beijing China [email protected]

ISBN 978-3-11-065325-0 e-ISBN (PDF) 978-3-11-065515-5 e-ISBN (EPUB) 978-3-11-065328-1 Library of Congress Control Number: 2019941348 Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.dnb.de. © 2019 Walter de Gruyter GmbH, Berlin/Boston Typesetting: Integra Software Services Pvt. Ltd. Printing and binding: CPI books GmbH, Leck Cover image: Science Photo Library/Douwma, Georgette www.degruyter.com

Preface The English edition Handbook of Active Marine Natural Products (HAMNP) with 8 Volumes is a selective version of the Marine Natural Products Dataset. The whole dataset was collected and developed by the Molecular Design Group, Institute of Process Engineering, Chinese Academy of Sciences during 1998–2016. Totally, it covers 19,722 entries of secondary metabolites from marine living things, where 8,350 compound entries have pharmacological activity data. The 8,350 compound entries were arranged into eight volumes to form the set of handbooks as follows: Volume 1: Terpenoids, Part 1 Volume 2: Terpenoids, Part 2 Volume 3: Alkaloids, Part 1 Volume 4: Alkaloids, Part 2 Volume 5: Polyketides and Steroids Volume 6: Aliphatic Metabolites Volume 7: O-Heterocycles and Aromatics Volume 8: Peptides and Others This set of eight HAMNP books gathers the structure, origin, and bioactivity, as well as other relevant information, of 8,350 active marine natural products from 3,025 marine organisms. The HAMNP handbook represents a largest collection of active secondary metabolites from marine organisms, and all kinds of scientific data have been reorganized as well-formatted data so that the books became helpful to researchers as a convenient reference. The materials covered in these books include those through systematic collection up to 2012, and further accompanied with the latest data published in several core journals until 2016. The work covered in these HAMNP books was accomplished in two phases. The initial phase ranged from 1998 to 2001 and the main phase from 2011 to 2018. In the original version of the dataset, more than 22,000 compounds have been collected, including duplicated compounds from different authors. The comprehensive data compilation process include data specification definition, cross-validation, assessment confirmation, identification of duplicated structures, and merging of relevant information, leading to the final accomplishment of the current 19,722 datasets. In brief, the main compilation process of the HAMNP books is given as follows. First, collect the name list, origin, and structure of chemical compounds from successive annual reviews (see Core References R01 and R02 in Introduction) and literature reviews. Second, double-check the documents to verify and complete other information. Third, confirm the structural information and other types of data using orthogonal information from other sources with cross-validation methods. Fourth, the structures of more than 22,000 compounds are rechecked and the information is integrated by manual identification and computer programs. Finally, the comprehensive information https://doi.org/10.1515/9783110655155-201

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on the 19,722 compounds constitutes the dataset. Here, 8,350 active sets were picked up from the dataset to form the current HAMNP handbooks. Three problems need to be solved to compile a multidisciplinary reference book. First, every definition and concept should be explicit when expanding knowledge, connotation, and extension included, without any research details. Second, the reliability assessment is essential for all kinds of data, because the devil is in the detail. Third, it is essential to search, identify, and integrate data of duplicated chemical compounds. Fortunately, well-developed software packages can help us automatically identify the majority of duplicated chemical compounds. The remaining issues can be resolved along with manual processing. It is the guiding principle of the author to make the book to be pithy, thorough, precise, and intelligible. In fact, we always view ourselves as HAMNP’s readers, with the exclusive objective to let readers gain the most useful knowledge in the shortest possible time. The core contents and highlights of the HAMNP books are the “three diversities,” that is, the diversity of chemical structures, the diversity of biological resources, and the diversity of pharmacological activities. In terms of chemical structure diversity, we refer to the classification system from references, then further improve and expand it based on the latest research and development to define our classification framework of structures. Once readers browse the contents of the books, the classification system is straightforward. For the diversity of biological resources, it is recommended to refer to Index 3 in each volume – Compound Marine Organism Source Index; and Index 4 in each volume – Compound Marine Source Sampling Geographic Location Index. For the diversity of pharmacological activities, it is recommended to refer to Index 5 in each volume – Compound Pharmacological Activity Index. These HAMNP handbooks are expected to help readers who are engaged in research, in teaching, and in the development of marine natural products. It should also benefit college students, postgraduates, marine resource managers, and those who are interested in the chemistry and pharmacology of marine natural products. We would feel fortunate if it works as expected.

Jiaju Zhou Institute of Process Engineering (IPE), Chinese Academy of Sciences (CAS) February 2019

Contents Preface V About the Author IX Introduction XI How to Use the HAMNP Books XIX List of Abbreviations and Acronyms XXIII List of Cancer Cell Codes XXXIII 3

Diterpenoids (continuing) 1 3.19 Dolabellane Diterpenoids 1 3.20 Dolastane Diterpenoids 11 3.21 Cyathane Diterpenoids 11 3.22 Modified Verrucosane Diterpenoids 14 3.23 Spatane Diterpenoids 16 3.24 Verticillane Diterpenoids 17 3.25 Taxane Diterpenoids 20 3.26 Amphilectane Diterpenoids 21 3.27 Cycloamphilectane Diterpenoids 40 3.28 Adociane Diterpenoids 42 3.29 Xenicane Diterpenoids 45 3.30 Prenyleudesmane Diterpenoids 64 3.31 Prenylgermacrane Diterpenoids 64 3.32 Prenylbicyclogermacrane Diterpenoids 65 3.33 Lobane Diterpenoids 66 3.34 Pachydictyane Diterpenoids 71 3.35 Cneorubine Diterpenoids 74 3.36 Serrulatane and Biflorane Diterpenoids 74 3.37 Sacculatane Diterpenoids 91 3.38 Obtusane Diterpenoids 92 3.39 Irieol Diterpenoids 92 3.40 Sphenolobane Diterpenoids 93 3.41 Spiroditerpenoids 93 3.42 Miscellaneous Diterpenoids 96

4

Sesterterpenoids 127 4.1 Acyclic Sesterterpenoids 127 4.2 Noracyclic Sesterterpenoids 135 4.3 Cyclohexane Sesterterpenoids 140 4.4 Bicyclic Sesterterpenoids 152 4.5 Cheilanthane Sesterterpenoids 161 4.6 Ophiobolane Sesterterpenoids 171

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4.7 4.8 4.9

Scalarane Sesterterpenoids 175 Methyl- and Dimethylscalarane Sesterterpenoids Miscellaneous Sesterterpenoids 199

191

5

Triterpenoids 211 5.1 Linear Triterpenoids 211 5.2 Lanostane Triterpenoids 217 5.3 Cycloartane Triterpenoids 265 5.4 Rearranged Tetranortriterpenoids 269 5.5 Oleanane Triterpenoids 273 5.6 Malabaricane and Isomalabaricane Triterpenoids 276 5.7 Raspacionins and Sodwanones Triterpenoids 287 5.8 Zoanthamine Triterpenoids 289 5.9 Other Triterpenoids 293

6

Polyterpenoids and Meroterpenoids 299 6.1 Tetraterpenoids 299 6.2 Tetra-above Polyterpenoids 305 6.3 Apocarotenoids 305 6.4 Megastigmane Norterpenoids 306 6.5 Bromophycolide Meroterpenoids 306 6.6 Metachromin Meroterpenoids 311 6.7 Other Meroterpenoids 314

Index 1 Compound Name and Synonym Index 397 Index 2 Compound Molecular Formula Index 414 Index 3 Compound Organism Source Index 433 Index 4 Compound Sampling Geographic Locality Index 440 Index 5 Compound Pharmacological Activity Index 444

About the Author Prof. Jiaju Zhou was born in October 1939 in Tianjin, China. He graduated from Rare Earth Inorganic Chemistry Specialty, Chemistry Department, Peking University, in 1963 under a six-year program. Before he retired in 2008, Zhou was the leader of Molecule Design Group, IPE, CAS. Zhou’s areas of research include rare earth chemistry, mineral analytical chemistry, chemical industry process simulation (in IPE, CAS and UBC, Canada), design of crystal structural database (in OSRD, NIST, Gaithersburg, MD, USA), scientific database R&D, and computer-aided and artificial intelligence drug design. Zhou developed the first TCM database (TCMDB) with 23,033 entries. Since 2008, he has worked on Marine Natural Products project and has developed the Marine Natural Products Database (MNPDB) with 19,722 entries.

https://doi.org/10.1515/9783110655155-202

Introduction The Handbook of Active Marine Natural Products covers eight volumes. This book is Volume 2: Terpenoids, Part 2, which includes 1,061 active compounds. Format of Compound Entry. A compound entry starts with a title line, which has two items: the compound’s unique code (from 1 to 1,061 for volume 2) and the main name. The following eight items form the title line as a body, and the graphic structure is placed at the end: Title line (code number, main name) A. Synonyms of the compound (if any) B. Structural type C. Formula (relative molecular mass) D. Physicochemical properties E. Marine source(s) F. Pharmacological data (if any) G. Reference(s) Graphic structure Chemical Names and A. Synonyms. Generally, a compound may have one scientific name and several trivial names. In the handbooks, based on original articles, we select one name as the “main name.” The main name appeared at the title line of each compound entry. In most cases, a trivial name was selected as the main name, and in some cases, the main name is a scientific name. Any synonyms, if any, are presented after the title line as an item of the entry body. B. Structural Type. Structural type is the second item, ordered by the contents order. F. Normalization of Pharmacological Data. All of 1,061 MNP components in this book have pharmacological data, which are very valuable. Because different expressions are used for the same kind of data in different articles, we have to define and normalize thousands of pharmacological terms, so that the data could be expressed in a unified way, and be easily understood by readers. Stereochemistry in Graphic Structure. We protracted all compound structures down to atomic bond level, including complicated glycosides, with stereochemical information based on the data in the original papers. For example, the structure with full stereochemistry of compound 456 Sigmosceptrellin B is H H O

O

O OH

https://doi.org/10.1515/9783110655155-203

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Let us further explain the data structure of source terms and pharmacological terms.

Source Terms The source data of compound 456 Sigmosceptrellin B is Source: Sponge Diacarnus erythraenus (Red Sea) Sponge Diacarnus cf. spinopoculum (Solomon Is. and Papua New Guinea) Sponge Sigmosceptrella laevis Sponge Prianos sp. The format is as follows (banding the English-type name and the Latin name together): Source: English-type name + Latin name of source 1 (sampling place, sampling season water depth, etc.) English-type name + Latin name of source 2 English-type name + Latin name of source 3 English-type name + Latin name of source 4

Pharmacological Terms The pharmacological terms in the handbooks are presented in a multilayered structure. In the top layer, there are more than 20 types of the most important pharmacological activity terms. They are cytotoxic (in vitro anticancer), antineoplastic (in vivo anticancer), antibacterial, antifungal, antiviral, anti-HIV, anti-inflammatory, antioxidant, antimalarial, NO production inhibitors, enzyme inhibitors, cardiovascular activity, smooth muscle relaxant and stimulant, toxin and medium lethal dose (LD50), and so forth. Readers need to be familiar with these Tope lever pharmacological terms (see Table 1). For each term there is a regulation about how to describe related pharmacological data. The following is an example. Under the subtitle “Pharm:” of compound 456 Sigmosceptrellin B, a set of multiple biodata is presented as follows: Pharm: Antimalarial (Plasmodium falciparum D6, IC50 = 1200 ng/mL, SI > 2.7; Plasmodium falciparum W2, IC50 = 3400 ng/mL, SI > 1.0); antitoxoplasma (Toxoplasma gondii, 0.1 μmol/L without significant toxicity); differential cytotoxicity (soft agar assay, 50 μg/disk, zone differential of 250 units is expected for “selective activity,” C38-L1210, − 50 zone differential units; M17-L1210, − 10 zone differential units);

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Table 1: Twenty-Four Main Pharmacological Terms in Tope Lever. Order in Index 

Pharmacological Terms in Tope Lever

                       

Anti-AD Antibacterial Antifungal Anti-HIV Anti-inflammatory Antileishmanial Antimalarial Antineoplastic (in vivo) Antioxidant Antiplasmodial Antitrypanosomal Antituberculosis Antiviral Cardiovascular activity Cell cycle inhibitor Cell division inhibitor Cell growth inhibitor Cell adhesion inhibitor Cytotoxic (in vitro) Enzyme inhibitors NO production inhibitors Smooth muscle relaxant and stimulant Toxin Medium lethal dose (LD)

cytotoxic (Vero, IC50 = 2.5 μg/mL); cytotoxic (HL60, GI50 = 0.14 μmol/L; Molt4, GI50 = 0.98 μmol/L; A549/ATCC, GI50 = 1.45 μmol/L; KM12, GI50 = 0.94 μmol/L; IGROV1, GI50 = 0.12 μmol/L; 7860, GI50 = 0.61 μmol/L; BT-549, GI50 = 1.81 μmol/L). The format is as follows: Pharm: Term name 1 (formatted detail information) Term name 2 (formatted detail information) Term name 3 (formatted detail information) Term name 4 (formatted detail information) Under the term name Cytotoxic, a set of multiple cytotoxic biodata is presented as follows:

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Cytotoxic (Vero, IC50 = 2.5 μg/mL; HL60, GI50 = 0.14 μmol/L; Molt4, GI50 = 0.98 μmol/L; A549/ATCC, GI50 = 1.45 μmol/L; KM12, GI50 = 0.94 μmol/L; IGROV1, GI50 = 0.12 μmol/L; 786-0, GI50 = 0.61 μmol/L; BT-549, GI50 = 1.81 μmol/L). The format is as follows: Term name (in vitro/in vivo, target cancer cell 1, quantitative data, positive control compound, control’s quantitative data (if any); target cancer cell 2, quantitative data, positive control compound, control’s quantitative data (if any); brief description of related mechanism if any). In order to standardize abbreviations of cancer cells, such as P388, A549, HT29, MEL28, CCRF-CEM, and DLD-1, we defined and used 438 cancer cell codes (CCC) in the handbooks. For explanations of these codes, please see “List of Cancer Cell Codes.” By means of the formatted and structuralized methods, we normalized expressions of almost all the pharmacological data discussed in the books. For complete information in volume 2, of all 721 normalized pharmacological activity terms, please see “Index 5 Compound Pharmacological Activity Index.” In summary, these handbooks with eight volumes provide an integrated collection of 8,350 marine natural products’ chemical components isolated from 3,025 marine organisms and a large amount of pharmacological activity data of these components. It might be used not only as a handbook to look for structures and bioactivities of marine natural products and marine organisms source information, but also as a fundamental platform for studying the marine natural products with a systematic and integrative approach.

Acknowledgments First, I would like to give my heartfelt thanks to Dr. David Lide and B.J. Lide, who were my directors 30 years ago when I worked in OSRD, NIST (former NBS), USA, in 1985–1986 for nine months. They gave me the rare opportunity to learn how to use a software platform and how to treat a complicated scientific information data system. It is my research experience in NBS that helped me to compile easily the current huge project in Marine Natural Products. At the same time, I also give my

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sincere thanks to my NBS’s colleagues: Dr. John Rumble, Mrs. Geraldine Dalton, Mrs. Phoebe Fagan, and other OSRD members. Then, I would like to give my genuine thanks to the following two close friends. They gave my MNP project continual concerns and supports for years: Dr. Jun Xu, Professor and Director, Research Center for Drug Discovery, Sun Yet-Sen University, 132 East Circle, University City, Guangzhou 510006, China, and Dr. Leming Shi, Professor and Director, Center for Pharmacogenomics, School of Life Sciences and Shanghai Cancer Center, Fudan University, Shanghai 200438, China ([email protected]). Third, I like to give my honest thanks to my following group members. For many years, all of them gave various devices to me: 1 Dr. Jing Lei, Associate Professor, Educational Equipment Research and Development Centre, Ministry of Education of the People’s Republic of China, Beijing 100080, China (early research in her doctor thesis) 2 Dr. Bing Liu, Lead Dev Prophix Software Inc. 350 Burnhamthorpe Road West, Suite 1000 Mississauga, Ontario L5B 3J1, Canada (data collection in the early stage) 3 Master Yingxin Qiao, Software Engineer, National Library of China, Beijing 100081, China (data source searching and original paper collection) 4 Dr. Haibo Liu, Associate Professor, The Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Beijing 100193, China (special software development for automatic edition) 5 Dr. Tao Peng, Associate Professor, College of Robotics, Beijing Union University, Beijing 1001011, China (special software development for index generation) 6 Dr. Aihua Xie, Associate Professor, School of Pharmacy, Hebei Chinese Medical University, Shijiazhuang, Hebei 050200, China (part of data collection) 7 Dr. Chenzhong Liao, Professor, Dean of Department of Pharmacy, School of Biological and Medical Engineering, Hefei University of Technology, Hefei 230009, China (original paper collection) 8 Dr. Jianfeng Pei, Associate Professor, Center for Quantitative Biology, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871, China (data collection in the early stage) 9 Dr. Xianfeng He, Associate Professor, Scientific Researcher, EMMS Group, State Key Laboratory of Multiphase Complex Systems, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China (data collection in the early stage) 10 Madam Guirong Xie, Associate Professor, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China (part of data compilation) 11 Mr. Wucheng Tang, Engineer, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China (part of original paper collection) Finally, the author would like to give my heavy thanks to my family members. Without their complete and never-ending support, this book would never have been completed.

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Core References (Guiding References 5) R01 D. J. Faulkner, Marine Natural Products (review), Nat. Prod. Rep., 1986, 3, 1–33; 1987, 4, 539–576; 1988, 5, 613–663; 1990, 7, 269–309; 1991, 8, 97–147; 1992, 9, 323–364; 1993, 10, 497–539; 1994, 11, 355–394; 1995, 12, 223–269; 1996, 13, 75–125; 1997, 14, 259–302; 1998, 15, 113–158; 1999, 16, 155–198; 2000, 17, 7–55; 2001, 18, 1R–49R; 2002, 19, 1–49 R02 J. W. Blunt, et al, Marine Natural Products (review), Nat. Prod. Rep., 2003, 20, 1–48; 2004, 21, 1–49; 2005, 22, 15–61; 2006, 23, 26–78; 2007, 24, 31–86; 2008, 25, 35–94; 2009, 26, 170–244; 2010, 27, 165–237; 2011, 28, 196–268; 2012, 29, 144–222; 2013, 30, 237–323; 2014, 31, 160–258; 2015, 32, 116–211 R03 J. Buckingham (Executive Editor), Dictionary of Natural Products, Chapman & Hall, London, Vol. 1–Vol. 7 1994; Vol. 8, 1995; Vol. 9, 1996; Vol. 10, 1997; Vol. 11, 1998 R04 CRC Press, Dictionary of Natural Products on DVD, version 20.2, 2012 R05 Jean-Michel Kornprobst, Encyclopedia of Marine Natural Products, Vol. 1– Vol. 3, 2nd Edition, WILEY BLACKWELL, Germany, 2014

(Dictionaries 17) R06 P.M. Kirk, P.F. Cannon, D.W. Minter and J.A. Stalpers, Dictionary of the Fungi, 10th Edition, CABI Europe-UK, 2011 R07 Miaoying Cai, et al., Names of Bacteria, 2nd Edition, Science Press, Beijing, 1996 R08 Rui-Fu Yang et al, Dictionary of Bacterial Names with English Explanation and Chinese Translation, Chemical Industry Press, Beijing, 2011 R09 Zongxun Wang et al. (Institute of Botany, Chinese academy of Sciences), New Edited Plant Names in Latin-Chinese-English, Aerial Industry Press, Beijing, 1996 R10 Zhong-Yan Qi and Xi-Xing Liu, New Names of Invertebrate Animals in Latin-Chinese, Science Press, Beijing, 1999 R11 Ling-Ti Lu and Jia-Ran Zhu, Dictionarium Lantino-Sinicum de Scientia et technologia, The Commercial Press, Beijing, 2017 R12 Ji-Sheng Chen, et al., English-Chinese Dictionary of Life Science, Scientific and technological Literature Press, Beijing, 1992 R13 P. Singleton and D. Sainsbury (Qing-jun Ma and Cheng-hua Shi et al. translated), Dictionary of Microbiology and Molecular Biology, Chemical Industry Press, Beijing, 2008 R14 Scientific Terms Laboratory of Science Press, English-Chinese Dictionary of Chemistry and Chemical Engineering, 4th Edition, Science Press, Beijing, 2000 R15 Scientific Terms Laboratory of Science Press, English-Chinese Dictionary of Chemistry and Chemical Engineering, 5th Edition, Science Press, Beijing, 2016 R16 Jian Zhuge and Zheng-Xiang Wang, Modern English-Chinese Dictionary of Biotechnology, Science Press, Beijing, 2003 R17 Jing-Ying Tan, English-Chinese Biological Dictionary of Biochemistry and Molecular Biology, 2nd Edition, Science Press, Beijing, 2007 R18 Scientific Terms Laboratory of Science Press, English-Chinese Biological Dictionary, 2nd Edition, Science Press, Beijing, 1997 R19 Scientific Terms Laboratory of Science Press, Chinese-English Biological Dictionary, 2nd Edition, Science Press, Beijing, 1998

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R20 Yu Hui, A New Century Chinese-English Dictionary, Foreign Language Teaching and Research Press, Beijing, 2003 R21 Zong-Guo Huang and Mei-Ling Jin, Dictionary of Marine Biology, Ocean Press, Beijing, 1994 (in Chinese) R22 Wenbao Chang, et al., Dictionary of Chemistry, Science Press, Beijing, 2008 (in Chinese)

(Book References 11) R23 Hua-Shi Guan and Shu-Guang Wang, Zhong-hua Hai-yang Ben-cao, Marine Natural Products, 3 Volumes, Chemical Industry Press and Shanghai Science and Technology Press, Beijing, 2009 (in Chinese) R24 C. J. Alexopoulos, M. Blackwell and C. W. Mims, (Yijian Yao and Yu Li translated), Introductory Mycology, Fourth Edition, John Wiley & Sons, Inc., 1996, Chinese Agricultural Press, Beijing, 2002 R25 Janet S. Dodd, The ACS Style Guide, A Manual for Authors and Editors, 2nd Edition, American Chemical Society, Washington, DC, 1997 R26 Shu-Xian Ren, Invertebrates, 2 volumes, Peking University Press, Beijing, 1990 (in Chinese) R27 R. Mcneill Alexander, (translated by Lan-zhi Du), The invertebrates, Chemical Industry Press, Beijing, 2013 (in Chinese) R28 Yanghua Yi and Binghua Jiao, Modern Marine pharmacology, Science Press, Beijing, 2006 (in Chinese) R29 Chang-Yun Wang and Chang-Lun Shao, Marine pharmacology, Science Press, Beijing, 2011 (in Chinese) R30 Rensheng Xu, et al., Chemistry of Natural Products, 2nd Edition, Science Press, Beijing, 2004 (in Chinese) R31 Yue-Zeng Chen, General Biology, Higher Education Press, Beijing, 1997 (in Chinese) R32 Jiaju Zhou, Guirong Xie and Xinjian Yan, Encyclopedia of traditional Chinese Medicines, Molecular Structures, Pharmacological Activities, Natural Sources and Applications, Vol. 1– Vol. 6, Springer, Heidelberg Dordrecht London New York, 2011 R33 Jiaju Zhou, Guirong Xie and Xinjian Yan, TCM Series of Active Components, 10 books, Science Press, Beijing, 2012 (in Chinese)

How to Use the HAMNP Books In essence, from data computerization point of view, scientific knowledge is the expression of interrelation between research objects in different types. During a long coastline without computer, people learn and spread scientific knowledge in traditional ways, including education, reading, and exchanging information with each other. In today’s world, using computer’s powerful functions, we have a new way to learn systematical, complete knowledge. In short, a study process in the new way is to search and learn some relationships. Next, we discuss concretely how to use the HAMNP books. In these books, there are three kinds of data and three pairs of important relations. Three kinds of data are: (1) marine living sources (source); (2) secondary metabolites (compounds); and (3) pharmacological activities (pharm-activity). The three pairs of important relations are: (1) relationship between source and compounds; (2) relationship between compounds and pharm-activity; and (3) relationship between source and pharm-activity. In the case of asking questions, each relation has two directions; hence, together there are six types of questions: Type 1: from known source to unknown compound Type 2: from known compound to unknown source Type 3: from known compound to unknown pharm-activity Type 4: from known pharm-activity to unknown compound Type 5: from known source to unknown pharm-activity Type 6: from known pharm-activity to unknown source (Figure 1) S ource (s) Type 1

Type 5

T ype 6

Type 2

T ype 4

C om pound(s)

P harm-activity

T ype 3

Figure 1: Kinds of Data and Six Types of Questions.

(1) An Illustration of Type 1 (and Type 3, Type 5) Question Up to now, what triterpenoids are isolated from sponges of genus Jaspis? From index 3 of volume 2, one will get the following related data in detail: Jaspis sp. 742, 743, 744, 752, 759. Jaspis splendens 1038 (not a triterpenoid). https://doi.org/10.1515/9783110655155-204

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Jaspis stellifera 745, 746, 747, 748, 749, 750, 751, 755. Since compounds 600–778 are triterpenoids, these 13 compounds are the answer of the current question. Then, readers can enjoy studying these 13 compounds by reading the book, including their pharm-activity (question of types 3 and 5). For example, with entry 742, a reader will know that the compound 742 “29-Hydroxystelliferin A” had already been isolated from sponge Jaspis sp. near Tonga, Japan, and it has cytotoxic pharmaceutical activity (mixture with 13E-29-Hydroxystelliferin A: MALME-3M, IC50 = 0.11 μg/mL; Molt4, IC50 = 1.62 μg/mL). O

O

OH

H O HO

H

(2) An Illustration of Type 4 (and Type 2, Type 6) Question “What are isolated compounds with pharmacological activity against hmn nonsmall cell lung cancer from triterpenoids? And what are their marine sources?” Because involving cancer cells, the List of Cancer Cell Codes must be used first. By the question, three related items were being collected as the objects (small cell lung cancer): A549 hmn nonsmall cell lung cancer (cell) A549 NSCL hmn nonsmall cell lung cancer (cell) A549/ATCC hmn nonsmall cell lung cancer (cell) Then, to browse Index 5 of volume 2, searching “Cytotoxic, A549,” “Cytotoxic, A549 NSCL,” and “Cytotoxic, A549/ATCC,” respectively, the following results were obtained: Cytotoxic, A549 (1, 2, 6, 18, 19, 24, 28, 29, 44, 45, 46, 47, 48, 53, 54, 55, 57, 59, 127, 159, 160, 188, 201, 213, 214, 223, 224, 227, 233, 236, 272, 316, 317, 319, 366, 369, 375, 376, 377, 378, 379, 427, 429, 451, 452, 504, 506, 510, 518, 532, 533, 534, 538, 540, not terpenoids), 603, 604, 606, 607, 608, 612, 613, 615, 616, 639, 640, 664, 668, 669, 670, 698, 758, 762, 763, (871, 925, 947, 956, 960, 979, 991, 998, 999, 1002, 1003, 1003, 1025, not terpenoids). Cytotoxic, A549/ATCC: CCL8 381 (not a triterpenoid). Cytotoxic, A549, mixture with bilosespene A 436 (not a triterpenoid). Cytotoxic, A549, mixture with bilosespene B 435 (not a triterpenoid).

How to Use the HAMNP Books

XXI

Cytotoxic, A549/ATCC 456, 457 (not a triterpenoid). Cytotoxic, A549/ATCC, GI50 > 5.0 μmol/L 423 (not a triterpenoid). Since compounds 600–778 are triterpenoids, the answer of the current question must be: Cytotoxic, A549 603, 604, 606, 607, 608, 612, 613, 615, 616, 639, 640, 664, 668, 669, 670, 698, 758, 762, 763. Further, from the entry bodies of the 19 compounds, all sources can be obtained (see Table 2).

Table 2: Answer to the Above Type 4 Question. Vol.

Code

Compound Name

Related Sources





-epi-Dehydrothyrsiferol

Red alga Laurencia viridis sp. nov (Macaronesia in Canary Is)





Dioxepandehydrothyrsiferol

Red alga Laurencia viridis (off Canary Is)





Hippospongic acid A

Sponge Hippospongia sp. (Japan)

. . .. . .

. . .. . .

. . .. . .

. . .. . .





Stellettin E

Sponge Rhabdastrella globostellata (Hainan I., South China Sea)





Sodwanone G

Sponge Axinella weltneri (South Africa)





Sodwanone H

Sponge Axinella weltneri (South Africa)

In summary, by using three parts of the books – the contents (ordered by structural classifications), the text (8,350 compound entries in volumes 1–8), and the indexes – readers can easily gain well-formatted systematically related knowledge in multidisciplinary fields.

List of Abbreviations and Acronyms [3H]AMPA [3H]CGS-19755 [3H]CPDPX [3H]DPDPE [3H]KA ‡ 3Y1 5-FU 6-MP 6-OHDA AAI ABRCA ABTS•+ ACAT ACE AChE ACTH ADAM9 ADAM10 ADM AGE AIDS AKT AKT1 ALK AMPB AP-1 APOBEC3G aq ARCA ARK5 ATCC ATPase Aurora-B AXL AZT BACE BACE1 BCG Bcl-2 BoMC BoMCL bp c CaMKIII cAMP CAPE

[3H]-1-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid N-methyl-D-aspartic acid (NMDA) receptor antagonist [3H]-1,3-dipropyl-8-cyclopentylxanthine opioid peptide [3H]-kainic acid homonym mark rat fibroblasts 5-fluorouracil 6-mercaptopurine 6-hydroxydopamine antioxidant activity index (final DPPH concentration/EC50) amphotericin B-resistant Candida albicans 2,2′-azino-bis-(3-ethyl benzthiazoline 6-sulfonic acid), radical Acyl-CoA: cholesterol acyl transferase angiotensin-converting enzyme acetylcholinesterase adrenocorticotropic hormone ADAM9 protease ADAM10 protease adriamycin advanced glycation end products acquired immune deficiency syndrome ribosomal protein protein kinase protein kinase amphotericin B transcription factor hmn innate intracellular antiviral factor (recombinant protein) aqueous solution amphotericin-resistant Candida albicans protein kinase American Type Culture Collection adenosine triphosphatase protein kinase protein kinase 3′-azido-3′-deoxythymidine β-secretase β-secretase Bacille Calmette-Guérin a cell survival promoting factor further abbreviation on Bioorg. Med. Chem. further abbreviation on Bioorg. Med. Chem. Lett. boiling point concentration protein kinase cyclic adenosine monophosphate caffeic acid phenethyl ester

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XXIV

List of Abbreviations and Acronyms

caspase-3 CB CC50 CCR5 CD Cdc2 Cdc25 Cdc25a Cdc25b CDDP CDK CDK1 CDK2 CDK4 CDK4/cyclin D1 P25 p25 CDK7 c-erbB-2 CETP cGMP CGRP ChAT CMV CNS COMPARE ConA COX-1 COX-2 CPB cPLA2 CPT CRPF CRPF FcM29 CSPF Cyp1A CYP1A CYP450 1A d D Delta DGAT DHFR DMSO DNA DOX DPI DPPH

caspase-3 protein cytochalasin B IC50 of cytotoxicity (concentration of the 50% cytotoxic effect) chemokine receptor 5 concentration required to double the specific activity cyclin-dependent kinase protein Cdc25 phosphatase protein phosphatase recombinant hmn phosphatase cis-diaminedichloroplatinum (cisplatin) cyclin-dependent kinase protein kinase protein kinase protein kinase cyclin-dependent kinase 4 (CDK4) in complex with its activator cyclin D1 protein kinase protein kinase protein kinase protein kinase cholesteryl ester transfer protein cyclic guanylic acid, cyclic guanosine monophosphate calcitonin gene-related peptide choline acetyltransferase CMV protease central nervous system COMPARE is an algorithm to analyze data concanavalin A cyclooxygenase-1 cyclooxygenase-2 further abbreviation on Chem. Pharm. Bull. cytosolic 85-kDa phospholipase camptothecin chloroquine-resistant Plasmodium falciparum chloroquine-resistant Plasmodium falciparum FcM29 chloroquine-sensitive Plasmodium falciparum aromatase cytochrome P450 1A cytochrome P450 1A cytochrome P450 1A day diameter (mm) difference in log10 GI50 (mol/L) value of the most sensitive cell line and MGMID value diacylglycerol acyltransferase dihydrofolate reductase dimethyl sulfoxide deoxyribonucleic acid doxorubicin diphenylene indonium 1,1-diphenyl-2-picrylhydrazyl free radical

List of Abbreviations and Acronyms

DRPF DRS DSPF DYRK1A EBV EC EC50 ED50 ED50 EGF EGFR EL-4 ELISA EPI ERK ESBLs EurJOC FAK FBS FLT3 Flu-A Flu-B fMLP/CB FOXO1a fp FPT FRCA FtsZ FXR GABA GI50 GlyR gp41 gpg GPR12 GRP78 GST GTP GU4 GU5 h H1N1 H3N2 H5N1 HBV HC50 HCMV

XXV

drug-resistant Plasmodium falciparum drug-resistant Staphylococcus sp. drug-sensitive Plasmodium falciparum protein kinase Epstein–Barr virus effective concentration medium effective concentration effective dose for 50% medium effective dose (sometimes for the medium effective concentration) epidermal growth factor epidermal growth factor receptor lymphoma cell line with resistance to natural killer cells enzyme-linked immunosorbent assay epirubicin extracellular signal-regulated protein kinase extended spectrum β-lactamase further abbreviation on Eur. J. Org. Chem. protein kinase fetal bovine serum a protein tyrosine kinase influenza virus type A influenza virus type B N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B downstream target of PTEN tumor suppressor freezing point farnesyl protein transferase fluconazole-resistant Candida albicans A structural homolog of eukaryotic tubulin, a GTPase farnesoid X receptor γ-aminobutyric acid the concentration of sample necessary to inhibit the growth to 50% of the control glycine-gated chloride channel receptor a transmembrane protein of HIV-1 (recombinant protein) guinea pig G protein-coupled receptor 12; it can be a significant molecular target for treating a variety of neurological disorders molecular chaperone (chaperone) glutathione S-transferases guanosine triphosphate Candida albicans-sensitive GU4 strain Candida albicans-resistant GU5 strain hour influenza virus H1N1 influenza virus H3N2 influenza virus A H5N1 hepatitis B virus medium hemolytic concentration hmn cytomegalovirus

XXVI

HCV HD HER2 HF HIF-1 HIV HIV-1 HIV-1 IIIB HIV-1 in HIV-1 RF HIV-1-rt HIV-2 HIV-rt HLE HMG-CoA hmn HNE HO• hPPARd HSV HSV-1 HSV-2 hTopo l HXB2 IC IC50 IC90 IC100 ICR ID ID50 IDE IDO IFV IgE IGF1-R IgM IL IL-1 IL-1α IL-1β IL-2 IL-4 IL-5 IL-6 IL-8 IL-12 IL-13

List of Abbreviations and Acronyms

hepatitis C virus a positive control compound; no concrete explanation in original paper (J. Qin, et al., BoMCL, 2010, 20, 7152) tyrosine kinase hypersensitivity factor hypoxia-inducible factor-1 hmn immunodeficiency virus hmn immunodeficiency virus type 1 hmn immunodeficiency virus type 1 IIIB hmn immunodeficiency virus type 1 integrase hmn immunodeficiency virus RF hmn immunodeficiency virus type 1 reverse transcriptase hmn immunodeficiency virus type 2 hmn immunodeficiency virus reverse transcriptase hmn leukocyte elastase 3-hydroxy-3-methylglutaryl coenzyme A reductase human hmn neutrophil elastase hydroxyl radical hmn peroxisome proliferator-activated receptor delta herpes simplex virus herpes simplex virus 1 herpes simplex virus 2 hTopo l isomerase T-cell tropic viral strain inhibiting concentration median inhibiting concentration inhibiting concentration for 90% absolute inhibiting concentration imprinting control region mouse inhibition diameter (mm) median inhibiting dose insulin-degrading enzyme indoleamine 2,3-dioxygenase influenza virus immunoglobulin E protein kinase immunoglobulin M interleukin interleukin-1 interleukin-1α interleukin-1β interleukin-2 interleukin-4 interleukin-5 interleukin-6 interleukin-8 interleukin-12 interleukin-13

List of Abbreviations and Acronyms

IM IMPDH IN iNOS InRt ip iv IZ IZD IZR JACS Jak2 JCS Perkin I JMC JNK JNP JOC KDR KU-812 LAV LC50 LCV LD LD100 LD50 LD99 LDH LOX LPS LTB4 LTC4 LY294002 MABA MAGI test MAPKAPK-2 MAPKK MBC MBC90 MBEC90 MCV MDR MDR1 MDRPF MDRSA MDRSP MEK1 wt MET wt

XXVII

immunomodulator inosine monophosphate dihydrogenase integrase inducible nitric oxide synthase inhibitive rate intraperitoneal injection intravenous injection inhibition zone (mm) inhibition zone diameter (mm) inhibition zone radii (mm) further abbreviation on J. Am. Chem. Soc. Janus kinase 2 further abbreviation on J. Chem. Soc., Perkin Trans. I further abbreviation on J. Med. Chem. c-Jun NH2-terminal kinase further abbreviation on J. Nat. Prod. further abbreviation on J. Org. Chem. a protein tyrosine kinase hmn basophilic granulocyte T-cell tropic viral strain concentration at which only 50% of the cells are viable lymphocyte viability lethal dose 100% lethal dose medium lethal dose 99% lethal dose lactate dehydrogenase lipoxygenase lipopolysaccharide leukotriene B4 leukotriene C4 phosphatidylinositol-3-kinase inhibitor; used as a positive control in anti-inflammatory assay microplate Alamar blue assay also called single life cycle test, reflects only one round of infection mitogen-activated protein kinase-activated protein kinase 2 mitogen-activated protein kinase kinase minimum bactericidal concentration minimum bactericidal concentration for 90% minimum biofilm eradication counts for 90% poxvirus Molluscum contagiosum virus multidrug resistance major facilitator superfamily 1; one type of efflux pump in C. albicans, which functions as an H+-antiporter multidrug-resistant Plasmodium falciparum multidrug-resistant Staphylococcus aureus multidrug-resistant Streptococcus pneumoniae protein kinase protein kinase

XXVIII

MG-MID MIA MIC MIC50 MIC80 MIC90 MID min MLD MLR MMOA MMP MMP-2 MoBY-ORF mp MPtpA MPtpB mPTPB MREC MRSA MRSE MSR MSSA MSSE MT1-MMP MT4 MTT MTT assay mus n nACh NADH NDM-1 NEK2 NEK6 NF-κB

NFRD NGF NMDA NO• NPR O2•− ONOO− ORAC orl p24

List of Abbreviations and Acronyms

mean value of log10 GI50 (mol/L) over all cell lines tested minimal inhibitory amounts (μg/disk) minimum inhibitory concentration minimal inhibitive concentration for 50% minimal inhibitive concentration for 80% minimal inhibitive concentration for 90% minimum inhibitory dose minute minimum lethal dose mixed lymphocyte reaction molecular mechanism of action matrix metalloproteinases matrix metalloproteinase-2 molecular barcoded yeast open-reading frame library method melting point mycobacterial protein tyrosine phosphatase A mycobacterial protein tyrosine phosphatase B Mycobacterium tuberculosis protein tyrosine phosphatase B methicillin-resistant Escherichia coli methicillin-resistant Staphylococcus aureus methicillin-resistant Staphylococcus epidermidis macrophage scavenger receptor methicillin-sensitive Staphylococcus aureus methicillin-sensitive Staphylococcus epidermidis membrane type 1 matrix metalloproteinase MT4 cells containing HIV-1 IIIB virus 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide A cytotoxicity measurement method, tetrazolium-based colorimetric assay; see L. V. Rubinstein, et al., Nat. Cancer Inst., 82, 1113–1118 (1990) mouse number of parallel experiments nicotinic acetylcholine reduced nicotinamide adenine dinucleotide New Delhi metallo-β-lactamase-1 protein kinase protein kinase NF-κB serves as a central regulator of hmn immune, inflammatory, and antiapoptotic responses (Ghosh et al., 1998, Ann. Rev. Immunol, 16, 225–260) NADH-fumarate reductase nerve growth factor N-methyl-D-aspartate nitric oxide free radical further abbreviation on Nat. Prod. Rep. superoxide free radical peroxy nitrite free radical oxygen radical absorbance capacity oral p24 protein

List of Abbreviations and Acronyms

P2Y receptors P2Y11 receptor P450 p56lck PAcF PAF PD pD2 (=pEC50) PDE5 PDGF PfGSK-3 Pfnek-1 PfPK5 PfPK7 PGE2 PHK PIM1 PK PKA PKC PKC-ε PKD PKG PLA PLA2 PLCγ1 PLK1 PM PMA (=TPA) PMNL PP PP1 PP2A pp60V-SRC PPAR PPDK PR PRK1 PRNG PRSP PTEN PTK PTP1B PTPB PTPS2

XXIX

one type of purine receptors, which includes P1 (adenosine receptors) and P2 receptors [ionotropic P2X and metabotropic (G protein-coupled) P2Y] one of eight P2Y subtypes cytochrome P450 tyrosine kinase platelet activating factor platelet aggregation factor Parkinson’s disease negative logarithm (−log M) of molar concentration required to produce 50% of the maximum response (EC50) phosphodiesterase 5 platelet-derived growth factor kinase a NIMA-related protein kinase of Plasmodium falciparum kinase kinase prostaglandin E2 primary hmn keratinocytes protein kinase protein kinase protein kinase A protein kinase C protein kinase C-ε ribosomal protein protein kinase G phospholipase A phospholipase A2 ribosomal protein protein kinase further abbreviation on Planta Med. phorbol-12-myristate-13-acetate hmn polymorphonuclear leukocyte protein phosphatase protein phosphatase PP1 protein phosphatase PP2A tyrosine kinase peroxisome proliferator-activated receptor pyruvate phosphate dikinase protease protein kinase penicillin-resistant Neisseria gonorrhoeae penicillin-resistant Staphylococcus pneumoniae tumor suppressor, an identified tumor suppressor gene located on hmn chromosome 10q23.3 protein tyrosine kinase protein tyrosine phosphatase 1B, an important target for treatment of type II diabetes protein tyrosine phosphatase B protein tyrosine phosphatase S2

XXX

List of Abbreviations and Acronyms

PV-1 PXR QR Range rat rbt RLAR RNA ROS RS321 RSV RT RU RyR1-FKBP12 S6 SAK SARS ScRt SF162 SI SI SI SI SI SIRT2

sp. spp. SR SRB SRC SV40 Syn. T/C TACE Taq DNA polymerase TBARS TC50 TEAC TGI TMV TNFα TPA (=PMA)

Polio virus pregnane X receptor NAD(P)H: quinone reductase difference in log10 GI50 (mol/L) value of the most sensitive cell line and the least sensitive cell white rat rabbit rat lens aldose reductase ribonucleic acid reactive oxygen species (involved in genesis of various cancers, arteriosclerosis, rheumatism, and aging) code of a yeast respiratory syncytial virus reverse transcriptase response unit of binding capacity to HIV-1 targets, 1 RU = 1 pg/mm2 RyR1–FKBP12 Ca2+ channel, a tetrameric heterodimeric channel protein (~2000 kDa) associated with smaller 12 kDa immunophilin FKBP12 ribosomal protein a protein kinase severe acute respiratory syndrome scavenging rate macrophage-tropic viral strain IC50 of testing cells/IC50 of HUVECs selective index = cytotoxic CC50/target EC50 selective index = cytotoxic IC50/target IC50 selective index = cytotoxic IC50/target MIC selective index = cytotoxic TC50/target IC50 hmn sirtuin type 2 (a NAD+-dependent cytoplasmic protein that is colocalized with HDAC6 on microtubules. SIRT2 has been shown to deacetylate α-tubulin and to control mitotic exit from the cell cycle) species species (plural) sarcoplasmic reticulum sulforhodamine B assay protein kinase SV40 virus synonym survival ratio [survival time of treated animal (T) was compared to that of control animal (C) expressed as a percent (T/C%)] α-secretase (a serine protease) a DNA polymerase isolated from the thermophilic bacterium Thermus aquaticus thiobarbituric acid-reactive substance assay 50% cytotoxic concentration Trolox equivalent antioxidant capacity 100% growth inhibition tobacco mosaic virus tumor necrosis factor-α 12-O-tetradecanoyl phorbol 13-acetate

List of Abbreviations and Acronyms

TPK TRP TRPA1 TRPV1 TRPV3 TXB2 TZM-bl USP7 VCAM VCAM-1 VCR VEGF VEGF-A VEGFR2 VE-PTP VGSC VHR Vif VP-16 VRE VREF VSE VSSC VSV WST-8 XTT YU2-V3

XXXI

tyrosine protein kinase transient receptor potential cationic channel transient receptor potential cationic channel of subfamily A1 transient receptor potential cationic channel of subfamily V1 transient receptor potential cationic channel of subfamily V3 thromboxane B2 host cell in HIV-1 neutralization assay a deubiquitylating enzyme hydrolyzing isopeptide bond at C-terminus of ubiquitin, is an emerging cancer target vascular cell adhesion molecule vascular cell adhesion molecule-1 vincristine vascular endothelial growth factor vascular endothelial growth factor A tyrosine kinase VEGFR2 protein phosphatase voltage-gated sodium channel vaccinia open-reading frame H1-related protein phosphatase viral infectivity factor of HIV-1 etoposide (Sigma product), a positive control for cytotoxic assay vancomycin-resistant Enterococcus sp. vancomycin-resistant Enterococcus faecium vancomycin-sensitive Enterococcus sp. voltage sensitive sodium channel Vesicular stomatitis virus 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfo-phenyl)2H-tetrazolium, monosodium salt sodium 3′-[1-(phenylaminocarbonyl)-3,4-tetrazolium] bis(4-methoxy-6nitrobenzene)sulfonic acid viral strain

List of Cancer Cell Codes This set of codes for 438 cancer cells, named as CCC codes, are defined and tried out in the books by the author. The codes of some normal cells are also listed below. 293T 3T3-L1 5637 786-0 9KB A-10 A2058 A278 A2780 A2780CisR A2780/DDP A2780/Tax A375 A375-S2 A431 A498 A549 A549 NSCL A549/ATCC ACC-MESO-1 ACHN AGS AsPC-1 B16 B16F1 B16-F-10 BC BC-1 BCA-1 BEAS2B Bel7402 BG02 BGC823 BOWES BR1 BSC BSC-1 BSY1 BT-483 BT549 BT-549 BXF-1218L BXF-T24 BXPC

kidney epithelial cells murine fibroblasts superficial bladder cancer (cell) hmn renal cancer (cell) hmn epidermatoid nasopharyngeal carcinoma (cell) rat aorta cells hmn (cell) hmn ovarian tumor (cell) hmn ovarian tumor (cell) hmn ovarian tumor (cell) hmn ovarian tumor (cell) hmn ovarian tumor (cell) hmn melanoma (cell) hmn melanoma (cell) hmn epidermic cancer (cell) hmn renal cancer (cell) hmn nonsmall cell lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn malignant pleural mesothelioma (cell) hmn renal cancer (cell) gastric adenocarcinoma (cell) hmn pancreatic cancer (cell) mouse melanoma (cell) mouse melanoma (cell) mouse melanoma (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) normal hmn lung bronchial cells hmn liver cancer (cell) normal hmn embryonic stem cells hmn gastric cancer (cell) hmn cells DNA repair competent Chinese hamster ovary (cell) normal monkey kidney cells normal African Green Monkey kidney cells breast cancer (cell) hmn breast carcinoma (cell) hmn galactophore cancer (cell) hmn breast cancer (cell) hmn bladder cancer (cell) hmn bladder cancer (cell) hmn pancreas cancer (cell)

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XXXIV

BXPC3 C6 C26 C38 CA46 Ca9-22 CaCo-2 CAKI-1 Calu Calu3 CCRF-CEM CCRF-CEMT CEM CEM-TART CFU-GM CHO CHO-K1 CML K562 CNE CNE2 CNS SF295 CNXF-498NL CNXF-SF268 Colo320 Colo357 Colon26 Colon38 Colon205 Colon250 CV-1 CXF-HCT116 CXF-HT29 DAMB DG-75 DLAT DLD-1 DLDH DMS114 DMS273 Doay Dox40 DU145 DU4475 E39 EAC EKVX EM9 EMT-6 EPC

List of Cancer Cell Codes

hmn pancreas cancer (cell) rat glioma (cell) hmn colon carcinoma (cell) murine colon adenocarcinoma (cell) hmn Burkitt’s lymphoma (cell) hmn gingival carcinoma (cell) hmn epithelial colorectal adenocarcinoma (cell) hmn renal cancer (cell) prostate carcinoma (cell) nonsmall cell lung cancer (cell) hmn T-cell acute lymphoblastic leukemia (cell) leukemia (cell) hmn leukemia (cell) T cells that express both HIV-1 tat and rev hmn/murine hematopoietic progenitor cells Chinese hamster ovary cells subclone of normal Chinese hamster ovary cells chronic myelogenous leukemia (cell) hmn nasopharyngeal carcinoma (cell) hmn nasopharyngeal carcinoma (cell) hmn brain tumor (cell) hmn glioblastoma cancer (cell) hmn glioblastoma cancer (cell) hmn colorectal cancer (cell) hmn colorectal cancer (cell) colorectal cancer (cell) mus colorectal cancer (cell) colorectal cancer (cell) colorectal cancer (cell) monkey kidney fibroblasts hmn colon cancer (cell) hmn colon cancer (cell) hmn mammary carcinoma (cell) hmn B lymphocyte (cell) Dalton’s lymphoma ascites tumor (cell) hmn colorectal adenocarcinoma (cell) hmn colorectal adenocarcinoma (cell) hmn lung cancer (cell) hmn small cell lung cancer (cell) hmn medulloblastoma (cell) hmn myeloma (cell) prostate cancer (cell) breast cancer (cell) hmn renal carcinoma (cell) Ehrlich ascites carcinoma (cell) hmn nonsmall cell lung cancer (cell) topoisomerase I-sensitive Chinese hamster ovary (cell) mouse tumor cells carp epithelium (cell)

List of Cancer Cell Codes

EVLC-2 F1 FADU Farage Fem-X Fl FM3C G402 GM7373 GR-III GXF-251L H116 H125 H441 H460 H522 H1299 H1325 H1975 H2122 H2887 H69AR H929 H9c2 HBC4 HBC5 HBL100 HCC366 HCC2998 HCC-S102 HCT HCT8 HCT15 HCT29 HCT116 HCT116/mdr+ HCT116/topo HCT116/VM46 HEK-293 HEL HeLa HeLa-APL HeLa-S3 Hep2 Hep3B HepA Hepa1c1c7 HepG HepG2

SV40 large T-antigen immortalized hmn umbilical vein cells hmn amniotic epithelial cells pharynx-sq cancer (cell) hmn lymphoma (cell) melanoma (cell) hmn amniotic epithelial cell line mus mammary tumor (cell) hmn renal leiomyoblastoma bovine endothelial (cell) adenocarcinoma (cell) hmn stomach cancer (cell) hmn colorectal cancer (cell) hmn colorectal cancer (cell) hmn lung adenocarcinoma (cell) hmn lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn lung adenocarcinoma (cell) hmn nonsmall cell lung cancer (cell) hmn cancer (cell) hmn nonsmall cell lung cancer (cell) hmn nonsmall cell lung cancer (cell) multidrug-resistant small cell lung cancer (cell) hmn myeloma (cell) rat cardiac myoblasts breast cancer (cell) breast cancer (cell) breast cancer (cell) hmn nonsmall cell lung cancer (cell) hmn colorectal cancer (cell) hepatocellular carcinoma (cell) hmn colorectal cancer (cell) hmn colorectal cancer (cell) hmn colorectal cancer (cell) hmn colon adenocarcinoma (cell) hmn colorectal cancer (cell) overexpress mdr+ hmn colorectal cancer (cell) resistant to etoposide hmn colorectal cancer (cell) multidrug-resistant colorectal cancer (cell) normal hmn epithelial kidney cells hmn embryonic lung fibrocytes hmn cervical epithelial carcinoma (cell) hmn cervical epithelial cancer (cell) hmn cervical epithelial cancer (cell) hmn liver carcinoma (cell) hmn liver cancer (cell) hmn liver cancer ascites (cell) mus liver cancer (cell) hmn liver cancer (cell) hmn liver cancer (cell)

XXXV

XXXVI

HepG3 HepG3B HEY HFF HL60 HL7702 HLF HM02 HMEC HMEC1 HNXF-536L HOP-18 HOP-62 HOP-92 Hs578T Hs683 HSV-1 HT HT29 HL60 HT115 HT460 HT1080 HTC116 HTCLs HuCCA-1 Huh7 HUVEC HUVECs IC-2WT IGR-1 IGROV IGROV1 IGROV-ET IMR-32 IMR-90 J774 J774.1 J774.A1 JB6 CI41 JB6 P+CI41 JurKat JurKat-T K462 K562 KB KB16 KB-3 KB-3-1

List of Cancer Cell Codes

hmn liver cancer (cell) hmn liver cancer (cell) hmn ovarian carcinoma (cell) hmn foreskin fibroblasts hmn promyelocytic leukemia (cell) hmn liver tumor (cell) hmn lung fibroblasts hmn gastric adenocarcinoma (cell) hmn microvascular endothelial cells hmn microvascular endothelial cells hmn head and neck cancer (cell) hmn nonsmall cell lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn breast cancer (cell) hmn oligodendroglioma (black dots) (cell) nonmalignant cell hmn lymphoma (cell) hmn colorectal cancer (cell) M. Daferner et al., Z. Naturforsch., Teil C, 1999, 54, 474 hmn colorectal cancer (cell) hmn tumor (cell) hmn fibrosarcoma (cell) hmn acute promyelocytic leukemia (cell) hmn tumors (cells) hmn cholangiocarcinoma cancer (cell) hmn hepatoma (cell) hmn umbilical vein endothelial cell hmn umbilical vein endothelial cell murine cell line hmn melanoma (cell) hmn ovarian cancer (cell) hmn ovarian cancer (cell) hmn ovarian cancer (cell) hmn neuroblastoma (cell) hmn diploid lung fibroblasts mus monocyte/macrophage (cell) mus monocyte/macrophage (cell) mus monocyte/macrophage (cell) mouse epidermal cells mouse epidermal cells hmn leukemia (cell) hmn T-cell leukemia (cell) hmn leukemia (cell) hmn chronic myelogenous leukemia (cell) hmn nasopharyngeal carcinoma (cell) hmn nasopharyngeal carcinoma (cell) hmn epidermoid carcinoma (cell) hmn epidermoid carcinoma (cell)

List of Cancer Cell Codes

KB-C2 KB-CV60 KBV200 Ketr3 KM12 KM20L2 KMS34 KU812F KV/MDR KYSE30 KYSE70 KYSE180 KYSE520 L1210 L1210/Dx L363 L-428 L5178 L5178Y L-6 L929 LLC-PK1 LMM3 LNCaP LO2 LoVo LoVo-DOX LOX LOX-IMVI LX-1 LXF-1121L LXF-289L LXF-526L LXF-529L LXF-629L LXFA-629L LXF-H460 M14 M16 M17 M17-Adr M21 M5076 MAGI MALME-3 MALME-3M MAXF-401 MAXF-401NL MAXF-MCF7

hmn carcinoma (cell) hmn carcinoma (cell) MDR nasopharyngeal carcinoma (cell) hmn renal cancer (cell) hmn colorectal cancer (cell) hmn colorectal cancer (cell) hmn myeloma (cell) hmn leukemia (cell) multidrug-resistant cancer (cell) hmn esophageal cancer (cell) hmn esophageal cancer (cell) hmn esophageal cancer (cell) hmn esophageal cancer (cell) mouse lymphocytic leukemia (cell) doxorubicin-resistant L1210 (cell) hmn myeloma (cell) leukemia (cell) mouse lymphosarcoma (cell) mouse lymphosarcoma (cell) rat skeletal myoblasts (cell) mouse fibroblasts pig kidney cells mouse mammary adenocarcinoma (cell) hmn prostate cancer (cell) hmn liver cells hmn colorectal cancer (cell) hmn colorectal cancer (cell) hmn melanoma (cell) hmn melanoma (cell) hmn lung cancer (cell) hmn lung cancer (cell) hmn lung cancer (cell) hmn lung cancer (cell) hmn lung cancer (cell) hmn lung cancer (cell) lung adenocarcinoma (cell) hmn lung cancer (cell) melanoma (cell) murine colon adenocarcinoma (cell) adriamycin-resistant breast cancer (cell) adriamycin-resistant breast cancer (cell) melanoma (cell) ovarian sarcoma (cell) Hela-CD4-LTR-β-gal (indicator) cells containing HIV-1 IIIB virus melanoma (cell) melanoma (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell)

XXXVII

XXXVIII

List of Cancer Cell Codes

MCF MCF-10A MCF7 MCF7 Adr MCF7/Adr MCF7/ADR-RES MCF12 MDA231 MDA361 MDA435 MDA468 MDA-MB MDA-MB-231 MDA-MB-231/ATCC MDA-MB-435 MDA-MB-435s MDA-MB-468 MDA-N MDCK ME180 MEL28 MES-SA MES-SA/DX5 MEXF-276L MEXF-394NL MEXF-462NL MEXF-514L MEXF-520L MG63 MGC-803 MiaPaCa Mia-PaCa-2 MKN1 MKN7 MKN28 MKN45 MKN74 MM1S Molt3 Molt4 Mono-Mac-6 MPM ACC-MESO-1 MRC-5 MRC5CV1 MS-1 MX-1 N18-RE-105 N18-T62 NAMALWA

hmn breast cancer (cell) hmn breast epithelial (cell) hmn breast cancer (cell) drug-resistant hmn breast MCF7 cancer (cell) drug-resistant hmn breast MCF7 cancer (cell) drug-resistant hmn breast cancer MCF7 (cell) hmn esophageal cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) hmn breast cancer (cell) Madin–Darby canine (cell) cervical cancer (cell) hmn melanoma (cell) hmn uterine (cell) hmn uterine (cell) hmn melanoma (cell) hmn melanoma (cell) hmn melanoma (cell) hmn melanoma (cell) hmn melanoma (cell) hmn osteosarcoma (cell) hmn cancer (cell) hmn pancreas cancer (cell) hmn pancreas cancer (cell) hmn gastric cancer (cell) hmn gastric cancer (cell) hmn gastric cancer (cell) hmn gastric cancer (cell) hmn gastric cancer (cell) hmn myeloma (cell) leukemia (cell) hmn T lymphocyte leukemia (cell) mononuclear cells hmn malignant pleural mesothelioma normal hmn diploid embryonic cells SV40-transformed hmn fibroblasts mice endothelial cells hmn mammary carcinoma xenografts neuronal hybridoma (cell) mus neuroblastoma (cell) leukemia (cell)

List of Cancer Cell Codes

NBT-T2 (BRC-1370) NCI-ADR NCI-ADR-Res NCI-H23 NCI-H69 NCI-H82 NCI-H187 NCI-H226 NCI-H322M NCI-H446 NCI-H460 NCI-H510 NCI-H522 neuro-2a NFF NHDF NIH3T3 NIH3T3 NMuMG NOMO-1 NS-1 NSCLC NSCLC HOP-92 NSCLC-L16 NSCLC-N6 NSCLC-N6-L16 NUGC-3 OCILY17R OCIMY5 OPM2 OVCAR-3 OVCAR-4 OVCAR-5 OVCAR-8 OVXF-1619L OVXF-899L OVXF-OVCAR3 P388 P388/ADR P388/Dox P388D1 PANC1 panc89 PAXF-1657L PAXF-PANC1 PBMC PC12 PC-12 PC3

rat bladder epithelial cells hmn ovarian sarcoma (cell) hmn ovarian sarcoma (cell) hmn nonsmall cell lung cancer (cell) hmn lung cancer (cell) hmn lung cancer (cell) hmn small cell lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn lung cancer (cell) hmn nonsmall cell lung cancer (cell) hmn lung cancer (cell) hmn nonsmall cell lung cancer (cell) mouse neuroblastoma (cell) nonmalignant neonatal foreskin fibroblasts normal hmn dermal fibroblasts nontransformed fibroblasts normal fibroblasts nontransformed epithelial cells hmn acute myeloid leukemia murine cells hmn bronchopulmonary nonsmall cell lung cancer hmn nonsmall cell lung cancer (cell) hmn bronchopulmonary nonsmall cell lung carcinoma hmn bronchopulmonary nonsmall cell lung cancer (cell) hmn bronchopulmonary nonsmall cell lung carcinoma hmn gastric cancer (cell) hmn lymphoma (cell) hmn myeloma (cell) hmn myeloma (cell) ovarian adenocarcinoma (cell) ovarian adenocarcinoma (cell) ovarian adenocarcinoma (cell) ovarian adenocarcinoma (cell) ovary cancer (cell) ovary cancer (cell) ovary cancer (cell) mus lymphocytic leukemia (cell) P388 adriamycin-resistant (cell) mus leukemia cells expressing resistance toward doxorubicin mus macrophage cells hmn pancreas cancer (cell) pancreatic cancer (cell) hmn pancreas cancer (cell) hmn pancreas cancer (cell) hmn normal peripheral blood mononuclear cells hmn lung cancer (cell) rat pheochromocytoma (cell) hmn prostate cancer (cell)

XXXIX

XL

List of Cancer Cell Codes

PC3M PC3MM2 PC-9 PRXF-22RV1 PRXF-DU145 PRXF-LNCAP PRXF-PC3M PS (=P388) PV1 PXF-1752L QG56 QGY-7701 QGY-7703 Raji RAW264.7 RB RBL-2H3 RF-24 RKO RKO-E6 RPMI7951 RPMI8226 RXF-1781L RXF-393 RXF-393NL RXF-486L RXF-631L RXF-944L S180 S180A SAS SCHABEL SF268 SF295 SF539 SGC7901 SH-SY5Y SK5-MEL SKBR3 SK-Hep1 SK-MEL-2 SK-MEL-5 SK-MEL-28 SK-MEL-S SK-N-SH SK-OV-3 SMMC-7721

hmn prostate cancer (cell) hmn prostate cancer (cell) hmn lung cancer (cell) hmn prostate cancer (cell) hmn prostate cancer (cell) hmn prostate cancer (cell) hmn prostate cancer (cell) PS system, P388 mouse lymphocytic leukemia (cell) nonmalignant cell mesothelioma cancer (cell) hmn lung carcinoma (cell) hmn hepatocellular carcinoma (cell) hmn liver cancer (cell) hmn EBV-transformed Burkitt’s lymphoma B cell mouse macrophages hmn prostate cancer (cell) rat basophilic cells papillomavirus 16 E6/E7 immortalized hmn umbilical vein cells hmn colon cancer (cell) hmn colon cancer (cell) hmn malignant melanoma (cell) hmn myeloma (cell) renal cancer (cell) renal cancer (cell) renal cancer (cell) renal cancer (cell) renal cancer (cell) renal cancer (cell) mouse sarcoma (cell) sarcoma 180 ascites cells hmn oral cancer mouse lymphoma cancer (cell) hmn brain tumor (cell) hmn brain tumor (cell) hmn brain tumor (cell) hmn gastric cancer (cell) hmn neuroblastoma (cell) hmn melanoma (cell) hmn breast cancer (cell) hmn liver carcinoma (cell) hmn melanoma (cell) hmn melanoma (cell) hmn melanoma (cell) hmn melanoma (cell) neuroblastoma (cell) ovarian adenocarcinoma (cell) hmn liver cancer (cell)

List of Cancer Cell Codes

SN12C SN12k1 SNB19 SNB75 SNB78 SNU-C4 SR St4 stromal cell SUP-B15 Sup-T1 SW480 SW620 SW1573 SW1736 SW1990 T24 T-24 T47D THP-1 TK10 tMDA-MB-231 tsFT210 TSU-Pr1 TSU-Pr1-B1 TSU-Pr1-B2 U251 U266 U2OS U373 U373MG U-87-MG U937 UACC-257 UACC62 UO-31 UT7 UV20 UXF-1138L V79 Vero WEHI-164 WHCO1 WHCO5 WHCO6 WI26 WiDr

hmn renal cancer (cell) hmn renal cancer (cell) hmn brain tumor (cell) hmn CNS cancer (cell) hmn brain tumor (cell) hmn cancer (cell) leukemia (cell) gastric cancer (cell) bone marrow stromal cells leukemia (cell) T-cell lymphoma cancer cells hmn colorectal adenocarcinoma (cell) hmn colorectal adenocarcinoma (cell) hmn nonsmall cell lung cancer (cell) hmn thyroid cancer (cell) hmn pancreatic cancer (cell) hmn liver cancer (cell) hmn transitional bladder carcinoma (cell) hmn breast cancer (cell) hmn acute monocytic leukemia (cell) hmn renal cancer (cell) hmn breast cancer (cell) mouse cancer (cell) invasive bladder cancer (cell) invasive bladder cancer (cell) invasive bladder cancer (cell) CNS tumor/glioma (cell) myeloma (cell) hmn osteosarcoma (cell) glioblastoma/astrocytoma (cell) hmn brain cancer (cell) caucasian glioblastoma (cell) hmn monocytic leukemia (cell) melanoma (cell) melanoma (cell) hmn renal cancer (cell) hmn leukemia (cell) DNA cross-linking agent sensitive Chinese hamster ovary (cell) hmn uterus cancer (cell) Chinese hamster (cell) green monkey kidney tumor (cell) mus fibrosarcoma (cell) hmn esophageal cancer (cell) hmn esophageal cancer (cell) hmn esophageal cancer (cell) hmn lung fibroblasts hmn colon adenocarcinoma (cell)

XLI

XLII

WMF XF498 XRS-6 XVS ZR-75-1

List of Cancer Cell Codes

hmn prostate cancer (cell) hmn CNS cancer (cell) topoisomerase II-sensitive Chinese hamster ovary (cell) topoisomerase II-sensitive CHO cell hmn breast cancer (cell)

3 Diterpenoids (continuing) 3.19 Dolabellane Diterpenoids 1 5-Acetoxy-10,18-dihydroxy-2,7-dolabelladiene Type: Dolabellane diterpenoids. C22H36O4 [α]D25 = −6.7° (c = 0.15, CHCl3). Source: Brown alga Dictyota dichotoma (Cádiz, Spain). Pharm: Cytotoxic (P388, ED50 = 5 μg/mL, A549, ED50 = 5 μg/mL, HT29, ED50 = 5 μg/mL, MEL28, ED50 = 5 μg/mL). Ref: R. Durán, et al, Tetrahedron, 1997, 53, 8675 O H

HO

O

HO

2 18-Acetoxy-dolabelladiene Type: Dolabellane diterpenoids. C22H36O2 [α]D25 = −53.2° (c = 0.41, CHCl3). Source: Brown alga Dictyota dichotoma (Cádiz, Spain). Pharm: Cytotoxic (P388, ED50 = 5 μg/mL, A549, ED50 = 5 μg/mL, HT29, ED50 = 5 μg/mL, MEL28, ED50 = 5 μg/mL). Ref: R. Durán, et al, Tetrahedron, 1997, 53, 8675 O H

O

3 3-Acetoxy-4E,8,18-dolabellatrien-16-al Type: Dolabellane diterpenoids. C22H32O3 Viscous oil, [α]D = +9.7° (c = 1.2, EtOH). Source: Brown alga Dictyota sp. Pharm: Molluscacidal. Ref: C. Tringali, et al, Tetrahedron, 1984, 40, 799│ C. Tringali, et al, JNP, 1984, 47, 615│ C. Tringali, et al, Phytochemistry, 1984, 23, 1681 H

O O

O

https://doi.org/10.1515/9783110655155-001

2

3 Diterpenoids

4 16-Acetoxy-7,8-epoxy-3,12(18)-dolabelladien-13-one Type: Dolabellane diterpenoids. C22H32O4 Glass, [α]D24 = +40° (c = 4.5). Source: Gorgonian Eunicea tourneforti. Pharm: Antifungal (RS321 Inhibitor, IC12 > 1800 μg/mL). Ref: M. Govindan, et al, JNP, 1995, 58, 1174 H O

O

O O

5 6-Acetoxy-7,8-epoxy-3,12-dolabelladien-13-one Type: Dolabellane diterpenoids. C22H32O5 [α]D24 = +90° (c = 6). Source: Gorgonian Eunicea tourneforti. Pharm: Antifungal（RS321 Inhibitor, IC12 > 3000 μg/mL). Ref: M. Govindan, et al, JNP, 1995, 58, 1174 H O

O

O

O OH

6 18-Acetoxy-10-hydroxy-2,7-dolabelladiene Type: Dolabellane diterpenoids. C22H36O3 [α]D25 = −36.2° (c = 0.47, CHCl3). Source: Brown alga Dictyota dichotoma (Cádiz, Spain). Pharm: Cytotoxic (P388, ED50 = 1.2 μg/mL, A549, ED50 = 1.2 μg/mL, HT29, ED50 = 2.5 μg/mL, MEL28, ED50 = 2.5 μg/mL). Ref: R. Durán, et al, Tetrahedron, 1997, 53, 8675 O O

H HO

7 Claenone (3R,4R,7E)-3,4-Epoxy-7,12(18)-dolabelladien-13-one Type: Dolabellane diterpenoids. C20H30O2 Needles (hexane/EtOAc), mp 124–126 °C, [α]D = −50.9° (c = 1.20, CHCl3). Source: Stolonifer Clavularia sp. (Okinawa). Pharm: Cytotoxic (WMF, GI50 = 2.42 × 10‒7mol/L, RB cells, GI50 = 3.06 × 10‒7 mol/L); inhibits cell division

3.19 Dolabellane Diterpenoids

3

(fertilized sea urchin eggs). Ref: K. Mori, et al, CPB, 1988, 36, 2840│ H. Miyaoka, et al, Tet. Lett., 1998, 39, 6503 O O H

H

8 Clavirolide A (3E,10β,11β)-11-Hydroxy-6-oxo-3,12(18)-dolabelladien-19,10-olide Type: Dolabellane diterpenoids. C20H28O4 Cryst., mp 188–190 °C, [α]D = −328.8° (c = 0.22, CHCl3). Source: Stolonifer Clavularia viridis (South China Sea). Pharm: Cytotoxic (EAC, ED50 = 8 μg/mL). Ref: J. Su, et al, JNP, 1991, 54, 380│ J. Su, et al, JOC., 1991, 56, 2337 O O

OH

O

9 Clavirolide B Type: Dolabellane diterpenoids. C20H28O3 Plates (Me2CO/petrol), mp 143.5–145.5 °C, [α]D26.5 = −392.7° (c = 0.085, MeOH). Source: Stolonifer Clavularia viridis (Xisha Is., South China Sea, China). Pharm: Cytotoxic (EAC, ED50 = 21.0 μg/mL); calcium channel blocker (rbt, isolated smooth muscle, PD’2 = 4.68 μg/mL). Ref: J. Su, et al, JNP, 1991, 54, 380

4 3

H

O

O

O

10 Clavirolide C Type: Dolabellane diterpenoids. C20H30O3 Cryst., mp 124.5–126.5 °C, [α]D26.5 = −38.5° (c = 0.018, MeOH). Source: Stolonifer Clavularia viridis (Xisha Is., South China Sea,

4

3 Diterpenoids

China). Pharm: Cytotoxic (EAC, ED50 = 27.0 μg/mL); calcium channel blocker (rbt, isolated smooth muscle, PD’2 = 5.48 μg/mL); negative inotropic activity (isolated guinea pig atria muscles, 36 μmol/L, 50% negative inotropic activity); bradycardia activity (isolated guinea pig heart, 45 μmol/kg, 43.7% bradycardia together with decreasing of blood pressure of 24 mmHg). Ref: J. Su, et al, JNP, 1991, 54, 380

4 3

H

O

O

O

11 Clavirolide D Type: Dolabellane diterpenoids. C20H28O3 Syrup, [α]D26.5 = −118.5° (c = 0.08, MeOH). Source: Stolonifer Clavularia viridis (Xisha Is., South China Sea, China). Pharm: Cytotoxic (EAC, ED50 = 11.7 μg/mL); calcium channel blocker (rbt, isolated smooth muscle, PD’2 = 4.79 μg/mL). Ref: J. Su, et al, JNP, 1991, 54, 380 5 4

3

O

H

O

O

12 Clavirolide E 6-Oxo-4(16),12(18)-dolabelladien-19,10-olide Type: Dolabellane diterpenoids. C20H28O3 Cryst., mp 200–201 °C, [α]D20 = −40° (c = 0.01, MeOH). Source: Stolonifer Clavularia viridis. Pharm: Calcium channel blocker. Ref: J. Su, et al, JNP, 1991, 54, 380 O O H 10

8

O 5

4

3.19 Dolabellane Diterpenoids

5

13 Clavulactne Type: Dolabellane diterpenoids. C20H28O3 Cryst. (Me2CO/petrol), mp 195–197 °C, [α]D20 = −238.5° (c = 0.035, MeOH). Source: Stolonifer Clavularia viridis (Xisha Is., South China Sea, China). Pharm: Cytotoxic (EAC, ED50 = 8.0 μg/mL). Ref: J. Li, et al, Acta Chim. Sinica, 1987, 45, 558│J. Su, et al, JNP, 1991, 54, 380│Z. -Y. Yang, et al, Angew. Chem., Int. Ed., 2012, 51, 6484

4

3

O H

O

14 10,18-Diacetoxydolabella-2,7E-dien-6-one Type: Dolabellane diterpenoids. C24H36O5 [α]D = −23.6° (c = 0.97, CHCl3); [α]D25 = −36° (c = 0.22, CHCl3). Source: Sponges Dysidea sp. (Palau, Oceania) and Sigmosceptrella quadrilobata (Comoros). Pharm: Cytotoxic (GM7373, IC50 = 15.8 μg/mL, J774, IC50 = 17.2 μg/mL, WEHI-164, IC50 = 14.7 μg/mL, P388, IC50 = 7.7 μg/mL). Ref: Q. Lu, et al, JNP, 1998, 61, 1096│ V. Costantino, et al, EurJOC, 1999, 227 O H

O

O O O

15 2,13-Diacetoxy-3,7,18-dolabellatrien-9-one Type: Dolabellane diterpenoids. C24H34O5 Source: Sea whip Convexella magelhaenica (deep water, South Atlantic site). Pharm: Cytotoxic (mild). Ref: M. T. R. de Almeida, et al, JNP, 2010, 73, 1714 O O

O O H

H

6

3 Diterpenoids

16 19,20-Diacetoxy-7,8-epoxy-3,12,13-dolabellatrien Type: Dolabellane diterpenoids. C24H34O5 Glass, [α]D24 = +0° (c = 1). Source: Gorgonian Eunicea tourneforti. Pharm: Inhibits RS321 (IC12 > 3000 μg/mL). Ref: M. Govindan, et al, JNP, 1995, 58, 1174 O

O

H

O

O

O

17 (1R*)-Dolabella-4(16),7,11(12)-triene-3,13-dione Type: Dolabellane diterpenoids. C20H28O2 Oil, [α]D25 = −264.5° (c = 0.11, CHCl3). Source: Stolonifer Clavularia inflata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 > 50 μg/mL; HT29, ED50 > 50 μg/mL; P388, ED50 = 3.89 μg/mL). Ref: C. Y. Duh, et al, JNP, 2001, 64, 1028

O

O

18 Dolabella-4(16),7-diene-10,11-epoxy-3,13-dione Type: Dolabellane diterpenoids. C20H28O3 Source: Stolonifer Clavularia inflata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 7.74 μg/mL; HT29, ED50 = 6.39 μg/mL; P388, ED50 = 3.83 μg/mL). Ref: C. Y. Duh, et al, JNP, 2001, 64, 1028 O O

O

19 Dolabella-4(16),10-diene-7,8-epoxy-3,13-dione Type: Dolabellane diterpenoids. C20H28O3 Source: Stolonifer Clavularia inflata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 8.56 μg/mL; HT29, ED50 = 7.84 μg/mL; P388, ED50 = 2.48 μg/mL). Ref: C. Y. Duh, et al, JNP, 2001, 64, 1028

3.19 Dolabellane Diterpenoids

7

O

O H O

20 Dolabellanone 9 7-Hydroperoxy-3,8,12-dolabellatrien-14-one Type: Dolabellane diterpenoids. C20H30O3 Oil, [α]D25 = +43.1° (c = 1, CHCl3). Source: Gorgonian Eunicea sp. (Old Providence I., Colombia). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 9.4 μmol/L). Ref: X. Wei, et al, JNP, 2010, 73, 925 O

H HO

O

21 (1R*,12R*)-Dolabella-4(16),7,10-triene-3,13-dione Type: Dolabellane diterpenoids. C20H28O2 Oil, [α]D25 = −92.3° (c = 0.1, CHCl3). Source: Stolonifer Clavularia inflata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 > 50 μg/mL; HT29, ED50 = 27.3 μg/mL; P388, ED50 = 2.60 μg/mL). Ref: C. Y. Duh, et al, JNP, 2001, 64, 1028

O

O

22 3,7,18-Dolabellatrien-9-one Type: Dolabellane diterpenoids. C20H30O Oil, [α]D25 = −23.4° (c = 7.5, CHCl3). Source: Sea whip Convexella magelhaenica (deep water, South Atlantic site). Pharm: Cytotoxic (mild). Ref: M. T. R. de Almeida, et al, JNP, 2010, 73, 1714

H

H

O

8

3 Diterpenoids

23 3,4-Epoxy-7,18-dolabelladiene Type: Dolabellane diterpenoids. C20H32O Source: Brown alga Dictyota dichotoma. Pharm: Antibacterial (gram-positive and gram-negative bacteria); cytotoxic (KB); antiviral (influenza and adenovirus viruses). Ref: M. Piattelli, et al, JNP, 1995, 58, 697 O

H

24 7,8-Epoxy-3,18-dolabelladiene Type: Dolabellane diterpenoids. C20H32O [α]D25 = +27.4° (c = 0.46, CHCl3). Source: Brown alga Dictyota dichotoma (Cádiz, Spain). Pharm: Cytotoxic (P388, ED50 = 5 μg/mL, A549, ED50 = 5 μg/mL, HT29, ED50 = 5 μg/mL, MEL28, ED50 = 5 μg/mL). Ref: R. Durán, et al, Tetrahedron, 1997, 53, 8675

H

O

25 7,8-Epoxy-3,12-dolabelladien-14-one Type: Dolabellane diterpenoids. C20H32O2 Cryst., mp 134–136 °C. Source: Gorgonian Eunicea tourneforti. Pharm: Inhibits RS321 (IC12 > 2600 μg/mL). Ref: M. Govindan, et al, JNP, 1995, 58, 1174 H O O

26 3,4-Epoxy-14-hydroxy-7,18-dolabelladiene Type: Dolabellane diterpenoids. C20H32O2 Source: Brown alga Dictyota dichotoma. Pharm: Antibacterial (gram-positive and gram-negative bacteria); cytotoxic (KB); antiviral (influenza and adenovirus viruses). Ref: M. Piattelli, et al, JNP, 1995, 58, 697

3.19 Dolabellane Diterpenoids

9

OH O

H

27 3,4-Epoxy-14-oxo-7,18-dolabelladiene Type: Dolabellane diterpenoids. C20H30O2 Source: Brown alga Dictyota dichotoma. Pharm: Antibacterial (gram-positive and gram-negative bacteria); cytotoxic (KB); antiviral (influenza and adenovirus viruses). Ref: M. Piattelli, et al, JNP, 1995, 58, 697 O O

H

28 7-Hydroperoxydolabella-4(16),8(17),11(12)-triene-3,13-dione Type: Dolabellane diterpenoids. C20H28O4 Source: Stolonifer Clavularia inflata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 0.57 μg/mL; HT29, ED50 = 0.31 μg/mL; P388, ED50 = 0.052 μg/mL). Ref: C. Y. Duh, et al, JNP, 2001, 64, 1028

HO

O

O

O

29 (1R*,3R*)-3-Hydroxydolabella-4(16),7,11(12)-triene-3,13-dione Type: Dolabellane diterpenoids. C20H30O2 Source: Stolonifer Clavularia inflata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 8.10 μg/mL; HT29, ED50 = 9.19 μg/mL; P388, ED50 = 3.82 μg/mL). Ref: C. Y. Duh, et al, JNP, 2001, 64, 1028

O

OH

10

3 Diterpenoids

30 Palominol (1α,3E,7E,11α)-3,7,12-Dolabellatrien-18-ol Type: Dolabellane diterpenoids. C20H32O Cryst., mp 52–53 °C, [α]D27 = −33.3° (c = 1, CHCl3). Source: Gorgonians Eunicea calyculata and Eunicea laciniata (Caribbean Sea). Pharm: Cytotoxic (HCT116, IC50 = 10 μg/ mL). Ref: J. Cáceres, et al, Tetrahedron, 1990, 46, 341│ J. Shin, et al, JOC, 1991, 56, 3392│ A. D. Rodriguez, et al, JNP, 1993, 56, 1843

H

OH

31 Stolonidiol Type: Dolabellane diterpenoids. C20H32O4 Viscous oil, [α]D = −31° (c = 1.4, CHCl3). Source: Stolonifer Clavularia sp. Pharm: Neurotrophic factor (ChAT inducer, basal forebrain cells: 0 μg/mL, ChAT activity = 100%, 0.01 μg/mL, ChAT activity = 130.2%, 0.1 μg/mL, ChAT activity = 177.5%, 1 μg/mL, ChAT activity = 138.6%, 10 μg/mL, ChAT activity = 38.2%; SN49cells: 0 μg/mL, ChAT activity = 100%, 0.01 μg/mL, ChAT activity = 146.2%, 0.1 μg/mL, ChAT activity = 141.8%, 1 μg/mL, ChAT activity = 144.7%, 10 μg/mL, ChAT activity = 92.7%); cytotoxic; ichthyotoxic. Ref: K. Mori, et al, Tet. Lett., 1987, 28, 5673│ T. Yabe, et al, JNP, 2000, 63, 433│ H. Miyaoka, et al, Tet. Lett., 2001, 42, 9233

O

H

H

O

OH

OH

32 Stolonidiol-17-acetate Type: Dolabellane diterpenoids. C22H34O5 Viscous oil, [α]D = −26.8° (c = 0.38, CHCl3). Source: Stolonifer Clavularia sp. Pharm: Cytotoxic; ichthyotoxin. Ref: K. Mori, et al, Tet. Lett., 1987, 28, 5673│ T. Yabe, et al, JNP, 2000, 63, 433 17

O

O

O O

OH

3.21 Cyathane Diterpenoids

11

3.20 Dolastane Diterpenoids 33 Dolatriol Type: Dolastane diterpenoids. C20H32O3 Crystal (Me2CO/heptane), mp 235–236 °C. Source: Sea hare Dolabella auricularia. Pharm: Cytotoxic (P388). Ref: G. R. Pettit, et al, JACS, 1976, 98, 4677 OH

HO H

OH

34 Dolatriol-6-acetate Type: Dolastane diterpenoids. C22H34O4 Source: Sea hare Dolabella auricularia. Pharm: Cytotoxic (P388). Ref: G. R. Pettit, et al, JACS, 1976, 98, 4677 OH OH O

O

3.21 Cyathane Diterpenoids 35 Cyanthiwigin A 2,12-Cyathadien-1-one Type: Cyathane diterpenoids. C20H30O Cryst., mp 84–85 °C, [α]D = +7° (c = 0.5, CH2Cl2); colorless cryst., [α]D = +46° (c = 0.1, CH2Cl2). Source: Sponges Epipolasis reiswigi (off Jamaica) and Myrmekioderma styx (deep water, Jamaica). Pharm: Cytotoxic (tumor tissues obtained from patients undergoing surgical resections, IC50 = 6.8 μmol/L); antiviral (HBV, EC50 > 100 μg/mL); anti-HIV-1 (HIV-1, EC50 > 100 μg/mL); antituberculosis (Mycobacterium tuberculosis, 6.25 μg/mL, InRt = 25%). Ref: D. Green, et al, NPL, 1992, 1, 193│ J. Peng, et al, Tetrahedron, 2002, 58, 7809 O 1

9

H

H

13 12

12

3 Diterpenoids

36 Cyanthiwigin B 2,12-Cyathadiene-1,8-dione Type: Cyathane diterpenoids. C20H28O2 Amorphous powder, [α]D = −128° (c = 0.5, CH2Cl2); colorless cryst., [α]D = −125° (c = 0.1, MeOH). Source: Sponges Epipolasis reiswigi (off Jamaica) and Myrmekioderma styx (deep water, Jamaica). Pharm: Antiviral (HBV, EC50 > 100 μg/mL); anti-HIV-1 (HIV-1, EC50 = 42.1 μg/mL); antituberculosis (Mycobacterium tuberculosis, 6.25 μg/mL, InRt = 9%). Ref: D. Green, et al, Nat. Prod. Lett., 1992, 1, 193│ J. Peng, et al, Tetrahedron, 2002, 58, 7809 O

O

H H

37 Cyanthiwigin C Type: Cyathane diterpenoids. C20H32O Amorphous powder, [α]D = +25° (c = 0.02, EtOAc), [α]D22 = +38.5° (c = 0.05, CH2Cl2); colorless cryst., [α]D = +37.5° (c = 0.12, MeOH). Source: Sponges Epipolasis reiswigi (off Jamaica) and Myrmekioderma styx (deep water, Jamaica). Pharm: Cytotoxic (tumor tissues obtained from patients undergoing surgical resections, IC50 = 7.8 μmol/L); antiviral (HBV, EC50 = 43 μg/mL); anti-HIV-1 (HIV-1, EC50 > 100 μg/mL); antituberculosis (Mycobacterium tuberculosis, 6.25 μg/mL, InRt = 50%). Ref: D. Green, et al, Nat. Prod. Lett., 1992, 1, 193│ J. Peng, et al, Tetrahedron, 2002, 58, 7809 OH H H H

38 Cyanthiwigin D Type: Cyathane diterpenoids. C20H32O2 Amorphous powder, [α]D = +17° (c = 0.04, EtOAc); colorless cryst., [α]D = +25° (c = 0.12, MeOH). Source: Sponges Epipolasis reiswigi (off Jamaica) and Myrmekioderma styx (deep water, Jamaica). Pharm: Cytotoxic (tumor tissues obtained from patients undergoing surgical resections, IC50 = 5.0 μmol/L); anti-HIV-1 (HIV-1, EC50 > 100 μg/mL); antituberculosis (Mycobacterium tuberculosis, 6.25 μg/mL, InRt = 30%). Ref: D. Green, et al, NPL, 1992, 1, 193│ J. Peng, et al, Tetrahedron, 2002, 58, 7809

3.21 Cyathane Diterpenoids

13

OH

OH

H

H H H

39 Cyanthiwigin E Type: Cyathane diterpenoids. C20H30O2 White powder, [α]D = +90° (c = 0.10, MeOH). Source: Sponge Myrmekioderma styx (deep water, Jamaica). Pharm: Cytotoxic (tumor tissues obtained from patients undergoing surgical resections, IC50 = 9.1 μmol/L). Ref: J. Peng, et al, Tetrahedron, 2002, 58, 7809 OH

O 1

9

H

H

13 12

40 Cyanthiwigin F Type: Cyathane diterpenoids. C20H30O Colorless cryst., [α]D = −128° (c = 0.03, MeOH). Source: Sponge Myrmekioderma styx (deep water, Jamaica). Pharm: Cytotoxic (tumor tissues obtained from patients undergoing surgical resections, IC50 = 3.1 μmol/L). Ref: J. Peng, et al, Tetrahedron, 2002, 58, 7809 O 1

9

H

H

13 12

41 Cyanthiwigin J Type: Cyathane diterpenoids. C20H32O3 White powder, [α]D = +50° (c = 0.11, MeOH). Source: Sponge Myrmekioderma styx (deep water, Jamaica). Pharm: Cytotoxic (tumor tissues obtained from patients undergoing surgical resections, IC50 = 18.1 μmol/L). Ref: J. Peng, et al, Tetrahedron, 2002, 58, 7809

14

3 Diterpenoids

OH

HO 1

9

H

H

13 12

O

42 Cyanthiwigin U 12-Hydroxy-2,13-cyathadien-1-one Type: Cyathane diterpenoids. C20H30O2 Colorless cryst., [α]D = +131° (c = 0.10, MeOH). Source: Sponge Myrmekioderma styx (deep water, Jamaica). Pharm: Anti-HIV-1 (HIV-1, EC50 > 100 μg/mL). Ref: J. Peng, et al, Tetrahedron, 2002, 58, 7809 O 1

9

H

H

13 12

OH

43 Cyanthiwigin Z Type: Cyathane diterpenoids. C20H30O2 Colorless gum, [α]D = −160° (c = 0.03, MeOH). Source: Sponge Myrmekioderma styx (deep water, Jamaica). Pharm: AntiHIV-1 (HIV-1, EC50 = 5.6 μg/mL). Ref: J. Peng, et al, Tetrahedron, 2002, 58, 7809 HO 1

9

H

H

O 13 12

3.22 Modified Verrucosane Diterpenoids 44 Gukulenin A Type: Modified verrucosane diterpenoids. C42H54O10 Amorph. solid, [α]D25 = −64.7° (c = 0.15, MeOH), [α]D25 = −19.1° (c = 0.35, MeCN). Source: Sponge Phorbas gukulensis (Gageo I., R. O. Korea). Pharm: Cytotoxic (K562 and A549, significant). Ref: S. Y. Park, et al, JNP, 2010, 73, 734│ J. -E. Jeon, et al, JNP, 2013, 76, 1679

3.22 Modified Verrucosane Diterpenoids

HO OH H

15

O

OH

O

H 8'

H

O O

O

OH O

45 Gukulenin C Type: Modified verrucosane diterpenoids. C43H59NO10 Yellow amorphous solid,; [α]D25 = −4.8° (c = 0.35, MeCN). Source: Sponge Phorbas gukulensis (Gageo I., R. O. Korea). Pharm: Cytotoxic (K562 and A549, significant). Ref: J. -E. Jeon, et al, JNP, 2013, 76, 1679 HO OH H

O

O

OH

H H N

H

O H O

OH

O H

OH

46 Gukulenin D Type: Modified verrucosane diterpenoids. C42H57NO10 Yellow amorphous solid,; [α]D25 = −19.2° (c = 0.20, MeCN). Source: Sponge Phorbas gukulensis (Gageo I., R. O. Korea). Pharm: Cytotoxic (K562 and A549, significant). Ref: J. -E. Jeon, et al, JNP, 2013, 76, 1679 HO OH H

O

O

OH

H H N

H

O H O

OH

OH H

OH

47 Gukulenin E Type: Modified verrucosane diterpenoids. C42H57NO11S Yellow amorphous solid,; [α]D25 = −13.9° (c = 0.55, MeCN). Source: Sponge Phorbas gukulensis (Gageo I., R. O. Korea). Pharm: Cytotoxic (K562 and A549, significant). Ref: J. -E. Jeon, et al, JNP, 2013, 76, 1679

16

3 Diterpenoids

OH H

O

OH

H

H O O

HN

OH

S

O OH

48 Gukulenin F Type: Modified verrucosane diterpenoids. C42H54O10 Yellow amorphous solid,; [α]D25 = −21.2° (c = 0.40, MeCN). Source: Sponge Phorbas gukulensis (Gageo I., R. O. Korea). Pharm: Cytotoxic (K562 and A549, significant). Ref: J. -E. Jeon, et al, JNP, 2013, 76, 1679 HO

OH

O

OH H H

OH O

OH

O O

O H

3.23 Spatane Diterpenoids 49 13,16-Spatadiene-5,15,18,19-tetrol Type: Spatane diterpenoids. C20H32O4 Oil, [α]D = −10.7° (c = 1.8, CHCl3). Source: Brown alga Stoechospermum marginatum. Pharm: Algicide; ichthyotoxic. Ref: W. H. Gerwick, et al, JOC, 1981, 46, 2233 OH

H

OH H

H OH

OH

50 (+)-Spatol 15,16:17,18-Diepoxy-13-spaten-5-ol Type: Spatane diterpenoids. C20H30O3 Nat: mp 100–101 °C, [α]D23 = +45.5° (CHCl3); Syn: mp 100–102 °C, [α]D23 = +45.6° (CHCl3). Source: Brown algae Spatoglossum schmittii and Spatoglossum howleii. Pharm: Cell division inhibitor; cytotoxic (potent). Ref: W. H. Gerwick, et al, JACS, 1980, 102,

3.24 Verticillane Diterpenoids

17

7991│ W. H. Gerwick, et al, JOC, 1983, 48, 3325│ M. Tanaka, et al, Tetrahedron, 1994, 50, 12843 OH

H

H

O

H

51 Dilkamural Type: Seco- and abeo-spatane diterpenoids. C24H34O6 Oil, [α]D22 = +32° (c = 0.13, CHCl3). Source: Brown alga Dilophus okamurai (Japan waters). Pharm: Antibacterial (Bacillus subtilis, inhibitive zone = 12 mm, 10 μg/disk); inhibits plant pathogenic mold (Colletotrichum lagenarium, weakly). Ref: M. Ninomiya, et al, JOC, 1999, 64, 5436 H O

H

2

O

O O

O

H

O

52 Dilophus ether Type: Seco- and abeo-spatane diterpenoids. C22H32O4 [α]D = –69° (c = 0.86, CHCl3). Source: Brown alga Dilophus okamurai. Pharm: Antifeedant. Ref: K. Kurata, et al, Tet. Lett., 1989, 30, 1567 O O

O

O H H

3.24 Verticillane Diterpenoids 53 Cespitularin A Type: Verticillane diterpenoids. C20H28O2 Amorph. solid, mp 71–72 °C, [α]D25 = −140.1° (c = 0.12, CHCl3). Source: Soft coral Cespitularia hypotentaculata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 8.42 μg/mL; HT29, ED50 = 9.76 μg/mL; P388,

18

3 Diterpenoids

ED50 = 3.66 μg/mL, for significant activity ED50 ≤ 4.0 μg/mL is required). Ref: C. -Y. Duh, et al, JNP 2002, 65, 1429 O 6

OH

H

54 Cespitularin B Type: Verticillane diterpenoids. C20H28O Amorph. solid, mp 62–63 °C, [α]D25 = −20.6° (c = 0.08, CHCl3). Source: Soft coral Cespitularia hypotentaculata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 7.96 μg/mL; HT29, ED50 = 9.25 μg/mL; P388, ED50 = 3.23 μg/mL). Ref: C. -Y. Duh, et al, JNP 2002, 65, 1429 O 6

H

55 Cespitularin C Type: Verticillane diterpenoids. C20H32O Amorph. solid, mp 66–68 °C, [α]D25 = −62.3° (c = 0.1, CHCl3). Source: Soft coral Cespitularia hypotentaculata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 0.12 μg/mL; HT29, ED50 = 8.86 μg/mL; P388, ED50 = 0.01 μg/mL). Ref: C. -Y. Duh, et al, JNP 2002, 65, 1429 HO

H

56 Cespitularin D Type: Verticillane diterpenoids. C20H28O4 Oil, [α]D25 = −169.6° (c = 0.23, CHCl3). Source: Soft coral Cespitularia hypotentaculata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 > 50 μg/mL; HT29, ED50 > 50 μg/mL; P388, ED50 = 3.86 μg/mL). Ref: C. -Y. Duh, et al, JNP 2002, 65, 1429

3.24 Verticillane Diterpenoids

OH

O

O

19

10

OH

6

H

57 Cespitularin E Type: Verticillane diterpenoids. C19H28O2 Oil, [α]D25 = +122.3° (c = 0.22, CHCl3). Source: Soft coral Cespitularia hypotentaculata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 0.034 μg/mL; HT29, ED50 = 17.1 μg/mL; P388, ED50 = 4.66 μg/mL). Ref: C. -Y. Duh, et al, JNP 2002, 65, 1429 O OH

H

58 Cespitularin F Type: Verticillane diterpenoids. C20H28O3 Oil, [α]D25 = +39.8° (c = 0.21, CHCl3). Source: Soft coral Cespitularia hypotentaculata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 16.11 μg/mL; HT29, ED50 > 50 μg/mL; P388, ED50 > 50 μg/mL). Ref: C. -Y. Duh, et al, JNP 2002, 65, 1429; 2006, 69, 1188 OH H HO

O

20

6

H

59 Cespitularin H Type: Verticillane diterpenoids. C20H28O3 Amorph. solid, mp 120–121 °C, [α]D25 = −93.6° (c = 0.19, CHCl3). Source: Soft coral Cespitularia hypotentaculata (Taiwan waters). Pharm: Cytotoxic (A549, ED50 = 9.32 μg/mL; HT29, ED50 = 23.69 μg/mL; P388, ED50 > 50 μg/mL). Ref: C. -Y. Duh, et al, JNP 2002, 65, 1429

20

3 Diterpenoids

H O

HO

O

H

60 Cespitulin G Type: Verticillane diterpenoids. C22H32O5 Source: Soft coral Cespitularia taeniata (Green I., Taiwan). Pharm: Elastase release inhibitor (moderate); superoxide production inhibitor (stimulated hmn neutrophils). Ref: J. -Y. Chang, et al,Chem. Biodiversity, 2012, 9, 654 O

OH O

O

O

H

3.25 Taxane Diterpenoids 61 Taxol Paclitaxel Type: Taxane diterpenoids. C47H51NO14 Needles (MeOH aq), mp 213–216 °C, [α]D20 = −49° (MeOH). Source: Fungus Taxomyces andreanae (traces), terrestrial plants (Taxus spp.). Pharm: Cytotoxic (MTT assay, MDA-MB-231, GI50 = 7.0 nmol/L; U2OS, GI50 = 12 nmol/L; NMuMG, GI50 = 5.9 nmol/L; NIH3T3, GI50 = 6.4 nmol/L); antineoplastic (especially melanoma and ovarian tumours, use limited by low solubility); antifungal (oomycete fungi); LD50 (mus, ipr) = 128 mg/kg; LD50 (mus, ivn) = 12 mg/kg. Ref: K. Taori, et al, JACS, 2008, 130, 1806│ CRC Press, DNP on DVD, 2012, version 20.2 O O O

OH

O

O N H

O OH

OH O O O

H

O

O

3.26 Amphilectane Diterpenoids

21

3.26 Amphilectane Diterpenoids 62 (1R*)-7-Formamido-11(20),14-amphilectadiene Type: Amphilectane diterpenoids. C21H33NO Clear oil, [α]D25 = +80.4° (c = 0.50, CHCl3). Source: Sponge Cymbastela hooperi (Kelso Reef, Queensland, Australia). Pharm: Antiplasmodial (Plasmodium falciparum FCR3F86, IC50 = 63.0 μg/mL, control Atovaquone, IC50 = (0.4 ± 0.3)ng/mL). Ref: A. D. Wright, et al, JNP, 2009, 72, 492 H 1R

H

H

H H

O N H

H

63 (1S*)-7-Formamido-11(20),15-amphilectadiene Type: Amphilectane diterpenoids. C21H33NO Clear oil, [α]D25 = +15.5° (c = 0.22, CHCl3). Source: Sponge Cymbastela hooperi (Kelso Reef, Queensland, Australia). Pharm: Antiplasmodial (Plasmodium falciparum FCR3F86, IC50 > 90 μg/mL, control Atovaquone, IC50 = (0.4 ± 0.3)ng/mL). Ref: A. D. Wright, et al, JNP, 2009, 72, 492 H 1S

H

H

H H

O N H

H

64 Helioporin A Type: Amphilectane diterpenoids. C21H28O3 Oil, [α]D24 = +65° (c = 4.4, CHCl3). Source: Blue coral Heliopora coerulea (Okinawa). Pharm: Antiviral (HSV-1, IC50 = 4.0 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ S. A. Look, et al, Tetrahedron, 1987, 43, 3363│ J. Tanaka, et al, Tetrahedron, 1993, 49, 811

22

3 Diterpenoids

15

O

14

H H

O O

65 Helioporin B Type: Amphilectane diterpenoids. C21H30O3 Oil, [α]D24 = +18.8° (c = 2.55, CHCl3). Source: Blue coral Heliopora coerulea (Okinawa). Pharm: Antiviral (HSV-1, IC50 = 1.6 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ S. A. Look, et al, Tetrahedron, 1987, 43, 3363│ J. Tanaka, et al, Tetrahedron, 1993, 49, 811 O O

O

14

15

66 Helioporin C Type: Amphilectane diterpenoids. C21H28O3 Oil, [α]D22 = +8.3° (c = 0.58, CHCl3). Source: Blue coral Heliopora coerulea (Okinawa). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ S. A. Look, et al, Tetrahedron, 1987, 43, 3363│ J. Tanaka, et al, Tetrahedron, 1993, 49, 811 O O

O

15

67 Helioporin D Type: Amphilectane diterpenoids. C21H30O2 Oil, [α]D23 = +6.3° (c = 0.36, CHCl3). Source: Blue coral Heliopora coerulea (Okinawa). Pharm: Cytotoxic (P388, IC50 = 2 μg/mL); anti-inflammatory. Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ S. A. Look, et al, Tetrahedron, 1987, 43, 3363│ J. Tanaka, et al, Tetrahedron, 1993, 49, 811│ T. Geller, et al, Tet. Lett., 1998, 39, 1537; 1541

3.26 Amphilectane Diterpenoids

23

O O

68 Helioporin E Type: Amphilectane diterpenoids. C21H28O2 Oil, [α]D23 = +111° (c = 0.55, CHCl3). Source: Blue coral Heliopora coerulea (Okinawa). Pharm: Cytotoxic (P388, IC50 = 7 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ S. A. Look, et al, Tetrahedron, 1987, 43, 3363│ J. Tanaka, et al, Tetrahedron, 1993, 49, 811│ S. E. Lazerwith, et al, Org. Lett., 2000, 2, 2389 15 14

H

H O O

69 Helioporin F Type: Amphilectane diterpenoids. C21H28O2 Oil, [α]D23 = −17° (c = 0.23, CHCl3). Source: Blue coral Heliopora coerulea (Okinawa). Pharm: Cytotoxic (P388, IC50 = 5 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ S. A. Look, et al, Tetrahedron, 1987, 43, 3363│ J. Tanaka, et al, Tetrahedron, 1993, 49, 811 O O

H 12 13

70 Helioporin G Type: Amphilectane diterpenoids. C21H28O2 Oil, [α]D23 = −50° (c = 0.69, CHCl3). Source: Blue coral Heliopora coerulea (Okinawa). Pharm: Cytotoxic (P388, IC50 = 5 μg/mL).

24

3 Diterpenoids

Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ S. A. Look, et al, Tetrahedron, 1987, 43, 3363│ J. Tanaka, et al, Tetrahedron, 1993, 49, 811 O O

H 12 13

71 Homopseudopteroxazole Type: Amphilectane diterpenoids. C26H37NO Yellowish oil, [α]D25 = +103.2° (c = 0.9, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL). Ref: I. I. Rodríguez, et al, JNP, 2003, 66, 855

O N H

72 7-Isocyano-10,14-amphilectadiene Type: Amphilectane diterpenoids. C21H31N Oil, [α]D = −3.7° (c = 0.38, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 302 ng/mL, SI > 66.2, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 133 ng/mL, SI > 150, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 > 20000 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 H H H

H H

NC

3.26 Amphilectane Diterpenoids

25

73 7-Isocyanoamphilecta-11(20),15-diene Type: Amphilectane diterpenoids. C21H31N Cryst. (hexane), mp 148–149 °C, [α]D = +14° (c = 0.84, CHCl3). Source: Sponges Cymbastela hooperi (Great Barrier Reef) and Adocia spp. Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 520 ng/mL, SI > 38.5, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 242 ng/mL, SI > 82.6, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 > 20000 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: R. Kazlauskas, et al, Tet. Lett., 1980, 21, 315│ G. M. König, et al, JOC, 1996, 61, 3259 H H H

H H

NC

74 7-Isocyano-11,14-epi-amphilectadiene Type: Amphilectane diterpenoids. C21H31N Cryst. (hexane), mp 106.6–108.3 °C, [α]D25 = −55.9° (c = 0.9, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 58.5 ng/mL, SI = 260, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 25.6 ng/mL, SI = 590, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 15200 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 H H H H

NC

75 7-Isocyano-11(20),14-epi-amphilectadiene Type: Amphilectane diterpenoids. C21H31N Cryst., mp 113–115 °C, mp 114.7–115.8 °C, [α]D25 = +115.8° (c = 1.23, CHCl3), [α]D20 = +116.8° (c = 1.0, CHCl3). Source: Sponges Adocia spp. and Cymbastela hooperi. Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 14.1 ng/mL, SI = 230, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 9.3 ng/mL, SI = 340, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 3200 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: R. Kazlauskas, et al, Tet. Lett., 1980, 21, 315│ A. Linden, et al, Acta Crystallogr., Scot. C: Cryst. Struct. Commun., 1996, 52, 2601│ G. K. König, et al, JOC, 1996, 61, 3259

26

3 Diterpenoids

H H

H H

NC

76 7-Isocyano-15-isothiocyanato-11(20)-amphilectene Type: Amphilectane diterpenoids. C22H32N2S Cryst. (hexane), mp 102.8–103.7 °C, [α]D25 = +1.5° (c = 0.55, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 470 ng/mL, SI > 42.6, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 109 ng/mL, SI > 183, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 > 20000 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 NCS

H H

H H

NC

77 7-Isocyano-1(14),15-neoamphilectadiene Type: Amphilectane diterpenoids. C21H31N Oil, [α]D25 = +67.0° (c = 0.79, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 90.0 ng/mL, SI = 210, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 29.7 ng/mL, SI = 640, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 19100 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259

H H H

NC

3.26 Amphilectane Diterpenoids

27

78 7-Isothiocyanato-11(20),14-epi-amphilectadien-12-ol Type: Amphilectane diterpenoids. C21H31NOS Oil, [α]D25 = +78.4° (c = 0.56, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 797 ng/mL, SI = 6.6, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 423 ng/mL, SI = 12.5, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 5300 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259

H OH

H H

NCS

79 Pseudopterosin A (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-β-D-xylopyranoside Type: Amphilectane diterpenoids. C25H36O6 Amorph. solid, [α]D20 = −85° (c = 0.69, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (high); analgesic; elastase stimulant (used in cosmetic antiwrinkle creams); antibacterial (25 μg/mL for 6 mm disc, gram-positive bacteria Streptococcus pyogenes, IZD = 15 mm, MIC = 0.8 μg/mL; Staphylococcus aureus, IZD = 11 mm, MIC = 2.1 μg/mL; Enterococcus faecalis, IZD = 9 mm, MIC = 3.4 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ A. Ata, et al, Helv. Chim. Acta 2004, 87, 1090

1

H

BDXYLOP

OO OH OH

3

10

9

7

OH OH

80 Pseudopterosin B (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-(2-acetyl-β-D-xylopyranoside) Type: Amphilectane diterpenoids. C27H38O7 Oil, [α]D20 = −55.2° (c = 2.1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory; analgesic; antibacterial (25 μg/mL for 6 mm disc, gram-positive bacteria Streptococcus pyogenes, IZD = 13 mm, MIC = 1.0 μg/mL; Staphylococcus aureus, IZD = 10 mm, MIC = 2.3 μg/mL;

28

3 Diterpenoids

Enterococcus faecalis, IZD = 9 mm, MIC = 3.2 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ A. Ata, et al, Helv. Chim. Acta 2004, 87, 1090

1

H

BDXYLOP

OO OH OH

3

10

O

9

7

OH

O

81 Pseudopterosin C (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-(3-acetyl-β-D-xylopyranoside) Type: Amphilectane diterpenoids. C27H38O7 Cryst. (EtOAc/EtOH), mp 113.5–115 °C, [α]D20 = −77° (c = 1.09, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory; analgesic; used in skin care; antibacterial (25 μg/mL for 6 mm disc, gram-positive bacteria Streptococcus pyogenes, IZD = 16 mm, MIC = 1.0 μg/mL; Staphylococcus aureus, IZD = 11 mm, MIC = 2.0 μg/mL; Enterococcus faecalis, IZD = 8 mm, MIC = 3.7 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ A. Ata, et al, Helv. Chim. Acta 2004, 87, 1090

1

3

H

O

OO O

OH

10

9

7

OH OH

BDXYLOP

82 Pseudopterosin D (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-(4-acetyl-β-D-xylopyranoside) Type: Amphilectane diterpenoids. C27H38O7 Oil, [α]D20 = −107.3° (c = 0.55, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antiinflammatory; analgesic; antibacterial (25 μg/mL for 6 mm disc, gram-positive bacteria Streptococcus pyogenes, IZD = 17 mm, MIC = 1.0 μg/mL; Staphylococcus aureus, IZD = 9 mm, MIC = 2.3 μg/mL; Enterococcus faecalis, IZD = 9 mm, MIC = 3.8 μg/mL). Ref: S. A. Look, et al, JOC, 1986, 51, 5140│ A. Ata, et al, Helv. Chim. Acta 2004, 87, 1090

3.26 Amphilectane Diterpenoids

1

29

3

H OO

O

OH O

10

9

7

OH BDXYLOP

OH

83 Pseudopterosin E (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 10-O-α-L-fucopyranoside Type: Amphilectane diterpenoids. C26H38O6 Amorph., [α]D = −255° (c = 0.4, MeOH). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (with very low acute toxicity in mice, LD50 > 300mg/kg, and appearsto act by a novel mechanism of pharmacological action); lipoxygenase inhibitor; degranulation inhibitor; leucotriene formation inhibitor; antibacterial (25 μg/mL for 6 mm disc, gram-positive bacteria Streptococcus pyogenes, IZD = 12 mm, MIC = 1.0 μg/mL; Staphylococcus aureus, IZD = 8 mm, MIC = 2.3 μg/mL; Enterococcus faecalis, IZD = 8 mm, MIC = 3.6 μg/mL). Ref: V. Roussis, et al, JOC, 1990, 55, 4916│ A. Ata, et al, Helv. Chim. Acta 2004, 87, 1090

1

3

H OO HO

7

10

9

OH

HO OH

84 Pseudopterosin F (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 10-O-α-D-arabinopyranoside Type: Amphilectane diterpenoids. C25H36O6 Needles, mp 200 °C (dec), [α]D = −243.2° (c = 0.5, MeOH). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antiinflammatory. Ref: V. Roussis, et al, JOC, 1990, 55, 4916

30

3 Diterpenoids

1

3

O

OH HO

H O

OH

10

9

7

OH

ADARABP

85 Pseudopterosin G (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-α-L-fucopyranoside Type: Amphilectane diterpenoids. C26H38O6 Oil, [α]D = −56.8° (c = 2.3, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory. Ref: V. Roussis, et al, JOC, 1990, 55, 4916│ S. E. Lazerwith, et al, Org. Lett., 2000, 2, 2389

1

3

H HO

7

10

9

OO

HO HO OH

86 Pseudopterosin H (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-(2-acetyl-α-L-fucopyranoside) Type: Amphilectane diterpenoids. C28H40O7 Oil, [α]D = −52.1° (c = 1.3, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory. Ref: V. Roussis, et al, JOC, 1990, 55, 4916│ S. E. Lazerwith, et al, Org. Lett., 2000, 2, 2389

1

3

H HO

10

9

7

OO O HO

OH

O

3.26 Amphilectane Diterpenoids

31

87 Pseudopterosin I (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-(3-acetyl-α-L-fucopyranoside) Type: Amphilectane diterpenoids. C28H40O7 Oil, [α]D = −44° (c = 1.2, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory. Ref: V. Roussis, et al, JOC, 1990, 55, 4916│ S. E. Lazerwith, et al, Org. Lett., 2000, 2, 2389

1

3

H HO

10

9

7

OO HO HO

O O

88 Pseudopterosin J (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-(4-acetyl-α-L-fucopyranoside) Type: Amphilectane diterpenoids. C28H40O7 Oil, [α]D = −52.9° (c = 2.2, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory. Ref: V. Roussis, et al, JOC, 1990, 55, 4916│ S. E. Lazerwith, et al, Org. Lett., 2000, 2, 2389

1

3

H HO

10

9

7

OO HO O O

OH

89 Pseudopterosin K (1α,3β,7β)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-α-L-fucopyranoside Type: Amphilectane diterpenoids. C26H38O6 Oil, [α]D = −111° (c = 2.1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory; antibacterial (25 μg/mL for 6 mm disc, gram-positive bacteria Streptococcus pyogenes, IZD = 14 mm, MIC = 1.0 μg/mL; Staphylococcus aureus, IZD = 9 mm, MIC = 2.1 μg/mL;

32

3 Diterpenoids

Enterococcus faecalis, IZD = 8 mm, MIC = 3.4 μg/mL). Ref: V. Roussis, et al, JOC, 1990, 55, 4916│ A. Ata, et al, Helv. Chim. Acta 2004, 87, 1090

1

3

H HO

7

10

9

OO HO HO OH

90 Pseudopterosin L (1α,3β,7β)-8,10,12,14-Epiamphilectatetraene-9,10-diol 9-O-(3-acetyl-α-L-fucopyranoside) Type: Amphilectane diterpenoids. C28H40O7 Oil, [α]D = −112° (c = 1.1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory. Ref: V. Roussis, et al, JOC, 1990, 55, 4916

1

3

H HO

7 10

9

OO HO HO O O

91 Pseudopterosin P1aA Pseudopterosin Q1a4; Pseudopterosin P; (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene -9,10-diol 10-O-(4-O-acetyl-α-L-fucopyranoside) Type: Amphilectane diterpenoids. C28H40O7 Powder, [α]D25 = −53° (c = 0.56, MeOH), [α]D20 = −107.2° (c = 1.3, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA (phorbol 12-myristate 13-acetate): O2•−, IC50 > 10 μmol/L; TXB2, IC50 > 10 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 0.6 μmol/L). Ref: A. Ata, et al, Helv. Chim. Acta, 2004, 87, 1090│ I. I. Rodriguez, et al, JNP, 2004, 67, 1672│ C. Duque, et al, Tetrahedron, 2004, 60, 10627

3.26 Amphilectane Diterpenoids

1

33

3

H OO

9

7

OH

OH

O O

10

OH

92 Pseudopterosin P1bD (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9-acetoxy-10-ol 10-O-β-D-xylopyranoside Type: Amphilectane diterpenoids. C27H38O7 Gum, [α]D20 = +122° (c = 0.48, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antibacterial (25 μg/mL for 6 mm disc, selectively against gram-positive bacteria Streptococcus pyogenes, IZD = 15 mm, MIC = 0.8 μg/mL; Staphylococcus aureus, IZD = 10 mm, MIC = 2.0 μg/mL; Enterococcus faecalis, IZD = 8 mm, MIC = 3.5 μg/mL). Ref: A. Ata, et al, Helv. Chim. Acta, 2004, 87, 1090│ I. I. Rodriguez, et al, JNP, 2004, 67, 1672│ C. Duque, et al, Tetrahedron, 2004, 60, 10627

1

3

H OO

10

OH

9

7

O

OH OH

O

93 Pseudopterosin Q1a3 Pseudopterosin R1a1; Pseudopterosin Q; (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene -9,10-diol 10-O-(3-O-acetyl-α-L-fucopyranoside) Type: Amphilectane diterpenoids. C28H40O7 Powder, [α]D25 = −34° (c = 0.28, MeOH), [α]D20 = −43.6° (c = 1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA: O2•−, IC50 = 11.2 μmol/L; TXB2, IC50 = 4.7 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 3.4 μmol/L). Ref: A. Ata, et al, Helv. Chim. Acta, 2004, 87, 1090│ I. I. Rodriguez, et al, JNP, 2004, 67, 1672│ C. Duque, et al, Tetrahedron, 2004, 60, 10627

34

3 Diterpenoids

1

3

H OO

10

HO

9

7

OH

HO O

ALFUCOP

O

94 Pseudopterosin Q1b3 Pseudopterosin Q‡; (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9-acetoxy-10-ol 10O-(3-O-acetyl-β-D-xylopyranoside) Type: Amphilectane diterpenoids. C29H40O8 Gum, [α]D20 = +124° (c = 0.67, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antibacterial (25 μg/mL for 6 mm disc, selectively against grampositive bacteria Streptococcus pyogenes, IZD = 12 mm, MIC = 1.0 μg/mL; Staphylococcus aureus, IZD = 9 mm, MIC = 2.3 μg/mL; Enterococcus faecalis, IZD = 8 mm, MIC = 3.6 μg/mL); Ref: A. Ata, et al, Helv. Chim. Acta, 2004, 87, 1090│ I. I. Rodriguez, et al, JNP, 2004, 67, 1672│ C. Duque, et al, Tetrahedron, 2004, 60, 10627

1

3

H O

OO

10

O OH

9

7

O OH

O

BDXYLOP

95 Pseudopterosin T1aA Pseudopterosin Y; (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 10-O-α-Darabinopyranoside Type: Amphilectane diterpenoids. C25H36O6 Powder, [α]D25 = −38° (c = 0.89, MeOH), [α]D20 = −54.2° (c = 1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antimicrobial. Ref: I. I. Rodriguez, et al, JNP, 2004, 67, 1672│ C. Duque, et al, Tetrahedron, 2004, 60, 10627

3.26 Amphilectane Diterpenoids

1

35

3

O

OH HO

H O

OH

10

9

7

OH

ADARABP

96 Pseudopterosin U1a3 Pseudopterosin V1a3; Pseudopterosin V; (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene -9,10-diol 10-O-(3-O-acetyl-α-D-arabinopyranoside) Type: Amphilectane diterpenoids. C27H38O7 Powder, [α]D25 = −63° (c = 0.31, MeOH), [α]D20 = −78.3° (c = 1.2, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA (phorbol 12-myristate 13-acetate): O2•−, IC50 > 10 μmol/L; TXB2, IC50 > 10 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 2.2 μmol/L). Ref: I. I. Rodriguez, et al, JNP, 2004, 67, 1672│ C. Duque, et al, Tetrahedron, 2004, 60, 10627

O

1

3

O O HO OH

H O

10

9

7

ADARABP

97 Pseudopterosin U1a4 Pseudopterosin V1a4; Pseudopterosin U; (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene -9,10-diol 10-O-(4-O-acetyl-α-D-arabinopyranoside) Type: Amphilectane diterpenoids. C27H38O7 Powder, [α]D25 = −90° (c = 0.88, MeOH), [α]D20 = −32.9° (c = 1.1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA (phorbol 12-myristate 13-acetate): O2•−, IC50 = 11.2 μmol/L; TXB2, IC50 = 4.7 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 3.4 μmol/L). Ref: I. I. Rodriguez, et al, JNP, 2004, 67, 1672│ C. Duque, et al, Tetrahedron, 2004, 60, 10627

36

3 Diterpenoids

1

3

O

OH HO

H

O

O

10

ADARABP

9

7

OH

98 Pseudopterosin W (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 10-O-(3,4-di-O-acetyl-α-D-arabinopyranoside) Type: Amphilectane diterpenoids. C29H40O8 Amorph. solid, [α]D20 = −54.8° (c = 1.3, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antiinflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA (phorbol 12-myristate 13-acetate): O2•−, IC50 > 10 μmol/L; TXB2, IC50 > 10 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 10 μmol/L). Ref: I. I. Rodriguez, et al, JNP, 2004, 67, 1672

O

1

3

O O HO O

H O

10

ADARABP

O

9

7

OH

99 Pseudopterosin X (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9,10-diol 10-O-(2,4-di-O-acetyl-α-D-arabinopyranoside) Type: Amphilectane diterpenoids. C29H40O8 Oil, [α]D20 = −39° (c = 1.3, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA (phorbol 12-myristate 13acetate): O2•−, IC50 > 10 μmol/L; TXB2, IC50 > 10 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 2.35 μmol/L); antimicrobial. Ref: I. I. Rodriguez, et al, JNP, 2004, 67, 1672

1

O

O OH O

O

3

H O

ADARABP

10

9

OH

7

3.26 Amphilectane Diterpenoids

37

100 Pseudopteroxazole Type: Amphilectane diterpenoids. C21H27NO Yellowish oil, [α]D25 = +101° (c = 1, CHCl3). Source: Gorgonians Pseudopterogorgia elisabethae (Columbia) and Pseudopterogorgia elisabethae (West Indian Sea, Caribbean Sea). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, inhibitive rate = 97%). Ref: A. D. Rodriguez, et al, Org. Lett., 1999, 1, 527│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949│ T. W. Johnson, et al, JACS, 2001, 123, 4475│ J. P. Davidson, et al, JACS, 2003, 125, 13486 O N H

101 Secopseudopterosin A 7,8-Dihydroxyeriogorgiaene 8-O-α-L-arabinopyranoside Type: Amphilectane diterpenoids. C25H38O6 Amorph. solid, [α]D = −118° (c = 1.7, CHCl3). Source: Gorgonian Pseudopterogorgia sp. Pharm: Anti-inflammatory; analgesic. Ref: S. A. Look, et al, Tetrahedron, 1987, 43, 3363 O OH HO OH

ADARABP

O OH 8

H

102 Secopseudopterosin B 7,8-Dihydroxyeriogorgiaene 8-O-(2-O-acetyl-α-L-arabinopyranoside) Type: Amphilectane diterpenoids. C27H40O7 Unstable. Source: Gorgonian Pseudopterogorgia sp. Pharm: Anti-inflammatory; analgesic. Ref: S. A. Look, et al, Tetrahedron, 1987, 43, 3363

38

3 Diterpenoids

O O OH O ADARABP

OH

O OH 8

H

103 Secopseudopterosin C 7,8-Dihydroxyeriogorgiaene 8-O-(3-O-acetyl-α-L-arabinopyranoside) Type: Amphilectane diterpenoids. C27H40O7 Amorph. solid, [α]D = −89° (c = 0.58, CHCl3). Source: Gorgonian Pseudopterogorgia sp. Pharm: Anti-inflammatory; analgesic. Ref: S. A. Look, et al, Tetrahedron, 1987, 43, 3363 O O

O HO

OH

ADARABP

O OH 8

H

104 Secopseudopterosin D 7,8-Dihydroxyeriogorgiaene 8-O-(4-O-acetyl-α-L-arabinopyranoside) Type: Amphilectane diterpenoids. C27H40O7 Amorph. solid, [α]D = −139° (c = 0.6, CHCl3). Source: Gorgonian Pseudopterogorgia sp. Pharm: Anti-inflammatory; analgesic. Ref: S. A. Look, et al, Tetrahedron, 1987, 43, 3363

3.26 Amphilectane Diterpenoids

39

O OH HO ADARABP

O

O

O

OH 8

H

105 Sinulobatin A Type: Amphilectane diterpenoids. C22H30O3 Crystals (hexane), mp 126–128 °C, [α]D25 = +115.6° (c = 0.43, CHCl3). Source: Soft coral Sinularia nanolobata (Japan waters). Pharm: Cytotoxic (L1210, KB, IC50 = 3.0–7.7 μg/mL). Ref: K. Yamada, et al, Tetrahedron, 1997, 53, 4569 O

H

H O O

106 Sinulobatin B Type: Amphilectane diterpenoids. C20H28O Amorph., [α]D25 = +105.2° (c = 0.1, CHCl3). Source: Soft coral Sinularia nanolobata (Japan waters). Pharm: Cytotoxic (L1210, KB, IC50 = 3.0–7.7 μg/mL). Ref: K. Yamada, et al, Tetrahedron, 1997, 53, 4569 O

H

H

40

3 Diterpenoids

107 Sinulobatin C Type: Amphilectane diterpenoids. C22H32O3 Amorph. solid, [α]D25 = +98.2° (c = 0.23, CHCl3). Source: Soft coral Sinularia nanolobata (Japan waters). Pharm: Cytotoxic (L1210, KB, IC50 = 3.0–7.7 μg/mL). Ref: K. Yamada, et al, Tetrahedron, 1997, 53, 4569

O H

O

O

H H

H

3.27 Cycloamphilectane Diterpenoids 108 7,20-Diformamidoisocycloamphilectane Type: Cycloamphilectane diterpenoids. C22H36N2O2 Clear oil, [α]D25 = +17.4° (c = 0.13, CHCl3). Source: Sponge Cymbastela hooperi (Kelso Reef, Queensland, Australia). Pharm: Antiplasmodial (Plasmodium falciparum FCR3F86, IC50 = 14.8 μg/mL, control Atovaquone, IC50 = (0.4 ± 0.3)ng/mL). Ref: A. D. Wright, et al, JNP, 2009, 72, 492 H O H

H N H

H

H

H H

O N H

H

109 7-Formamido-11(20)-cycloamphilectene Type: Cycloamphilectane diterpenoids. C21H33NO Oil, [α]D25 = +13.7° (c = 0.49, CHCl3). Source: Sponge Cymbastela hooperi (Kelso Reef, Queensland, Australia). Pharm: Antiplasmodial (Plasmodium falciparum FCR3F86, IC50 > 100 μg/mL, control Atovaquone, IC50 = (0.4 ± 0.3)ng/mL). Ref: A. D. Wright, et al, JNP, 2009, 72, 492

3.27 Cycloamphilectane Diterpenoids

41

H H H

H H

O N H

H

110 7-Isocyano-11-cycloamphilectene Type: Cycloamphilectane diterpenoids. C21H31N Prisms (hexane), mp 115–116 °C, [α]D25 = +17° (c = 1.89, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 74.1 ng/mL, SI = 200, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 23.8 ng/mL, SI = 610, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 14500 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 H H H

H H

NC

111 7-Isocyano-10-cycloamphilectene Type: Cycloamphilectane diterpenoids. C21H31N Cryst. (hexane), mp 134.4–135.3 °C, [α]D25 = +80.4° (c = 0.53, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 84.9 ng/mL, SI > 240, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 28.4 ng/mL, SI > 700, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 > 20000 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 H H H

H H

NC

42

3 Diterpenoids

112 (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20-Isocyano-7isothiocyanatoisocycloamphilectane Type: Cycloamphilectane diterpenoids. C22H32N2S Oil, [α]D25 = +23.3° (c = 0.15, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 45.1 ng/mL, SI = 35.5, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 28.5 ng/mL, SI = 56.1, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 1600 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 H H CN

H

H

H H

NCS

113 Sinulobatin D Type: Cycloamphilectane diterpenoids. C24H34O4 Amorph., [α]D26 = +30.6° (c = 0.07, CHCl3). Source: Soft coral Sinularia nanolobata (Japan waters). Pharm: Cytotoxic (L1210, KB, IC50 = 3.0–7.7 μg/mL). Ref: K. Yamada, et al, Tetrahedron, 1997, 53, 4569 O O

O

O

H

H

3.28 Adociane Diterpenoids 114 7,20-Diisocyanoisocycloamphilectane 7,20-Diisocyanoadociane Type: Adociane diterpenoids. C22H32N2 Cryst. (hexane), mp 109–110 °C, [α]D22 = +47.4° (c = 0.7, CH2Cl2); mp 107.5–108.5 °C, [α]D25 = +43.8° (c = 0.64, CHCl3). Source: Sponges Adocia sp. (Great Barrier reef) and Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 4.7 ng/mL, SI = 1000, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 4.3 ng/mL, SI = 1100, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 4700 ng/mL, control Chloroquine, IC50 = 17400 ng/mL); antibacterial

3.28 Adociane Diterpenoids

43

(Escherichia coli and Vibrio harveyi, IC50 = 1–2.5 μg/mL). Ref: J. T. Baker, et al, JACS, 1976, 98, 4010│ R. Kazlauskas, et al, Tet. Lett., 1980, 21, 315│ C. J. R. Fookes, et al, J. Chem. Soc., Perken Trans, 1, 1988, 1003│ G. M. Koenig, et al, Magn. Reson. Chem., 1995, 33, 694│ G. M. König, et al, JOC, 1996, 61, 3259│ A. D. Wright, et al, Org. Biomol. Chem. 2011, 9, 400 17 16 11

CN

20

22

H

H

14

15

2 1

12

3

H

4 5

H 13 10

18

8

H 7

9

H

6

NC 19

21

115 7-Formamido-20-isocyanoisocycloamphilectane Type: Adociane diterpenoids. C22H34N2O Yellow oil, [α]D25 = +44° (c = 0.48, CHCl3). Source: Sponge Cymbastela hooperi (Kelso Reef, Queensland, Australia). Pharm: Antiplasmodial (Plasmodium falciparum：FCR3F86, IC50 = 0.2 μg/mL, control Atovaquone, IC50 = (0.4 ± 0.3)ng/mL; W2, IC50 = 0.6 μg/mL, Atovaquone, IC50 = 0.8 ng/mL; D6, IC50 = 0.8 μg/mL, Atovaquone, IC50 = 0.2 ng/mL; mean of three strains, IC50 = (0.5 ± 0.3)μg/mL, Atovaquone, IC50 = (0.5 ± 0.4)ng/mL); cytotoxic (KB, IC50 > 5 μg/mL, control Atovaquone, IC50 > 5 ng/mL). Ref: A. D. Wright, et al, JNP, 2009, 72, 492 H CN

H

H H

H H

O N H

H

116 (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20-Isocyano-7isocyanoisocycloamphilectane Type: Adociane diterpenoids. C22H32N2O Oil, [α]D25 = +36.1° (c = 0.75, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 74.9 ng/mL, SI = 26.7, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 56.1 ng/mL, SI = 35.7, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 2000 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259

44

3 Diterpenoids

H H CN

H

H

H H

NCO

117 (1S*,3S*,4R*,7S,8S*,11R*,12R*,13S*,20S*)-7-Isocyanoisocycloamphilect-14-ene Type: Adociane diterpenoids. C21H31N Cryst. (hexane), mp 124.3–125.6 °C, [α]D25 = +4.9° (c = 0.53, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 62.5 ng/mL, SI = 290, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 19.5 ng/mL, SI = 930, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 18200 ng/mL, control Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 H H H

H

H H

NC

118 (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20-Isocyanato-7isocyanoisocycloamphilectane Type: Adociane diterpenoids. C22H32N2O Oil, [α]D25 = +37.0° (c = 0.58, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 = 3.2 ng/mL, SI = 1340, control Chloroquine, IC50 = 3.8 ng/mL, SI = 4600; W2, IC50 = 2.5 ng/mL, SI = 1710, Chloroquine, IC50 = 50.5 ng/mL, SI = 340); cytotoxic (KB, IC50 = 4300 ng/mL, Chloroquine, IC50 = 17400 ng/mL). Ref: G. M. König, et al, JOC, 1996, 61, 3259 H H OCN

H

H

H H

NC

3.29 Xenicane Diterpenoids

45

3.29 Xenicane Diterpenoids 119 Acalycigorgin A Type: Xenicane diterpenoids. C25H34O7 Oil, [α]D20 = +82.3° (c = 0.4, CHCl3). Source: Gorgonian Acalycigorgia sp. (Japan waters). Pharm: Inhibits cell division (fertilized ascidian eggs); toxic (brine shrimp). Ref: M. Ochi, et al, Heterocycles, 1993, 36, 41│ M. Ochi, et al, Heterocycles, 1994, 38, 151 O

O

O O

H O

H O

O

120 Acalycigorgin B Type: Xenicane diterpenoids. C25H34O8 Oil, [α]D21 = +70.8° (c = 0.13, CHCl3). Source: Gorgonian Acalycigorgia sp. (Japan waters). Pharm: Inhibits cell division (fertilized ascidian eggs); toxic (brine shrimp). Ref: M. Ochi, et al, Heterocycles, 1993, 36, 41│ M. Ochi, et al, Heterocycles, 1994, 38, 151 O

O

O O

H O

O

H O

O

121 Acalycigorgin C Type: Xenicane diterpenoids. C20H28O2 Oil, [α]D21 = +40.3° (c = 0.28, CHCl3). Source: Gorgonian Acalycigorgia sp. (Japan waters). Pharm: Inhibits cell division (fertilized ascidian eggs); toxic (brine shrimp). Ref: M. Ochi, et al, Heterocycles, 1993, 36, 41│ M. Ochi, et al, Heterocycles, 1994, 38, 151

46

3 Diterpenoids

H O

H O

122 Acalycigorgin D Type: Xenicane diterpenoids. C23H34O4 Source: Gorgonian Acalycigorgia sp. (Japan waters). Pharm: Inhibits cell division (fertilized ascidian eggs); toxic (brine shrimp). Ref: M. Ochi, et al, Heterocycles, 1994, 38, 151

H

O O

H O

O

123 Acalycigorgin E Type: Xenicane diterpenoids. C20H30O2 Amorph. solid, [α]D21 = +51.4°, (c = 0.16, CHCl3). Source: Gorgonian Acanthogorgia turgida (Grandi I., Goa, India) and Acanthogorgia sp. (Japan waters). Pharm: Inhibits cell division (fertilized ascidian eggs); toxic (brine shrimp). Ref: E. Manzo, et al, Nat. Prod. Res., 2009, 23, 1664│ M. Ochi, et al, Heterocycles, 1994, 38, 151

O

H

H

O H

124 Acalycixeniolide H Type: Xenicane diterpenoids. C21H30O5 Amorph. solid, mp 162–164 °C, [α]D = +156.5° (c = 0.11, MeOH). Source: Gorgonian Acalycigorgia inermis. Pharm: Cytotoxic (K562, LC50 = 3.9 μg/mL). Ref: J. R. Rho, et al, JNP, 2001, 64, 540

3.29 Xenicane Diterpenoids

O

47

O

H

O

H

O

O

H

125 Acalycixeniolide I Type: Xenicane diterpenoids. C20H30O3 Amorph. solid, mp 95–98 °C, [α]D = +103.9° (c = 0.35, MeOH). Source: Gorgonian Acalycigorgia inermis. Pharm: Cytotoxic (K562, LC50 = 1.2 μg/mL). Ref: J. R. Rho, et al, JNP, 2001, 64, 540 OH

H

O O

H

126 Acalycixeniolide J Type: Xenicane diterpenoids. C20H30O3 Amorph. solid, mp 93–95 °C, [α]D25 = +49.4° (c = 0.14, MeOH). Source: Gorgonian Acalycigorgia inermis. Pharm: Cytotoxic (K562, LC50 = 2.0 μg/mL). Ref: J. R. Rho, et al, JNP, 2001, 64, 540 OH

H

O O

H

127 Antheliatin Type: Xenicane diterpenoids. C33H40O10 Cryst. (MeOH), mp 165 °C, [α]D = +3.5° (c = 1.2, CHCl3). Source: Soft coral Anthelia glauca (South Africa). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL, A549, IC50 = 1 μg/mL; MEL28, IC50 = 1 μg/mL; HT29, IC50 = 0.1 μg/mL). Ref: A. Rudi, et al, JNP, 1995, 58, 1581

48

3 Diterpenoids

O 12

O

11

O

O H

O O

O

O

8

18

O

H OH

128 Asterolaurin A Type: Xenicane diterpenoids. C26H36O10 Source: Soft coral Asterospicularia laurae (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 = 8.9 μmol/L). Ref: Y. C. Lin, et al, JNP, 2009, 72, 1911 15

O

O O 12

H

3

1

O

18

5

4a 11a

O O

O H

8

11

O OH

H OH

19

129 Asterolaurin B Type: Xenicane diterpenoids. C26H36O9 Source: Soft coral Asterospicularia laurae (Taiwan waters). Pharm: Anti-inflammatory (10 μg/mL, hmn neutrophils in response to fMLP/CB: elastase release inhibition assay, InRt = 30%, control Genistein, InRt = 52%; superoxide anion generation assay, InRt = 31%, control Genistein, InRt = 65%). Ref: Y. C. Lin, et al, JNP, 2009, 72, 1911

O

O O H

HO

O O

O

O

H

OH

3.29 Xenicane Diterpenoids

49

130 Asterolaurin C Type: Xenicane diterpenoids. C26H36O9 Source: Soft coral Asterospicularia laurae (Taiwan waters). Pharm: Anti-inflammatory (10 μg/mL, hmn neutrophils in response to fMLP/CB: elastase release inhibition assay, InRt = 39%, control Genistein, InRt = 52%; superoxide anion generation assay, InRt = 22%, control Genistein, InRt = 65%). Ref: Y. C. Lin, et al, JNP, 2009, 72, 1911

O

O O H

HO

O O

O

O

OH

H

131 Asterolaurin D Type: Xenicane diterpenoids. C22H32O5 Source: Soft coral Asterospicularia laurae (Taiwan waters). Pharm: Anti-inflammatory (10 μg/mL, hmn neutrophils in response to fMLP/CB: elastase release inhibition assay, InRt = 68%, control Genistein, InRt = 52%, IC50 = 18.7 μmol/L; superoxide anion generation assay, InRt = 56%, control Genistein, InRt = 65%, IC50 = 23.6 μmol/L). Ref: Y. C. Lin, et al, JNP, 2009, 72, 1911 OH

H O H OH

O O

132 Asterolaurin E Type: Xenicane diterpenoids. C24H32O8 Source: Soft coral Asterospicularia laurae (Taiwan waters). Pharm: Anti-inflammatory (10 μg/mL, hmn neutrophils in response to fMLP/CB: elastase release inhibition assay, InRt = 36%, control Genistein, InRt = 52%; superoxide anion generation assay, InRt = 24%, control Genistein, InRt = 65%). Ref: Y. C. Lin, et al, JNP, 2009, 72, 1911

50

3 Diterpenoids

O H

O

OH

O

O

O

H OH

O

133 Asterolaurin F Type: Xenicane diterpenoids. C22H30O6 Source: Soft coral Asterospicularia laurae (Taiwan waters). Pharm: Anti-inflammatory (10 μg/mL, hmn neutrophils in response to fMLP/CB: elastase release inhibition assay, InRt = 13%, control Genistein, InRt = 52%; superoxide anion generation assay, InRt = 9%). Ref: Y. C. Lin, et al, JNP, 2009, 72, 1911

H

O

OH

O

O

H OH

O

134 Asterolaurin L (1aS,3aS,4E,7S,7aR,10R)-Dodecahydro-4-[(2E)-4-hydroxy-4-methylpent-2-en-1-ylidene]1a-methyl-8-methylideneoxireno[5,6]cyclonona[1,2-c]pyran-7,10-diol Type: Xenicane diterpenoids. C20H30O5 White solid, [α]D25 = +4.4° (c = 0.5, CH2Cl2). Source: Soft coral Asterospicularia laurae (Southeastern Taiwan). Pharm: Cytotoxic (Hep2, ED50 = 4.12 μg/mL; Doay, ED50 = 6.23 μg/mL; MCF7, ED50 = 4.09 μg/mL; WiDr, ED50 = 6.08 μg/mL). Ref: Y. -S. Lin, et al, Chem. Biodiversity, 2011, 8, 1310 OH

H O

O OH

H

OH

3.29 Xenicane Diterpenoids

51

135 Blumiolide A Type: Xenicane diterpenoids. C20H28O4 Oil, [α]D25 = +18° (c = 0.4, CHCl3). Source: Soft coral Xenia blumi, soft coral Xenia blumi (Green I., Taiwan). Pharm: Cytotoxic (hmn HT29, ED50 = 4.6 μg/mL; mouse P388, ED50 = 3.3 μg/mL). Ref: A. A. H. El-Gamal, et al, JNP, 2005, 68, 1336 OH

H

12E

H

O

10E

H

O H

136 Blumiolide B (7β,10E,12 E)-7,14-Dihydroxy-1(19),6(20),10,12-xenicatetraen-18,17-olide Type: Xenicane diterpenoids. C20H28O4 Oil, [α]D25 = +33° (c = 0.4, CHCl3). Source: Soft coral Xenia blumi, soft coral Xenia blumi (Green I., Taiwan). Pharm: Cytotoxic (HT29, ED50 = 4.9 μg/mL; P388, ED50 = 3.7 μg/mL). Ref: A. A. H. El-Gamal, et al, JNP, 2005, 68, 1336 OH H

12E

H 10E

O O

OH

8

1

H

137 Blumiolide C Type: Xenicane diterpenoids. C20H26O4 Oil, [α]D25 = +66° (c = 0.4, CHCl3). Source: Soft coral Xenia blumi (Green I., Taiwan). Pharm: Cytotoxic (HT29, ED50 = 0.5 μg/mL; P388, ED50 = 0.2 μg/mL). Ref: A. A. H. El-Gamal, et al, JNP, 2005, 68, 1336 HO H H

O

6Z

10Z

O

1

H

8

O

52

3 Diterpenoids

138 Cristaxenicin A Type: Xenicane diterpenoids. C24H30O7 Source: Coelenterate Acanthoprimnoa cristata (dredging, Yakushima-Shinsone, Kagoshima, Japan). Pharm: Antileishmanial (Leishmania amazonesis, modest selectivity, sub-micromolar activity); antitrypanosomal (Trypanosoma congolense, sub-micromolar activity); Antiplasmodial (Plasmodium falciparum). Ref: S. -T. Ishigami, et al, JOC, 2012, 77, 10962

O

O

H

H

O O

O

H

O O

139 9-Deoxy-7,8-epoxy-isoxeniolide A Type: Xenicane diterpenoids. C20H28O4 Oil, [α]D25 = +26° (c = 0.2, CHCl3). Source: Soft coral Xenia blumi (Green I., Taiwan). Pharm: Cytotoxic (HT29, ED50 = 5.6 μg/mL; P388, ED50 = 4.7 μg/mL). Ref: A. A. H. El-Gamal, et al, JNP, 2005, 68, 1336 HO

H

O

H

O

O

H

140 8-Deoxyxeniolide A 9-Deoxyxeniolide A Type: Xenicane diterpenoids. C20H28O3 Source: Soft coral Xenia sp. (Philippines). Pharm: Antibacterial. Ref: H. C. Vervoort, et al, Nat. Prod. Lett., 1995, 6, 49 OH

O

H O

H

3.29 Xenicane Diterpenoids

53

141 Deoxyxeniolide B Type: Xenicane diterpenoids. C20H28O2 Amorph. solid, mp 40–42 °C, [α]D27 = −22.4° (c = 0.96, CHCl3). Source: Soft coral Xenia elongata (Japan waters). Pharm: Ichthyotoxic. Ref: T. Miyamoto, et al, JNP, 1995, 58, 924

H O

H O

142 8-Deoxyxeniolide B 9-Deoxyxeniolide B Type: Xenicane diterpenoids. C20H28O3 Source: Soft coral Xenia sp. (Philippines). Pharm: Antibacterial. Ref: H. C. Vervoort, et al, Nat. Prod. Lett., 1995, 6, 49 OH

H O

H O

143 Dictyodial 1(9),6,13-Xenicatriene-18,19-dial Type: Xenicane diterpenoids. C20H30O2 Oil, [α]D25 = −95° (c = 1.2, CHCl3). Source: Brown algae Dictyota crenulata, Dictyota flabellata, Dictyota patens and Dilophus mediterraneus, sea hare Aplysia depilans. Pharm: HIV reverse transcriptase (HIV-rt) inhibitor; algicide. Ref: J. Finer, et al, JOC, 1979, 44. 2044│ J. F. Blount, et al, Aust. J. Chem., 1982, 35, 145│ H. Nagaoka, et al, Tet. Lett., 1988, 29, 5945

H O O

54

3 Diterpenoids

144 Dictyoepoxide Type: Xenicane diterpenoids. C22H36O4 Oil. Source: Brown alga Dictyota sp. (Mexico). Pharm: Vasopressin receptor antagonist; norepinephrin inhibitor. Ref: A. D. Patil, et al, Phytochemistry, 1993, 33, 1061

H O

H

O

O O

145 Dictyolactone 1(9),6,13-Xenicatrien-19,18-olide Type: Xenicane diterpenoids. C20H30O2 Cryst. (hexane), mp 64–65 °C, [α]D25 = −165° (c = 0.94, MeOH). Source: Brown algae Dilophus lingulatus and Dictyota dichotoma, sea hare Aplysia depilans. Pharm: Vasopressin-V1 receptor antagonist; norepinephrine antagonist. Ref: J. Finer, et al, JOC, 1979, 44, 2044

H

O O

146 Dilophic acid 1(9),6,13-Xenicatrien-18-oic acid Type: Xenicane diterpenoids. C20H32O2 Oil, [α]D25 = −116° (c = 2.35, CHCl3). Source: Brown alga Dilophus guineensis. Pharm: Ichthyotoxin. Ref: D. Schlenk, et al, Phytochemistry, 1987, 26, 1081

3.29 Xenicane Diterpenoids

55

H O OH

147 Dilopholide Type: Xenicane diterpenoids. C22H32O4 Oil, [α]D = −113.7° (c = 0.86, CHCl3). Source: Brown alga Dilophus ligulatus (Mediterranean Sea). Pharm: Cytotoxic (KB, ED50 = 1.50 μg/mL, P388, ED50 = 0.50 μg/mL, P388/Dox, ED50 = 12.00 μg/mL, NSCLC-N6, ED50 = 3.30 μg/mL, control Mercaptopurine: KB, ED50 = 0.54 μg/mL, P388, ED50 = 0.70 μg/mL, P388/Dox, ED50 = 0.25 μg/mL, NSCLC-N6, ED50 = 0.67 μg/mL). Ref: N. Bouaicha, et al, JNP, 1993, 56, 1747 O

O

O

H

O

148 7,8-Epoxyzahavin A 6,7-Epoxyzahavin A Type: Xenicane diterpenoids. C26H36O8 Oil, [α]D21 = +121.7° (c = 0.34, CHCl3). Source: Soft coral Eleutherobia aurea (South Africa). Pharm: Antioxidant (rbt cell neutrophils, inhibits superoxide production). Ref: G. J. Hooper, et al, JNP, 1997, 60, 889 O O

O O H

O

O

O O

H

56

3 Diterpenoids

149 Florlide D (6α,7β,10E,12E)-6,7-Epoxy-1(19),10,12-xenicatrien-18,17-olide Type: Xenicane diterpenoids. C20H28O3 Needles, mp 178 °C, [α]D = +178° (c = 0.09, MeOH). Source: Soft coral Xenia florida (Japan waters). Pharm: Antibacterial (Staphylococcus aureus and Aeromonas salmonisida). Ref: T. Iwagawa, et al, JNP, 1998, 61, 1513

14

12

O

6

10

7

O

1

O

H

19

150 Fukurinolal Hydroxyacetyldictyolal Type: Xenicane diterpenoids. C22H34O4 Crystal, mp 79–80 °C, [α]D18 = −189° (c = 0.20, CHCl3). Source: Brown algae Dictyota dichotoma, Dilophus okamurai, Dictyota crenulata and Dilophus ligulatus (Mediterranean Sea). Pharm: Cytotoxic (KB, ED50 = 2.10 μg/mL, P388, ED50 = 3.90 μg/mL, P388/Dox, ED50 = 9.30 μg/mL, NSCLC-N6, ED50 = 10.00 μg/mL, control Mercaptopurine: KB, ED50 = 0.54 μg/mL, P388, ED50 = 0.70 μg/mL, P388/Dox, ED50 = 0.25 μg/mL, NSCLC-N6, ED50 = 0.67 μg/mL). Ref: N. Enoki, et al, Chem. Lett., 1982, 1749│ M. Ochi, et al, Chem. Lett., 1982, 1927│ M. P. Kirkup, et al, Phytochernistry, 1983, 22, 2539│ N. Bouaicha,et al, JNP, 1993, 56, 1747 O O H O

18

OH

H

7

6

151 Hydroxydictyodial 4-Hydroxy-1(9),6,13-xenicatriene-18,19-dial Type: Xenicane diterpenoids. C20H30O3 Cryst. or oil, mp 79–81 °C, [α]D = −256° (c = 2.41, CHCl3), [α]D25 = −121° (c = 0.33, EtOH). Source: Brown alga Dictyota spinulosa. Pharm: Antimicrobial; antifeedant (inhibits feeding in omnivorous fish Tilapia mossambica at 1% in food). Ref: M. P. Kirkup, et al, Phytochernistry, 1983, 22, 2539│ J. Tanaka, et al, Chem. Lett., 1984, 231

3.29 Xenicane Diterpenoids

57

OH

H O O

152 Novaxenicin B Type: Xenicane diterpenoids. C20H30O6 Oil, [α]D22 = −37° (c = 1.81, CHCl3). Source: Soft coral Xenia novaebrittanniae (Kenya). Pharm: Inducer of apoptosis (transformed mammalian cells, 1.25 μg/mL). Ref: A. Bishara, et al, Tetrahedron 2006, 62, 12092

HO

OH

15

14

H 12

O H

13 4

O

OH

H 4a

1

18

7 11

O

H 19

153 Tsitsixenicin A Type: Xenicane diterpenoids. C24H34O5 Yellow oil, [α]D17 = −64° (c = 0.9, CHCl3). Source: Soft coral Capnella thyrsoidea (South Africa, two variants). Pharm: Antioxidant (superoxide anion scavenger, in both rbt and hmn cell neutrophils). Ref: G. J. Hooper, et al, Tetrahedron, 1995, 51, 9973

O 11

O H

O

18

O

6 7

H

O

154 Tsitsixenicin B Type: Xenicane diterpenoids. C24H34O6 Oil, [α]D21 = −38° (c = 0.49, CHCl3). Source: Soft coral Capnella thyrsoidea (South Africa, two variants). Pharm: Antioxidant

58

3 Diterpenoids

(superoxide anion scavenger, in both rbt and hmn cell neutrophils). Ref: G. J. Hooper, et al, Tetrahedron, 1995, 51, 9973

O 11

O H

O

O

18

O

6

7

H

O

155 Tsitsixenicin C Type: Xenicane diterpenoids. C24H32O7 Oil, [α]D21 = −138.9° (c = 0.6, CHCl3). Source: Soft coral Capnella thyrsoidea (South Africa, two variants). Pharm: Antioxidant (superoxide anion scavenger). Ref: G. J. Hooper, et al, Tetrahedron, 1995, 51, 9973 HO 11

O H

O 6

O

O

18

O

H

O

156 Tsitsixenicin D Type: Xenicane diterpenoids. C24H32O6 Oil, [α]D21 = −126° (c = 0.8, CHCl3). Source: Soft coral Capnella thyrsoidea (South Africa, two variants). Pharm: Antioxidant (superoxide anion scavenger). Ref: G. J. Hooper, et al, Tetrahedron, 1995, 51, 9973

11

O H

O 6

O

O O

O

18

H

3.29 Xenicane Diterpenoids

59

157 Xeniolactone B 9-Deoxy-7,8-epoxy-xeniolide A Type: Xenicane diterpenoids. C20H28O4 Oil, [α]D25 = +28° (c = 0.3, CHCl3), [α]D25 = +68° (c = 0.3, CH2Cl2). Source: Soft corals Xenia blumi (Green I., Taiwan) and Xenia florida. Pharm: Cytotoxic (HT29, ED50 = 8.6 μg/ mL; P388, ED50 = 6.9 μg/mL). Ref: Y. -C. Shen, et al, Tet. Lett., 2005, 46, 4793│ A. A. H. El-Gamal, et al, JNP, 2005, 68, 1336 OH

H

O

O

H

O H

158 Xeniolide I Type: Xenicane diterpenoids. C20H28O6 Oil, [α]D22 = +41° (c = 0.17, CHCl3). Source: Soft coral Xenia novaebrittanniae (Kenya). Pharm: Antibacterial (Escherichia coli ATCC and Bacillus subtilis, 1.25 μg/mL). Ref: A. Bishara, et al, Tetrahedron 2006, 62, 12092 O 12

H

O

OH

OH 7

O

O H 19

159 Zahavin A Type: Xenicane diterpenoids. C26H36O7 Viscous oil, [α]D20 = +7.3° (c = 1.8, CHCl3). Source: Soft corals Alcyonium aureum (South Africa) and Anthelia glauca. Pharm: Cytotoxic (P388, IC50 = 1 μg/mL, A549, IC50 = 1 μg/mL; MEL28, IC50 = 1 μg/mL; HT29, IC50 = 1 μg/mL); superoxide release inhibitor. Ref: A. Rudi, et al, JNP, 1995, 58, 1581

60

3 Diterpenoids

O O

O O

H O O

H O

160 Zahavin B Type: Xenicane diterpenoids. C26H36O8 Viscous oil, [α]D20 = +4.8° (c = 0.7, CHCl3). Source: Soft corals Alcyonium aureum (South Africa) and Anthelia glauca. Pharm: Cytotoxic (P388, IC50 = 1 μg/mL, A549, IC50 = 1 μg/mL; MEL28, IC50 = 1 μg/mL; HT29, IC50 = 1 μg/mL). Ref: A. Rudi, et al, JNP, 1995, 58, 1581 O O

O O

H H

O O

O

OH

161 Acalycixeniolide A Type: Nor-, seco- and cycloxenicane diterpenoids. C19H28O2 Amorph. powder, [α]D = +143° (c = 0.31, CHCl3). Source: Gorgonian Acalycigorgia inermis. Pharm: Starfish egg division inhibitor. Ref: Y. Fusetani, et al, Tet. Lett., 1987, 28, 5837

13

H

O

10

O H

162 Acalycixeniolide B Type: Nor-, seco- and cycloxenicane diterpenoids. C19H26O2 Source: Gorgonians Acanthogorgia turgida (Grandi I., Goa, India) and Acalycigorgia inermis. Pharm:

3.29 Xenicane Diterpenoids

61

Inhibits cell division (fertilised starfish eggs). Ref: E. Manzo, et al, Nat. Prod. Res., 2009, 23, 1664│ N. Fusetani, et al, Tet. Lett., 1987, 28, 5837

H

O O

H

163 Acalycixeniolide C‡ Type: Nor-, seco- and cycloxenicane diterpenoids. C19H26O3 Amorph. solid, mp 91–93 °C, [α]D25 = 43.2° (c = 0.4, MeOH). Source: Gorgonian Acalycigorgia inermis (Korea waters). Pharm: Cytotoxic (K562, LC50 = 1.6 μg/mL). Ref: J. -R. Rho, et al, JNP, 2000, 63, 254 [erratum JNP, 2000, 63, 1051]

E

O

O O

H

164 Acalycixeniolide D Type: Nor-, seco- and cycloxenicane diterpenoids. C19H24O3 Amorph. solid, mp 87–90 °C, [α]D25 = 162.7° (c = 0.1, MeOH). Source: Gorgonian Acalycigorgia inermis (Korea waters). Pharm: Cytotoxic (K562, LC50 = 52.0 μg/mL). Ref: J. -R. Rho, et al, JNP, 2000, 63, 254; 1051

E

O

O O

H

165 Acalycixeniolide E Type: Nor-, seco- and cycloxenicane diterpenoids. C23H30O6 Colorless gum, [α]D25 = 41.5° (c = 0.3, MeOH). Source: Gorgonian Acalycigorgia inermis (Korea waters).

62

3 Diterpenoids

Pharm: Cytotoxic (K562, LC50 = 4.7 μg/mL). Ref: J. -R. Rho, et al, JNP, 2000, 63, 254 [erratum JNP, 2000, 63, 1051] O O O O O

H O

166 Acalycixeniolide F Type: Nor-, seco- and cycloxenicane diterpenoids. C20H30O3 Colorless gum, [α]D25 = 46.8° (c = 0.1, MeOH). Source: Gorgonian Acalycigorgia inermis (Korea waters). Pharm: Cytotoxic (K562, LC50 = 0.2 μg/mL). Ref: J. -R. Rho, et al, JNP, 2000, 63, 254 [erratum JNP, 2000, 63, 1051]

O

O O

H

167 Acalycixeniolide K Type: Nor-, seco- and cycloxenicane diterpenoids. C19H28O3 Amorph. solid, mp 127–129 °C, [α]D25 = +36.8° (c = 0.1, MeOH). Source: Gorgonian Acalycigorgia inermis. Pharm: Cytotoxic (K562, LC50 = 1.8 μg/mL). Ref: J. R. Rho, et al, JNP, 2001, 64, 540 OH H

O O

H

168 Acalycixeniolide L Type: Nor-, seco- and cycloxenicane diterpenoids. C19H28O3 Amorph. solid, mp 137–140 °C, [α]D25 = +47° (c = 0.12, MeOH). Source: Gorgonian Acalycigorgia inermis. Pharm: Cytotoxic (K562, LC50 = 1.5 μg/mL). Ref: J. R. Rho, et al, JNP, 2001, 64, 540

3.29 Xenicane Diterpenoids

63

OH

H

O O

H

169 4-Acetoxycrenulide Type: Nor-, seco- and cycloxenicane diterpenoids. C22H32O4 [α]D26 = +13° (CHCl3); [α]D23 = +20.1° (c = 0.08, CHCl3). Source: Brown algae Dictyota crenulata and Dilophus ligulatus (Mediterranean Sea). Pharm: Cytotoxic (KB, ED50 > 10 μg/mL, P388, ED50 > 10 μg/mL, P388/Dox, ED50 > 10 μg/mL, NSCLC-N6, ED50 > 10 μg/mL). Ref: H. H. Sun, et al, JOC, 1983, 48, 1903│ S. L. Midland, et al, JOC, 1983, 48, 1906│ N. Bouaicha, et al, JNP, 1993, 56, 1747│ L. A. Paquette, et al, JACS, 1995, 117, 1455│ T. -Z. Wang, et al, JACS, 1996, 118, 1309

14

O 12

O H 4

18

O O

170 Florlide B Type: Nor-, seco- and cycloxenicane diterpenoids. C20H30O4 Amorph. solid, [α]D = +150° (c = 0.08, MeOH). Source: Soft coral Xenia florida (Japan waters). Pharm: Antibacterial (Staphylococcus aureus and Aeromonas salmonisida). Ref: T. Iwagawa, et al, JNP, 1998, 61, 1513

H O

OH O

H

OH

64

3 Diterpenoids

3.30 Prenyleudesmane Diterpenoids 171 Aplysiadiol Type: Prenyleudesmane diterpenoids. C20H31BrO2 Oil, [α]D20 = −50.8° (c = 0.44, CHCl3). Source: Red algae Laurencia sp. (N. Borneo I., Sabah, Malaysia) and Laurencia japonensis, sea hare Aplysia kurodai. Pharm: Antibacterial (30mg/disc: Staphylococcus aureus, IZD = 8 mm, MIC = 200 μg/mL; Staphylococcus sp., IZD = 10 mm, MIC = 125 μg/mL; Salmonella sp., IZD = 9 mm, MIC = 250 μg/mL). Ref: M. Ojika,et al, Phytochemistry 1982, 21, 2410│ M. Ojika, et al, JNP, 1990, 53, 1619│ Y. Takahashi, et al, Phytochemistry, 1998, 48, 987│ C. S. Vairappan, et al, Mar. Drugs, 2010, 8, 1743 Br

OH

OH

3.31 Prenylgermacrane Diterpenoids 172 Eunicol Type: Prenylgermacrane diterpenoids. C20H32O Colorless viscous oil, [α]D29 = −15° (c = 0.15, CHCl3), [α]D20 = −22.8° (c = 0.00395, CH2Cl2). Source: Gorgonian Eunicea fusca, soft coral Lobophytum pauciflorum (Taketomijima I., Okinawa). Pharm: Cytotoxic (A431 hmn epidermic cancer cells, IC50 = 0.35 μmol/L). Ref: J. C. Coll, et al, Bull. Soc. Chim. Belg. 1986, 95, 815│ M. B. Saleh, et al, Aust. J. Chem., 2010, 63, 901│ S. V. S. Govindam, et al, BoMC, 2012, 20, 687

OH

173 Lobocompactol A Type: Prenylgermacrane diterpenoids. C20H32O3 Source: Soft coral Lobophytum compactum (Bay Canh I., Khanh Hoa, Vietnam). Pharm: Antioxidant (peroxy radical scavenger, 5 μmol/L, 1.4 μmol/L Trolox equivalent). Ref: C. V. Minh, et al, BoMCL, 2011, 21, 2155

3.32 Prenylbicyclogermacrane Diterpenoids

HO

65

H O

OH

174 Lobocompactol B Type: Prenylgermacrane diterpenoids. C20H32O3 Source: Soft coral Lobophytum compactum (Bay Canh I., Khanh Hoa, Vietnam). Pharm: Antioxidant (peroxy radical scavenger, 5 μmol/L, 1.4 μmol/L Trolox equivalent). Ref: C. V. Minh, et al, BoMCL, 2011, 21, 2155

HO

H O OH

3.32 Prenylbicyclogermacrane Diterpenoids 175 Faraunatin Type: Prenylbicyclogermacrane diterpenoids. C20H32O Source: Soft coral Xenia faraunensis (Red Sea). Pharm: Cytotoxic (P388). Ref: Y. Kashman, et al, Tet. Lett., 1994, 35, 8855

H

H

OH

176 Palmatol Type: Prenylbicyclogermacrane diterpenoids. C20H34O Crystals (hexane), mp 93–94 °C, [α]D20 = −94.7° (c = 2.5, CHCl3). Source: Soft coral Alcyonium palmatum (Mediterranean Sea). Pharm: Ichthyotoxic; toxic (brine shrimp). Ref: E. Zubia, et al, Tet. Lett., 1994, 35, 7069

66

3 Diterpenoids

H HO H

3.33 Lobane Diterpenoids 177 Cyclolobatriene Type: Lobane diterpenoids. C20H32O2 Colorless viscous oil, [α]D26 = +57° (c = 0.139, CHCl3). Source: Soft coral Lobophytum pauciflorum (Taketomijima I., Okinawa). Pharm: Cytotoxic (A431 hmn epidermic cancer cells, IC50 = 0.64 μmol/L). Ref: S. V. S. Govindam, et al, BoMC, 2012, 20, 687

O

OH

178 Dictyoxepin 9,11-Epoxy-17-loben-3-ol Type: Lobane diterpenoids. C20H32O2 Source: Brown alga Dictyota acutiloba. Pharm: Algicide. Ref: H. H. Sun, et al, JACS, 1977, 99, 3516

O

H H

OH

179 17R,18-Epoxy-8,10,13(15)-lobatriene Type: Lobane diterpenoids. C20H32O Yellow oil. Source: Soft coral Lobophytum sp. Pharm: Toxic to brine shrimp. Ref: R. W. Dunlop, et al, Aust. J. Chem., 1979, 32, 1345

O

3.33 Lobane Diterpenoids

67

180 14,18-Epoxyloba-8,10,13(15)-trien-17-ol Type: Lobane diterpenoids. C20H32O2 Viscous oil. Source: Soft corals Sinularia sp. (Bowden Reef, Great Barrier Reef) and Lobophytum pauciflorum. Pharm: Antifungal (phytopathogenic fungus Cladosporium cucumerinum). Ref: V. Anjaneyulu, et al, Indian J. Chem., Sect. B, 1993, 32, 1198│ R. U. Edrada, et al, JNP, 1998, 61, 358│ A. D. Wright, et al, Mar. Drugs, 2012, 10, 1619

H

OH O

181 14,17-Epoxyloba-8,10,13(15)-trien-18-ol acetate Type: Lobane diterpenoids. C22H34O3 Yellow viscous oil or colourless oil, [α]D = + 47.3° (c = 0.31, CHCl3). Source: Soft corals Sinularia sp. (Bowden Reef, Great Barrier Reef) and Lobophytum pauciflorum. Pharm: Cytotoxic (SF268, GI50 = 14 μmol/L, breast-pleural effusion adenocarcinoma cells, GI50 = 16 μmol/L, Lung large cell carcinoma cells, GI50 = 18.5 μmol/L); toxic (brine shrimp). Ref: R. A. Edrada, et al, JNP, 1998, 61, 358│ A. D. Wright, et al, Mar. Drugs, 2012, 10, 1619

O O

O

182 Eunicidiol Type: Lobane diterpenoids. C20H32O2 Source: Gorgonian Eunicea fusca (Hillsboro Ledge, Florida). Pharm: Anti-inflammatory (potent). Ref: D. H. Marchbank, et al, JNP, 2012, 75, 1289

HO H

OH

183 Fuscol 8,10,13(15),16-Lobatetraen-18-ol Type: Lobane diterpenoids. C20H32O Colorless oil, [α]D29 = +14° (c = 0.099, CHCl3), [α]D = +17.6° (c = 0.9, CHCl3). Source: Gorgonian Eunicea fusca (Santa Marta Bay, Caribbean Sea, Colombia), soft coral Lobophytum pauciflorum (Taketomijima I., Okinawa). Pharm: Anti-inflammatory (TPA-induced

68

3 Diterpenoids

mouse ear edema, 0.5mg/ear, InRt = 27.3%, control Indomethacin, InRt = 77.3%), cytotoxic (A431 hmn epidermic cancer cells, IC50 = 0.52 μmol/L). Ref: Y. Gopichand, et al, Tetrahedron Lett. 1978, 39, 3641│ J. Shin, et al, JOC, 1991, 56, 3153│ H. Kosugi, et al, JCS Perkin I, 1998, 217│ E. Reina, et al, BoMCL, 2011, 21, 5888│ S. V. S. Govindam, et al, BoMC, 2012, 20, 687

13

15

H

OH

184 Fuscol methyl ether Type: Lobane diterpenoids. C21H34O Oil, [α]D = −2.6° (c = 0.33, CHCl3), [α]D25 = +14.9° (c = 0.9, CHCl3). Source: Gorgonian Eunicea fusca, soft coral Lobophytum pauciflorum. Pharm: Antifungal (phytopathogenic fungus Cladosporium cucumerinum). Ref: A. S. R. Anjaneyulu, et al, Indian J. Chem., Sect. B, 1995, 34, 1074│ R. A. Endrada, et al, JNP, 1998, 61, 358

O

185 Fuscoside B Type: Lobane diterpenoids. C25H40O5 Oil, [α]D = −90° (c = 1, CHCl3). Source: Gorgonian Eunicea fusca(Caribbean Sea). Pharm: Anti-inflammatory (mouse peritoneal macrophage, selectively inhibits synthesis of leukotrienes LTB4 and LTC4, but not PGE2). Ref: Y. Gopichand, et al, Tet. Lett., 1978, 3641│ J. Shin, et al, JOC, 1991, 56, 3153

H

O HO HO

O

OH

186 Fuscoside C 13ξ,15ξ-Epoxy (isomer 1)-8,10,13(15),16-lobatetraen-18-ol O-β-D-arabinopyranose Type: Lobane diterpenoids. C25H40O6 Source: Gorgonian Eunicea fusca (Caribbean Sea). Pharm: Anti-inflammatory. Ref: J. H. Shin, et al, JOC. 1991, 56, 3153│ B. L. Raju, et al, Indian J. Chem., Sect. B, 1995, 34, 221

3.33 Lobane Diterpenoids

69

O R

H

R

OO HO

isomer 1

HO

OH

187 Fuscoside D 13ξ,15ξ-Epoxy (isomer 2)-8,10,13(15),16-lobatetraen-18-ol O-β-D-arabinopyranose Type: Lobane diterpenoids. C25H40O6 Source: Gorgonian Eunicea fusca. Pharm: Antiinflammatory. Ref: J. H. Shin, et al, Eunicea fusca. JOC, 1991, 56, 3153│ B. L. Raju, et al, Indian J. Chem., Sect. B, 1995, 34, 221

O R

H

R

OO HO

isomer 2

HO OH

188 Ineleganene 8,10,13(15)E,18-Lobatetraene Type: Lobane diterpenoids. C20H32 Oil, [α]D25 = +9.6° (c = 0.1, CHCl3). Source: Soft coral Sinularia inelegans (Taiwan waters). Pharm: Cytotoxic (A549, GI50 = 3.63 μg/mL; P388, GI50 = 0.20 μg/mL). Ref: M. -C. Chai, et al, JNP, 2000, 63, 843

13

15

189 (1R*,2R*,4S*,15E)-Loba-8,10,13(14),15(16)-tetraen-17,18-diol-17-acetate Type: Lobane diterpenoids. C21H32O3 Colourless oil, [α]D24 = −9.5° (c = 0.23, MeOH). Source: Soft coral Sinularia sp. (Bowden Reef, Great Barrier Reef, Australia). Pharm: Cytotoxic (SF268, GI50 = 15 μmol/L, MCF7 breast-pleural effusion adenocarcinoma cells, GI50 = 8.8 μmol/L, H460 Lung large cell carcinoma cells, GI50 = 11.5 μmol/L). Ref: A. D. Wright, et al, Mar. Drugs, 2012, 10, 1619

70

3 Diterpenoids

OH O H

O

H

190 Lobatriene 14,17-Epoxy-8,10,13(15)-lobatrien-18-ol Type: Lobane diterpenoids. C20H32O2 Colorless viscous oil, [α]D26 = +85.5° (c = 0.098, CHCl3), [α]D25 = +86.7° (c = 0.19, CHCl3). Source: Soft corals Lobophytum pauciflorum (Taketomijima I., Okinawa) and Lobophytum sp. Pharm: Cytotoxic (A431 hmn epidermic cancer cells, IC50 = 0.41 μmol/L); toxic (brine shrimp). Ref: R. W. Dunlop, et al, Aust. J. Chem., 1979, 32, 1345│ T. Kusumi, et al, JOC, 1992, 57, 1033│ V. Anjaneyulu, et al, Indian J. Chem., Sect. B, 1993, 32B, 1198│ S. V. S. Govindam, et al, BoMC, 2012, 20, 687

O

OH

191 Loba-8,10,13(15)-triene-17-acetoxy-18-ol Type: Lobane diterpenoids. C22H36O3 Yellow viscous oil, [α]D = +52.7° (c = 1.56, CHCl3). Source: Soft coral Lobophytum pauciflorum. Pharm: Antifungal (phytopathogenic fungus Cladosporium cucumerinum). Ref: R. A. Endrada, et al, JNP, 1998, 61, 358 O O OH

192 (17R)-Loba-8,10,13(15)-triene-17,18-diol Type: Lobane diterpenoids. C20H34O2 Cryst. (EtOAc), mp 195.3–197.1 °C, [α]D25 = +25.9° (c = 0.34, CHCl3). Source: Soft coral Lobophytum sp. (Great Barrier Reef). Pharm: Anticonvulsant and antiepileptic agent. Ref: R. W. Dunlop, et al, Aust. J. Chem., 1979, 32, 1345│ M. Iwashima, et al, Tet. Lett., 1992, 33, 81│ H. Nagaoka, et al, CPB, 1992, 40, 556

OH OH

3.34 Pachydictyane Diterpenoids

71

193 Loba-8,10,13(15)-triene-16,17,18-triol 8,10,13(15)-Lobatriene-16,17,18-triol Type: Lobane diterpenoids. C20H34O3 Cryst. or colourless oil, mp 73–75 °C, [α]D = −14.1° (c = 1, CHCl3). Source: Soft corals Sinularia sp. (Bowden Reef, Great Barrier Reef), Lobophytum sp. (India waters) and Lobophytum hirsutum. Pharm: Cytotoxic (SF268, GI50 = 18.5 μmol/L, breast-pleural effusion adenocarcinoma cells, GI50 = 17 μmol/L, lung large cell carcinoma cells, GI50 = 13 μmol/L). Ref: B. L. Raju, et al, JNP, 1993, 56, 961│ B. L. Raju, et al, Indian J. Chem., Sect. B, 1994, 33, 1033; 1995, 34, 221│ A. D. Wright, et al, Mar. Drugs, 2012, 10, 1619

OH

OH

OH

194 Lobatrienolide 18-Hydroxy-8,10,13(15)-lobatrien-14,17-olide Type: Lobane diterpenoids. C20H30O3 Colourless oil, [α]D25 = +89.3° (c = 0.63, CHCl3). Source: Soft corals Sinularia sp. (Bowden Reef, Great Barrier Reef) and Sinularia flexibilis (Okinawa). Pharm: Cytotoxic (SF268, GI50 = 7.4 μmol/L, breast-pleural effusion adenocarcinoma cells, GI50 = 17 μmol/L, lung large cell carcinoma cells, GI50 = 18 μmol/L). Ref: T. Hamada, et al, Chem. Lett., 1992, 33│ M. Kato, et al, J. Chem. Soc., Perkin Trans. I, 1999, 783│ A. D. Wright, et al, Mar. Drugs, 2012, 10, 1619

O

O

OH

3.34 Pachydictyane Diterpenoids 195 Acutilol A (5β,6β,11R,14ξ )-14,15-Epoxy-1(10),3-pachydictyadien-6-ol Type: Pachydictyane diterpenoids. C20H32O2 [α]D25 = +29.8° (c = 1.5, CH2Cl2). Source: Brown alga Dictyota acutiloba (Hawaii). Pharm: Antifeedant (marine herbivore, urchins, fishes). Ref: I. H. Hardt, et al, Phytochemistry, 1996, 43, 71

72

3 Diterpenoids

H HO

O H

196 Acutilol A acetate Type: Pachydictyane diterpenoids. C22H34O3 [α]D25 = +29.6° (c = 1.5, CH2Cl2). Source: Brown alga Dictyota acutiloba (Hawaii). Pharm: Antifeedant (marine herbivore, urchins, fishes). Ref: I. H. Hardt, et al, Phytochemistry, 1996, 43, 71

H O

O H O

197 Acutilol B (5β,6β,11R)-6-Hydroxy-1(10),3-pachydictyadien-14-one Type: Pachydictyane diterpenoids. C20H32O2 [α]D25 = −28° (c = 2.0, CH2Cl2). Source: Brown alga Dictyota acutiloba (Hawaii). Pharm: Antifeedant (marine herbivore, urchins, fishes). Ref: I. H. Hardt, et al, Phytochemistry, 1996, 43, 71

O

H HO

H

198 Dictyol C Type: Pachydictyane diterpenoids. C20H34O2 Crystal (hexane), mp 68 °C, [α]D = −16.6° (c = 1, CHCl3). Source: Brown algae Dictyota dentata (Barbados), Dictyota dichotoma (Mediterranean Sea) and Dilophus dichotoma, sea hare Aplysia depilans. Pharm: Antimicrobial; algicide; antimitotic, ichthyotoxin. Ref: B. Danise, et al, Experientia, 1977, 33, 413│ D. J. Faulkner, et al, Phytochemistry, 1977, 16, 991│ V. Amico, et al, Tetrahedron, 1980, 36, 1409│ M. Ishitsuka, et al, Chem. Lett., 1982, 1517│ A. B. Alvarado, et al, JNP, 1985, 48. 132

3.34 Pachydictyane Diterpenoids

73

OH H 10

H

H

OH

199 Dictyol F (1α,5β,6β,11R,14R)-3,10(18),15-Pachydictyatriene-6,14-diol Type: Pachydictyane diterpenoids. C20H32O2 Oil, [α]D25 = +48.2° (c = 1.5, CHCl3). Source: Brown alga Dictyota dichotoma. Pharm: Antimicrobial. Ref: N. Enoki, et al, Chem. Lott., 1983, 1627 H

OH 6

H

OH

14

H

200 Epidictyol F Type: Pachydictyane diterpenoids. C20H32O2 Cryst., mp 62–63 °C, [α]D25 = +37.5° (c = 1.1, CHCl3). Source: Brown alga Dictyota dichotoma, sea hare Aplysia depilans. Pharm: Antimicrobial. Ref: N. Enoki, et al, Chem. Lett., 1983, 1627 H OH H OH

14

H

201 Isopachydictyol A Type: Pachydictyane diterpenoids. C20H32O [α]D25 = −25.7° (c = 0.28, CHCl3). Source: Brown alga Dictyota dichotoma (Cádiz, Spain). Pharm: Cytotoxic (P388, ED50 = 5 μg/mL, A549, ED50 = 5 μg/mL, HT29, ED50 = 5 μg/mL, MEL28, ED50 = 5 μg/mL). Ref: R. Durán, et al, Tetrahedron, 1997, 53, 8675 H

H H

HO

74

3 Diterpenoids

202 Pachydictyol A Type: Pachydictyane diterpenoids. C20H32O Oil, [α]D20 = +106° (cyclohexane). Source: Brown algae Dictyota dentata (Barbados), Dictyota dichotoma (Abu-Bakr, Red Sea, Egypt) (Wafa, 2013), Dictyota binghamiae (British Columbia), Dictyota dichotoma (Australia) and Pachydictyon coriaceum, sea hares Aplysia depilans and Aplysia vaccaria. Pharm: Antifeedant, algicide, antimitotic, ichthyotoxic, vasopressin-V1 receptor antagonist, norepinephrine antagonist. Ref: D. R. Hirschfeld, et al, JACS, 1973, 95, 4049│ L. Minale, et al, Tet. Lett., 1976, 17, 2711│ D. J. Faulkner, Tetrahedron, 1977, 33, 1421│ J. F. Blount, et al, Aust. J. Chem., 1982, 35, 145│ C. Pathirana, et al, Can. J. Chem., 1984, 62. 1666│ Abou-El-Wafa, et al, Mar. Drugs, 2013, 11, 3109 H H

H OH

3.35 Cneorubine Diterpenoids 203 Emmottene (1β,4α,5β,6α,7β)-10(14),17-Cneorubadiene Type: Cneorubine diterpenoids. C20H32 Oil. Source: Gorgonian Briareum polyanthes. Pharm: Toxic (threshold brine shrimp, 24 h, LD50 = 1000 ppm). Ref: J. M. Cronan Jr., et al, JOC, 1995, 60, 6864 H 1 7

H H

H

3.36 Serrulatane and Biflorane Diterpenoids 204 4,9,15-Bifloratriene Type: Serrulatane and biflorane diterpenoids. C20H32 Oil, [α]D = +64° (c = 0.05, CHCl3); [α]D20 = +51.4° (c = 0.5, CHCl3). Source: Sponges Acanthella cavernosa (Japan waters) and Cribrochalina sp. (Caribbean Sea). Pharm: Antifoulant (inhibits settlement and metamorphosis of barnacle larvae). Ref: H. Hirota, et al, Tetrahedron, 1996, 52, 2359│ M. L. Ciavatta, et al, Tetrahedron, 1999, 55, 12629

3.36 Serrulatane and Biflorane Diterpenoids

75

H

H

205 5,10-Biisothiocyanatokalihinol G Type: Serrulatane and biflorane diterpenoids. C23H33N3O2S3 [α]D = −62.7° (c = 0.8, CHCl3). Source: Sponge Acanthella sp. (Okinawa). Pharm: Antiplasmodial (Plasmodium falciparum, EC50 = 2.6 × 10–6 mol/L, FM3C, EC50 = 7.0 × 10−7 mol/L). Ref: H. Miyaoka, et al, Tetrahedron, 1998, 54, 13467 NCS

H H

HO H NCS

O

NCS

206 Cavernene A Type: Serrulatane and biflorane diterpenoids. C21H33NO Colorless oil, [α]D20 = +25.0° (c = 0.06, MeOH). Source: Sponge Acanthella cavernosa (Xisha Is., South China Sea, China). Pharm: Cytotoxic (HCT116, IC50 = 6.31 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 > 50 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa, IC50 > 50 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 > 50 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 > 50 μmol/L, Camptothecin, IC50 = 0.50 μmol/L). Ref: Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 H N

H

O H

H H

207 Cavernene B Type: Serrulatane and biflorane diterpenoids. C21H35NO Colorless oil, [α]D20 = +46.2° (c = 0.07, MeOH). Source: Sponge Acanthella cavernosa (Xisha Is., South China Sea, China). Pharm: Cytotoxic (HCT116, IC50 = 8.99 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 > 50 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa,

76

3 Diterpenoids

IC50 > 50 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 > 50 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 > 50 μmol/L, Camptothecin, IC50 = 0.50 μmol/L). Ref: Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 H N

H

O H

H H

208 Cavernene C Type: Serrulatane and biflorane diterpenoids. C21H35NO White needles (MeOH), mp 98.0–102.0 °C, [α]D20 = +20.0° (c = 0.03, MeOH). Source: Sponge Acanthella cavernosa (Xisha Is., South China Sea, China). Pharm: Cytotoxic (HCT116, A549, HeLa, QGY-7701 and MDA-MB-231, all IC50s > 50 μmol/L). Ref: Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 H N

H

O H

H H

209 Cavernene D Type: Serrulatane and biflorane diterpenoids. C21H33NO2 Colorless needles (MeOH), mp 112.0–115.0 °C, [α]D20 = +51.4° (c = 0.04, MeOH). Source: Sponge Acanthella cavernosa (Xisha Is., South China Sea, China). Pharm: Cytotoxic (HCT116, A549, HeLa, QGY-7701 and MDA-MB-231, all IC50s > 50 μmol/L). Ref: Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 H N

H

O H

H H

210 Elisabethamine Type: Serrulatane and biflorane diterpenoids. C21H33NO2 Yellow gum, [α]D20 = +89.0°. Source: Gorgonian Pseudopterogorgia elisabethae (Florida Keys). Pharm: Cytotoxic (MTT assay, LNCaP, IC50 = 10.35 μg/mL, Calu, 20 μg/mL). Ref: A. Ata, et al, Tet. Lett., 2000, 41, 5821

3.36 Serrulatane and Biflorane Diterpenoids

OH

H

77

H N

OH

211 10-Formamido-5-isocyanatokalihinol A Type: Serrulatane and biflorane diterpenoids. C22H35ClN2O4 [α]D = −25° (c = 0.02, CHCl3). Source: Sponge Acanthella cavernosa (Japan waters). Pharm: Antifoulant (inhibits settlement and metamorphosis of barnacle larvae). Ref: H. Hirota, et al, Tetrahedron, 1996, 52, 2359 O NH

H

10

H 2

1

5

H

H O

4

OH

N O

14

Cl

212 10-Formamido-5-isothiocyanatokalihinol A Type: Serrulatane and biflorane diterpenoids. C22H35ClN2O3S [α]D = +24° (c = 0.05, CHCl3). Source: Sponge Acanthella cavernosa (Japan waters). Pharm: Antifoulant (inhibits settlement and metamorphosis of barnacle larvae). Ref: H. Hirota, et al, Tetrahedron, 1996, 52, 2359 O NH

H

10

H

1

2 5

H

H O 14

Cl

4

NCS

OH

78

3 Diterpenoids

213 15-Formamidokalihinene Type: Serrulatane and biflorane diterpenoids. C22H34N2O2 Source: Sponges Acanthella cavernosa (Xisha Is., South China Sea, China) and Acanthella cavernosa. Pharm: Cytotoxic (HCT116, IC50 > 50 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 = 17.53 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa, IC50 = 14.74 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 = 16.39 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 > 50 μmol/L, Camptothecin, IC50 = 0.50 μmol/L). Ref: J. Rodriguez, et al, Tetrahedron 1994, 50, 11079│ Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 NC

H H H O O H

N H

214 10-Formamidokalihinene Type: Serrulatane and biflorane diterpenoids. C23H34N2O2 Source: Sponges Acanthella cavernosa (Xisha Is., South China Sea, China) and Acanthella cavernosa. Pharm: Cytotoxic (HCT116, IC50 > 50 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 = 6.98 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa, IC50 = 13.30 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 = 14.53 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 = 6.84 μmol/L, Camptothecin, IC50 = 0.50 μmol/L). Ref: J. Rodriguez, et al, Tetrahedron 1994, 50, 11079│ Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 O H

HN H

H O

CN

H

3.36 Serrulatane and Biflorane Diterpenoids

79

215 10-Formamidokalihinol A Type: Serrulatane and biflorane diterpenoids. C22H35ClN2O3 [α]D = +11.0° (c = 0.15, CHCl3). Source: Sponge Acanthella cavernosa (Japan waters). Pharm: Antifoulant (inhibits settlement and metamorphosis of barnacle larvae). Ref: H. Hirota, et al, Tetrahedron, 1996, 52, 2359 O NH

H

10

H 2

1

5

H

H O

4

OH

NC

14

Cl

216 10-Formamidokalihinol E Type: Serrulatane and biflorane diterpenoids. C22H35ClN2O3 [α]D = −2.8° (c = 0.15, CHCl3). Source: Sponge Acanthella cavernosa (Japan waters). Pharm: Antifoulant (inhibits settlement and metamorphosis of barnacle larvae). Ref: H. Hirota, et al, Tetrahedron, 1996, 52, 2359 O NH

H

10

H 2

1

5

H

H O

4

OH

NC

14

Cl

217 6-Hydroxykalihinene Type: Serrulatane and biflorane diterpenoids. C22H32N2O2 Needles (EtOH). Source: Sponges Acanthella sp. (Okinawa) and Acanthella cavernosa (Fiji). Pharm: Antiplasmodial (Plasmodium falciparum, EC50 = 8.0 × 10–8 mol/L, FM3C, EC50 = 1.2 × 10−6 mol/L, SI = 15). Ref: J. Rodriguez, et al, Tetrahderon, 1994, 50, 11079│ H. Miyaoka, et al, Tetrahedron, 1998, 54, 13467

80

3 Diterpenoids

NC

H

2

10 5

OH

H O 15

CN

218 10-Isothiocyanatobiflora-4,15-diene Type: Serrulatane and biflorane diterpenoids. C21H33NS Oil, [α]D = +97° (c = 0.085, CHCl3), [α]D25 = +45° (c = 0.26, CHCl3). Source: Sponge Cymbastela hooperi (Great Barrier Reef), an un identified sponge (family Adocidae, Japan). Pharm: Antiplasmodial (Plasmodium falciparum D6, IC50 > 10000 ng/mL; W2, IC50 > 10000 ng/mL); cytotoxic (KB, IC50 > 20000 ng/mL). Ref: H. A. Sharma, et al, Tet. Lett., 1992, 33, 1593│ G. M. König, et al, JOC, 1996, 61, 3259

H H H

NCS

219 10-Isothiocyanatokalihinol C Type: Serrulatane and biflorane diterpenoids. C22H32N2O2S [α]D20 = −11° (c = 0.06, CHCl3). Source: Sponge Phakellia pulcherrima (Philippines). Pharm: Antibiotic. Ref: D. Wolf, et al, JNP, 1998, 61, 1524 NCS

H HO

H NC

H O

220 Kalihinene Type: Serrulatane and biflorane diterpenoids. C22H32N2O Cryst. (EtOH), [α]D25 = +16° (c = 0.13, CHCl3). Source: Sponges Acanthella sp. (Okinawa), Acanthella klethra and

3.36 Serrulatane and Biflorane Diterpenoids

81

Acanthella cavernosa. Pharm: Antiplasmodial (Plasmodium falciparum, EC50 = 1.0 × 10–8 mol/L, FM3C, EC50 = 3.7 × 10–8 mol/L, SI = 4); antifungal (Mortierella romannicus and Penicillium chrysogenum); cytotoxic (P388, IC50 = 1.2 μg/mL). Ref: N. Fusetani, et al, Tet. Lett., 1990, 31, 3599│ H. Miyaoka, et al, Tetrahedron, 1998, 54, 13467 NC

H

2

10 5

H

H O 15

NC

221 Kalihinene E Type: Serrulatane and biflorane diterpenoids. C21H34ClNO2 Colorless needles (MeOH), mp 185.0–190.0 °C, [α]D20 = +25.0° (c = 0.04, MeOH). Source: Sponge Acanthella cavernosa (Xisha Is., South China Sea, China). Pharm: Cytotoxic (HCT116, IC50 = 14.36 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 > 50 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa, IC50 = 13.36 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 = 17.78 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 = 12.84 μmol/L, Camptothecin, IC50 = 0.50 μmol/L). Ref: Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 H N

H

O H

H H O

Cl

222 Kalihinene F Type: Serrulatane and biflorane diterpenoids. C21H33NO2 Colorless oil, [α]D20 = +2.5° (c = 0.08, MeOH). Source: Sponge Acanthella cavernosa (Xisha Is., South China Sea, China). Pharm: Cytotoxic (HCT116, A549, HeLa, QGY-7701 and MDA-MB-231, all IC50s > 50 μmol/L). Ref: Y. Xu, et al, Mar. Drugs, 2012, 10, 1445

82

3 Diterpenoids

H H H O O N H

223 Kalihinene X Type: Serrulatane and biflorane diterpenoids. C21H34ClNO2 [α]D23 = +26.7° (c = 0.3, CHCl3). Source: Sponges Acanthella cavernosa (Xisha Is., South China Sea, China) and Acanthella cavernosa (Japan waters). Pharm: Cytotoxic (HCT116, IC50 = 12.25 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 = 8.55 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa, IC50 = 10.59 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 = 13.02 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 = 7.46 μmol/L, Camptothecin, IC50 = 0.50 μmol/L); antifoulant (inhibits cyprid larval settlement and metamorphosis of barnacle Balanus amphitrite, EC50 = 0.49 μg/mL). Ref: T. Okino, et al, Tedrahedron Lett. 1995, 36, 8637│ Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 H N

H

O H

H H O

Cl

224 Kalihinene Y Type: Serrulatane and biflorane diterpenoids. C21H34ClNO2 [α]D23 = +11° (c = 0.01, CHCl3). Source: Sponges Acanthella cavernosa (Xisha Is., South China Sea, China) and Acanthella cavernosa (Japan waters). Pharm: Cytotoxic (HCT116, IC50 > 50 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 = 17.12 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa, IC50 = 10.05 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 = 14.41 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 = 15.23 μmol/L, Camptothecin, IC50 = 0.50 μmol/L); antifoulant (inhibits cyprid larval settlement and metamorphosis of barnacle Balanus amphitrite, EC50 = 0.45 μg/mL). Ref: T. Okino, et al, Tedrahedron Lett. 1995, 36, 8637│ Y. Xu, et al, Mar. Drugs, 2012, 10, 1445

3.36 Serrulatane and Biflorane Diterpenoids

H N

H

83

O H

H H O

Cl

225 Kalihinene Z Type: Serrulatane and biflorane diterpenoids. C21H34ClNO2 [α]D23 = +11.7° (c = 0.035, CHCl3). Source: Sponge Acanthella cavernosa (Japan waters). Pharm: Antifoulant (inhibits cyprid larval settlement and metamorphosis of barnacle Balanus amphitrite, EC50 = 1.1 μg/mL). Ref: T. Okino, et al, Tet. Lett., 1995, 36, 8637 H N

H 1

O

H

H O 14

Cl

226 Kalihinol A Type: Serrulatane and biflorane diterpenoids. C22H33ClN2O2 Plates (hexane), mp 233 °C, [α]D = +16° (c = 1, CHCl3). Source: Sponges Acanthella sp. (Yalong Bay, Hainan I., China), Acanthella sp. (Okinawa) and Acanthella spp. (Guam). Pharm: Antiplasmodial (Plasmodium falciparum, EC50 = 1.2 × 10–9 mol/L, FM3C, EC50 = 3.8 × 10–7 mol/L, SI = 317); antibacterial (Bacillus subtilis and Staphylococcus aureus); antifungal (Candida albicans); antihelmintic (high activity against rodentpathogenic roundworm Nippostongylus brasiliensis) (Omar, 1988); antifoulant (inhibits cyprid larval settlement and metamorphosis of barnacle Balanus amphitrite, EC50 = 0.087 μg/mL). Ref: C. W. J. Chang, et al, JACS, 1984, 106, 4644; 1987, 109, 6119│ S. Omar, et al, JOC, 1988, 53, 5971│ T. Okino, et al, Tet. Lett., 1995, 36, 8637│ H. Hirota, et al, Tetrahedron, 1996, 52, 2359│ H. Miyaoka, et al, Tetrahedron, 1998, 54, 13467│ S. Shimomura, et al, Tet. Lett., 1999, 40, 8015│ J. -Z. Sun, et al, Arch. Pharm. Res., 2009, 32, 1581

84

3 Diterpenoids

NC H 10

2

H

OH

5

H O

NC

14

Cl

227 Kalihinol D Type: Serrulatane and biflorane diterpenoids. C22H33ClN2O2 Plates (heptane/ Me2CO), mp 183–184 °C, [α]D = +8° (c = 1.5, CHCl3). Source: Sponges Acanthella sp. (Yalong Bay, Hainan I., China) and Acanthella spp. Pharm: Cytotoxic (A549, IC50 = 3.17 μg/mL). Ref: C. W. J. Chang, et al, JACS, 1987, 109, 6119│ J. -Z. Sun, et al, Arch. Pharm. Res., 2009, 32, 1581 H

NC

HO Cl

O

H

NC

228 Kalihinol E Type: Serrulatane and biflorane diterpenoids. C22H33ClN2O2 Sol. MeOH, CHCl3; poorly sol. H2O. Source: Sponges Acanthella spp. Pharm: Antifoulant (inhibits cyprid larval settlement and metamorphosis of barnacle Balanus amphitrite, EC50 < 0.5 μg/mL). Ref: A. Patra, et al, JACS, 1984, 106, 7981│ C. W. J. Zhang, et al, JACS, 1987, 109, 6119│ T. Okino, et al, Tet. Lett., 1995, 36, 8637│ H. Hirota, et al, Tetrahedron, 1996, 52, 2359 NC

H H

HO NC

H O

Cl

3.36 Serrulatane and Biflorane Diterpenoids

85

229 Kalihinol F Type: Serrulatane and biflorane diterpenoids. C23H33N3O2 Crystal (hexane/Me2CO), mp 176–178 °C, [α]D = +8° (c = 1, CHCl3). Source: Sponges Acanthella spp. Pharm: Topoisomerase I inhibitor; antimicrobial (Bacillus subtilis, Staphylococcus aureus and Candida albicans). Ref: A. Patra, et al, JACS, 1984, 106, 7981│ C. W. J. Zhang, et al, JACS, 1987, 109, 6119 NC

H HO

H NC

H O NC

230 10-epi-kalihinol I Type: Serrulatane and biflorane diterpenoids. C22H33ClN2O2S2 Cryst., mp 209–210 °C, [α]D = −52.4° (c = 0.3, CHCl3). Source: Sponge Acanthella sp. (Okinawa). Pharm: Antiplasmodial (Plasmodium falciparum, EC50 > 1.8 × 10–6 mol/L (InRt = 38%)). Ref: H. Miyaoka, et al, Tetrahedron, 1998, 54, 13467 SCN

H 10

OH H

H

NCS

O

Cl

231 Kalihinol J Type: Serrulatane and biflorane diterpenoids. C22H35ClN2O3S [α]D25 = +24° (c = 0.03, CHCl3). Source: Sponge Acanthella cavernosa (Thailand). Pharm: Anthelmintic. Ref: K. A. Alvi, et al, JNP, 1991, 54, 71

86

3 Diterpenoids

SCN

H OH H

H

HN

O

O

Cl

232 Kalihinol X Type: Serrulatane and biflorane diterpenoids. C22H33ClN2O2S Needles (hexane), mp 199–200 °C, [α]D25 = −30° (c = 0.09, CHCl3). Source: Sponges Acanthella spp. Pharm: Folate biosynthesis inhibitor of bacteria; antihelmintic (high activity against rodentpathogenic roundworm Nippostongylus brasiliensis) (Omar, 1988). Ref: C. W. J. Chang, et al, JACS, 1987, 109, 6119│ S. Omar, et al, JOC, 1988, 53, 5971│ K. A. Alvi, et al, JNP, 1991, 54, 71 SCN

H OH H

H

NC

O

Cl

233 10-epi-Kalihinol X Type: Serrulatane and biflorane diterpenoids. C22H33ClN2O2S Colorless oil, [α]D20 = +15° (c = 0.15, CHCl3). Source: Sponge Acanthella sp. (Yalong Bay, Hainan I., China). Pharm: Cytotoxic (A549, IC50 = 9.30 μg/mL). Ref: J. -Z. Sun, et al, Arch. Pharm. Res., 2009, 32, 1581 H HO

NCS H

NC

H

O Cl

3.36 Serrulatane and Biflorane Diterpenoids

87

234 Kalihinol Y Type: Serrulatane and biflorane diterpenoids. C21H32ClNO2 Needles (hexane/EtOAc), mp 176–179 °C, [α]D = −34° (c = 1, CHCl3). Source: Sponges Acanthella cavernosa (Thailand) and Acanthella spp. Pharm: Folate biosynthesis inhibitor of bacteria; antihelmintic (high activity against rodent-pathogenic roundworm Nippostongylus brasiliensis) (Omar, 1988). Ref: C. W. J. Chang, et al, JACS, 1987, 109, 6119│ S. Omar, et al, JOC, 1988, 53, 5971│ K. A. Alvi, et al, JNP, 1991, 54, 71 H OH H

H

NC

O

Cl

235 Δ9-Kalihinol Y Type: Serrulatane and biflorane diterpenoids. C21H32ClNO2 Needles, mp 188–190 °C, [α]D = +38.4° (c = 0.24, CHCl3), [α]D20 = +9° (c = 0.05, CHCl3). Source: Sponges Acanthella sp. and Phakellia pulcherrima. Pharm: Antimalarial; antihelmintic (high activity against rodent-pathogenic roundworm Nippostongylus brasiliensis) (Omar, 1988). Ref: S. Omar, et al, JOC, 1988, 53, 5971│ D. Wolf, et al, JNP, 1998, 61, 1524│ H. Miyaoka, et al, Tetrahedron, 1998, 54, 13467 H 9

H

HO NC

H O

Cl

236 Kalihipyran A Type: Serrulatane and biflorane diterpenoids. C21H31NO2 Oil, [α]D23 = +38.6° (c = 0.08, CHCl3). Source: Sponges Acanthella cavernosa (Xisha Is., South China Sea, China) and Acanthella cavernosa. Pharm: Antifoulant; cytotoxic (HCT116, IC50 > 50 μmol/L, control Camptothecin, IC50 = 9.25 μmol/L; A549, IC50 = 13.09 μmol/L, Camptothecin, IC50 = 2.32 μmol/L; HeLa, IC50 = 11.19 μmol/L, Camptothecin, IC50 = 6.98 μmol/L; QGY-7701, IC50 = 13.53 μmol/L, Camptothecin, IC50 = 4.05 μmol/L; MDA-MB-231, IC50 > 50 μmol/L, Camptothecin, IC50 = 0.50 μmol/L). Ref: T. Okino, et al, JNP, 1996, 59, 1081│ Y. Xu, et al, Mar. Drugs, 2012, 10, 1445

88

3 Diterpenoids

H N

H

O H

H H O

237 Kalihipyran B Type: Serrulatane and biflorane diterpenoids. C21H32ClNO2 Oil, [α]D23 = +73.4° (c = 0.035, CHCl3). Source: Sponge Acanthella cavernosa. Pharm: Antifoulant. Ref: T. Okino, et al, JNP, 1996, 59, 1081 H N

H

H H

H O

Cl

238 Kalihipyran C Type: Serrulatane and biflorane diterpenoids. C21H31NO2 Colorless oil, [α]D20 = +24.6° (c = 0.07, MeOH). Source: Sponge Acanthella cavernosa (Xisha Is., South China Sea, China). Pharm: Cytotoxic (HCT116, A549, HeLa, QGY-7701 and MDA-MB-231, all IC50s > 50 μmol/L). Ref: Y. Xu, et al, Mar. Drugs, 2012, 10, 1445 H N

H

H H

H O

O

3.36 Serrulatane and Biflorane Diterpenoids

89

239 Lemnabourside B Type: Serrulatane and biflorane diterpenoids. C28H44O7 mp 66.5–67.5 °C, [α]D25 = +10.3° (c = 0.029, EtOH). Source: Soft coral Lemnalia bournei (South China Sea). Pharm: Cytotoxic (HepA, IC50 = 33.5 μg/mL, S180A, IC50 = 40.0 μg/mL, EAC, IC50 = 73.3 μg/mL). Ref: M. Zhang, et al, JNP, 1998, 61, 1300 H

H

H

OH

O

O O

O

O OH

240 Lemnabourside C Type: Serrulatane and biflorane diterpenoids. C28H44O7 mp 69.0–70.2 °C, [α]D22.5 = +25.0° (c = 0.020, EtOH). Source: Soft coral Lemnalia bournei (South China Sea). Pharm: Cytotoxic (HepA, IC50 = 41.4 μg/mL, S180A, IC50 = 186.9 μg/mL, EAC, IC50 = 40.5 μg/mL). Ref: M. Zhang, et al, JNP, 1998, 61, 1300 H

H

H

OH

O

O

O

OH O

241 Secopseudopterosin H 7,8-Dihydroxyeriogorgiaene 7-O-(4-O-acetyl-α-D-arabinopyranoside) Type: Serrulatane and biflorane diterpenoids. C27H40O7 Powder, [α]D25 = −142.3° (c = 0.8, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA (phorbol 12-myristate 13-acetate): O2•−, IC50 > 10 μmol/L; TXB2, IC50 > 10 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 3.6 μmol/L). Ref: I. I. Rodriguez, et al, JNP, 2004, 67, 1672

H

O

OH HO

O O

7

O

ADARABP

OH

90

3 Diterpenoids

242 Secopseudopterosin I 7,8-Dihydroxyeriogorgiaene 7-O-(2-O-acetyl-α-D-arabinopyranoside) Type: Serrulatane and biflorane diterpenoids. C27H40O7 Powder, [α]D25 = −92.4° (c = 2.1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Anti-inflammatory (release effect on rat microglia stimulated by 1 μmol/L PMA (phorbol 12-myristate 13-acetate): O2•−, IC50 > 10 μmol/L; TXB2, IC50 > 10 μmol/L; LDH (Lactate dehydrogenase), LDH50 = 10 μmol/L). Ref: I. I. Rodriguez, et al, JNP, 2004, 67, 1672

O O OH

OH

H

O 7

O

ADARABP

OH

243 Secopseudopteroxazole Type: Serrulatane and biflorane diterpenoids. C21H29NO Yellowish oil, [α]D25= +28.2° (c = 0.85, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae (Columbia). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 66%). Ref: A. D. Rodriguez, et al, Org. Lett., 1999, 1, 527 O N

H

244 (1α,4αH )-14-Serrulatene Erogorgiaene Type: Serrulatane and biflorane diterpenoids. C20H30 Oil, [α]D25 = +24.4° (c = 3.2, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antibacterial (antimycobacterial). Ref: A. D. Rodriguez, et al, JNP, 2001, 64, 100

H

3.37 Sacculatane Diterpenoids

91

245 14-Serrulaten-7-ol Type: Serrulatane and biflorane diterpenoids. C20H30O Oil, [α]D25 = +25.8° (c = 3.8, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae. Pharm: Antibacterial (antimycobacterial). Ref: A. D. Rodriguez, et al, JNP, 2001, 64, 100

OH H

3.37 Sacculatane Diterpenoids 246 Durbinal A Type: Sacculatane diterpenoids. C25H38O4 Oil, [α]D = +5.6° (c = 2.5, CHCl3). Source: Sponge Psammoclema sp. (Sodwana Bay, Durban, South Africa). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL). Ref: A. Rubi, et al, Tet. Lett., 1995, 36, 4853

H

O

O

O

O

247 Durbinal B Type: Sacculatane diterpenoids. C23H36O3 Oil, [α]D = −12.5° (c = 1.4, CHCl3). Source: Sponge Psammoclema sp. (Sodwana Bay, Durban, South Africa). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL). Ref: A. Rubi, et al, Tet. Lett., 1995, 36, 4853

H

OH

O

O

92

3 Diterpenoids

248 Durbinal C Type: Sacculatane diterpenoids. C22H34O2 Oil, [α]D = −14.5° (c = 0.9, CHCl3). Source: Sponge Psammoclema sp. (Sodwana Bay, Durban, South Africa). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL). Ref: A. Rubi, et al, Tet. Lett., 1995, 36, 4853

H

O

O

3.38 Obtusane Diterpenoids 249 14-Bromo-1-obtusene-3,11-diol Type: Obtusane diterpenoids. C20H35BrO2 Cryst., mp 134–135 °C, [α]D = +20° (c = 0.3, EtOH). Source: Sea hare Aplysia dactylomela. Pharm: Cytotoxic. Ref: F. J. Schmitz, et al, JOC, 1979, 44, 2445 OH

OH Br

H

H

3.39 Irieol Diterpenoids 250 10-Acetoxyangasiol Type: Irieol diterpenoids. C22H32Br2O5 White powder, [α]D25 = +6.4° (c = 0.9, CHCl3). Source: Red alga Laurencia sp. (N. Borneo I., Sabah, Malaysia). Pharm: Antibacterial (30 mg/disc: Staphylococcus aureus, IZD = 10 mm, MIC = 250 μg/mL; Staphylococcus sp., IZD = 12 mm, MIC = 200 μg/mL; Vibrio cholera, IZD = 18 mm, MIC = 100 μg/mL). Ref: C. S. Vairappan, et al, Mar. Drugs, 2010, 8, 1743 Br

O Br

O H

H O

O

OH

3.41 Spiroditerpenoids

93

3.40 Sphenolobane Diterpenoids 251 (–)-Reiswigin A 3-Sphenolobene-5,16-dione Type: Sphenolobane diterpenoids. C20H32O2 [α]D20 = −10.3° (c = 0.6, CDCl3). Source: Sponge Epipolasis reiswigi. Pharm: Antiviral. (HSV-1 virus and A59 hepatitis virus, in vitro, potent). Ref: Y. Kashman, et al, Tet. Lett., 1987, 28, 5461│ D. Kim, et al, Tet. Lett., 1994, 35, 7957 O

O H

252 Reiswigin B 3,17-Sphenolobadiene-5,16-dione Type: Sphenolobane diterpenoids. C20H30O2 Tan oil, [α]D20 = −20° (c = 0.1, CHCl3). Source: Sponge Epipolasis reiswigi. Pharm: Antiviral. Ref: Y. Kashman, et al, Tet. Lett., 1987, 28, 5461 O

O H

3.41 Spiroditerpenoids 253 Brevione A Type: Spiroditerpenoids. C27H34O4 Oil or white powder, [α]D25 = +111° (c = 0.1, CHCl3). Source: Marine-derived fungus Penicillium sp. (deep sea sediment, East Pacific Ocean), terrestrial fungus (Penicillium brevicompactum). Pharm: Cytotoxic (MCF7, IC50 = 28.4 μmol/L, control Cisplatin, IC50 = 8.09 μmol/L; A549, 50 μg/mL, inactive); allelopathic. Ref: H. Takikawa, et al, Tetrahedron, 2006, 62, 39│ F. A. Macías, et al, Tet. Lett., 2000, 41, 2683│ Y. Li, et al, Mar. Drugs, 2012, 10, 497

94

3 Diterpenoids

O O

H O

O

H

254 Brevione B Type: Spiroditerpenoids. C27H36O4 Oil or white powder, [α]D25 = +65.9° (c = 0.24, CHCl3). Source: Marine-derived fungus Penicillium sp. (deep sea sediment, East Pacific Ocean), terrestrial fungus (Penicillium brevicompactum). Pharm: Allelopathic (etiolated wheat coleoptiles bioassay). Ref: F. A. Macías, et al, JOC, 2000, 65, 9039│ Y. Li, et al, Mar. Drugs, 2012, 10, 497

O O

H O

O

H

255 Brevione E Type: Spiroditerpenoids. C28H34O7 Oil, [α]D = +46° (c = 0.28, CHCl3), [α]D25 = +34.5° (c = 0.7, CHCl3). Source: Marine-derived fungus Penicillium sp. MCCC 3A00005 (extreme-tolerant, sediment, depth of 5115 m, East Pacific Ocean), terrestrial fungus (Penicillium brevicompactum). Pharm: Allelopathic (etiolated wheat coleoptiles bioassay, 0.0001 mol/L, InRt = 100%). Ref: F. A. Macías, et al, JOC, 2000, 65, 9039│ Y. Li, et al, JNP, 2009, 72, 912

O

O H H

O

O

H

O

O

O

256 Brevione F Type: Spiroditerpenoids. C27H32O5 Powder, [α]D = +27° (c = 0.15, CHCl3). Source: Marine-derived fungi Penicillium sp. (deep sea sediment, East Pacific Ocean) and Penicillium sp., marine-derived extreme-tolerant fungus Penicillium sp. MCCC 3A00005 (sediment, depth of 5115 m, East Pacific Ocean). Pharm: Cytotoxic (HeLa, 10 μg/mL, InRt = 25.2%); HIV-1 replication inhibitor (C8166, EC50 = 14.7 μmol/L,

3.41 Spiroditerpenoids

95

CC50 > 100 μmol/L, control Indinavir sulfate, EC50 = 8.71 nmol/L). Ref: Y. Li, et al, JNP, 2009, 72, 912│ Y. Li, et al, Mar. Drugs, 2012, 10, 497 HO O O

H H

O

O

257 Brevione G Type: Spiroditerpenoids. C27H32O5 Powder, [α]D = −20° (c = 0.15, CHCl3). Source: Marine-derived fungi Penicillium sp. (deep sea sediment, East Pacific Ocean) and Penicillium sp., marine-derived extreme-tolerant fungus Penicillium sp. MCCC 3A00005 (sediment, depth of 5115 m, East Pacific Ocean). Pharm: Cytotoxic (HeLa, 10 μg/mL, InRt = 44.9%); HIV-1 replication inhibitor (C8166, EC50 > 50 μmol/L, control Indinavir sulfate, EC50 = 8.71 nmol/L). Ref: Y. Li, et al, JNP, 2009, 72, 912│ Y. Li, et al, Mar. Drugs, 2012, 10, 497 HO O O

H H

O

O

258 Brevione H Type: Spiroditerpenoids. C27H30O7 Powder, [α]D = −36° (c = 0.1, CHCl3). Source: Marine-derived fungus Penicillium sp. MCCC 3A00005 (extreme-tolerant, sediment, depth of 5115 m, East Pacific Ocean). Pharm: Cytotoxic (HeLa, 10 μg/mL, InRt = 25.3%); anti-HIV-1 replication (C8166, EC50 > 50 μmol/L, control Indinavir sulfate, EC50 = 8.71 nmol/L). Ref: Y. Li, et al, JNP, 2009, 72, 912 O

O O

H

O H

HO

O

O

259 Brevione I Type: Spiroditerpenoids. C27H34O5 Yellow powder, [α]D25 = +96° (c = 0.1, CHCl3). Source: Marine-derived fungus Penicillium sp. (deep sea sediment, East Pacific Ocean). Pharm: Cytotoxic (MCF7, IC50 = 7.44 μmol/L, control Cisplatin, IC50 = 8.09 μmol/L;

96

3 Diterpenoids

A549, IC50 = 32.5 μmol/L, Cisplatin, IC50 = 8.90 μmol/L). Ref: Y. Li, et al, Mar. Drugs, 2012, 10, 497 HO O H O

O

H

3.42 Miscellaneous Diterpenoids 260 Dactylomelol Type: Miscellaneous monocyclic diterpenoids. C20H34BrClO2 Cryst. (CH2Cl2/hexane), mp 85–86 °C, [α]D20 = −34.3° (c = 0.7, CHCl3). Source: Sea hare Aplysia dactylomela. Pharm: Toxic (brine shrimp). Ref: D. M. Estrada, et al, Tet. Lett., 1989, 30, 6219│ M. Wessels, et al, JNP, 2000, 63, 920 O

Br Cl

HO

261 Halitunal Type: Miscellaneous monocyclic diterpenoids. C22H26O4 Source: Green alga Halimeda tuna. Pharm: Antiviral (murine corona virus A59, in vitro). Ref: F. E. Koehn, et al, Tet. Lett., 1991, 32, 169 O O

O H O

262 4-Acetylaplykurodin B Type: Miscellaneous bicyclic diterpenoids. C22H34O4 [α]D20 = −26.1° (c = 0.74, CHCl3). Source: Sea hare Aplysia fasciata (mantle tissues). Pharm: Ichthyotoxic; antifeedant. Ref: A. Spinella, et al, JNP, 1992, 55, 989

3.42 Miscellaneous Diterpenoids

17

97

18

O 4

O

H

O

O

263 Acetylcoriacenone Type: Miscellaneous bicyclic diterpenoids. C22H32O3 Oil. Source: Brown algae Pachydictyon coriaceum and Dilophus ligulatus (Mediterranean Sea). Pharm: Cytotoxic (KB, ED50 > 10 μg/mL, P388, ED50 = 4.4 μg/mL, P388/Dox, ED50 > 10 μg/mL, NSCLC-N6, ED50 = 5.4 μg/mL). Ref: M. Ishitsuka, et al, JOC, 1983, 48, 1937│ N.Bouaicha,et al, JNP, 1993, 56, 1747

H O O

19

O

264 Amphilectolide Type: Miscellaneous bicyclic diterpenoids. C17H24O2 Yellow oil, [α]D25 = +24.7° (c = 1.7, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae (Columbia). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv (6.25 μg/mL, Induces 42%). Ref: A. D. Rodríguez, et al, Tet. Lett., 2000, 41, 5177

H O O H

265 Bromophycoic acid A Type: Miscellaneous bicyclic diterpenoids. C27H43BrO4 Source: Red alga Callophycus sp. (Fiji). Pharm: Cytotoxic; antimalarial; antibacterial. Ref: M. E. Teasdale, et al, JOC, 2012, 77, 8000

98

3 Diterpenoids

HOOC

OH O H

Br

266 Bromophycoic acid B Type: Miscellaneous bicyclic diterpenoids. C27H43BrO5 Source: Red alga Callophycus sp. (Fiji). Pharm: Cytotoxic; antimalarial; antibacterial. Ref: M. E. Teasdale, et al, JOC, 2012, 77, 8000 OH

HOOC O

H

Br OH

267 Bromophycoic acid C Type: Miscellaneous bicyclic diterpenoids. C27H43BrO6 Source: Red alga Callophycus sp. (Fiji). Pharm: Cytotoxic; antimalarial; antibacterial. Ref: M. E. Teasdale, et al, JOC, 2012, 77, 8000 HOOC

OH O

Br

H

OH O

268 Bromophycoic acid D Type: Miscellaneous bicyclic diterpenoids. C27H41BrO5 Source: Red alga Callophycus sp. (Fiji). Pharm: Cytotoxic; antimalarial; antibacterial. Ref: M. E. Teasdale, et al, JOC, 2012, 77, 8000 HOOC

OH O H

Br

O

3.42 Miscellaneous Diterpenoids

99

269 Bromophycoic acid E Type: Miscellaneous bicyclic diterpenoids. C27H37BrO3 Source: Red alga Callophycus sp. (Fiji). Pharm: Cytotoxic; antimalarial; antibacterial. Ref: M. E. Teasdale, et al, JOC, 2012, 77, 8000 HOOC O H

Br H

270 Elisabethin B Type: Miscellaneous bicyclic diterpenoids. C19H28O2 Oil, [α]D25 = −99.0° (c = 1.1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae (Columbia). Pharm: Antineoplastic. Ref: A. D. Rodriguez, et al, JOC, 1998, 63, 7083 H

OO

271 Elisabethin C Type: Miscellaneous bicyclic diterpenoids. C18H28O2 Oil, [α]D25 = −31.2° (c = 0.5, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae (Columbia). Pharm: Antituberculotic (weak). Ref: A. D. Rodriguez, et al, JOC, 1998, 63, 7083 H 3

O

O

272 3-Epiaplykurodinone B Type: Miscellaneous bicyclic diterpenoids. C20H30O3 Amorph. powder, [α]D25 = −98.0° (c = 0.2, CHCl3). Source: Sea hare Aplysia fasciata (Spain). Pharm: Cytotoxic (P388, ED50 = 2.5 μg/mL, HT29, ED50 = 2.5 μg/mL, A549, ED50 = 2.5 μg/mL, MEL28, ED50 = 2.5 μg/mL). Ref: M. J. Ortega, et al, JNP, 1997, 60, 488

100

3 Diterpenoids

17

4

18

1

3

O

H

O

O

273 Epoxyfocardin Type: Miscellaneous bicyclic diterpenoids. C20H30O3 [α]D20 = +29° (c = 0.2, EtOH). Source: Protist ciliate Euplotes focardii (Antarctic). Pharm: Defensive agent. Ref: G. Guella, et al, Helv. Chem. Acta, 1996, 79, 439 HO O

O

14

H

15

H H

274 Focardin Type: Miscellaneous bicyclic diterpenoids. C20H30O2 Source: Protist ciliate Euplotes focardii (Antarctic). Pharm: Defensive agent. Ref: G. Guella, et al, Helv. Chem. Acta, 1996, 79, 439 HO

O

14 15

H H H

275 Fuscoside A Type: Miscellaneous bicyclic diterpenoids. C27H44O7 Oil, [α]D = −64° (c = 0.6, CHCl3). Source: Gorgonian Eunicea fusca (Caribbean Sea). Pharm: Anti-inflammatory. Ref: J. H. Shin, et al, JOC, 1991, 56, 3153 O O O

O

H

HO OH

OH

3.42 Miscellaneous Diterpenoids

101

276 Fuscoside E Type: Miscellaneous bicyclic diterpenoids. C27H44O6 Source: Gorgonian Eunicea fusca (Santa Marta Bay, Caribbean Sea, Colombia). Pharm: Anti-inflammatory (TPAinduced mouse ear edema, 0.5 mg/ear, InRt = 80.5%, control Indomethacin, InRt = 77.3%); antifoulant. Ref: E. Reina, et al, BoMCL, 2011, 21, 5888 OH O OH O O

H O

H

277 Halimedalactone Type: Miscellaneous bicyclic diterpenoids. C20H26O3 Yellow oil, [α]D25 = 0° (c = 1.3, CHCl3). Source: Green algae Halimeda tuna and Halimeda scabra. Pharm: Antimicrobial; cytotoxic. Ref: V. J. Paul, et al, Tetrahedron, 1984, 40, 3053 O

H

O H

O

H H

278 Halimedatrial Type: Miscellaneous bicyclic diterpenoids. C20H26O3 Yellow oil, [α]D25 = −59° (c = 0.9, CHCl3). Source: Green algae Halimeda spp. Pharm: Antibacterial (inhibits growth of marine bacteria); antifungal (inhibits growth of marine fungi); cytotoxic (cell division inhibitor in fertilized sea-urchin eggs); antifeedant (fish). Ref: V. J. Paul, et al, Science, 1983, 221, 747│ V. J. Paul, et al, Tetrahedron, 1984, 40, 3053│ H. Nagaoka, et al, Tet. Lett., 1990, 31, 1573 O H H

O O

279 Isoacetylcoriacenone Type: Miscellaneous bicyclic diterpenoids. C22H32O3 Oil. Source: Brown algae Pachydictyon coriaceum and Dilophus ligulatus (Mediterranean Sea). Pharm:

102

3 Diterpenoids

Cytotoxic (KB, ED50 > 10 μg/mL, P388, ED50 = 6.0 μg/mL, P388/Dox, ED50 > 10 μg/mL, NSCLC-N6, ED50 = 6.8 μg/mL). Ref: M. Ishitsuka, et al, JOC, 1983, 48, 1937│ N.Bouaicha,et al, JNP, 1993, 56, 1747

H O O

19

O

280 Phomactin A Antibiotic Sch 49028 Type: Miscellaneous bicyclic diterpenoids. C20H30O4 Oil, [α]D = +245.6° (c = 0.3, CHCl3) (Sch 49028), [α]D = +175° (c = 0.75, CHCl3) (Phomactin A). Source: Marine-derived fungus Phoma sp. (SANK11486; P10364) from crab Chionoecetes opilio (shell). Pharm: PAcF (platelet activating factor) antagonist. Ref: M. Sugano, et al, JACS, 1991, 113, 5463│ M. Chu, et al, J. Antibiot., 1993, 46, 554│ W. P. D. Goldring, et al, Acc. Chem. Res., 2006, 39, 354 O

OH OH

H

O

281 Phomactin B Type: Miscellaneous bicyclic diterpenoids. C20H30O4 mp 180–182 °C, [α]D = +146° (c = 0.75, CHCl3). Source: Marine-derived fungus Phoma sp. SANK11486 from crab Chionoecetes opilio (shell). Pharm: Platelet aggregation inhibitor (IC50 = 17.0 μg/mL); PAF binding inhibitor (IC50 > 47.9 μg/mL). Ref: M. Chu, et al, JOC, 1994, 59, 564 OH O

13

OH

O

3.42 Miscellaneous Diterpenoids

103

282 Phomactin B1 Type: Miscellaneous bicyclic diterpenoids. C20H30O4 mp 180–182 °C, [α]D = +167.3° (c = 1.0, CHCl3). Source: Marine-derived fungus Phoma sp. SANK11486 from crab Chionoecetes opilio (shell). Pharm: Platelet aggregation inhibitor (IC50 = 9.8 μg/mL); PAF binding inhibitor (IC50 > 2.0 μg/mL). Ref: M. Chu, et al, JOC, 1994, 59, 564 OH O O

13

OH

283 Phomactin B2 Type: Miscellaneous bicyclic diterpenoids. C20H28O3 Oil, [α]D = +173° (c = 5.0, CHCl3). Source: Marine-derived fungus Phoma sp. SANK11486 from crab Chionoecetes opilio (shell). Pharm: Platelet aggregation inhibitor (IC50 = 1.6 μg/mL); PAF binding inhibitor (IC50 > 22.1 μg/mL). Ref: M. Chu, et al, JOC, 1994, 59, 564 O O OH

284 Phomactin C Type: Miscellaneous bicyclic diterpenoids. C20H28O3 mp 97–98 °C, [α]D = +114.3° (c = 1.0, CHCl3). Source: Marine-derived fungus Phoma sp. SANK11486 from crab Chionoecetes opilio (shell). Pharm: Platelet aggregation inhibitor (IC50 = 6.4 μg/mL); PAF binding inhibitor (IC50 > 63.0 μg/mL). Ref: M. Chu, et al, JOC, 1992, 57, 5817; 1994, 59, 564│ M. Chu, et al, J. Antibiot., 1993, 46, 554 O

H

O O

104

3 Diterpenoids

285 Phomactin D Type: Miscellaneous bicyclic diterpenoids. C20H30O3 Cryst., mp 97–98 °C, [α]D22 = +114.3° (c = 1, CHCl3). Source: Marine-derived fungus Phoma sp. from crab Chionoecetes opilio (shell). Pharm: PAcF antagonist (most potent and inhibited PAcF binding to its receptor, IC50 = 0.12 μmol/L); platelet aggregation inhibitor (IC50 = 0.80 μmol/L). Ref: M. Chu, et al, JOC, 1992, 57, 5817│ M. Chu, et al, J. Antibiot., 1993, 46, 554│ M. Sugano, et al, JOC, 1994, 59, 564│ H. Miyaoka, et al, Tet. Lett., 1996, 37, 7107│ T. S. Bugni, et al, NPR, 2004, 21, 143 (rev)

14 1

O O

O

H

286 Phomactin E Type: Miscellaneous bicyclic diterpenoids. C20H30O3 mp 148–149 °C, [α]D25 = +178.4° (CHCl3). Source: Marine-derived fungus Phoma sp. Pharm: Platelet activation factor (PAcF) antagonist; platelet aggregation inhibitor (PAF-induced, IC50 = 2.3 μmol/L); inhibits binding of PAF to its receptors (IC50 = 5.19 μmol/L). Ref: M. Sugano, et al, J. Antibiotics, 1995, 48, 1188 HO

O O

287 Phomactin F Type: Miscellaneous bicyclic diterpenoids. C20H30O4 mp 199–202 °C, [α]D25 = +120.9° (CHCl3). Source: Marine-derived fungus Phoma sp. Pharm: Platelet activation factor (PAcF) antagonist; platelet aggregation inhibitor (PAF-induced, IC50 = 3.9 μmol/L); inhibits binding of PAF to its receptors (IC50 = 35.9 μmol/L). Ref: M. Sugano, et al, J. Antibiotics, 1995, 48, 1188 HO

O O

O

3.42 Miscellaneous Diterpenoids

105

288 Phomactin G Type: Miscellaneous bicyclic diterpenoids. C20H30O3 mp 131–132 °C, [α]D25 = +96.9° (CHCl3). Source: Marine-derived fungus Phoma sp. Pharm: Platelet activation factor (PAcF) antagonist; platelet aggregation inhibitor (PAF-induced, IC50 = 3.2 μmol/L); inhibits binding of PAF to its receptors (IC50 = 0.38 μmol/L). Ref: M. Sugano, et al, J. Antibiotics, 1995, 48, 1188 O

OH O

289 Sinutriangulin A Type: Miscellaneous bicyclic diterpenoids. C20H32O2 Source: Soft coral Sinularia triangula (Taitung County, Taiwan). Pharm: Cytotoxic (CCRF-CEM, ED50 = 10.1 μg/mL; DLD-1, ED50 = 15.2 μg/mL). Ref: M. -C. Lu, et al, Tet. Lett., 2011, 52, 5869

H

HO

O

290 Xeniafaraunol A Type: Miscellaneous bicyclic diterpenoids. C20H28O2 Colorless glass, [α]D = +5° (c = 0.01, CHCl3). Source: Soft coral Xenia faraunensis (Red Sea). Pharm: Cytotoxic (P388). Ref: Y. Kashman, et al, Tet. Lett., 1994, 35, 8855 O H H OH

291 Xeniafaraunol B Type: Miscellaneous bicyclic diterpenoids. C20H28O3 Oil, [α]D = −73° (c = 0.04, MeOH); colorless glass. Source: Soft corals Xenia faraunensis (Red Sea) and Xenia

106

3 Diterpenoids

florida (Japan waters). Pharm: Cytotoxic (P388). Ref: Y. Kashman, et al, Tet. Lett., 1994, 35, 8855│ T. Iwagawa, et al, JNP, 2000, 63, 468 O H O OH

H

292 Bielschowskysin Type: Miscellaneous tricyclic diterpenoids. C22H26O9 Cryst., mp 139–141 °C, [α]D20 = −17.3° (c = 1.1, MeOH). Source: Gorgonian Pseudopterogorgia kallos (West Indian Sea, Caribbean Sea). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 10 μg/mL); cytotoxic (EKVX, GI50 < 0.01 μmol/L; CAKI-1, GI50 = 0.51 μmol/L); antineoplastic. Ref: J. Marrero, et al, Org. Lett. 2004, 6, 1661 H

HO

OH H

H

OH

O

O O

O

H

O O

293 Caribenol A Type: Miscellaneous tricyclic diterpenoids. C19H26O3 Solid, [α]D20 = +40° (c = 1, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae(San Andre´s Archipelago, Colombia). Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC = 63 μg/mL); antiplasmodial (CRPF W2, IC50 = 20 μg/mL, weak). Ref: X. Wei, et al, JOC, 2007, 72, 7386│ L. -Z. Liu, et al, JACS, 2010, 132, 13608 H H

HO

O

O

294 Caribenol B Type: Miscellaneous tricyclic diterpenoids. C19H28O3 Oil, [α]D20 = +26.8° (c = 0.7, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae (San Andre´s Archipelago, Colombia). Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC = 128 μg/mL). Ref: X. Wei, et al, JOC, 2007, 72, 7386

3.42 Miscellaneous Diterpenoids

107

H OH HO

295 Chatancin Type: Miscellaneous tricyclic diterpenoids. C21H32O4 Needles (MeOH aq), mp 106–108 °C, [α]D = +10.5° (c = 1, CHCl3). Source: Soft corals Sinularia pavida (Sanya Bay, Hainan I., South China Sea) and Sarcophyton sp. Pharm: Cytotoxic (HL60, HCT8, HepG2, BGC823, A549, and A375, all IC50s > 10 μg/mL); platelet aggregation inhibitor (PAF-induced, IC50 = 2.2 μmol/L); inhibits the binding of PAF to its receptors (IC50 = 0.32 μmol/L). Ref: M. Sugano, et al, JOC, 1990, 55, 5803│ J. Aigner, et al, Angew. Chem., Int. Ed., 1998, 37, 2226│ S. Shen, et al, Tet. Lett., 2012, 53, 5759

H O H O

O

OH

296 Chromodorolide B Type: Miscellaneous tricyclic diterpenoids. C26H36O9 Oil, [α]D = −95° (c = 0.1, CH2Cl2). Source: Nudibranch Chromodoris cavae, an unidentified sponge (Australia). Pharm: Cytotoxic (P388, 10 μg/mL, InRt = 70%). Ref: S. A. Morris, et al, Can. J. Chem., 1991, 69, 768│ W. Rungprom, et al, Mar. Drugs, 2004, 2, 101 O

O

O O

O

H 12

H H H

O O O O

297 Chromodorolide C Type: Miscellaneous tricyclic diterpenoids. C24H34O8 Oil, [α]D = −78° (c = 0.1, CH2Cl2). Source: Sponge Aplisia sp. (Australia). Pharm: Cytotoxic (P388, 10 μg/mL, InRt = 42%). Ref: W. Rungprom, et al, Mar. Drugs, 2004, 2, 101

108

3 Diterpenoids

O HO O

H

O

12

O

O

H H

O O

H

298 Elisabanolide Type: Miscellaneous tricyclic diterpenoids. C19H26O4 Cryst., [α]D25 = −39.0° (c = 0.4, CHCl3). Source: Gorgonians Pseudopterogorgia elisabethae (Columbia) and Pseudopterogorgia elisabethae (West Indian Sea, Caribbean Sea). Pharm: Antituberculotic (weak). Ref: A. D. Rodriguez, et al, JOC, 1998, 63, 7083│ A. D. Rodriguez, et al, JOC, 2000, 65, 1390 H H H O

O

O

299 3-epi-Elisabanolide Type: Miscellaneous tricyclic diterpenoids. C19H26O4 Cryst., [α]D25 = −4° (c = 1.5, CHCl3). Source: Gorgonians Pseudopterogorgia elisabethae (Columbia) and Pseudopterogorgia elisabethae (West Indian Sea, Caribbean Sea). Pharm: Antituberculotic (strong in vitro). Ref: A. D. Rodríguez, et al, JOC, 2000, 65, 1390 H H

3

H O

O O O

300 Elisabethin D 2α-Hydroxyelisabethin A Type: Miscellaneous tricyclic diterpenoids. C20H28O4 Cryst., [α]D25 = +6.4° (c = 1.2, CHCl3). Source: Gorgonians Pseudopterogorgia elisabethae (Columbia) and Pseudopterogorgia elisabethae (West Indian Sea, Caribbean Sea). Pharm: Antituberculotic (strong in vitro); cytotoxic (SF268, NCI-H460, MCF7, no significant activity). Ref: A. D. Rodríguez, et al, JOC, 2000, 65, 1390│ A. D. Rodríguez, et al, Tet. Lett., 2000, 41, 5177

3.42 Miscellaneous Diterpenoids

OH

109

O OH

O

301 Elisabethin D acetate Type: Miscellaneous tricyclic diterpenoids. C22H30O5 Oil, [α]D25 = +26.3° (c = 2.8, CHCl3). Source: Gorgonians Pseudopterogorgia elisabethae (Columbia) and Pseudopterogorgia elisabethae (West Indian Sea, Caribbean Sea). Pharm: Antituberculotic (strong in vitro). Ref: A. D. Rodríguez, et al, JOC, 2000, 65, 1390 OH

O O

O

O

302 Ethyl plumarellate Type: Miscellaneous tricyclic diterpenoids. C23H32O7 Cryst., mp 136–138 °C, [α]D25 = +84.1° (c = 0.27, EtOAc/EtOH). Source: Gorgonian Plumarella sp. (psychrophilic, cold water, near Kuril Is., Northwestern Pacific Ocean). Pharm: Hemolytic (against mouse-blood erythrocytes, inducing 50% hemolysis at 250 μmol/L). Ref: V. A. Stonik, et al, Tet. Lett., 2002, 43, 315│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) OH

OH

H HO

O

H

O O

OH

H

303 JBIR 65 Type: Miscellaneous tricyclic diterpenoids. C19H24O4 Source: Sponge Actinomadura sp. (Ishigaki I., Okinawa). Pharm: Antioxidant (scavenger, modest). Ref: M. Takagi, et al, J. Antibiot., 2010, 63, 401 OH O O HO

110

3 Diterpenoids

304 Myrocin D Type: Miscellaneous tricyclic diterpenoids. C19H24O5 Yellow powder; [α]D22 = +18.2° (c = 1.25, MeOH). Source: Marine-derived fungus Arthrinium sp. from sponge Geodia cydonium (Adriatic Sea, Italy). Pharm: Cytotoxic (L5178Y, IC50 = 2.05 μmol/L, control Kahalalide F, IC50 = 4.30 μmol/L; K562, IC50 = 50.3 μmol/L, control Cisplatin, IC50 = 7.80 μmol/L; A2780, IC50 = 41.3 μmol/L, Cisplatin, IC50 = 0.80 μmol/L; A2780CisR, IC50 = 66.0 μmol/L, Cisplatin, IC50 = 8.40 μmol/L); inhibits VEGF-A dependent endothelial cell sprouting (cellular angiogenesis assay, IC50 = 2.60 μmol/L, control Sunitinib, IC50 = 0.12 μmol/L). Ref: S. S. Ebada, et al, BoMC, 2011, 19, 4644 OH

OH

O OH O

305 Nanolobatolide Type: Miscellaneous tricyclic diterpenoids. C18H26O3 Source: Soft coral Sinularia nanolobata (Taiwan waters). Pharm: Antineuroinflammatory. Ref: Y. -J. Tseng, et al, Org. Lett., 2009, 11, 5030 O

O OH

306 Plumarellide Type: Miscellaneous tricyclic diterpenoids. C21H26O6 Cryst. (MeOH), mp 223–225 °C, [α]D25 = +109.6° (c = 0.23, CHCl3/MeOH). Source: Gorgonian Plumarella sp. (psychrophilic, cold water, near Kuril Is., Northwestern Pacific Ocean). Pharm: Hemolytic (against mouse-blood erythrocytes, inducing 50% hemolysis at 140 μmol/L). Ref: V. A. Stonik, et al, Tet. Lett., 2002, 43, 315│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) OH

OH

H O O

O

H H

OH

3.42 Miscellaneous Diterpenoids

111

307 Plumisclerin A Type: Miscellaneous tricyclic diterpenoids. C26H36O8 Source: Gorgonian Plumigorgia terminosclera (Mayotte I., Madagascar Channel, Comoros Is.). Pharm: Cytotoxic (moderate). Ref: M. J. Martın, et al, Org. Lett., 2010, 12, 912 O

O H

H

O

O O

H

O O

O

308 Sarcophytin Type: Miscellaneous tricyclic diterpenoids. C21H30O5 Cryst., mp 160–162 °C, [α]D25 = +924.4° (c = 0.5, CHCl3); mp 162–163 °C, [α]D25 = +0.24° (c = 0.08, CHCl3). Source: Soft corals Sinularia pavida (Sanya Bay, Hainan I., South China Sea) and Sarcophyton elegans (Andaman and Nicobar Is., Indian Ocean). Pharm: Cytotoxic (HL60, HCT8, HepG2, BGC823, A549, and A375, all IC50s > 10 μg/mL). Ref: A. S. R. Anjaneyulu, et al, Indian J. Chem., Sect. B, 1998, 37, 1090│ A. S. R. Anjaneyulu, et al, Tet. Lett., 1998, 39, 139│ A. S. R, Anjaneyuju, et al, J. Indian Chem. Soc., 1999, 76, 651│ S. Shen, et al, Tet. Lett., 2012, 53, 5759 OH

H

O H O

O

O

309 Aberrarone Type: Miscellaneous tetracyclic diterpenoids. C20H26O4 Orange cryst., [α]D25 = +2.2° (c = 1.4, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae (deep reef waters of 28 m, off San Andres I., Colombia). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 10 μg/mL). Ref: I. I. Rodriguez, et al, JOC, 2009, 74, 7581 O

O O O H

H

H

112

3 Diterpenoids

310 15-Chloro-14-hydroxyxestoquinone Type: Miscellaneous tetracyclic diterpenoids. C20H13ClO5 Yellow solid, [α]D = +29.6° (c = 2.8, CHCl3). Source: Sponge Xestospongia sp. Pharm: Topoisomerase II inhibitor. Ref: G. P. Concepcion, et al, JMC, 1995, 38, 4503 Cl O

OH O

O O

311 14-Chloro-15-hydroxyxestoquinone Type: Miscellaneous tetracyclic diterpenoids. C20H13ClO5 Yellow solid. Source: Sponge Xestospongia sp. Pharm: Topoisomerase II inhibitor. Ref: G. P. Concepcion, et al, JMC, 1995, 38, 4503 OH O

Cl

16

13

O

O O

312 Colombiasin A Type: Miscellaneous tetracyclic diterpenoids. C20H26O3 Yellow oil, [α]D25 = −55.3° (c = 0.9, CHCl3). Source: Gorgonian Pseudopterogorgia elisabethae (Columbia). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 10 μg/mL). Ref: A. D. Rodriguez, et al, Org. Lett., 2000, 2, 507│ I. I. Rodriguez, et al, JOC, 2009, 74, 7581 H O

O

OH

313 Conidiogenol Type: Miscellaneous tetracyclic diterpenoids. C20H34O2 Oil, [α]D20 = −20° (c = 0.07, CHCl3). Source: Marine-derived fungus Penicillium chrysogenum from red alga

3.42 Miscellaneous Diterpenoids

113

Laurencia sp. (Weizhou I., Guangxi, China), terrestrial fungus (Penicillium cyclopium). Pharm: Antibacterial (Pseudomonas fluorescens, and Staphylococcus epidermidis, each with MIC = 16 μg/mL). Ref: T. Rancal, et al, Tet. Lett., 2002, 43, 6799│ S. -S. Gao, et al, Chem. Biodiversity, 2011, 8, 1748 OH 1

7

H

HO

H

314 Conidiogenone B Type: Miscellaneous tetracyclic diterpenoids. C20H30O Oil, [α]D20 = −6° (c = 0.55, MeOH). Source: Marine-derived fungi Penicillium chrysogenum from red alga Laurencia sp. (Weizhou I., Guangxi, China) and Penicillium sp. F23-2 (sediment, depth of 5080 m). Pharm: Cytotoxic (A549, IC50 = 40.3 μmol/L; HL60, IC50 = 28.2 μmol/L; Bel7402, IC50 > 50 μmol/L; Molt4, IC50 > 50 μmol/L); antibacterial (MRSA, Pseudomonas fluorescens, Pseudomonas aeruginosa, and Staphylococcus epidermidis, each with MIC = 8 μg/mL). Ref: L. Du, et al, Tetrahedron, 2009, 65, 1033│ S. -S. Gao, et al, Chem. Biodiversity, 2011, 8, 1748 O 7

H H

12

20 19

13

315 Conidiogenone C Type: Miscellaneous tetracyclic diterpenoids. C20H30O2 Oil, [α]D20 = −11.9° (c = 0.04, MeOH). Source: Marine-derived fungus Penicillium sp. F23-2 (sediment, depth of 5080 m). Pharm: Cytotoxic (A549, IC50 > 50 μmol/L; HL60, IC50 = 0.038 μmol/L; Bel7402, IC50 = 0.97 μmol/L; Molt4, IC50 > 50 μmol/L). Ref: L. Du, et al, Tetrahedron, 2009, 65, 1033 O 7

H H 20 12

13

19

OH

114

3 Diterpenoids

316 Conidiogenone D Type: Miscellaneous tetracyclic diterpenoids. C20H30O2 Oil, [α]D20 = −8.6° (c = 0.34, MeOH). Source: Marine-derived fungus Penicillium sp. F23-2 (sediment, depth of 5080 m). Pharm: Cytotoxic (A549, IC50 = 9.3 μmol/L; HL60, IC50 = 5.3 μmol/L; Bel7402, IC50 = 11.7 μmol/L; Molt4, IC50 = 21.1 μmol/L). Ref: L. Du, et al, Tetrahedron, 2009, 65, 1033 O

7

H H

20

OH 12

19

13

317 Conidiogenone E Type: Miscellaneous tetracyclic diterpenoids. C20H30O2 Oil, [α]D20 = −26.2° (c = 0.075, MeOH). Source: Marine-derived fungus Penicillium sp. F23-2 (sediment, depth of 5080 m). Pharm: Cytotoxic (A549, IC50 = 15.1 μmol/L; HL60, IC50 = 8.5 μmol/L; Bel7402, IC50 > 50 μmol/L; Molt4, IC50 = 25.8 μmol/L). Ref: L. Du, et al, Tetrahedron, 2009, 65, 1033 O

7

H H 20 12

HO

19 13

318 Conidiogenone F Type: Miscellaneous tetracyclic diterpenoids. C20H30O2 Oil, [α]D20 = −13.7° (c = 0.06, MeOH). Source: Marine-derived fungus Penicillium sp. F23-2 (sediment, depth of 5080 m). Pharm: Cytotoxic (A549, IC50 = 42.2 μmol/L; HL60, IC50 = 17.8 μmol/L; Bel7402, IC50 = 17.1 μmol/L; Molt4, IC50 > 50 μmol/L). Ref: L. Du, et al, Tetrahedron, 2009, 65, 1033

3.42 Miscellaneous Diterpenoids

115

O

7

H H 13

20 19

12

OH

319 Conidiogenone G Type: Miscellaneous tetracyclic diterpenoids. C20H30O2 Oil, [α]D20 = +27.7° (c = 0.09, MeOH). Source: Marine-derived fungus Penicillium sp. F23-2 (sediment, depth of 5080 m). Pharm: Cytotoxic (A549, IC50 = 8.3 μmol/L; HL60, IC50 = 1.1 μmol/L; Bel7402, IC50 = 43.2 μmol/L; Molt4, IC50 = 4.7 μmol/L). Ref: L. Du, et al, Tetrahedron, 2009, 65, 1033 O OH

7

H H 12

20 19

13

320 Conidiogenone H Type: Miscellaneous tetracyclic diterpenoids. C18H28O3 Source: Marine-derived fungus Penicillium chrysogenum from red alga Laurencia sp. (Weizhou I., Guangxi, China). Pharm: Antibacterial (MRSA, Pseudomonas fluorescens, Pseudomonas aeruginosa, and Staphylococcus epidermidis,each with MIC > 256 μg/mL). Ref: S. -S. Gao, et al, Chem. Biodiversity, 2011, 8, 1748 O

HO

H HO

H

321 Conidiogenone I Type: Miscellaneous tetracyclic diterpenoids. C19H33O3 Source: Marine-derived fungus Penicillium chrysogenum [Syn. Penicilliumchrysogenum] from red alga Laurencia sp. (Weizhou I., Guangxi, China). Pharm: Antibacterial (MRSA, Pseudomonas

116

3 Diterpenoids

fluorescens, Pseudomonasaeruginosa, and Staphylococcus epidermidis,each with MIC > 256 μg/mL). Ref: S. -S. Gao, et al, Chem. Biodiversity, 2011, 8, 1748 O

HO

H OH

H

322 14,15-Dihydroxymethylxestoquinone Type: Miscellaneous tetracyclic diterpenoids. C20H16O5 Source: Sponge Petrosia alfiani (Malaysia). Pharm: Activator of hypoxia-inducible factor-1 (HIF-1). Ref: V. Costantino, et al, JOC, 2012, 77, 6377 O

O O

O

323 Elisapterosin A Type: Miscellaneous tetracyclic diterpenoids. C20H28O5 Cryst., [α]D25 = +140.7° (c = 1.4, CHCl3). Source: Gorgonians Pseudopterogorgia elisabethae (Columbia) and Pseudopterogorgia elisabethae (West Indian Sea, Caribbean Sea). Pharm: Antituberculotic (strong in vitro). Ref: A. D. Rodríguez, et al, JOC, 2000, 65, 1390 H H

OH

O H

16

O

O OH

324 Elisapterosin B Type: Miscellaneous tetracyclic diterpenoids. C20H26O3 Cryst., [α]D25 = −3° (c = 4.4, CHCl3). Source: Gorgonians Pseudopterogorgia elisabethae (Columbia) and Pseudopterogorgia elisabethae (West Indian Sea, Caribbean Sea). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 79%); cytotoxic (SF268, NCI-H460, MCF7, no significant activity). Ref: A. D. Rodríguez, et al, JOC, 2000, 65, 1390

3.42 Miscellaneous Diterpenoids

117

H H

2

O

17

OH

11 12

O

325 Halenaquinol 8,11-Dihydroxy-12b-methyl-1H-benzo[6,7]phenanthro[10,1-bc]furan-3,6(2H,12bH)dione Type: Miscellaneous tetracyclic diterpenoids. C20H14O5 Yellow solid, [α]577.00 = +179° (Me2CO). Source: Sponges Xestospongia carbonaria (Fiji) and Xestospongia sapra. Pharm: Tyrosine kinase pp60V-SRC inhibitor (IC50 = 60.0 μmol/L); antibiotic; cardiotonic; antiviral (potent irreversible inhibitor of Rous sarcoma virus). Ref: N. Harada, et al, JACS, 1989, 111, 5668│ R. H. Lee, et al, Biochem. Biophys. Res. Commun. 1992, 184, 765│ K. A. Alvi, et al, JOC, 1993, 58, 4871│ P. Wipf, et al, Org. Biomol. Chem., 2005, 3, 2053│ D. Skropeta, et al, Mar. Drugs 2011, 9, 2131 (rev)

OH

O

O

326 Halenaquinol O16-Sulfate Type: Miscellaneous tetracyclic diterpenoids. C20H14O8S Yellow solid, [α]577.00 = +106° (Me2CO). Source: Sponges Xestospongia carbonaria (Fiji) and Xestospongia sapra. Pharm: Tyrosine kinase pp60V-SRC inhibitor (IC50 = 0.55 μmol/L). Ref: M. Kobayashi, et al, CPB, 1985, 33, 1305│ R. H. Lee,et al, Biochem. Biophys. Res. Commun. 1992, 184, 765│ J. Kobayashi, et al, JNP, 1992, 55, 994│ D. Skropeta, et al, Mar. Drugs 2011, 9, 2131 (rev) O HO

S

O

O

OH

O

O O

327 Halenaquinone Type: Miscellaneous tetracyclic diterpenoids. C20H12O5 Yellow solid, mp > 250 °C, [α]D25 = +22.2° (c = 0.124, CHCl3); mp 186–188 °C, [α]D25 = +62.1° (c = 0.066, CH2Cl2).

118

3 Diterpenoids

Source: Sponges Xestospongia carbonaria (Fiji), Xestospongia sp (Vanuatu), Xestospongia exigua, Adocia sp. and Spongia sp. Pharm: Tyrosine kinase pp60V-SRC inhibitor (IC50 = 1.5 μmol/L); hmn kinase EGFR inhibitor (IC50 = 19 μmol/L); antibiotic; cardiotonic activity; antineoplastic (arrests proliferation of various cell lines, including those that have been transformed by oncogenic PTKs); recombinant hmn Cdc25b phosphatase inhibitor (an activator of cyclin dependent kinase Cdc2 whose presence is required for entry into the mitosis phase of the cell cycle, IC50 = 0.7 μmol/L); DNA topoisomerase I inhibitor (MIC = 0.4 μg/mL); antibacterial (Staphylococcus aureus, Bacillus subtilis). Ref: D. M. Roll, et al, JACS, 1983, 105, 6177│ H. Nakamura, et al, Chem. Lett., 1985, 6177│ M. Kobayashi, et al, CPB, 1985, 33, 1305│ M. Kobayashi, et al, Tet. Lett., 1985, 26, 3833│ R. H. Lee,et al, Biochem. Biophys. Res. Commun. 1992, 184, 765│ J. Kobayashi, et al, JNP, 1992, 55, 994│ K. A. Alvi, et al, JOC, 1993, 58, 4871│ F. Miyazaki, et al, Tetrahedron, 1998, 54, 13073│ P. Wipf, et al, Org. Biomol. Chem., 2005, 3, 2053│ S. Cao, et al, BoMC 2005, 13, 999│ D. Skropeta, et al, Mar. Drugs 2011, 9, 2131 (rev) O

O

O

O O

328 15-Hydroxymethylxestoquinone Type: Miscellaneous tetracyclic diterpenoids. C21H16O5 Source: Sponge Petrosia alfiani (Malaysia). Pharm: Activator of hypoxia-inducible factor-1 (HIF-1). Ref: V. Costantino, et al, JOC, 2012, 77, 6377 O OH O O

O

329 14-Hydroxymethylxestoquinone Type: Miscellaneous tetracyclic diterpenoids. C21H16O5 Source: Sponge Petrosia alfiani (Malaysia). Pharm: Activator of hypoxia-inducible factor-1 (HIF-1); enhances respiration and decreases mitochondrial membrane potential (suggesting mode of action uncouples mitochondrial respiration). Ref: V. Costantino, et al, JOC, 2012, 77, 6377│ L. Du, et al, JNP, 2012, 75, 1553

3.42 Miscellaneous Diterpenoids

119

O

O

OH O

O

330 Hypoxysordarin Type: Miscellaneous tetracyclic diterpenoids. C36H50O11 Oil, [α]D = +17° (c = 0.35, CHCl3). Source: Marine-derived fungus Hypoxylon croceum from driftwood (in a mangrove estuary in Everglades, Florida). Pharm: Antifungal (serial dilution assay: Absidia glauca, Mucor miehei, Paecilomyces variotii, Penicillium notatum, Penicillium islandicum, MIC50 (Fungistatic, the growth restarted after removal of the compound) = 20, 1, 2, 2, 10 μg/mL, respectively); cytotoxic (HL60, IC50 = 50 μg/mL). Ref: M. Daferner, et al, Z. Naturforsch., Teil C, 1999, 54, 474

O O

H

H

O

O

O

HO

O

O

O

OH

H

H O

331 14-Methoxyhalenaquinone Methoxyhalenaquinone Type: Miscellaneous tetracyclic diterpenoids. C21H14O6 Reddish–yellow solid. Source: Sponges Xestospongia cf. carbonaria and Xestospongia sp. (Indonesia). Pharm: Tyrosine protein kinase TPK Inhibitor (IC50 = 5 μmol/L). Ref: K. A. Alvi, et al, JOC, 1993, 58, 4871│ Y. Zhu, et al, Heterocycles, 1998, 49, 355│ M. Gordaliza, et al, Mar. Drugs 2010, 8, 2849 (rev)│ D. Skropeta, et al, Mar. Drugs 2011, 9, 2131 (rev) O

O O

O

O O

120

3 Diterpenoids

332 15-Methoxyxestoquinone Type: Miscellaneous tetracyclic diterpenoids. C21H16O5 Yellow solid. Source: Sponge Xestospongia sp. Pharm: Topoisomerase II inhibitor. Ref: G. P. Concepcion, et al, JMC, 1995, 38, 4503 O O

O

O O

333 14-Methoxyxestoquinone Type: Miscellaneous tetracyclic diterpenoids. C21H16O5 Yellow solid, [α]D = +13.1° (c = 3.1, CHCl3). Source: Sponge Xestospongia sp. Pharm: Topoisomerase II inhibitor; protein tyrosine kinase inhibitor. Ref: K. A. Alvi, et al, JOC, 1993, 58, 4871│ G. P. Concepcion, et al, JMC, 1995, 38, 4503 O

O O

O O

334 (–)-Prehalenaquinone Type: Miscellaneous tetracyclic diterpenoids. C20H16O5 Crystals, mp 207 °C (synthetic), [α]D = −47.5° (c = 0.747, CHCl3) (synthetic). Source: Sponge Xestospongia sapra (Okinawa). Pharm: Putative biosynthetic precursor to Halenaquinol and xestoquinone (GMT30 in DNP). Ref: N. Harada, et al, JOC, 1994, 59, 6606 O O

HO

H

O O

3.42 Miscellaneous Diterpenoids

121

335 Secoadociaquinone A Type: Miscellaneous tetracyclic diterpenoids. C22H19NO7S Orange solid. Source: Sponge Xestospongia sp. Pharm: Topoisomerase II inhibitor. Ref: G. P. Concepcion, et al, JMC, 1995, 38, 4503 H N

S

O

O

O OH

O

O O

336 Secoadociaquinone B Type: Miscellaneous tetracyclic diterpenoids. C22H19NO7S Orange solid, [α]D = +30.3° (c = 1.1, MeOH). Source: Sponge Xestospongia sp. Pharm: Topoisomerase II inhibitor. Ref: G. P. Concepcion, et al, JMC, 1995, 38, 4503 O

H N

16

S

13

O

O

O OH

O O

337 Tetrahydrohalenaquinone A Type: Miscellaneous tetracyclic diterpenoids. C20H20O5 Solid, mp 234 °C, [α]D = +12°. Source: Sponge Xestospongia cf. carbonaria. Pharm: PTK inhibitor. Ref: K. A. Alvi, et al, JOC, 1993, 58, 4871 O OH

HO

H

O O

122

3 Diterpenoids

338 Tetrahydrohalenaquinone B Xestosaprol A epimer Type: Miscellaneous tetracyclic diterpenoids. C20H20O5 Solid, mp 234 °C, [α]D = +24°. Source: Sponge Xestospongia cf. carbonaria. Pharm: PTK inhibitor. Ref: K. A. Alvi, et al, JOC, 1993, 58, 4871 HO O

HO

O

H

O

339 Xestoquinol 16-sulfate Type: Miscellaneous tetracyclic diterpenoids. C20H16O7S [α]D25 = +27° (c = 0.56, MeOH). Source: Sponge Xestospongia sapra. Pharm: DNA topoisomerase I inhibitor (MIC = 10 μg/mL). Ref: J. Kobayashi, et al, JNP, 1992, 55, 994 HO O

O S

O

O OH

O

340 Xestoquinone Type: Miscellaneous tetracyclic diterpenoids. C20H14O4 Yellow powder, mp 212–214 °C (dec), [α]D25 = +17.2° (c = 1.16, CH2Cl2). Source: Sponges Xestospongia carbonaria (Fiji), Xestospongia sp. (Vanuatu)，Xestospongia sapra and Adocia sp. Pharm: Tyrosine kinase pp60V-SRC inhibitor (IC50 = 28.0 μmol/L); kinase Pfnek-1 inhibitor (Plasmodium falciparum, IC50 = 1.1 μmol/L); kinase PfPK5 inhibitor (lower activity); cardiotonic; topoisomerase I inhibitor. Ref: H. Nakamura, et al, Chem. Lett., 1985, 713│ R. H. Lee, et al, Biochem. Biophys. Res. Commun. 1992, 184, 765│ D. Skropeta, et al, Mar. Drugs 2011, 9, 2131 (rev) O

16 13

O

O O

3.42 Miscellaneous Diterpenoids

123

341 Xestosaprol A Type: Miscellaneous tetracyclic diterpenoids. C20H20O5 Yellow solid, [α]D27 = −42° (c = 0.35, MeOH). Source: Sponge Xestospongia sapra. Pharm: DNA topoisomerase I inhibitor (MIC = 12.5 μg/mL). Ref: J. Kobayashi, et al, JNP, 1992, 55, 994 OH

OH

H

13

O

O O

342 Xestosaprol A 13-hydroxy-16-ketone isomer Type: Miscellaneous tetracyclic diterpenoids. C20H20O5 Source: Sponge Xestospongia sapra. Pharm: DNA topoisomerase I inhibitor (MIC = 2.5 μg/mL). Ref: J. Kobayashi, et al, JNP, 1992, 55, 994 OH

O

H

16

O

13

OH

O

343 Xestosaprol B Type: Miscellaneous tetracyclic diterpenoids. C20H22O5 Yellow solid, [α]D27 = +49° (c = 0.22, MeOH). Source: Sponge Xestospongia sapra. Pharm: DNA topoisomerase I inhibitor (MIC = 12.5 μg/mL). Ref: J. Kobayashi, et al, JNP, 1992, 55, 994 OH

OH

H O

13

OH

O

344 Xestosaprol F Type: Miscellaneous tetracyclic diterpenoids. C22H22O5 Yellow powder, [α]D22 = +14° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (135 ± 11)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L). Ref: J. Dai, et al, JNP, 2010, 73, 1188

124

3 Diterpenoids

HO H

O O

O

OH

345 Xestosaprol G Type: Miscellaneous tetracyclic diterpenoids. C20H18O4 Yellow powder, [α]D22 = −8.7° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (155 ± 15)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L). Ref: J. Dai, et al, JNP, 2010, 73, 1188 HO H

O O

OH

346 Xestosaprol H Type: Miscellaneous tetracyclic diterpenoids. C22H22O5 Yellow powder, [α]D22 = −10° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (82 ± 3)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L; BACE1 is a central role in etiology of Alzheimer’s disease). Ref: J. Dai, et al, JNP, 2010, 73, 1188 HO H

O O

O

OH

347 Xestosaprol I Type: Miscellaneous tetracyclic diterpenoids. C20H18O3 Yellow powder, [α]D22 = −27° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (163 ± 11)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L). Ref: J. Dai, et al, JNP, 2010, 73, 1188

3.42 Miscellaneous Diterpenoids

125

HO H

O O

348 Xestosaprol J Type: Miscellaneous tetracyclic diterpenoids. C21H20O4 Yellow powder, [α]D22 = −42° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (90 ± 5)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L). Ref: J. Dai, et al, JNP, 2010, 73, 1188 HO

O

H

O O

349 Xestosaprol K Type: Miscellaneous tetracyclic diterpenoids. C20H18O4 Yellow powder, [α]D22 = −20° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (93 ± 4)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L). Ref: J. Dai, et al, JNP, 2010, 73, 1188 HO

OH

H

O O

350 Xestosaprol L Type: Miscellaneous tetracyclic diterpenoids. C20H18O3 Yellow powder, [α]D22 = −8.7° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (98 ± 8)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L). Ref: J. Dai, et al, JNP, 2010, 73, 1188

126

3 Diterpenoids

HO H

O O

351 Xestosaprol M Type: Miscellaneous tetracyclic diterpenoids. C20H16O2 Yellow powder, [α]D22 = +17° (c = 0.2, MeOH). Source: Sponge Xestospongia sp. (Sangalaki, Indonesia). Pharm: BACE1 aspartic protease inhibitor (IC50 = (104 ± 8)μmol/L, standard Secretase inhibitor IV, IC50 = (0.015 ± 0.001)μmol/L). Ref: J. Dai, et al, JNP, 2010, 73, 1188

O O

352 Xestosaprol O Type: Miscellaneous tetracyclic diterpenoids. C21H19NO7S Source: Sponge Xestospongia vansoesti (Palawan I., Philippines). Pharm: IDO (indoleamine 2,3- dioxygenase) inhibitor (IC50 = 4 μmol/L, a lead towards inhibitors of tumour immune escape). Ref: R. M. Centko, et al, Org. Lett., 2014, 16, 6480 O

S N H

O

O

O OH

O

OH

4 Sesterterpenoids 4.1 Acyclic Sesterterpenoids 353 Barangcadoic acid A Type: Acyclic sesterterpenoids. C25H40O4 [α]D28 = +34.9° (c = 3.8, CH2Cl2). Source: Sponge Hippospongia sp. Pharm: RCE-protease inhibitor. Ref: K. S. Craig, et al, Tet. Lett., 2002, 43, 4801

O

HO O

OH

354 Cacospongionolide D Type: Acyclic sesterterpenoids. C25H36O4 Waxy solid, [α]D = +17.7° (c = 0.2, CHCl3). Source: Sponge Fasciospongia cavernosa (Bay of Naples). Pharm: Toxic (brine shrimp); ichthyotoxin. Ref: S. De Rosa, et al, Nat. Prod. Lett., 1997, 10, 267

O

O O

HO

355 8,9-Dehydroircinin 1 Type: Acyclic sesterterpenoids. C25H28O5 Oil, [α]D = +94.2° (acetate). Source: Sponge Cacospongia scalaris. Pharm: Cell division inhibitor (fertilized starfish eggs). Ref: N. Fusetani, et al, Tet. Lett., 1984, 25, 4941 OH

O

O

O O

356 Demethylfurospongin 4 Type: Acyclic sesterterpenoids. C25H34O5 Oil. Source: Sponge Spongia officinalis (La Caleta, Cadiz, Spain). Pharm: Cytotoxic (P388, ED50 > 10 μg/mL). Ref: L. Garrido, et al, JNP, 1997, 60, 794

https://doi.org/10.1515/9783110655155-002

128

4 Sesterterpenoids

COOH

COOH

O

357 Fasciculatin Type: Acyclic sesterterpenoids. C25H34O4 Oil, [α]D = −15.6° (c = 0.5, CHCl3). Source: Sponges Ircinia fasciculata and Ianthella basta, nudibranch Dendrodoris grandiflora. Pharm: Inosine monophosphate dehydrogenase inhibitor. Ref: F. Cafieri, et al, Tetrahedron, 1972, 28, 1579│G. Alfano, et al, Experientia, 1979, 35, 1136│ G. Cimino, et al, Bull. Soc. Chim. Belg., 1980, 89, 1069│G. Cimino, et al, Tetrahedron, 1985, 41, 1093 OH

O

O O

358 Fasciculatin O-sulfate Type: Acyclic sesterterpenoids. C25H34O7S Amorph. solid, [α]D = −4.5° (c = 2.7, CHCl3). Source: Sponge Ircinia fasciculata. Pharm: Inosine monophosphate dehydrogenase inhibitor. Ref: S. De Rosa, et al, Nat. Prod. Lett., 1997, 10, 7 H O

O

O S

O

O

O O

359 Fasciospongide B Type: Acyclic sesterterpenoids. C25H36O7 Source: Sponge Fasciospongia sp. (New Caledonia). Pharm: PLA2 inhibitor; anti-inflammatory. Ref: A. Montagnac, et al, JNP, 1994, 57, 186

4.1 Acyclic Sesterterpenoids

129

O

O

HO

O

O O

HO

360 Fasciospongide C Type: Acyclic sesterterpenoids. C25H36O7 Source: Sponge Fasciospongia sp. (New Caledonia). Pharm: PLA2 inhibitor; anti-inflammatory. Ref: A. Montagnac, et al, JNP, 1994, 57, 186 OH O

O O

HO O

O

361 5-[13-(3-Furanyl)-2,6,10-trimethyl-3,5-tridecadienyl]-4-hydroxy-3-methyl-2 (5H)-furanone Type: Acyclic sesterterpenoids. C25H36O4 Oil, [α]D = −0.5° (c = 7.4, CHCl3). Source: Sponge Psammocinia sp. (Australia). Pharm: Antimicrobial. Ref: L. Murray, et al, Aust. J. Chem., 1995, 48, 1899 OH

O

O O

362 Furospinulosin 1 Type: Acyclic sesterterpenoids. C25H38O Oil. Source: Sponges Ircinia spinosula, Carteriospongia sp., Spongia idia, Thorecta sp. and Fasciospongia sp. Pharm: Ichthyotoxin. Ref: G. Cimino, et al, Tetrahedron, 1972, 28, 1315│S. Urban, et al, Aust. J. Chem., 1992, 45, 1255│P. A. Searle, et al, Tetrahedron, 1994, 50, 9893│CRC press, DNP on DVD, 2012, version 20.2

O

130

4 Sesterterpenoids

363 Furospongin 5 Type: Acyclic sesterterpenoids. C21H26O3 Oil. Source: Sponge Spongia officinalis (La Caleta, Cadiz, Spain). Pharm: Cytotoxic (P388, ED50 = 5 μg/mL). Ref: L. Garrido,et al, JNP, 1997, 60, 794

O O

O

364 (–)-Idiadione Type: Acyclic sesterterpenoids. C25H38O3 Oil, [α]D = −6.6° (c = 2.6, CHCl3). Source: Sponge Spongia idia. Pharm: Toxic (several predatory marine organisms: sea star, abalone larvae, brine shrimp). Ref: R. P. Walker, et al, JOC, 1980, 45, 4976│ Y. Noda, et al, Heterocycles, 2001, 55, 1839 O

O

O S

365 (S)-Ircinin 1 Type: Acyclic sesterterpenoids. C25H30O5 Oil, [α]D19.5 = −34.12° (MeOH). Source: Sponge Ircinia oros. Pharm: Antibiotic. Ref: G. Cimino, et al, Tetrahedron, 1972, 28, 333│R. J. Capon, et al, Nat. Prod. Lett., 1994, 4, 51 OH S

O

O

O O

366 (R)-Ircinin 1 Type: Acyclic sesterterpenoids. C25H30O5 Oil, [α]D25 = +32.3° (c = 0.05, MeOH). Source: Sponges Sarcotragus spp. (Cheju I., R. O. Korea). Pharm: Cytotoxic (A549, ED50 = 3.72 μg/mL; SK-OV-3, ED50 = 6.55 μg/mL; SK-MEL-2, ED50 = 8.95 μg/mL; XF498, ED50 = 5.42 μg/mL; HCT15, ED50 = 6.91 μg/mL; control Cisplatin: A549, ED50 = 0.72 μg/mL; SK-OV-3, ED50 = 1.23 μg/mL; SK-MEL-2, ED50 = 2.26 μg/mL; XF498, ED50 = 1.03 μg/mL; HCT15, ED50 = 1.10 μg/mL; control Doxorubicin: A549, ED50 = 0.02 μg/mL; SK-OV-3, ED50 = 0.11 μg/mL; SK-MEL-2, ED50 = 0.02 μg/mL; XF498, ED50 = 0.08 μg/mL; HCT15, ED50 = 0.04 μg/mL). Ref: Y. Liu, et al, JNP, 2001, 64, 1301

4.1 Acyclic Sesterterpenoids

OH

20Z

O

131

O

O

O

367 (S)-Ircinin 1 O-sulfate Type: Acyclic sesterterpenoids. C25H30O8S Amorph. Powder, [α]D = +9.5° (CHCl3). Source: Sponges Ircinia variabilis and Ircinia oros (Northern Adriatic Sea). Pharm: Ichthyotoxin; toxic (brine shrimp). Ref: S. De Rosa, et al, Nat. Prod. Lett., 1996, 8, 245

H

O

O S O

O

O

O

O

O

368 (S)-Ircinin 1 O-sulfate Δ11-isomer Type: Acyclic sesterterpenoids. C25H30O8S Amorph. Powder, [α]D = +9.5° (CHCl3). Source: Sponges Ircinia variabilis and Ircinia oros (Northern Adriatic Sea). Pharm: Ichthyotoxin; toxic (brine shrimp). Ref: S. De Rosa, et al, Nat. Prod. Lett., 1996, 8, 245

H

O

O S O

O

O 11Z

O

O

O

369 Ircinin 2 Type: Acyclic sesterterpenoids. C25H30O5 Oil, [α]D19.5 = −40.2° (MeOH). Source: Sponges Sarcotragus spp. (Cheju I., R. O. Korea), Ircinia oros and Ircinia spp. Pharm: Cytotoxic (A549, ED50 = 3.80 μg/mL; SK-OV-3, ED50 = 5.90 μg/mL; SK-MEL2, ED50 = 5.87 μg/mL; XF498, ED50 = 3.70 μg/mL; HCT15, ED50 = 4.74 μg/mL; control Cisplatin: A549, ED50 = 0.72 μg/mL; SK-OV-3, ED50 = 1.23 μg/mL; SK-MEL-2, ED50 = 2.26 μg/mL; XF498, ED50 = 1.03 μg/mL; HCT15, ED50 = 1.10 μg/mL; control Doxorubicin: A549, ED50 = 0.02 μg/mL; SK-OV-3, ED50 = 0.11 μg/mL; SK-MEL-2, ED50 = 0.02 μg/mL; XF498, ED50 = 0.08 μg/mL; HCT15, ED50 = 0.04 μg/mL); toxic

132

4 Sesterterpenoids

(brine shrimp). Ref: G. Cimino, et al, Tetrahedron, 1972, 28, 333│R. J. Capon, et al, Nat. Prod. Lett., 1994, 4, 51│Y. Liu, et al, JNP, 2001, 64, 1301

OH O

O O O

370 Isofasciculatin Type: Acyclic sesterterpenoids. C25H34O4 [α]D = −34.7° (acetate). Source: Sponge Cacospongia scalaris Pharm: Cell division inhibitor (fertilized starfish eggs). Ref: N. Fusetani, et al, Tet. Lett., 1984, 25, 4941 OH

O

O O

371 Isopalinurin Type: Acyclic sesterterpenoids. C25H34O4 Yellow oil, Source: Sponge Dysidea sp. (Bass Strait 145°30´E 39°20´S, Tasmania State, Australia). Pharm: Protein phosphatase inhibitor. Ref: L. Murray, et al, Aust. J. Chem., 1993, 48, 1291 OH

O

O O

372 Luffarin Q Type: Acyclic sesterterpenoids. C25H38O2 Oil. Source: Sponges Luffariella geometrica (Australia) and Thorecta horridus. Pharm: Anti-inflammatory. Ref: E. Fattorusso, et al, BoMCL, 1991, 1, 639│M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705 O O

4.1 Acyclic Sesterterpenoids

133

373 Okinonellin B Type: Acyclic sesterterpenoids. C25H36O4 Oil, [α]D20 = +17.9° (c = 0.15, EtOH). Source: Sponge Spongionella sp. Pharm: Cell division inhibitor (starfish embryos); cytotoxic. Ref: Y. Kato, et al, Experientia, 1986, 42, 1299│W. D. Schmitz, et al, JOC, 1998, 63, 2058 OH 21

8

23

O

O

O

374 Palinurin Type: Acyclic sesterterpenoids. C25H34O4 Oil, [α]D = +45.3° (CHCl3). Source: Sponge Ircinia variabilis. Pharm: ACE inhibitor; aldose reductase inhibitor. Ref: G. Alfano, et al, Experientia, 1979, 35, 1136 OH

O

O

O

375 Sarcotin A Type: Acyclic sesterterpenoids. C25H34O4 Source: Sponges Sarcotragus spp. (Cheju I., R. O. Korea). Pharm: Cytotoxic (A549, ED50 = 29.70 μg/mL; SK-OV-3, ED50 = 22.06 μg/mL; SK-MEL-2, ED50 > 30.00 μg/mL; XF498, ED50 = 24.83 μg/mL; HCT15, ED50 = 27.18 μg/mL; control Cisplatin: A549, ED50 = 0.72 μg/mL; SKOV-3, ED50 = 1.23 μg/mL; SK-MEL-2, ED50 = 2.26 μg/mL; XF498, ED50 = 1.03 μg/mL; HCT15, ED50 = 1.10 μg/mL; control Doxorubicin: A549, ED50 = 0.02 μg/mL; SKOV-3, ED50 = 0.11 μg/mL; SK-MEL-2, ED50 = 0.02 μg/mL; XF498, ED50 = 0.08 μg/mL; HCT15, ED50 = 0.04 μg/mL). Ref: Y. Liu, et al, JNP, 2001, 64, 1301 OH O O O

376 Sarcotin B Type: Acyclic sesterterpenoids. C25H34O4 Oil. Source: Sponges Sarcotragus spp. (Cheju I., R. O. Korea). Pharm: Cytotoxic (A549, ED50 = 10.10 μg/mL; SK-OV-3,

134

4 Sesterterpenoids

ED50 = 11.30 μg/mL; SK-MEL-2, ED50 = 7.78 μg/mL; XF498, ED50 = 8.89 μg/mL; HCT15, ED50 = 8.95 μg/mL; control Cisplatin: A549, ED50 = 0.72 μg/mL; SK-OV-3, ED50 = 1.23 μg/mL; SK-MEL-2, ED50 = 2.26 μg/mL; XF498, ED50 = 1.03 μg/mL; HCT15, ED50 = 1.10 μg/mL; control Doxorubicin: A549, ED50 = 0.02 μg/mL; SK-OV-3, ED50 = 0.11 μg/mL; SK-MEL-2, ED50 = 0.02 μg/mL; XF498, ED50 = 0.08 μg/mL; HCT15, ED50 = 0.04 μg/mL). Ref: Y. Liu, et al, JNP, 2001, 64, 1301 HO O

O

O

377 Sarcotin C Type: Acyclic sesterterpenoids. C25H34O4 Oil. Source: Sponges Sarcotragus spp. (Cheju I., R. O. Korea). Pharm: Cytotoxic (A549, ED50 = 16.89 μg/mL; SK-OV-3, ED50 = 26.84 μg/mL; SK-MEL-2, ED50 = 16.31 μg/mL; XF498, ED50 = 20.40 μg/mL; HCT15, ED50 = 27.49 μg/mL; control Cisplatin: A549, ED50 = 0.72 μg/mL; SK-OV-3, ED50 = 1.23 μg/mL; SK-MEL-2, ED50 = 2.26 μg/mL; XF498, ED50 = 1.03 μg/mL; HCT15, ED50 = 1.10 μg/mL; control Doxorubicin: A549, ED50 = 0.02 μg/mL; SK-OV-3, ED50 = 0.11 μg/mL; SK-MEL-2, ED50 = 0.02 μg/mL; XF498, ED50 = 0.08 μg/mL; HCT15, ED50 = 0.04 μg/mL). Ref: Y. Liu, et al, JNP, 2001, 64, 1301 OH O O O

378 Sarcotin D Type: Acyclic sesterterpenoids. C25H30O5 Oil, [α]D25 = +36.1° (c = 0.05, MeOH). Source: Sponges Sarcotragus spp. (Cheju I., R. O. Korea). Pharm: Cytotoxic (A549, ED50 = 4.98 μg/mL; SK-OV-3, ED50 = 9.39 μg/mL; SK-MEL-2, ED50 = 10.18 μg/mL; XF498, ED50 = 6.52 μg/mL; HCT15, ED50 = 9.82 μg/mL; control Cisplatin: A549, ED50 = 0.72 μg/mL; SK-OV-3, ED50 = 1.23 μg/mL; SK-MEL-2, ED50 = 2.26 μg/mL; XF498, ED50 = 1.03 μg/mL; HCT15, ED50 = 1.10 μg/mL; control Doxorubicin: A549, ED50 = 0.02 μg/mL; SK-OV-3, ED50 = 0.11 μg/mL; SK-MEL-2, ED50 = 0.02 μg/mL; XF498, ED50 = 0.08 μg/mL; HCT15, ED50 = 0.04 μg/mL). Ref: Y. Liu, et al, JNP, 2001, 64, 1301

4.2 Noracyclic Sesterterpenoids

20E

O

O

O

135

O

HO

379 Sarcotin E Type: Acyclic sesterterpenoids. C25H30O5 Oil, [α]D25 = +41.6° (c = 0.06, MeOH). Source: Sponges Sarcotragus spp. (Cheju I., R. O. Korea). Pharm: Cytotoxic (A549, ED50 = 3.80 μg/mL; SK-OV-3, ED50 = 6.24 μg/mL; SK-MEL-2, ED50 = 8.37 μg/mL; XF498, ED50 = 5.00 μg/mL; HCT15, ED50 = 7.31 μg/mL; control Cisplatin: A549, ED50 = 0.72 μg/mL; SK-OV-3, ED50 = 1.23 μg/mL; SK-MEL-2, ED50 = 2.26 μg/mL; XF498, ED50 = 1.03 μg/mL; HCT15, ED50 = 1.10 μg/mL; control Doxorubicin: A549, ED50 = 0.02 μg/mL; SK-OV-3, ED50 = 0.11 μg/mL; SK-MEL-2, ED50 = 0.02 μg/mL; XF498, ED50 = 0.08 μg/mL; HCT15, ED50 = 0.04 μg/mL). Ref: Y. Liu, et al, JNP, 2001, 64, 1301 20E

O

O

HO O

O

380 Thorectolide-25-acetate Type: Acyclic sesterterpenoids. C27H38O6 [α]D = +33.8° (c = 0.49, CHCl3). Source: Sponge Hyrtios sp. (New Caledonia). Pharm: Cytotoxic (KB, IC50 = 0.3 μg/mL); cobra venom PLA2 inhibitor. Ref: M. -L. Bourguet-Kondracki, et al, J. Chem. Res. (S), 1996, 192 O O HO

O

O O

4.2 Noracyclic Sesterterpenoids 381 Aikupikoxide A Muqubilone Type: Noracyclic sesterterpenoids. C24H40O6 Oil, [α]D25 = +48° (c = 0.1, CHCl3), [α]D = +81° (c = 0.8, CH2Cl2). Source: Sponges Diacarnus erythraenus (Red Sea) and Diacarnus erythraeanus. Pharm: Antiviral (HSV-1, ED50 = 30 μg/

136

4 Sesterterpenoids

mL); cytotoxic (P388 ATCC: CCL46, A549 ATCC: CCL8 and HT29 ATCC: HTB38 cells, IC50 > 1 μg/mL); cytotoxic (Vero, IC50 = 60.0 μg/mL). Ref: K. A. El Sayed, et al, JNP, 2001, 64, 522│D. T. A. Youssef, et al, JNP, 2001, 64, 1332. O O

O

OH O

O

382 Cacospongienone A Type: Noracyclic sesterterpenoids. C21H28O3 Oil. Source: Sponge Cacospongia scalaris. Pharm: Cytotoxic; antimicrobial; anti-inflammatory. Ref: G. Guella, et al, Helv. Chim. Acta, 1986, 69, 726│S. Da Rosa, et al, JNP, 1995, 58, 1776 O

O

O

383 Cacospongienone B Type: Noracyclic sesterterpenoids. C21H28O3 Oil. Source: Sponge Cacospongia scalaris. Pharm: Cytotoxic; antimicrobial; anti-inflammatory. Ref: G. Guella, et al, Helv. Chim. Acta, 1986, 69, 726│S. Da Rosa, et al, JNP, 1995, 58, 1776

O

O

O

384 Cyclofurospongin 2 Type: Noracyclic sesterterpenoids. C21H26O3 Oil, [α]D25 = −6.0° (c = 1.0, CHCl3). Source: Sponge Spongia officinalis (La Caleta, Cadiz, Spain). Pharm: Cytotoxic (P388, ED50 > 10 μg/mL). Ref: L. Garrido,et al, JNP, 1997, 60, 794

O

O

O

385 1,11-Di-3-furanyl-4,8-dimethyl-1,4,8-undecatrien-6-ol Type: Noracyclic sesterterpenoids. C21H26O3 [α]D25 = +21.8° (c = 0.78, CHCl3). Source: Sponge Spongis virgultosa (Spain). Pharm: Vasodilator (coronary). Ref: A. Fontana, et al, JNP, 1996, 59, 869

4.2 Noracyclic Sesterterpenoids

O

OH

137

O

386 Furospongin 2 Type: Noracyclic sesterterpenoids. C21H26O3 Oil. Source: Sponges Spongia officinalis (La Caleta, Cadiz, Spain) and Hippospongia communis. Pharm: Toxic (brine shrimp). Ref: G. Cimino, et al, Tetrahedron, 1972, 28, 267│L. Garrido,et al, JNP, 1997, 60, 794 12E

O

O

O

387 Furospongolide Type: Noracyclic sesterterpenoids. C21H28O3 Oil. Source: Sponges Dysidea herbacea and Lendenfeldia sp. Pharm: Antifoulant. Ref: Y. Kashman, et al, Experientia, 1980, 36, 1279 O O

O

388 Irciformonin I Type: Noracyclic sesterterpenoids. C23H34O5 Powder, [α]D25 = +2.3° (c = 7.8, CH2Cl2). Source: Sponge Ircinia formosana (Taiwan waters). Pharm: Inhibits cell proliferation (peripheral blood mononuclear cells). Ref: Y. -C. Shen, et al, Helv. Chim. Acta, 2009, 92, 2101

O

O

OH

O

O

389 ent-(–)-Muqubilone Type: Noracyclic sesterterpenoids. C24H40O6 Source: Sponge Diacarnus bismarckensis (Sanaroa, Papua New Guinea). Pharm: Antitrypanosomal (Trypanosoma brucei, African sleeping sickness). Ref: B. K. Rubio, et al, JNP, 2009, 72, 218

138

4 Sesterterpenoids

H 6

O

O

OH

2

3

O

O

O

390 (+)-Muqubilone B Type: Noracyclic sesterterpenoids. C24H40O6 Oil, [α]D28 = +59.5° (c = 0.046, CHCl3). Source: Sponge Diacarnus bismarckensis (Sanaroa, Papua New Guinea). Pharm: Antitrypanosomal (Trypanosoma brucei, African sleeping sickness). Ref: B. K. Rubio, et al, JNP, 2009, 72, 218 H

O

OH

2

3

6

O

O

O

O

391 Rhopaloic acid A Type: Noracyclic sesterterpenoids. C24H38O3 Oil, [α]D25 = +40° (c = 0.47, CHCl3). Source: Sponge Rhopaloeides sp. (Japan waters). Pharm: Cytotoxic (in vitro: K562, IC50 = 0.1 μg/mL, Molt4, IC50 = 0.1 μg/mL, L1210, IC50 = 0.1 μg/mL); inhibits gastrulation of sea star embryos. Ref: S. Ohta, et al, Tetrahedron. Lett., 1996, 37, 2265│R. Takagi, et al, JCS Perkin I, 1998, 925

OH

O O

392 Rhopaloic acid B Type: Noracyclic sesterterpenoids. C24H38O3 Oil, [α]D25 = +55° (c = 0.23, CHCl3). Source: Sponge Rhopaloeides sp. (Japan waters). Pharm: Inhibits gastrulation of sea star embryo (Asterina pectinifera). Ref: M. Yanai, et al, Tetrahedron, 1998, 54, 15607

4.2 Noracyclic Sesterterpenoids

139

OH

O 6

O 5

393 Rhopaloic acid C Type: Noracyclic sesterterpenoids. C24H36O3 Oil, [α]D25 = +84° (c = 0.03, CHCl3). Source: Sponge Rhopaloeides sp. (Japan waters). Pharm: Inhibits gastrulation of sea star embryo (Asterina pectinifera). Ref: M. Yanai, et al, Tetrahedron, 1998, 54, 15607

OH

O 6

O 5

394 Untenic acid Type: Noracyclic sesterterpenoids. C21H28O3 Oil, [α]D25 = +1.6° (c = 10.5, CHCl3). Source: An unidentified sponge (family Halichondriidae). Pharm: Ca2+-ATPase activator. Ref: N. Shoji, et al, Aust. J. Chem., 1992, 45, 793

O

O

OH

395 Untenospongin B Type: Noracyclic sesterterpenoids. C21H26O3 Oil, [α]D = −20.1° (c = 1.02, CHCl3); [α]D25 = −1.5° (c = 2.7, CHCl3). Source: Sponge Hippospongia sp. (Okinawa). Pharm: Coronary vasodilator. Ref: A. Umeyama, et al, Aust. J. Chem., 1989, 42, 459│ J. Kobayashi, et al, CPB, 1993, 41, 381

O

OH

O

396 Untenospongin C Type: Noracyclic sesterterpenoids. C21H26O3 Oil, [α]D20 = −9.3° (c = 1, CHCl3). Source: Sponge Hippospongia sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 3.8 μg/mL). Ref: J. Kobayashi, et al, CPB, 1993, 41, 381

140

O

4 Sesterterpenoids

O

O

4.3 Cyclohexane Sesterterpenoids 397 (Z)-24-Acetoxyneomanoalide Type: Cyclohexane sesterterpenoids. C27H40O5 Oil, [α]D25 = −16.4° (c = 0.14, CHCl3). Source: Sponge Luffariella sp. (yield = 0.004% frw, depth of 4–10 m, north side of Pelorus I., 146°29‘E 18°34‘S, Great Barrier Reef, Australia). Pharm: Antibacterial (TLC bioautographic assay, Escherichia coli, Bacillus subtilis and Micrococcus luteus, significant activities). Ref: G. M. König, et al, JNP, 1992, 55, 174 O O

OH

O O

398 4-Acetoxy-thorectidaeolide A Type: Cyclohexane sesterterpenoids. C27H38O5 Source: Sponge Hyrtios communis (Northern Reef region, Palau). Pharm: HIF-1 (Hypoxia Inducible Factor-1) inhibitor. Ref: J. Li, et al, JNP, 2013, 76, 1492 O O

O O O

399 (Z)-24-Acetyl-2,3-dihydroneomanoalide Type: Cyclohexane sesterterpenoids. C27H42O5 Oil, [α]D25 = +11° (c = 0.1, CHCl3). Source: Sponge Luffariella sp. (yield = 0.0005% frw, depth of 4–10 m, north side of Pelorus I., 146°29‘E 18°34‘S, Great Barrier Reef, Australia). Pharm: Antibacterial (TLC bioautographic assay, Escherichia coli, Bacillus subtilis and Micrococcus luteus, significant activities). Ref: G. M. König, et al, JNP, 1992, 55, 174

4.3 Cyclohexane Sesterterpenoids

141

O O

O

OH

O

400 Alotaketal A Type: Cyclohexane sesterterpenoids. C25H34O4 Amorph. solid, [α]D25 = −38.9° (c = 0.01, MeOH). Source: Sponge Hamigera sp. (Milne Bay, Papua New Guinea). Pharm: Activator of cAMP signaling pathway (HEK-293 cells in absence of hormone binding, EC50 = 0.018 μmol/L). Ref: R. Forestieri, et al, Org. Lett., 2009, 11, 5166│ J. Daoust, et al, Org. Lett., 2010, 12, 3208

H

O

O

O

H OH

401 Cyclolinteinol Type: Cyclohexane sesterterpenoids. C25H36O4 [α]D25 = +63° (c = 0.03, CHCl3). Source: Sponge Cacospongia cf. linteiformis (Caribbean Sea). Pharm: Macrophage activation inhibitor. Ref: A. Carotenuto, et al, Tetrahedron, 1997, 53, 7305 O

OH O O

402 Cyclolinteinol acetate Type: Cyclohexane sesterterpenoids. C27H38O5 [α]D25 = +61° (c = 0.003, CHCl3). Source: Sponge Cacospongia cf. linteiformis (Caribbean Sea). Pharm: Macrophage activation inhibitor. Ref: A. Carotenuto, et al, Tetrahedron, 1997, 53, 7305

142

4 Sesterterpenoids

O O

O O O

403 Cyclolinteinone Type: Cyclohexane sesterterpenoids. C25H36O3 Oil, [α]D25 = +53° (c = 0.04, CHCl3). Source: Sponge Cacospongia linteiformis (Bahamas). Pharm: Ichthyotoxic (mosquito fish Gambusia affinis, 10 ppm); Antifeedant (fish Carassius auratus, 30 μg/cm2 of food pellets, high feeding deterrence); NO (nitrogen oxide) generation inhibitor; anti-inflammatory; macrophage activation modulator; INOS and COX-2 expression regulator. Ref: M. R. Conte, et al, Tetrahedron, 1994, 50, 13469│A. Carotenuto, et al, Tetrahedron, 1997, 53, 7305│D‘Acquisto, et al, Biochem. J., 2000, 346, 793 O O O

404 16-Deoxoisodehydroluffariellolide 3-[4,8-Dimethyl-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7-decadienyl]-2(5H)-furanone Type: Cyclohexane sesterterpenoids. C25H38O2 Light yellow oil. Source: Sponge Hyrtios cf. erecta. Pharm: Antifungal (Ustilago violacea, 50 μg, 2 mm growth inhibition zone). Ref: G. Kirsch, et al, JNP, 2000, 63, 825 O O

405 (Z)-2,3-Dihydroneomanoalide Type: Cyclohexane sesterterpenoids. C25H40O4 Oil, [α]D25 = +2.5° (c = 0.44, CHCl3). Source: Sponge Luffariella sp. (yield = 0.002% frw, depth of 4–10 m, north side of Pelorus I., 146°29‘E 18°34‘S, Great Barrier Reef, Australia). Pharm: Antibacterial (TLC bioautographic assay, Escherichia coli, Bacillus subtilis and Micrococcus luteus, significant activities). Ref: G. M. König, et al, JNP, 1992, 55, 174

4.3 Cyclohexane Sesterterpenoids

143

O O H OH

OH

406 Fasciospongide A Type: Cyclohexane sesterterpenoids. C25H34O6 Oil, [α]D = +46° (c = 1, CHCl3). Source: Sponge Fasciospongia sp. (New Caledonia). Pharm: PLA2 inhibitor; antiinflammatory. Ref: A. Montagnac, et al, JNP, 1994, 57, 186 O

HO

O

O HO

O

407 Hippospongin Type: Cyclohexane sesterterpenoids. C25H32O4 Oil, [α]D25 = +15° (c = 5.4, CHCl3). Source: Sponge Hippospongia sp. Pharm: Antispasmodic; antibacterial (grampositive bacteria). Ref: J. Kobayashi, et al, Tet. Lett., 1986, 27, 2113HO O O

O

408 3-Hydroxy-4,6-dimethyl-6-(2-methyl-10-phenyl-9-decenyl)-1,2-dioxan-3acetic acid Type: Cyclohexane sesterterpenoids. C25H38O5 Oil, [α]D28 = +42° (c = 0.6, CHCl3). Source: Sponge Plakortis sp. (Orote Peninsula, Guam). Pharm: Antibacterial (Staphylococcus aureus, weak). Ref: E. Manzo, et al, JNP, 2009, 72, 1547 OH COOH 6

O

O

409 3-Hydroxy-4,6-dimethyl-6-(2-methyl-10-phenyldecyl)-1,2-dioxan-3-acetic acid Type: Cyclohexane sesterterpenoids. C25H40O5 Oil, [α]D28 = +23° (c = 0.4, CHCl3). Source: Sponge Plakortis sp. (Orote Peninsula, Guam). Pharm: Antibacterial (Staphylococcus aureus, weak). Ref: E. Manzo, et al, JNP, 2009, 72, 1547

144

4 Sesterterpenoids

OH 3

4 6

O 6

COOH

O

410 3-Hydroxy-3,4,6-trimethyl-6-(2-methyl-10-phenyl-9-decenyl)-1,2-dioxane Type: Cyclohexane sesterterpenoids. C24H38O3 Source: Sponge Plakortis sp. (Orote Peninsula, Guam). Pharm: Antibacterial (Staphylococcus aureus, weak). Ref: E. Manzo, et al, JNP, 2009, 72, 1547 OH

6

O

O

411 3-Hydroxy-3,4,6-trimethyl-6-(2-methyl-10-phenyldecyl)-1,2-dioxane Type: Cyclohexane sesterterpenoids. C24H40O3 Source: Sponge Plakortis sp. (Orote Peninsula, Guam). Pharm: Antibacterial (Staphylococcus aureus, weak). Ref: E. Manzo, et al, JNP, 2009, 72, 1547 OH

6

O

O

412 Isodehydroluffariellolide Type: Cyclohexane sesterterpenoids. C25H36O3 Colorless oil. Source: Sponges Hyrtios cf. erecta and Fascaplysinopsis reticulata. Pharm: p56lck Tyrosine kinase inhibitor (0.5 mmol/L, reduced activity to 45%). Ref: C. Jimènez, et al, JOC, 1991, 56, 3403│ G. Kirsch, et al, JNP, 2000, 63, 825 O O O

413 Luffariellolide Type: Cyclohexane sesterterpenoids. C25H38O3 Oil. Source: sponges Luffariella sp., Cacospongia sp. and Fascaplysinopsis reticulata. Pharm: PLA2 inhibitor (potent; since PLA2 is linked to initial step in cascade of enzymatic reactions that lead to

4.3 Cyclohexane Sesterterpenoids

145

generation of inflammatory mediators, specific inhibitors of PLA2 have been considered as potential drugs for treatment of inflammation and related diseases). Ref: K. F. Albizati, et al, Experientia, 1987, 43,│949│B. C. M. Potts, et al, JACS, 1992, 114, 5093│M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39

O HO

O

414 Luffariolide A Type: Cyclohexane sesterterpenoids. C25H36O3 Colorless oil. Source: Sponge Luffariella sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 1.1 μg/mL). Ref: M. Tsuda, et al, JOC, 1992, 57, 3503 O

O

OH

415 Luffariolide B Type: Cyclohexane sesterterpenoids. C25H38O4 Colorless oil, [α]D25 = +20° (c = 1.0, CHCl3). Source: Sponge Luffariella sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 1.3 μg/mL). Ref: M. Tsuda, et al, JOC, 1992, 57, 3503

6

OH 4

OH

O O

416 Luffariolide C Type: Cyclohexane sesterterpenoids. C25H40O4 Colorless oil, [α]D25 = +4.4° (c = 1.6, CHCl3). Source: Sponge Luffariella sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 7.8 μg/mL). Ref: M. Tsuda, et al, JOC, 1992, 57, 3503

146

4 Sesterterpenoids

O O H OH

OH

417 Luffariolide D Type: Cyclohexane sesterterpenoids. C25H38O4 Colorless oil, [α]D20 = +9.0° (c = 0.15, CHCl3). Source: Sponge Luffariella sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 4.2 μg/mL). Ref: M. Tsuda, et al, JOC, 1992, 57, 3503

H HO

O

O

H O

418 Luffariolide E Type: Cyclohexane sesterterpenoids. C25H36O4 Colorless oil, [α]D17 = +7.1° (c = 0.42, CHCl3). Source: Sponge Luffariella sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 1.2 μg/mL). Ref: M. Tsuda, et al, JOC, 1992, 57, 3503│G. Hareau-Vittini, et al, Synthesis, 1995, 1007│G. Hareau-Vittini, et al, Synlett., 1995, 893

H O

O

O

H O

419 Manoalide Type: Cyclohexane sesterterpenoids. C25H36O5 Amorph. Source: Sponges Luffariella variabilis (polejaeff), Smenospongia sp. and Hyrtios erecta. Pharm: PLA2 inhibitor (potent; since PLA2 is linked to initial step in cascade of enzymatic reactions that lead to generation of inflammatory mediators, specific inhibitors of PLA2 have been considered as potential drugs for treatment of inflammation and related diseases); anti-inflammatory; antibacterial (Streptomyces pyogenes, Staphylococcus aureus; in vitro); cytotoxic; antipsoriatic; analgesic; ornithine decarboxylase inhibitor. Ref: E. D. De Silva, et al, Tet. Lett., 1980, 1611; 1981, 22, 3147│E. S. Burley, et al, Pharmacologist, 1982, 24, 117│L. A. Blankemeier, et al, Fed. Proc., 1983, 42, 374│R. S. Jacobs, et al, Tetrahedron, 1985, 41, 981│P. Bury, et al, Tetrahedron, 1994, 50, 8793│J. Coombs, et al, Synthesis, 1998, 1367│A. Soriente, et al, Tetrahedron:

4.3 Cyclohexane Sesterterpenoids

147

Asymmetry, 1999, 10, 4481│M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39│C. A. Motti, et al, Mar. Drugs, 2010, 8, 190

24

HO

O

O

H

O

HO

420 13R,16R,17R-Muqubilin A epi-Muqubilin A Type: Cyclohexane sesterterpenoids. C24H40O4 Yellow oil, [α]D = +61.7° (c = 0.7, CHCl3). Source: Sponges Diacarnus cf. spinopoculum (Solomon Is. and Papua New Guinea) and Diacarnus erythraenus (Red Sea). Pharm: Antimalarial (Plasmodium falciparum D6, IC50 = 2900 ng/mL, SI > 1.6; Plasmodium falciparum W2, IC50 > 4760 ng/mL, SI > 1.0); antiviral (HSV-1, ED50 = 7.5 μg/mL); antitoxoplasma (Toxoplasma gondii, 0.1 μmol/L, without significant toxicity); cytotoxic (Vero, IC50 = 30.0 μg/mL); cytotoxic (HL60 (KB), Molt4, KM12, IGROV1, all GI50 > 5.0 μmol/L); differential cytotoxicity (softagar assay, 50 μg/disk, zone differential of 250 units is expected for “selectiveactivity”, M17-L1210, 20 zone differential units). Ref: S. Sperry, et al, JNP, 1998, 61, 241│K. A. El Sayed, et al, JNP, 2001, 64, 522 H 16R 13R

O

O

O

17R

OH

421 13R,16S,17R-Muqubilin A ent-Muqubilin Type: Cyclohexane sesterterpenoids. C24H40O4 Yellow oil, [α]D = −35.6° (c = 9.8, CHCl3). Source: Sponge Diacarnus cf. spinopoculum (Solomon Is. and Papua New Guinea). Pharm: Differential cytotoxicity (softagar assay, 50 μg/disk, zone differential of 250 units is expected for “selectiveactivity”, C38-L1210, -50 zone differential units; M17-L1210, -30 zone differential units); cytotoxic (HL60 (KB), GI50 = 1.77 μmol/L; Molt4, GI50 > 5.0 μmol/L; A549/ATCC, GI50 > 5.0 μmol/L; KM12, GI50 > 5.0 μmol/L; LOX-IMVI, GI50 = 2.17 μmol/L; IGROV1, GI50 = 1.11 μmol/L; 786-0, GI50 > 5.0 μmol/L; BT-549, GI50 > 5.0 μmol/L). Ref: S. Sperry, et al, JNP, 1998, 61, 241│M. D‘Ambrosio, et al, Helv. Chim. Acta, 1998, 81, 1285

148

4 Sesterterpenoids

H 13R

O

17R

OH

16S

O

O

422 13S,16R,17S-Muqubilin A Type: Cyclohexane sesterterpenoids. C24H40O4 Yellow oil, [α]D = +31.6° (c = 0.18, CHCl3). Source: Sponge Prianos sp. (Red Sea). Pharm: Antimicrobial; cytotoxic. Ref: Y. Kashman, et al, Tet. Lett., 1979, 1707│L, V. Manes, et al, Tet. Lett., 1984, 25, 931│R. J. Capon, et al, Tetrahedron, 1985, 41, 3391 H 13S

O

17S

OH

16R

O

O

423 Muqubilin B Type: Cyclohexane sesterterpenoids. C25H42O5 Oil, [α]D = −15.5° (c = 0.54, CHCl3). Source: Sponge Diacarnus cf. spinopoculum (Solomon Is. and Papua New Guinea). Pharm: Cytotoxic (HL60(KB), GI50 > 5.0 μmol/L; Molt4, GI50 > 5.0 μmol/L; A549/ATCC, GI50 > 5.0 μmol/L; KM12, GI50 > 5.0 μmol/L; IGROV1, GI50 = 2.42 μmol/L; 786-0, GI50 > 5.0 μmol/L). Ref: S. Sperry, et al, JNP, 1998, 61, 241 H OH

13R

O

17R

O

16S

O

O

424 (6E)-Neomanoalid-24-al Type: Cyclohexane sesterterpenoids. C25H36O4 Oil, [α]D25 = −10.6° (c = 0.18, CHCl3). Source: Sponge Luffariella sp. (yield = 0.004% frw, depth of 4–10 m, north side of Pelorus I., 146°29‘E 18°34‘S, Great Barrier Reef, Australia), Pharm: Antibacterial (TLC bioautographic assay, Escherichia coli, Bacillus subtilis and Micrococcus luteus, significant activities); molluscicide. Ref: G. M. König, et al, JNP, 1992, 55, 174

4.3 Cyclohexane Sesterterpenoids

149

O O

OH O

425 (6Z)-Neomanoalide Type: Cyclohexane sesterterpenoids. C25H38O4 Glass, [α]D = −27.8° (c = 0.79, CH2Cl2). Source: Sponges Luffariella sp. (yield = 0.016% frw, depth of 4–10 m, north side of Pelorus I., 146°29‘E 18°34‘S, Great Barrier Reef, Australia), Luffariella variabilis and Hyrtios erecta. Pharm: Antibacterial (gram-positive bacteria Bacillus subtilis and Staphylococcus aureus); antipsoriatic; ornithine decarboxylase inhibitor. Ref: E. D. de Silva, et al, Tet. Lett., 1981, 22, 3147│M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705│G. M. König., et al, JNP, 1992, 55, 174 O O

6Z

OH

OH

426 (6E)-Neomanoalide Type: Cyclohexane sesterterpenoids. C25H38O4 Glass, [α]D = −25.9° (c = 0.54, CH2Cl2). Source: Sponges Luffariella sp. (yield = 0.024% frw, depth of 4–10 m, north side of Pelorus I., 146°29‘E 18°34‘S, Great Barrier Reef, Australia), Luffariella variabilis and Hyrtios erecta. Pharm: Antibacterial (gram-positive bacteria Bacillus subtilis and Staphylococcus aureus); antipsoriatic; ornithine decarboxylase inhibitor. Ref: E. D. de Silva, et al, Tet. Lett., 1981, 22, 3147│M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705│G. M. König, et al, JNP, 1992, 55, 174 O O 2

H 6E

3

OH

OH

427 Phorbaketal A Type: Cyclohexane sesterterpenoids. C25H34O4 Oil, [α]D25 = −118.1° (c = 0.15, MeOH). Source: Sponge Phorbas sp. (Gageo I., R. O. Korea). Pharm: Cytotoxic (MTT assay,

150

4 Sesterterpenoids

HT29, IC50 = 12 μg/mL; HepG2, IC50 = 11.2 μg/mL; A549, IC50 = 11 μg/mL). Ref: J. -R. Rho, et al, Org. Lett., 2009, 11, 5590 OH H

O

O

H

O

428 Phorbaketal B Type: Cyclohexane sesterterpenoids. C25H36O4 Oil, [α]D25 = −115.1° (c = 0.1, MeOH). Source: Sponge Phorbas sp. (Gageo I., R. O. Korea). Pharm: Cytotoxic (MTT assay, HT29, IC50 = 27.9 μg/mL; HepG2, IC50 = 14.8 μg/mL; A549, IC50 = 565 μg/mL). Ref: J. -R. Rho, et al, Org. Lett., 2009, 11, 5590 OH H

OH

H O

H

O

429 Phorbaketal C Type: Cyclohexane sesterterpenoids. C25H36O4 Oil, [α]D25 = −122.3° (c = 0.1, MeOH). Source: Sponge Phorbas sp. (Gageo I., R. O. Korea). Pharm: Cytotoxic (MTT assay, HT29, IC50 = 212 μg/mL; HepG2, IC50 = 11.8 μg/mL; A549, IC50 = 12.4 μg/mL). Ref: J. -R. Rho, et al, Org. Lett., 2009, 11, 5590 OH HO

H

H O

H

O

430 Phorbaketal H Type: Cyclohexane sesterterpenoids. C25H34O4 Source: Sponge Monanchora sp. (Gageo I., R. O. Korea). Pharm: Cytotoxic (A498, weak). Ref: W. Wang, et al, JNP, 2013, 76, 170

4.3 Cyclohexane Sesterterpenoids

H

151

O

H

HO

O O

431 Phorbaketal I Type: Cyclohexane sesterterpenoids. C25H32O4 Source: Sponge Monanchora sp. (Gageo I., R. O. Korea). Pharm: Cytotoxic (A498, weak). Ref: W. Wang, et al, JNP, 2013, 76, 170 O

H O

H O O

432 Secomanoalide Type: Cyclohexane sesterterpenoids. C25H36O5 Glass, [α]D = +16.2° (c = 0.99, CHCl3). Source: Sponge Luffariella variabilis. Pharm: Antibacterial (gram-positive bacteria Bacillus subtilis and Staphylococcus aureus). Ref: E. D. de Silva, et al, Tet. Lett., 1981, 22, 3147 OH O HO

O

O

433 Thorectidaeolide A Type: Cyclohexane sesterterpenoids. C25H36O4 Source: Sponge Hyrtios communis (Northern Reef region, Palau). Pharm: HIF-1 (Hypoxia Inducible Factor-1) inhibitor. Ref: J. Li, et al, JNP, 2013, 76, 1492

152

4 Sesterterpenoids

O O

O OH

434 Thorectidaeolide B Type: Cyclohexane sesterterpenoids. C25H36O4 Source: Sponge Hyrtios communis (Northern Reef region, Palau). Pharm: HIF-1 (Hypoxia Inducible Factor-1) inhibitor. Ref: J. Li, et al, JNP, 2013, 76, 1492 HO

O O

O

4.4 Bicyclic Sesterterpenoids 435 Bilosespene A Type: Bicyclic sesterterpenoids. C25H40O2 Source: Sponge Dysidea cinerea (Dahlak archipelago, Eritrea). Pharm: Cytotoxic (mixture with Bilosespene B: P388, A549, HT29 and MEL28, IC50 = 2.5 μg/mL). Ref: A. Rudi, et al, Org. Lett., 1999, 1, 471 COOH

H

436 Bilosespene B Type: Bicyclic sesterterpenoids. C25H40O2 Source: Sponge Dysidea cinerea (Dahlak archipelago, Eritrea). Pharm: Cytotoxic (mixture with Bilosespene A: P388, A549, HT29 and MEL28, IC50 = 2.5 μg/mL). Ref: A. Rudi, et al, Org. Lett., 1999, 1, 471

4.4 Bicyclic Sesterterpenoids

153

COOH

H

437 Cladocoran A Type: Bicyclic sesterterpenoids. C27H40O5 Pale yellow oil, [α]D20 = −25.8° (c = 0.4, MeOH). Source: Stony coral Cladocora cespitosa (Mediterranean Sea). Pharm: Antiinflammatory (inhibits secretory PLA2, IC50 = 0.8–1.9 μmol/L). Ref: A. Fontana, et al, JOC, 1998, 63, 2845│H. Miyaoka, et al, JOC, 2003, 68, 3476 (Stereochem. revised). HO

O

18

H

O

O O

438 Cladocoran B Type: Bicyclic sesterterpenoids. C25H38O4 Pale yellow oil, [α]D20 = −59.9° (c = 0.6, MeOH). Source: Stony coral Cladocora cespitosa (Mediterranean Sea). Pharm: Anti-inflammatory (inhibits secretory PLA2, IC50 = 0.8–1.9 μmol/L). Ref: A. Fontana, et al, JOC, 1998, 63, 2845│H. Miyaoka, et al, JOC, 2003, 68, 3476 (Stereochem. revised). HO

O O

H

OH

439 (+)-Dysideapalaunic acid Type: Bicyclic sesterterpenoids. C25H40O2 Oil, [α]D = +61° (CHCl3). Source: Sponge Dysidea sp. Pharm: Aldose reductase inhibitor. Ref: H. Hagiwara, et al, JCS Perkin I, 1991, 343│M. Singh, et al, PM, 1999, 65, 2

154

4 Sesterterpenoids

O

OH

440 Halisulfate 7 Type: Bicyclic sesterterpenoids. C25H40O5S Source: Sponges Fasciospongia sp. (Palau, Oceania) and Coscinoderma sp. Pharm: Antibacterial (Streptomyces sp. 85E, growth and gporulation inhibitor, 20 μg/disk, IZD = 18 mm, 10 μg/disk, IZD = 15 mm, 5 μg/ disk, inactive). Ref: X. Fu, et al, JNP, 1999, 62, 1190│P. Phuwapraisirisan, et al, Tet. Lett., 2004, 45, 2125 (struct. revised)│G. Yao, et al, JNP, 2009, 72, 319 O HO

S

O

O

O

1

10

H

441 Halisulfate 9 Type: Bicyclic sesterterpenoids. C25H40O6S Amorph. solid, mp 53–54 °C, [α]D25 = −57.9° (c = 0.31, MeOH). Source: Sponges Fasciospongia sp. (Palau, Oceania) and Darwinella australensis. Pharm: Antibacterial (Streptomyces sp. 85E, growth and gporulation inhibitor, 20 μg/disk, IZD = 16 mm, 10 μg/disk, IZD = 14 mm, 5 μg/disk, inactive). Ref: G. Yao, et al, JNP, 2009, 72, 319│T. N. Makarieva, et al, JNP, 2003, 66, 1010 HO O

O S

O

O O

442 25-Hydroxyhalisulfate 9 Type: Bicyclic sesterterpenoids. C25H40O7S Oil, [α]D23 = −48.5° (c = 0.27, MeOH). Source: Sponge Fasciospongia sp. (Palau, Oceania). Pharm: Antibacterial

4.4 Bicyclic Sesterterpenoids

155

(Streptomyces sp. 85E, growth and gporulation inhibitor, 20 μg/disk, IZD = 19 mm, 10 μg/disk, IZD = 13 mm, 5 μg/disk, inactive). Ref: G. Yao, et al, JNP, 2009, 72, 319

HO O

O S

O O HO

O

H

443 Kohamaic acid A Type: Bicyclic sesterterpenoids. C25H40O2 [α]D31 = −3° (c = 0.42, CHCl3). Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic (P388, IC50 > 10 μg/mL). Ref: S. Kokubo, et al, Chem. Lett., 2001, 176 OH

O

H

444 Kohamaic acid B Type: Bicyclic sesterterpenoids. C25H40O3 [α]D30 = −4.7° (c = 0.082, CHCl3). Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic (P388, IC50 = 2.8 μg/mL). Ref: S. Kokubo, et al, Chem. Lett., 2001, 176 OH

O

H

OH

156

4 Sesterterpenoids

445 Luffalactone Type: Bicyclic sesterterpenoids. C27H38O6 Oil, [α]D = +18.8° (c = 0.48, C6H6). Source: Sponge Luffariella variabilis. Pharm: Oedema inhibitor. Ref: B. C. M. Potts, et al, JOC, 1992, 57, 2965.│R. A. Keyzers, et al, Chem. Soc. Rev., 2005, 34, 355 O

O O

O O

O

H

446 Luffarin A Type: Bicyclic sesterterpenoids. C25H36O5 Solid, [α]D20 = +101° (c = 1.7, CHCl3). Source: Sponge Luffariella geometrica (Australia). Pharm: Nicotinic receptor inhibitor. Ref: M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705 OH O O HO

O

447 Luffarin C Type: Bicyclic sesterterpenoids. C25H34O4 Yellow oil, [α]D20 = +47.1° (c = 1.3, CHCl3). Source: Sponge Luffariella geometrica (Australia). Pharm: Nicotinic receptor inhibitor. Ref: M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705 O O HO

O

4.4 Bicyclic Sesterterpenoids

157

448 Luffarin D Type: Bicyclic sesterterpenoids. C27H40O5 Yellow oil, [α]D20 = +26.4° (c = 0.3, CHCl3). Source: Sponge Luffariella geometrica (Australia). Pharm: Nicotinic receptor inhibitor. Ref: M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705 O O

O O

HO

449 Luffarin K Type: Bicyclic sesterterpenoids. C25H38O4 Oil, [α]D20 = +25.2° (c = 2.8, CHCl3). Source: Sponge Luffariella geometrica (Australia). Pharm: Nicotinic receptor inhibitor. Ref: M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705 O O HO

13

OH

450 Luffarin L Type: Bicyclic sesterterpenoids. C25H38O4 Oil, [α]D20 = +25.1° (c = 2.1, CHCl3). Source: Sponge Luffariella geometrica (Australia). Pharm: Nicotinic receptor inhibitor. Ref: M. S. Butler, et al, Aust. J. Chem., 1992, 45, 1705 O O

HO

OH 13Z

158

4 Sesterterpenoids

451 Mycaperoxide A Type: Bicyclic sesterterpenoids. C24H42O5 Cryst. (Me2CO), mp 158–159.5 °C, [α]D30 = −41.0° (c = 1.28, Me2CO). Source: Sponges Mycale sp. (Thailand) and Mycale cf. spongiosa. Pharm: Cytotoxic (P388, A549, and HT29, IC50 = 0.5–1.0 μg/mL); antiviral (Vesicular stomatitis virus and Herpes simplex virus type-1, IC50 = 0.25–1.0 μg/mL);antibacterial (gram-positive bacteria Bacillus subtilis and Staphylococcus aureus). Ref: R. J. Capon, et al, JNP, 1991, 54, 190│J. Tanaka, et al, JOC, 1993, 58, 2999│M. Singh, et al, PM, 1999, 65, 2 O OH

H

O

O

OH

H

452 Mycaperoxide B Type: Bicyclic sesterterpenoids. C24H42O5 Gum, [α]D30 = −41.3° (c = 1.27, Me2CO). Source: Sponge Mycale sp. (Thailand). Pharm: Cytotoxic (P388, A549, and HT29, IC50 = 0.5–1.0 μg/mL); antiviral (Vesicular stomatitis virus and Herpes simplex virus type-1, IC50 = 0.25–1.0 μg/mL);antibacterial (gram-positive bacteria Bacillus subtilis and Staphylococcus aureus). Ref: J. Tanaka, et al, JOC, 1993, 58, 2999 O

H O

O OH

OH H

453 Palauolide Type: Bicyclic sesterterpenoids. C25H36O3 Yellow oil, [α]D = +1.5° (c = 0.2, CHCl3). Source: Sponge Fascaplysinopsis sp. (Palau, Oceania). Pharm: PLA2 inhibitor (bee venom PLA2, 0.8 μg/mL, InRt = 85%); antibacterial. Ref: B. J. Sullivan, et al, Tet. Lett., 1982, 23, 907│E. Piers, et al, Can. J. Chem., 1994, 72, 146│E. W. Schmidt, et al, Tet. Lett., 1996, 37, 3951

4.4 Bicyclic Sesterterpenoids

O

HO

159

O

H

454 Palauolol Type: Bicyclic sesterterpenoids. C25H38O4 Oil. Source: Sponges Thorectandra sp. (Palau, Oceania) and Fascaplysinopsis sp. (Palau, Oceania). Pharm: Cytotoxic (MALME-3M, IC50 = 0.46 μg/mL; MCF7, IC50 = 14.2 μg/mL); anti-inflammatory; PLA2 inhibitor (bee venom PLA2, 0.8 μg/mL, InRt = 82%); antibacterial (Staphylococcus aureus and Bacillus subtilis, mild). Ref: R. D. Charan, et al, JNP, 2001, 64, 661│ B. Sullivan, et al, Tet. Lett., 1982, 23, 907│E. W. Schmidt, et al, Tet. Lett., 1996, 37, 3951 O

HO

O

OH H

455 Sigmosceptrellin A Type: Bicyclic sesterterpenoids. C24H40O4 Source: Sponge Sigmosceptrella laevis. Pharm: Ichthyotoxin. Ref: M. Albericci, et al, Tet. Lett., 1979, 2687│A. Albericci, et al, Tetrahedron, 1982, 38, 1881

O

H

O

H

OH H

O

160

4 Sesterterpenoids

456 Sigmosceptrellin B Prianicin B Type: Bicyclic sesterterpenoids. C24H40O4 Yellow oil. Source: Sponges Diacarnus erythraenus (Red Sea), Diacarnus cf. spinopoculum (Solomon Is. and Papua New Guinea), Sigmosceptrella laevis and Prianos sp. Pharm: Antimalarial (Plasmodium falciparum D6, IC50 = 1200 ng/mL, SI > 2.7; Plasmodium falciparum W2, IC50 = 3400 ng/mL, SI > 1.0); antitoxoplasma (Toxoplasma gondii, 0.1 μmol/L without significant toxicity); cytotoxic (Vero, IC50 = 2.5 μg/mL); differential cytotoxicity (softagar assay, 50 μg/disk, zone differential of 250 units is expected for “selective activity”, C38-L1210, −50 zone differential units; M17-L1210, −10 zone differential units); cytotoxic (HL60, GI50 = 0.14 μmol/L; Molt4, GI50 = 0.98 μmol/L; A549/ATCC, GI50 = 1.45 μmol/L; KM12, GI50 = 0.94 μmol/L; IGROV1, GI50 = 0.12 μmol/L; 786-0, GI50 = 0.61 μmol/L; BT-549, GI50 = 1.81 μmol/L). Ref: M. Albericci, et al, Tet. Lett., 1979, 2687│S. Sokoloff, et al, Experientia, 1982, 38, 337│M. Albericci, et al, Tetrahedron, 1982, 38, 1881│S. Sperry, et al, JNP, 1998, 61, 241│K. A. El Sayed, et al, JNP, 2001, 64, 522 H H O

O

O OH

457 Sigmosceptrellin C Type: Bicyclic sesterterpenoids. C24H40O4 Source: Sponges Diacarnus cf. spinopoculum (Solomon Is. and Papua New Guinea) and Sigmosceptrella laevis. Pharm: Differential cytotoxicity (softagar assay, 50 μg/disk, zone differential of 250 units is expected for “selectiveactivity”, M17-L1210, 0 zone differential units); cytotoxic (HL60 (KB), GI50 = 0.14 μmol/L; Molt4, GI50 = 0.84 μmol/L; A549/ATCC, GI50 = 0.94 μmol/L; KM12, GI50 = 0.95 μmol/L; LOX-IMVI, GI50 = 0.16 μmol/L; IGROV1, GI50 = 0.10 μmol/L; 786-0, GI50 = 0.50 μmol/L; BT-549, GI50 = 0.96 μmol/L); ichthyotoxin. Ref: M. Albericci, et al, Tet. Lett., 1979, 2687│M. Albericci, et al, Tetrahedron, 1982, 38, 1881│S. Sperry, et al, JNP, 1998, 61, 241 H H O

O

17

O

OH

458 Thorectandrol A Type: Bicyclic sesterterpenoids. C25H38O3 Yellow oil, [α]D = −15° (c = 0.15, MeOH). Source: Sponge Thorectandra sp. (Palau, Oceania). Pharm: Cytotoxic (MALME-3M, IC50 = 40 μg/mL; MCF7, IC50 = 40 μg/mL). Ref: R. D. Charan, et al, JNP, 2001, 64, 661

4.5 Cheilanthane Sesterterpenoids

161

O

H

O OH

459 Thorectandrol B Type: Bicyclic sesterterpenoids. C27H40O5 Yellow oil, [α]D = −19.4° (c = 0.07, MeOH). Source: Sponge Thorectandra sp. (Palau, Oceania). Pharm: Cytotoxic (MALME-3M, IC50 = 30 μg/mL; MCF7, IC50 = 30 μg/mL). Ref: R. D. Charan, et al, JNP, 2001, 64, 661 O O O

H

O OH

460 Ansellone A Type: Bicyclic sesterterpenoids. C27H38O5 [α]D = −15.4° (MeOH). Source: Dorid nudibranch Cadlina luteomarginata (Ansell Pt., British Columbia, Canada), sponge Phorbas sp. (Ansell Pt., British Columbia, Canada). Pharm: Activator of cAMP signaling pathway (HEK-293 cells in absence of hormone binding, EC50 = 14 μmol/L). Ref: J. Daoust, et al, Org. Lett., 2010, 12, 3208 O

O O

H O

H

OH

H

4.5 Cheilanthane Sesterterpenoids 461 Cavernosolide (24β,25ξ)-16,24-Epoxy-24,25-dihydroxy-17-cheilanthen-19,25-olide Type: Cheilanthane sesterterpenoids. C27H40O6 Cryst. (MeOH), mp 119–121 °C, [α]D = +28.7° (c = 0.3, CHCl3).

162

4 Sesterterpenoids

Source: Sponge Fasciospongia cavernosa (Bay of Naples). Pharm: Toxic (fish Gambusia salina, LC50 = 0.75 μg/mL); toxic (brine shrimp Artemia salina bioassay, LC50 = 0.37 μg/mL). Ref: S. De Rosa, et al, JNP, 1997, 60, 844

H

O 24

O O 16 19

H

25

HO

O

O

462 13,16-Epoxy-25-hydroxy-17-cheilanthen-19,25-olide Type: Cheilanthane sesterterpenoids. C25H38O4 Amorph. solid, [α]D25 = −118.7° (c = 0.44, CHCl3). Source: Sponge Ircinia sp. (Queensland). Pharm: Mitogenactivated and stress-activated kinase MSK1 inhibitor (IC50 = 4 μmol/L); mitogen activated protein kinase activated protein kinase MAPKAPK-2 inhibitor (IC50 = 90 μmol/L). Ref: M. S. Buchanan, et al, JNP 2001, 64, 300│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH O

H O

HO

463 Hamiltonin E Type: Cheilanthane sesterterpenoids. C25H38O3 Oil. Source: Nudibranch Chromodoris hamiltoni (South Africa). Pharm: Cytotoxic; antimicrobial. Ref: J. Pika, et al, Tetrahedron, 1995, 51, 8189 OH

H O

O

464 25-Hydroxy-13(24),17-cheilanthadien-16,19-olide Type: Cheilanthane sesterterpenoids. C25H38O3 Amorph. solid, [α]D25 = −8.53° (c = 0.23, CHCl3). Source: Sponge Ircinia sp. (Queensland). Pharm: Mitogen-activated and stress-activated kinase MSK1 inhibitor (IC50 = 4 μmol/L); mitogen activated protein kinase activated protein kinase MAPKAPK-2 inhibitor (IC50 = 90 μmol/L).

4.5 Cheilanthane Sesterterpenoids

163

Ref: M. S. Buchanan, et al, JNP 2001, 64, 300│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O O H

OH

465 25-Hydroxy-13(24),15,17-cheilanthatrien-19,25-olide Type: Cheilanthane sesterterpenoids. C25H36O3 Amorph. solid, [α]D = −36.09° (c = 0.53, CHCl3). Source: Sponge Ircinia sp. (Queensland). Pharm: Mitogen-activated and stress-activated kinase MSK1 inhibitor (IC50 = 4 μmol/L); mitogen activated protein kinase activated protein kinase MAPKAPK-2 inhibitor (IC50 = 90 μmol/L). Ref: M. S. Buchanan, et al, JNP 2001, 64, 300│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) H

H

O

H O

HO

466 Inorolide C Type: Cheilanthane sesterterpenoids. C27H40O5 Rods (MeOH), mp 181–183 °C, [α]D = −43.9° (c = 0.4, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 1.9 μg/mL, KB, IC50 = 6.4 μg/mL). Ref: T. Miyamoto, et al, Tet. Lett., 1992, 33, 5811│T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133

H

O

O O

H H

H

O O

467 Lintenolide C (13α,16R,25ξ)-13,16-Epoxy-25-hydroxy-17-cheilanthen-19,25-olide Type: Cheilanthane sesterterpenoids. C25H38O4 Yellow solid, [α]D25 = +47° (c = 0.004, CHCl3). Source:

164

4 Sesterterpenoids

Sponge Cacospongia cf. linteiformis (Caribbean Sea). Pharm: Antifeedant. Ref: A. Carotenuto, et al, Liebigs Ann. Chem., 1996, 77 HO O

H

O O

H

H

468 Lintenolide D (13α,16R,25ξ)-16,24-Epoxy-13,25-dihydroxy-17-cheilanthen-19,25-olide Type: Cheilanthane sesterterpenoids. C25H38O5 Yellow solid, [α]D25 = +93° (c = 0.004, CHCl3). Source: Sponge Cacospongia cf. linteiformis (Caribbean Sea). Pharm: Antifeedant. Ref: A. Carotenuto, et al, Liebigs Ann. Chem., 1996, 77 OH

HO O

O

16

H

H

O

H

469 Lintenolide E (13α,16S,25ξ)-16,24-Epoxy-13,25-dihydroxy-17-cheilanthen-19,25-olide Type: Cheilanthane sesterterpenoids. C25H38O5 [α]D25 = −29° (c = 0.004, CHCl3). Source: Sponge Cacospongia cf. linteiformis (Caribbean Sea). Pharm: Antifeedant. Ref: A. Carotenuto, et al, Liebigs Ann. Chem., 1996, 77 OH

HO O 16

H

H

O O

H

470 Petrosaspongiolide A Ircinolide A Type: Cheilanthane sesterterpenoids. C27H40O6 Cryst., mp 248–251 °C, [α]D25 = −15° (c = 0.02, CHCl3). Source: Sponges Petrosaspongia nigra (New Caledonia), Dactylospongia sp. and Ircinia sp. Pharm: Cytotoxic (NSCLC-N6, IC50 = 13.0 μg/mL). Ref: Japan. Pat., 1993, 213 988; CA, 120, 45936x│A. R. Lal, et al, Tet. Lett., 1994, 35, 2603│L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451

4.5 Cheilanthane Sesterterpenoids

H

24

H

O

O

25

O

165

O

17 16

H

H

O O

H 21

471 Petrosaspongiolide B Ircinolide B Type: Cheilanthane sesterterpenoids. C27H40O6 mp 284 °C, [α]D25 = −15° (c = 0.02, CHCl3); cryst., mp 238–240 °C, [α]D25 = −71° (c = 0.03, CHCl3). Source: Sponges Petrosaspongia nigra (New Caledonia), Ircinia sp. and Dactylospongia sp. Pharm: Cytotoxic (NSCLC-N6, IC50 = 14.8 μg/mL); cytotoxic (P388, IC50 = 619 ng/mL); antimicrobial. Ref: A. R. Lal, et al, Tet. Lett., 1994, 35, 2603│R. C. Cambie, et al, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1996, 52, 709│L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451 H

O

H O

O

O

H O

O

H

472 Petrosaspongiolide C Type: Cheilanthane sesterterpenoids. C29H42O8 [α]D25 = −12.5° (c = 0.003, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLCN6, IC50 = 0.5 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451 H

O

O O

O H

O O

O O

473 Petrosaspongiolide D Type: Cheilanthane sesterterpenoids. C27H40O7 [α]D25 = −27° (c = 0.003, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLCN6, IC50 = 5.2 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451

166

4 Sesterterpenoids

H

O

O O

O H

O O

OH

474 Petrosaspongiolide E Type: Cheilanthane sesterterpenoids. C27H38O7 [α]D25 = −19.4° (c = 0.003, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLCN6, IC50 = 4.5 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451 H

O

O O

O H

H

O O

O

475 Petrosaspongiolide F Type: Cheilanthane sesterterpenoids. C27H38O8 [α]D25 = −17.8° (c = 0.002, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLCN6, IC50 = 8.7 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451 H

O

O O

O H

O O

COOH

476 Petrosaspongiolide H Type: Cheilanthane sesterterpenoids. C25H36O7 [α]D25 = +4.3° (c = 0.003, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLCN6, IC50 = 8.1 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451 H

O

H COOH

O O

O

OH

4.5 Cheilanthane Sesterterpenoids

167

477 Petrosaspongiolide I Type: Cheilanthane sesterterpenoids. C29H42O8 [α]D25 = −28° (c = 0.001, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLCN6, IC50 = 6.8 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451 H

O

O O

O H

O

O

O O

478 Petrosaspongiolide J Type: Cheilanthane sesterterpenoids. C29H44O8 Amorph. solid, [α]D25 = −14.5° (c = 0.003, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLC-N6, IC50 = 6.3 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451

H

O

O

O

O COOH

H

O O

479 Petrosaspongiolide M Type: Cheilanthane sesterterpenoids. C27H40O6 Amorph. solid, [α]D = −28.8° (c = 0.02, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: PLA2 selective inhibitor. Ref: A. Randazzo, et al, JNP, 1998, 61, 571 O

H

O O

H H

O

H HO

O

168

4 Sesterterpenoids

480 Petrosaspongiolide N Type: Cheilanthane sesterterpenoids. C29H42O8 Amorph. solid, [α]D = −23.0° (c = 0.001, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: PLA2 selective inhibitor. Ref: A. Randazzo, et al, JNP, 1998, 61, 571 O H

O O

H

O

H HO

H

O

O O

481 Petrosaspongiolide P Type: Cheilanthane sesterterpenoids. C25H38O5 Amorph. solid, [α]D = +13.8° (c = 0.001, MeOH). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: PLA2 selective inhibitor. Ref: A. Randazzo, et al, JNP, 1998, 61, 571 H

OH O

H

H O

H HO

H

O

482 Petrosaspongiolide Q Type: Cheilanthane sesterterpenoids. C27H40O7 Amorph. solid, [α]D = +5.8° (c = 0.001, MeOH). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: PLA2 selective inhibitor. Ref: A. Randazzo, et al, JNP, 1998, 61, 571 H

OH O

H

O

H HO

H O O

O

4.5 Cheilanthane Sesterterpenoids

169

483 Petrosaspongiolide R Type: Cheilanthane sesterterpenoids. C25H36O5 Amorph. solid, [α]D25 = −15.6° (c = 0.003, MeOH). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: PLA2 selective inhibitor. Ref: A. Randazzo, et al, JNP, 1998, 61, 571│L. Ferreiro-Mederos, et al, Nat. Prod. Res., 2009, 23, 256 COOH

H

O

H O

HO

484 (–)-Spongianolide A Type: Cheilanthane sesterterpenoids. C27H40O6 Glass, [α]D = −27.8° (c = 0.79, CH2Cl2); [α]D = −31.9° (c = 1.4, MeOH). Source: Sponge Spongia sp. Pharm: Cytotoxic; PKC inhibitor (IC50 = 20–30 μmol/L for Spongianolide A–E); antiproliferation (MCF7); antibacterial. Ref: H. He, et al, Tet. Lett., 1994, 35, 7189│T. Hata, et al, Tet. Lett., 1999, 40, 1731│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O

OH O

O HO

O

485 Spongianolide B Type: Cheilanthane sesterterpenoids. C29H44O7 [α]D = −25.7° (c = 1.1, MeOH). Source: Sponge Spongia sp. (Florida). Pharm: PKC inhibitor (IC50 = 20–30 μmol/L for Spongianolide A–E). Ref: H. He, et al, Tet. Lett., 1994, 35, 7189│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O

OH O OH O

H H

H

O HO

486 Spongianolide C Lintenolide A Type: Cheilanthane sesterterpenoids. C27H40O6 [α]D = +38° (c = 2, MeOH). Source: Sponges Cacospongia linteiformis (Bahamas) and Spongia sp.

170

4 Sesterterpenoids

(Florida). Pharm: PKC inhibitor (IC50 = 20–30 μmol/L for Spongianolide A–E); antiinflammatory. Ref: M. R. Conte, et al, Tetrahedron, 1994, 50, 849│H. He, et al, Tet. Lett., 1994, 35, 7189│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O O O

O O

H

H

HO

H

487 Spongianolide D Lintenolide B Type: Cheilanthane sesterterpenoids. C27H40O6 [α]D = −16.9° (c = 1.1, MeOH). Source: Sponges Cacospongia linteiformis (Bahamas) and Spongia sp. (Florida). Pharm: PKC inhibitor (IC50 = 20–30 μmol/L for Spongianolide A–E); antibacterial. Ref: M. R. Conte, et al, Tetrahedron, 1994, 50, 849│H. He, et al, Tet. Lett., 1994, 35, 7189│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O O O

O O

H

H

HO

H

488 Spongianolide E Type: Cheilanthane sesterterpenoids. C29H44O7 [α]D = +45° (c = 2.4, MeOH). Source: Sponge Spongia sp. (Florida). Pharm: PKC inhibitor (IC50 = 20–30 μmol/L for Spongianolide A–E); Phospholipase A2 inhibitor. Ref: H. He, et al, Tet. Lett., 1994, 35, 7189│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131-2154 (rev) O

OH O O

O O

H H

H

HO

4.6 Ophiobolane Sesterterpenoids

171

489 Spongianolide F Type: Cheilanthane sesterterpenoids. C29H44O7 [α]D = −9.4° (c = 0.7, MeOH). Source: Sponge Spongia sp. (Florida). Pharm: PLA inhibitor. Ref: H. He, et al, Tet. Lett., 1994, 35, 7189 O

OH O O

O O

H

H

HO

H

4.6 Ophiobolane Sesterterpenoids 490 Halorosellinic acid Type: Ophiobolane sesterterpenoids. C25H36O6 Cryst., [α]D29 = +20.67° (c = 0.59, MeOH). Source: Marine-derived fungus Halorosellinia oceanica BCC5149 (Thailand, cultured broth). Pharm: Antimalarial (Plasmodium falciparum, IC50 = 13 μg/mL); antituberculosis (Mycobacterium tuberculosis H37Ra, MIC = 200 μg/mL). Ref: M. Chinworrungsee, et al, BoMCL, 2001, 11, 1965│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) OH H

HOOC

16

HO

H

18

COOH

H

491 Ophiobolin A Ophiobalin Type: Ophiobolane sesterterpenoids. C25H36O4 Cryst., mp 182 °C, [α]D29 = +270° (CHCl3). Source: Marine-derived fungus Emericella variecolor GF10 (extracts, marine sediment). Pharm: Phytotoxin; photosynthesis inhibitor; antibiotic; LD50 (mus, orl) = 238 mg/kg. Ref: H. Wei, et al, Tetrahedron, 2004, 60, 6015│A. Andolfi, et al, Acta Cryst. E, 2006, 62, o2195

172

4 Sesterterpenoids

O O H O

H

14

H

6 4 3

H HO

492 Ophiobolin C Zizanin A Type: Ophiobolane sesterterpenoids. C25H38O3 Cryst., mp 121 °C, [α]D = +363° (c = 0.6, CHCl3). Source: Marine-derived fungus Emericella variecolor GF10 (extracts, marine sediment). Pharm: Phytotoxin; photosynthesis inhibitor; antiparasitic; LD50 (mus, ipr) = 4.4 mg/kg. Ref: H. Wei, et al, Tetrahedron, 2004, 60, 6015

H

O

H

H 14

6

H

4 3

O

H

HO

493 Ophiobolin G 5-Oxo-3,7,16,18-ophiobolatetraen-21-al Type: Ophiobolane sesterterpenoids. C25H34O2 Translucent fine needles, mp 131–133 °C. Source: Marine-derived fungus Emericella variecolor GF10 (extracts, marine sediment). Pharm: Phytotoxin; antibacterial (Bacillus subtilis); Inhibits etiolated wheat coleoptile growth. Ref: H. Wei, et al, Tetrahedron, 2004, 60, 6015 16

O H O

H

H

H

17

6

H

494 6-epi-Ophiobolin G Type: Ophiobolane sesterterpenoids. C25H34O2 Amorph. powder, [α]D23 = +117° (c = 1.05, MeOH). Source: Marine-derived fungus Emericella variecolor GF10 (extracts, marine sediment). Pharm: Cytotoxic (neuroblastoma cell line). Ref: H. Wei, et al, Tetrahedron, 2004, 60, 6015│M. Saleem, et al, NPR, 2007, 24, 1142 (rev)

4.6 Ophiobolane Sesterterpenoids

173

16

O H

H

H

O

17

H

6

H

495 Ophiobolin H 5,21-Epoxy-7,16,18-ophiobolatriene-3,5-diol Type: Ophiobolane sesterterpenoids. C25H38O3 Translucent fine needles, mp 125–128 °C. Source: Marine-derived fungus Emericella variecolor GF10 (extracts, marine sediment). Pharm: Antibacterial (Bacillus subtilis); inhibits etiolated wheat coleoptile growth. Ref: H. Wei, et al, Tetrahedron, 2004, 60, 6015 16

H

21

H

O

H

17

6

HO H HO

496 Ophiobolin K 3-Hydroxy-5-oxo-7,16,18-ophiobolatrien-21-al Type: Ophiobolane sesterterpenoids. C25H36O3 Amorph. powder, mp 80–82 °C, [α]D23 = +168° (c = 0.4, MeOH). Source: Marine-derived fungus Emericella variecolor GF10 (extracts, marine sediment). Pharm: Cytotoxic (T47D, IC50 = 0.35 μmol/L; MDA-MB-231, IC50 = 0.57 μmol/L; HOP18, IC50 = 0.65 μmol/L; NCI-H460, IC50 = 0.57 μmol/L; HCT116, IC50 = 0.33 μmol/L; ACHN, IC50 = 0.27 μmol/L; P388, IC50 = 0.51 μmol/L; P388/ADR, IC50 = 0.16 μmol/L, Adriamycin, IC50 = 2.56 μmol/L). Ref: H. Wei, et al, Tetrahedron, 2004, 60, 6015 O H O

H

H 14

H

6 4 3

H HO

174

4 Sesterterpenoids

497 6-epi-Ophiobolin N Type: Ophiobolane sesterterpenoids. C25H36O2 Amorph. powder, [α]D23 = +88° (c = 0.34, MeOH). Source: Marine-derived fungus Emericella variecolor GF10 (extracts, marine sediment). Pharm: Cytotoxic (neuroblastoma cell line). Ref: H. Wei, et al, Tetrahedron, 2004, 60, 6015│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) 16

O H O

H

17

H

H

H

498 Ophiobolin O Type: Ophiobolane sesterterpenoids. C27H44O4 Source: Marine-derived fungus Aspergillus sp. from zoanthid Zoanthus sp. (Ayamaru Cape, Amami Is., Japan). Pharm: Cytotoxic (P388); also inducing apoptosis and cell cycle arrest of MCF7 through activation of MAPK signaling pathways. Ref: D. Zhang, et al, Nat. Prod. Commun., 2012, 7, 1411│T. Yang, et al, BoMCL, 2012, 22, 579 O O

O

H HO

H H

H

499 6-epi-Ophiobolin O Type: Ophiobolane sesterterpenoids. C27H44O4 Source: Marine-derived fungus Aspergillus sp. from zoanthid Zoanthus sp. (Ayamaru Cape, Amami Is., Japan). Pharm: Cytotoxic (P388). Ref: D. Zhang, et al, Nat. Prod. Commun., 2012, 7, 1411 O O

O 6

H HO

H

H H

4.7 Scalarane Sesterterpenoids

175

500 Ophiobolin U Type: Ophiobolane sesterterpenoids. C25H36O2 Source: Marine-derived fungus Aspergillus ustus from green alga Codium fragile (Zhoushan Is., Zhejiang, China). Pharm: Antibacterial (inhibits growth of Escherichia coli, moderate). Ref: X. -H. Liu, et al, RSC Adv., 2013, 3, 588 OH

H

H

O

4.7 Scalarane Sesterterpenoids 501 21-Acetoxydeoxoscalarin 24,25-Epoxy-16-scalarene-12,19-diacetoxy-25-ol Type: Scalarane sesterterpenoids. C29H44O6 mp 70–72 °C, [α]D27 = +60.6° (c = 0.9, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 0.35 μg/mL, KB, IC50 = 3.1 μg/mL). Ref: T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133 O O

HO

O

O

O

502 12-O-Acetyl-16-O-deacetyl-16-epi-scalarobutenolide Type: Scalarane sesterterpenoids. C27H40O5 Amorph. Solid, [α]D23 = +62° (c = 0.26, CHCl3). Source: Sponge Hyrtios cf. erectus (Japan waters). Pharm: Cytotoxic (P388, IC50 = 2.1 μg/mL). Ref: G. Ryu, et al, JNP, 1996, 59, 515 O O

O

O

OH

176

4 Sesterterpenoids

503 12-O-Acetyl-16-O-deacetyl-12,16-diepi-scalarolbutenolide Type: Scalarane sesterterpenoids. C27H40O5 mp 179–180 °C, [α]D27 = +61.9° (c = 0.88, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 2.4 μg/mL, KB, IC50 = 7.6 μg/mL). Ref: T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133 O

O O

O

OH

504 16-Acetylfuroscalarol Type: Scalarane sesterterpenoids. C29H42O5 Oil, [α]D = +15.0° (c = 0.2, CHCl3). Source: Sponge Cacospongia scalaris (Tarifa I., Cádiz, Spain). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, ED50 = 1–5 μg/mL). Ref: A. Rueda, et al, JOC, 1997, 62, 1481 O O

O

O

O

505 12-Acetyl-12-epi-heteronemin Type: Scalarane sesterterpenoids. C31H46O7 Oil. Source: Sponges Hippospongia sp. (Taitung, Taiwan) and Hyrtios erecta. Pharm: Cytotoxic (DLD-1, IC50 = 2.4 μmol/L, control Actinomycin D, IC50 = 1.9 μmol/L; HCT116, IC50 = 2.7 μmol/L, Actinomycin D, IC50 = 0.2 μmol/L; T47D, IC50 = 0.3 μmol/L, Actinomycin D, IC50 = 0.6 μmol/L; K562, IC50 = 0.05 μmol/L, Actinomycin D, IC50 = 0.03 μmol/L); anti-inflammatory. Ref: P. Crews, et al, JNP, 1986, 49, 1041│Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987 O

O

O

O

12

H H

O H

H

O O

4.7 Scalarane Sesterterpenoids

177

506 12-epi-Acetylscalarolide 12α-Acetoxy-17-scalaren-25,24-olide Type: Scalarane sesterterpenoids. C27H40O4 Amorph. powder, [α]D = +47.8° (c = 0.9, CHCl3). Source: Sponge Cacospongia scalaris (Tarifa I., Cádiz, Spain). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, ED50 = 1–5 μg/mL). Ref: A. Rueda, et al, JOC, 1997, 62, 1481 O O O

O

507 12-Deacetoxy-21-acetoxyscalarin Type: Scalarane sesterterpenoids. C27H40O5 Amorph. solid, [α]D23 = −2.3° (c = 0.66, CHCl3). Source: Sponge Hyrtios cf. erectus (Japan waters). Pharm: Cytotoxic (P388, IC50 = 0.9 μg/mL). Ref: G. Ryu, et al, JNP, 1996, 59, 515 HO

O O

O O

508 12-Deacetoxyscalaradial Desacetoxyscalaradial Type: Scalarane sesterterpenoids. C25H38O3 Source: Sponges Cacospongia scalaris (Japan waters) and Cacospongia mollior (Mediterranean Sea). Pharm: Cytotoxic (L1210, very potent); ichthyotoxin; antifeedant (fish). Ref: F. Yasuda, et al, Experientia, 1981, 37, 110│S. De Rosa, et al, JNP, 1994, 57, 256│A. Carotenuto, et al, Liebigs Ann. Chem., 1996, 77 O

OH

O H H

H

178

4 Sesterterpenoids

509 12-Deacetoxyscalarin 19-acetate Type: Scalarane sesterterpenoids. C27H40O4 Amorph. solid, [α]D = −24.3° (c = 0.014, MeOH). Source: Sponge Hippospongia sp. (Taitung, Taiwan), Brachiaster sp. Pharm: Cytotoxic (DLD-1, HCT116, T47D, K562, all IC50s > 10 μmol/L). Ref: S. -N. Wonganuchitmeta, et al, JNP, 2004, 67, 1767│Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987 O

O

O

O H H

H

H

510 12,16-diepi-12-O-Deacetyl-16-O-acetylfuroscalarol Type: Scalarane sesterterpenoids. C27H40O4 Oil, [α]D25 = −44.2° (c = 0.33, CHCl3). Source: Sponge Spongia agaricina (Cádiz, Spain). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL, A549, IC50 = 1 μg/mL, HT29, IC50 = 1 μg/mL). Ref: A. Rueda, et al, JNP, 1998, 61, 258 HO

H H

O

H

O O

511 12-epi-O-Deacetyl-19-deoxyscalarin 12-O-Deacetyl-17-deoxyscalarin Type: Scalarane sesterterpenoids. C25H38O3 Oil or needles (MeOH), mp 274–275 °C, [α]D25 = −2° (c = 0.15, MeOH). [α]D = −22.4° (c = 1, CHCl3). Source: Sponges Hyrtios gumminae (Similan Is. Andaman Sea, Thailand), Heteronema erecta (India waters) and Hyrtios erecta. Pharm: Cytotoxic (HuCCA-1, IC50 = 42 μmol/L, control Etoposide, IC50 = 5.1 μmol/L; KB, IC50 = 7.0 μmol/L, Etoposide, IC50 = 0.5 μmol/L; HeLa, IC50 = 23 μmol/L, Etoposide, IC50 = 0.4 μmol/L; MDA-MB-231, IC50 = 5.9 μmol/L, Etoposide, IC50 = 0.3 μmol/L; T47D, IC50 = 5.2 μmol/L, Etoposide, IC50 = 0.1 μmol/L; H69AR, IC50 = 57 μmol/L, Etoposide, IC50 = 46 μmol/L; P388, moderate); cytotoxic (P388 cell line, moderate). Ref: Y. Venkateswarlu, et al, Indian J. Chem., Sect. B, 1995, 34, 563│G. R. Pettit, et al, Coll. Czech. Chem. Comm., 1998, 63, 1671│C. Mahidol, et al, JNP, 2009, 72, 1870

4.7 Scalarane Sesterterpenoids

179

O

OH

O

H

H

H

512 12-Deacetyl-12,18-diepi-Scalaradial Type: Scalarane sesterterpenoids. C25H38O3 Cryst., mp 216–218 °C, [α]D = −129° (c = 1.2, CHCl3). Source: Sponge Spongia idia. Pharm: Molluscacidal; ichthyotoxin; PLA2 inhibitor; anti-inflammatory. Ref: R. P. Walker, et al, JOC, 1980, 45, 4976 O

OH 12

18

O

513 16-O-Deacetyl-16-epi-scalarobutenolide Type: Scalarane sesterterpenoids. C25H38O4 Amorph. solid, [α]D23 = +19.2° (c = 0.24, CHCl3). Source: Sponge Hyrtios cf. erectus (Japan waters). Pharm: Cytotoxic (P388, IC50 = 0.4 μg/mL) (Ryu, 1996); cytotoxic (P388, IC50 > 1000 ng/mL, control 12-epiScalarin, IC50 > 1000 ng/mL) (Tsuchiya, 1998). Ref: G. Ryu, et al, JNP, 1996, 59, 515│N. Tsuchiya, et al, JNP, 1998, 61, 468 O OH

O

OH

514 Deoxoscalarin Type: Scalarane sesterterpenoids. C27H42O4 Crystal (CCl4), mp 166–168 °C, [α]D = + 42.5°C, (c = 1.1, CHCl3). Source: Sponge Spongia officinalis, nudibranches Glossodoris tricolor (Naples), Hypselodoris orsini. Pharm: Toxic (brine shrimp). Ref: G. Cimino, et al, Experientia, 1973, 29, 934│G. Cimino, et al, Experientia, 1974, 30, 846│G. Cimino, et al, JCS Perkin I, 1977, 1587│G. Cimino, et al, Comp. Biochem. Physiol., B, 1982, 73, 471│G. Cimino, et al, Experientia, 1993, 49, 582

180

4 Sesterterpenoids

O O

HO

O

515 Deoxoscalarin-3-one Type: Scalarane sesterterpenoids. C27H40O5 Amorph. solid (MeOH), mp 65–67 °C, [α]D27 = +63.6° (c = 0.87, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 0.95 μg/mL, KB, IC50 = 5.2 μg/mL). Ref: T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133 O O

HO

O

O

516 12-epi-Deoxoscalarin-3-one Type: Scalarane sesterterpenoids. C27H40O5 Amorph. solid (MeOH), mp 132–135 °C, [α]D27 = +10.2° (c = 0.10, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 6.6 μg/mL, KB, IC50 = 22.8 μg/mL). Ref: T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133 O

HO O

O

O

517 12-Desacetylfuroscalarol Type: Scalarane sesterterpenoids. C25H38O3 Cryst. (MeOH), mp 238–242 °C, [α]D20 = +62°, (c = 0.4, CHCl3). Source: Sponge Hyrtios sp. (Okinawa). Pharm: Stimulates nerve growth factor synth. Ref: Y. Doi, et al, CPB, 1993, 41, 2190

4.7 Scalarane Sesterterpenoids

OH

181

O

OH

518 19-Dihydroscalaradial 12-Acetoxy-25-hydroxy-16-scalaren-24-al Type: Scalarane sesterterpenoids. C27H42O4 Amorph. powder, [α]D = +50.5° (c = 0.4, CHCl3). Source: Sponge Cacospongia scalaris (Tarifa I., Cádiz, Spain). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, ED50 = 1–5 μg/mL). Ref: A. Rueda, et al, JOC, 1997, 62, 1481 O O

HO

O H

519 12α,25α-Dihydroxy-16-scalaren-24,25-olide Type: Scalarane sesterterpenoids. C25H38O4 Cryst. (MeOH), mp 194 °C, [α]D16 = +15.4° (c = 0.35, CHCl3). Source: Sponge Hyrtios sp. (Okinawa). Pharm: NGF synthesis stimulator, antidementia props. Ref: Y. Doi, et al, CPB, 1993, 41, 2190 HO OH

O O H

520 24,25-Epoxy-25-hydroxy-16-scalaren-12-one 12-Deacetoxy-12-oxodeoxoscalarin Type: Scalarane sesterterpenoids. C25H38O3 Powder, [α]D = +32.6° (c = 0.5, CHCl3). Source: Nudibranch Glossodoris atromarginata, sponge Spongia sp. Pharm: Cytotoxic (hmn thyroid carcinoma). Ref: A. Fontana, et al, JNP, 1999, 62, 1367

182

4 Sesterterpenoids

O

HO

O

521 24,25-Epoxy-16-scalarene-12β,25α-diol Type: Scalarane sesterterpenoids. C25H40O3 Cryst., mp 218–220 °C, [α]D25 = +17.1° (c = 0.31, CHCl3); [α]D = +13.5° (c = 0.5, CHCl3). Source: Sponges Spongia sp. and Hyrtios erecta (Japan waters), nudibranch Glossodoris atromarginata (India waters). Pharm: Cytotoxic (P388, IC50 > 1000 ng/mL, control 12-epi-Scalarin, IC50 > 1000 ng/mL). Ref: N. Tsuchiya, et al, JNP, 1998, 61, 468│A. Fontana,et al, JNP, 1999, 62, 1367 HO

HO

H

O

H

H

522 (3β,12α,25α)-24,25-Epoxy-16-scalarene-3,12,25-triol Type: Scalarane sesterterpenoids. C25H40O4 mp 229–231 °C, [α]D25 = +11.4° (c = 0.56, MeOH/CHCl3 1:1). Source: Sponge Hyrtios erecta (Japan waters). Pharm: Cytotoxic (P388, IC50 = 250.0 ng/mL, control 12-epi-Scalarin, IC50 > 1000 ng/mL). Ref: N. Tsuchiya, et al, JNP, 1998, 61, 468 HO

H HO

HO

O

H

H

523 Furoscalarol Type: Scalarane sesterterpenoids. C27H40O4 Crystal (petroleum ether), mp 181–183 °C, [α]D = +14.7° (c = 1, CHCl3). Source: Sponge Cacospongia mollior. Pharm: Antifeedant; platelet aggregation inhibitor. Ref: F. Cafieri, et al, Gazz. Chim. ltal., 1977, 107, 71│G. Cimino, et al, Tet. Lett., 1978, 2041

4.7 Scalarane Sesterterpenoids

183

O O

O

OH

524 Heteronemin Type: Scalarane sesterterpenoids. C29H44O6 Cryst. (petrol), mp 182 °C. Source: Sponges Hippospongia sp. (Taitung, Taiwan), Heteronema erecta [Syn. Heteronema erecta], Leiosella idia, Hyrtios erecta, Cacospongia scalaris, Hyattella intestinalis and Spongia idia. Pharm: Cytotoxic (DLD-1, IC50 = 0.001 μmol/L, control Actinomycin D, IC50 = 1.9 μmol/L; HCT116, IC50 = 0.001 μmol/L, Actinomycin D, IC50 = 0.2 μmol/L; T47D, IC50 = 0.001 μmol/L, Actinomycin D, IC50 = 0.6 μmol/L; K562, IC50 = 0.001 μmol/L, Actinomycin D, IC50 = 0.03 μmol/L); toxic (brine shrimp and abalone larvae); antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 99%); PLA2 inhibitor; anti-inflammatory. Ref: R. Kazlauskas, et al, Tet. Lett., 1976, 30, 2631│ Y. Kashman,et al, Tetrahedron 1977, 33, 2997│R. P. Walker, et al, JOC, 1980, 45, 4976│F. Yasuda, et al, Experientia, 1981, 37, 11O│A. D. Patil, et al, Acta Cryst. C, 1991, 47, 1250│A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949│Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987 O O O

OH 12

H H

H O

H O

525 12-epi-Heteronemin Type: Scalarane sesterterpenoids. C29H44O6 Cryst., mp 175 °C, [α]D = −35° (c = 0.01, CHCl3). Source: Sponge Hyrtios erecta (New Caledonia). Pharm: Cytotoxic; ichthyotoxin; antifeedant (fish). Ref: M. L. Bourguet-Kondracki, et al, Tet. Lett., 1994, 35, 109

184

4 Sesterterpenoids

O O O

OH 12

H

H

O

H O

H

526 Hippospongide C Type: Scalarane sesterterpenoids. C27H40O5 Source: Sponge Hippospongia sp. (Tai-Tung, Taiwan). Pharm: Cytotoxic (four HTCLs, moderate). Ref: Y. -M. Fuh, et al, Nat. Prod. Commun., 2013, 8, 571 OH

O

H

O H

H O

H

H

O

527 21-Hydroxydeoxoscalarin Type: Scalarane sesterterpenoids. C27H42O5 Amorph. solid (MeOH), mp 121.0–125.4 °C, [α]D = +55.4° (c = 0.9, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 4.1 μg/mL, KB, IC50 = 21.0 μg/mL). Ref: T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133 O O

HO

O

H

OH

528 Hyrtial Type: Scalarane sesterterpenoids. C26H40O3 Source: Sponge Hyrtios erecta [Syn. Heteronema erecta]. Pharm: Anti-inflammatory. Ref: P. Crews, et al, Experientia, 1985, 41, 690

4.7 Scalarane Sesterterpenoids

185

O O O H

H

H

529 Hyrtiolide Type: Scalarane sesterterpenoids. C25H38O5 Amorph. solid, [α]D25 = +6° (c = 0.43, CHCl3). Source: Sponges Hyrtios gumminae (Similan Is. Andaman Sea, Thailand) and Hyrtios erectus. Pharm: Cytotoxic (HuCCA-1, IC50 = 57 μmol/L, control Etoposide, IC50 = 5.1 μmol/L; KB, IC50 = 12 μmol/L, Etoposide, IC50 = 0.5 μmol/L; HeLa, IC50 = 22 μmol/L, Etoposide, IC50 = 0.4 μmol/L; MDA-MB-231, IC50 = 26 μmol/L, Etoposide, IC50 = 0.3 μmol/L; T47D, IC50 = 34 μmol/L, Etoposide, IC50 = 0.1 μmol/L). Ref: H. Miyaoka, et al, JNP, 2000, 63, 1369│C. Mahidol, et al, JNP, 2009, 72, 1870 HO OH

O O

H

H

OH

H

530 Hyrtiosin E Type: Scalarane sesterterpenoids. C29H44O5 Powder, [α]D20 = −67.9° (c = 0.52, CHCl3). Source: Sponges Hippospongia sp. (Taitung, Taiwan) and Hyrtios erecta. Pharm: Cytotoxic (DLD-1, IC50 = 1.1 μmol/L, control Actinomycin D, IC50 = 1.9 μmol/L; HCT116, IC50 = 8.0 μmol/L, Actinomycin D, IC50 = 0.2 μmol/L; T47D, IC50 = 0.7 μmol/ L, Actinomycin D, IC50 = 0.6 μmol/L; K562, IC50 = 0.7 μmol/L, Actinomycin D, IC50 = 0.03 μmol/L). Ref: Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987│Z. -G. Yu, et al, HeIv. Chim. Acta, 2005, 88, 1004

186

4 Sesterterpenoids

O O

O O

H H

H

O

H

531 24-Methyl-25-nor-12,24-dioxo-16-scalaren-22-oic acid Type: Scalarane sesterterpenoids. C25H36O4 Amorph. solid. Source: Sponges Halichondria spp., an unidentified sponge (order Dictyoceratida). Pharm: Antimicrobial. Ref: Nakagawa, M. et al, Tet. Lett., 1987, 28, 431 O

O

HOOC

532 Norscalaral A Type: Scalarane sesterterpenoids. C26H40O4 Amorph. powder, [α]D = +48.5° (c = 0.2, CHCl3). Source: Sponge Cacospongia scalaris (Tarifa I., Cádiz, Spain). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, ED50 = 1–5 μg/mL). Ref: A. Rueda, et al, JOC, 1997, 62, 1481 O O

O

OH

533 Norscalaral B Type: Scalarane sesterterpenoids. C26H40O4 Amorph. powder, [α]D = +5.2° (c = 0.4, CHCl3). Source: Sponge Cacospongia scalaris (Tarifa I., Cádiz, Spain). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, ED50 = 1–5 μg/mL). Ref: A. Rueda, et al, JOC, 1997, 62, 1481

4.7 Scalarane Sesterterpenoids

187

O O

O

OH

534 Norscalaral C Type: Scalarane sesterterpenoids. C26H38O3 Amorph. powder, [α]D = +22.3° (c = 0.2, CHCl3). Source: Sponge Cacospongia scalaris (Tarifa I., Cádiz, Spain). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, ED50 = 1–5 μg/mL). Ref: A. Rueda, et al, JOC, 1997, 62, 1481 O O O

535 Salmahyrtisol C 24,25-Epoxy-12,25-dihydroxy-16-scalaren-3-one Type: Scalarane sesterterpenoids. C25H38O4 Cryst., mp 195–196 °C, [α]D25 = +40.3° (c = 0.65, CHCl3). Source: Sponge Hyrtios erecta (Japan waters). Pharm: Cytotoxic (P388, IC50 = 14.5 ng/mL, MKN1, IC50 = 57.7 ng/mL, MKN7, IC50 = 56.0 ng/mL, MKN74, IC50 = 36.8 ng/mL; P388, control 12-epi-Scalarin, IC50 > 1000 ng/mL); antineoplastic (in vivo, life-prolonging effect on P388 leukemia implanted mice, dose = 8.0 mg/kg, ILS (increase in lifespan) = 74.4%, dose = 4.0 mg/kg, ILS = 51.2%, dose = 2.0 mg/kg, ILS = 31.4%, dose = 1.0 mg/kg, ILS = 32.6%, dose = 0.5 mg/kg, ILS = 24.4%). Ref: N. Tsuchiya, et al, JNP, 1998, 61, 468 HO

H O

H

HO

H

O

188

4 Sesterterpenoids

536 Scalaradial Type: Scalarane sesterterpenoids. C27H40O4 Crystal (EtOH), mp 111–113 °C, [α]D = +47.5° (c = 0.9, MeOH). Source: Sponges Cacospongia scalaris (Japan waters) and Cacospongia mollior. Pharm: PLA2 inhibitor; anti-inflammatory; ichthyotoxin. Ref: G. Cimino, et al, Experientia, 1973, 29, 934│G. Cimino, et al, Experientia, 1974, 30, 846│F. Yasuda, et al, Experientia, 1981, 37, 110│G. Cimino, et al, Experientia, 1993, 49, 582│R. Puliti, et al, Acta Crystallogr., Sect. C. 1995, 51, 1703 O O

O

O H

H

H

537 12-epi-Scalaradial Type: Scalarane sesterterpenoids. C27H40O4 mp 188–190 °C, [α]D = +36.5° (CHCl3). Source: Sponge Hyrtios erecta [Syn. Heteronema nitens]. Pharm: Bee venom inhibitor. Ref: G. Cimino, et al, Experientia, 1979, 35, 1277 O O

O

H

O

18

12

H

H

538 18-epi-Scalaradial Type: Scalarane sesterterpenoids. C27H40O4 Amorph. powder, [α]D = −37.9° (c = 0.8, CHCl3). Source: Sponge Cacospongia scalaris (Tarifa I., Cádiz, Spain). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, ED50 = 1–5 μg/mL). Ref: A. Rueda, et al, JOC, 1997, 62, 1481 O O

O

O H

H

4.7 Scalarane Sesterterpenoids

189

539 Scalarafuran Type: Scalarane sesterterpenoids. C27H49O4 Cryst., mp 182 °C, [α]D = −19.8° (c = 0.9, CHCl3). Source: Sponges Hyrtios gumminae (Similan Is. Andaman Sea, Thailand), Hippospongia sp. (Taitung, Taiwan) and Spongia idia. Pharm: Cytotoxic (HuCCA-1, IC50 = 49 μmol/L, control Etoposide, IC50 = 5.1 μmol/L; KB, IC50 = 58 μmol/L, Etoposide, IC50 = 0.5 μmol/L; HeLa, IC50 = 63 μmol/L, Etoposide, IC50 = 0.4 μmol/L; MDA-MB-231, IC50 = 14 μmol/L, Etoposide, IC50 = 0.3 μmol/L; T47D, IC50 = 28 μmol/L, Etoposide, IC50 = 0.1 μmol/L; H69AR, IC50 = 51 μmol/L, Etoposide, IC50 = 46 μmol/L); cytotoxic (DLD-1, HCT116, T47D, K562, all IC50s > 10 μmol/L). Ref: R. P. Walker, et al, JOC, 1980, 45, 4976│C. Mahidol, et al, JNP, 2009, 72, 1870│Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987 O

OH

H

O

H O

H

540 16-epi-Scalarolbutenolide Type: Scalarane sesterterpenoids. C27H40O5 Amorph. powder, [α]D25 = −7.3° (c = 0.15, CHCl3). Source: Sponge Spongia agaricina (Cádiz, Spain). Pharm: Cytotoxic (P388, IC50 = 5 μg/mL, A549, IC50 = 5 μg/mL, HT29, IC50 = 5 μg/mL). Ref: A. Rueda, et al, JNP, 1998, 61, 258 O HO

H H

O

H

O O

541 Sesterstatin 1 Type: Scalarane sesterterpenoids. C25H38O4 Amorph. powder, mp 297–298 °C, [α]D22 = +16.3° (c = 0.12, CHCl3). Source: Sponge Hyrtios erecta (Maldives). Pharm: Antineoplastic (P388, ED50 = 0.46 μg/mL). Ref: G. R. Pettit, et al, JNP, 1998, 61, 13│G. R. Pettit, et al, BoMCL, 1998, 8, 2093

190

4 Sesterterpenoids

O

HO

H HO

O

H

H

542 Sesterstatin 2 Type: Scalarane sesterterpenoids. C25H38O4 Amorph. powder, mp 295–296 °C, [α]D22 = +13.8° (c = 0.09, CHCl3). Source: Sponge Hyrtios erecta (Maldives). Pharm: Antineoplastic (P388, ED50 = 4.2 μg/mL); antibacterial (inhibits growth of grampositive bacterium Staphylococcus aureus). Ref: G. R. Pettit, et al, JNP, 1998, 61, 13│G. R. Pettit, et al, BoMCL, 1998, 8, 2093 O

O

HO

H HO

H

H

543 Sesterstatin 3 Type: Scalarane sesterterpenoids. C25H38O4 Amorph. powder, mp 293–294 °C, [α]D22 = +27.2° (c = 0.22, CHCl3). Source: Sponge Hyrtios erecta (Maldives). Pharm: Antineoplastic (P388, ED50 = 4.3 μg/mL). Ref: G. R. Pettit, et al, JNP, 1998, 61, 13│G. R. Pettit, et al, BoMCL, 1998, 8, 2093

HO

H HO

O

O

H

H

544 Similan A Type: Scalarane sesterterpenoids. C26H40O3 Solid, mp 164–165 °C, [α]D22 = −4.5° (c = 0.16, CHCl3). Source: Sponge Hyrtios gumminae (Similan Is. Andaman Sea, Thailand).

4.8 Methyl- and Dimethylscalarane Sesterterpenoids

191

Pharm: Cytotoxic (HuCCA-1, IC50 = 90 μmol/L, control Etoposide, IC50 = 5.1 μmol/L; KB, IC50 = 75 μmol/L, Etoposide, IC50 = 0.5 μmol/L; HeLa, IC50 = 125 μmol/L, Etoposide, IC50 = 0.4 μmol/L; MDA-MB-231, IC50 = 58 μmol/L, Etoposide, IC50 = 0.3 μmol/L; T47D, IC50 = 70 μmol/L, Etoposide, IC50 = 0.1 μmol/L; H69AR, IC50 > 125 μmol/L, Etoposide, IC50 = 46 μmol/L). Ref: C. Mahidol, et al, JNP, 2009, 72, 1870 O

O

OH H

H H

545 (12β,16α,24ξ)-Trihydroxy-17-scalaren-25,24-olide Type: Scalarane sesterterpenoids. C25H38O5 Source: Sponge Hyrtios gumminae (Similan Is. Andaman Sea, Thailand). Pharm: Cytotoxic (HuCCA-1, IC50 = 65 μmol/L, control Etoposide, IC50 = 5.1 μmol/L; KB, IC50 = 14 μmol/L, Etoposide, IC50 = 0.5 μmol/L; HeLa, IC50 = 26 μmol/L, Etoposide, IC50 = 0.4 μmol/L; MDA-MB-231, IC50 = 29 μmol/L, Etoposide, IC50 = 0.3 μmol/L; T47D, IC50 = 48 μmol/L, Etoposide, IC50 = 0.1 μmol/L). Ref: C. Mahidol, et al, JNP, 2009, 72, 1870 O OH

O OH

H

H

OH

H

4.8 Methyl- and Dimethylscalarane Sesterterpenoids 546 12α-Acetoxy-24,25-epoxy-24-hydroxy-20,24-dimethylscalarane Type: Methyl- and dimethylscalarane sesterterpenoids. C29H48O4 Oil, [α]D = +65° (c = 0.61, CH2Cl2). Source: Sponge Carteriospongia foliascens. Pharm: Ichthyotoxin. Ref: J. C. Braekman, et al, Tetrahedron, 1985, 41, 4603

192

4 Sesterterpenoids

O O

O OH

547 12-Acetoxy-16-hydroxy-20,24-dimethyl-24-oxo-25-scalaranal Type: Methyl- and dimethylscalarane sesterterpenoids. C29H46O5 Oil, [α]D = +95.6° (c = 0.27, CHCl3). Source: Sponges Strepsichordaia lendenfeldi (Great Barrier Reef), Carteriospongia foliascens and Phyllospongia sp. Pharm: Ichthyotoxin. Ref: J. C. Braekman, et al, Tetrahedron, 1985, 41, 4603│B. F. Bowden, et al, JNP, 1992, 55, 1234│M. C. Roy, et al, JNP, 2002, 65, 1838 O O

H

O

O

OH

548 12α-Acetoxy-22-hydroxy-24-methyl-24-oxo-16-scalaren-25-al Type: Methyl- and dimethylscalarane sesterterpenoids. C28H42O5 Unstable foam, Sol. CHCl3, MeOH; poorly sol. H2O. Source: Sponge Lendenfeldia sp. Pharm: Antiinflammatory, platelet aggregation inhibitor. Ref: R. Kazlauskas, et al, Aust. J. Chem., 1982, 35, 51 O O HO

O

O

4.8 Methyl- and Dimethylscalarane Sesterterpenoids

193

549 (12α,16β,25ξ)-23,25-Cyclo-12-Acetoxy-16,25-dihydroxy-20,24-dimethyl24-scalaranone Type: Methyl- and dimethylscalarane sesterterpenoids. C29H46O5 Cryst., mp 190–193 °C, [α]D = +46° (c = 1.46, CH2Cl2). Source: Sponge Carteriospongia foliascens. Pharm: Ichthyotoxin. Ref: J. C. Braekman, et al, Tetrahedron, 1985, 41, 4603 O

OH O

O

OH

550 Dendalone 24-Methyl-24,25-dioxoscalar-16-en-12β-yl-3-hydroxy-butanoate Type: Methyl- and dimethylscalarane sesterterpenoids. C30H46O5 Glass, [α]D = +12° (c = 0.4, CHCl3). Source: Sponge Phyllospongia dendyi [Syn. Carteriospongia cf. foliascens]. Pharm: Anti-inflammatory (in vivo). Ref: R. Kazlauskas, et al, Aust. J. Chem., 1980, 33, 1783 OH

O O

O

O

551 12β,16β,22-Dihydroxy-22-acetoxy-24β-methylscalaran-25,24-olide Type: Methyl- and dimethylscalarane sesterterpenoids. C28H44O6 Cryst. (MeOH), mp 270–271 °C. Source: Sponge Lendenfeldia sp. Pharm: Anti-inflammatory. Ref: R. Kazlauskas, et al, Aust. J. Chem., 1982, 35, 51 HO

O

12

O

22

O

O 24

H OH

194

4 Sesterterpenoids

552 16α,22-Dihydroxy-24-methyl-24-oxo-25,12-scalaranolide Type: Methyl- and dimethylscalarane sesterterpenoids. C26H40O5 Amorph. solid (di-Ac), [α]D = +12° (c = 1, CHCl3) (di-Ac). Source: Sponge Lendenfeldia frondosa (Solomon Is.). Pharm: Anti-inflammatory. Ref: R. Kazlauskas, et al, Aust. J. Chem., 1982, 35, 51│C. B. Rao, et al, JNP, 1991, 54, 364│K. A. Alvi, et al, JNP, 1992, 55, 859 O

O HO

O

12 16

OH

553 16β,22-Dihydroxy-24-methyl-24-oxo-25,12-scalaranolide Type: Methyl- and dimethylscalarane sesterterpenoids. C26H40O5 Cryst. (DMF/MeCN), mp 279–280 °C, [α]D21 = 46.8° (c = 1, MeOH). Source: Sponge Lendenfeldia sp. Pharm: Anti-inflammatory. Ref: R. Kazlauskas, et al, Aust. J. Chem., 1982, 35, 51│K. A. Alvi, et al, JNP, 1992, 55, 859│L. Chill, et al, Tetrahedron, 2004, 60, 10619 O

O

O

HO 16

OH

554 Foliaspongin Type: Methyl- and dimethylscalarane sesterterpenoids. C32H52O6 Cryst. (MeOH), mp 186–189 °C, [α]D = +44 (CHCl3). Source: Sponge Phyllospongia foliascens (Okinawa). Pharm: Anti-inflammatory. Ref: H. Kikuchi, et al, CPB, 1981, 29, 1492│H. Kikuchi, et al, CPB, 1983, 31, 552 OH

O

O

O O OH

4.8 Methyl- and Dimethylscalarane Sesterterpenoids

195

555 16β-Hydroxy-22-acetoxy-24-methyl-24-oxo-25,12-scalaranolide Type: Methyl- and dimethylscalarane sesterterpenoids. C28H42O6 Cryst. (EtOAc/petrol), mp 244–246 °C, [α]D21 = +27.7° (c = 1, CHCl3). Source: Sponge Lendenfeldia sp. Pharm: Anti-inflammatory. Ref: R. Kazlauskas, et al, Aust. J. Chem., 1982, 35, 51

O

O

O

O

O OH

556 12β-Hydroxy-22-acetoxy-24-methyl-24-oxo-16-scalaren-25-al Type: Methyl- and dimethylscalarane sesterterpenoids. C28H42O5 Colorless oil, [α]D = −12.2° (c = 0.1, CHCl3). Source: Nudibranch Glossodoris sedna (Costa Rica). Pharm: PLA2 inhibitor (mammalian, IC50 = 18 μg/mL). Ref: A. Fontana, et al, JNP, 2000, 63, 527 O O

O

OH

O

22

557 12α-O-(3-Hydroxy-4-methylpentanoyl)-16α-hydroxy-20,24-dimethyl-25-nor-17scalaren-24-one Type: Methyl- and dimethylscalarane sesterterpenoids. C32H52O5 Oil, [α]D25 = 0° (c = 0.2, CH2Cl2). Source: Sponge Carteriospongia foliascens (Sulawesi, Indonesia). Pharm: hRCE protease inhibitor (hmn Ras-converting enzyme). Ref: D. E. Williams, et al, JNP, 2009, 72, 1106 OH

O O

H H

O

H

OH

196

4 Sesterterpenoids

558 12α-O-(3-Hydroxypentanoyloxy)-16α-ethoxy-24β-hydroxy-20,24-dimethyl-17scalaren-25,24-olide Type: Methyl- and dimethylscalarane sesterterpenoids. C35H56O7 Source: Sponge Carteriospongia foliascens (Sulawesi, Indonesia). Pharm: hRCE protease inhibitor (hmn Ras-converting enzyme). Ref: D. E. Williams, et al, JNP, 2009, 72, 1106 OH

O O

O

O OH

H

O

H

H

559 12α-O-(3-Hydroxypentanoyloxy)-16α-ethoxy-24α-hydroxy-20,24-dimethyl-17scalaren-25,24-olide Type: Methyl- and dimethylscalarane sesterterpenoids. C35H56O7 Source: Sponge Carteriospongia foliascens (Sulawesi, Indonesia). Pharm: hRCE protease inhibitor (hmn Ras-converting enzyme). Ref: D. E. Williams, et al, JNP, 2009, 72, 1106 OH

O O

O

H

O

OH

O

H

H

560 24-Methyl-12,24,25-trioxo-16-scalaren-22-oic acid Type: Methyl- and dimethylscalarane sesterterpenoids. C26H36O5 Cryst. (Et2O/petrol), mp 251–252 °C, [α]D21 = +33.5° (c = 1, CHCl3). Source: Sponge Lendenfeldia sp. Pharm: Anti-inflammatory. Ref: R. Kazlauskas, et al, Aust. J. Chem., 1982, 35, 51 O HOOC

O

O

4.8 Methyl- and Dimethylscalarane Sesterterpenoids

197

561 Phyllofenone D Type: Methyl- and dimethylscalarane sesterterpenoids. C26H38O2 Cryst. (CHCl3), mp 280–282 °C, [α]D25 = +113.8° (c = 0.18, CHCl3). Source: Sponge Phyllospongia foliascens (Yongxing I., South China Sea, China). Pharm: Cytotoxic. Ref: H. -J. Zhang, et al, Helv. Chim. Acta, 2009, 92, 762 OH O

12

H

H

H

562 Phyllolactone A Type: Methyl- and dimethylscalarane sesterterpenoids. C31H48O5 Powder, [α]D20 = +9.5° (c = 0.254, MeOH). Source: Sponge Phyllospongia lamellosa. Pharm: HIV-1 envelopemediated fusion inhibitor (in vitro). Ref: L. C. Chang, et al, Tetrahedron, 2001, 57, 5731

OH

O

O

O O

563 Phyllolactone B Type: Methyl- and dimethylscalarane sesterterpenoids. C30H46O5 Powder, [α]D20 = +10.6° (c = 0.09, MeOH). Source: Sponge Phyllospongia lamellosa. Pharm: HIV-1 envelope-mediated fusion inhibitor (in vitro). Ref: L. C. Chang, et al, Tetrahedron, 2001, 57, 5731

OH

O O

O

O

198

4 Sesterterpenoids

564 Phyllolactone C Type: Methyl- and dimethylscalarane sesterterpenoids. C29H44O5 Powder, [α]D20 = +8.6° (c = 0.14, MeOH). Source: Sponge Phyllospongia lamellosa. Pharm: HIV-1 envelopemediated fusion inhibitor (in vitro). Ref: L. C. Chang, et al, Tetrahedron, 2001, 57, 5731

OH

O

O

O O

565 Phyllolactone D Type: Methyl- and dimethylscalarane sesterterpenoids. C32H48O6 Amorph. solid, [α]D20 = +7.2° (c = 0.08, MeOH). Source: Sponge Phyllospongia lamellosa. Pharm: HIV-1 envelope-mediated fusion inhibitor (in vitro). Ref: L. C. Chang, et al, Tetrahedron, 2001, 57, 5731 O O

O

O

O O

566 Phyllolactone E Type: Methyl- and dimethylscalarane sesterterpenoids. C27H42O4 Oil, [α]D20 = +3° (c = 0.02, MeOH). Source: Sponge Phyllospongia lamellosa. Pharm: HIV-1 envelopemediated fusion inhibitor (in vitro). Ref: L. C. Chang, et al, Tetrahedron, 2001, 57, 5731

OH

O

O

OH

4.9 Miscellaneous Sesterterpenoids

199

4.9 Miscellaneous Sesterterpenoids 567 Alotaketal C Type: Miscellaneous sesterterpenoids. C28H42O6 Source: Sponge Phorbas sp. (Ansell Point, Howe Sound, British Columbia, Canada). Pharm: Similar levels of activation of cAMP signalling to the standard probe, forskolin. Ref: J. Daoust, et al, JOC, 2013, 78, 8267 O

HO O O

O O

568 Ansellone B (2012) Type: Miscellaneous sesterterpenoids. C27H38O5 Source: Sponge Phorbas sp. (R. O. Korea). Pharm: NO production inhibitor (LPS-stimulated RAW 264.7 cells, low μmol/L). Ref: W. Wang, et al, Org. Lett., 2012, 14, 4486 O OH H H

OH

O O

569 Asperterpenoid A Type: Miscellaneous sesterterpenoids. C25H38O3 Source: Mangrove-derived fungus Aspergillus sp. (endophytic) from unidentified mangrove (no location given). Pharm: Antituberculosis (mPTPB inhibitor). Ref: X. Huang, et al, Org. Lett., 2013, 15, 721

HH

H

O

OH

OH

200

4 Sesterterpenoids

570 Asperterpenol A Type: Miscellaneous sesterterpenoids. C25H42O Source: Mangrove-derived fungus Aspergillus sp. (endophytic) from unidentified mangrove (S. China Sea). Pharm: Acetylcholinesterase inhibitor. Ref: Z. Xiao, et al, Org. Lett., 2013, 15, 2522

H H H H

OH

571 Asperterpenol B Type: Miscellaneous sesterterpenoids. C25H42O2 Source: Mangrove-derived fungus Aspergillus sp. (endophytic) from unidentified mangrove (S. China Sea). Pharm: Acetylcholinesterase inhibitor. Ref: Z. Xiao, et al, Org. Lett., 2013, 15, 2522

H H HO H

OH

572 Cacospongionolide B Type: Miscellaneous sesterterpenoids. C25H36O4 Cryst. (MeOH), mp 116–118 °C, [α]D = +28.2° (c = 2.8, CHCl3). Source: Sponge Fasciospongia cavernosa (Adriatic Sea). Pharm: Antimicrobial; toxic (brine shrimp and fish); PLA2 inhibitor; anti-inflammatory. Ref: S. De Rosa, et al, JNP, 1995, 58, 1776│S. De Rosa, et al, Tetrahedron, 1995, 51, 10 731│A. Soriente, et al, EurJOC, 2000, 947 (abs config) H H 3

O

O HO

O

573 Cacospongionolide E Type: Miscellaneous sesterterpenoids. C25H36O4 [α]D = −85.4° (c = 0.2, CHCl3). Source: Sponge Fasciospongia cavernosa (Adriatic Sea). Pharm: PLA2 inhibitor (hmn secretory); LC50 (brine shrimp Artemia salina) = 1.29 μg/mL, (fish) = 1.01 μg/mL. Ref: S. De Rosa, et al, JNP, 1998, 61, 931

4.9 Miscellaneous Sesterterpenoids

201

O

H

O

O

HO

574 Cacospongionolide F Type: Miscellaneous sesterterpenoids. C25H36O4 Amorph. solid, [α]D = −123° (c = 0.21, CHCl3). Source: Sponge Fasciospongia cavernosa (Northern Adriatic Sea). Pharm: Antibacterial (gram-positive bacteria Bacillus subtilis, Micrococcus luteus, MIC = 0.78 μg/mL); toxic (brine shrimp lethality, Artemiasalina bioassay, IC50 = 0.17 ppm); toxic (fish, IC50 = 0.7 ppm). Ref: S. De Rosa, et al, JNP, 1999, 62, 1316│D. Demeke, et al, Org. Lett., 2003, 5, 991 O

H H

O

O HO

575 25-Deoxycacospongionolide B Type: Miscellaneous sesterterpenoids. C25H36O3 Cryst. (MeOH), mp 159–161 °C, [α]D = +10.5° (c = 1.40, CHCl3). Source: Sponge Fasciospongia cavernosa (Adriatic Sea). Pharm: Toxic (brine shrimp Artemia salina, LC50 = 0.74 μg/mL). Ref: S. De Rosa, et al, JNP, 1995, 58, 1776│S. De Rosa, et al, Tetrahedron, 1995, 51, 10 731 H O

O O

576 Diacarperoxide S Type: Miscellaneous sesterterpenoids. C25H44O5 Source: Sponge Diacarnus megaspinorhabdosa (Pula Baranglompo I., Indonesia). Pharm: Cytotoxic. Ref: S. R. M. Ibrahim, Nat. Prod. Commun., 2012, 7, 9

202

4 Sesterterpenoids

O

O

O

O OH

577 Flabelliferin A Type: Miscellaneous sesterterpenoids. C30H48O6 Source: Sponge Carteriospongia flabellifera (Tutuba I., Vanuatu). Pharm: Cytotoxic (hmn colon cancer cell lines, modest). Ref: T. Diyabalanage, et al, JNP, 2012, 75, 1490 O O

O

O

OH H

H

H O

H

578 Flabelliferin B Type: Miscellaneous sesterterpenoids. C27H42O4 Source: Sponge Carteriospongia flabellifera (Tutuba I., Vanuatu). Pharm: Cytotoxic (hmn colon cancer cell lines, modest). Ref: T. Diyabalanage, et al, JNP, 2012, 75, 1490 O O

H

O

H

OH

H

579 Hippospongide A Type: Miscellaneous sesterterpenoids. C25H36O3 White powder, mp 272–274 °C, [α]D25 = −66° (c = 0.1, CHCl3). Source: Sponge Hippospongia sp. (Taitung, Taiwan). Pharm: Cytotoxic (DLD-1, HCT116, T47D, K562, all IC50s > 10 μmol/L). Ref: Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987

4.9 Miscellaneous Sesterterpenoids

203

O

HO

O H

H H

580 Hippospongide B Type: Miscellaneous sesterterpenoids. C25H40O3 White powder, mp 289–291 °C, [α]D25 = −3° (c = 0.05, CHCl3). Source: Sponge Hippospongia sp. (Taitung, Taiwan). Pharm: Cytotoxic (DLD-1, HCT116, T47D, K562, all IC50s > 10 μmol/L). Ref: Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987 O

OH

O H H

H

H

H

581 (–)-Hyrtiosal Type: Miscellaneous sesterterpenoids. C25H38O3 Cryst., mp 119–121 °C, [α]D = −73.8° (c = 0.42, CHCl3). Source: Sponges Hyrtios gumminae (Similan Is. Andaman Sea, Thailand) and Hyrtios erecta (Okinawa). Pharm: Cytotoxic (HuCCA-1, IC50 = 9.1 μmol/L, control Etoposide, IC50 = 5.1 μmol/L; KB, IC50 = 7.8 μmol/L, Etoposide, IC50 = 0.5 μmol/L; HeLa, IC50 = 18 μmol/L, Etoposide, IC50 = 0.4 μmol/L; MDA-MB-231, IC50 = 5.4 μmol/L, Etoposide, IC50 = 0.3 μmol/L; T47D, IC50 = 9.1 μmol/L, Etoposide, IC50 = 0.1 μmol/L; H69AR, IC50 = 31 μmol/L, Etoposide, IC50 = 46 μmol/L); cytotoxic (DLD-1, HCT116, T47D, K562, all IC50s > 10 μmol/L); antiproliferative (KB cells in vitro, IC50 = 3–10 μg/mL); platelet aggregation inhibitor. Ref: K. Iguchi, et al, JOC, 1992, 57, 522│C. Mahidol, et al, JNP, 2009, 72, 1870│Y. -C. Chang, et al, Mar. Drugs, 2012, 10, 987 O H H H

OH

O

204

4 Sesterterpenoids

582 Inorolide A Type: Miscellaneous sesterterpenoids. C27H40O5 Crystal (EtOH), mp 118–120 °C, [α]D = −26.7° (c = 0.3, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 1.9 μg/mL, KB, IC50 = 3.4 μg/mL). Ref: T. Miyamoto, et al, Tet. Lett., 1992, 33, 5811│T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133 H

OH

O

O

24 25

H

O O

583 Inorolide B Type: Miscellaneous sesterterpenoids. C27H38O4 Colorless needle, mp 84–85 °C, [α]D = +52° (c = 0.8, CHCl3). Source: Nudibranch Chromodoris inornata (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 0.72 μg/mL, KB, IC50 = 2.2 μg/mL). Ref: T. Miyamoto, et al, Tet. Lett., 1992, 33, 5811│T. Miyamoto, et al, Tetrahedron, 1999, 55, 9133

H

H

O

H

O

O

O

H

584 Ircinianin lactam A Type: Miscellaneous sesterterpenoids. C27H35NO6 Source: Sponge Psammocinia sp. (various locations in New South Wales and Victoria, Australia). Pharm: Leads for treatment of inflammatory pain, epilepsy and both breathing or movement disorders. Ref: W. Balansa, et al, Org. Biomol. Chem., 2013, 11, 4695 O N

HO O H H O O

H OH

4.9 Miscellaneous Sesterterpenoids

205

585 Isophorbasone A Type: Miscellaneous sesterterpenoids. C25H32O3 Source: Sponge Phorbas sp. (R. O. Korea). Pharm: NO production inhibitor (LPS-stimulated RAW 264.7 cells, low μmol/L). Ref: W. Wang, et al, Org. Lett., 2012, 14, 4486

O

O OH

H

586 13E-Lintenone Type: Miscellaneous sesterterpenoids. C25H36O3 Oil, [α]D25 = −75.5° (c = 0.004, CHCl3). Source: Sponges Cacospongia cf. linteiformis (Bahamas) and Cacospongia cf. linteiformis (Caribbean Sea). Pharm: Toxic (mosquito fish Gambusia affinis, LD50 = 10 ppm; brine shrimp Artemia salina, LD50 = 109 ppm); antifeedant (fish Carassius auratus). Ref: E. Fattorusso, et al, JOC, 1992, 57, 6921│A. Carotenuto, et al, Tetrahedron, 1995, 51, 10 751 O

O O

H 10

13

587 13Z-Lintenone Type: Miscellaneous sesterterpenoids. C25H36O3 [α]D25 = −75° (c = 0.03, CHCl3). Source: Sponge Cacospongia cf. linteiformis (Caribbean Sea). Pharm: Ichthyotoxic (mosquito fish Gambusia affinis); antifeedant. Ref: A. Carotenuto, et al, Tetrahedron, 1995, 51, 10 751 O

H

13

O O

206

4 Sesterterpenoids

588 Luffariellin A Type: Miscellaneous sesterterpenoids. C25H36O5 Oil, [α]D = +40.1° (c = 0.01, CHCl3). Source: Sponge Luffariella variabilis. Pharm: PLA2 inhibitor; calcium homeostasis modifier. Ref: M. R. Kernan,. et al, JOC, 1987, 52, 3081

HO

O

O

25

HO

O

589 Luffariellin B Type: Miscellaneous sesterterpenoids. C25H36O5 Oil, [α]D = −55° (c = 0.03, CHCl3). Source: Sponge Luffariella variabilis. Pharm: PLA2 inhibitor. Ref: M. R. Kernan,. et al, JOC, 1987, 52, 3081 OH O

25

HO H

O

O

590 Merochlorin A Type: Miscellaneous sesterterpenoids. C25H29ClO4 Source: Marine-derived streptomycete Streptomyces sp. (sediment, Oceanside, California). Pharm: Antibacterial (MRSA, potent). Ref: L. Kaysser, et al, JACS, 2012, 134, 11988│G. Sakoulas, et al,, PLoS One, 2012, 7│L. Kaysser, et al, JACS, 2014, 136, 14626 (structure revised) OH

O

Cl

O

HO

591 Merochlorin B Type: Miscellaneous sesterterpenoids. C25H29ClO4 Source: Marine-derived streptomycete Streptomyces sp. (sediment, Oceanside, California). Pharm: Antibacterial (MRSA, potent). Ref: L. Kaysser, et al, JACS, 2012, 134, 11988

4.9 Miscellaneous Sesterterpenoids

207

O

OH

Cl

HO

O

592 Neomangicol A Type: Miscellaneous sesterterpenoids. C25H37ClO5 Amorph. solid, [α]D = −96° (c = 0.39, MeOH). Source: Marine-derived fungus Fusarium heterosporum CNC-477 (tentatively identified, driftwood, Bahamas). Pharm: Cytotoxic (HCT116 in vitro); antibacterial (inhibits growth of gram-positive bacterium Bacillus subtilis). Ref: M. K. Renner, et al, JOC, 1998, 63, 8346

HO

H H

HO

OH

HO

Cl

OH

593 Neomangicol B Type: Miscellaneous sesterterpenoids. C25H37BrO5 Amorph. solid, [α]D = −106° (c = 0.20, MeOH). Source: Marine-derived fungus Fusarium heterosporum CNC-477 (tentatively identified, driftwood, Bahamas). Pharm: Cytotoxic (HCT116, in vitro). Ref: M. K. Renner, et al, JOC, 1998, 63, 8346

HO

H H

HO

OH

HO OH

Br

594 Petrosaspongiolide K Type: Miscellaneous sesterterpenoids. C24H36O3 [α]D25 = −15.4° (c = 0.004, CHCl3). Source: Sponge Petrosaspongia nigra (New Caledonia). Pharm: Cytotoxic (NSCLCN6, IC50 = 1.3 μg/mL). Ref: L. G. Paloma, et al, Tetrahedron, 1997, 53, 10451

208

4 Sesterterpenoids

OH O

O

595 Phorbasone A Type: Miscellaneous sesterterpenoids. C25H34O3 Source: Sponge Phorbas sp. (Gageo I., R. O. Korea). Pharm: Ca2+ Deposition enhancer (in osteoblasts). Ref: J. -R. Rho, et al, Org. Lett., 2011, 13, 884

H

O O

H

H

OH

596 Phorbasone A acetate Type: Miscellaneous sesterterpenoids. C27H36O4 Source: Sponge Phorbas sp. (R. O. Korea). Pharm: NO production inhibitor (LPS-stimulated RAW 264.7 cells, low μmol/L). Ref: W. Wang, et al, Org. Lett., 2012, 14, 4486 O O O

H

O

H

597 Phorone A Type: Miscellaneous sesterterpenoids. C24H32O3 Source: Sponge Phorbas sp. (R. O. Korea). Pharm: NO production inhibitor (LPS-stimulated RAW 264.7 cells, low μmol/L). Ref: W. Wang, et al, Org. Lett., 2012, 14, 4486

O H H H

OH

OH

4.9 Miscellaneous Sesterterpenoids

209

598 Suberitenone A Type: Miscellaneous sesterterpenoids. C27H40O4 Gum, [α]D = −152.8° (c = 0.5, CHCl3). Source: Sponge Suberites sp. (psychrophilic, cold water, King George I. and McMurdo Sound, Antarctica, major metabolite). Pharm: Cholesteryl ester transfer protein (CETP) inhibitor; anti-atherosclerosis. Ref: Shin, J. et al, JOC, 1995, 60, 7582│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O

H

OH

H H

O O

599 Suberitenone B Type: Miscellaneous sesterterpenoids. C27H42O5 Cryst., mp 232–234 °C, [α]D = −15.9° (c = 0.7, CHCl3). Source: Sponge Suberites sp. (psychrophilic, cold water, King George I. and McMurdo Sound, Antarctica, major metabolite). Pharm: Cholesteryl ester transfer protein (CETP) inhibitor (used to mediate transfer of cholesteryl ester and triglyceride between high and low-density lipoproteins). Ref: Shin, J. et al, JOC, 1995, 60, 7582│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O OH H H H

O O

OH

5 Triterpenoids 5.1 Linear Triterpenoids 600 Auriculol Type: Linear triterpenoids. C34H58O8 Oil, [α]D25 = +0.12° (c = 0.1, CHCl3). Source: Sea hare Dolabella auricularia (Japan). Pharm: Cytotoxic (HeLa-S3, IC50 = 6.7 μg/mL). Ref: H. Kigoshi, et al, Tet. Lett., 2001, 42, 7461 O O O

OH

HO

O O O

601 Aurilol Type: Linear triterpenoids. C30H53BrO7 Oil, [α]D30 = +4.6° (c = 0.41, CHCl3). Source: Sea hare Dolabella auricularia (Indo-Pacific). Pharm: Cytotoxic (HeLa-S3, IC50 = 4.3 μg/mL). Ref: K. Suenaga, et al, JNP, 1998, 61, 515 O

H OH

Br

O H

O

OH

O

H

H

OH

602 Callicladol Type: Linear triterpenoids. C30H51BrO7 Cryst. (EtOH), mp 198–199 °C, [α]D23 = +75.1° (c = 0.6, CHCl3). Source: Red alga Laurencia sp. (Vietnam). Pharm: Cytotoxic (P388, IC50 = 1.75 μg/mL). Ref: Y. Matsuo, et al, Chem. Lett., 1995, 1043│ M. Suzuki, et al, Chem. Lett., 1995, 1045 O

H

O O

O H Br

O

H

H

OH

https://doi.org/10.1515/9783110655155-003

OH

212

5 Triterpenoids

603 10-epi-Dehydrothyrsiferol Type: Linear triterpenoids. C30H51BrO6 Oil, [α]D25 = +20.7° (c = 0.76, CHCl3). Source: Red alga Laurencia viridis sp. nov (Macaronesia in Canary Is.). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL, A549, IC50 = 5 μg/mL, HT29, IC50 = 5 μg/mL, MEL28, IC50 = 5 μg/mL). Ref: M. Norte, et al, Tet. Lett., 1996, 37, 2671

O 10

O H

O

28

H

O

15

OH

OH H

Br

604 Dioxepandehydrothyrsiferol Type: Linear triterpenoids. C30H51BrO6 Amorphous white solid, [α]D25 = +39° (c = 0.07, CHCl3). Source: Red alga Laurencia viridis (off Canary Is.). Pharm: Cytotoxic (P388, A549, HT29, MEL28, inactive at concentrations lower than 1 μg/mL). Ref: C. P. Manríquez, et al, Tetrahedron, 2001, 57, 3117

O

H O O Br

O

OH

OH H

605 Hippospongic acid A Type: Linear triterpenoids. C30H46O3 [α]D25 = +37° (c = 0.22, CHCl3). Source: Sponge Hippospongia sp. (Japan). Pharm: Inhibits gastrulation of starfish embryos. Ref: S, Ohta, et al, Tet. Lett., 1996, 37, 7765│ H. Hioki, et al, Tet. Lett., 1998, 39, 7745│ M. Tokumasu,et al, JCS Perkin 1, 1999, 489│ H. Hioki, et al, Tetrahedron, 2001, 57, 1235 COOH O

5.1 Linear Triterpenoids

213

606 16-epi-Hydroxydehydrothyrsiferol Type: Linear triterpenoids. C30H51BrO7 Amorphous white solid, [α]D25 = +12° (c = 0.07, CHCl3). Source: Red alga Laurencia viridis (off Canary Is.). Pharm: Cytotoxic (P388, A549, HT29, MEL28, inactive at concentrations lower than 1 μg/mL). Ref: C. P. Manríquez, et al, Tetrahedron, 2001, 57, 3117 HO

O

OH

HO O O H

O

H

H

Br

607 Isodehydrothyrsiferol Type: Linear triterpenoids. C30H51BrO6 Oil, [α]D25 = +6.5° (c = 0.23, CHCl3). Source: Red alga Laurencia viridis sp. nov (Macaronesia in Canary Is.). Pharm: Cytotoxic (P388, IC50 = 0.01 μg/mL, A549, IC50 = 2.5 μg/mL, HT29, IC50 = 2.5 μg/mL, MEL28, IC50 = 2.5 μg/mL). Ref: M. Norte, et al, Tet. Lett., 1996, 37, 2671

O O H

O

H

H

O

H OH

HO H

Br

608 Lobophytene 2,6,10,15,19,23-Hexamethyl-1,5,14,18,22-tetracosapentaen-4-ol Type: Linear triterpenoids. C30H52O Source: Soft coral Lobophytum sp. (Vietnam). Pharm: Cytotoxic (A549, IC50 = 8.2 μmol/L, control Mitoxantrone, IC50 = 6.1 μmol/L; HT29, IC50 = 5.6 μmol/L, Mitoxantrone, IC50 = 6.5 μmol/L). Ref: H. T. Nguyen, et al, Arch. Pharm. Res. 2010, 33, 503 OH 3

3

214

5 Triterpenoids

609 Magireol A Type: Linear triterpenoids. C30H53BrO6 Cryst., mp 98.5–100 °C, [α]D = 0°. Source: Red alga Laurencia obtusa. Pharm: Cytotoxic. Ref: T. Suzuki, et al, Chem. Lett., 1987, 361 OH

O O H

O

OH

H OH

H

Br

610 Magireol B Type: Linear triterpenoids. C30H51BrO5 Cryst., mp 64.5–66 °C, [α]D = +7.9° (c = 1.00, CHCl3). Source: Red alga Laurencia obtusa. Pharm: Cytotoxic. Ref: T. Suzuki, et al, Chem. Lett., 1987, 361 OH OH 16

O

H

15 28

O H

O

H

Br

611 Magireol C Type: Linear triterpenoids. C30H51BrO5 mp 67–69 °C, [α]D = +6.4° (c = 1.00, CHCl3). Source: Red alga Laurencia obtusa. Pharm: Cytotoxic. Ref: T. Suzuki, et al, Chem. Lett., 1987, 361 OH OH 16

O O H Br

O

H

H

15

5.1 Linear Triterpenoids

215

612 Martiriol Type: Linear triterpenoids. C30H50O7 Amorphous white solid, [α]D25 = +4° (c = 0.003, CHCl3). Source: Red alga Laurencia viridis (off Canary Is.). Pharm: Cytotoxic (P388, A549, HT29, MEL28, inactive at concentrations lower than 10 μg/mL). Ref: C. P. Manríquez, et al, Tetrahedron, 2001, 57, 3117 OH

O O

O

O OH

H

HO

613 Pseudodehydrothyrsiferol Type: Linear triterpenoids. C30H52O7 Amorphous white solid, [α]D25 = −13.1° (c = 0.13, CHCl3). Source: Red alga Laurencia viridis (off Canary Is.). Pharm: Cytotoxic (P388, A549, HT29, MEL28, inactive at concentrations lower than 1 μg/mL). Ref: C. P. Manríquez, et al, Tetrahedron, 2001, 57, 3117

O HO

O

O

O OH

OH

H

614 Teurilene Type: Linear triterpenoids. C30H52O5 Cryst. (diisopropyl ether), mp 84–85 °C, [α]D22 = 0° (c = 0.37, CHCl3). Source: Red alga Laurencia obtusa. Pharm: Cytotoxic (KB, IC50 = 7.0 μg/mL). Ref: T. Suzuki, et al, Tet. Lett., 1985, 26, 1329│ M. Hashimoto, et al, JOC, 1991, 56, 2299│ H. Morita, et al, Phytochemistry, 1993, 34(3): 765

H

O O O

H H

OH OH

H

615 Thyrsenol A Type: Linear triterpenoids. C30H51BrO8 Amorphous solid, [α]D25 = +12.9° (c = 0.69, CHCl3). Source: Red alga Laurencia viridis (Canary Is., Spain). Pharm: Cytotoxic (P388, IC50 = 0.25 μg/mL, A549, IC50 > 1.0 μg/mL, HT29, IC50 > 1.0 μg/mL, MEL28, IC50 > 1.0 μg/mL). Ref: M. Norte, et al, Tetrahedron., 1997, 53, 3173

216

5 Triterpenoids

OH

HO O O H

O

O

OH

OH H

Br

616 Thyrsenol B Type: Linear triterpenoids. C30H51BrO8 Amorphous solid, [α]D25 = −1.1° (c = 0.26, CHCl3). Source: Red alga Laurencia viridis (Canary Is., Spain). Pharm: Cytotoxic (P388, IC50 = 0.01 μg/mL, A549, IC50 > 1.0 μg/mL, HT29, IC50 > 1.0 μg/mL, MEL28, IC50 > 1.0 μg/mL). Ref: M. Norte, et al, Tetrahedron., 1997, 53, 3173 OH

HO O O H

O

O

OH

OH H

Br

617 Thyrsiferol 23-acetate Type: Linear triterpenoids. C32H55BrO8 Cryst. (MeOH aq), mp 118–119 °C, [α]D29 = +1.99° (c = 4.4, CHCl3). Source: Red alga Laurencia obtusa. Pharm: Cytotoxic (P388, ED50 = 0.3 ng/cm3); protein phosphatase 2A inhibitor. Ref: T. Suzuki, et al, Tet. Lett., 1985, 26, 1329

O

14

O H

O

OH

H

O

O

O

15

OH H

Br

618 Venustatriol Type: Linear triterpenoids. C30H53BrO7 Cryst., mp 161.5 °C, [α]D20 = +9.4° (c = 3.2, CHCl3). Source: Red alga Laurencia venusta. Pharm: Antiviral. Ref: S. Sakami, et al, Tet. Lett., 1986, 27, 4287

5.2 Lanostane Triterpenoids

HO

O

O H

O

OH

19

O

217

18

H OH

H

Br

5.2 Lanostane Triterpenoids 619 25-Acetoxybivittoside D (3β,12α)-Holost-9(11)-ene-25-acetoxy-3,12-diol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C69H112O34 Amorph. powder, mp 205–207 °C, [α]D20 = −9.1° (c = 0.65, Py). Source: Sea cucumber Bohadschia marmorata (Hainan I., South China Sea). Pharm: Antifungal (Candida albicans, MIC80 = 43.13 μmol/L; control Ketoconazole, MIC80 = 0.12 μmol/L; Cryptococcus neoformans, MIC80 = 2.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Aspergillus fumigatus, MIC80 = 43.13 μmol/L; Ketoconazole, MIC80 = 1.88 μmol/L; Trichophyton rubrum, MIC80 = 2.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Candida tropicalis, MIC80 = 10.78 μmol/L; Ketoconazole, MIC80 = 0.03 μmol/L; Candida krusei, MIC80 = 10.78 μmol/L; Ketoconazole, MIC80 = 0.47 μmol/L). Ref: W. -H. Yuan, et al, PM, 2009, 75, 168 HO

O

H H

OO HO HO

O O

O O

OH

HO

OH HO O OH

O

O

OH OO

O OH

OH

O

OH

HO O

OH

OH

OH

O O

O

218

5 Triterpenoids

620 Acetylpenasterol Type: Lanostane triterpenoids. C32H50O4 Cryst., mp 185–187 °C, [α]D25 = −44.7° (c = 0.59, CHCl3). Source: Sponge Penares incrustans (Okinawa). Pharm: Inhibits anti-IgE-induced release of histamine (rat peritoneal mast cells). Ref: N. Shoji, et al, JNP, 1992, 55, 1682

O O

COOH H

621 Bivittoside D Bohadschioside A; (3β,12α)-Holost-9(11)-ene-3,12-diol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[3-Omethyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside Type: Lanostane triterpenoids. C67H110O32 Cryst., mp 219–221 °C, [α]D = −7° (Py). Source: Sea cucumbers Bohadschia marmorata (Hainan I., South China Sea), Bohadschia bivittata and Thelenota ananas. Pharm: Antifungal (Candida albicans, MIC80 = 2.80 μmol/L; control Ketoconazole, MIC80 = 0.12 μmol/L; Cryptococcus neoformans, MIC80 = 0.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Aspergillus fumigatus, MIC80 = 2.80 μmol/L; Ketoconazole, MIC80 = 1.88 μmol/L; Trichophyton rubrum, MIC80 = 0.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Candida tropicalis, MIC80 = 2.80 μmol/L; Ketoconazole, MIC80 = 0.03 μmol/L; Candida krusei, MIC80 = 2.80 μmol/L; Ketoconazole, MIC80 = 0.47 μmol/L). Ref: I. Kitagawa, et al, CPB, 1981, 29, 282; 1989, 37, 61│ V. R. Hegde, et al, BoMCL, 2002, 12, 3203│ W. -H. Yuan, et al, PM, 2009, 75, 168

O HO H

HO HO O HO

O

O

OH

O

O OH

O

O

OH OH

O

OH

OH HO

HO

OO OH O O OH

OO

OH

OH

O

H

5.2 Lanostane Triterpenoids

219

622 Calcigeroside B Posietogenin 3-O-[3-O-methyl-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-[6deoxy-β-D-glucopyranosyl-(1→2)]-6-deoxy-β-D-glu-copyranosyl-(1→2)-4-O-sulfato-β-Dxylopyranoside] Type: Lanostane triterpenoids. C54H84O27S Cryst., mp 234–236 °C, [α]D20 = −49° (c = 0.1, Py). Source: Sea cucumber Pentamera calcigera (psychrophilic, cold water, Peter, Great Gulf, Sea of Japan). Pharm: Cytotoxic (IC50 = 5.0 μg/mL). Ref: S. A. Avilov, et al, JNP, 2000, 63, 65; 1349│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O

O

HO O

OO

O

OH

S

O O O

OH O

O

OH O O

O

O

O OH

OH OH

OH OH OH

OH

623 Calcigeroside C1 Posietogenin 3-O-[3-O-methyl-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)[β-D-glucopyranosyl-(1→2)]-6-deoxy-β-D-glucopyranosyl-(1→2)-4-O-sulfato-β-D-xylopyranoside] Type: Lanostane triterpenoids. C54H84O28S Cryst., mp 204–206 °C, [α]D20 = −60° (c = 0.1, Py). Source: Sea cucumber Pentamera calcigera (psychrophilic, cold water, Peter, Great Gulf, Sea of Japan). Pharm: Cytotoxic (IC50 = 5.0 μg/mL). Ref: S. A. Avilov, et al, JNP, 2000, 63, 65; 1349

220

5 Triterpenoids

O O

O

HO

OH

S

O

O

OH O

O

OH O

O O OH

OH

OH

OH

OO

O O

OH O O OH

OH

OH

624 Calcigeroside C2 3β-Hydroxyholost-7-en-23-one 3-O-[3-O-methyl-β-D-xylopyranosyl-(1→3)-β-D-glucopy ranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-6-deoxy-β-D-glucopyranosyl-(1→2)-4-O-sulfo-βD-xylopyranoside] Type: Lanostane triterpenoids. C59H94O29S Cryst., mp 226–228 °C, [α]D20 = −39° (c = 0.1, Py). Source: Sea cucumber Pentamera calcigera (psychrophilic, cold water, Peter, Great Gulf, Sea of Japan). Pharm: Cytotoxic (IC50 = 5.0 μg/mL). Ref: S. A. Avilov, et al, JNP, 2000, 63, 65; 1349│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

O O

O

HO

S

O

O

OH O

O

OH O

OH

O O OH

OH OH

OH

OO

OH

OH OH

O

O

O

O

OH

H O

5.2 Lanostane Triterpenoids

221

625 Cladoloside B 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-Dxylopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-βD-xylopyranoside] Type: Lanostane triterpenoids. C59H92O26 Source: Sea cucumbers Apostichopus japonicas (Dalian coast, Bohai Sea of China) and Cladolabes sp. Pharm: Antifungal (Candida albicans SC5314, MIC80 = 3.28 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 = 3.28 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L,Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 = 1.64 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 0.41 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 0.82 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L,Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 3.28 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: Z. Wang, et al, Food Chem., 2012, 132, 295│ S. A. Avilov, et al, Khim. Prir. Soedin., 1988, 24, 764; Chem. Nat. Compd. (Engl. Transl.), 656 O H

O H O

OH HO OH OH HO

O

O

O OH

O

O OO OH

OH OO

OH OH

OO

OH

OH

H

222

5 Triterpenoids

626 Cladoloside B1 Type: Lanostane triterpenoids. C63H100O30 Source: Sea cucumber Cladolabes schmeltzii (Nha Trang Gulf, South China Sea). Pharm: Cytotoxic (strong); haemolytic (strong). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 1527 O O

OH HO HO

O

O

OH HO O

H

H

O

HO

O

O

O

O O

O

H

OH

O OH OH

O

O OH

OH O HO

O OH

627 Cladoloside B2 Type: Lanostane triterpenoids. C63H98O30 Source: Sea cucumber Cladolabes schmeltzii (Nha Trang Gulf, South China Sea). Pharm: Cytotoxic (strong); haemolytic (strong). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 1527 O O

OH HO HO

H

O

O

OH HO O

HO

O

OH OH O OH

OH O HO

O OH

H

O O

O

OH

O O

O

O

O

H

5.2 Lanostane Triterpenoids

223

628 Cladoloside C Type: Lanostane triterpenoids. C70H110O35 Source: Sea cucumber Cladolabes schmeltzii (Nha Trang Gulf, South China Sea). Pharm: Cytotoxic (strong); haemolytic (strong). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 1527 O OH

OH

HO

HO O

O

O

O

O

O

O

O

HO

O O

O

HO

H

H

OH

OH

O

O

O

H

OH

O OH OH

O

O OH

OH O HO

O OH

629 Cladoloside C1 Type: Lanostane triterpenoids. C70H112O35 Source: Sea cucumber Cladolabes schmeltzii (Nha Trang Gulf, South China Sea). Pharm: Cytotoxic (strong); haemolytic (strong). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 1527 O OH

OH

HO

HO O

O

O

O

O

O

H

OH

OH

O

HO O

HO

O

OH OH O OH

OH O HO

O OH

H

O O

O

OH

O O

O

O

H

224

5 Triterpenoids

630 Cladoloside C2 Type: Lanostane triterpenoids. C66H106O32 Source: Sea cucumber Cladolabes schmeltzii (Nha Trang Gulf, South China Sea). Pharm: Cytotoxic (strong); haemolytic (strong). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 1527

OH

OH

HO

HO O

O

O

O

OH

H

H

O

HO

O

O O

OH HO O

O

O

OH

O

O

H

OH OH

O

O HO

OH O

OH

OH

O

631 Cladoloside D Type: Lanostane triterpenoids. C68H106O34 Source: Sea cucumber Cladolabes schmeltzii (Nha Trang Gulf, South China Sea). Pharm: Cytotoxic (strong); haemolytic (strong). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 1527 O O

OH HO

HO O

HO

O

O O

H

OH

OH

O

HO O

HO

O

OH OH O OH

OH O HO

O OH

H

O O

O

OH

O O

O

O

H

5.2 Lanostane Triterpenoids

225

632 Crellastatin I Type: Lanostane triterpenoids. C58H88O11S Amorph. powder, [α]D = +40.7° (c = 0.005, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Cytotoxic (NSCLC, in vitro, IC50 = 1.9 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│ C. Giannini, et al, Tetrahedron, 1999, 55, 13749

O H HO

O

O

O S

O

O HO

OH HO

O

5

6

633 Crellastatin J Type: Lanostane triterpenoids. C58H88O13S Amorph. powder. Source: Sponge Crella sp. (Vanuatu). Pharm: Cytotoxic (NSCLC, in vitro, IC50 = 7.6 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│ C. Giannini, et al, Tetrahedron, 1999, 55, 13749

O H O

O

HO O

S O

O HO O

OH

OH HO

HO

634 Crellastatin K Type: Lanostane triterpenoids. C58H88O12S Amorph. powder, [α]D = +22.3° (c = 0.002, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Cytotoxic (NSCLC, in vitro, IC50 = 3.7 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│ C. Giannini, et al, Tetrahedron, 1999, 55, 13749

226

5 Triterpenoids

OH H HO

O

O

O S

O

O HO

OH HO

O HO

635 Crellastatin L Type: Lanostane triterpenoids. C57H84O11S Amorph. powder, [α]D = +6.11° (c = 0.003, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Cytotoxic (NSCLC, in vitro, IC50 = 2.9 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│ C. Giannini, et al, Tetrahedron, 1999, 55, 13749

O H O

O

HO O

S O

O HO

OH HO

O

636 Crellastatin M Type: Lanostane triterpenoids. C58H88O15S2 Amorph. powder, [α]D = +48.0° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Cytotoxic (NSCLC, in vitro, IC50 = 1.1 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│ C. Giannini, et al, Tetrahedron, 1999, 55, 13749

5.2 Lanostane Triterpenoids

H

O

HO

O

227

S

O

O

O HO

OH

O

O O

HO

S

HO OH

O

637 Cucumarioside A1 Type: Lanostane triterpenoids. C55H86O22 Source: Sea cucumber Eupentacta fraudatrix (Peter the Great Gulf, Sea of Japan). Pharm: Cytotoxic; antifungal; haemolytic. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2012, 7, 517; 845 O

O H O

H O O

O

OH OH

OH O

OH

O

H OH

OH

O

O OH

O O

OH O OH

638 Cucumarioside A2 Type: Lanostane triterpenoids. C57H88O24 Source: Sea cucumber Eupentacta fraudatrix (Peter the Great Gulf, Sea of Japan). Pharm: Cytotoxic (mouse spleen lymphocytes and ascite cells of mouse Ehrlich carcinoma, moderate); haemolytic (mouse erythrocytes, high activity). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2012, 7, 517; 845

228

5 Triterpenoids

O O O

O

H O

H O O

O

OH

OH

OH

O

H OH

OH

O

O OH

O

O

O

OH O

OH

OH

639 Cucumarioside A3 (3β)-Holosta-7,25-diene-3-ol-16-one 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-6-Osulfo-β-D-glucopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→2)]-6-deoxy-β-D-glucopyranosyl(1→2)-4-O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C59H92O32S2 mp 230–231 °C (dec) (Na/K salt), [α]D20 = −80.0° (c = 0.1, Py) (Na/K salt). Source: Sea cucumber Cucumaria japonica (Northern Pacific Ocean). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, IC50 = 1 μg/mL). Ref: O. A. Drozdova, et al, Liebigs Ann./Recueil, 1997. 2351

O

O H O

OO

O O HO

OH

HO S O

S

O

O O

O HO O

O

O OH

OH OH

OH O O

OO

OH OH OH

OH

O

5.2 Lanostane Triterpenoids

229

640 Cucumarioside A6-2 (3β)-Holosta-7,25-diene-3-ol-16-one3-O-[3-O-methyl-6-O-sulfo-β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→2)]-6-deoxy-β-D-glucopyranosyl-(1→2)-4-O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C59H92O32S2 mp 230–232 °C (dec) (Na/K salt), [α]D20 = −80.0° (c = 0.1, Py) (Na/K salt). Source: Sea cucumber Cucumaria japonica (Northern Pacific Ocean). Pharm: Cytotoxic (P388, SCHABEL, A549, HT29, MEL28, IC50 = 1 μg/mL). Ref: O. A. Drozdova, et al, Liebigs Ann./Recueil, 1997. 2351

O

O H O

OO

OH OH

O S O O

OH O

S O O

O OH

O

OH O O

O OH

OH

OH

OH OH OH

O

O

OO

OH

641 Cucumarioside A8 Type: Lanostane triterpenoids. C55H90O22 Source: Sea cucumber Eupentacta fraudatrix (Peter the Great Gulf, Sea of Japan). Pharm: Cytotoxic (mouse spleen lymphocytes and ascite cells of mouse Ehrlich carcinoma); haemolytic (mouse erythrocytes, high activity); antifungal. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2012, 7, 517; 845│ A. S. Silchenko, et al, Biochem. Syst. Ecol., 2012, 44, 53 OH

HO

H O

H O O

O

OH OH

OH O

OH

O

H OH

OH

O

OH O OH

O

O

O OH

230

5 Triterpenoids

642 Cucumarioside A10 Type: Lanostane triterpenoids. C48H74O20 Source: Sea cucumber Eupentacta fraudatrix (Peter the Great Gulf, Sea of Japan). Pharm: Cytotoxic (mouse spleen lymphocytes and ascite cells of mouse Ehrlich carcinoma, moderate). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2012, 7, 517; 845 O H

O H O

OH

H OH O

O

OH

OH

OH

O

O

OH O

O

O

OH O

OH

OH

643 Cucumarioside A13 Type: Lanostane triterpenoids. C55H84O23 Source: Sea cucumber Eupentacta fraudatrix (Peter the Great Gulf, Sea of Japan). Pharm: Cytotoxic (mouse spleen lymphocytes and ascite cells of mouse Ehrlich carcinoma, moderate); haemolytic (mouse erythrocytes, high activity). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2012, 7, 517; 845 O O

O

H O

H O O

O

OH OH

OH OH O

OH

O

H OH

O

O OH

O OH

O O

OH

644 Cucumarioside B2 Type: Lanostane triterpenoids. C47H70O17 Source: Sea cucumber Eupentacta fraudatrix (Peter the Great Gulf, Sea of Japan). Pharm: Cytotoxic; haemolytic (mild). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2012, 7, 1157

5.2 Lanostane Triterpenoids

231

O

O

H

O

HO

O

H

O

HO

O

H

O

OH O

O

OH

OH

O

OH

OH

645 Cucumarioside H2 Type: Lanostane triterpenoids. C61H96O29S mp 230–232 °C, [α]D20 = −9° (c = 0.1, Py). Source: Sea cucumber Eupentacta fraudatrix (Far Eastern). Pharm: Cytotoxic (mouse spleen lymphocytes, ED50 > 100 μg/mL); cytotoxic (ascites form of mouse Ehrlich carcinoma, ED50 > 100 μg/mL); haemolytic (mouse erythrocytes, MIC100 = 25.0 μg/mL). Ref: A. S. Silchenko, et al, Nat. Prod. Res., 2012, 26, 1765 OH O O

H

O O

H H

HO

O

O

O

O

OH OH

O HO

S HO O

O

HO

O

O O

HO

OH

O O

HO O

OH

OH

646 Cucumarioside H3 Type: Lanostane triterpenoids. C54H84O26S mp 185–190 °C, [α]D20 = −37° (c = 0.1, Py). Source: Sea cucumber Eupentacta fraudatrix (Far Eastern). Pharm: Cytotoxic (mouse spleen lymphocytes, ED50 = (30.0 ± 1.1)μg/mL); cytotoxic (ascites form of

232

5 Triterpenoids

mouse Ehrlich carcinoma, ED50 > 100 μg/mL); haemolytic (mouse erythrocytes, MIC100 = 6.25 μg/mL). Ref: A. S. Silchenko, et al, Nat. Prod. Res., 2012, 26, 1765 O H O HO O O

H

O

S

O

HO HO

HO O

O

O

HO O

O HO

O

OH

OH OH

O

O

OH

H

O

OH

647 Cucumarioside H4 Type: Lanostane triterpenoids. C63H100O29S mp 210–215 °C, [α]D20 = −19° (c = 0.1, Py). Source: Sea cucumber Eupentacta fraudatrix (Far Eastern). Pharm: Cytotoxic (mouse spleen lymphocytes, ED50 = (8.2 ± 0.9)μg/mL); cytotoxic (ascites form of mouse Ehrlich carcinoma, ED50 = (35.7 ± 0.6)μg/mL); haemolytic (mouse erythrocytes, MIC100 < 1.1 μg/mL). Ref: A. S. Silchenko, et al, Nat. Prod. Res., 2012, 26, 1765 O O

H

O

O O

H H HO O

O

O S

O

O O O

HO O O O

OH

OH

HO O

HO

HO

OH

O HO

OH

OH

O

5.2 Lanostane Triterpenoids

233

648 Cucumarioside H5 Type: Lanostane triterpenoids. C60H92O29S Source: Sea cucumber Eupentacta fraudatrix (Troitsa Bay, Sea of Japan, Russia). Pharm: Cytotoxic; haemolytic. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2011, 6, 1075

O

O

H

O

HO

S

O

HO HO O O HO

O

O

OH

O

O

O

H

O HO

O

O

H

O

O

HO O

HO HO HO

O

OH

649 Cucumarioside H6 Type: Lanostane triterpenoids. C60H94O29S Source: Sea cucumber Eupentacta fraudatrix (Troitsa Bay, Sea of Japan, Russia). Pharm: Cytotoxic; haemolytic. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2011, 6, 1075

O

O H

HO

S

O

O O

HO OO O

H

O HO

HO

HO

O

H

O

OH

O OHO HO HO HO

O

O

O

O

OH

O

234

5 Triterpenoids

650 Cucumarioside H7 Type: Lanostane triterpenoids. C60H96O29S Source: Sea cucumber Eupentacta fraudatrix (Troitsa Bay, Sea of Japan, Russia). Pharm: Cytotoxic; haemolytic. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2011, 6, 1075

O

O

H

HO

S

O O

HO

HO

O

O

O OHO

HO OO

O

O

HO HO HO

OH

O

H

O HO

O

O

H

O

O

OH

651 Cucumarioside H8 Type: Lanostane triterpenoids. C58H90O29S Source: Sea cucumber Eupentacta fraudatrix (Troitsa Bay, Sea of Japan, Russia). Pharm: Cytotoxic; haemolytic. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2011, 6, 1075 OH

O

O H O

HO O

HO O

H

O S

O HO

HO HO OO OH

O O

O OHO HO HO HO

H O O OO OH

652 Cucumarioside I1 Type: Lanostane triterpenoids. C60H94O32S2 Source: Sea cucumber Eupentacta fraudatrix (Peter the Great Gulf, Sea of Japan). Pharm: Cytotoxic (weak); haemolytic (strong). Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 1053

5.2 Lanostane Triterpenoids

235

O O O HO

S O

O

O

O

HO O

O

H O

O

HO

O

H OH

O

OH

OH OH

O

H

O

O O HO

S

OH

O

OH

O

O

O OH

653 Echinoside B (3β,12α,17αOH,20S)-Holost-9(11)-ene-3,12,17-triol 3-O-[6-deoxy-β-D-glucopyranosyl(1→2)-4-O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C41H66O16S Needles +1H2O (MeOH aq) (Na salt), mp 203.5–204.5 °C, [α]D12 = −2.2° (c = 0.88, Py). Source: Sea cucumbers Actinopyga echinites and Actinopyga mauritiana. Pharm: Toxic (mice and other organism extremely). Ref: Kitagawa, I. et al, CPB, 1982, 30, 2045; 1985, 33, 5214; 1991, 39, 2282

HO

O

H

O H

O

O

S

OH O

O

O

O

OH OH

OH

O

O OH

236

5 Triterpenoids

654 Ectyoplaside A Type: Lanostane triterpenoids. C46H74O19 Amorph. solid, [α]D25 = +3° (c = 0.002, MeOH). Source: Sponge Ectyoplasia ferox (Caribbean). Pharm: Cytotoxic (mus, J774 monocyte-macro-phage, WEHI-164, P388, in vitro, IC50 = 8.5–11.0 μg/mL). Ref: F. Cafieri, et al, EurJOC, 1999, 231 OH 22S

OH HO

O

HO

COOH

O O HO

O HO

O OH

OH

O

HO

OH OH

655 Ectyoplaside B Type: Lanostane triterpenoids. C46H74O20 Amorph. solid, [α]D25 = −12° (c = 0.002, MeOH). Source: Sponge Ectyoplasia ferox (Caribbean). Pharm: Cytotoxic (mus, J774 monocyte-macro-phage, WEHI-164, P388, in vitro, IC50 = 8.5–11.0 μg/mL). Ref: F. Cafieri, et al, EurJOC, 1999, 231 OH 22S

OH HO

O COOH

HO

O O

O

HO OH

HO

O OH

OH

O

HO

OH OH

5.2 Lanostane Triterpenoids

237

656 Eryloside F 3β-Hydroxylanosta-8,24-dien-30-oic acid 3-O-[β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside] Type: Lanostane triterpenoids. C41H66O12 Amorph. solid. Source: Sponge Erylus formosus (Caribbean). Pharm: Ca2+ influx activator (IC50 ≈ 100 μg/mL); thrombin receptor antagonist. Ref: P. Stead, et al, BoMCL, 2000, 10, 661│ A. S. Antonov, et al, JNP, 2007, 70, 169

H

OH O

HO OH HO

OH O

O

H

O

OH

O

OH

657 Eryloside F1 Type: Lanostane triterpenoids. C42H68O12 Amorph. solid, [α]D25 = −23° (c = 0.1, MeOH). Source: Sponge Erylus formosus (Caribbean). Pharm: Ca2+ influx activator (IC50 ≈ 100 μg/mL). Ref: A. S. Antonov, et al, JNP, 2007, 70, 169

H

OH HO OH HO

O OH O

O

H

O

OH

O

OH

658 Eryloside G 3-Hydroxy-24-methylenelanost-8-en-30-oic acid 3-O-[2-acetamido-2-deoxy-β-Dglucopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-galactopyranoside] Type: Lanostane triterpenoids. C50H81NO17 Amorph. solid, mp 187–191 °C (dec), [α]D25 = −18.8° (c = 0.09, MeOH). Source: Sponge Erylus nobilis (Korea). Pharm: Cytotoxic (K562, IC50 = 22.1 μg/mL). Ref: J. Shin, et al, JNP, 2001, 64, 767

238

5 Triterpenoids

H

HO

HO O

HO

O

O

OH HO

OH

OH

OH

O

O

HO

O

O

O

HN

659 Eryloside H Type: Lanostane triterpenoids. C49H79NO16 Amorph. solid, mp 208–210 °C, [α]D25 = −12.4° (c = 0.07, MeOH). Source: Sponge Erylus nobilis (Korea). Pharm: Cytotoxic (K562, IC50 = 17.9 μg/mL). Ref: J. Shin, et al, JNP, 2001, 64, 767

OH

OH O

HO

O

O

OH

OH O O

OH HO

O

O

HO HN

O

660 Eryloside I Type: Lanostane triterpenoids. C51H83NO17 Amorph. solid, mp 203–206 °C, [α]D25 = −18° (c = 0.06, MeOH). Source: Sponge Erylus nobilis (Korea). Pharm: Cytotoxic (K562, IC50 = 24.8 μg/mL). Ref: J. Shin, et al, JNP, 2001, 64, 767

OH

OH O

HO

O

O OH

OH HO

OH

O

HO HN

O O

O

O

OH

5.2 Lanostane Triterpenoids

239

661 Eryloside J Type: Lanostane triterpenoids. C50H81NO16 Amorph. solid, mp 193–196 °C, [α]D25 = −16.9° (c = 0.06, MeOH). Source: Sponge Erylus nobilis (Korea). Pharm: Cytotoxic (K562, IC50 = 21.8 μg/mL). Ref: J. Shin, et al, JNP, 2001, 64, 767

OH

OH O

HO

O

O

OH

OH O O

OH HO

O

O

HO HN

O

662 Formoside B 3-Hydroxylanosta-8,24-dien-30-oic acid 3-O-[2-acetamido-2-deoxy-β-D-galactopyranosyl-(1→2)-[β-D-galactopyrano- syl-(1→3)-α-L-arabinopyranosyl-(1→3)]-α-Larabinopyranoside] Type: Lanostane triterpenoids. C54H87NO21 Amorph. solid, [α]D20 = −10.3° (c = 0.13, MeOH). Source: Sponge Erylus formosus (Caribbean). Pharm: Antifeedant (ecologically relevant reef fish Thalassoma bifasciatum). Ref: J. Kubanek, et al, Nat. Prod. Lett., 2001, 15, 275

HO HO

OH

OH OO

OH

OH OO

HO OH HO

O OH O N H

O O

O

O

OH

240

5 Triterpenoids

663 Frondoside A (3β,9β,16β)-Holost-7-ene-16-acetoxy-3-ol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-βD-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→2)]-6-deoxy-β-D-glucopyranosyl-(1→2)-4O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C60H96O29S Crystal, mp 234–236 °C, [α]D = −31° (c = 0.1, pyridine). Source: Sea cucumber Cucumaria frondosa (North Atlantic commercially harvested). Pharm: Immune system activity (glycoside Lysosomal activity, phagocytosis and ROS activator, IC50 = 0.1–0.001 μg/mL). Ref: D. L. Aminin, et al, J. Med. Food, 2008,11, 443│ M. Girard, et al, Can. J. Chem., 1990, 68, 11│ S. A. Avilov, et al, Chem. Nat. Comp., 1993, 29, 216 O

O H O

H OH O

S

OO

O

OH

O

O OO OH

OH

OO

OO

OO

O OH OH

OH

OH OH

OH

OH

664 Frondoside C (3β,20R,22R)-Lanosta-9(11),24-diene-22-acetoxy-3,20-diol 3-O-[3-O-methyl-6-O-sulfoβ-D-glucopyranosyl-(1→3)-6-O-sulfo-β-D-glucopyranosyl-(1→4)-[β-D-xylopyranosyl(1→2)]-6-deoxy-β-D-glucopyranosyl-(1→2)-4-O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C61H100O35S3 Source: Sea cucumber Cucumaria frondosa (Arctic). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL, mus lymphoma Schabel, IC50 = 1 μg/mL, A549, IC50 = 1 μg/mL, HT29, IC50 = 1 μg/mL, MEL28, IC50 = 1 μg/mL). Ref: S. A. Avilov, et al, Can. J. Chem., 1998, 76, 137

5.2 Lanostane Triterpenoids

241

O O OH H H O O

O OH O HO S O O O HO S O O O HO S O O OH O OO OO OO OH O OH OH OH OH OH OH

665 Hemoiedemoside A 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)6-O-sulfo-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-4-O-sulfo-βD-xylopyranoside] Type: Lanostane triterpenoids. C54H84O28S2 Amorph. powder, mp 225–227 °C, [α]D20 = −29.6° (c = 0.4, Py). Source: Sea cucumber Hemioedema spectabilis (depth of 3 m, off Golfo San Jorge near Comodoro Rivadavia, Argentine Patagonian coast, in Oct. 2000). Pharm: Antifungal (phytopathogenic fungus Cladosporium cucumerinum, tested concentration = 1.5–50 μg/spot, inhibition zone = 8–33 mm, considerable activity); toxic (brine shrimp Artemia salina, LC50 = 18.7 ppm). Ref: H. D. Chludil, et al, JNP, 2002, 65, 860 O H

O H O

OO OH

OH

O

OH O

S

S

O

O

O

HO

O

O

OH

OO

OO

OH OH

OH

O OH

O

OH

H

242

5 Triterpenoids

666 Hemoiedemoside B 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3-O-methyl-6-O-sulfo-β-D-glucopyranosyl(1→3)-6-O-sulfo-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-4-O-sulfoβ-D-xylopyranoside] Type: Lanostane triterpenoids. C54H84O31S3 Amorph. powder, mp 230–232 °C, [α]D20 = −28.9° (c = 0.5, Py). Source: Sea cucumber Hemioedema spectabilis (depth of 3 m, off Golfo San Jorge near Comodoro Rivadavia, Argentine Patagonian coast, in Oct. 2000). Pharm: Antifungal (phytopathogenic fungus Cladosporium cucumerinum); toxic (brine shrimp Artemia salina, LC50 = 47.2 ppm). Ref: H. D. Chludil, et al, JNP, 2002, 65, 860 O

H

O H O

OO

O O

O O

O O

S

S

O

OH

O

OH

O

OH

S

H

O

OH

OO OH

OO

O

O

OH

OH OH

OH

OH

667 Holothurin B Holothurigenol 3-O-[6-deoxy-β-D-glucopyranosyl-(1→2)-4-O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C41H64O17S Needles (EtOH aq) (Na salt), mp 224–226 °C (Na salt), [α]D17 = −11° (c = 0.3, H2O). Source: Sea cucumber Thelenota ananas, sea cucumbers Holothuria leucospilota, Holothuria lubrica, Holothuria floridiana, Holothuria edulis, Holothuria atra, Stichopus chloronotus, Actinopyga lecanora, Actinopyga flammea and Actinopyga agassizi. Pharm: Antifungal (Trichophyton mentagrophytes and Sporothrix schenckii, MIC = 1.56 μg/mL); haemolytic; piscicide. Ref: I. Kitagawa, et al, CPB, 1981, 29, 1942; 1951│ R. Kumar, et al, BoMCL 2007,17, 4387│ DNP on DVD, 2012, version 20.2

5.2 Lanostane Triterpenoids

HO

O

O H OH

H

243

O

OO OH

OH O

S

O

O

O

O

OH OH OH

668 Holothurinoside A Holothurigenol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-6deoxy-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C60H96O29 Glass, mp 232–233 °C, [α]D = −0.9° (c = 0.0135, MeOH). Source: Sea cucumber Holothuria forskolii. Pharm: Cytotoxic (P388, IC50 = 0.46 μg/mL; A549, IC50 = 0.33 μg/mL; HeLa, IC50 = 0.86 μg/mL; B16, IC50 = 0.71 μg/mL); antiviral (20 μg/mL, VSV cells in BHK, InRt = 20%). Ref: J. Rodriguez, et al, Tetrahedron, 1991, 47, 4753

HO

O

H

O

O

OH

HO OO OH OH HO O O

HO

O OH

OH O

O

O OH

OH OH

O

OH

OH

O

O H OH

244

5 Triterpenoids

669 Holothurinoside C (3β,12α,20R,22R)-22,25-Epoxyholost-9(11)-ene-3,12-diol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-β-D-xylopyranoside] Type: Lanostane triterpenoids. C54H86O23 Cryst., mp 223–225 °C. Source: Sea cucumber Holothuria forskolii. Pharm: Cytotoxic (P388, IC50 = 0.34 μg/mL; A549, IC50 = 0.16 μg/mL; HeLa, IC50 = 0.47 μg/mL; B16, IC50 = 0.93 μg/mL); antiviral (20 μg/mL, VSV cells in BHK, InRt = 20%). Ref: J. Rodriguez, et al, Tetrahedron, 1991, 47, 4753 26

21

HO

O

20R

H

3

OH HO OH OH OH O OH

O

O

OH

OO

O

22R

O

12

19

OO

18

H

O

25

27

H 30

28

29

O

OH

OH

OH

670 Holothurinoside D (3β,12α,20R,22R)-22,25-Epoxyholost-9(11)-ene-3,12-diol 3-O-[6-deoxy-β-D-glucopyranosyl-(1→2)-β-D-xylopyranoside] Type: Lanostane triterpenoids. C41H64O13 Cryst., mp 219–221 °C. Source: Sea cucumber Holothuria forskolii. Pharm: Cytotoxic (P388, IC50 = 2.00 μg/mL; A549, IC50 = 5.00 μg/mL); antiviral (20 μg/mL, VSV cells in BHK, InRt = 20%). Ref: J. Rodriguez, et al, Tetrahedron, 1991, 47, 4753 23

24

21

HO 19

3

OO OH HO O

O

OH OH

OH

29

O

18

20R 12

H

H H

30 28

26 22R

O

O

25

27

5.2 Lanostane Triterpenoids

245

671 Holotoxin A 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C67H106O32 Cryst. (CHCl3/MeOH/H2O), mp 250–253 °C, [α]D23 = −76° (c = 0.43, H2O). Source: Sea cucumbers Stichopus japonicus and Holothuria pervicax. Pharm: Haemolytic. Ref: I. Kitagawa, et al, CPB, 1978, 26, 3722

O H

O H O

OH O

O

OH O O

O

H

OH OO

O OH

OH

O

OH OH

OH OH O

OH O

OH

OO O OH

OH

OH

OH

672 Holotoxin A1 Stichoposide A; 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C66H104O31 Cryst. (EtOH), mp 258–260 °C, [α]D20 = −69.2° (c = 1.2, Py). Source: Sea cucumbers Apostichopus japonicas (Dalian coast, Bohai Sea of China) and Stichopus japonicus. Pharm: Antifungal (Candida albicans SC5314, MIC80 = 11.49 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 = 1.44 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 = 1.44 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine,

246

5 Triterpenoids

MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 1.44 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 0.18 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L,Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 5.75 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: I. I. Maltsev, et al, Comp. Biochem. Physiol., B: Comp. Biochem., 1984, 78, 421│ Z. Wang, et al, Food Chem., 2012, 132, 295 O H

O H O

OO OH HO HO

OO

OO O

O OH

OH

OH

HO

OH

OO

OH

O

OH OH

OO O

H

O

OH

OH

673 Holotoxin B 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C66H104O32 Cryst. (CHCl3/MeOH/H2O), mp 252–253 °C, [α]D23 = −78° (c = 0.28, Py). Source: Sea cucumbers Apostichopus japonicas (Dalian coast, Bohai Sea of China) and Stichopus japonicus. Pharm: Antifungal (Candida albicans SC5314, MIC80 = 11.36 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31

5.2 Lanostane Triterpenoids

247

μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 = 2.84 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 = 5.68 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 11.36 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 0.71 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L,Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 11.36 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: I. Kitagawa, et al, CPB, 1978, 26, 3722│ I. I. Maltsev, et al, Comp. Biochem. Physiol., B: Comp. Biochem., 1984, 78, 421│ Z. Wang, et al, Food Chem., 2012, 132, 295 O H

O H O

O OH

OH O

O

O

OO

O OH

H

OH

O OH

OH OH OH OO OH OH

OH

OH OO

O

OH OH

OH

OH

674 Holotoxin D Type: Lanostane triterpenoids. C66H104O32 Colourless amorph. powder, [α]D23 = −49° (c = 0.56, Py). Source: Sea cucumber Apostichopus japonicas (Dalian coast, Bohai Sea of China). Pharm: Antifungal (Candida albicans SC5314, MIC80 = 6.64 μmol/L,

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5 Triterpenoids

controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 = 6.64 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 = 13.29 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 13.29 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 6.64 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 13.29 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: Z. Wang, et al, Food Chem., 2012, 132, 295

O H HO HO

HO

O

O

O HO

OH HO HO

O O

HO

O

OH HO

O O

O

O HO

O O

OH

OH

HO

H O

O

O

O

OH

H

5.2 Lanostane Triterpenoids

249

675 Holotoxin D1 Type: Lanostane triterpenoids. C65H100O32 Source: Sea cucumber Apostichopus japonicas (Dalian coast, Bohai Sea of China). Pharm: Antifungal (broad spectrum). Ref: Z. Wang, et al, Nat. Prod. Commun., 2012, 7, 1431

O

O H

HO

O O

O HO

HO

O

O

O HO

HO OH HO

O HO

HO

O

OH HO

H

O O

O

O HO

O O

OH

HO

OH

OH

676 Holotoxin E Type: Lanostane triterpenoids. C65H102O31 Colourless amorph. powder, [α]D23 = −49° (c = 0.56, Py). Source: Sea cucumber Apostichopus japonicas (Dalian coast, Bohai Sea of China). Pharm: Antifungal (Candida albicans SC5314, MIC80 = 13.45 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 = 6.72 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 = 13.45 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 13.45 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 6.72 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L,

250

5 Triterpenoids

Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 26.89 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: Z. Wang, et al, Food Chem., 2012, 132, 295

O

O H

HO HO

H

O

O HO

O

O

O HO

O HO

HO

HO

OH O

OH HO

O

H

O O

O

O HO

O O

OH

HO

OH

OH

677 Holotoxin F Type: Lanostane triterpenoids. C59H96O25 Colourless amorph. powder, [α]D20 = −102° (c = 0.15, Py). Source: Sea cucumber Apostichopus japonicas (Dalian coast, Bohai Sea of China). Pharm: Antifungal (Candida albicans SC5314, MIC80 = 5.58 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 = 2.84 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 = 5.68 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 5.68 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 1.42 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L,

5.2 Lanostane Triterpenoids

251

Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 5.68 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: Z. Wang, et al, Food Chem., 2012, 132, 295

HO H HO

O O

O HO

O

O HO

HO

OH O

HO

H

H

O O

HO

O

O HO

O O

OH

HO

OH

OH

678 Holotoxin G Type: Lanostane triterpenoids. C58H94O25 Colourless amorph. powder, [α]D20 = −92° (c = 0.15, Py). Source: Sea cucumber Apostichopus japonicas (Dalian coast, Bohai Sea of China). Pharm: Antifungal (Candida albicans SC5314, MIC80 = 5.81 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31 μmol/L, Voriconazole,MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 = 2.90 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 = 5.81 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 2.90 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole,

252

5 Triterpenoids

MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 1.45 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 11.61 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: Z. Wang, et al, Food Chem., 2012, 132, 295

HO

H HO

O O

O HO

O

O HO

HO

OH O

HO

HO

H

H

O O

O

O HO

O HO

HO

OH

OH

679 17α-Hydroxyimpatienside A (3β,12α,17αOH,20S)-Holost-9(11),24-diene-3,12,17-triol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[3O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C67H108O33 Amorph. powder, mp 209–211 °C, [α]D20 = −11° (c = 0.205, Py). Source: Sea cucumber Bohadschia marmorata (Hainan I., South China Sea). Pharm: Antifungal (Candida albicans, MIC80 = 2.78 μmol/L; control Ketoconazole, MIC80 = 0.12 μmol/L; Cryptococcus neoformans, MIC80 = 0.69 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Aspergillus fumigatus, MIC80 = 2.78 μmol/L; Ketoconazole, MIC80 = 1.88 μmol/L; Trichophyton rubrum, MIC80 = 11.11 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Candida tropicalis, MIC80 = 2.78 μmol/L; Ketoconazole, MIC80 = 0.03 μmol/L; Candida krusei, MIC80 = 2.78 μmol/L; control Ketoconazole, MIC80 = 0.47 μmol/L). Ref: W. -H. Yuan, et al, PM, 2009, 75, 168

5.2 Lanostane Triterpenoids

HO

O

H

253

O

OH

OO OH HO HO

O O

OH

OO

O

O O

OH OH

OH

OH

O

O

OH O O

OH

OH

OH O OH

OH

OH

680 Impatienside A (3β,12α)-Holosta-9(11),24-diene-3,12-diol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-βD-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C67H108O32 Amorph. powder, mp 217–219 °C, [α]D20 = −23° (c = 0.6, Py). Source: Sea cucumbers Bohadschia marmorata (Hainan I., South China Sea) and Holothuria impatiens. Pharm: Antifungal (Candida albicans, MIC80 = 2.81 μmol/L; control Ketoconazole, MIC80 = 0.12 μmol/L; Cryptococcus neoformans, MIC80 = 0.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Aspergillus fumigatus, MIC80 = 2.81 μmol/L; Ketoconazole, MIC80 = 1.88 μmol/L; Trichophyton rubrum, MIC80 = 0.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Candida tropicalis, MIC80 = 2.81 μmol/L; Ketoconazole, MIC80 = 0.03 μmol/L; Candida krusei, MIC80 = 2.81 μmol/L; Ketoconazole, MIC80 = 0.47 μmol/L). Ref: P. Sun, et al, Chem. Biodiversity, 2007, 4, 450│ W. -H. Yuan, et al, PM, 2009, 75, 168

254

5 Triterpenoids

HO

O

O

H H

OO HO HO

O O

O O OH HO

OO O

O

OH

O

OH

OH

HO O

OH

O O

OH

HO

OH

OH

OH

OH

681 Leucospilotaside B (3β,12α,17α,24ξ)-Holost-9(11)-ene-3,12,17,24-tetrol 3-O-[6-deoxy-β-D-glucopyranosyl(1→2)-4-O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C41H66O17S Amorph. powder, mp 228–230 °C, [α]D20 = −6.7° (c = 0.3, Py). Source: Sea cucumber Holothuria leucospilota (Hainan I., South China Sea). Pharm: Cytotoxic (panel of human tumour cell lines, moderate). Ref: H. Han, et al, Chin. J. Nat. Med., 2009, 7, 346│ H. Han, et al, Chem. Biodiversity, 2010, 7, 1764 OH HO

O

H

O OH

OH O

S

O O

O

O OH OH

OH

O

O OH

5.2 Lanostane Triterpenoids

255

682 Liouvilloside A (3β,16β)-Holosta-7,24-diene-16-acetoxy-3-ol 3-O-[3-O-methyl-6-O-sulfo-β-D-glucopyranosyl-(1→3)-6-O-sulfo-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)4-O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C56H88O32S3 Amorph. powder, mp 191–193 °C，[α]D20 = −4.9° (c = 0.5, Py). Source: Sea cucumber Staurocucumis liouvillei (psychrophilic, cold water, Antarctic). Pharm: Antiviral (HSV1, < 10 μg/mL). Ref: M. S. Maier, et al, JNP, 2001, 64, 732│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

O O

H O O

HO HO

O

O

S O O

O OH S

O S

O

OH

OH

O OH

OO

O O

OH

OO

O

O

OO

O

OH

OH

683 Liouvilloside B (3β,9α,16β)-Holost-7-ene-16-acetoxy-3-ol 3-O-[3-O-methyl-6-O-sulfo-β-D-glucopyranosyl(1→3)-6-O-sulfo-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-4O-sulfo-β-D-xylopyranoside] Type: Lanostane triterpenoids. C56H90O32S3 Amorph. powder, mp 192–194 °C，[α]D20 = −10.5° (c = 0.4, Py). Source: Sea cucumber Staurocucumis liouvillei (psychrophilic, cold water, Antarctic). Pharm: Antiviral (HSV-1, < 10 μg/mL). Ref: M. S. Maier, et al, JNP, 2001, 64, 732│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)│ J. Rodriguez, et al, J. Chem. Res., Synop., 1989, 342; J. Chem. Res., Miniprint, 2620

256

5 Triterpenoids

O

O H O

H

O

OO OH

O HO O HO

S O

S

O

OO

O

OH

O

OH

OO

OH

O O

O

O

O HO

S O

OH

OH

OH

684 Marmoratoside A (3β,12α)-Holosta-9(11),25-diene-3,12-diol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C67H108O32 Amorph. powder, mp 209–211 °C, [α]D20 = −1.7° (c = 0.34, Py). Source: Sea cucumber Bohadschia marmorata (Hainan I., South China Sea). Pharm: Antifungal (Candida albicans, MIC80 = 2.81 μmol/L; control Ketoconazole, MIC80 = 0.12 μmol/L; Cryptococcus neoformans, MIC80 = 0.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Aspergillus fumigatus, MIC80 = 2.81 μmol/L; Ketoconazole, MIC80 = 1.88 μmol/L; Trichophyton rubrum, MIC80 = 0.70 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Candida tropicalis, MIC80 = 2.81 μmol/L; Ketoconazole, MIC80 = 0.03 μmol/L; Candida krusei, MIC80 = 11.24 μmol/L; Ketoconazole, MIC80 = 0.47 μmol/L). Ref: W. -H. Yuan, et al, PM, 2009, 75, 168

5.2 Lanostane Triterpenoids

HO

257

O

O

H H

OO HO HO

O

O

OH

HO

O

O

O O

OH

OH

OH HO HO

OO O

O O

OH

OH

O

OH OH

OH

OH

685 Marmoratoside B (3β,12α)-Holost-9(11),23-diene-3,12,25-triol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)β-D-glucopyranosyl-(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C67H108O33 Amorph. powder, mp 215–217 °C, [α]D20 = −8.8° (c = 0.65, Py). Source: Sea cucumber Bohadschia marmorata (Hainan I., South China Sea). Pharm: Antifungal (Candida albicans, MIC80 = 44.44 μmol/L; control Ketoconazole, MIC80 = 0.12 μmol/L; Cryptococcus neoformans, MIC80 = 44.44 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Aspergillus fumigatus, MIC80 = 44.44 μmol/L; Ketoconazole, MIC80 = 1.88 μmol/L; Trichophyton rubrum, MIC80 = 44.44 μmol/L; Ketoconazole, MIC80 = 0.12 μmol/L; Candida tropicalis, MIC80 = 44.44 μmol/L; Ketoconazole, MIC80 = 0.03 μmol/L; Candida krusei, MIC80 = 44.44 μmol/L; Ketoconazole, MIC80 = 0.47 μmol/L). Ref: W. -H. Yuan, et al, PM, 2009, 75, 168 O HO H

HO HO O HO

O

O

OH

O

O OH

O

OH

OH HO

HO

O

O

OH OH

OO OH O O OH

OO

OH

OH

O

H

OH

258

5 Triterpenoids

686 Methyl 3β,23R-dihydroxy-29-nor-lanosta-8,24-dien-28-oate 3-sulfate Type: Lanostane triterpenoids. C30H48O7S White amorph. solid, [α]D23 = +53.5° (c = 0.11, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 2 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

H

OH

OH O

S

O O

O O

687 Methyl 3β-hydroxy-23-oxo-29-nor-lanosta-8,24-dien-28-oate 3-sulfate Type: Lanostane triterpenoids. C30H46O7S White amorph. solid, [α]D28 = +36° (c = 0.10, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 1 μg/mL); toxic (brine shrimp, 50 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210 H

O

O HO

S O

O O

O

688 26-Nor-25-oxo-holotoxin A1 Type: Lanostane triterpenoids. C65H102O32 Colourless amorph. powder, [α]D20 = −28° (c = 0.30, Py). Source: Sea cucumber Apostichopus japonicas (Dalian coast, Bohai Sea of China). Pharm: Antifungal (Candida albicans SC5314, MIC80 > 45.91 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L, Terbinafine, MIC80 = 27.45 μmol/L, Ketoconazole, MIC80 = 0.1 μmol/L, Amphotericin B, MIC80 = 17.31 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Cryptococcus neoformans BLS108, MIC80 > 45.91 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 1.72 μmol/L, Ketoconazole, MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.04 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Candida tropicalis, MIC80 > 45.91 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 13.73 μmol/L, Ketoconazole, MIC80 = 0.24 μmol/L, Fluconazole, MIC80 = 1.63 μmol/L; Trichophyton rubrum 0501124, MIC80 = 45.91 μmol/L, controls: Itraconazole, MIC80 = 0.18 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole,

5.2 Lanostane Triterpenoids

259

MIC80 = 0.12 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole, MIC80 = 0.18 μmol/L, Fluconazole, MIC80 = 13.05 μmol/L; Microsporum gypseum 31388, MIC80 = 5.73 μmol/L, controls: Itraconazole, MIC80 = 0.09 μmol/L,Terbinafine, MIC80 = 0.43 μmol/L, Ketoconazole, MIC80 < 0.24 μmol/L, Amphotericin B, MIC80 = 2.16 μmol/L, Voriconazole, MIC80 = 0.36 μmol/L, Fluconazole, MIC80 = 3.26 μmol/L; Aspergillus fumigatus 0504656, MIC80 = 11.48 μmol/L, controls: Itraconazole, MIC80 = 2.83 μmol/L, Terbinafine, MIC80 = 0.86 μmol/L, Ketoconazole, MIC80 = 1.88 μmol/L, Amphotericin B, MIC80 = 34.63 μmol/L, Voriconazole,MIC80 = 0.72 μmol/L, Fluconazole, inactive). Ref: Z. Wang, et al, Food Chem., 2012, 132, 295

H

H HO HO

O

O

O HO

O

O

O HO

O O

O

OH HO

HO

HO

OH

O

O

O

H

O O

O

O HO

O O

OH

HO

OH

OH

689 Patagonicoside A (3β,12α,17αOH)-Holost-7-ene-3,12,17-triol 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)6-O-sulfo-β-D-glucopyranosyl-(1→4)-6-deoxy-β-D- glucopyranosyl-(1→2)-4-O-sulfo-βD-xylopyranoside] Type: Lanostane triterpenoids. C54H88O29S2 Amorph. powder, mp 204–206 °C, [α]D20 = −30° (c = 0.5, MeOH). Source: Sea cucumber Psolus patagonicus. Pharm: Antifungal (pathogenic fungus Cladosporium cucumerinum, 1.5–50 μg/spot, IZD = 8–19 mm, potent). Ref: A. P. Murray, et al, Tetrahedron, 2001, 57, 9563

HO

O

O OH

HO HO O HO HO O

O

O

O S

S O HO OO

O OH

OH

O HO

OO

O HO

OO OH

260

5 Triterpenoids

690 Patagonicoside B Type: Lanostane triterpenoids. C53H84O25S Source: Sea cucumber Psolus patagonicus (Bridges I., Tierra del Fuego, Argentina). Pharm: Antifungal (Cladosporium cucumerinum, moderate). Ref: V. P. Careaga, et al, Chem. Biodiversity, 2011, 8, 467

HO

O

O OH

O O

S

O

O

H

O HO

HO O O

HO HO

H

O

HO

O

O

O HO

OH

O

OH

OH

691 Patagonicoside C Type: Lanostane triterpenoids. C54H88O29S2 Source: Sea cucumber Psolus patagonicus (Bridges I., Tierra del Fuego, Argentina). Pharm: Antifungal (Cladosporium cucumerinum, moderate). Ref: V. P. Careaga, et al, Chem. Biodiversity, 2011, 8, 467

HO

O

O OH

HO

S

O OH O

S O

HO

O

O

H

O

O O

H

O HO HO

HO O O

O OHO OH

O

O

OH

OH

692 Penasterone Type: Lanostane triterpenoids. C30H46O3 Crystals (MeOH), mp 126–130 °C, [α]D25 = −18.2° (c = 0.6, CHCl3). Source: Sponge Penares incrustans (Okinawa). Pharm:

5.2 Lanostane Triterpenoids

261

Inhibits anti-IgE-induced release of histamine (rat peritoneal mast cells). Ref: N. Shoji, et al, JNP, 1992, 55, 1682

COOH

O

693 Pentactaside I Type: Lanostane triterpenoids. C48H74O20S Source: Sea cucumber Pentacta quadrangularis (Zhanjiang, Guangdong, South China Sea). Pharm: Cytotoxic (moderate). Ref: H. Han, et al, PM, 2010, 76, 1900

O

O H

HO O

O S

O HO

OO HO

HO HO

O

H

OH

OO O

O

H

O

OH

694 Pentactaside II Type: Lanostane triterpenoids. C48H74O20S Source: Sea cucumber Pentacta quadrangularis (Zhanjiang, Guangdong, South China Sea). Pharm: Cytotoxic (moderate). Ref: H. Han, et al, PM, 2010, 76, 1900

O

O H

HO O

HO HO

O S

O

H O HO

OO HO OH

OO O

O

OH

H

O

262

5 Triterpenoids

695 Pentactaside III Type: Lanostane triterpenoids. C43H66O16S Source: Sea cucumber Pentacta quadrangularis (Zhanjiang, Guangdong, South China Sea). Pharm: Cytotoxic (moderate). Ref: H. Han, et al, PM, 2010, 76, 1900

O

O

H HO O

O S

O

H OO

O HO

O

HO HO

O

H

O

OH

696 Sarasinoside A1 (3β,5α)-3-Hydroxy-4,4-dimethylcholesta-8,24-dien-23-one 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-[2acetamido-2-deoxy-β-D-galactopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C62H100N2O26 Powder (CHCl3/MeOH), mp 208–212 °C, [α]D = −7.4° (c = 0.3, MeOH). Source: Sponge Asteropus sarasinosum. Pharm: Cytotoxic; ichthyotoxin. Ref: M. Kobayashi, et al, CPB, 1991, 39, 2867│ H. -S. Lee, et al, JNP, 2000, 63, 915-

O

H O

HO

O

H

OH

HO

BDXYL

OO OH

BDGALA

HO NH HO

O OH

HO

OH

OH

O

O OH BDGLU

HO

BDGLU

O

O

O

O

HN O

BDGLU

OH

5.2 Lanostane Triterpenoids

263

697 Sarasinoside B1 (3β,5α)-3-Hydroxy-4,4-dimethylcholesta-8,24-dien-23-one 3-O-[β-D-glucopyranosyl(1→2)-β-D-xylopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-[2acetamido-2-deoxy-β-D-galactopyranosyl-(1→4)]-β-D-xylopyranoside] Type: Lanostane triterpenoids. C61H98N2O25 Cryst. (MeOH), mp 197–199 °C, [α]D20 = −16° (c = 0.99, MeOH). Source: Sponge Asteropus sarasinosum (Solomon Is.). Pharm: Ichthyotoxin. Ref: I. Kitagawa, et al, CPB, 1987, 35, 5036│ M. Kobayashi, et al, CPB, 1991, 39, 2867│ A. Espada, et al, Tetrahedron, 1992, 48, 8685

O

H O

HO

H

OH

HO

BDXYL

OO OH

BDGALA

O

O

O

O

O

OH OH NH BDGLU H O BDXYL H O H N O O O HO OH O OH

BDGLU

OH

698 Sexangulic acid Type: Lanostane triterpenoids. C30H48O4 Amorphous powder, [α]D24 = +38.7° (c = 0.60, CHCl3). Source: Mangrove Bruguiera sexangula (Hainan province, China). Pharm: Cytotoxic (A549 and HL60, 5 μg/mL, modest). Ref: L. Li, et al, Nat. Prod. Res., 2010, 24, 1044

H

HO

H

HO O

OH

264

5 Triterpenoids

699 Typicoside A1 Type: Lanostane triterpenoids. C55H84O25S Source: Sea cucumber Actinocucumis typica (Vizhinjam coast, Arabian Sea, India). Pharm: Antifungal; haemolytic; cytotoxic. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 301

O O HO

O

S

O

O HO

H

O

H O

O

O

O

H

O OH

O OH OH

O

O OH

OH O HO

O OH

700 Typicoside C1 Type: Lanostane triterpenoids. C54H86O28S2 Source: Sea cucumber Actinocucumis typica (Vizhinjam coast, Arabian Sea, India). Pharm: Markedly less active in all assays. Ref: A. S. Silchenko, et al, Nat. Prod. Commun., 2013, 8, 301 OH O O HO

S

O

O

O HO O

O OH

O OH OH

O

O O HO

S O

O

OH

OH O

HO

O OH

H O

H

O H

5.3 Cycloartane Triterpenoids

265

5.3 Cycloartane Triterpenoids 701 Cycloartane-3,28-disulfate-23-ol Type: Cycloartane triterpenoids. C30H52O9S2 Solid, mp 203–204 °C (dec), [α]D = +20.5° (c = 0.002, MeOH). Source: Green algae Tydemania expeditionis and Tuemoya sp. Pharm: VZV protease inhibitor (IC50 = 4.8 μmol/L); CMV protease inhibitor (IC50 = 6.9 μmol/L). Ref: M. Govindan, et al, JNP, 1994, 57, 74│ A. D. Patil, et al, Nat. Prod. Lett., 1997, 9, 209

H O

HO

OH

H

S

O

O HO

O S

O

H

O

702 Cycloartane-23-one-3β,28-diol 3,28-disulfate Type: Cycloartane triterpenoids. C30H50O9S2 Solid, mp 198–199 °C (dec), [α]D = +23.6° (c = 0.005, MeOH). Source: Green alga Tydemania expeditionis. Pharm: Protein tyrosine kinase pp60 inhibitor. Ref: M. Govindan, et al, JNP, 1994, 57, 74 23

O H O HO

S

O O

O O

S

O

OH

703 Cycloartane-3β,23ξ,28-triol 3,28-disulfate Type: Cycloartane triterpenoids. C30H52O9S2 Solid, mp 203–204 °C (dec), [α]D = +20.5° (c = 0.002, MeOH). Source: Green alga Tydemania expeditionis. Pharm: Protein tyrosine kinase pp60 inhibitor. Ref: M. Govindan, et al, JNP, 1994, 57, 74

266

5 Triterpenoids

23

OH H H

O

O

S

3

O 28

O O O

S

O

O

H

704 Cycloart-24-ene-3β,23R-diol 3-O-sulfate Type: Cycloartane triterpenoids. C30H50O5S White amorph. solid, [α]D27 = +35° (c = 0.24, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 2 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210 23

OH H OH O

S

3

O

O

705 Cycloart-24-ene-23-one-3β,28-diol 3,28-disulfate Type: Cycloartane triterpenoids. C30H48O9S2 Solid, mp 230–232 °C (dec). Source: Green alga Tydemania expeditionis. Pharm: Protein tyrosine kinase pp60 inhibitor. Ref: M. Govindan, et al, JNP, 1994, 57, 74

H

O

H O HO

S O

O O O

O S

OH

706 Cycloart-24-ene-3β,23R,28-triol 3-sulfate Type: Cycloartane triterpenoids. C30H50O6S White amorph. solid, [α]D27 = +35° (c = 0.14, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, substantial activity at 17 μg/mL, IC50 > 10 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

5.3 Cycloartane Triterpenoids

267

OH H OH O

S

O OH

O

707 Cycloart-24-en-23-one-28-sulfate-3-ol Type: Cycloartane triterpenoids. C30H48O6S Amorph. powder, [α]D = +17° (c = 0.23, MeOH). Source: Green alga Tuemoya sp. Pharm: VZV protease inhibitor (IC50 = 4.6 μmol/L); CMV protease inhibitor (IC50 = 6.1 μmol/L). Ref: A. D. Patil, et al, Nat. Prod. Lett., 1997, 9, 209

H

O

H HO O

HO

S

O

H

O

708 3β,28-Dihydroxy-cycloart-24-en-23-one 3-O-sulfate Type: Cycloartane triterpenoids. C30H48O6S White amorph. solid, [α]D23 = +28° (c = 0.12, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 2 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

H

O

H OH O

S O

O OH

709 3β-Hydroxycycloart-24-en-23-one 3-sulfate Type: Cycloartane triterpenoids. C30H48O5S White amorph. solid, [α]D28 = +20° (c = 0.54, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 10 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

268

5 Triterpenoids

H

O

H OH O

S

O

O

710 Methyl 3β,23R-dihydroxycycloart-24-en-28-oate 3-sulfate Type: Cycloartane triterpenoids. C31H50O7S White amorph. solid, [α]D27 = +53° (c = 0.10, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, substantial activity at 17 μg/mL, IC50 > 10 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

OH H OH O

S

O O

O O

711 Methyl 3β,23R-dihydroxy-29-nor-cycloart-24-en-28-oate 3-sulfate Type: Cycloartane triterpenoids. C30H48O7S White amorph. solid, [α]D28 = +38° (c = 0.08, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 1 μg/mL); toxic (brine shrimp, 50 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

H

OH

H OH O

S O

O O

H O

712 Methyl 3β-hydroxy-23-oxocycloart-24-en-28-oate 3-sulfate Type: Cycloartane triterpenoids. C31H48O7S White amorph. solid, [α]D28 = +24° (c = 0.44, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 10 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

5.4 Rearranged Tetranortriterpenoids

269

O H OH O

S

O O

O O

713 Methyl 3β-Hydroxy-23-oxo-29-nor-cycloart-24-en-28-oate 3-sulfate Type: Cycloartane triterpenoids. C30H46O7S White amorph. solid, [α]D28 = +40° (c = 0.03, MeOH). Source: Red alga Tricleocarpa fragilis (Hawaii). Pharm: Cytotoxic (P388, IC50 > 1 μg/mL). Ref: F. D. Horgen, et al, JNP, 2000, 63, 210

H

O

H OH O

S

O O

O O

5.4 Rearranged Tetranortriterpenoids 714 Godavarin A Type: Rearranged tetranortriterpenoids. C32H38O7 Source: Mangrove Xylocarpus moluccensis (seeds, Godavari estuary, Andhra Pradesh, India). Pharm: Antifeedant (modest); insecticidal (coconut pest Brontispa longissima, poor activity). Ref: J. Li, et al, Phytochemistry, 2010, 71, 1917 O

O

H O

O O

H

O

H

O

270

5 Triterpenoids

715 Godavarin D Type: Rearranged tetranortriterpenoids. C32H40O9 Source: Mangrove Xylocarpus moluccensis (seeds, Godavari estuary, Andhra Pradesh, India). Pharm: Antifeedant (modest); insecticidal (coconut pest Brontispa longissima, poor activity). Ref: J. Li, et al, Phytochemistry, 2010, 71, 1917 O

O

H O

O

OH

O O O O

716 2-Hydroxyfissinolide Type: Rearranged tetranortriterpenoids. C29H36O9 Source: Mangrove Xylocarpus moluccensis (extracts of seeds, Andhra Pradesh, India). Pharm: Antifeedant and insecticidal (third-instar larvae of Brontispa longissima, 1.0 mg/mL, antifeedant rate (24 h) = (93.7 ± 5.5)%, antifeedant rate (48 h) = (91.5 ± 3.5)%, corrected mortality (9 d) = (34.4 ± 5.1)%). Ref: J. Li, et al, JNP, 2012, 75, 1277 O

O

H H

O

O

O

O

OH O O

717 6R-Hydroxymexicanolide Type: Rearranged tetranortriterpenoids. C27H32O8 Colorless crystals (CHCl3-MeOH, 1:1), mp 248–250 °C, [α]D25 = −72° (c = 0.27, Me2CO). Source: Mangrove Xylocarpus moluccensis (extracts of seeds, Andhra Pradesh, India). Pharm: Antifeedant and insecticidal (third-instar larvae of Brontispa longissima, 1.0 mg/mL, antifeedant rate (24 h) = (76.6 ± 4.6)%, antifeedant rate (48 h) = (69.3 ± 2.6)%, corrected mortality

5.4 Rearranged Tetranortriterpenoids

271

(9 d) = (20.7 ± 1.3)%). Ref: D. A. Okorie, et al, Phytochemistry, 1968, 7, 1683│ J. Li, et al, JNP, 2012, 75, 1277 O

OH O

O

H H

O

O

O

H O

718 2-Hydroxyxylorumphiin F Type: Rearranged tetranortriterpenoids. C36H50O12 White amorphous powder, [α]D20 = −19° (c = 0.1, MeOH). Source: Mangrove Xylocarpus rumphii (seeds, Kudee I., Thailand). Pharm: Anti-inflammatory (NO production inhibitor, LPS-activated murine macrophage J774.A1 cells, IC50 = 24.5 μmol/L, weak). Ref: C. Sarigaputi, et al, JNP, 2014, 77, 2037 O

O

O

O

H H

O HO O

O

O OH

O

O

719 Moluccensin R Type: Rearranged tetranortriterpenoids. C31H40O10 White amorph. powder, [α]D25 = −77° (c = 2.7, Me2CO). Source: Mangrove Xylocarpus moluccensis (extracts of seeds, Andhra Pradesh, India). Pharm: Antifeedant and insecticidal (third-instar larvae of Brontispa longissima, 1.0 mg/mL, antifeedant rate (24 h) = (69.6 ± 4.1)%, antifeedant rate (48 h) = (62.1 ± 4.3)%, corrected mortality (9 d) = (17.0 ± 5.1)%). Ref: J. Li, et al, JNP, 2012, 75, 1277

272

5 Triterpenoids

O

OH O

O

H H

O

O

O

OH O O

720 Moluccensin S Type: Rearranged tetranortriterpenoids. C32H42O10 White amorph. powder, [α]D25 = −65° (c = 0.28, Me2CO). Source: Mangrove Xylocarpus moluccensis (extracts of seeds, Andhra Pradesh, India). Pharm: Antifeedant and insecticidal (third-instar larvae of Brontispa longissima, 1.0 mg/mL, antifeedant rate (24 h) = (42.3 ± 2.8)%, antifeedant rate (48 h) = (44.1 ± 3.9)%, corrected mortality (9 d) = (48.2 ± 3.2)%). Ref: J. Li, et al, JNP, 2012, 75, 1277 O

OH O

O

H H

O

O

O

OH O O

721 Thaimoluccensin C Type: Rearranged tetranortriterpenoids. C33H40O11 Source: Mangrove Xylocarpus moluccensis (seeds, Phuket province, Southern Thailand). Pharm: NO production inhibitor (stimulated macrophages, modest). Ref: W. Ravangpai, et al, BoMCL, 2011, 21, 4485

5.5 Oleanane Triterpenoids

273

O

O

O

O

H

O

O OH

O O

O O

722 Xylorumphiin I Type: Rearranged tetranortriterpenoids. C37H50O12 White amorphous powder, [α]D20 = +4° (c = 0.1, MeOH). Source: Mangrove Xylocarpus rumphii (seeds, Kudee I., Thailand). Pharm: Anti-inflammatory (NO production inhibitor, LPS-activated murine macrophage J774.A1 cells, IC50 = 31.3 μmol/L, weak). Ref: C. Sarigaputi, et al, JNP, 2014, 77, 2037 O

O

O

O

H

O

O HO O

O OH

O

O

5.5 Oleanane Triterpenoids 723 Acetylenoxolone Glycyrrhetic acetate Type: Oleanane triterpenoids. C32H48O5 mp 245 °C. Source: Stone coral Echinopora lamellosa. Pharm: Antiulcer. Ref: R. Sanduja, et al, J. Heterocycl. Chem., 1984, 21, 845

274

5 Triterpenoids

COOH

O H O

H O

724 Catunaroside A Type: Oleanane triterpenoids. C47H76O18 Source: Mangrove Catunaregam spinosa (stem bark, Sanya, Hainan province, China). Pharm: Antifeedant (second-instar larvae of diamondback moth Plutella xylostella). Ref: G. Gao, et al, Carbohydr. Res., 2011, 346, 2200

HO O

HO HO

OH

H

HO

HO

O O

O HO O OH HO HO

H

O O OH

725 Catunaroside B Type: Oleanane triterpenoids. C48H78O17 Source: Mangrove Catunaregam spinosa (stem bark, Sanya, Hainan province, China). Pharm: Antifeedant (second-instar larvae of diamondback moth Plutella xylostella). Ref: G. Gao, et al, Carbohydr. Res., 2011, 346, 2200

O

HO HO HO

H

HO O

O HO O OH HO

O OH

O OH

O

H

OH

5.5 Oleanane Triterpenoids

275

726 Catunaroside C Type: Oleanane triterpenoids. C54H88O23 Source: Mangrove Catunaregam spinosa (stem bark, Sanya, Hainan province, China). Pharm: Antifeedant (second-instar larvae of diamondback moth Plutella xylostella). Ref: G. Gao, et al, Carbohydr. Res., 2011, 346, 2200 OH

HO HO

HO

OH

O

O

O

H H O

HO

HO HO HO

O

HO O O

O O

OH

OH OH

HO

727 Catunaroside D Type: Oleanane triterpenoids. C53H86O23 Source: Mangrove Catunaregam spinosa (stem bark, Sanya, Hainan province, China). Pharm: Antifeedant (second-instar larvae of diamondback moth Plutella xylostella). Ref: G. Gao, et al, Carbohydr. Res., 2011, 346, 2200

HO

O

HO HO HO

H

HO O HO O OH HO HO

O O O OH

O

H HO HO

O

OH O OH

276

5 Triterpenoids

728 Miliacin 3β-Methoxyolean-18-ene Type: Oleanane triterpenoids. C31H52O Cryst. (Me2CO/C6H6), mp 283 °C, [α]D = +22° (CHCl3), [α]D = +8° (CHCl3). Source: Marine-derived fungus Chaetomium olivaceum (psychrophilic, cold water, sediments, near Paramushir I., among Kuril Is.), initially isolated from seeds of switch-grass Panicum miliaceum, and was later frequently found in higher plants. Pharm: Inducer of hemolysis (erythrocytes, pH7, HC50 = 2 × 10−4 mol/L). Ref: O. F. Smetanina, et al, Russ. Chem. Bull., 2001, 50, 2463│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

H

H O

H

5.6 Malabaricane and Isomalabaricane Triterpenoids 729 Globostellatic acid A (3α,13Z,16E,20(22)E,23E)-3-Acetoxy-25-hydroxy-12,15-dioxo-13,16,20(22),23-isomalabaricatetraen-29-oic acid Type: Malabaricane and isomalabaricane triterpenoids. C32H44O7 Yellow amorph. solid, [α]D23 = −45.7° (c = 0.35, MeOH). Source: Sponge Stelletta globostellata (yield = 2.1 × 10-5% ww, Japan). Pharm: Cytotoxic (P388, IC50 = 0.1 μg/mL). Ref: G. Ryu, et al, JNP, 1996, 59, 512 O O O

H O

OH

H

O O

H

730 Globostellatic acid B Type: Malabaricane and isomalabaricane triterpenoids. C33H48O7 Pale yellow amorph. Solid, [α]D23 = +126.6° (c = 0.54, MeOH). Source: Sponge Stelletta globostellata (yield = 1.2 × 10-5% ww, Japan). Pharm: Cytotoxic (P388, IC50 = 0.1 μg/mL). Ref: G. Ryu, et al, JNP, 1996, 59, 512

5.6 Malabaricane and Isomalabaricane Triterpenoids

277

O O 22

O

OH

H O

H

O O

H

731 Globostellatic acid C Type: Malabaricane and isomalabaricane triterpenoids. C33H48O7 Yellow amorph. Solid, [α]D23 = +15.2° (c = 0.82, MeOH). Source: Sponge Stelletta globostellata (yield = 8.0 × 10-6% ww, Japan). Pharm: Cytotoxic (P388, IC50 = 0.46 μg/mL). Ref: G. Ryu, et al, JNP, 1996, 59, 512 O O 24

O

H O

OH

H

O O

H

732 Globostellatic acid D Type: Malabaricane and isomalabaricane triterpenoids. C31H46O6 Yellow amorph. Solid, [α]D23 = +135.7° (c = 1.1, MeOH). Source: Sponge Stelletta globostellata (yield = 1.8 × 10–5% ww, Japan). Pharm: Cytotoxic (P388, IC50 = 0.1 μg/mL). Ref: G. Ryu, et al, JNP, 1996, 59, 512 O O

H HO

H O

O

OH

H

733 Globostelletin A Type: Malabaricane and isomalabaricane triterpenoids. C19H28O5 Achroic oil, [α]D = −17.9° (c = 0.7, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, Bel7402, BGC823, A549, A2780, all IC50s > 50 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639

278

5 Triterpenoids

O HO

O

O

O H

734 Globostelletin B Type: Malabaricane and isomalabaricane triterpenoids. C20H28O4 Light yellow oil, [α]D20 = 33.5° (c = 1.0, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, Bel7402, BGC823, A549, A2780, all IC50s > 50 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639 O

O OH

H O

H

735 Globostelletin C Type: Malabaricane and isomalabaricane triterpenoids. C22H30O3 Light yellow oil, [α]D20 = −203.6° (c = 0.11, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, IC50 = 22.03 μmol/L; Bel7402, IC50 = 31.24 μmol/L; BGC823, IC50 = 28.77 μmol/L; A549, IC50 > 50 μmol/L; A2780, IC50 = 9.04 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639 O

H O

H

H

O

736 Globostelletin D Type: Malabaricane and isomalabaricane triterpenoids. C22H30O3 Light yellow oil, [α]D20 = −203.6° (c = 0.11, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, IC50 = 22.03 μmol/L; Bel7402, IC50 = 31.24 μmol/L; BGC823, IC50 = 28.77 μmol/L; A549, IC50 > 50 μmol/L; A2780, IC50 = 9.04 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639

5.6 Malabaricane and Isomalabaricane Triterpenoids

279

O

O

H

H O

H

737 Globostelletin E Type: Malabaricane and isomalabaricane triterpenoids. C22H30O4 Light yellow oil, [α]D20 = 12.3° (c = 0.3, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, Bel7402, BGC823 and A549, all IC50s > 50 μmol/L; A2780, IC50 = 17.36 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639 O

H O

H

O

HO

738 Globostelletin F Type: Malabaricane and isomalabaricane triterpenoids. C22H30O4 Light yellow oil, [α]D20 = 12.3° (c = 0.30, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, Bel7402, BGC823, A549, A2780, all IC50s > 50 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639 O

O OH

H O

H

739 Globostelletin G Type: Malabaricane and isomalabaricane triterpenoids. C25H34O4 Yellow oil, [α]D20 = −6.0° (c = 0.25, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, Bel7402, BGC823 and A549, all IC50s > 50 μmol/L; A2780, IC50 = 15.37 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639

280

5 Triterpenoids

O 13E

H O

H O

HO

740 Globostelletin H Type: Malabaricane and isomalabaricane triterpenoids. C27H36O4 Yellow oil, [α]D20 = −50.0° (c = 0.10, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, Bel7402, BGC823 and A549, all IC50s > 50 μmol/L; A2780, IC50 = 8.19 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639 O

H O

H

HO

O

741 Globostelletin I Type: Malabaricane and isomalabaricane triterpenoids. C27H36O4 Yellow oil, [α]D20 = −206.2° (c = 0.08, MeOH). Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, Bel7402, BGC823 and A549, all IC50s > 50 μmol/L; A2780, IC50 = 7.66 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639 HO O

O

H O

H

742 29-Hydroxystelliferin A Type: Malabaricane and isomalabaricane triterpenoids. C32H48O5 Yellow solid, [α]D25 = −37° (c = 0.1, MeOH). Source: Sponge Jaspis sp. (near Tonga, Japan). Pharm: Cytotoxic (mixture with 13E-29-Hydroxystelliferin A: MALME-3M, IC50 = 0.11 μg/mL; Molt4, IC50 = 1.62 μg/mL). Ref: K. M. Meragelman, et al, JNP, 2001, 64, 389

5.6 Malabaricane and Isomalabaricane Triterpenoids

281

O OH O

H O HO

H

743 29-Hydroxystelliferin E Type: Malabaricane and isomalabaricane triterpenoids. C34H50O6 Yellow solid, [α]D25 = −40° (c = 0.33, MeOH). Source: Sponge Jaspis sp. (near Tonga, Japan). Pharm: Cytotoxic (mixture with 13E-29-Hydroxystelliferin E: MALME-3M, IC50 = 2.27 μg/mL; Molt4, IC50 = 19.54 μg/mL). Ref: K. M. Meragelman, et al, JNP, 2001, 64, 389 O O O O

H O

H

HO

744 3-epi-29-Hydroxystelliferin E Type: Malabaricane and isomalabaricane triterpenoids. C34H50O6 Yellow solid, [α]D25 = −133° (c = 0.69, MeOH). Source: Sponge Jaspis sp. (near Tonga, Japan) and Stelletta globostellata. Pharm: Cytotoxic (mixture with 13E-3-epi-29-Hydroxystelliferin E: MALME-3M, IC50 = 1.20 μg/mL; Molt4, IC50 = 16.62 μg/mL). Ref: K. M. Meragelman, et al, JNP, 2001, 64, 389│ N. Oku, et al, JNP, 2000, 63, 205 O O O O

H

3

O HO

H

745 Jaspiferal A Type: Malabaricane and isomalabaricane triterpenoids. C27H36O5 Oil (Me ester), [α]D22 = −18.9° (c = 0.09, C6H6) (Me ester). Source: Sponge Jaspis stellifera (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 3.8 μg/mL; KB, IC50 > 10 μg/mL). Ref: J. Kobayashi, et al, Tetrahedron, 1996, 52, 5745

282

5 Triterpenoids

O O

HO

H

13Z

H H

O OH

746 Jaspiferal B Type: Malabaricane and isomalabaricane triterpenoids. C27H36O5 Oil (Me ester), [α]D22 = −123.7° (c = 0.07, C6H6) (Me ester). Source: Sponge Jaspis stellifera (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 3.8 μg/mL; KB, IC50 > 10 μg/mL). Ref: J. Kobayashi, et al, Tetrahedron, 1996, 52, 5745 O

O

13E

H HO

H

13

H

O

OH

747 Jaspiferal C Type: Malabaricane and isomalabaricane triterpenoids. C25H34O5 Oil (Me ester), [α]D19 = −24° (c = 0.14, C6H6) (Me ester). Source: Sponge Jaspis stellifera (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 4.3 μg/mL; KB, IC50 > 10 μg/mL). Ref: J. Kobayashi, et al, Tetrahedron, 1996, 52, 5745 O O 13

H

H HO

H

O OH

748 Jaspiferal D Type: Malabaricane and isomalabaricane triterpenoids. C25H34O5 Oil (Me ester), [α]D19 = −85° (c = 0.14, C6H6) (Me ester). Source: Sponge Jaspis stellifera (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 4.3 μg/mL; KB, IC50 > 10 μg/mL). Ref: J. Kobayashi, et al, Tetrahedron, 1996, 52, 5745

5.6 Malabaricane and Isomalabaricane Triterpenoids

283

O

H HO O

O

13

H

H OH

749 Jaspiferal E Type: Malabaricane and isomalabaricane triterpenoids. C22H30O5 Oil (Me ester), [α]D18 = −51° (c = 0.18, C6H6) (Me ester). Source: Sponge Jaspis stellifera (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 3.1 μg/mL; KB, IC50 = 5.5 μg/mL); antifungal (mixture with Jaspiferal F, Trichophyton mentagrophytes, MIC = 50 μg/mL). Ref: J. Kobayashi, et al, Tetrahedron, 1996, 52, 5745 O O H

13

H HO

H

O OH

750 Jaspiferal F Type: Malabaricane and isomalabaricane triterpenoids. C22H30O5 Oil (Me ester), [α]D18 = −116° (c = 0.12, C6H6) (Me ester). Source: Sponge Jaspis stellifera (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 3.1 μg/mL; KB, IC50 = 5.5 μg/mL); antifungal (mixture with Jaspiferal E, Trichophyton mentagrophytes, MIC = 50 μg/mL). Ref: J. Kobayashi, et al, Tetrahedron, 1996, 52, 5745 O

13

O

H HO

H

O OH

H

284

5 Triterpenoids

751 Jaspiferal G Type: Malabaricane and isomalabaricane triterpenoids. C20H28O5 Powder, mp 145–147 °C, [α]D20 = −54° (c = 0.3, CHCl3/MeOH). Source: Sponge Jaspis stellifera (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 0.54 μg/mL; KB, IC50 = 1.8 μg/mL); antifungal (Cryptococcus neoformans, MIC = 50 μg/mL; Trichophyton mentagrophytes, MIC = 12.5 μg/mL); antibacterial (Sarcina lutea, MIC = 50 μg/mL). Ref: J. Kobayashi, et al, Tetrahedron, 1996, 52, 5745 O

H HO

H

H

O

O

OH

752 Jaspolide F Type: Malabaricane and isomalabaricane triterpenoids. C25H34O4 Pale yellow solid, [α]D25 = −14.9° (c = 0.01, Me2CO). Source: Sponges Rhabdastrella globostellata (Hainan I., South China Sea) and Jaspis sp. Pharm: Cytotoxic (HCT8, Bel7402, BGC823 and A549, all IC50s > 50 μmol/L; A2780, IC50 = 7.92 μmol/L). Ref: S. Tang, et al, CPB, 2006, 54, 4│ J. Li, et al, BoMC, 2010, 18, 4639 O O

OH

13Z

H O

H

753 Stellettin F Rhabdastrellic acid A Type: Malabaricane and isomalabaricane triterpenoids. C30H40O4 Yellow cryst. (C6H6/Me2CO), [α]D = −61.6° (c = 0.6, Me2CO). Source: Sponges Rhabdastrella globostellata (Hainan I., South China Sea), Stelletta sp. and Rhabdastrella globostellata. Pharm: Cytotoxic (HCT8, IC50 > 50 μmol/L; Bel7402, IC50 = 21.18 μmol/L; BGC823, IC50 > 50 μmol/L; A549, IC50 > 50 μmol/L; A2780, IC50 = 4.23 μmol/L); cytotoxic (HL60, IC50 = 6.7 μmol/L, induces apoptosis of HL60 cells in M/G2 phase). Ref: J. L. McCormick, et al, JNP, 1996, 59, 1047│ Z. J. Rao, et al, Nat. Prod., 1997, 60, 1163│ J. Li, et al, BoMC, 2010, 18, 4639

5.6 Malabaricane and Isomalabaricane Triterpenoids

285

O 13E

H O

O

H

OH

754 Stellettin A Type: Malabaricane and isomalabaricane triterpenoids. C30H38O4 Yellow needles (EtOAc/petrol), mp 234–235 °C, [α]D20 = +28.8° (c = 0.16, MeOH). Source: Sponges Stelletta globostellata (Malaysia), Stelletta tenuis (China), Stelletta sp. (Somalia), Rhabdastrella globostellata and Geodia japonica. Pharm: Cytotoxic (P388, GI50 = 0.012 μg/mL; BXPC3, GI50 = 0.078 μg/mL; MCF7, GI50 = 0.752 μg/mL). Ref: T. McCabe, et al, Tet. Lett., 1982, 23, 3307│ J. Y. Su, et al, JNP, 1994, 57, 1450│ G. R. Pettit, et al, JNP 2008, 71, 438 O O O

O

755 Stellettin B Type: Malabaricane and isomalabaricane triterpenoids. C30H38O4 Unstable yellow prisms (CH2Cl2/Et2O), mp 258–260 °C, mp266–268 °C, [α]D25 = +87° (c = 0.08, CHCl3). Source: Sponges Stelletta globostellata (Kudat, Malaysia, 1991), Stelletta sp. and Jaspis stellifera. Pharm: Cytotoxic (P388, GI50 = 0.037 μg/mL). Ref: G. R. Pettit, et al, JNP 2008, 71, 438│ W. -J. Lan, et al, Gaodeng Xuexiao Huaxue Xuebao, 2005, 26, 2270 O

O O

O

286

5 Triterpenoids

756 Stellettin C Type: Malabaricane and isomalabaricane triterpenoids. C32H42O5 Yellow solid, [α]D = −250° (c = 0.51, CHCl3). Source: Sponges Rhabdastrella globostellata (Hainan I., South China Sea) and Stelletta sp. Pharm: Cytotoxic (HL60, IC50 = 3.6 μmol/L; HeLa, IC50 = 16 μmol/L). Ref: J. L. McCormick,et al, JNP 1996, 59, 1047│ J. Li, et al, BoMC, 2010, 18, 4639 O 13E

O

H O

H O O

757 Stellettin D Type: Malabaricane and isomalabaricane triterpenoids. C32H42O5 Yellow solid, [α]D = −19.4° (c = 1, CHCl3). Source: Sponges Rhabdastrella globostellata (Hainan I., South China Sea) and Stelletta sp. Pharm: Cytotoxic (HL60, IC50 = 0.01 μmol/L; HeLa, IC50 = 7.5 μmol/L). Ref: J. L. McCormick,et al, JNP 1996, 59, 1047│ J. Li, et al, BoMC, 2010, 18, 4639

O

O

O 13Z

O

H O

H

758 Stellettin E Type: Malabaricane and isomalabaricane triterpenoids. C30H40O4 Source: Sponge Rhabdastrella globostellata (Hainan I., South China Sea). Pharm: Cytotoxic (HCT8, IC50 > 50 μmol/L; Bel7402, IC50 = 13.70 μmol/L; BGC823, IC50 > 50 μmol/L; A549, IC50 = 18.61 μmol/L; A2780, IC50 < 0.5 μmol/L). Ref: J. Li, et al, BoMC, 2010, 18, 4639│ J. L. McCormick,et al, JNP 1996, 59, 1047

5.7 Raspacionins and Sodwanones Triterpenoids

287

O OH

O 13Z

H O

H

759 Stelliferin G Type: Malabaricane and isomalabaricane triterpenoids. C32H48O5 Yellow solid, [α]D25 = −17° (c = 0.02, MeOH). Source: Sponge Jaspis sp. (near Tonga, Japan). Pharm: Cytotoxic (mixture with 13E-Stelliferin G: MALME-3M, IC50 = 0.23 μg/mL; Molt4, IC50 = 4.11 μg/mL). Ref: K. M. Meragelman, et al, JNP, 2001, 64, 389 O O O

H HO

H

HO

5.7 Raspacionins and Sodwanones Triterpenoids 760 Raspacionin Type: Raspacionins and sodwanones triterpenoids. C34H56O7 Prisms (heptane), mp 188–189 °C, [α]D = +31.4° (c = 1.5, CHCl3). Source: Sponges Raspaciona aculeata (Mediterranean) and Raspaciona larvacid. Pharm: Allelochemical, larvicide. Ref: G. Cimino, et al, Tetrahedron, 1992, 48, 9013│ G. Cimino, et al, JNP, 1993, 56, 534; 1622; 1994, 57, 784│ M. L. Ciavatta, et al, Tetrahedron, 2002, 58, 4943 O OH O O

H

10

28

4

21

O H

15

O O

288

5 Triterpenoids

761 Sodwanone A Type: Raspacionins and sodwanones triterpenoids. C30H44O6 Cryst., mp 253 °C, [α]D = −9° (c = 0.1, CHCl3). Source: Sponges Axinella weltneri (South Africa) and Ptilocaulis spiculifer. Pharm: Cytotoxic. Ref: A. Rudi, et al, Tet. Lett., 1993, 34, 3943│ A. Rudi, et al, JNP, 1994, 57, 1416 O

OH O OH O

O

762 Sodwanone G Type: Raspacionins and sodwanones triterpenoids. C30H42O6 Crystals (MeOH), mp 245 °C, [α]D = −14.5° (c = 0.9, CHCl3). Source: Sponge Axinella weltneri (South Africa). Pharm: Cytotoxic (P388, IC50 = 2.0 μg/mL; A549, IC50 = 0.2 μg/mL; HT29, IC50 = 2.0 μg/mL; MEL28, IC50 = 2.0 μg/mL). Ref: A. Rudi, et al, JNP, 1995, 58, 1702 O

O

O OH H O O

763 Sodwanone H Type: Raspacionins and sodwanones triterpenoids. C30H48O4 Amorphous powder, [α]D = −8° (c = 0.1, CHCl3). Source: Sponge Axinella weltneri (South Africa). Pharm: Cytotoxic (P388, IC50 = 10.5 μg/mL; A549, IC50 = 0.02 μg/mL; HT29, IC50 = 10.5 μg/mL; MEL28, IC50 = 10.5 μg/mL). Ref: A. Rudi, et al, JNP, 1995, 58, 1702 O

OH

O H

H O

5.8 Zoanthamine Triterpenoids

289

764 Sodwanone I Type: Raspacionins and sodwanones triterpenoids. C30H50O5 Oil, [α]D = +2° (c = 0.2, CHCl3). Source: Sponge Axinella weltneri (South Africa). Pharm: Cytotoxic (P388, IC50 = 20 μg/mL; A549, IC50 = 20 μg/mL; HT29, IC50 = 20 μg/mL; MEL28, IC50 = 20 μg/mL). Ref: A. Rudi, et al, JNP, 1995, 58, 1702 OH O

O

O

O

H

765 Sodwanone M Type: Raspacionins and sodwanones triterpenoids. C30H50O5 Oil, [α]D = +18° (c = 0.1, CHCl3). Source: Sponge Axinella weltneri (Comoros island). Pharm: Cytotoxic (P388, 1 μg/mL). Ref: A. Rudi, et al, JNP, 1997, 60, 700 O O O

O

OH

5.8 Zoanthamine Triterpenoids 766 Cyclozoanthamine Type: Zoanthamine triterpenoids. C30H41NO6 Collorless oil, [α]D = −14.8° (c = 0.42, CHCl3). Source: Zoanthid Zoanthus sp. (Ayamaru coast of Amami Is., Japan). Pharm: Cytotoxic (P388, IC50 = 2.6 μg/mL). Ref: S. Fukuzawa, et al, Heterocycl. Commun., 1995, 1, 207│ M. Kuramoto, et al, Bull. Chem. Soc. Jpn., 1998, 71, 771│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39

290

5 Triterpenoids

O

H

O H

H

OH

O

N

O

O

767 28-Deoxyzoanthenamine Type: Zoanthamine triterpenoids. C30H39NO5 mp 305–307 °C, [α]D = +216° (c = 3.7, CHCl3). Source: Zoanthid Zoanthus sp. Pharm: Anti-inflammatory; analgesic. Ref: C. B. Rao, et al, Heterocycles, 1989, 28, 103 O

H

O O

20

28

22

H

H

O

N O

768 22-epi-28-Deoxyzoanthenamine Type: Zoanthamine triterpenoids. C30H39NO5 Oil, [α]D = +85° (c = 2.36, CHCl3). Source: Zoanthid Zoanthus spp. Pharm: Anti-inflammatory; analgesic. Ref: C. B. Rao, et al, Heterocycles, 1989, 28, 103 O

H

O O

20

28

22

H

H N O

O

5.8 Zoanthamine Triterpenoids

291

769 Oxyzoanthamine 26-Hydroxyzoanthamine Type: Zoanthamine triterpenoids. C30H41NO6 Collorlessoil, [α]D = +5.3° (c = 0.38, CHCl3). Source: Zoanthid Zoanthus sp. (Ayamaru coast of Amami Is., Japan). Pharm: Cytotoxic (P388, IC50 = 7.0 μg/mL); IL-6 production inhibitor. Ref: S. Fukuzawa, et al, Heterocycl. Commun., 1995, 1, 207│ M. Kuramoto, et al, Bull. Chem. Soc. Jpn., 1998, 71, 771│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39 OH

O 17 14

26

H 13

18

O

19

H

H N

O

O

O

770 epi-Oxyzoanthamine 26-Hydroxy-19-epi-zoanthamine Type: Zoanthamine triterpenoids. C30H41NO6 Amorph. solid, [α]D25 = −17.5° (c = 0.24, CHCl3). Source: Zoanthid Zoanthus sp. (Tenerife). Pharm: Osteoporosis drug. Ref: A. H. Daranas, et al, Tetrahedron, 1998, 54, 7891; 1999, 55, 5539 O

OH H

17 14

26

13

18

O

19

H

H N

O

O

O

771 Zoanthamide Type: Zoanthamine triterpenoids. C30H37NO7 mp 278–280 °C, [α]D = +133° (c = 0.83, CHCl3). Source: Zoanthid Zoanthus sp. Pharm: Anti-inflammatory. Ref: C. B. Rao, et al, JOC, 1985, 50, 3757│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39

292

5 Triterpenoids

O

H

O O

H

O

O

H

O N O

772 Zoanthamine Type: Zoanthamine triterpenoids. C30H41NO5 mp 306–308 °C, [α]D = +18° (c = 0.48, CHCl3). Source: Zoanthid Zoanthus sp. (India), zoanthid Zoanthus sp. (Ayamaru coast of Amami Is., Japan). Pharm: Cytotoxic; anti-inflammatory; IL-6 production inhibitor. Ref: C. B. Rao, et al, JACS, 1984, 106, 7983│ S. Fukuzawa, et al, Heterocycl. Commun., 1995, 1, 207│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39│ D. C. Behenna, et al, Angew. Chem., Int. Ed., 2008, 47, 2365 O

26

H

17 14

18

13

O

19

H

H

N

O

O

O

773 Zoanthenamine Type: Zoanthamine triterpenoids. C30H39NO6 Powder, mp 238–240 °C. Source: Zoanthid Zoanthus sp. Pharm: Anti-inflammatory. Ref: C. B. Rao, et al, JOC, 1985, 50, 3757│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39 O

H

O

OH O

20

28

22

H

H N O

O

5.9 Other Triterpenoids

293

774 Zooxanthellamine Type: Zoanthamine triterpenoids. C30H45NO5 Solid, mp > 300 °C, [α]D20 = +40° (c = 0.05, MeOH). Source: Dinoflagellate Symbiodinium sp. Y-6 from flatworm Amphiscolops sp. Pharm: Toxin. Ref: C. B. Rao, et al, JACS, 1984, 106, 7983│ H. Nakamura, et al, Bull. Chem. Soc. Jpn., 1998, 71, 781│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39 H

O

HO

H H N

O

O

O

5.9 Other Triterpenoids 775 Fusidic acid Fusidin; Antibiotic SQ 16603 Type: Protostane and fusidane triterpenoids. C31H48O6 Cryst. (Et2O), mp 192–193 °C, [α]D20 = −9° (c = 1, CHCl3). Source: Marine-derived fungus Stilbella aciculosa. Pharm: Antibacterial (gram-positive bacteria); anti-HIV. Ref: J. J. Czajkowski, Antimicrob. Chemother., 1989, 23, 15│ L. J. Verbist, Antimicrob. Chemother., (Suppl. B), 1990, 25, 1│ T. A. Kuznetsova, et al, Biochem. Syst. Ecol., 2001, 29, 873 O H

HO

OH O

H HO

O

H

776 Helvolic acid Fumigacin Type: Protostane and fusidane triterpenoids. C33H44O8 Needles (MeOH), mp 215 °C, [α]D25 = −121° (c = 1, CHCl3). Source: Marine-derived fungus Aspergillus sydowi PFW1-13 (from driftwood sample, China). Pharm: Antibacterial (disk diffusion method, Escherichia coli, MIC = 87.92 μmol/L; Bacillus subtilis, MIC = 21.98 μmol/L; Micrococcus lysoleikticus, MIC = 10.99 μmol/L); phytotoxic; Antibacterial

294

5 Triterpenoids

(Staphylococcus spp., Streptococcus spp., Micrococcus spp., Clostridium spp., Pseudomonas spp., Myobacterium spp., Shigella spp., Salmonella spp., Corynebacterium spp.); LD50 (mus, ipr) = 400 mg/kg; LD50 (mus, orl) = 1000 mg/kg. Ref: J. S. -M. Tschen, et al, Bot. Bull. Acad. Sinica, 1997, 38, 251│ M. Zhang, et al, JNP, 2008, 71, 985 O OH

H

O O

H O

H

O O O

777 25-Hydroxy-24,25-Dihydrohelvolic acid (4S,5S,6S,8S,9S,10R,13R,14S,16S,17Z)-6β,16β-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid Type: Protostane and fusidane triterpenoids. C33H46O9 White needles, mp 206–208 °C, [α]D26 = −118.9° (c = 0.07, CHCl3). Source: Marine-derived fungus Aspergillus sydowi PFW1-13 (from driftwood sample, China). Pharm: Antibacterial (disk diffusion method, Escherichia coli, MIC = 10.65 μmol/L; Bacillus subtilis, MIC = 5.33 μmol/L; Micrococcus lysoleikticus, MIC = 10.65 μmol/L). Ref: M. Zhang, et al, JNP, 2008, 71, 985 O H

HO

OH O O

H O

H

O O O

778 Lovenone Type: Cucurbitane triterpenoids. C29H48O4 Glass, [α]D = −38° (CHCl3). Source: Nudibranch Adalaria loveni (psychrophilic, cold water, skin extract). Pharm: Cytotoxic (HEY, (ED50 = 11.l μg/mL); U373, ED50 = 11 μg/mL). Ref: E. I. Graziani, et al, Tet. Lett., 1995, 36, 1763│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

5.9 Other Triterpenoids

295

OH

H HO O O

779 7-Deacetylgedunin Type: Ring-cleaved tetranortriterpenoids. C26H32O6 Source: Mangrove Xylocarpus moluccensis (seeds, Phuket province, Southern Thailand). Pharm: NO production inhibitor (stimulated macrophages, active). Ref: B. Banerji, et al, Fitoterapia, 1984, 55, 3 O

O O

O O

OH

780 Thaimoluccensin A Type: Ring-cleaved tetranortriterpenoids. C27H36O8 Source: Mangrove Xylocarpus moluccensis (seeds, Phuket province, Southern Thailand). Pharm: NO production inhibitor (stimulated macrophages, modest). Ref: W. Ravangpai, et al, BoMCL, 2011, 21, 4485 O

O

H OH

HO

O O

O

O

781 Ursolic acid 3β-Hydroxy-12-ursen-28-oic acid Type: Ursane triterpenoids. C30H48O3 Needles (EtOH), cryst. (Et2O), mp 291 °C, [α]D = +66° (EtOH). Source: An unidentified marine alga (family Cladophorace, Black Sea), widely distributed in plants, e.g. Labiatae spp., Apocynaceae spp., Rosaceae spp. and Oleaceae spp., first isol. in 1854 from Arctostaphylos uva-ursi. Pharm: Cytotoxic (P388, GI50 > 1 μg/mL); possesses angiogenesis inhibitor; protein kinase C inhibitor; HIV-1 protease inhibitor; antiulcer. Ref: G. R. Pettit, et al, JNP 2008, 71, 438│ CRC Press, DNP on DVD, 2012, version 20.2

296

5 Triterpenoids

O

H OH HO

782 Limatulone meso-Limatulone Type: Miscellaneous triterpenoids. C30H46O4 Rods, mp 95–97 °C. Source: Pulmonate limpet Collisella limatula [Syn. Achmeia limatula]. Pharm: Ichtyotoxin, antifeedant (fish). Ref: K. F. Albizati, et al, JOC, 1985, 50, 3428│ K. Mori, et al, Nat. Prod. Lett., 1992, 1, 59│ K. Mori, et al, JCS Perkin I, 1993, 169

O

OH

OH

O

783 (+)-Testudinariol A Type: Miscellaneous triterpenoids. C30H46O4 [α]D25 = +15.2° (c = 0.10, CHCl3). Source: Notapsid Pleurobranchus testudinarius (skin and mucus secretion, Mediterranean). Pharm: Ichthyotoxin. Ref: Spinella, et al, Tetrahedron, 1997, 53, 16891│ H. Takikawa, et al, Tet. Lett., 2001, 42, 1527│ M. Yoshida, et al, J. Chem. Soc. Perkin Trans. 1, 2001, 1007│ H. Hioki, et al, Chem. Lett., 2001, 898

H

H H OH

O

O

H HO

5.9 Other Triterpenoids

297

784 (+)-Testudinariol B Type: Miscellaneous triterpenoids. C30H46O4 [α]D25 = +15.0° (c = 0.05, CHCl3). Source: Notapsid Pleurobranchus testudinarius (skin and mucus secretion, Mediterranean). Pharm: Ichthyotoxin. Ref: Spinella, et al, Tetrahedron, 1997, 53, 16891│ H. Takikawa, et al, Tet. Lett., 2001, 42, 1527│ M. Yoshida, et al, J. Chem. Soc. Perkin Trans. 1, 2001, 1007│ H. Hioki, et al, Chem. Lett., 2001, 898

H

H H OH

O

O

H HO

6 Polyterpenoids and Meroterpenoids 6.1 Tetraterpenoids 785 (3S,3’R)-Adonixanthin-β-D-glucoside Type: Tetraterpenoids. C46H64O8 Source: Marine bacterium Agrobacterium aurantiacum. Pharm: Antioxidant; enhances production of antibody. Ref: A. Yokoyama, et al, JNP, 1995, 58, 1929 OH

O

HO HO

OH

O O

OH

786 (3S,3’S)-Astaxanthin 3,3′-Dihydroxy-β,β-carotene-4,4′-dione Type: Tetraterpenoids. C40H52O4 mp 223–225 °C. Source: Red alga Haematococcus pluvialis (up to 7% dw; 75% total). Pharm: Antioxidant (reactive oxygen species 1O2 quencher; radicals O2•−, H2O2, HO• scavenging; reactive oxygen species (ROS), reactive nitrogen species (RNS) and reactive chlorous species (RCS) quencher (NO, LOOH, ONOO−, HOCl); chain-breaking antioxidant; lipid peroxidation inhibitor; inhibits hallmarkers). Ref: CRC Press, DNP in DVD, 2012, version 20.2│ M. F. J. Raposo, et al, Mar. Drugs, 2015, 13, 5128 (rev)

https://doi.org/10.1515/9783110655155-004

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6 Polyterpenoids and Meroterpenoids

HO O

O OH

787 (3S,3’S)-Astaxanthin β-D-glucoside Type: Tetraterpenoids. C46H62O9 Source: Marine bacterium Agrobacterium aurantiacum. Pharm: Antioxidant; enhances production of antibody. Ref: A. Yokoyama, et al, JNP, 1995, 58, 1929 OH O O

HO HO

OH

O

O OH

788 Canthaxanthin β,β-Carotene-4,4′-dione Type: Tetraterpenoids. C40H52O2 Purple cryst. (C6H6/MeOH), mp 218 °C. Source: Green alga Coelastrella striolata var. multistriata (4.75% dw).

6.1 Tetraterpenoids

301

Pharm: Antioxidant (reactive oxygen species 1O2 quencher). Ref: CRC Press, DNP in DVD, 2012, version 20.2│ M. F. J. Raposo, et al,Mar. Drugs, 2015, 13, 5128 (rev) O

O

789 β-Carotene β,β-Carotene Type: Tetraterpenoids. C40H56 Air-sensitive deep purple prisms (C6H6/ MeOH); red rhombs. (petrol), mp 183 °C. Source: Green alga Dunaliella salina (10%– 13% dw, growing in highly saline medium to produce β-Carotene), green alga Chlorella zofingiensis (total carotenoids = 0.9% dw, in which β-Carotene is 50%), cyanobacterium Arthrospira sp. [Syn. Spirulina sp.] (80% total carotenoids), occurs in marine organisms, e.g. sponges, esp. of the Poecilosclerida and Axinellida, widespread in plant and animal kingdoms. Pharm: Antioxidant (reactive oxygen species 1O2 quencher; radicals NO2, ONOOH and ONOO− scavenger; inhibits Na+/K+-ATPase; stimulates catalase and GS transferase). Ref: CRC Press, DNP in DVD, 2012, version 20.2│ M. F. J. Raposo, et al,Mar. Drugs, 2015, 13, 5128 (rev)

790 Cucumariaxanthin A (9Z,9‘Z)-5,5‘,6,6‘-Tetrahydro-β,β-carotene-4,4‘-dione Type: Tetraterpenoids. C40H56O2 Deep orange needles. Source: Sea cucumber Cucumaria japonica. Pharm: EBV activation inhibitor. Ref: M. Tsushima, et al, JNP, 2001, 64, 1139 O

H 9'Z 9Z

H

302

6 Polyterpenoids and Meroterpenoids

791 Cucumariaxanthin B (9Z,9‘Z)-5,5‘,6,6‘-Tetrahydro4‘-hydroxy–β,β-caroten-4-one Type: Tetraterpenoids. C40H58O2 Deep orange needles. Source: Sea cucumber Cucumaria japonica. Pharm: EBV activation inhibitor. Ref: M. Tsushima, et al, JNP, 2001, 64, 1139 O

H 9'Z 9Z

H

OH

792 Cucumariaxanthin C (9Z,9‘Z)-5,5‘,6,6‘-Tetrahydro-β,β-carotene-4,4‘-diol Type: Tetraterpenoids. C40H60O2 Deep orange needles. Source: Sea cucumber Cucumaria japonica. Pharm: EBV activation inhibitor. Ref: M. Tsushima, et al, JNP, 2001, 64, 1139 HO

H 9'Z 9Z

OH

793 Fucoxanthin Fucoxanthol Type: Tetraterpenoids. C42H58O6 Red-brown prisms (MeOH), mp 158–159 °C, mp 168 °C, [α]18 = +73.5° (CHCl3). Source: Brown algae Sporochnus comosus (Shaw Island, Queensland), Fucus virsoides, Colpomenia peregrine, Hijikia fusiformis (Japanese edible seaweed, Fucoxanthin is major antioxidant), Undaria pinnatifida (edible) and Petalonia binghamiae, red algae Polysiphonia nigrescens and Ceramium rubrum, diatoms Phaeodactylum tricornutum (1.65% dw), Isochrysis aff. galbana (1.8% dw), Cylindrotheca closterium (0.52% dw) and Odontella aurita (up to 2.2% dw). Pharm: Cytotoxic (SF268, GI50 = 12 μmol/L, MCF7, GI50 = 8 μmol/L, H460, GI50 = 14 μmol/L, HT29, GI50 = 17 μmol/L, CHO-K1, GI50 = 12 μmol/L); antioxidant

6.1 Tetraterpenoids

303

(hydroxyl and superoxide radical scavenger, IC50 = 0.14–2.5 mg/mL); antioxidant (reactive oxygen species 1O2 quencher radicals scavenging (O2•−, HO•, ONOO−, HOCl, DPPH•, etc, Na+/K+-ATPase inhibitor, stimulates catalase and glutathione transferase) (Raposo, 2015); anti-obesity (through UCP1 expression in white adipose tissues) (Maeda, 2005); anti-obesity and anti-diabetic (high-fat diet mice model, suppression of adipose tissue and body weight gain and reduction of MCP-1 mRNA expressions) (Maeda, 2009); anti-obesity (diabetic KK-Ay mice model, •suppression of white adipose tissue weight gain) (Hosokawa, 2010); anti-obesity and anti-diabetic (high fatdiet mice, reduction of body and adipose tissue weight and reduction of lipogenesis and promotion of β-oxidation) (Kang, 2012); multi-functional nutrient (Maeda, 2008); hypoglycemic (promotion of Adrb3 and GLUT4 mRNA expressions in skeletal muscle tissues, High-fat diet mice) (Maeda, 2009); anti-inflammatory (diabetic KK-Ay mice model in vivo and in vitro, down-regulation of pro-inflammatory cytokines expressions, reduction of pro-inflammatory MCP-1, PAI-1, IL-6 and TNF-α mRNA expressions) (Hosokawa, 2010); antifoulant. Ref: K. Mori, et al, Mar. Drugs, 2004, 2, 63│ H. Maeda, et al, Biochem. Biophys. Res. Commun., 2005, 332, 392│ N. M. Sachindra, et al, J. Agric. Food Chem., 2007, 55, 8516│ H. Maeda, et al, Asia Pac. J. Clin. Nutr., 2008, 17, 196│ H. Maeda, et al, Mol. Med. Rep., 2009, 2, 897│ M. Hosokawa, et al, Arch. Biochem. Biophys, 2010, 504, 17│ S. P. B. Ovenden, et al, JNP, 2011, 74, 739│ S. I. Kang, et al, J. Agric. Food Chem. 2012, 60, 3389│ CRC Press, DNP in DVD, 2012, version 20.2│ M. F. J. Raposo, et al,Mar. Drugs, 2015, 13, 5128 (rev) O O

H

OH

OH

3' O

794 Fucoxanthinol Type: Tetraterpenoids. C40H56O5 Source: Brown alga Undaria pinnatifida (edible). Pharm: anti-inflammatory (RAW264.7 macrophage-like cells and 3T3-F442A adipocytes in vitro, reduction of pro-inflammatory iNOS, COX-2, MCP-1 and IL-6 mRNA over-expression). Ref: M. Hosokawa, et al, Arch. Biochem. Biophys, 2010, 504, 17

304

6 Polyterpenoids and Meroterpenoids

O O

H

OH

OH

3' OH

795 Lutein β,ε-Carotene-3,3′-diol Type: Tetraterpenoids. C40H56O2 Coppery cryst. (MeOH), mp 196 °C, [α]643.9018 = +160° (CHCl3). Source: Green alga Chlorella pyrenoidosa (0.2%– 0.4% dw), red algae, Porphyra spp., river crab Potamon dehaani, marine invertebrate, pigment from egg yolk and leaves, found in all higher plants, microorganisms. Pharm: Antioxidant; Antineoplastic; antimutagenic; antimicrobial (wide range); treating macular degeneration (potentially useful). Ref: CRC Press, DNP in DVD, 2012, version 20.2│ M. F. J. Raposo, et al,Mar. Drugs, 2015, 13, 5128 (rev) OH

H HO

796 Myxol Type: Tetraterpenoids. C40H56O3 Source: Marine-derived bacterium Flavobacterium sp. from sponge Homaxinella sp. (Palau). Pharm: Antioxidant. Ref: A. Yokoyama, et al, Fish. Sci., 1995, 61, 684 HO

2

HO

OH

6.3 Apocarotenoids

305

6.2 Tetra-above Polyterpenoids 797 Plakopolyprenoside Type: Tetra-above polyterpenoids. C45H74O9 Amorph. solid, [α]D = −9°. Source: Sponge Plakortis simplex. Pharm: Cytotoxic. Ref: V. Costantino, et al, Tetrahedron, 2000, 56, 1393 O O HO O

O HO

O

OH

OH

6.3 Apocarotenoids 798 9’-Apo-fucoxanthinone Type: Apocarotenoids. C15H22O4 Amorph. solid, [α]D19 = −284° (c = 0.1, MeOH). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic; antifeedant (inhibits feeding by the copepod Tigriopus californicus). Ref: Y. Doi, et al, JNP, 1995, 58, 1097 H O O

OH O

799 Cavernosine Type: Apocarotenoids. C17H28O3 Oil, [α]435 = −1.8° (c = 1.19, CHCl3). Source: Sponge Fasciospongia cavernosa. Pharm: Ichthyotoxin. Ref: J. C. Braekman, et al, Bull. Soc. Chim. Belg., 1982, 91, 791

306

6 Polyterpenoids and Meroterpenoids

O O

OH

800 Diapolycopenedioic xylosyl ester A Type: Apocarotenoids. C49H70O9 Red powder, [α]633.0020 = −20° (c = 0.007, CHCl3/ MeOH). Source: Marine bacterium Rubritalea squalenifaciens. Pharm: Antioxidant (lipid peroxidation inhibitor, IC50 = 4.6 μmol/L). Ref: K. Shindo, et al, Tet. Lett., 2007, 48, 2725 O OO OH OH

2

2

OH

O O O

6.4 Megastigmane Norterpenoids 801 3-Hydroxy-5-megastigmene-7,9-dione Type: Megastigmane norterpenoids. C13H20O3 Oil, [α]D25 = −35° (c = 0.5, MeOH). Source: Dinoflagellate Prorocentrum minimum. Pharm: Extracellular antimicrobial. Ref: R. J. andersen, et al, JOC, 1980, 45, 1169│ M. G. Constantino, et al, JOC, 1986, 51, 387 HO

O

O

6.5 Bromophycolide Meroterpenoids 802 Bromophycolide A Type: Bromophycolide meroterpenoids. C27H37Br3O4 Cryst. (MeOH), [α]D23 = −35° (c = 0.21, CHCl3). Source: Red alga Callophycus serratus. Pharm: Antibacterial (MRSA, MIC = 5.9 μmol/L; VREF, MIC = 5.9 μmol/L); cytotoxic (11 cancer cell lines, mean IC50 = 6.7 μmol/L, cell line selectivity max IC50/min IC50 = 4.8); anti-HIV-1 (96USHIPS7 strain, IC50 = 9.8 μmol/L; UG/92/029 strain, IC50 = 9.1 μmol/L); antifungal (ABRCA, IC50 = 49 μmol/L); effect on cell cycle progression and apoptosis (A2780, treated for 24h with bromophycolide A, arrest in G1 phase was observed, consistent with loss of cells from S and G2/M phase). Ref: J. Kubanek, et al, Org. Lett., 2005, 7, 5261

6.5 Bromophycolide Meroterpenoids

307

Br O O HO

OH Br Br

803 Bromophycolide B Type: Bromophycolide meroterpenoids. C27H37Br3O4 Cryst. (MeOH), [α]D = −1° (c = 0.044, CHCl3). Source: Red alga Callophycus serratus. Pharm: Antibacterial (MRSA, MIC = 5.9 μmol/L; VREF, MIC = 3.0 μmol/L); cytotoxic (11 cancer cell lines, mean IC50 = 27.7 μmol/L, cell line selectivity max IC50/min IC50 = 3.8); antifungal (ABRCA, IC50 = 49 μmol/L). Ref: J. Kubanek, et al, Org. Lett., 2005, 7, 5261 O Br

O HO

OH Br Br

804 Bromophycolide J Type: Bromophycolide meroterpenoids. C28H40Br2O5 Amorph. solid, [α]D23 = +35° (c = 0.057, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antibacterial (MRSA, IC50 = 1.4 μmol/L, MMOA: undetermined); antimalarial (Plasmodium falciparum 3D7 strain, IC50 = 0.5–2.9 μmol/L, MMOA: undetermined). Ref: A. L. Lane, et al, JOC, 2009, 74, 2736 Br O O OH

HO

Br O

805 Bromophycolide M Type: Bromophycolide meroterpenoids. C27H36Br2O4 Amorph. solid, [α]D23 = +68° (c = 0.1, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm:

308

6 Polyterpenoids and Meroterpenoids

Antibacterial (MRSA, IC50 = 1.4 μmol/L, MMOA: undetermined); antimalarial (Plasmodium falciparum 3D7 strain, IC50 = 0.5–2.9 μmol/L, MMOA: undetermined). Ref: A. L. Lane, et al, JOC, 2009, 74, 2736 26

O

15

O OH

HO 6

Br Br

19

806 Bromophycolide N Type: Bromophycolide meroterpenoids. C27H36Br2O4 Amorph. solid, [α]D24 = +101° (c = 0.033, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antibacterial (MRSA, IC50 = 1.4 μmol/L, MMOA: undetermined); antimalarial (Plasmodium falciparum 3D7 strain, IC50 = 0.5–2.9 μmol/L, MMOA: undetermined). Ref: A. L. Lane, et al, JOC, 2009, 74, 2736 26

O

15

O OH

HO 6

Br Br

19

807 Bromophycolide O Type: Bromophycolide meroterpenoids. C27H37Br3O4 Amorph. solid, [α]D24 = +88° (c = 0.011, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antibacterial (MRSA, IC50 = 1.4 μmol/L, MMOA: undetermined); antimalarial (Plasmodium falciparum 3D7 strain, IC50 = 0.5–2.9 μmol/L, MMOA: undetermined). Ref: A. L. Lane, et al, JOC, 2009, 74, 2736 26

Br

O

15

O OH

HO 6 19

Br Br

6.5 Bromophycolide Meroterpenoids

309

808 Bromophycolide P Type: Bromophycolide meroterpenoids. C27H36Br2O4 Amorph. solid, [α]D24 = +120° (c = 0.05, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antibacterial (MRSA, IC50 = 1.4 μmol/L, MMOA: undetermined); antimalarial (Plasmodium falciparum 3D7 strain, IC50 = 0.5–2.9 μmol/L, MMOA: undetermined). Ref: A. L. Lane, et al, JOC, 2009, 74, 2736 O O HO

O Br

6 19

Br

809 Bromophycolide Q Type: Bromophycolide meroterpenoids. C27H36Br2O4 Amorph. solid, [α]D24 = +102° (c = 1, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antibacterial (MRSA, IC50 = 1.4 μmol/L, MMOA: undetermined); antimalarial (Plasmodium falciparum 3D7 strain, IC50 = 0.5–2.9 μmol/L, MMOA: undetermined). Ref: A. L. Lane, et al, JOC, 2009, 74, 2736 O O HO

O 6 19

Br Br

810 Bromophycolide R Type: Bromophycolide meroterpenoids. C27H35BrO4 Amorph. solid, [α]D23 = +118° (c = 0.04, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 1.7 μmol/L); antibacterial (MRSA, IC50 > 15 μmol/L; VREF, IC50 > 15 μmol/L); antituberculosis (Mycobacterium tuberculosis, MIC > 50 μmol/L); antifungal (ABRCA, IC50 > 15 μmol/L); cytotoxic (12 cancer cell lines, mean IC50 = 19 μmol/L, selectivity IC50 MAX/IC50 MIN = 2.9). Ref: A. -S. Lin, et al, JNP, 2010, 73, 275

310

6 Polyterpenoids and Meroterpenoids

O

26

15

O HO

O H Br

811 Bromophycolide S Type: Bromophycolide meroterpenoids. C27H36Br2O4 Amorph. solid, [α]D23 = +66° (c = 0.08, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 0.9 μmol/L); antibacterial (MRSA, IC50 > 15 μmol/L; VREF, IC50 = 3.8 μmol/L); antituberculosis (Mycobacterium tuberculosis, MIC = 23 μmol/L); antifungal (ABRCA, IC50 > 15 μmol/L); cytotoxic (12 cancer cell lines, mean IC50 = 16 μmol/L, selectivity IC50 MAX/IC50 MIN = 2.2). Ref: A. -S. Lin, et al, JNP, 2010, 73, 275 Br O

26

15

O HO

O H Br

812 Bromophycolide T Type: Bromophycolide meroterpenoids. C27H36Br2O4 Amorph. solid, [α]D23 = +141° (c = 0.04, MeOH). Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 8.4 μmol/L); antibacterial (MRSA, IC50 > 15 μmol/L; VREF, IC50 > 15 μmol/L); antituberculosis (Mycobacterium tuberculosis, MIC > 50 μmol/L); antifungal (ABRCA, IC50 > 15 μmol/L); cytotoxic (12 cancer cell lines, mean IC50 = 24 μmol/L, selectivity IC50 MAX/IC50 MIN = 1.6). Ref: A. -S. Lin, et al, JNP, 2010, 73, 275 O Br

O HO

Br H

O

6.6 Metachromin Meroterpenoids

311

813 Bromophycolide U Type: Bromophycolide meroterpenoids. C27H36Br2O4 Source: Red alga Callophycus serratus (Yanuca I., Fiji). Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 2.1 μmol/L); antibacterial (MRSA, IC50 = 0.9 μmol/L; VREF, IC50 = 0.9 μmol/L); antituberculosis (Mycobacterium tuberculosis, MIC = 22 μmol/L); antifungal (ABRCA, IC50 > 15 μmol/L); cytotoxic (12 cancer cell lines, mean IC50 = 16 μmol/L, selectivity IC50 MAX/ IC50 MIN = 3.1). Ref: A. -S. Lin, et al, JNP, 2010, 73, 275 O O HO

O Br Br

6.6 Metachromin Meroterpenoids 814 Metachromin A Type: Metachromin meroterpenoids. C22H30O4 Orange cryst. (hexane), mp 80–82 °C, [α]D27 = −11° (c = 1, CHCl3). Source: Sponge Hippospongia cf. metachromia. Pharm: Vasodilator (coronary, markedly inhibits 40 nmol/L KCl-induced contraction of rabbit isolated coronary artery, IC50 = 3 μmol/L); antineoplastic (L1210, IC50 = 2.40 μg/mL). Ref: M. Ishibashi, et al, JOC, 1988, 53, 2855│ W. P. Almeida, et al, Tet. Lett., 1994, 35, 1367 OH O O O

815 Metachromin C Type: Metachromin meroterpenoids. C22H30O4 Yellow solid (hexane), mp 90–91 °C, [α]D26 = −29.7° (c = 0.2, CHCl3). Source: Sponge Hippospongia cf. metachromia. Pharm: Coronary vasodilator. Ref: J. Kobayashi, et al, JNP, 1989, 52, 1173│ J. Kobayashi, et al, JOC, 1992, 57, 5773 O HO O O

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6 Polyterpenoids and Meroterpenoids

816 Metachromin D Type: Metachromin meroterpenoids. C24H34O5 Colorless oil, [α]D22 = +15° (c = 0.7, CHCl3). Source: Sponge Hippospongia metachromia (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 3.0 μg/mL; KB, IC50 = 10.0 μg/mL). Ref: J. Kobayashi, et al, JOC, 1992, 57, 5773 OH O O

O O

817 Metachromin E Type: Metachromin meroterpenoids. C22H28O4 Orange oil, [α]D22 = −54° (c = 0.3, CHCl3). Source: Sponge Hippospongia metachromia (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 0.2 μg/mL; KB, IC50 = 0.4 μg/mL). Ref: J. Kobayashi, et al, JOC, 1992, 57, 5773 O O O O

818 Metachromin F Type: Metachromin meroterpenoids. C25H36O4 Yellow oil, [α]D22 = −4° (c = 0.2, CHCl3). Source: Sponge Hippospongia metachromia (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 0.6 μg/mL; KB, IC50 = 1.9 μg/mL). Ref: J. Kobayashi, et al, JOC, 1992, 57, 5773 OH O O O

819 Metachromin G Type: Metachromin meroterpenoids. C29H37NO3 Purple oil, [α]D20 = −18° (c = 0.2, C6H6). Source: Sponge Hippospongia metachromia (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 1.3 μg/mL; KB, IC50 > 10 μg/mL). Ref: J. Kobayashi, et al, JOC, 1992, 57, 5773

6.6 Metachromin Meroterpenoids

313

OH O O HN

820 Metachromin H Type: Metachromin meroterpenoids. C26H39NO3 Purple oil, [α]D19 = −9° (c = 0.2, C6H6). Source: Sponge Hippospongia metachromia (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 2.0 μg/mL; KB, IC50 = 6.4 μg/mL). Ref: J. Kobayashi, et al, JOC, 1992, 57, 5773 OH O O HN

821 Metachromin U Type: Metachromin meroterpenoids. C22H30O3 Brown oil, [α]D21 = +28° (c = 0.2, MeOH). Source: Sponge Thorecta reticulata (Hunter I., Tasmania). Pharm: Cytotoxic (SF268, GI50 = 32 μmol/L, control Staurosporine, GI50 = 0.044 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; MCF7, GI50 = 29 μmol/L, Staurosporine, GI50 = 11 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; H460, GI50 = 37 μmol/L, Staurosporine, GI50 = 3.6 μmol/L, Paclitaxel, GI50 = 0.024 μmol/L; HT29, GI50 = 30 μmol/L, Staurosporine, GI50 = 3.6 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; CHO-K1, GI50 = 27 μmol/L, Staurosporine, GI50 = 0.13 μmol/L, Paclitaxel, GI50 = 5.9 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 1335 OH O O

822 Metachromin V Type: Metachromin meroterpenoids. C21H30O2 Colorless oil, [α]D21 = 0° (c = 0.1, CHCl3). Source: Sponge Thorecta reticulata (Hunter I., Tasmania). Pharm: Cytotoxic (SF268, GI50 = 5.1 μmol/L, control Staurosporine, GI50 = 0.044 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; MCF7, GI50 = 3.2 μmol/L, Staurosporine, GI50 = 11 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; H460, GI50 = 5.1 μmol/L, Staurosporine, GI50 = 3.6 μmol/L, Paclitaxel, GI50 = 0.024 μmol/L; HT29, GI50 = 10 μmol/L, Staurosporine, GI50 = 3.6 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; CHO-K1, GI50 = 2.1 μmol/L,

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6 Polyterpenoids and Meroterpenoids

Staurosporine, GI50 = 0.13 μmol/L, Paclitaxel, GI50 = 5.9 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 1335 OH HO

823 Metachromin W Type: Metachromin meroterpenoids. C22H26O3 Yellow oil; [α]D21 = −60° (c = 0.03, CHCl3). Source: Sponge Thorecta reticulata (Hunter I., Tasmania). Pharm: Cytotoxic (SF268, GI50 = 104 μmol/L, control Staurosporine, GI50 = 0.044 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; MCF7, GI50 = 107 μmol/L, Staurosporine, GI50 = 11 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; H460, GI50 = 50 μmol/L, Staurosporine, GI50 = 3.6 μmol/L, Paclitaxel, GI50 = 0.024 μmol/L; HT29, GI50 = 130 μmol/L, Staurosporine, GI50 = 3.6 μmol/L, Paclitaxel, GI50 = 0.012 μmol/L; CHO-K1, GI50 = 89 μmol/L, Staurosporine, GI50 = 0.13 μmol/L, Paclitaxel, GI50 = 5.9 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 1335 O

6.7 Other Meroterpenoids 824 6’-Acetoxyavarol Type: Other meroterpenoids. C23H32O4 Oil, [α]D25 = +18.9° (c = 0.44, CHCl3). Source: Sponge Dysidea cinerea (Red Sea). Pharm: Cytotoxic (P388, IC50 < 0.62 μg/mL); DNA polymerase inhibitor. Ref: S. Hirsch,et al, JNP 1991, 54, 92│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) HO

OH O 4

12

O

6.7 Other Meroterpenoids

315

825 20-O-Acetylpuupehenone Type: Other meroterpenoids. C23H30O4 Source: An unidentified sponge (order Verongida), an unidentified sponge (order Dictyoceratida). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 6%, weak). Ref: A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 O O O

O

H

826 Adociasulfate 1 Type: Other meroterpenoids. C36H54O9S2 Amorph. solid, [α]D = −15° (c = 0.1, MeOH), [α]D26 = −34° (c = 0.1, MeOH). Source: Sponge Haliclona sp. [Syn. Adocia sp.]. Pharm: Kinesin motor protein inhibitor (IC50 = 12.5 mmol//L); vacular H+-ATPase inhibitor. Ref: C. L. Blackburn, et al, JOC, 1999, 64, 5565│ J. A. Kalaitzis, et al, JOC, 1999, 64, 5571 O

H O

S

O

O

H HO

H

H

O O

O S

O

H

827 Adociasulfate 2 Type: Other meroterpenoids. C36H54O9S2 Amorph. solid, [α]D = −10.9° (c = 0.15, MeOH). Source: Sponge Haliclona sp. [Syn. Adocia sp.] (Palau). Pharm: MT-stimulated kinesin motor protein inhibitor (IC50 = 6 mmol/L). Ref: R. Sakowicz, et al, Science, 1998, 280, 292│ C. L. Blackburn, et al, JOC, 1999, 64, 5565

316

6 Polyterpenoids and Meroterpenoids

H

O O

S

O

O

H O H

O

H H

O S

O

O

H

828 Adociasulfate 3 Type: Other meroterpenoids. C36H56O10S2 Glass, [α]D = −6.25° (c = 0.08, MeOH). Source: Sponge Haliclona [Syn. Adocia] sp. Pharm: ATPase of kinesins inhibitor (IC50 = 10 μmol/L). Ref: C. L. Blackburn, et al, JOC, 1999, 64, 5565│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O HO

S O

O

O O

S

OH O

OH

HO

829 Adociasulfate 4 Type: Other meroterpenoids. C36H54O6S Amorph. solid, [α]D = −12.1° (c = 1.2, MeOH). Source: Sponge Haliclona sp. [Syn. Adocia sp.]. Pharm: ATPase of kinesins inhibitor (IC50 = 15 μmol/L). Ref: C. L. Blackburn, et al, JOC, 1999, 64, 5565│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)

6.7 Other Meroterpenoids

HO

O O

S

317

OH O

OH

830 Adociasulfate 5 Type: Other meroterpenoids. C36H54O6S Amorph. solid, [α]D = −38.7° (c = 0.33, MeOH); solid, [α]D = −10.9° (c = 0.15, MeOH). Source: Sponges Haliclona sp. [Syn. Adocia sp.] (Palau) and Adocia aculeata. Pharm: Kinesin motor protein inhibitor (IC50 = 8 mmol/L). Ref: C. L. Blackburn, et al, JOC, 1999, 64, 5565│ J. A. Kalaitzis, et al, JNP, 1999, 62, 1682 O H

O

S

O

O

OH H HO

H

H

831 Adociasulfate 6 Type: Other meroterpenoids. C36H54O6S Amorph. solid, [α]D = −12.3° (c = 0.76, MeOH). Source: Sponge Haliclona sp. [Syn. Adocia sp.] (Palau). Pharm: Kinesin motor protein inhibitor (IC50 = 6 mmol/L). Ref: C. L. Blackburn, et al, JOC, 1999, 64, 5565

318

6 Polyterpenoids and Meroterpenoids

O H

O

S

O

O

OH H O

H

H H

832 Adociasulfate 7 Type: Other meroterpenoids. C36H54O6S Amorph. powder, [α]D26 = +5° (c = 0.17, MeOH). Source: Sponge Haliclona sp. [Syn. Adocia sp.] (Great Barrier Reef). Pharm: Vacular H+-ATPase inhibitor. Ref: J. A. Kalailzis, et al, JOC, 1999, 64, 5571│ C. L. Blackburn, et al, JOC, 1999, 64, 5565│ HO

H HO

H

O O

H

O S

O

H

833 Adociasulfate 8 Type: Other meroterpenoids. C36H56O9S2 Amorph. powder, [α]D26 = +18° (c = 0.19, MeOH). Source: Sponge Haliclona sp. [Syn. Adocia sp.] (Great Barrier Reef). Pharm: Vacular H+-ATPase inhibitor. Ref: J. A. Kalailzis, et al, JOC, 1999, 64, 5571 H H

H

H

O O

OH

O

S

H

O

O

H

S

O

O O

834 Akadisulfate A Type: Other meroterpenoids. C22H32O10S2 Source: Sponge Aka coralliphaga (Quintana Roo, Mexico). Pharm: Antioxidant. Ref: L. K. Shubina, et al, Nat. Prod. Commun., 2012, 7, 487

6.7 Other Meroterpenoids

O HO

S

O

O

319

HO O S O

OH O

OH H

835 Akadisulfate B Type: Other meroterpenoids. C22H30O10S2 Source: Sponge Aka coralliphaga (Quintana Roo, Mexico). Pharm: Antioxidant. Ref: L. K. Shubina, et al, Nat. Prod. Commun., 2012, 7, 487 H O HO

S

O

O

O OH O

H

O S

OH O

836 Akaterpin Type: Other meroterpenoids. C36H54O8S2 Solid, mp > 240 °C, [α]D24 = +15° (c = 0.59, MeOH). Source: Sponge Callyspongia sp. Pharm: Phosphoinositol-specific phospholipase C inhibitor. Ref: A. Fukami, et al, Tet. Lett., 1997, 38, 1201│ N. Kawai, et al, Tet. Lett., 1999, 40, 4193│ H. Hosoi, et al, Tet. Lett., 2011, 52, 4961 O HO

S O H

O

O O

S

OH O

H

837 APS451275-1 A new drimane sesquiterpene hydroquinone Type: Other meroterpenoids. C22H30O3 White powder, [α]D25 = −25° (c = 0.1, CHCl3). Source: Deep-sea fungus Phialocephala sp. (sediment, depth of 5059 m). Pharm: Cytotoxic (P388, IC50 = 0.16 μmol/L; K562,

320

6 Polyterpenoids and Meroterpenoids

IC50 = 0.05 μmol/L). Ref: L. Chen, et al, Acta Pharm. Sin. (Zhongguo Yaoli Xuebao), 2010, 45, 1275 (in Chinese) O HO

H OH

H

838 Arenarol Type: Other meroterpenoids. C21H30O2 Cryst. (MeOH aq), mp 128–130 °C, [α]D = +19° (c = 0.1, CHCl3). Source: Sponge Dysidea arenaria (depth of 9 m, Truk Island lagoon). Pharm: Cytotoxic (ED50 = 17.5 μg/mL); antioxidant (DPPH scavenger, IC50 = 19 μmol/ L). Ref: F. J. Schmitz, et al, JOC, 1984, 49, 241│ F. J. Schmitz, et al, JOC, 1984, 49, 4971│ K. Iguchi, et al, CPB, 1990, 38, 1121│ N. K. Utkina,et al, JNP 2010, 73, 788│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) HO OH

H

839 Arenarone Type: Other meroterpenoids. C21H28O2 Yellow oil, [α]D = +8.3° (c = 0.18, CDCl3). Source: Sponge Dysidea arenaria (depth of 9 m, Truk Island lagoon). Pharm: Cytotoxic (P388, ED50 = 1.7 μg/mL). Ref: F. J. Schmitz, et al,. JOC, 1984, 49, 241│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O

H

O

6.7 Other Meroterpenoids

321

840 Arisugacin A Type: Other meroterpenoids. C28H32O8 Source: Marine-derived fungus Aspergillus terreus SCSGAF0162. Pharm: Antiviral (HSV virus, IC50 = 12.76 μmol/L). Ref: X. -H. Nong, et al, Mar. Drugs, 2014, 12, 6113 HO

O

O

O

OH

O

O

O

841 Ascofuranol Type: Other meroterpenoids. C23H31ClO5 Needles (Me2CO/hexane), mp 75 °C, [α]D21 = −7° (c = 1, MeOH), [α]D25 = −7.0° (c = 1, MeOH). Source: Marine-derived fungus Acremonium sp. from sponge Stelletta sp. (Korea). Pharm: Mycotoxin; antibiotic. Ref: P. Zhang, et al, JNP, 2009, 72, 270 O

OH O H OH

OH

Cl

842 Ascofuranone Type: Other meroterpenoids. C23H29ClO5 Needles (Me2CO/hexane), mp 84 °C, [α]D25 = −50° (c = 1, MeOH). Source: Marine-derived fungus Acremonium sp. from sponge Stelletta sp. (Korea). Pharm: Anti-inflammatory (100 μmol/L, NO and TNF-R production inhibitor); mycotoxin; antineoplastic; mitochondrial oxygen uptake inhibitor; glycerol-3-phosphate dehydrogenase inhibitor; LD50 (rat, ipr) = 1350 mg/kg. Ref: P. Zhang, et al, JNP, 2009, 72, 270 O

OH O H OH

O

Cl

843 Ascosalipyrrolidinone A Type: Other meroterpenoids. C27H41NO3 Amorph. powder, [α]D20 = −51.3° (c = 0.16, EtOH). Source: Marine-derived fungus Ascochyta salicorniae from green alga Ulva sp. (German coast of the North Sea). Pharm: Tyrosine kinase inhibitor (TKp56lck, 40 μg/mL, InRt = 30%, 200 μg/mL, InRt = 77%); antiplasmodial (Plasmodium

322

6 Polyterpenoids and Meroterpenoids

falciparum K1, IC50 = 736 ng/mL; Plasmodium falciparum NF 54, IC50 = 378 ng/mL); antibacterial. (50 μg/disk, Bacillus megaterium, IZD = 5 mm); antifungal (50 μg/ disk, Microbotryum violacea, IZD = 2 mm; Mycotypha microspora, IZD = 4 mm). Ref: C. Osterhage, et al, JOC, 2000, 65, 6412 H N

O

O

O H

H

844 Asperdemin Type: Other meroterpenoids. C21H28O7 Source: Marine-derived fungus Aspergillus versicolor (sediment, Sakhalin Bay, Sea of Okhotsk, Russia). Pharm: Cytostatic (6.38 mmol/L, increase in number of eggs in four-cell stage blastomere by 2.4%); membranolytic (causing increase in number of lysed cells compared to reference sample by 9.3%, weak). Ref: A. N. Yurchenko, et al, Russ. Chem. Bull., 2010, 59, 852 O OH

O

H

O

O O

H

OH

845 Aureol Type: Other meroterpenoids. C21H30O2 Cryst. (hexane), mp 144–144.5 °C, [α]D = +65° (c = 2, CHCl3). Source: Sponges Hyrtios sp., Smenospongia aurea and Aplysina lacunosa. Pharm: PLA2 inhibitor (bee venom PLA2, IC50 = (0.46 ± 0.02)mmol/L); antioxidant (Oxygen Radical Absorbance Capacity (ORAC) = (0.29 ± 0.03), significant). Ref: P. Djura, et al, JOC, 1980, 45, 1435│ A. A. Tymiak, et al, Tetrahedron, 1985, 41, 1039│ A. Longeon, et al, Mar. Drugs, 2011, 9, 879 OH 6'

O

H

6.7 Other Meroterpenoids

323

846 Austalide B Type: Other meroterpenoids. C26H36O7 Source: Marine-derived Fungus Aspergillus aureolatus HDN14-107 from unidentified sponge (Xisha Is., China). Pharm: Antiviral (influenza virus A (H1N1), IC50 = 99 μmol/L). Ref: J. X. Peng, et al, Mar. Drugs， 2016, 14, 131 23

24 13

HO

26

12

O

O 6

22

H

17

1

9

11

15 16

7

O

27

H

25

10

O

O

19

28

O

847 Austalide I Type: Other meroterpenoids. C27H34O8 Source: Marine-derived Fungus Aspergillus aureolatus HDN14-107 from unidentified sponge (Xisha Is., China). Pharm: Antiviral (influenza virus A (H1N1), IC50 = 131 μmol/L). Ref: J. X. Peng, et al, Mar. Drugs， 2016, 14, 131 O 13

O

O

7

1

9

11

O

15

26 16

10

12 27

25

23

24

O

H

H

17

22

6

O

O

19

28

O

848 Austalide M Type: Other meroterpenoids. C27H36O9 Source: Marine-derived fungus Aspergillus sp. from sponge Tethya aurantium (Mediterranean Sea, Italy). Pharm: Antibacterial (Halomonas aquamarina, Polaribacter irgensii, Pseudoalteromonas elyakovii, Roseobacter litoralis, Shewanella putrefaciens, Vibrio harveyi, Vibrio natriegens, Vibrio proteolyticus and Vibrio carchariae, MIC = 0.001–0.01 μg/mL). Ref: Y. Zhou, et al, EurJOC, 2011, 30, 6009│ Y. M. Zhou, et al, Tetrahedron Lett. 2014, 55, 2789 HO

O O

O

O

H

O

O

O

O

849 Austalide N Type: Other meroterpenoids. C28H36O10 Source: Marine-derived fungus Aspergillus sp. from sponge Tethya aurantium (Mediterranean Sea, Italy). Pharm: Antibacterial

324

6 Polyterpenoids and Meroterpenoids

(Halomonas aquamarina, Polaribacter irgensii, Pseudoalteromonas elyakovii, Roseobacter litoralis, Shewanella putrefaciens, Vibrio harveyi, Vibrio natriegens, Vibrio proteolyticus and Vibrio carchariae, MIC = 0.01 μg/mL). Ref: Y. Zhou, et al, EurJOC, 2011, 30, 6009│ Y. M. Zhou, et al, Tetrahedron Lett. 2014, 55, 2789 HO

O O O

O

H

O

O

O

O

850 Austalide P acid Type: Other meroterpenoids. C25H34O7 Source: Marine-derived Fungus Aspergillus aureolatus HDN14-107 from unidentified sponge (Xisha Is., China). Pharm: Antiviral (influenza virus A (H1N1), IC50 = 145 μmol/L). Ref: J. X. Peng, et al, Mar. Drugs， 2016, 14, 131 O O H

HO

O

O

O

OH

851 Austalide R Type: Other meroterpenoids. C25H32O9 Source: Marine-derived fungus Aspergillus sp. from a sponge. Pharm: Antibacterial (Halomonas aquamarina, Polaribacter irgensii, Pseudoalteromonas elyakovii, Roseobacter litoralis, Shewanella putrefaciens, Vibrio harveyi, Vibrio natriegens, Vibrio proteolyticus and Vibrio carchariae, MIC = 0.01–0.1 μg/mL). Ref: Y. M. Zhou, et al, EurJOC, 2011, 30, 6009│ Y. M. Zhou, et al, Tet. Lett., 2014, 55, 2789 HO

O O

H O

O

H

H OH O

O

HO

852 Austalide U Type: Other meroterpenoids. C25H32O8 White amorphous powder (MeOH), [α]D20 = −46° (c = 0.13, CH2Cl2). Source: Marine-derived Fungus Aspergillus aureolatus

6.7 Other Meroterpenoids

325

HDN14-107 from unidentified sponge (Xisha Is., China). Pharm: Antiviral (influenza virus A (H1N1), IC50 = 90 μmol/L). Ref: J. X. Peng, et al, Mar. Drugs， 2016, 14, 131 24 13

HO

12

O

27 25

23 10 7

1

9

11

O

15

26 16

O

H

OH

17

22

6

O

O

19

28

O

853 Avarol Type: Other meroterpenoids. C21H30O2 Cryst. (CHCl3), mp 148–150 °C, [α]D = +6.1°; mp 138–140 °C, [α]D = +4.7° (c = 0.17, CHCl3). Source: Sponge Dysidea avara. Pharm: Antileukemia agents (in vitro and in vivo); anti-HIV-1 (in vitro, IC50 = 2.9 μmol/L, but not efficient in clinical treatment of patients with AIDS); Tlymphotropic cytostatic activity; inhibits growth of fibroblasts, lymphocytic leukemia and lymphoblastic B and T cells (IC50 = 13.9–15.6 μmol/L); cytotoxic (brine shrimp Artemia salina, LD50 = 0.18 ppm; potato disk assay, 64% inhibition); immunostimulant; anti-inflammatory; analgesic; ichthyotoxic; antimutagenic (with inhibiting effect on benzo[a]pyrene monooxygenase); anti-HIV; LD50 (mus, ipr) 269 mg/kg. Ref: L. Minale, et al, Tet. Lett., 1974, 15, 3401│ S. De Rosa, et al, J. Chem. Soc., Perkin Trans. 1, 1976, 1408│ W. E. Muller, et al, Cancer Res., 1985, 45, 4822│ P. S. J. Sarin, Natl. Cancer Inst., 1987, 78, 663│ K. Iguchi, et al, CPB, 1990, 38, 1121│ R. Puliti, et al, Acta Cryst., Sect. C, 1994, 50, 830│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)│ CRC Press, DNP on DVD, 2012, version 20.2 HO

OH

4

12

854 Avarone Type: Other meroterpenoids. C21H28O2 Oil, [α]D = +19.1° (c = 0.37, CHCl3). Source: Sponge Dysidea avara. Pharm: Antileukemia (in vitro and in vivo); anti-HIV-1 (in vitro, IC50 = 1.5 μmol/L, but not efficient in clinical treatment of patients with AIDS); inhibits growth of fibroblasts, lymphocytic leukemia and lymphoblastic B and T cells (IC50 = 13.9–15.6 μmol/L); immunostimulant; anti-inflammatory; antimutagenic. Ref: L. Minale, et al, Tet. Lett., 1974, 15, 3401│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)

326

6 Polyterpenoids and Meroterpenoids

O

O

4

12

855 Avarone adduct A Type: Other meroterpenoids. C26H34O3 Oil. Source: Sponge Dysidea sp. (New Zealand). Pharm: Cytotoxic (P388, IC50 = 2.8 μg/mL); antibacterial (Bacillus subtilis); antifungal (Trichophyton mentagrophytes). Ref: M. Stewart, et al, Aust. J. Chem., 1997, 50, 341 O HO

H

O

H

H

856 Avarone adduct B Type: Other meroterpenoids. C26H34O3 Oil. Source: Sponge Dysidea sp. (New Zealand). Pharm: Cytotoxic (P388, IC50 = 1.3 μg/mL); antibacterial (Bacillus subtilis, IC50 = 3 μg/mL); antifungal (Trichophyton mentagrophytes). Ref: M. Stewart, et al, Aust. J. Chem., 1997, 50, 341 O HO

H 3'

O

H

H

4'

857 Avarone adduct C Type: Other meroterpenoids. C26H36O3 Orange oil. Source: Sponge Dysidea sp. (New Zealand). Pharm: Cytotoxic (P388, IC50 = 8.9 μg/mL); antibacterial (Bacillus subtilis, IC50 = 5 μg/mL); antifungal (Trichophyton mentagrophytes). Ref: M. Stewart, et al, Aust. J. Chem., 1997, 50, 341

6.7 Other Meroterpenoids

O HO

H

O

327

H

H

858 Beauversetin Type: Other meroterpenoids. C24H33NO4 Amorph. yellow powder, [α]D22 = +122° (c = 0.24, CHCl3). Source: Marine-derived fungus Beauveria bassiana from sponge Myxilla incrustans (Germany). Pharm: Cytotoxic (panel of 6 cell lines, moderate). Ref: K. Neumann, et al, Nat. Prod. Commun., 2009, 4, 347 H

O

H OH

HO

O

N H

859 Bicycloalternarene A Type: Other meroterpenoids. C20H32O6 Source: Marine-derived fungus Alternaria sp. from sponge Callyspongia sp. (Sanya, Hainan I., China). Pharm: NF-κB inhibitor (RAW264.7 cells, weak to moderate). Ref: G. Zhang, et al, JNP, 2013, 76, 1946 OH

OH

O HO

OH O

860 Bicycloalternarene B Type: Other meroterpenoids. C21H34O6 Source: Marine-derived fungus Alternaria sp. from sponge Callyspongia sp. (Sanya, Hainan I., China). Pharm: NF-κB inhibitor (RAW264.7 cells, weak to moderate). Ref: G. Zhang, et al, JNP, 2013, 76, 1946

O

OH

OH OH

HO O

328

6 Polyterpenoids and Meroterpenoids

861 Bicycloalternarene C Type: Other meroterpenoids. C21H30O6 Source: Marine-derived fungus Alternaria sp. from sponge Callyspongia sp. (Sanya, Hainan I., China). Pharm: NF-κB inhibitor (RAW264.7 cells, weak to moderate). Ref: G. Zhang, et al, JNP, 2013, 76, 1946 OH

OH O

OH O

O

862 Bicycloalternarene D Type: Other meroterpenoids. C21H30O6 Source: Marine-derived fungus Alternaria sp. from sponge Callyspongia sp. (Sanya, Hainan I., China). Pharm: NF-κB inhibitor (RAW264.7 cells, weak to moderate). Ref: G. Zhang, et al, JNP, 2013, 76, 1946

O

OH OH O

HO O

863 Bifurcarenone Type: Other meroterpenoids. C27H38O5 Oil, [α]D20 = +5.5° (c = 8, EtOH), [α]D20 = +5.7° (c = 0.24, CHCl3), Source: Brown algae Cystoseira stricta and Bifurcaria galapagensis. Pharm: Antibacterial. Ref: K. Mori, et al, Tetrahedron, 1989, 45, 1945│ H. H. Sun, et al, Tet. Lett., 1980, 3123 O OH O

OH

OH

864 Bispuupehenone Type: Other meroterpenoids. C42H54O6 Cryst. (CH2Cl2), mp 234–240 °C, [α]D24 = −98° (c. = 2.4, CHCl3). Source: Sponges Hyrtios sp. (New Caledonia) and Hyrtios eubamma (Tahiti, Pacific Ocean; Maui I., USA). Pharm: Cytotoxic (KB, MIC > 10 μg/mL; LoVo, MIC = 10 μg/mL; P388, IC50 > 20 μg/mL; A549, IC50 > 20 μg/mL; HT29, IC50 > 20 μg/mL; CV-1, IC50 > 20 μg/mL); antiviral (Mv 1 Lu/HSV I1, reduction > 10%; CV-1/MSV-1, reduction > 40%; BHK/VSV, reduction > 40%); immunomodulatory. Ref: P. Amade,

6.7 Other Meroterpenoids

329

et al, Helv. Chim. Acta, 1983, 66, 1672│ S. S. Nasu, et al, JOC, 1995, 60, 7290│ S. Urban, et al, JNP, 1996, 59, 900│ S. Qin, et al, Acta Cryst. E, 2008, 64, o946│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) H H O

H HO O

O OH

H O H

H

865 Bis(sulfato)cyclosiphonodictyol A Cyclosiphonodictyol bissulfate A Type: Other meroterpenoids. C22H32N9O2 Amorph. solid, [α]D24 = +12° (c = 0.2, MeOH). Source: Sponge Siphonodictyon coralliphagum. Pharm: Inhibits binding of [3H]-LTB4 to hmn neutrophils (IC50 = 44.5 μmol/L). Ref: K. B. Killday, et al, JNP, 1995, 58, 958│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)

O HO

O

O

O

O

S

S

O OH

O

866 Bolinaquinone Type: Other meroterpenoids. C22H30O4 Yellow glass, [α]D = −106° (c = 0.4, CHCl3). Source: Sponge Dysidea sp. Pharm: Cytotoxic (HCT116, IC50 = 1.9 μg/mL, cytotoxicity studies carried out suggest bolinaquinone acts by interfering with or damaging DNA). Ref: F. S. De Guzman, et al, JOC, 1998, 63, 8042│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH

H

O O O

330

6 Polyterpenoids and Meroterpenoids

867 Chevalone E Type: Other meroterpenoids. C26H38O4 Source: Marine-derived fungus Aspergillus similanensis sp. nov KUFA 0013. Pharm: Antibacterial (synergism with antibiotic oxacillin, MRSA). Ref: C. Prompanya, et al, Mar. Drugs, 2014, 12, 5160 O

H HO

H

O

O

H

868 6’-Chloroaureol Type: Other meroterpenoids. C21H29ClO2 Yellow cryst. (MeOH), mp 143–144 °C, [α]D = +27.8° (c = 0.02, CHCl3). Source: Sponge Smenospongia aurea (Caribbean). Pharm: Antimicrobial. Ref: A. Aiello, et al, Z. Naturforsch, B, Chem. Sci., 1993, 48, 209 OH 6'

Cl

O

H

869 21-Chloropuupehenol Type: Other meroterpenoids. C27H27ClO3 Red glass, [α]D = +112° (c = 0.35, MeOH). Source: Sponge Hyrtios sp. (Hawaii). Pharm: Antimalarial. Ref: S. S. Nasu, et al, JOC, 1995, 60, 7290 OH Cl

21

OH

15

9

O

H

870 Chromazonarol Type: Other meroterpenoids. C21H30O2 Gum, [α]D25 = −50° (c = 1, CHCl3). Source: Brown alga Dictyopteris undulata. Pharm: Antifeedant; ichthyotoxin. Ref: W. Fenical, et al, Experientia, 1975, 31, 1004│ G. Cimino, et al, Experientia, 1975, 31, 1250│ F. Song,et al, Zhongguo Zhong Yao Za Zhi 2006, 31, 125│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)

6.7 Other Meroterpenoids

331

OH

O

H

871 ent-Chromazonarol Type: Other meroterpenoids. C21H30O2 Source: Sponge Dysidea pallescens. Pharm: Cytotoxic (P388, A549. HT29 and MEL28, all IC50S = 15.9 μmol/L). Ref: G. Cimino,et al, Experientia 1975, 31, 1117│ G. Cimino, et al, Experientia, 1975, 31, 1250│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH

O

H

872 epi-Conicol Type: Other meroterpenoids. C16H20O2 Glass, [α]D = +58° (c = 0.09, CHCl3). Source: Ascidian Synoicum castellatum. Pharm: Cytotoxic. Ref: A. R. Carroll, et al, Aust. J. Chem., 1993, 46, 1079

HO

H H O

873 Conthiaquinone A Type: Other meroterpenoids. C19H25NO6S Source: Ascidian Aplidium conicum (Porto Cesareo, Lecce, Italy). Pharm: Cytotoxic (modest). Ref: M. Menna, et al, EurJOC, 2013, 3241

332

O

S

6 Polyterpenoids and Meroterpenoids

O

N H

O

OH

H

O

H

O

874 Conthiaquinone A methyl ether Type: Other meroterpenoids. C20H27NO6S Source: Ascidian Aplidium conicum (Porto Cesareo, Lecce, Italy). Pharm: Cytotoxic (modest). Ref: M. Menna, et al, EurJOC, 2013, 3241 O

S

O

N H

O

O

H

O

H

O

875 Corallidictyal A Type: Other meroterpenoids. C22H28O4 Source: Sponge Aka coralliphaga [Syn. Siphonodictyon coralliphaga] (Little San Salvador I., Bahamas). Pharm: PKC inhibitor (IC50 = 28 μmol/L; another cAMP-dependent kinase, 300 μmol/L, inactive); PKA inhibitor (IC50 = 300 μmol/L). Ref: J. A. Chan, et al, JNP, 1994, 57, 1543│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O

HO

O H O 9

876 Corallidictyal B Type: Other meroterpenoids. C22H28O4 Source: Sponge Aka coralliphaga [Syn. Siphonodictyon coralliphaga] (Little San Salvador I., Bahamas). Pharm: PKC inhibitor (IC50 = 28 μmol/L, good selectivity); PKA inhibitor (IC50 = 300 μmol/L). Ref: J. A. Chan, et al, JNP, 1994, 57, 1543│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev)

6.7 Other Meroterpenoids

333

O

HO

O H O 9

877 Corallidictyal C Type: Other meroterpenoids. C22H30O4 Yellow powder. Source: Sponge Aka coralliphagum. Pharm: Antiproliferative (cultures of mouse fibroblasts and activity was linked to the presence of the ortho-hydroquinone moiety). Ref: A. Grube, et al, JNP, 2007, 70, 504│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH

HO

O H O 9

878 Corallidictyal D Type: Other meroterpenoids. C22H30O4 Yellow powder. Source: Sponge Aka coralliphagum. Pharm: Antiproliferative (cultures of mouse fibroblasts and activity was linked to the presence of the ortho-hydroquinone moiety). Ref: A. Grube, et al, JNP, 2007, 70, 504│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH

HO

O H O 9

879 Coscinoquinol Type: Other meroterpenoids. C31H46O2 Oil, [α]D = +8.2° (c = 0.27, CHCl3). Source: Sponges Coscinoderma sp. (Great Barrier Reef) and Dysidea sp. (tropical). Pharm: Antibacterial (Bacillus subtilis, MIC ≈ 1.56–12.5 μg/mL, MMOA: isocitrate lyase

334

6 Polyterpenoids and Meroterpenoids

inhibition). Ref: G. V. Alea, et al, Aust. J. Chem., 1994, 47, 191│ D. Lee, et al, BoMCL 2008, 18, 5377 HO OH

H

880 Coscinosulfate Type: Other meroterpenoids. C31H48O6S Amorph. solid, mp 129–130 °C, [α]D22 = +5° (c = 1.4, MeOH). Source: Sponge Coscinoderma matthewsi (New Caledonia). Pharm: Cdc25 phosphatase inhibitor; antimitotic agent. Ref: A. Loukaci, et al, BoMC, 2001, 9, 3049│ S. Poigny, et al, JOC, 2001, 66, 7263 O O

S

OH

OH

O

OH

8 22

H

881 Crassumtocopherol A Type: Other meroterpenoids. C29H50O5 Source: Soft coral Lobophytum crassum (Dongsha Atoll, Taiwan). Pharm: Cytotoxic (moderate). Ref: S. -Y. Cheng, et al, Bull. Chem. Soc. Jpn., 2011, 84, 783

HO OH

OH O OH

882 Crassumtocopherol B Type: Other meroterpenoids. C31H52O6 Source: Soft coral Lobophytum crassum (Dongsha Atoll, Taiwan). Pharm: Cytotoxic (moderate). Ref: S. -Y. Cheng, et al, Bull. Chem. Soc. Jpn., 2011, 84, 783

6.7 Other Meroterpenoids

335

O O OH

OH O OH

883 15α-Cyano-19,20-di-O-acetylpuupehenol Type: Other meroterpenoids. C26H33NO5 Source: Some unidentified sponges (orders Verongida and Dictyoceratida). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 64%). Ref: J. K. Zjawiony,et al, JNP, 1998, 61, 1502│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 O O O

O

N O H H

884 10,17-O-Cyano-4,5-di-epi-dactylospongiaquinone Type: Other meroterpenoids. C22H28O4 Source: Sponge Dactylospongia elegans (collected in both Malaysia and Palau). Pharm: Antiproliferative (high concentration, 1,4- benzoquinone moiety demonstrated as essential for activity). Ref: L. Du, et al, JNP, 2013, 76, 1175 O O

O O

885 15-Cyanopuupehenol Type: Other meroterpenoids. C22H29NO3 Light tan glass, [α]D = −22° (c = 0.37, MeOH). Source: Sponge Verongida sp. Pharm: Cytotoxic (KB, 5 μg/mL); antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 96%); antiviral (HSV-2, 5 μg/mL, 98% reduction); antifungal (6 mm disk, 5 μg/mL, Penicillium notatum 10 mm partial inhibition, Trichophyton mentagrophytes 9 mm, and Saccharomyces cerevisiae 7 mm); immunomodulator. Ref: T. Hamann, et al, Tet. Lett., 1991, 32, 5671│ S. S. Nasu, et al, JOC, 1995, 60, 7290│ S. Urban, et al, JNP, 1996, 59, 900│

336

6 Polyterpenoids and Meroterpenoids

J. K. Zjawiony,et al, JNP, 1998, 61, 1502│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949M.│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH OH N

O H

H

886 15-Cyanopuupehenone Type: Other meroterpenoids. C22H27NO3 Yellow glass, [α]D = +168° (c = 0.082, MeOH). Source: Sponges Hyrtios sp. (Hawaii) and Verongida sp. (Hawaii). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 90%); immunomodulator. Ref: M. T. Hamann,et al, JOC, 1993, 58, 6565│ S. S. Nasu,et al, JOC, 1995, 60, 7290│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949│M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH O N O

H

887 Cyclocymopol Type: Other meroterpenoids. C16H20Br2O2 Oil. Source: Green alga Cymopolia barbata (Bermuda and Puerto Rico). Pharm: Phospholipase A2 inhibitor. Ref: H. E. Högberg, et al, J. Chem. Soc., Perkin Trans. 1, 1976, 1696│ O. J. McConnell, et al, Phytochemistry, 1982, 21, 2139 OH Br

1'

Br

OH

888 Cyclospongiacatechol Type: Other meroterpenoids. C23H32O5 Source: Sponge Dactylospongia elegans (collected in both Malaysia and Palau). Pharm: Antiproliferative (high concentration,

6.7 Other Meroterpenoids

337

1,4- benzoquinone moiety demonstrated as essential for activity). Ref: L. Du, et al, JNP, 2013, 76, 1175 O

O

OH OH O

H

889 Cystoazorol A Type: Other meroterpenoids. C29H44O5 Yellowish oil, [α]D24 = +54.5° (c = 0.05, CH3OH). Source: Brown alga Cystoseira abies-marina (Mosteiros Sao Miguel I., Azores, Atlantic Ocean). Pharm: Cytotoxic (HeLa, Lag phase IC50 = (10.2 ± 0.2)μg/mL, Log phase IC50 = (2.8 ± 1.2)μg/mL, control Taxol, Lag phase IC50 = (0.12 ± 0.07)μg/mL, Log phase IC50 = (0.06 ± 0.01)μg/mL; Vero, Lag phase IC50 = (16.7 ± 0.1)μg/mL, Log phase IC50 = (6.9 ± 0.5)μg/mL, Taxol, Lag phase IC50 = (0.18 ± 0.04)μg/mL, Log phase IC50 = (0.03 ± 0.01) μg/mL); antioxidant (DPPH scavenger, strong). Ref: V. L. M. Gouveia, et al, Phytochem. Lett., 2013, 6, 593 O

O

OH

O

OH

890 Cystoazorol B Type: Other meroterpenoids. C29H44O6 Yellowish oil, [α]D24 = −51.3° (c = 0.04, CH3OH). Source: Brown alga Cystoseira abies-marina (Mosteiros Sao Miguel I., Azores, Atlantic Ocean). Pharm: Cytotoxic (HeLa, Lag phase IC50 > 40 μg/mL, Log phase IC50 > 40 μg/mL; Vero, Lag phase IC50 > 40 μg/mL, Log phase IC50 > 40 μg/mL); antioxidant (DPPH scavenger, strong). Ref: V. L. M. Gouveia, et al, Phytochem. Lett., 2013, 6, 593 O

O

OH OH

OH

O

338

6 Polyterpenoids and Meroterpenoids

891 Cystoazorone A Type: Other meroterpenoids. C23H32O4 Pale yellow oil. Source: Brown alga Cystoseira abies-marina (Mosteiros Sao Miguel I., Azores, Atlantic Ocean). Pharm: Cytotoxic (HeLa, Lag phase IC50 = (25.0 ± 1.3)μg/mL, Log phase IC50 = (17.3 ± 1.6)μg/mL, control Taxol, Lag phase IC50 = (0.12 ± 0.07)μg/mL, Log phase IC50 = (0.06 ± 0.01)μg/mL; Vero, Lag phase IC50 = (28.0 ± 1.7)μg/mL, Log phase IC50 = (16.5 ± 5.3)μg/mL, Taxol, Lag phase IC50 = (0.18 ± 0.04)μg/mL, Log phase IC50 = (0.03 ± 0.01)μg/mL). Ref: V. L. M. Gouveia, et al, Phytochem. Lett., 2013, 6, 593 O O

O 6E

O

892 Cystoazorone B Type: Other meroterpenoids. C23H32O4 Yellowish oil. Source: Brown alga Cystoseira abies-marina (Mosteiros Sao Miguel I., Azores, Atlantic Ocean). Pharm: Cytotoxic (HeLa, Lag phase IC50 = (32.0 ± 8.4)μg/mL, Log phase IC50 = (20.1 ± 1.7)μg/mL, control Taxol, Lag phase IC50 = (0.12 ± 0.07)μg/mL, Log phase IC50 = (0.06 ± 0.01)μg/mL; Vero, Lag phase IC50 > 40μg/mL, Log phase IC50 = (22.1 ± 1.8)μg/mL, Taxol, Lag phase IC50 = (0.18 ± 0.04)μg/mL, Log phase IC50 = (0.03 ± 0.01)μg/mL). Ref: V. L. M. Gouveia, et al, Phytochem. Lett., 2013, 6, 593 O

O

6Z

O

O

893 Cystodione A Type: Other meroterpenoids. C28H40O6 Source: Brown alga Cystoseira usneoides (Gibraltar Strait). Pharm: Antioxidant (ABTS∙+ assay, strong). Ref: C. de los Reyes, et al, JNP, 2013, 76, 621

6.7 Other Meroterpenoids

339

HO

O

HO

O

O 6Z

OH

894 Cystodione B Type: Other meroterpenoids. C28H40O6 Source: Brown alga Cystoseira usneoides (Gibraltar Strait). Pharm: Antioxidant (ABTS∙+ assay, strong). Ref: C. de los Reyes, et al, JNP, 2013, 76, 621 O

O

HO

6E

OH

HO

O

895 Cystodione C Type: Other meroterpenoids. C22H30O5 Source: Brown alga Cystoseira usneoides (Gibraltar Strait). Pharm: Antioxidant (ABTS∙+ assay, strong). Ref: C. de los Reyes, et al, JNP, 2013, 76, 621

O O

HO

O 6Z

OH

896 Cystodione D Type: Other meroterpenoids. C22H30O5 Source: Brown alga Cystoseira usneoides (Gibraltar Strait). Pharm: Antioxidant (ABTS∙+ assay, strong). Ref: C. de los Reyes, et al, JNP, 2013, 76, 621

340

6 Polyterpenoids and Meroterpenoids

O

O

HO

6E

OH

O

897 Cystodione E Type: Other meroterpenoids. C28H40O7 Source: Brown alga Cystoseira usneoides (Gibraltar Strait). Pharm: Antioxidant (ABTS∙+ assay, strong). Ref: C. de los Reyes, et al, JNP, 2013, 76, 621 HO O

O

HO

O

O 6Z

OH

898 Cystodione F Type: Other meroterpenoids. C28H40O7 Source: Brown alga Cystoseira usneoides (Gibraltar Strait). Pharm: Antioxidant (ABTS∙+ assay, strong). Ref: C. de los Reyes, et al, JNP, 2013, 76, 621 O

HO

O 6E

OH

O

O

HO

899 8-epi-Dactyloquinone Type: Other meroterpenoids. C22H28O4 Source: Sponge Dactylospongia elegans (collected in both Malaysia and Palau). Pharm: Antiproliferative (high concentration, 1,4- benzoquinone moiety demonstrated as essential for activity); HIF-1 (Hypoxia Inducible Factor-1) activator. Ref: L. Du, et al, JNP, 2013, 76, 1175

6.7 Other Meroterpenoids

341

O O

O O

900 Dactyloquinone B Type: Other meroterpenoids. C22H28O4 Pale yellow powder, mp 178–180 °C, [α]D26 = −33.1° (c = 1.5, CHCl3). Source: Sponge Dactylospongia elegans. Pharm: Cytotoxic (SF268, GI50 = 32 μmol/L; MCF7, GI50 = 41 μmol/L; H460, GI50 = 30 μmol/L; HT29, GI50 = 46 μmol/L; CHO-K1, GI50 = 43 μmol/L). Ref: H. Mitome, et al, J. Nat. Prod., 2001, 64, 1506│ S. P. B. Ovenden, et al, JNP, 2011, 74, 65 O O O

O

901 Debromophycolide A Type: Other meroterpenoids. C27H36O5 Amorph. solid, [α]D23 = −7° (c = 0.012, CHCl3). Source: Red alga Callophycus serratus. Pharm: Cytotoxic (11 cancer cell lines, mean IC50 > 76 μmol/L); antifungal (ABRCA, not significantly active). Ref: J. Kubanek, et al, Org. Lett., 2005, 7, 5261 OH O O HO

H

O H

H

902 11α-Dehydroxyisoterreulactone A Type: Other meroterpenoids. C27H32O7 Source: Marine-derived fungus Aspergillus terreus SCSGAF0162. Pharm: Antiviral (HSV virus, IC50 = 33.38 μmol/L). Ref: X. H. Nong, et al, Mar. Drugs, 2014, 12, 6113

342

6 Polyterpenoids and Meroterpenoids

HO

O O

O

H

O

O

O

903 2’,5’-Diacetylavarol Type: Other meroterpenoids. C25H34O4 Cryst. (hexane), mp 92–94 °C, [α]D = +12.5° (c = 1.0, CHCl3). Source: Sponge Dysidea avara. Pharm: Cytotoxic (brine shrimp Artemia salina, LD50 = 0.15 ppm; potato disk assay, InRt = 55%); cytotoxic (HepA and KB). Ref: A. De Guilio, et al, Tetrahedron, 1990, 46, 7971│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O

O

5'

O

O

4

12

904 Dictyoceratin B Type: Other meroterpenoids. C23H32O5 Amorph. solid, mp 154.5–155.5 °C, [α]D25 = −1.22° (c = 1.12, CHCl3). Source: Sponge Hippospongia sp. Pharm: Antibacterial (Staphyrococcus aureus, Bacillus subtilis). Ref: H. Nakamuta, et al, Tetrahedron, 1986, 42, 4197 OH HO

OH 17

19

O H

22

O

905 Dictyoceratin C Dictyoceratin Type: Other meroterpenoids. C23H32O3 Solid, [α]D23 = +16.7° (c = 0.03, CHCl3). Source: Sponges Dactylospongia sp. and Petrosaspongia metachromia.

6.7 Other Meroterpenoids

343

Pharm: Cytotoxic (differentiation-inducing activity to K562 cells into erythroblast, lowest effective concentration = 22,5 μmol/L). Ref: S. Aoki, et al, CPB, 2004, 52, 935 O

H

O

OH 5

906 4,5-Di-epi-dactylospongiaquinone Type: Other meroterpenoids. C22H30O4 Source: Sponge Dactylospongia elegans (collected in both Malaysia and Palau). Pharm: Antiproliferative (high concentration, 1,4-benzoquinone moiety demonstrated as essential for activity); HIF-1 (Hypoxia Inducible Factor-1) activator. Ref: L. Du, et al, JNP, 2013, 76, 1175 O O

O OH

H

907 3’,6’-Dihydroxyavarone Avarone B Type: Other meroterpenoids. C21H28O4 Oil, [α]D25 = +65.6° (c = 0.32, CHCl3). Source: Sponge Dysidea cinerea (Red Sea). Pharm: Cytotoxic (P388, IC50 = 1.2 μg/mL). Ref: S. Hirsch, et al, JNP, 1991, 54, 92│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH O O OH 4

12

908 5,8-Di-epi-ilimaquinone Type: Other meroterpenoids. C22H30O4 Source: Sponge Dactylospongia elegans (collected in both Malaysia and Palau). Pharm: Antiproliferative (high concentration,

344

6 Polyterpenoids and Meroterpenoids

1,4-benzoquinone moiety demonstrated as essential for activity). Ref: L. Du, et al, JNP, 2013, 76, 1175 O O

O OH

H

909 Dipuupehedione Type: Other meroterpenoids. C42H50O6 Red glassy solid. Source: Sponge Hyrtios sp. (New Caledonia). Pharm: Cytotoxic (KB, ED50 = 3 μg/mL). Ref: M. -L. BourguetKondracki, et al, Tet. Lett., 1996, 37, 3861│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) H H O

O

O

O

O

O H H

910 Distrongylophorine Type: Other meroterpenoids. C52H70O8 Cream powder. Source: Sponge Strongylophora sp. Pharm: LC50 (brine shrimp) = 10.5 μg/mL. Ref: M. Balbin-Oliveros, et al, JNP, 1998, 61, 948 O COOH O

COOH

O OH

6.7 Other Meroterpenoids

345

911 Dysideavarone A Type: Other meroterpenoids. C23H28O3 Source: Sponge Dysidea avara (Xisha Is., South China Sea). Pharm: Cytotoxic. Ref: W. -H. Jiao, et al, Org. Lett., 2012, 14, 202 H

O O

O

912 Dysideavarone B Type: Other meroterpenoids. C23H28O3 Source: Sponge Dysidea avara (Xisha Is., South China Sea). Pharm: Cytotoxic. Ref: W. -H. Jiao, et al, Org. Lett., 2012, 14, 202 H

O

O O

913 Dysideavarone C Type: Other meroterpenoids. C23H28O3 Source: Sponge Dysidea avara (Xisha Is., South China Sea). Pharm: Cytotoxic. Ref: W. -H. Jiao, et al, Org. Lett., 2012, 14, 202 H

O

O O

914 Dysideavarone D Type: Other meroterpenoids. C23H28O3 Source: Sponge Dysidea avara (Xisha Is., South China Sea). Pharm: Cytotoxic. Ref: W. -H. Jiao, et al, Org. Lett., 2012, 14, 202 H

O

O O

915 Epoxyphomalin D Type: Other meroterpenoids. C22H34O4 White amorph. powder, [α]D20 = –235° (c = 0.18, acetone). Source: Marine-derived fungus Paraconiothyrium cf sporulosum from sponge Ectyoplasia ferox (Lauro Club Reef, Dominica, Caribbean). Pharm: Cytotoxic

346

6 Polyterpenoids and Meroterpenoids

(36 hmn tumour cell lines, mean IC50 = 6.12 μmol/L; selective prostate PC3M, IC50 = 0.72 μmol/L, bladder BXF-1218L, IC50 = 1.43 μmol/L). Ref: I. E. Mohamed, et al, JNP, 2010, 73, 2053 OH OH HO

O

H

916 Erythrolic acid D Type: Other meroterpenoids. C19H24O5 Source: Marine-derived bacterium Erythrobacter sp. (sediment, Trinity Bay, Galveston, Texas). Pharm: Cytotoxic (non-small cell lung cancer cells, modest). Ref: Y. Hu, et al, JOC, 2012, 77, 3401 OH

HO O

OH

O

917 Euplexide A Type: Other meroterpenoids. C34H48O11 Solid, mp 92–93 °C, [α]D25 = −2.5° (c. = 0.2, CHCl3). Source: Gorgonian Euplexaura anastomosans (Korea). Pharm: Cytotoxic (K462, IC50 = 2.6 μg/mL); antioxidant; PLA2 inhibitor (50 μg/mL, exihibitive rate = 52%). Ref: J. Shin, et al, JOC, 1999, 64, 1853 O

O O

O

O

9'R

O

O

OH 2

OH 4

O

OH

918 Euplexide B Type: Other meroterpenoids. C36H50O12 Solid,mp 170–180 °C, [α]D25 = −7.9° (c. = 0.2, CHCl3). Source: Gorgonian Euplexaura anastomosans (Korea). Pharm: Cytotoxic

6.7 Other Meroterpenoids

347

(K462, IC50 = 3.1 μg/mL); antioxidant; PLA2 inhibitor (50 μg/mL, exihibitive rate = 71%). Ref: J. Shin, et al, JOC, 1999, 64, 1853 O

O O

O

O

O O

O

O

OH

2

9'R

O

4

OH

919 Euplexide C Type: Other meroterpenoids. C34H48O10 Gum, [α]D25 = −11.9° (c. = 0.2, CHCl3). Source: Gorgonian Euplexaura anastomosans (Korea). Pharm: Cytotoxic (K462, IC50 = 5.2 μg/mL); antioxidant. Ref: J. Shin, et al, JOC, 1999, 64, 1853 O

O O

O

O O

O 9'R

OH

2

4

O

OH

920 Euplexide D Type: Other meroterpenoids. C34H48O11 Gum, [α]D25 = −13.1° (c. = 0.3, CHCl3). Source: Gorgonian Euplexaura anastomosans (Korea). Pharm: Cytotoxic (K462, IC50 = 8.1 μg/mL). Ref: J. Shin, et al, JOC, 1999, 64, 1853 O

O O

O

9'

O O

O

O 2

OH 4

OH

O

348

6 Polyterpenoids and Meroterpenoids

921 Euplexide E Type: Other meroterpenoids. C35H50O11 Gum, [α]D25 = −12.6° (c. = 0.2, CHCl3). Source: Gorgonian Euplexaura anastomosans (Korea). Pharm: Cytotoxic (K462, IC50 = 9.4 μg/mL); antioxidant. Ref: J. Shin, et al, JOC, 1999, 64, 1853 O O O

O

O O

O O

OH

2

O

OH

922 Euplexide F Type: Other meroterpenoids. C32H46O9 Gum, [α]D25 = −15.1° (c. = 0.07, MeOH). Source: Gorgonian Euplexaura anastomosans. Pharm: Cytotoxic (mild); PLA2 inhibitor. Ref: Y. Seo, et al, Nat. Prod. Lett., 2001, 15, 81 O HO

O

O OH

O

O O

OH

923 Euplexide G Type: Other meroterpenoids. C32H46O9 Gum, [α]D25 = −21.6° (c. = 0.12, MeOH). Source: Gorgonian Euplexaura anastomosans. Pharm: Cytotoxic (mild); PLA2 inhibitor. Ref: Y. Seo, et al, Nat. Prod. Lett., 2001, 15, 81 O HO

O

O O

OH

O

O OH

924 Expansol A Type: Other meroterpenoids. C30H38O5 Oil, [α]D23 = +4.4° (c = 0.09, MeOH). Source: Mangrove-derived fungus Penicillium expansum from mangrove Excoecaria agallocha (roots, China). Pharm: Cytotoxic (HL60, moderate). Ref: Z. Y. Lu, et al, JNP, 2010, 73, 911

6.7 Other Meroterpenoids

O

349

OH O

7

OH

OH

925 Expansol B Type: Other meroterpenoids. C29H36O5 Oil, [α]D23 = +7.3° (c = 0.03, MeOH). Source: Mangrove-derived fungus Penicillium expansum from mangrove Excoecaria agallocha (roots, China). Pharm: Cytotoxic (A549 and HL60, inhibits proliferation). Ref: Z. Y. Lu, et al, JNP, 2010, 73, 911 OH OH O

7

OH

OH

926 Farnesylhydroquinone Type: Other meroterpenoids. C21H30O2 Viscous oil. Source: Brown alga Dictyopteris undulata [Syn. Dictyopteris zonarioides] (yield = 0.015% fw), marine-derived fungus Penicillium sp. (mycelium). Pharm: Antifungal (Saccharomyces cerevisiae, MIC = 25 μg/mL; Sclerotinia libertiana, MIC = 25 μg/mL; Aspergillus oryzae, MIC = 12.5 μg/mL; Aspergillus niger, MIC = 12.5 μg/mL); antioxidant (DPPH scavenger, IC50 = 12.5 μmol/ L). Ref: M. Ochi, et al, Chem. Lett., 1979, 831│ M. Saleem, et al, NPR, 2007, 24, 1142 (rev) OH

OH

927 Fasciquinol A Type: Other meroterpenoids. C26H38O5S Source: Sponge Fasciospongia sp. (dredging, off southern Australia). Pharm: Antibacterial (gram-positive bacteria). Ref: H. Zhang, et al, Tetrahedron, 2011, 67, 2591

350

6 Polyterpenoids and Meroterpenoids

O O

H

H

S

OH O

OH

H

928 Fasciquinol B Type: Other meroterpenoids. C26H38O2 Source: Sponge Fasciospongia sp. (dredging, off southern Australia). Pharm: Antibacterial (gram-positive bacteria). Ref: H. Zhang, et al, Tetrahedron, 2011, 67, 2591 OH

H

H

OH

H

929 Frondosin A Type: Other meroterpenoids. C21H28O2 Powder, mp 111–113 °C, [α]D = +31.5° (c = 0.25, MeOH). Source: Sponge Dysidea frondosa. Pharm: PKC inhibitor (IC50 = 1.8 μmol/L); interleukin-8 receptor inhibitor (low micromolar range); anti-HIV. Ref: A. D. Patil, et al, Tetrahedron, 1997, 53, 5047│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) HO OH

930 (–)-Frondosin A Type: Other meroterpenoids. C21H28O2 Solid, [α]D = −210° (c. = 0.93, MeOH). Source: Sponge Euryspongia sp. (Chuuk, Micronesia). Pharm: HIV-1 inhibitor. Ref: Y. F. Hallock, et al, Nat. Prod. Lett., 1998, 11, 153

6.7 Other Meroterpenoids

351

HO OH

931 Frondosin B Type: Other meroterpenoids. C20H24O2 Gum, [α]D = +18.6° (c = 0.17, MeOH). Source: Sponge Dysidea frondosa (Pohnpei). Pharm: PKC inhibitor (IC50 = 4.8 μmol/L); interleukin-8 receptor inhibitor (low micromolar range). Ref: A. D. Patil, et al, Tetrahedron, 1997, 53, 5047│ M. Inoue, et al, JACS, 2001, 123, 1878│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) HO

O

932 Frondosin C Type: Other meroterpenoids. C21H26O2 Oil, [α]D = +9.4° (c = 0.12, MeOH). Source: Sponge Dysidea frondosa. Pharm: PKC inhibitor (IC50 = 20.9 μmol/L); interleukin-8 receptor inhibitor (low micromolar range). Ref: A. D. Patil, et al, Tetrahedron, 1997, 53, 5047│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O OH

933 (+)-Frondosin D Type: Other meroterpenoids. C21H26O3 Solid, [α]D = +29.6° (c = 0.2, MeOH). Source: Sponge Dysidea frondosa. Pharm: PKC inhibitor (IC50 = 26.0 μmol/L); interleukin-8 receptor inhibitor (low micromolar range). Ref: A. D. Patil, et al, Tetrahedron, 1997, 53, 5047│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev)

352

O

6 Polyterpenoids and Meroterpenoids

OH O

934 (–)-Frondosin D Type: Other meroterpenoids. C21H26O3 Yellow solid, [α]D = −211° (c. = 0.43, MeOH). Source: Sponge Euryspongia sp. (Chuuk, Micronesia). Pharm: HIV-1 inhibitor. Ref: Y. F. Hallock, et al, Nat. Prod. Lett., 1998, 11, 153 O

OH O

935 Frondosin E Type: Other meroterpenoids. C22H28O3 Oil, [α]D = +26.1° (c = 0.09, MeOH). Source: Sponge Dysidea frondosa. Pharm: PKC inhibitor (IC50 = 30.6 μmol/L); interleukin-8 receptor inhibitor (low micromolar range); anti-HIV. Ref: A. D. Patil, et al, Tetrahedron, 1997, 53, 5047│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O

O O

936 Glaciapyrrole A Type: Other meroterpenoids. C19H27NO4 Glass, [α]D22 = +16.8° (c = 0.02, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS008187 (psychrophilic, cold water, sediment, Alaska). Pharm: Cytotoxic (HT29 and B16 (F-10), IC50 = 180 μmol/L). Ref: V. R. Macherla, et al, JNP, 2005, 68, 780│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

6.7 Other Meroterpenoids

O

353

OH

OH

O NH

937 Guignardone B Type: Other meroterpenoids. C17H24O5 Source: Marine-derived Guignardia mangiferae, marine-derived fungus Guignardia sp. from mangrove Scyphiphora hydrophyllacea (leaves, Wenchang, Hainan, China). Pharm: Antibacterial (MRSA, 65 μmol/L, IZD = 8.0 mm). Ref: W. H. Yuan, et al, EurJOC, 2010, 33, 6348│ W. -L. Mei, et al, Mar. Drugs, 2012, 10, 1993 OH O

H

HO

O

O

938 Guignardone I Type: Other meroterpenoids. C17H26O5 Colorless oil, [α]D32 = −32° (c = 0.24, MeOH). Source: Marine-derived fungus Guignardia sp. from mangrove Scyphiphora hydrophyllacea (leaves, Wenchang, Hainan, China). Pharm: Antibacterial (65 μmol/L: Staphylococcus aureus, IZD = 9.0 mm; MRSA, IZD = 11.0 mm). Ref: W. -L. Mei, et al, Mar. Drugs, 2012, 10, 1993 OH O

H

O

O OH

939 Halicloic acid A Type: Other meroterpenoids. C38H56O5 Source: Sponge Haliclona sp. (Culasian Point, Leyte, Philippines). Pharm: Indoleamine 2,3-dioxygenase inhibitor. Ref: D. E. Williams, et al, JNP, 2012, 75, 1451

354

6 Polyterpenoids and Meroterpenoids

OH HOOC

H O

OH

H

H H

940 Halicloic acid B Type: Other meroterpenoids. C38H56O5 Source: Sponge Haliclona sp. (Culasian Point, Leyte, Philippines). Pharm: Indoleamine 2,3-dioxygenase inhibitor. Ref: D. E. Williams, et al, JNP, 2012, 75, 1451 OH HOOC

OH H

HO

H

H

941 Halioxepine Type: Other meroterpenoids. C26H38O4 Source: Sponge Haliclona sp. (Baubau, Buton I., Indonesia). Pharm: Antioxidant. Ref: A. Trianto, et al, CPB, 2011, 59, 1311 OH OH

HO O

942 Halisulfate 1 Type: Other meroterpenoids. C31H48O6S Needles, [α]D = −27.3° (c = 0.01, MeOH). Source: An unidentified sponge (family Halichondriidae), sponge Dysidea sp. (tropical). Pharm: Antibacterial (gram-positive bacteria); antibacterial (Bacillus subtilis, MIC ≈ 1.

6.7 Other Meroterpenoids

355

56–12.5 μg/mL, MMOA: isocitrate lyase inhibition); antifungal (Candida albicans); phospholipase A2 inhibitor; serine protease inhibitor. Ref: M. R. Kernan, et al, JOC, 1988, 53, 4574│ D. Lee, et al, BoMCL 2008, 18, 5377 HO

O O

OH S O OH

943 Hamigeran E Type: Other meroterpenoids. C18H23BrO5 Oil, [α]D25 = +30.5° (CHCl3) ((tri–Et ethe). Source: Sponge Hamigera tarangaensis (New Zealand). Pharm: Antibacterial (Staphylococcus aureus, Bacillus subtilis); antifungal (Candida albicans). Ref: R. C. Cambie, et al, JNP, 1995, 58, 940│ K. D. Wellington, et al, JNP, 2000, 63, 79 OH

OH

Br

O

O OH

H

944 2-Heptaprenyl-1,4-benzenediol-4-sulfate Type: Other meroterpenoids. C41H62O5S Source: Sponges Ircinia spinulosa (Adriatic Sea), Ircinia fasciculata (India) and Ircinia sp. (New Caledonia coast, depth of 425–500 m). Pharm: TPK inhibitor (IC50 = 8 μg/mL); toxic (brine shrimp lethality, LD50 = 0.02 ppm, fish lethality, LD50 = 15.6 ppm). Ref: Y. Venkateswarlu, et al, JNP, 1994, 57, 1286│ G. Bifulco, et al, JNP 1995, 58, 1444│ S. De Rosa, et al, JNP, 1995, 58, 1450│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev)

356

6 Polyterpenoids and Meroterpenoids

OH

O S O O O

H

945 Heptaprenylhydroquinone 2-Methyl-2-butenyl-geranylgeranylgeranyl-hydroquinone Type: Other meroterpenoids. C41H62O2 Source: Sponges Sarcotragus spinosulus (Callejones, Ceuta, Mediterranean Sea) and Hippospongia communis. Pharm: Cytotoxic (hmn CML K562 chronic myelogenous leukemia cell line, cell metabolism IC50 = 8 μmol/L, control Imatinib, cell metabolism IC50 = 0.4 μmol/L; cell number IC50 = 7 μmol/L, Imatinib, cell number IC50 = 0.5 μmol/L); antibacterial; analgesic. Ref: G. Cimino, et al, Tetrahedron, 1972, 28, 1401│ Y. F. Pouchus, et al, JNP, 1988, 51, 188│ C. Abed, et al, Mar. Drugs, 2011, 9, 1210 OH 5

OH

946 2-Hexaprenyl-1,4-benzenediol Hexaprenylhydroquinone Type: Other meroterpenoids. C36H54O2 Source: Sponges Ircinia spinulosa and Ircinia muscarum. Pharm: Analgesic; binds to neuropeptide Y receptor; TPK inhibitor; HIV-integrase inhibitor; ATP inhibitor. Ref: G. Cimino, et al, Tetrahedron, 1972, 28, 1401│ G. Bifulco, et al, JNP, 1995, 58, 1444 OH 4

OH

6.7 Other Meroterpenoids

357

947 Hipposulfate A Type: Other meroterpenoids. C31H46O6S Oil, [α]D = +8.1° (c = 0.31, MeOH). Source: Sponge Hippospongia cf. metachromia (Okinawa). Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all IC50S = 2μg/mL). Ref: M. Musman, et al, JNP, 2001, 64, 350

O O

O S

H

HO

O

16

OH

H

948 Homoplakotenin Type: Other meroterpenoids. C25H34O2 Oil, [α]D = +183° (c = 0.5, MeOH). Source: Sponge Plakortis lita (Palauan). Pharm: Inhibits DNA synthesis (rheumatoid synovial fibroblast, inhibitive rate = 73.5%). Ref: A. Qureshi, et al,JNP, 1999, 62, 1205│ J. W. Blunt, et al, NPR, 2014, 31, 160 (rev)

H H H COOH

949 Homoplakotenin sodium salt Type: Other meroterpenoids. C25H33O21− [α]D = +211° (c = 0.5, MeOH) (Na salt). Source: Sponge Plakortis lita (Palauan). Pharm: Inhibits DNA synthesis (rheumatoid synovial fibroblast, inhibitive rate = 27.8%). Ref: A. Qureshi, et al, JNP, 1999, 62, 1205

O O

358

6 Polyterpenoids and Meroterpenoids

950 (–)-Hyatellaquinone Type: Other meroterpenoids. C22H30O4 Source: Sponges Hyattella intestinalis (South Africa) and Spongia sp. (Australia). Pharm: HIV reverse transcriptase (HIV-rt) inhibitor. Ref: V. Paul, et al, Tet. Lett., 1980, 21, 2787│ R. J. Capon, et al, Aust J. Chem., 1993, 48, 1245 O O

O HO

H

951 (+)-Hyatellaquinone Type: Other meroterpenoids. C22H30O4 Oil, [α]D25 = +15.6° (c = 0.5, CHCl3). Source: Sponge Hyattella intestinalis. Pharm: HIV reverse transcriptase (HIV-rt) inhibitor. Ref: R. Talpir, et al, Tetrahedron, 1994, 50, 4179│ S. Poigny, et al, JOC, 1999, 64, 9318 O O

O OH

H

952 6ʹ-Hydroxyavarol Type: Other meroterpenoids. C21H30O3 Oil, [α]D25 = +60° (c = 0.02, MeOH). Source: Sponge Dysidea cinerea (Red Sea). Pharm: HIV reverse transcriptase inhibitor; DNA polymerase inhibitor. Ref: S. Hirsch,et al, JNP 1991, 54, 92│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) HO OH OH 4

12

6.7 Other Meroterpenoids

359

953 3’-Hydroxyavarone Avarone A Type: Other meroterpenoids. C21H28O3 Oil, [α]D25 = +45° (c = 0.06, CHCl3). Source: Sponge Dysidea cinerea (Red Sea). Pharm: Cytotoxic (P388, IC50 = 0.62 μg/ mL). Ref: S. Hirsch, et al, JNP, 1991, 54, 92│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH O O

4

12

954 5’-Hydroxy-2-heptaprenyl-1,4-benzenediol Type: Other meroterpenoids. C41H62O3 Source: Sponge Ircinia sp. (New Caledonia). Pharm: Binds to neuropeptide Y receptor; TPK inhibitor; HIV-integrase inhibitor. Ref: G. Bifulco, et al, JNP, 1995, 58, 1444 OH OH HO

955 25’-Hydroxy-2-octaprenyl-1,4-benzenediol-4-sulfate Type: Other meroterpenoids. C46H70O6S Source: Sponge Ircinia spinulosa (Adriatic Sea). Pharm: Toxic (brine shrimp lethality, LD50 = 0.05 ppm, fish lethality, LD50 = 19.6 ppm). Ref: S. De Rosa, et al, JNP, 1995, 58, 1450

360

6 Polyterpenoids and Meroterpenoids

OH

O S O O O

H

OH

956 19-Hydroxypolyfibrospongol B Type: Other meroterpenoids. C24H34O6 Amorph. solid, [α]D25 = +2.3° (c = 0.12, CHCl3). Source: Sponge Dysidea arenaria (South China Sea). Pharm: Cytotoxic (P388, KB16, A549, IC50 = 0.6–2.0 μg/mL). Ref: Y. Qiu, et al, Molecules, 2008, 13, 1275│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O HO

OH 19

O H

OH

O

957 9’-Hydroxysarquinone Type: Other meroterpenoids. C27H38O3 Yellow oil, [α]D21 = +2° (c = 1.9, CHCl3). Source: Brown alga Sargassum tortile. Pharm: Cytotoxic (P388, ED50 = 0.7 μg/mL, control Etoposide, ED50 = 0.24 μg/mL). Ref: Numata, et al, CPB, 1991, 39, 2129│ Rivera, P. et al, Can. J. Chem., 1990, 68, 1399 O

O

OH

6.7 Other Meroterpenoids

361

958 Ircinol sulfate Type: Other meroterpenoids. C31H50O5S Source: Sponge Ircinia sp. (New Caledonia). Pharm: Binds to neuropeptide Y receptor; TPK inhibitor; HIV-integrase inhibitor. Ref: G. Bifulco, et al, JNP, 1995, 58, 1444 O O

3

S

OH

O

O

959 Isojaspic acid Type: Other meroterpenoids. C27H38O3 Oil, [α]D27 = +9.3° (c = 0.4, CHCl3). Source: Sponges Cacospongia spp. Pharm: Antibacterial (Staphylococcus epidermidis, MIC = 2.5 μg/mL). Ref: B. K. Rubio, et al, JNP, 2007, 70, 628 HO OH O

H

960 Isometachromin Type: Other meroterpenoids. C22H30O4 Oil, [α]D = −9.6° (c = 0.08, CHCl3). Source: An unidentified sponge (deep water, family Spongiidae). Pharm: Cytotoxic (A549, IC50 = 2.6 μg/mL; P388, IC50 ≥ 10 μg/mL). Ref: O. J. McConnell, et al, Experientia. 1992, 48, 891 O O O OH

961 Isospongiaquinone Type: Other meroterpenoids. C22H30O4 Yellow crystal (hexane), mp 135.5–136 °C, [α]D20 = +64.8° (c = 1, CHCl3). Source: Sponge Fasciospongia rimosa [Syn. Stelospongia conulata]. Pharm: Antibacterial (Staphylococcus aureus). Ref: R. Kazlauskas, et al, Aust. J. Chem., 1978, 31, 2685│ R. J. Capon, JNP, 1990, 53, 753│ S. Urban, et al, JNP, 1992, 55, 1638

362

6 Polyterpenoids and Meroterpenoids

O HO

O O

962 5-epi-Isospongiaquinone Type: Other meroterpenoids. C22H30O4 Yellow–orange oil, [α]D20 = −41.2° (c = 1.08, CHCl3). Source: Sponges Hippospongia sp. (Palau) and Spongia hispida, sponges and marine animals, various animal organisms. Pharm: Antibacterial (Staphylococcus aureus, MIC = 20 μg/disc, Micrococcus sp., MIC = 20 μg/disc); cytotoxic (NCI-H460, HepG2, SF268, MCF7, HeLa, and HL60, inhibitory effects on maturation of starfish oocytes, and cell cycle arrest in HepG2 cell line were evaluated). Ref: S. Urban, et al, JNP, 1992, 55, 1638│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O O 1'

O

11

OH 9

12 8

963 Isozonarol Type: Other meroterpenoids. C21H30O2 Cryst. (CHCl3), mp 150–152 °C, [α]D22 = +28° (c = 1, CHCl3). Source: Brown alga Dictyopteris undulata [Syn. Dictyopteris zonaroides]. Pharm: Piscicide. Ref: W. Fenical, et al, JOC, 1973, 38, 2383│ G. Cimino, et al, Experientia, 1975, 31, 1250 HO

OH

H

6.7 Other Meroterpenoids

363

964 Liphagal Type: Other meroterpenoids. C22H28O4 Amorph. yellow solid, [α]D25 = +12° (c = 3.7, MeOH). Source: Sponge Aka coralliphaga (Dominica). Pharm: Phosphoinositide-3kinase PI3K inhibitor (IC50 = 100 nmol/L; 10 folder higher potency against PI3Kα than towards PI3Kγ); cytotoxic (hmn colon cancer cells, IC50 = 0.58 μmol/L; hmn breast cancer cells, IC50 = 1.58 μmol/L). Ref: F. Marion, et al, Org. Lett., 2006, 8, 321│ E. Alvarez-Manzaneda, et al, Org. Lett. 2010, 12, 4450│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH

O

HO

H O

H

965 Makassaric acid (+)-Makassaric acid Type: Other meroterpenoids. C27H38O3 Oil, [α]D25 = +7.3° (c = 5.4, MeOH). Source: Sponge Acanthodendrilla sp. Pharm: MAPKAP kinase 2 inhibitor (IC50 = 20 μmol/L). Ref: D. E. Williams, et al, JNP, 2004, 67, 2127│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O

OH

OH

966 Mamanuthaquinone Type: Other meroterpenoids. C22H30O4 Orange oil, [α]D = −31° (c = 0.058, CHCl3). Source: Sponge Fasciospongia sp. (Fiji islands). Pharm: Cytotoxic (HCT116, IC50 = 2 μg/mL); reverse transcriptase inhibitor. Ref: J. C. Swersey, et al, Tet. Lett., 1991, 32, 6687│ T. Yoon, et al, Angew. Chem., Int. Ed. Engl., 1994, 33, 853│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)

364

6 Polyterpenoids and Meroterpenoids

O

O

HO

O

H

967 Melemeleone B Type: Other meroterpenoids. C23H33NO5S Red amorph. solid, mp 190–200 °C, [α]D20 = −22° (c = 0.01, CH2Cl2). Source: Sponge Dysidea sp. (Solomon Is.). Pharm: Tyrosine kinase pp60V-SRC inhibitor (IC50 = 28 μmol/L). Ref: K. A. Alvi, et al, JOC, 1992, 57, 6604│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O

H

H N O

S O

O OH

4

12

968 Menzoquinone Type: Other meroterpenoids. C27H36O4 Oil. Source: Brown alga Desmarestia menziesii (psychrophilic, cold water, Antarctic). Pharm: Antibacterial (growth inhibition, MRSA (8 mm), MSSA (6 mm), VREF (7 mm), along with significant feeding deterrence against sea star Odontaster validus). Ref: S. Ankisetty, et al, JNP, 2004, 67, 1295│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O O OH O

969 Meroterphenol A Type: Other meroterpenoids. C27H38O5 Source: Brown alga Sargassum yezoense (Korea). Pharm: Activator of PPARγ (peroxisome proliferator-activated receptor γ, a nuclear receptor that plays a key role in energy metabolism, potent). Ref: M. C. Kim, et al, CPB, 2011, 59, 834

6.7 Other Meroterpenoids

OH

H

365

OH

HO O

OH

970 Meroterphenol B Type: Other meroterpenoids. C27H38O5 Source: Brown alga Sargassum yezoense (Korea). Pharm: Activator of PPARγ (peroxisome proliferator-activated receptor γ, a nuclear receptor that plays a key role in energy metabolism, potent). Ref: M. C. Kim, et al, CPB, 2011, 59, 834

OH

OH

HO O

OH

971 Meroterphenol C Type: Other meroterpenoids. C27H40O5 Source: Brown alga Sargassum yezoense (Korea). Pharm: Activator of PPARγ (peroxisome proliferator-activated receptor γ, a nuclear receptor that plays a key role in energy metabolism, potent). Ref: M. C. Kim, et al, CPB, 2011, 59, 834

OH OH HO O

OH

972 Meroterphenol D Type: Other meroterpenoids. C27H36O5 Source: Brown alga Sargassum yezoense (Korea). Pharm: Activator of PPARγ (peroxisome proliferator-activated receptor γ, a nuclear receptor that plays a key role in energy metabolism, potent). Ref: M. C. Kim, et al, CPB, 2011, 59, 834

OH

H

HO O

OH

OH

366

6 Polyterpenoids and Meroterpenoids

973 5’-Methoxy-(2E)-bifurcarenone Type: Other meroterpenoids. C28H40O5 Oil, [α]D25 = +10.7° (c = 1.5, EtOH). Source: Brown algae Cystoseira tamariscifolia (Morocoo), Cystoseira amentacea var. stricta and Cystoseira tamariscifolia. Pharm: Cytotoxic (ED50 = 12 μg/mL); antibacterial (Agrobacterium tumefaciens, IZD = 17 mm; Escherichia coli, IZD = 15 mm); antifungal (Botrytis cinerea, 1 μg, IZD = 24 mm, 5 μg, IZD = 29 mm, 10 μg, IZD = 33 mm, 15 μg, IZD = 37 mm, 20 μg, IZD = 39 mm; Fusarium oxysporum f. sp. lycopersici, 1 μg, IZD = 15 mm, 5 μg, IZD = 26 mm, 10 μg, IZD = 30 mm, 15 μg, IZD = 35 mm, 20 μg, IZD = 36 mm; Verticillium alboatrum, 1 μg, IZD = 17 mm, 5 μg, IZD = 25 mm, 10 μg, IZD = 31 mm, 15 μg, IZD = 38 mm, 20 μg, IZD = 38 mm). Ref: V. Mesguiche, et al, Phytochemistry, 1997, 45, 1489│ A. Bennamara, et al, Phytochemistry, 1999, 52, 37 OH

O

O

O OH

974 15-Methoxypuupehenol Type: Other meroterpenoids. C22H32O4 Needles, mp 124 °C, [α]D20 = −17° (c = 0.8, CHCl3). Source: Sponge Hyrtios sp. (New Caledonia). Pharm: Antibacterial (Staphylococcus aureus, IZD = 7 mm, 1 μg/disk); cytotoxic (KB cell lines, IC50 = 0.5 μg/mL); antimalarial (in vitro, CSPF F32, IC50 = 0.4 μg/mL, CRPF FcB1, IC50 = 1.4 μg/mL, CRPF PFB, IC50 = 1.2 μg/mL); LC50 (brine shrimp) = 20–30 μg/mL. Ref: M. -L. Bourguel-Kondracki, et al, JNP, 1999, 62, 1304 OH OH O O

975 975 3-Methoxy-5-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)1,2-benzenediol Type: Other meroterpenoids. C27H40O3 Oil Source: Sponge Fasciospongia sp. Pharm: Antimicrobial (weak). Ref: M. R. Kernan, et al, JNP, 1991, 54, 269

6.7 Other Meroterpenoids

367

O HO

HO

976 15α-Methyl-19,20-di-O-acetylpuupehenol Type: Other meroterpenoids. C26H36O5 Source: Some unidentified sponges (orders Verongida and Dictyoceratida). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 7%, weak). Ref: J. K. Zjawiony,et al, JNP, 1998, 61, 1502│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 O O O

O

O H H

977 15α-Methylpuupehenol Type: Other meroterpenoids. C22H32O3 Source: Some unidentified sponges (orders Verongida and Dictyoceratida). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 36%). Ref: J. K. Zjawiony,et al, JNP, 1998, 61, 1502│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 OH OH

O H H

978 2-Methyl-2-(tetraprenylmethyl)-2H-1-benzopyran-6-ol Type: Other meroterpenoids. C31H44O2 Source: Sponge Ircinia sp. (New Caledonia). Pharm: Binds to neuropeptide Y receptor; TPK inhibitor; HIV-integrase inhibitor. Ref: G. Bifulco, et al, JNP, 1995, 58, 1444

368

6 Polyterpenoids and Meroterpenoids

O

HO

979 Molokinenone Type: Other meroterpenoids. C20H29ClO3 Tan glass, [α]D = −400° (c = 0.012, MeOH). Source: Sponge Hyrtios sp. (Hawaii). Pharm: Cytotoxic (P388, IC50 = 5 μg/mL; A549, IC50 = 10 μg/mL; HT29, IC50 = 10 μg/mL); immunomodulator (MLR mixed lymphocyte reaction, IM activity, IC50 = 24 μg/mL; LCV lymphocyte viability, cytotoxic, IC50 > 50 μg/mL; potency, LCV/MLR > 2). Ref: S. S. Nasu, et al, JOC, 1995, 60, 7290 O Cl

OH OH

H

980 Moritoside Type: Other meroterpenoids. C34H48O11 Oil, [α]D23 = +22.6° (c = 0.1, CHCl3). Source: Gorgonian Euplexaura sp. Pharm: Inhibits development of starfish embryo; toxic (brine shrimp). Ref: N. Fusetani, et al, Tet. Lett., 1985, 26, 6449 O

O

O OH

OH

O

O

O OH

O

O

6.7 Other Meroterpenoids

369

981 Neoavarol Isoavarol Type: Other meroterpenoids. C21H30O2 Needles, mp 151–153 °C, [α]D = −38.6° (c = 0.1, CHCl3). Source: Sponge Dysidea sp. (Okinawa). Pharm: Ichthyotoxic. Ref: K. Iguchi, et al, CPB, 1990, 38, 1121│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) HO

OH

4

12

982 Neoavarone Type: Other meroterpenoids. C21H28O2 Yellow cryst., mp 78–79 °C, [α]D = −55.2° (c = 0.07, CHCl3). Source: Sponge Dysidea sp. (Okinawa). Pharm: Ichthyotoxic. Ref: K. Iguchi, et al, CPB, 1990, 38, 1121│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O

O

4

12

983 Neopetrosiquinone A Type: Other meroterpenoids. C21H20O4 Yellow oil. Source: Sponge Neopetrosia proxima (depth of 104 m, St Ann‘s Bay, Jamaica). Pharm: Cytotoxic (A549, IC50 > 14.8 μmol/L; PANC1, IC50 = 6.1 μmol/L; AsPC-1, IC50 = 6.1 μmol/L; DLD-1, IC50 = 3.7 μmol/L; NCIADR-Res, IC50 > 14.8 μmol/L). Ref: P. L. Winder, et al, BoMC, 2011, 19, 6599 O

O

O

H

O

370

6 Polyterpenoids and Meroterpenoids

984 Neopetrosiquinone B Type: Other meroterpenoids. C21H22O3 Yellow oil. Source: Sponge Neopetrosia proxima (depth of 104 m, St Ann‘s Bay, Jamaica). Pharm: Cytotoxic (A549, IC50 > 15.5 μmol/L; PANC1, IC50 = 13.8 μmol/L; AsPC-1, IC50 > 15.5 μmol/L; DLD-1, IC50 = 9.8 μmol/L; NCIADR-Res, IC50 > 15.5 μmol/L). Ref: P. L. Winder, et al, BoMC, 2011, 19, 6599 O

O

H

HO

985 15α-Nitroethyl-19,20-di-O-acetylpuupehenol Type: Other meroterpenoids. C27H37NO7 Source: Some unidentified sponges (orders Verongida and Dictyoceratida). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 15%, weak). Ref: J. K. Zjawiony,et al, JNP, 1998, 61, 1502│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 O O O

N

O

O

O

O H H

986 15α-Nitromethyl-19,20-di-O-acetylpuupehenol Type: Other meroterpenoids. C26H35NO7 Source: Some unidentified sponges (orders Verongida and Dictyoceratida). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 22%, weak). Ref: J. K. Zjawiony,et al, JNP, 1998, 61, 1502│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 O O O

N

O

O

O H H

O

6.7 Other Meroterpenoids

371

987 Nonaprenylhydroquinone Type: Other meroterpenoids. C51H78O3 Yellow solid. Source: Sponge Sarcotragus spinosulus (Callejones, Ceuta, Mediterranean Sea). Pharm: Cytotoxic (hmn CML K562 chronic myelogenous leukemia cell line, cell metabolism IC50 = 193 μmol/L, control Imatinib, cell metabolism IC50 = 0.4 μmol/L; cell number IC50 = 191 μmol/L, Imatinib, cell number IC50 = 0.5 μmol/L). Ref: C. Abed, et al, Mar. Drugs, 2011, 9, 1210 OH

OH

7

OH

988 Nonaprenylhydroquinone sulfate Type: Other meroterpenoids. C51H78O5S Yellow solid. Source: Sponge Sarcotragus sp. (Australia). Pharm: α11,3-Fucosyltransferase VII inhibitor (IC50 = 2.4 μg/mL). Ref: T. Wakimoto, et al, BoMCL, 1999, 9. 727 O O

S O

H

O 7

OH

989 Noscomin Type: Other meroterpenoids. C27H38O4 Amorph. solid, [α]D25 = +16° (c = 0.1, MeOH). Source: Cyanobacterium Nostoc commune. Pharm: Antibacterial (Bacillus cereus, Escherichia coli, Staphylococcus epidermidis). Ref: B. Jaki, et al, JNP, 1999, 62, 502 O

OH

H

HO

OH H

990 Octaprenylhydroquinone Type: Other meroterpenoids. C46H70O2 Source: Sponges Sarcotragus spinosulus (Callejones, Ceuta, Mediterranean Sea), Hippospongia communis, Ircinia spinulosa and Ircinia fasciculata. Pharm: Cytotoxic (hmn CML K562 chronic myelogenous

372

6 Polyterpenoids and Meroterpenoids

leukemia cell line, cell metabolism IC50 = 10 μmol/L, control Imatinib, cell metabolism IC50 = 0.4 μmol/L; cell number IC50 = 12 μmol/L, Imatinib, cell number IC50 = 0.5 μmol/L); muscle relaxant; analgesic. Ref: Y. F. Pouchus, et al, JNP, 1988, 51, 188│ C. Abed, et al, Mar. Drugs, 2011, 9, 1210 OH 6

OH

991 15-Oxopuupehenol Type: Other meroterpenoids. C21H28O4 Glass, [α]D = −106° (c = 0.52, MeOH). Source: Sponges Hyrtios spp., some unidentified sponges (orders Verongida and Dictyoceratida). Pharm: Cytotoxic (Vero, MIC = 3.4 μg/mL; KB, MIC = 10 μg/mL; LoVo, MIC = 5 μg/mL; P388, IC50 = 1 μg/mL; A549, IC50 = 0.5 μg/mL; HT29, IC50 = 2 μg/mL; CV-1, IC50 = 1 μg/mL; topoII, IC50 = 1 μg/mL); immunomodulator (MLR mixed lymphocyte reaction, IM activity, IC50 = 2.8 μg/mL; LCV lymphocyte viability, cytotoxic, IC50 > 50 μg/mL; potency, LCV/MLR > 18); antiviral (Mv 1 Lu/HSV I1, reduction > 10%; CV-1/MSV-1, reduction > 10%; BHK/VSV, reduction < 10%); antimalarial (Plasmodium falciparum D6 clone, IC50 = 2.0 μg/mL; Plasmodium falciparum W2 clone, IC50 = 1.3 μg/mL); antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 7%, weak). Ref: M. T. Hamann,et al, JOC, 1993, 58, 6565│ S. S. Nasu, et al, JOC, 1995, 60, 7290│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949│ E. J. Alvarez-Manzaneda, et al, Org. Lett., 2005, 7, 1477 OH OH O O

H

992 Penicillipyrone B Type: Other meroterpenoids. C21H28O4 Source: Marine-derived fungus Penicillium sp. (sediment). Pharm: Cytotoxic (murine hepatoma cells, elicited significant inductor of quinone reductase indicating a possible cancer preventative role). Ref: L. Liao, et al, JNP, 2014, 77, 406

6.7 Other Meroterpenoids

373

O O

O H

O

H

993 Penicilliumin A Type: Other meroterpenoids. C22H32O4 White crystalline solid, [α]D20 = −0.008° (c = 0.85, CHCl3). Source: Deep-sea fungus Penicillium sp. F00120 (sediment). Pharm: Cytotoxic (B16, GI50 = 22.88 μg/mL; A375, GI50 = 27.37 μg/mL; HeLa, GI50 = 44.05 μg/mL). Ref: X. Lin, et al, Mar. Drugs, 2012, 10, 106 O

OH

HO H

O

H

994 2-Pentaprenyl-1,4-benzenediol-4-sulfate Type: Other meroterpenoids. C31H46O5S Source: Sponge Ircinia sp. (New Caledonia coast, depth of 425–500 m). Pharm: Binds to neuropeptide Y receptor; HIVintegrase inhibitor; TPK inhibitor (IC50 = 8 μg/mL). Ref: G. Bifulco, et al, JNP 1995, 58, 1444│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH

O

S O

O O

H

995 Peyssonol A Type: Other meroterpenoids. C22H29BrO3 Oil, [α]D25 = +2.0° (c = 0.1, CHCl3). Source: Red alga Peyssonnelia sp. (Red Sea). Pharm: HIV reverse transcriptase inhibitor. Ref: R. Talpir, et al, Tetrahedron, 1994, 50, 4179

374

6 Polyterpenoids and Meroterpenoids

H O HO

OH H

Br

H

996 Peyssonol B Type: Other meroterpenoids. C24H32O4 Oil, [α]D25 = −57° (c = 0.1, CHCl3). Source: Red alga Peyssonnelia sp. (Red Sea). Pharm: HIV reverse transcriptase inhibitor. Ref: R. Talpir, et al, Tetrahedron, 1994, 50, 4179

OH O

H

O OH

997 Plakotenin Type: Other meroterpenoids. C24H32O2 Oil. Source: Sponge Plakortis lita. Pharm: Cytotoxic (L1210, IC50 = 5.4 μg/mL; KB, IC50 = 7.4 μg/mL); inhibits DNA synthesis (rheumatoid synovial fibroblast, inhibitive rate = 76.8%). Ref: J. Kobayashi, et al, Tet. Lett., 1992, 33, 2579│ A. Qureshi, et al, JNP, 1999, 62, 1205 H

H HOOC

998 Polyfibrospongol A Type: Other meroterpenoids. C24H34O4 Amorph. solid, [α]D25 = +5.3° (c = 0.3, CHCl3). Source: Sponges Polyfibrospongia australis (Taiwan) and Dysidea arenaria (South China Sea). Pharm: Cytotoxic (P388, IC50 = 0.7 μg/mL, KB16, IC50 = 1.4 μg/mL, A549, IC50 = 0.6 μg/mL). Ref: Y. -C. Shen, et al, JNP, 1997, 60, 93│ Y. Qiu, et al, Molecules, 2008, 13, 1275│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)

6.7 Other Meroterpenoids

375

O HO O H

O

999 Polyfibrospongol B Type: Other meroterpenoids. C24H34O5 Amorph. solid, [α]D25 = +1.8° (c = 0.18, CHCl3). Source: Sponges Polyfibrospongia australis (Taiwan) and Dysidea arenaria (South China Sea). Pharm: Cytotoxic (P388, IC50 = 1.0 μg/mL, KB16, IC50 = 2.0 μg/ mL, A549, IC50 = 1.0 μg/mL). Ref: Y. -C. Shen, et al, JNP, 1997, 60, 93│ Y. Qiu, et al, Molecules, 2008, 13, 1275│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O HO O H

OH

O

1000 Pseudoalteromone A Type: Other meroterpenoids. C18H24O5 Source: Marine-derived bacterium Pseudoalteromonas sp. CGH2XX from soft coral Lobophytum crassum (cultured-type, Taiwan). Pharm: Cytotoxic (Molt4, IC50 = 3.8 μg/mL; T47D, IC50 = 4.0 μg/mL); antioxidant (10 μg/mL, hmn neutrophils, inhibits generation of superoxide anion, InRt = 38.0%); elastase release inhibitor (10 μg/mL, hmn neutrophils, InRt = 20.2%). Ref: Y. -H. Chen, et al, Mar. Drugs, 2012, 10, 1566 O

O

O O O

1001 Puupehedione Type: Other meroterpenoids. C21H26O3 [α]D = +208° (c = 0.087, MeOH). Source: Sponge Verongida sp. (Hawaii). Pharm: Antimicrobial (inhibition halos, between

376

6 Polyterpenoids and Meroterpenoids

10 mm and 17 mm); cytotoxic (neoplastic cell lines analyzed, minimum inhibitory concentration values between 1 μg/mL and 2 μg/mL). Ref: N. T. Hamann, et al, JOC, 1993, 58, 6565│ S. S. Nasu,et al, JOC, 1995, 60, 7290│ S. Urban, et al, JNP, 1996, 59, 900│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O O

O

1002 (–)-Puupehenone Type: Other meroterpenoids. C21H28O3 mp 124 °C, [α]D20 = −17° (c = 0.8, CHCl3). Source: Sponge Hyrtios sp. (New Caledonia). Pharm: Cytotoxic (KB, LoVo, MIC50 = 5.1 μg/mL, P388, A549, HT29, CV-1, IC50 = 0.25 μg/mL, 0.5 μg/mL, 0.5 μg/mL, 0.5 μg/ mL, respectively); antifungal (6 mm disk, 50 μg/disk: Aspergillus oryzae, Penicillium notatum, Trichophyton mentagrophytes, Saccharomyces cerevisiae, Candida albicans, IZD = 25 mm, 30 mm, 10 mm, 12 mm, 11 mm, respectively); antimalarial (in vitro, CSPF F32, IC50 = 0.6 μg/mL); LC50 (brine shrimp) = 20–30 μg/mL. Ref: M. L. Bourguel-Kondracki, et al, JNP, 1999, 62, 1304 OH O

O

1003 (+)-Puupehenone Type: Other meroterpenoids. C21H28O3 Cryst. (hexane), mp 129–130 °C, [α]D = +315° (c = 1.64, CCl4). Source: Sponges Strongylophora hartmani (deep water, off Bahamas), Hyrtios eubamma and Dysidea sp., other sponges and marine organisms. Pharm: Cytotoxic (P388, IC50 = 1 μg/mL; A549, IC50 = 0.1–1 μg/mL; HCT8, IC50 = 1–10 μg/mL; MCF7, IC50 = 0.1–1 μg/mL); antineoplastic (P388 in vivo, 25 mg/kg administered daily for 9 days, T/C = 119%); cytotoxic (A549 and HT29, IC50 = 0.5 μmol/L; even better inhibition values against the synthesis of DNA and RNA, 0.3 μg/mL and 0.4 μg/mL respectively); antifungal (especially Penicillium notatum and Aspergillus oryzae); antifungal (Candida albicans, MIC = 3 μg/mL); antituberculosis (Mycobacterium

6.7 Other Meroterpenoids

377

tuberculosis H37Rv, 12.5 μg/mL, InRt = 99%, MIC = 12.5 μg/mL, IC50 = 2.0 μg/mL); enzyme inhibitor; insecticide. Ref: B. N. Ravi, et al, Pure Appl. Chem., 1979, 51, 1893│ P. Amade, et al, Helv. Chim. Acta, 1983, 66, 1672│ S. Kohmoto, et al, JNP 1987, 50, 336│ M. T. Hamann,et al, JOC, 1993, 58, 6565│ S. S. Nasu,et al, JOC, 1995, 60, 7290│ S. Urban, et al, JNP, 1996, 59, 900│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)│ CRC Press, DNP on DVD, 2012, version 20.2 OH O

21 15

O H H

1004 Renierin B Type: Other meroterpenoids. C22H28O4 Yellowish oil. Source: Sponge Reniera mucosa (Spain). Pharm: Antioxidant (DPPH scavenger, IC50 = 35 μmol/L). Ref: E. Zubia, et al, Tetrahedron, 1994, 50, 8153│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O HO

O

OH

1005 Rietone Type: Other meroterpenoids. C24H32O6 Orange oil, [α]D19 = +95° (c = 0.8, CHCl3). Source: Soft coral Alcyonium fauri (South Africa). Pharm: Cytotoxic (anti-oesophageal cancers: WHCO1, IC50 = 49.1 μmol/L; WHCO5, IC50 = 32.2 μmol/L; WHCO6, IC50 = 40.9 μmol/L; KYSE70, IC50 > 100.0 μmol/L; KYSE180, IC50 = 50.6 μmol/L; KYSE520, IC50 = 84.9 μmol/L; MCF12, IC50 = 7.3 μmol/L); anti-HIV (IC50 = 9.32 μmol/L, EC50 = 1.23 μmol/L). Ref: G. J. Hooper, et al, Tet. Lett., 1995, 3265│ R. A. Keyzers, et al, Tetrahedron, 2006, 62, 2200 OH

O 8'

O OH

O OH

378

6 Polyterpenoids and Meroterpenoids

1006 Rossinone A Type: Other meroterpenoids. C21H28O4 Source: Ascidian Aplidium sp. (Antarctic). Pharm: Anti-inflammatory; antiproliferative. Ref: D. R. Appleton, et al, JOC, 2009, 74, 9195 OH O

OH

OH

1007 Rossinone B Type: Other meroterpenoids. C21H24O5 Source: Ascidian Aplidium sp. (Antarctic). Pharm: Anti-inflammatory; antiproliferative. Ref: D. R. Appleton, et al, JOC, 2009, 74, 9195

O

O O H H

O

OH

1008 Sacrohydroquinone sulfate A Type: Other meroterpenoids. C36H54O5S Amorph. Source: Sponges Ircinia sp. (New Caledonia coast, depth of 425–500 m) and Sarcotragus spinulosus. Pharm: Na/KATPase inhibitor; TPK inhibitor (IC50 = 4 μg/mL). Ref: V. A. Stonik, et al, JNP, 1992, 55, 1256│ G. Bifulco,et al, JNP 1995, 58, 1444│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH 3

O

S O

O OH

1009 Sacrohydroquinone sulfate B Type: Other meroterpenoids. C41H62O8S2 Source: Sponge Sarcotragus spinulosus (deep water). Pharm: Na/K-ATPase inhibitor. Ref: V. A. Stonik, et al, JNP, 1992, 55, 1256

6.7 Other Meroterpenoids

O O

S

O H O 7

O

S O

379

H

O O H

1010 Sacrohydroquinone sulfate C Type: Other meroterpenoids. C46H70O5S Source: Sponges Sarcotragus spinulosus (deep water), Ircinia spinulosa (Adriatic Sea) and Sarcotragus sp. (Australia). Pharm: Toxic (brine shrimp lethality, LD50 = 0.04 ppm, fish lethality, LD50 = 16.9 ppm); α11,3-fucosyltransferase VII inhibitor (IC50 = 3.9 μg/mL); Na/K-ATPase inhibitor. Ref: V. A. Stonik, et al, JNP, 1992, 55, 1256│ S. De Rosa, et al, JNP, 1995, 58, 1450│ T. Wakimoto, et al, BoMCL, 1999, 9. 727 OH

O S O O OH

1011 Sarcochromenol A 2-Methyl-2-(pentaprenylmethyl)-2H-1-benzopyran-6-ol Type: Other meroterpenoids. C36H52O2 Crystals (EtOH) (Ac), mp 25–26 °C (Ac), [α]578.00 = +39.2° (CHCl3) (Ac). Source: Sponge Ircinia sp. (New Caledonia). Pharm: Binds to neuropeptide Y receptor; TPK inhibitor; HIV-integrase inhibitor. Ref: G. Bifulco, et al, JNP, 1995, 58, 1444

380

HO

6 Polyterpenoids and Meroterpenoids

O

1012 Sarcochromenol B 2-(Hexaprenylmethyl)-2-methyl-2H-1-benzopyran-6-ol Type: Other meroterpenoids. C41H60O2 Oil, [α]D = +3.6° (c = 1, CHCl3). Source: Sponges Ircinia sp. (New Caledonia) and Ircinia fasciculata (India). Pharm: Binds to neuropeptide Y receptor; TPK inhibitor; HIV-integrase inhibitor. Ref: Y. Venkateswarlu, et al, JNP, 1994, 57, 1286│ G. Bifulco, et al, JNP, 1995, 58, 1444

HO

O

1013 Sargachromenol 2,8-Dimethyl-2-(4,12-dimethyl-8-carboxy-3,11-tridecadienyl)-2H-1-benzopyran-6-ol Type: Other meroterpenoids. C27H36O4 Oil. Source: Brown alga Sargassum serratifolium. Pharm: Nervous system activity (butyrylcholinesterase inhibitor, IC50 = 26 nmol/L). Ref: T. Kusumi, et al, Chem. Lett., 1979, 277│ B. W. Choi, et al, Phytother. Res. 2007, 21, 423

6.7 Other Meroterpenoids

O

381

OH

O 8

HO

1014 Sargadiol I Type: Other meroterpenoids. C27H38O3 Pale brown oil, [α]D23 = +1.5° (c = 0.78, CHCl3). Source: Brown alga Sargassum tortile. Pharm: Cytotoxic (P388, ED50 = 14.0 μg/mL, control Etoposide, ED50 = 0.24 μg/mL); hepatotoxin; anthelmintic. Ref: A. Numata, et al, CPB, 1991, 39, 2129│ A. Numata, et al, Phytochemistry, 1992, 31, 1209

O

OH

HO

1015 Sargadiol II Type: Other meroterpenoids. C27H38O3 Pale brown oil, [α]D23 = +1.8° (c = 0.98, CHCl3). Source: Brown alga Sargassum tortile. Pharm: Cytotoxic (P388, ED50 = 16.8 μg/mL, control Etoposide, ED50 = 0.24 μg/mL). Ref: A. Numata, et al, CPB, 1991, 39, 2129

O

OH

HO

1016 Sargaol Type: Other meroterpenoids. C27H38O2 Pale brown oil. Source: Brown alga Sargassum tortile, soft coral Nephthea sp. Pharm: Cytotoxic (P388, ED50 = 20.8 μg/mL, control Etoposide, ED50 = 0.24 μg/mL). Ref: B. F. Bowden, et al, Aust. J. Chem., 1981, 34, 2677│ A. Numata, et al, CPB, 1991, 39, 2129│ A. Numata, et al, Phytochemistry, 1992, 31, 1209

O HO

1017 Sargasal I Type: Other meroterpenoids. C17H20O3 Pale brown oil. Source: Brown alga Sargassum tortile. Pharm: Cytotoxic (P388, ED50 = 5.8 μg/mL, control Etoposide, ED50 = 0.24 μg/mL).

382

6 Polyterpenoids and Meroterpenoids

Ref: A. Numata, et al, CPB, 1991, 39, 2129│ A. Numata, et al, Phytochemistry, 1992, 31, 1209

O

O

HO

1018 Sargasal II Type: Other meroterpenoids. C17H18O3 Pale brown oil. Source: Brown alga Sargassum tortile. Pharm: Cytotoxic (P388, ED50 = 5.7 μg/mL, control Etoposide, ED50 = 0.24 μg/ mL). Ref: A. Numata, et al, CPB, 1991, 39, 2129│ A. Numata, et al, Phytochemistry, 1992, 31, 1209

O

O

HO

1019 Scabellone B Type: Other meroterpenoids. C34H42O6 Source: Ascidian Aplidium scabellum (Hauraki Gulf, New Zealand). Pharm: Antiplasmodial (DRPF, moderate). Ref: S. T. S. Chan, et al, JOC, 2011, 76, 9151 O

O

O O

HO

O

1020 Shaagrockol B Type: Other meroterpenoids. C36H56O12S2 [α]D = +4° (c = 0.5, MeOH) (di–Na salt). Source: Sponge Toxiclona toxius (Red Sea). Pharm: Antifungal (yeast Candida albicans, IC50 = 6 μg/mL). Ref: S. Isaacs, et al, Tet. Lett., 1992, 33, 2227

6.7 Other Meroterpenoids

383

O O

O

O

S O

O

H OH

O

O S

O H H O

O

1021 Shaagrockol C Type: Other meroterpenoids. C36H56O10S2 [α]D = +8° (c = 0.7, MeOH) (di–Na salt). Source: Sponge Toxiclona toxius (Red Sea). Pharm: Antifungal (yeast Candida albicans, IC50 = 6 μg/mL). Ref: S. Isaacs, et al, Tet. Lett., 1992, 33, 2227 O O

O

S O

O H

H OH

H

O

O S

H O

O

1022 Siphonodictyal C Type: Other meroterpenoids. C22H30O7S Oil, [α]D = −23.6° (c = 0.47, MeOH). Source: Sponges Aka sp. and Siphonodictyon coralliphagum. Pharm: CDK/cyclin D1 inhibitor (IC50 = 9.0 μg/mL). Ref: V. Mukku,et al, JNP, 2003, 66, 686│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O O HO

S O

O

H OH

OH

H

1023 Siphonodictyal sulfate Type: Other meroterpenoids. C22H32O7S Source: Sponge Aka coralliphaga (Quintana Roo, Mexico). Pharm: Antioxidant. Ref: L. K. Shubina, et al, Nat. Prod. Commun., 2012, 7, 487

384

O HO

6 Polyterpenoids and Meroterpenoids

S

O

O

OH

OH O

H

1024 Smenorthoquinone Type: Other meroterpenoids. C23H32O4 Yellow needles (MeOH). Source: Sponge Smenospongia sp. Pharm: Cytotoxic (L1210, IC50 = 1.5 μg/mL); antimicrobial. Ref: S. Urban, et al, JNP, 1992, 55, 1638│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O O 1'

O

11

OH 9

12 8

1025 Smenospondiol Dictyoceratin A Type: Other meroterpenoids. C23H32O4 Needles, mp 180–182 °C, [α]D = +12.8° (c = 0.9, CHCl3). Source: Sponges Smenospongia spp. (dichloromethane extracts) and Hippospongia sp. Pharm: Cytotoxic (differentiation-inducing activity to K562 cells into erythroblast, lowest effective concentration = 15 μmol/L); cytotoxic (P388, KB16, A549, IC50 = 0.6–2.0 μg/mL); antibacterial (Staphyrococcus aureus, MIC = 6.3 μg/mL; Bacillus subtilis, MIC = 3.1 μg/mL). Ref: H. Nakamuta, et al, Tetrahedron, 1986, 42, 4197│ M. L. Kondracki, et al, Tetrahedron, 1989, 45, 1995│ M. L. Kondracki, et al, J. Chem. Res. Synop., 1989, 3, 74│ Y. Haruo, et al, Synlett, 2001, 1935│ S. Aoki, et al, CPB, 2004, 52, 935│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH HO 17

19

O H

22

O

6.7 Other Meroterpenoids

385

1026 (–)-Sporochnol A Type: Other meroterpenoids. C16H22O Pale yellow gum. Source: Brown alga Sporochnus bolleanus. Pharm: Antifeedant (fish). Ref: Y. C. Shen, et al, Phytochemistry, 1993, 32, 71│ A. Fadel, et al, Tetrahedron: Asymmetry, 1999, 10, 1153│ Y. Li, et al, J. Chem. Res. (S), 2000, 530

HO

1027 (+)-Sporochnol A Type: Other meroterpenoids. C16H22O Amorph. solid, [α]D = +10° (c = 1, CHCl3). Source: Brown alga Sporochnus bolleanus (Caribbean). Pharm: Antifeedant (fish). Ref: Y. -C. Shen, et al, Phytochemistry, 1993, 32, 71

HO

1028 Sporochnol C Type: Other meroterpenoids. C16H22O2 Pale yellow gum. Source: Brown alga Sporochnus bolleanus (Caribbean). Pharm: Antifeedant. Ref: Y. -C. Shen, et al, Phvtochemistrv, 1993, 32, 71 HO

OH

1029 Strongylin A Sch 50678 Type: Other meroterpenoids. C22H32O3 Oil, [α]D20 = +72° (c = 0.023, CH2Cl2). Source: Sponges Strongylophora hartmani and Xestospongia wiedenmayeri. Pharm: Cytotoxic (P388, IC50 = 13 μg/mL); antiviral (influenza PR-8, IC50 = 6.5 μg/mL, IT = 9). Ref: A. E. Wright, et al, JNP, 1991, 54, 1108│ S. J. Coval, et al, BoMCL, 1995, 5, 605│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)

386

6 Polyterpenoids and Meroterpenoids

O HO O

1030 Strongylophorine 1 Type: Other meroterpenoids. C27H38O4 Cryst., mp 160 °C, [α]D = −27° (c = 0.5, CHCl3). Source: Sponge Strongylophora durissima. Pharm: Ichthyotoxin. Ref: J. C. Braekman, et al, Bull. Soc. Chim. Belg., 1978, 87, 917 O

H

O

H

H O

OH

1031 Strongylophorine 2 Type: Other meroterpenoids. C26H34O4 Oil. Source: Sponge Strongylophora durissima. Pharm: Ichthyotoxin. Ref: J. C. Braekman, et al, Bull. Soc. Chim. Belg., 1978, 87, 917 O

O O H

H

OH

H

1032 Strongylophorine 3 Type: Other meroterpenoids. C26H36O4 Cryst., mp 183–186 °C, [α]D = −35° (c = 0.32, CH2Cl2). Source: Sponge Strongylophora durissima. Pharm: Ichthyotoxin. Ref: J. C. Braekman, et al, Bull. Soc. Chim. Belg., 1978, 87, 917 O

H H O

OH

H

OH

6.7 Other Meroterpenoids

387

1033 (14R)-Stypodiol epi-Stypodiol Type: Other meroterpenoids. C27H40O3 Oil, [α]D = −4.5° (c = 1.4, CHCl3). Source: Brown alga Stypopodium zonale. Pharm: Narcotic; hyperactive effects upon reef-dwelling dish (Eupomacentrus leucostictus); ichthyotoxin. Ref: W. H. Gerwick, et al, Tet. Lett., 1979, 20, 145│ W. H. Gerwick, et al, JOC, 1981, 46, 22│ A. Abad, et al, JOC, 1998, 63, 5100 O 14R

H HO

OH

H

1034 (–)-Stypoldione Type: Other meroterpenoids. C27H38O4 Red cryst. (Et2O), mp 170° (dec), [α]D = −65.1° (c = 0.46, CHCl3). Source: Brown algae Stypopodium zonale and Stypopodium flabelliforme, sea hare Aplysia dactylomela. Pharm: Cytotoxic (sea urchin eggs); ichthyotoxic; cell division inhibitor (fertilized sea urchin egg assay, 1.1 μg/mL); inhibits polymerization of microtubules (in vitro, with a novel mechanism); phospholipase A2 inhibitor. Ref: W. H. Gerwick, et al, Tet. Lett., 1979, 145│ W. H. Gerwick, et al, JOC, 1981, 46, 22│ T. O‘Brien, et al, Mol. Pbarmacol., 1983, 24, 493│ R. S. Jacobs, et al, Tetrahedron, 1985, 41, 981│ W. H. Gerwick, et al, J. Chem. Ecol., 1989, 15, 677│ J. Rovirosa, et al, Bol. Soc. Chil. Quim., 1994, 39, 219│ K. Mori, et al, Liebigs Ann., 1995, 1755│ A. Abad, et al, Synlett, 1996, 913

O H HO H

O

O

1035 Stypoquinonic acid Type: Other meroterpenoids. C27H38O4 Oil, [α]D25 = +68.9° (c = 0.27, MeOH). Source: Brown alga Stypopodium zonale (Canary Is., Spain). Pharm: Tyrosine kinase inhibitor (IC50 = 79.7 μg/mL); antibacterial (Bacillus megaterium, Escherichia coli, weak). Ref: M. Wessels, et al, JNP, 1999, 62, 927 O HOOC H O

388

6 Polyterpenoids and Meroterpenoids

1036 Stypotriol Type: Other meroterpenoids. C27H40O4 Oil, [α]D25 = −10° (c = 0.82, CHCl3). Source: Brown alga Stypopodium zonale. Pharm: Toxin. Ref: W. H. Gerwick, et al, Tet. Lett., 1979, 145│ W. H. Gerwick, et al, JOC, 1981, 46, 22

O H HO

H

HO

OH

1037 (+)-Subersic acid Type: Other meroterpenoids. C27H38O3 Oil, [α]D25 = +39.3° (c = 3.26, MeOH). Source: Sponge Acanthodendrilla sp. Pharm: MAPKAP kinase 2 inhibitor (IC50 = 9.6 μmol/L). Ref: D. E. Williams, et al, JNP, 2004, 67, 2127│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) HO O OH

H

1038 (–)-Subersic acid Type: Other meroterpenoids. C27H38O3 Source: Sponge Jaspis splendens. Pharm: Lipoxygenase inhibitor (hmn). Ref: J. Carroll, et al, JOC, 2001, 66, 6847 HO COOH

H

1039 epi-Taondiol Type: Other meroterpenoids. C27H40O3 Cryst. (Et2O), mp 149–152 °C, [α]D = +43.1° (c. = 1.03, CHCl3). Source: Brown algae Stypopodium zonale and Stypopodium flabelliforme, sea hare Aplysia dactylomela. Pharm: Cytotoxic; ichthyotoxin; antimitotic, algicide. Ref: W. H. Gerwick, et al, JOC, 1981, 46, 22│ F. Sánchez-Ferrando, et al, JOC, 1995, 60, 1475│ M. A. Muñoz, et al, Heterocycles, 2012, 85, 1961

6.7 Other Meroterpenoids

O O

H

389

O O

H

O

1040 Terretonin F Type: Other meroterpenoids. C26H30O8 Powder, [α]D25 = −19° (c = 0.8, CHCl3). Source: Marine-derived fungus Aspergillus insuetus from sponge Petrosia ficiformis (Mediterranean). Pharm: Mitochondrial respiratory chain inhibitor (mammalian, interacting with NADH oxidase). Ref: M. P. Lopez-Gresa, et al, JNP, 2009, 72, 1348 O

O H O OH

O O O

O

1041 Terretonin G Type: Other meroterpenoids. C27H38O9 Source: Marine-derived fungus Aspergillus sp. OPMF00272. Pharm: Antibacterial (20 μg/disk: gram-positive bacteria Staphylococcus aureus, IZ = 4 mm; Bacillus subtilis, IZ = 2 mm; Micrococcus luteus, IZ = 2 mm). Ref: T. Fukuda, et al, J. Antibiot., 2014, 67, 593 O HO

O O O

H O

H

OH

O

O

1042 Territrem B Type: Other meroterpenoids. C29H34O9 Needles (CHCl3), mp 200–203 °C, [α]D = +131° (c = 0.6, CHCl3). Source: Marine-derived fungus Aspergillus terreus PT06-2 (Grown in high salt medium 10% salinity). Pharm: Acetylcholin esterase inhibitor (strong); tremorgenic toxin. Ref: Y. Wang, et al, Mar. Drugs, 2011, 9, 1368

390

6 Polyterpenoids and Meroterpenoids

OH O

O

O

OH

O

O

O O

1043 2-Tetraprenylbenzoquinol Type: Other meroterpenoids. C26H38O2 Oil. Source: Sponges Ircinia spinulosa and Ircinia muscarum. Pharm: Analgesic. Ref: G. Cimino, et al, Experientia, 1972, 28, 1401│ Y. Venkateswarlu, et al, JNP, 1994, 57, 1286│ S. Bouzbouz, et al, Synthesis, 1994, 714 OH

OH

1044 α-Tocomonoenol Marine derived tocopherol Type: Other meroterpenoids. C29H48O2 Source: Salmon fish Oncorhynchus keta (eggs, Pacific Ocean). Pharm: Antioxidant (identical to that of α-Tocopherol). Ref: Y. Yamamoto, et al, JNP, 1999, 62, 1685

HO O

1045 δ-Tocotrienol 3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol Type: Other meroterpenoids. C27H40O2 Oil. Source: Brown algae Cystophora expansa and Sargassum tortile. Pharm: Induces hydroid Conjue uchidal settling (hydroid Conjue uchidal is epiphytic on brown alga Sargassum tortile. The “juice” of Sargassum tortile was shown to cause setting of Conjue Uchidai). Ref: R. Kazlauskas, et al, Aust. J. Chem., 1981, 34, 439│ T. Kato, et al, Experientia, 1975, 31, 433│ T. Kato, et al, Chem. Lett., 1975, 335

6.7 Other Meroterpenoids

8

O

391

2

HO

1046 δ-Tocotrinol epoxide Type: Other meroterpenoids. C27H40O3 Source: Brown alga Sargassum tortile. Pharm: Induces hydroid Conjue uchidal settling (hydroid Conjue uchidal is epiphytic on brown alga Sargassum tortile. The “juice” of Sargassum tortile was shown to cause setting of Conjue Uchidai). Ref: T. Kato, et al, Experientia, 1975, 31, 433│ T. Kato, et al, Chem. Lett., 1975, 335

O

O

HO

1047 15α,19,20-Tri-O-acetylpuupehenol Type: Other meroterpenoids. C27H36O7 Source: Two unidentified sponges (order Verongida and order Dictyoceratida). Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 78%). Ref: J. K. Zjawiony,et al, JNP, 1998, 61, 1502│ A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 O O O

O

O

O O H H

1048 Tricycloalternarene A Type: Other meroterpenoids. C21H32O4 Source: Marine-derived fungus Alternaria sp. from sponge Callyspongia sp. (Sanya, Hainan I., China). Pharm: NF-κB inhibitor (RAW264.7 cells, weak to moderate). Ref: G. Zhang, et al, JNP, 2013, 76, 1946 OH

OH O

O

H

392

6 Polyterpenoids and Meroterpenoids

1049 Tricycloalternarene B Type: Other meroterpenoids. C22H34O5 Source: Marine-derived fungus Alternaria sp. from sponge Callyspongia sp. (Sanya, Hainan I., China). Pharm: NF-κB inhibitor (RAW264.7 cells, weak to moderate). Ref: G. Zhang, et al, JNP, 2013, 76, 1946 OH O

O

H

O

H

OH

1050 Tricycloalternarene C Type: Other meroterpenoids. C21H32O4 Source: Marine-derived fungus Alternaria sp. from sponge Callyspongia sp. (Sanya, Hainan I., China). Pharm: NF-κB inhibitor (RAW264.7 cells, weak to moderate). Ref: G. Zhang, et al, JNP, 2013, 76, 1946 OH O

H

O

H

OH

1051 Tropolactone A Type: Other meroterpenoids. C26H34O7 Oil, [α]D = −48° (c = 1.8, CH2Cl2). Source: Marine-derived fungus Aspergillus sp. from an unidentified sponge (Hawaii). Pharm: Cytotoxic (HCT116, IC50 = 13.2 μg/mL). Ref: M. Cueto, et al, Phytochemistry, 2006, 67, 1826 O O O OH O

1

H

O O

H

1052 Tropolactone B Type: Other meroterpenoids. C28H36O8 Oil, [α]D = −30° (c = 0.3, CH2Cl2). Source: Marine-derived fungus Aspergillus sp. from an unidentified sponge (Hawaii). Pharm: Cytotoxic (HCT116, IC50 = 10.9 μg/mL). Ref: M. Cueto, et al, Phytochemistry, 2006, 67, 1826

6.7 Other Meroterpenoids

393

O O O

O O O

1

H

O O

H

1053 Tropolactone C Type: Other meroterpenoids. C26H32O6 Oil, [α]D = −78° (c = 1.1, CH2Cl2). Source: Marine-derived fungus Aspergillus sp. from an unidentified sponge (Hawaii). Pharm: Cytotoxic (HCT116, IC50 = 13.9 μg/mL). Ref: M. Cueto, et al, Phytochemistry, 2006, 67, 1826 O O O

O

1

H

O O

H

1054 Wiedendiol A Type: Other meroterpenoids. C22H32O3 [α]D24 = +122.0° (c = 1, CHCl3), [α]D21 = +121° (CHCl3). Source: Sponge Xestospongia wiedenmayeri (Bahamas). Pharm: Cholesteryl ester transfer protein (CETP) inhibitor (IC50 = 1.0 μmol/L); anti-atherosclerosis. Ref: S. J. Coval, et al, BoMCL, 1995, 5, 605│ S. Chackalamannil, et al, Tet. Lett., 1995, 36, 5315│ A. F. Barrero, et al, Tetrahedron, 1998, 54, 5635│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH HO

O

394

6 Polyterpenoids and Meroterpenoids

1055 Wiedendiol B Sch 50680 Type: Other meroterpenoids. C22H32O3 [α]D21 = −41° (CHCl3). Source: Sponge Xestospongia wiedenmayeri (Bahamas). Pharm: Cholesteryl ester transfer protein (CETP) inhibitor (IC50 = 0.6 μmol/L); cyclooxygenase-2 inhibitor (ten-fold stronger than reference compound indomethacine). Ref: S. J. Coval, et al, BoMCL, 1995, 5, 605│ A. F. Barrero, et al, Tetrahedron, 1998, 54, 5635│ M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH HO

O

H

1056 Xestoquinolide A Type: Other meroterpenoids. C20H16O4 Yellow powder, [α]D = +32°. Source: Sponge Xestospongia cf. carbonaria. Pharm: TPK inhibitor (IC50 = 80 μmol/L). Ref: K. A. Alvi, et al, JOC, 1993, 58, 4871│ D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O

O

O

O

1057 Xestoquinolide B1 Type: Other meroterpenoids. C22H19NO6S Yellow powder. Source: Sponge Xestospongia cf. carbonaria. Pharm: PTK inhibitor. Ref: K. A. Alvi, et al, JOC, 1993, 58, 4871 HN O

S

O

O O

O

O

(One of two possible isomeric structures.)

6.7 Other Meroterpenoids

395

1058 Xestoquinolide B2 Type: Other meroterpenoids. C22H19NO6S Yellow powder. Source: Sponge Xestospongia cf. carbonaria. Pharm: PTK inhibitor. Ref: K. A. Alvi, et al, JOC, 1993, 58, 4871 O O

S

O

NH O

O

O

(One of two possible isomeric structures.)

1059 Yahazunol Type: Other meroterpenoids. C21H32O3 Cryst. (Me2CO/Et2O), mp 127–129 °C, [α]D27 = −12° (c = 0.1, CHCl3). Source: Brown alga Dictyopteris undulata [Syn. Dictyopteris zonarioides]. Pharm: Antimicrobial. Ref: M. Ochi, et al, Bull. Chem. Soc. Jpn., 1979, 52, 629 HO

OH OH H

1060 Zonaquinone acetate Type: Other meroterpenoids. C29H40O4 Source: Brown alga Stypopodium zonale (Jamaica). Pharm: Mildly antiproliferative. Ref: N. Penicooke, et al, Phytochemistry, 2013, 87, 96 O

O

O

H O

H

H

396

6 Polyterpenoids and Meroterpenoids

1061 (+)-Zonarol Type: Other meroterpenoids. C21H30O2 Crystal (Et2O/petroleum ether), mp 173. 5–174.5 °C, [α]D27 = +18° (c = 0.1, CHCl3). Source: Brown alga Dictyopteris undulata [Syn. Dictyopteris Zonaroides]. Pharm: Antifungal. Ref: W. Fenical, et al, JOC, 1973, 38, 2383│ G. Cimino, et al, Experientia, 1975, 31, 1250│ H. Akita, et al, Tetrahedron: Asymmetry, 1998, 9, 1789 HO OH

H

Index 1 Compound Name and Synonym Index This index lists in alphabetical order all active compound’s 1,239 entry names including both 1,061 key names and 178 synonym names contained in the bodies of compound entries. A equal sign ( = ) and compound code number (from 1 to 1,061) follow the name immediately for locating the compound in the “Handbook of Active Marine Natural Products Volume 2” book. Following symbols are ineffective in ordering: D-, L-, dl, R-, S-, E-, Z-, O-, N-, C-, H-, cis-, trans-, ent-, epi-, meso-, erythro-, threo-, sec-, seco-§, m-, o-, p-, n-, α-, β-, γ-, δ-, ε-, κ-, ξ-, ψ-, ω-, (+), (−), (±) etc., and: 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, {, }, [,], (,), ,, ;, , *, ‘, ‘‘, ‘‘‘, →, etc. (§ note: In the books regular “seco-” is effective in ordering as “nor-”.) A Aberrarone = 309. Acalycigorgin A = 119. Acalycigorgin B = 120. Acalycigorgin C = 121. Acalycigorgin D = 122. Acalycigorgin E = 123. Acalycixeniolide A = 161. Acalycixeniolide B = 162. Acalycixeniolide C‡ = 163. Acalycixeniolide D = 164. Acalycixeniolide E = 165. Acalycixeniolide F = 166. Acalycixeniolide H = 124. Acalycixeniolide I = 125. Acalycixeniolide J = 126. Acalycixeniolide K = 167. Acalycixeniolide L = 168. 10-Acetoxyangasiol = 250. 6ʹ-Acetoxyavarol = 824. 25-Acetoxybivittoside D = 619. 4-Acetoxycrenulide = 169. 21-Acetoxydeoxoscalarin = 501. 5-Acetoxy-10,18-dihydroxy-2,7dolabelladiene = 1. 18-Acetoxy-dolabelladiene = 2. 3-Acetoxy-4E,8,18-dolabellatrien-16-al = 3. 16-Acetoxy-7,8-epoxy-3,12(18)-dolabelladien13-one = 4. 6-Acetoxy-7,8-epoxy-3,12-dolabelladien-13one = 5. 12α-Acetoxy-24,25-epoxy-24-hydroxy-20, 24-dimethylscalarane = 546. 12-Acetoxy-16-hydroxy-20,24-dimethyl-24oxo-25-scalaranal = 547. (3α,13Z,16E,20(22)E,23E)-3-Acetoxy-25hydroxy-12,15-dioxo-13,16, 20(22),23isomalabaricatetraen-29-oic acid = 729.

https://doi.org/10.1515/9783110655155-005

18-Acetoxy-10-hydroxy-2,7-dolabelladiene = 6. 12α-Acetoxy-22-hydroxy-24-methyl-24-oxo-16scalaren-25-al = 548. 12-Acetoxy-25-hydroxy-16-scalaren24-al = 518. (Z)-24-Acetoxyneomanoalide = 397. 12α-Acetoxy-17-scalaren-25,24-olide = 506. 4-Acetoxy-thorectidaeolide A = 398. 4-Acetylaplykurodin B = 262. Acetylcoriacenone = 263. 12-O-Acetyl-16-O-deacetyl-16-episcalarobutenolide = 502. 12-O-Acetyl-16-O-deacetyl-12,16-diepiscalarolbutenolide = 503. (Z)-24-Acetyl-2,3-dihydroneomanoalide = 399. Acetylenoxolone = 723. 16-Acetylfuroscalarol = 504. 12-Acetyl-12-epi-heteronemin = 505. Acetylpenasterol = 620. 20-O-Acetylpuupehenone = 825. 12-epi-Acetylscalarolide = 506. Acutilol A = 195. Acutilol A acetate = 196. Acutilol B = 197. Adociasulfate 1 = 826. Adociasulfate 2 = 827. Adociasulfate 3 = 828. Adociasulfate 4 = 829. Adociasulfate 5 = 830. Adociasulfate 6 = 831. Adociasulfate 7 = 832. Adociasulfate 8 = 833. (3S,3ʹR)-Adonixanthin-β-D-glucoside = 785. Aikupikoxide A = 381. Akadisulfate A = 834. Akadisulfate B = 835. Akaterpin = 836. Alotaketal A = 400.

398

Index 1 Compound Name and Synonym Index

Alotaketal C = 567. Amphilectolide = 264. A new drimane sesquiterpene hydroquinone = 837. Ansellone A = 460. Ansellone B (2012) = 568. Antheliatin = 127. Antibiotic Sch 49028 = 280. Antibiotic SQ 16603 = 775. Aplysiadiol = 171. 9ʹ-Apo-fucoxanthinone = 798. APS451275-1 = 837. Arenarol = 838. Arenarone = 839. Arisugacin A = 840. Ascofuranol = 841. Ascofuranone = 842. Ascosalipyrrolidinone A = 843. Asperdemin = 844. Asperterpenoid A = 569. Asperterpenol A = 570. Asperterpenol B = 571. (3S,3′S)-Astaxanthin = 786. (3S,3′S)-Astaxanthin β-D-glucoside = 787. Asterolaurin A = 128. Asterolaurin B = 129. Asterolaurin C = 130. Asterolaurin D = 131. Asterolaurin E = 132. Asterolaurin F = 133. Asterolaurin L = 134. Aureol = 845. Auriculol = 600. Aurilol = 601. Austalide B = 846. Austalide I = 847. Austalide M = 848. Austalide N = 849. Austalide P acid = 850. Austalide R = 851. Austalide U = 852. Avarol = 853. Avarone = 854. Avarone A = 953. Avarone adduct A = 855. Avarone adduct B = 856. Avarone adduct C = 857. Avarone B = 907.

B Barangcadoic acid A = 353. Beauversetin = 858. Bicycloalternarene A = 859. Bicycloalternarene B = 860. Bicycloalternarene C = 861. Bicycloalternarene D = 862. Bielschowskysin = 292. 4,9,15-Bifloratriene = 204. Bifurcarenone = 863. 5,10-Biisothiocyanatokalihinol G = 205. Bilosespene A = 435. Bilosespene B = 436. Bispuupehenone = 864. Bis(sulfato)cyclosiphonodictyol A = 865. Bivittoside D = 621. Blumiolide A = 135. Blumiolide B = 136. Blumiolide C = 137. Bohadschioside A = 621. Bolinaquinone = 866. Brevione A = 253. Brevione B = 254. Brevione E = 255. Brevione F = 256. Brevione G = 257. Brevione H = 258. Brevione I = 259. 14-Bromo-1-obtusene-3,11-diol = 249. Bromophycoic acid A = 265. Bromophycoic acid B = 266. Bromophycoic acid C = 267. Bromophycoic acid D = 268. Bromophycoic acid E = 269. Bromophycolide A = 802. Bromophycolide B = 803. Bromophycolide J = 804. Bromophycolide M = 805. Bromophycolide N = 806. Bromophycolide O = 807. Bromophycolide P = 808. Bromophycolide Q = 809. Bromophycolide R = 810. Bromophycolide S = 811. Bromophycolide T = 812. Bromophycolide U = 813.

Index 1 Compound Name and Synonym Index

C Cacospongienone A = 382. Cacospongienone B = 383. Cacospongionolide B = 572. Cacospongionolide D = 354. Cacospongionolide E = 573. Cacospongionolide F = 574. Calcigeroside B = 622. Calcigeroside C1 = 623. Calcigeroside C2 = 624. Callicladol = 602. Canthaxanthin = 788. Caribenol A = 293. Caribenol B = 294. β,ε-Carotene-3,3′-diol = 795. β,β-Carotene-4,4′-dione = 788. β-Carotene = 789. β,β-Carotene = 789. Catunaroside A = 724. Catunaroside B = 725. Catunaroside C = 726. Catunaroside D = 727. Cavernene A = 206. Cavernene B = 207. Cavernene C = 208. Cavernene D = 209. Cavernosine = 799. Cavernosolide = 461. Cespitularin A = 53. Cespitularin B = 54. Cespitularin C = 55. Cespitularin D = 56. Cespitularin E = 57. Cespitularin F = 58. Cespitularin H = 59. Cespitulin G = 60. Chatancin = 295. Chevalone E = 867. 6ʹ-Chloroaureol = 868. 15-Chloro-14-hydroxyxestoquinone = 310. 14-Chloro-15-hydroxyxestoquinone = 311. 21-Chloropuupehenol = 869. Chromazonarol = 870. ent-Chromazonarol = 871. Chromodorolide B = 296. Chromodorolide C = 297. Cladocoran A = 437. Cladocoran B = 438. Cladoloside B = 625.

Cladoloside B1 = 626. Cladoloside B2 = 627. Cladoloside C = 628. Cladoloside C1 = 629. Cladoloside C2 = 630. Cladoloside D = 631. Claenone = 7. Clavirolide A = 8. Clavirolide B = 9. Clavirolide C = 10. Clavirolide D = 11. Clavirolide E = 12. Clavulactne = 13. (1β,4α,5β,6α,7β)-10(14),17-Cneorubadiene = 203. Colombiasin A = 312. epi-Conicol = 872. Conidiogenol = 313. Conidiogenone B = 314. Conidiogenone C = 315. Conidiogenone D = 316. Conidiogenone E = 317. Conidiogenone F = 318. Conidiogenone G = 319. Conidiogenone H = 320. Conidiogenone I = 321. Conthiaquinone A = 873. Conthiaquinone A methyl ether = 874. Corallidictyal A = 875. Corallidictyal B = 876. Corallidictyal C = 877. Corallidictyal D = 878. Coscinoquinol = 879. Coscinosulfate = 880. Crassumtocopherol A = 881. Crassumtocopherol B = 882. Crellastatin I = 632. Crellastatin J = 633. Crellastatin K = 634. Crellastatin L = 635. Crellastatin M = 636. Cristaxenicin A = 138. Cucumariaxanthin A = 790. Cucumariaxanthin B = 791. Cucumariaxanthin C = 792. Cucumarioside A1 = 637. Cucumarioside A2 = 638. Cucumarioside A3 = 639. Cucumarioside A6-2 = 640.

399

400

Index 1 Compound Name and Synonym Index

Cucumarioside A8 = 641. Cucumarioside A10 = 642. Cucumarioside A13 = 643. Cucumarioside B2 = 644. Cucumarioside H2 = 645. Cucumarioside H3 = 646. Cucumarioside H4 = 647. Cucumarioside H5 = 648. Cucumarioside H6 = 649. Cucumarioside H7 = 650. Cucumarioside H8 = 651. Cucumarioside I1 = 652. 15α-Cyano-19,20-di-Oacetylpuupehenol = 883. 10,17-O-Cyano-4,5-di-epidactylospongiaquinone = 884. 15-Cyanopuupehenol = 885. 15-Cyanopuupehenone = 886. Cyanthiwigin A = 35. Cyanthiwigin B = 36. Cyanthiwigin C = 37. Cyanthiwigin D = 38. Cyanthiwigin E = 39. Cyanthiwigin F = 40. Cyanthiwigin J = 41. Cyanthiwigin U = 42. Cyanthiwigin Z = 43. 2,12-Cyathadiene-1,8-dione = 36. 2,12-Cyathadien-1-one = 35. (12α,16β,25ξ)-23,25-Cyclo-12-Acetoxy-16,25dihydroxy-20,24-dimethyl-24scalaranone = 549. Cycloartane-3,28-disulfate-23-ol = 701. Cycloartane-23-one-3β,28-diol 3,28disulfate = 702. Cycloartane-3β,23ξ,28-triol 3,28disulfate = 703. Cycloart-24-ene-3β,23R-diol 3-Osulfate = 704. Cycloart-24-ene-23-one-3β,28-diol 3,28disulfate = 705. Cycloart-24-ene-3β,23R,28-triol 3sulfate = 706. Cycloart-24-en-23-one-28-sulfate-3-ol = 707. Cyclocymopol = 887. Cyclofurospongin 2 = 384. Cyclolinteinol = 401. Cyclolinteinol acetate = 402. Cyclolinteinone = 403.

Cyclolobatriene = 177. Cyclosiphonodictyol bissulfate A = 865. Cyclospongiacatechol = 888. Cyclozoanthamine = 766. Cystoazorol A = 889. Cystoazorol B = 890. Cystoazorone A = 891. Cystoazorone B = 892. Cystodione A = 893. Cystodione B = 894. Cystodione C = 895. Cystodione D = 896. Cystodione E = 897. Cystodione F = 898. D Dactylomelol = 260. 8-epi-Dactyloquinone = 899. Dactyloquinone B = 900. 12-Deacetoxy-21-acetoxyscalarin = 507. 12-Deacetoxy-12-oxodeoxoscalarin = 520. 12-Deacetoxyscalaradial = 508. 12-Deacetoxyscalarin 19-acetate = 509. 12,16-diepi-12-O-Deacetyl-16-Oacetylfuroscalarol = 510. 12-O-Deacetyl-17-deoxyscalarin = 511. 12-epi-O-Deacetyl-19-deoxyscalarin = 511. 7-Deacetylgedunin = 779. 12-Deacetyl-12,18-diepi-Scalaradial = 512. 16-O-Deacetyl-16-epi-scalarobutenolide = 513. Debromophycolide A = 901. 8,9-Dehydroircinin 1 = 355. 10-epi-Dehydrothyrsiferol = 603. 11α-Dehydroxyisoterreulactone A = 902. Demethylfurospongin 4 = 356. Dendalone = 550. 16-Deoxoisodehydroluffariellolide = 404. Deoxoscalarin = 514. Deoxoscalarin-3-one = 515. 12-epi-Deoxoscalarin-3-one = 516. 25-Deoxycacospongionolide B = 575. 9-Deoxy-7,8-epoxy-isoxeniolide A = 139. 9-Deoxy-7,8-epoxy-xeniolide A = 157. 8-Deoxyxeniolide A = 140. 9-Deoxyxeniolide A = 140. Deoxyxeniolide B = 141. 8-Deoxyxeniolide B = 142. 9-Deoxyxeniolide B = 142. 28-Deoxyzoanthenamine = 767.

Index 1 Compound Name and Synonym Index

22-epi-28-Deoxyzoanthenamine = 768. Desacetoxyscalaradial = 508. 12-Desacetylfuroscalarol = 517. Diacarperoxide S = 576. 10,18-Diacetoxydolabella-2,7E-dien-6one = 14. 2,13-Diacetoxy-3,7,18-dolabellatrien-9one = 15. 19,20-Diacetoxy-7,8-epoxy-3,12,13dolabellatrien = 16. (4S,5S,6S,8S,9S,10R,13R,14S,16S,17Z)-6β,16βdiacetoxy-25-hydroxy-3,7-dioxy-29nordammara-1,17(20)-dien-21-oic acid = 777. 2ʹ,5ʹ-Diacetylavarol = 903. Diapolycopenedioic xylosyl ester A = 800. Dictyoceratin = 905. Dictyoceratin A = 1025. Dictyoceratin B = 904. Dictyoceratin C = 905. Dictyodial = 143. Dictyoepoxide = 144. Dictyolactone = 145. Dictyol C = 198. Dictyol F = 199. Dictyoxepin = 178. 4,5-Di-epi-dactylospongiaquinone = 906. 15,16:17,18-Diepoxy-13-spaten-5-ol = 50. 7,20-Diformamidoisocycloamphilectane = 108. 1,11-Di-3-furanyl-4,8-dimethyl-1,4,8undecatrien-6-ol = 385. 3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyl3,7,11-tridecatrienyl)-2H-1-benzopyran6-ol = 1045. (Z)-2,3-Dihydroneomanoalide = 405. 19-Dihydroscalaradial = 518. 12β,16β,22-Dihydroxy-22-acetoxy-24βmethylscalaran-25,24-olide = 551. 3ʹ,6ʹ-Dihydroxyavarone = 907. 8,11-Dihydroxy-12b-methyl-1H-benzo[6,7] phenanthro[10,1-bc]furan-3,6(2H,12bH)dione = 325. 3,3′-Dihydroxy-β,β-carotene-4,4′-dione = 786. 3β,28-Dihydroxy-cycloart-24-en-23-one 3-Osulfate = 708. 7,8-Dihydroxyeriogorgiaene 8-O-(2-O-acetyl-αL-arabinopyranoside) = 102. 7,8-Dihydroxyeriogorgiaene 8-O-(3-O-acetyl-αL-arabinopyranoside) = 103.

401

7,8-Dihydroxyeriogorgiaene 8-O-(4-O-acetyl-αL-arabinopyranoside) = 104. 7,8-Dihydroxyeriogorgiaene 7-O-(4-O-acetyl-αD-arabinopyranoside) = 241. 7,8-Dihydroxyeriogorgiaene 7-O-(2-O-acetyl-αD-arabinopyranoside) = 242. 7,8-Dihydroxyeriogorgiaene 8-O-α-Larabinopyranoside = 101. 16α,22-Dihydroxy-24-methyl-24-oxo-25,12scalaranolide = 552. 16β,22-Dihydroxy-24-methyl-24-oxo-25,12scalaranolide = 553. 14,15-Dihydroxymethylxestoquinone = 322. 12α,25α-Dihydroxy-16-scalaren-24,25olide = 519. (7β,10E,12E)-7,14-Dihydroxy-1(19),6(20),10,12xenicatetraen-18,17-olide = 136. 5,8-Di-epi-ilimaquinone = 908. 7,20-Diisocyanoadociane = 114. 7,20-Diisocyanoisocycloamphilectane = 114. Dilkamural = 51. Dilophic acid = 146. Dilopholide = 147. Dilophus ether = 52. 2,8-Dimethyl-2-(4,12-dimethyl-8-carboxy-3,11tridecadienyl)-2H-1-benzopyran-6ol = 1013. 3-[4,8-Dimethyl-10-(2,6,6-trimethyl-1cyclohexen-1-yl)-3,7-decadienyl]-2(5H)furanone = 404. Dioxepandehydrothyrsiferol = 604. Dipuupehedione = 909. Distrongylophorine = 910. (1aS,3aS,4E,7S,7aR,10R)-Dodecahydro-4-[(2E)4-hydroxy-4-methylpent-2-en-1-ylidene]1a-methyl-8-methylideneoxireno[5,6] cyclonona[1,2-c]pyran-7,10-diol = 134. (1R*)-Dolabella-4(16),7,11(12)-triene-3,13dione = 17. Dolabella-4(16),7-diene-10,11-epoxy-3,13dione = 18. Dolabella-4(16),10-diene-7,8-epoxy-3,13dione = 19. Dolabellanone 9 = 20. (1R*,12R*)-Dolabella-4(16),7,10-triene-3,13dione = 21. (1α,3E,7E,11α)-3,7,12-Dolabellatrien-18-ol = 30. 3,7,18-Dolabellatrien-9-one = 22. Dolatriol = 33.

402

Index 1 Compound Name and Synonym Index

Dolatriol-6-acetate = 34. Durbinal A = 246. Durbinal B = 247. Durbinal C = 248. (+)-Dysideapalaunic acid = 439. Dysideavarone A = 911. Dysideavarone B = 912. Dysideavarone C = 913. Dysideavarone D = 914. E Echinoside B = 653. Ectyoplaside A = 654. Ectyoplaside B = 655. Elisabanolide = 298. 3-epi-Elisabanolide = 299. Elisabethamine = 210. Elisabethin B = 270. Elisabethin C = 271. Elisabethin D = 300. Elisabethin D acetate = 301. Elisapterosin A = 323. Elisapterosin B = 324. Emmottene = 203. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9acetoxy-10-ol 10-O-(3-O-acetyl-β-Dxylopyranoside) = 94. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9acetoxy-10-ol 10-O-β-Dxylopyranoside = 92. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 10-O-(3-O-acetyl-α-Darabinopyranoside) = 96. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 10-O-(4-O-acetyl-α-Darabinopyranoside) = 97. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 10-O-(4-O-acetyl -α-Lfucopyranoside) = 91. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 9-O-(2-acetyl-α-Lfucopyranoside) = 86. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 9-O-(3-acetyl-α-Lfucopyranoside) = 87. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 9-O-(4-acetyl-α-Lfucopyranoside) = 88.

(1α,3β,7β)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 9-O-(3-acetyl-α-Lfucopyranoside) = 90. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 10-O-(3-O-acetyl-α-Lfucopyranoside) = 93. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 9-O-(2-acetyl-β-Dxylopyranoside) = 80. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene9,10-diol 9-O-(3-acetyl-β-Dxylopyranoside) = 81. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 9-O-(4-acetyl-β-Dxylopyranoside) = 82. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 10-O-α-D-arabino-pyranoside = 84. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 10-O-α-D-arabinopyranoside = 95. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 10-O-(3,4-di-O-acetyl-α-Darabinopyranoside) = 98. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 10-O-(2,4-di-O-acetyl-α-Darabinopyranoside) = 99. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 10-O-α-L-fucopyranoside = 83. (1α,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 9-O-α-L-fucopyranoside = 85. (1α,3β,7β)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 9-O-α-L-fucopyranoside = 89. (1β,3α,7α)-8,10,12,14-Epiamphilectatetraene-9, 10-diol 9-O-β-D-xylopyranoside = 79. 3-Epiaplykurodinone B = 272. Epidictyol F = 200. (24β,25ξ)-16,24-Epoxy-24,25-dihydroxy-17cheilanthen-19,25-olide = 461. (13α,16R,25ξ)-16,24-Epoxy-13,25-dihydroxy-17cheilanthen-19,25-olide = 468. (13α,16S,25ξ)-16,24-Epoxy-13,25-dihydroxy-17cheilanthen-19,25-olide = 469. 24,25-Epoxy-12,25-dihydroxy-16-scalaren-3one = 535. 3,4-Epoxy-7,18-dolabelladiene = 23. 7,8-Epoxy-3,18-dolabelladiene = 24. (3R,4R,7E)-3,4-Epoxy-7,12(18)-dolabelladien13-one = 7.

Index 1 Compound Name and Synonym Index

7,8-Epoxy-3,12-dolabelladien-14-one = 25. Epoxyfocardin = 273. (3β,12α,20R,22R)-22,25-Epoxyholost-9(11)-ene3,12-diol 3-O-[6-deoxy-β-D-glucopyranosyl(1→2)-β-D-xylopyranoside] = 670. (3β,12α,20R,22R)-22,25-Epoxyholost-9(11)-ene3,12-diol 3-O-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)-βD-xylopyranoside] = 669. 13,16-Epoxy-25-hydroxy-17-cheilanthen-19,25olide = 462. (13α,16R,25ξ)-13,16-Epoxy-25-hydroxy-17cheilanthen-19,25-olide = 467. 3,4-Epoxy-14-hydroxy-7,18dolabelladiene = 26. 24,25-Epoxy-25-hydroxy-16-scalaren-12one = 520. 13ξ,15ξ-Epoxy (isomer 1)-8,10,13(15),16lobatetraen-18-ol O-β-Darabinopyranose = 186. 13ξ,15ξ-Epoxy (isomer 2)-8,10,13(15),16lobatetraen-18-ol O-β-Darabinopyranose = 187. 17R,18-Epoxy-8,10,13(15)-lobatriene = 179. 14,18-Epoxyloba-8,10,13(15)-trien-17-ol = 180. 14,17-Epoxy-8,10,13(15)-lobatrien-18-ol = 190. 14,17-Epoxyloba-8,10,13(15)-trien-18-ol acetate = 181. 9,11-Epoxy-17-loben-3-ol = 178. 5,21-Epoxy-7,16,18-ophiobolatriene-3,5diol = 495. 3,4-Epoxy-14-oxo-7,18-dolabelladiene = 27. (5β,6β,11R,14ξ)-14,15-Epoxy-1(10),3pachydictyadien-6-ol = 195. Epoxyphomalin D = 915. 24,25-Epoxy-16-scalarene-12,19-diacetoxy-25ol = 501. 24,25-Epoxy-16-scalarene-12β,25α-diol = 521. (3β,12α,25α)-24,25-Epoxy-16-scalarene-3,12, 25-triol = 522. (6α,7β,10E,12E)-6,7-Epoxy-1(19),10,12xenicatrien-18,17-olide = 149. 7,8-Epoxyzahavin A = 148. 6,7-Epoxyzahavin A = 148. Erogorgiaene = 244. Eryloside F = 656. Eryloside F1 = 657. Eryloside G = 658.

403

Eryloside H = 659. Eryloside I = 660. Eryloside J = 661. Erythrolic acid D = 916. Ethyl plumarellate = 302. Eunicidiol = 182. Eunicol = 172. Euplexide A = 917. Euplexide B = 918. Euplexide C = 919. Euplexide D = 920. Euplexide E = 921. Euplexide F = 922. Euplexide G = 923. Expansol A = 924. Expansol B = 925. F Faraunatin = 175. Farnesylhydroquinone = 926. Fasciculatin = 357. Fasciculatin O-sulfate = 358. Fasciospongide A = 406. Fasciospongide B = 359. Fasciospongide C = 360. Fasciquinol A = 927. Fasciquinol B = 928. Flabelliferin A = 577. Flabelliferin B = 578. Florlide B = 170. Florlide D = 149. Focardin = 274. Foliaspongin = 554. (1R*)-7-Formamido-11(20),14amphilectadiene = 62. (1S*)-7-Formamido-11(20),15amphilectadiene = 63. 7-Formamido-11(20)-cycloamphilectene = 109. 10-Formamido-5-isocyanatokalihinol A = 211. 7-Formamido-20isocyanoisocycloamphilectane = 115. 10-Formamido-5-isothiocyanatokalihinol A = 212. 15-Formamidokalihinene = 213. 10-Formamidokalihinene = 214. 10-Formamidokalihinol A = 215. 10-Formamidokalihinol E = 216. Formoside B = 662. Frondoside A = 663.

404

Index 1 Compound Name and Synonym Index

Frondoside C = 664. Frondosin A = 929. (–)-Frondosin A = 930. Frondosin B = 931. Frondosin C = 932. (+)-Frondosin D = 933. (–)-Frondosin D = 934. Frondosin E = 935. Fucoxanthin = 793. Fucoxanthinol = 794. Fucoxanthol = 793. Fukurinolal = 150. Fumigacin = 776. 5-[13-(3-Furanyl)-2,6,10-trimethyl-3,5tridecadienyl]-4-hydroxy-3-methyl-2(5H)furanone = 361. Furoscalarol = 523. Furospinulosin 1 = 362. Furospongin 2 = 386. Furospongin 5 = 363. Furospongolide = 387. Fuscol = 183. Fuscol methyl ether = 184. Fuscoside A = 275. Fuscoside B = 185. Fuscoside C = 186. Fuscoside D = 187. Fuscoside E = 276. Fusidic acid = 775. Fusidin = 775. G Glaciapyrrole A = 936. Globostellatic acid A = 729. Globostellatic acid B = 730. Globostellatic acid C = 731. Globostellatic acid D = 732. Globostelletin A = 733. Globostelletin B = 734. Globostelletin C = 735. Globostelletin D = 736. Globostelletin E = 737. Globostelletin F = 738. Globostelletin G = 739. Globostelletin H = 740. Globostelletin I = 741. Glycyrrhetic acetate = 723. Godavarin A = 714. Godavarin D = 715.

Guignardone B = 937. Guignardone I = 938. Gukulenin A = 44. Gukulenin C = 45. Gukulenin D = 46. Gukulenin E = 47. Gukulenin F = 48. H Halenaquinol = 325. Halenaquinol O16-Sulfate = 326. Halenaquinone = 327. Halicloic acid A = 939. Halicloic acid B = 940. Halimedalactone = 277. Halimedatrial = 278. Halioxepine = 941. Halisulfate 7 = 440. Halisulfate 9 = 441. Halisulfate 1 = 942. Halitunal = 261. Halorosellinic acid = 490. Hamigeran E = 943. Hamiltonin E = 463. Helioporin A = 64. Helioporin B = 65. Helioporin C = 66. Helioporin D = 67. Helioporin E = 68. Helioporin F = 69. Helioporin G = 70. Helvolic acid = 776. Hemoiedemoside A = 665. Hemoiedemoside B = 666. 2-Heptaprenyl-1,4-benzenediol-4sulfate = 944. Heptaprenylhydroquinone = 945. Heteronemin = 524. 12-epi-Heteronemin = 525. 2,6,10,15,19,23-Hexamethyl-1,5,14,18,22tetracosapentaen-4-ol = 608. 2-Hexaprenyl-1,4-benzenediol = 946. Hexaprenylhydroquinone = 946. 2-(Hexaprenylmethyl)-2-methyl-2H-1benzopyran-6-ol = 1012. Hippospongic acid A = 605. Hippospongide A = 579. Hippospongide B = 580. Hippospongide C = 526.

Index 1 Compound Name and Synonym Index

Hippospongin = 407. Hipposulfate A = 947. (3β,16β)-Holosta-7,24-diene-16-acetoxy-3-ol 3O-[3-O-methyl-6-O-sulfo-β-Dglucopyranosyl-(1→3)-6-O-sulfo-β-Dglucopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-4-O-sulfo-β-Dxylopyranoside] = 682. (3β,12α)-Holosta-9(11),24-diene-3,12-diol 3-O[3-O-methyl-β-D-glucopyranosyl-(1→3)-βD-glucopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)]-β-D-xylopyranoside] = 680. (3β,12α)-Holosta-9(11),25-diene-3,12-diol 3-O[3-O-methyl-β-D-glucopyranosyl-(1→3)-βD-glucopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)]-β-D-xylopyranoside] = 684. (3β)-Holosta-7,25-diene-3-ol-16-one 3-O-[3-Omethyl-β-D-glucopyranosyl-(1→3)-6-Osulfo-β-D-glucopyranosyl-(1→4)-[β-Dxylopyranosyl-(1→2)]-6-deoxy-β-Dglucopyranosyl-(1→2)-4-O-sulfo-β-Dxylopyranoside] = 639. (3β)-Holosta-7,25-diene-3-ol-16-one 3-O-[3-Omethyl-6-O-sulfo-β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl-(1→4)-[β-Dxylopyranosyl-(1→2)]-6-deoxy-β-Dglucopyranosyl-(1→2)-4-O-sulfo-β-Dxylopyranoside] = 640. (3β,12α,17αOH,20S)-Holost-9(11),24-diene3,12,17-triol 3-O-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)[3-O-methyl-β-D-glucopyranosyl-(1→3)-βD-glucopyranosyl-(1→4)]-β-Dxylopyranoside] = 679. (3β,12α)-Holost-9(11),23-diene-3,12,25-triol 3-O[3-O-methyl-β-D-glucopyranosyl-(1→3)-βD-glucopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)]-β-D-xylopyranoside] = 685. (3β,12α)-Holost-9(11)-ene-25-acetoxy-3,12-diol 3-O-[3-O-methyl-β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl-(1→4)-6-deoxyβ-D-glucopyranosyl-(1→2)-[3-O-methyl-β-

405

D-glucopyranosyl-(1→3)-β-Dglucopyranosyl-(1→4)]-β-Dxylopyranoside] = 619. (3β,9β,16β)-Holost-7-ene-16-acetoxy-3-ol 3-O-[3O-methyl-β-D-glucopyranosyl-(1→3)-β-Dxylopyranosyl-(1→4)-[β-D-xylopyranosyl(1→2)]-6-deoxy-β-D-glucopyranosyl-(1→2)-4O-sulfo-β-D-xylopyranoside] = 663. (3β,9α,16β)-Holost-7-ene-16-acetoxy-3-ol 3-O-[3O-methyl-6-O-sulfo-β-D-glucopyranosyl(1→3)-6-O-sulfo-β-D-glucopyranosyl-(1→4)6-deoxy-β-D-glucopyranosyl-(1→2)-4-Osulfo-β-D-xylopyranoside] = 683. (3β,12α)-Holost-9(11)-ene-3,12-diol 3-O-[3-Omethyl-β-D-glucopyranosyl-(1→3)-β-Dglucopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)]-β-D-xylopyranoside = 621. (3β,12α,17α,24ξ)-Holost-9(11)-ene-3,12,17,24tetrol 3-O-[6-deoxy-β-D-glucopyranosyl(1→2)-4-O-sulfo-β-Dxylopyranoside] = 681. (3β,12α,17αOH,20S)-Holost-9(11)-ene-3,12,17triol 3-O-[6-deoxy-β-D-glucopyranosyl(1→2)-4-O-sulfo-β-Dxylopyranoside] = 653. Holothurigenol 3-O-[6-deoxy-β-Dglucopyranosyl-(1→2)-4-O-sulfo-β-Dxylopyranoside] = 667. Holothurigenol 3-O-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)[β-D-glucopyranosyl-(1→4)]-β-Dxylopyranoside] = 668. Holothurin B = 667. Holothurinoside A = 668. Holothurinoside C = 669. Holothurinoside D = 670. Holotoxin A = 671. Holotoxin A1 = 672. Holotoxin B = 673. Holotoxin D = 674. Holotoxin D1 = 675. Holotoxin E = 676. Holotoxin F = 677. Holotoxin G = 678. Homoplakotenin = 948. Homoplakotenin sodium salt = 949.

406

Index 1 Compound Name and Synonym Index

Homopseudopteroxazole = 71. (–)-Hyatellaquinone = 950. (+)-Hyatellaquinone = 951. 7-Hydroperoxydolabella-4(16),8(17),11(12)triene-3,13-dione = 28. 7-Hydroperoxy-3,8,12-dolabellatrien-14one = 20. 16β-Hydroxy-22-acetoxy-24-methyl-24-oxo -25,12-scalaranolide = 555. 12β-Hydroxy-22-acetoxy-24-methyl-24-oxo-16scalaren-25-al = 556. Hydroxyacetyldictyolal = 150. 6ʹ-Hydroxyavarol = 952. 3ʹ-Hydroxyavarone = 953. 25-Hydroxy-13(24),17-cheilanthadien-16,19olide = 464. 25-Hydroxy-13(24),15,17-cheilanthatrien-19,25olide = 465. 12-Hydroxy-2,13-cyathadien-1-one = 42. 3β-Hydroxycycloart-24-en-23-one 3sulfate = 709. 16-epi-Hydroxydehydrothyrsiferol = 606. 21-Hydroxydeoxoscalarin = 527. Hydroxydictyodial = 151. 25-Hydroxy-24,25-Dihydrohelvolic acid = 777. (3β,5α)-3-Hydroxy-4,4-dimethylcholesta-8,24dien-23-one 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl-(1→6)-2acetamido-2-deoxy-β-D-glucopyranosyl(1→2)-[2-acetamido-2-deoxy-β-Dgalactopyranosyl-(1→4)]-β-Dxylopyranoside] = 696. (3β,5α)-3-Hydroxy-4,4-dimethylcholesta-8,24dien-23-one 3-O-[β-D-glucopyranosyl(1→2)-β-D-xylopyranosyl-(1→6)-2acetamido-2-deoxy-β-D-glucopyranosyl(1→2)-[2-acetamido-2-deoxy-β-Dgalactopyranosyl-(1→4)]-β-Dxylopyranoside] = 697. 3-Hydroxy-4,6-dimethyl-6-(2-methyl-10-phenyl9-decenyl)-1,2-dioxan-3-acetic acid = 408. 3-Hydroxy-4,6-dimethyl-6-(2-methyl-10phenyldecyl)-1,2-dioxan-3-acetic acid = 409. (1R*,3R*)-3-Hydroxydolabella-4(16),7,11(12)triene-3,13-dione = 29. 2α-Hydroxyelisabethin A = 300. 2-Hydroxyfissinolide = 716.

25-Hydroxyhalisulfate 9 = 442. 5ʹ-Hydroxy-2-heptaprenyl-1,4benzenediol = 954. 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3O-methyl-β-D-glucopyranosyl-(1→3)-β-Dglucopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-D-glucopyranosyl(1→4)]-β-D-xylopyranoside] = 671. 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3O-methyl-β-D-glucopyranosyl-(1→3)-β-Dglucopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl-(1→4)]-β-Dxylopyranoside] = 673. 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3O-methyl-β-D-glucopyranosyl-(1→3)-6-Osulfo-β-D-glucopyranosyl-(1→4)-6-deoxy-βD-glucopyranosyl-(1→2)-4-O-sulfo-β-Dxylopyranoside] = 665. 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3O-methyl-β-D-glucopyranosyl-(1→3)-β-Dxylopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[β-D-glucopyranosyl(1→4)]-β-D-xylopyranoside] = 625. 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O[3-O-methyl-β-D-glucopyranosyl-(1→3)-βD-xylopyranosyl-(1→4)-6-deoxy-β-Dglucopyranosyl-(1→2)-[3-O-methyl-β-Dglucopyranosyl-(1→3)-β-Dglucopyranosyl-(1→4)]-β-Dxylopyranoside] = 672. 3β-Hydroxyholosta-9(11),25-dien-16-one 3-O-[3O-methyl-6-O-sulfo-β-D-glucopyranosyl(1→3)-6-O-sulfo-β-D-glucopyranosyl(1→4)-6-deoxy-β-D-glucopyranosyl-(1→2)4-O-sulfo-β-D-xylopyranoside] = 666. 3β-Hydroxyholost-7-en-23-one 3-O-[3-O-methylβ-D-xylopyranosyl-(1→3)-β-Dglucopyranosyl-(1→4)-[β-D-glucopyranosyl(1→2)]-6-deoxy-β-D-glucopyranosyl-(1→2)-4O-sulfo-β-D-xylopyranoside] = 624. 17α-Hydroxyimpatienside A = 679. 6-Hydroxykalihinene = 217. 3-Hydroxylanosta-8,24-dien-30-oic acid 3-O-[2acetamido-2-deoxy-β-D-galactopyranosyl(1→2)-[β-D-galactopyranosyl-(1→3)-α-Larabinopyranosyl-(1→3)]-α-Larabinopyranoside] = 662.

Index 1 Compound Name and Synonym Index

3β-Hydroxylanosta-8,24-dien-30-oic acid 3-O[β-D-galactopyranosyl-(1→2)-α-Larabinopyranoside] = 656. 18-Hydroxy-8,10,13(15)-lobatrien-14,17olide = 194. 3-Hydroxy-5-megastigmene-7,9-dione = 801. 3-Hydroxy-24-methylenelanost-8-en-30-oic acid 3-O-[2-acetamido-2-deoxy-β-Dglucopyranosyl-(1→2)-[α-Larabinopyranosyl-(1→3)]-β-D-galactopyranoside] = 658. 12α-O-(3-Hydroxy-4-methylpentanoyl)-16αhydroxy-20,24-dimethyl-25-nor-17scalaren-24-one = 557. 15-Hydroxymethylxestoquinone = 328. 14-Hydroxymethylxestoquinone = 329. 6R-Hydroxymexicanolide = 717. 25ʹ-Hydroxy-2-octaprenyl-1,4-benzenediol-4sulfate = 955. (3E,10β,11β)-11-Hydroxy-6-oxo-3,12(18)dolabelladien-19,10-olide = 8. 3-Hydroxy-5-oxo-7,16,18-ophiobolatrien-21al = 496. (5β,6β,11R)-6-Hydroxy-1(10),3pachydictyadien-14-one = 197. 12α-O-(3-Hydroxypentanoyloxy)-16α-ethoxy-24βhydroxy-20,24-dimethyl-17-scalaren-25,24olide = 558. 12α-O-(3-Hydroxypentanoyloxy)-16α-ethoxy-24αhydroxy-20,24-dimethyl-17-scalaren-25,24olide = 559. 19-Hydroxypolyfibrospongol B = 956. 9ʹ-Hydroxysarquinone = 957. 29-Hydroxystelliferin A = 742. 29-Hydroxystelliferin E = 743. 3-epi-29-Hydroxystelliferin E = 744. 3-Hydroxy-3,4,6-trimethyl-6-(2-methyl-10phenyl-9-decenyl)-1,2dioxane = 410. 3-Hydroxy-3,4,6-trimethyl-6-(2-methyl-10phenyldecyl)-1,2-dioxane = 411. 3β-Hydroxy-12-ursen-28-oic acid = 781. 4-Hydroxy-1(9),6,13-xenicatriene-18,19dial = 151. 2-Hydroxyxylorumphiin F = 718. 26-Hydroxyzoanthamine = 769. 26-Hydroxy-19-epi-zoanthamine = 770. Hypoxysordarin = 330. Hyrtial = 528.

407

Hyrtiolide = 529. (–)-Hyrtiosal = 581. Hyrtiosin E = 530. I (–)-Idiadione = 364. Impatienside A = 680. Ineleganene = 188. Inorolide A = 582. Inorolide B = 583. Inorolide C = 466. Irciformonin I = 388. Ircinianin lactam A = 584. (S)-Ircinin 1 = 365. (R)-Ircinin 1 = 366. (S)-Ircinin 1 O-sulfate = 367. (S)-Ircinin 1 O-sulfate Δ11-isomer = 368. Ircinin 2 = 369. Ircinolide A = 470. Ircinolide B = 471. Ircinol sulfate = 958. Isoacetylcoriacenone = 279. Isoavarol = 981. 7-Isocyano-10,14-amphilectadiene = 72. 7-Isocyanoamphilecta-11(20),15-diene = 73. 7-Isocyano-11,14-epi-amphilectadiene = 74. 7-Isocyano-11(20),14-epiamphilectadiene = 75. 7-Isocyano-11-cycloamphilectene = 110. 7-Isocyano-10-cycloamphilectene = 111. (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20Isocyano-7isocyanatoisocycloamphilectane. = 116. (1S*,3S*,4R*,7S,8S*,11R*,12R*,13S*,20S*)-7Isocyanoisocycloamphilect-14-ene = 117. 7-Isocyano-15-isothiocyanato-11(20)amphilectene = 76. (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20Isocyano-7isothiocyanatoisocycloamphilectane = 112. 7-Isocyano-1(14),15-neoamphilectadiene = 77. (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20Isocyanato-7isocyanoisocycloamphilectane = 118. Isodehydroluffariellolide = 412. Isodehydrothyrsiferol = 607. Isofasciculatin = 370. Isojaspic acid = 959. Isometachromin = 960.

408

Index 1 Compound Name and Synonym Index

Isopachydictyol A = 201. Isopalinurin = 371. Isophorbasone A = 585. Isospongiaquinone = 961. 5-epi-Isospongiaquinone = 962. 7-Isothiocyanato-11(20),14-epi-amphilectadien12-ol = 78. 10-Isothiocyanatobiflora-4,15-diene = 218. 10-Isothiocyanatokalihinol C = 219. Isozonarol = 963. J Jaspiferal A = 745. Jaspiferal B = 746. Jaspiferal C = 747. Jaspiferal D = 748. Jaspiferal E = 749. Jaspiferal F = 750. Jaspiferal G = 751. Jaspolide F = 752. JBIR 65 = 303. K Kalihinene = 220. Kalihinene E = 221. Kalihinene F = 222. Kalihinene X = 223. Kalihinene Y = 224. Kalihinene Z = 225. Kalihinol A = 226. Kalihinol D = 227. Kalihinol E = 228. Kalihinol F = 229. 10-epi-kalihinol I = 230. Kalihinol J = 231. Kalihinol X = 232. 10-epi-Kalihinol X = 233. Kalihinol Y = 234. Δ9-Kalihinol Y = 235. Kalihipyran A = 236. Kalihipyran B = 237. Kalihipyran C = 238. Kohamaic acid A = 443. Kohamaic acid B = 444. L (3β,20R,22R)-Lanosta-9(11),24-diene-22-acetoxy3,20-diol 3-O-[3-O-methyl-6-O-sulfo-β-Dglucopyranosyl-(1→3)-6-O-sulfo-β-D-

glucopyranosyl-(1→4)-[β-D-xylopyranosyl(1→2)]-6-deoxy-β-D-glucopyranosyl(1→2)-4-O-sulfo-β-Dxylopyranoside] = 664. Lemnabourside B = 239. Lemnabourside C = 240. Leucospilotaside B = 681. Limatulone = 782. meso-Limatulone = 782. Lintenolide A = 486. Lintenolide B = 487. Lintenolide C = 467. Lintenolide D = 468. Lintenolide E = 469. 13E-Lintenone = 586. 13Z-Lintenone = 587. Liouvilloside A = 682. Liouvilloside B = 683. Liphagal = 964. (1R*,2R*,4S*,15E)-Loba-8,10,13(14),15(16)tetraen-17,18-diol-17-acetate = 189. 8,10,13(15)E,18-Lobatetraene = 188. 8,10,13(15),16-Lobatetraen-18-ol = 183. Lobatriene = 190. Loba-8,10,13(15)-triene-17-acetoxy-18-ol = 191. (17R)-Loba-8,10,13(15)-triene-17,18-diol = 192. Loba-8,10,13(15)-triene-16,17,18-triol = 193. 8,10,13(15)-Lobatriene-16,17,18-triol = 193. Lobatrienolide = 194. Lobocompactol A = 173. Lobocompactol B = 174. Lobophytene = 608. Lovenone = 778. Luffalactone = 445. Luffariellin A = 588. Luffariellin B = 589. Luffariellolide = 413. Luffarin A = 446. Luffarin C = 447. Luffarin D = 448. Luffarin K = 449. Luffarin L = 450. Luffarin Q = 372. Luffariolide A = 414. Luffariolide B = 415. Luffariolide C = 416. Luffariolide D = 417. Luffariolide E = 418. Lutein = 795.

Index 1 Compound Name and Synonym Index

M Magireol A = 609. Magireol B = 610. Magireol C = 611. Makassaric acid = 965. (+)-Makassaric acid = 965. Mamanuthaquinone = 966. Manoalide = 419. Marine derived tocopherol = 1044. Marmoratoside A = 684. Marmoratoside B = 685. Martiriol = 612. Melemeleone B = 967. Menzoquinone = 968. Merochlorin A = 590. Merochlorin B = 591. Meroterphenol A = 969. Meroterphenol B = 970. Meroterphenol C = 971. Meroterphenol D = 972. Metachromin A = 814. Metachromin C = 815. Metachromin D = 816. Metachromin E = 817. Metachromin F = 818. Metachromin G = 819. Metachromin H = 820. Metachromin U = 821. Metachromin V = 822. Metachromin W = 823. 5′-Methoxy-(2E)-bifurcarenone = 973. 14-Methoxyhalenaquinone = 331. Methoxyhalenaquinone = 331. 3β-Methoxyolean-18-ene = 728. 15-Methoxypuupehenol = 974. 3-Methoxy-5-(3,7,11,15-tetramethyl-2,6,10,14hexadecatetraenyl)-1,2benzenediol = 975. 15-Methoxyxestoquinone = 332. 14-Methoxyxestoquinone = 333. 2-Methyl-2-butenyl-geranylgeranylgeranylhydroquinone = 945. 15α-Methyl-19,20-di-O-acetylpuupehenol = 976. Methyl 3β,23R-dihydroxycycloart-24-en-28-oate 3-sulfate = 710. Methyl 3β,23R-dihydroxy-29-nor-cycloart-24en-28-oate 3-sulfate = 711. Methyl 3β,23R-dihydroxy-29-nor-lanosta-8,24dien-28-oate 3-sulfate = 686.

409

24-Methyl-24,25-dioxoscalar-16-en-12β-yl-3hydroxy-butanoate = 550. Methyl 3β-hydroxy-23-oxocycloart-24-en-28oate 3-sulfate = 712. Methyl 3β-Hydroxy-23-oxo-29-nor-cycloart-24en-28-oate 3-sulfate = 713. Methyl 3β-hydroxy-23-oxo-29-nor-lanosta-8,24dien-28-oate 3-sulfate = 687. 24-Methyl-25-nor-12,24-dioxo-16-scalaren-22oic acid = 531. 2-Methyl-2-(pentaprenylmethyl)-2H-1benzopyran-6-ol = 1011. 15α-Methylpuupehenol = 977. 2-Methyl-2-(tetraprenylmethyl)-2H-1benzopyran-6-ol = 978. 24-Methyl-12,24,25-trioxo-16-scalaren-22-oic acid = 560. Miliacin = 728. Molokinenone = 979. Moluccensin R = 719. Moluccensin S = 720. Moritoside = 980. epi-Muqubilin A = 420. 13R,16R,17R-Muqubilin A. = 420. 13R,16S,17R-Muqubilin A = 421. 13S,16R,17S-Muqubilin A = 422. Muqubilin B = 423. ent-Muqubilin = 421. Muqubilone = 381. ent-(–)-Muqubilone = 389. (+)-Muqubilone B = 390. Mycaperoxide A = 451. Mycaperoxide B = 452. Myrocin D = 304. Myxol = 796. N Nanolobatolide = 305. Neoavarol = 981. Neoavarone = 982. Neomangicol A = 592. Neomangicol B = 593. (6E)-Neomanoalid-24-al = 424. (6Z)-Neomanoalide = 425. (6E)-Neomanoalide = 426. Neopetrosiquinone A = 983. Neopetrosiquinone B = 984. 15α-Nitroethyl-19,20-di-Oacetylpuupehenol = 985.

410

Index 1 Compound Name and Synonym Index

15α-Nitromethyl-19,20-di-Oacetylpuupehenol = 986. Nonaprenylhydroquinone = 987. Nonaprenylhydroquinone sulfate = 988. 26-Nor-25-oxo-holotoxin A1 = 688. Norscalaral A = 532. Norscalaral B = 533. Norscalaral C = 534. Noscomin = 989. Novaxenicin B = 152. O Octaprenylhydroquinone = 990. Okinonellin B = 373. Ophiobalin = 491. Ophiobolin A = 491. Ophiobolin C = 492. Ophiobolin G = 493. 6-epi-Ophiobolin G = 494. Ophiobolin H = 495. Ophiobolin K = 496. 6-epi-Ophiobolin N = 497. Ophiobolin O = 498. 6-epi-Ophiobolin O = 499. Ophiobolin U = 500. 6-Oxo-4(16),12(18)-dolabelladien-19,10olide = 12. 5-Oxo-3,7,16,18-ophiobolatetraen-21-al = 493. 15-Oxopuupehenol = 991. Oxyzoanthamine = 769. epi-Oxyzoanthamine = 770. P (1α,5β,6β,11R,14R)-3,10(18),15Pachydictyatriene-6,14-diol = 199. Pachydictyol A = 202. Paclitaxel = 61. Palauolide = 453. Palauolol = 454. Palinurin = 374. Palmatol = 176. Palominol = 30. Patagonicoside A = 689. Patagonicoside B = 690. Patagonicoside C = 691. Penasterone = 692. Penicillipyrone B = 992. Penicilliumin A = 993. Pentactaside I = 693.

Pentactaside II = 694. Pentactaside III = 695. 2-Pentaprenyl-1,4-benzenediol-4sulfate = 994. Petrosaspongiolide A = 470. Petrosaspongiolide B = 471. Petrosaspongiolide C = 472. Petrosaspongiolide D = 473. Petrosaspongiolide E = 474. Petrosaspongiolide F = 475. Petrosaspongiolide H = 476. Petrosaspongiolide I = 477. Petrosaspongiolide J = 478. Petrosaspongiolide K = 594. Petrosaspongiolide M = 479. Petrosaspongiolide N = 480. Petrosaspongiolide P = 481. Petrosaspongiolide Q = 482. Petrosaspongiolide R = 483. Peyssonol A = 995. Peyssonol B = 996. Phomactin A = 280. Phomactin B = 281. Phomactin B1 = 282. Phomactin B2 = 283. Phomactin C = 284. Phomactin D = 285. Phomactin E = 286. Phomactin F = 287. Phomactin G = 288. Phorbaketal A = 427. Phorbaketal B = 428. Phorbaketal C = 429. Phorbaketal H = 430. Phorbaketal I = 431. Phorbasone A = 595. Phorbasone A acetate = 596. Phorone A = 597. Phyllofenone D = 561. Phyllolactone A = 562. Phyllolactone B = 563. Phyllolactone C = 564. Phyllolactone D = 565. Phyllolactone E = 566. Plakopolyprenoside = 797. Plakotenin = 997. Plumarellide = 306. Plumisclerin A = 307. Polyfibrospongol A = 998.

Index 1 Compound Name and Synonym Index

Polyfibrospongol B = 999. Posietogenin 3-O-[3-O-methyl-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl-(1→4)-[6-deoxy-βD-glucopyranosyl-(1→2)]-6-deoxy-β-Dglucopyranosyl-(1→2)-4-O-sulfato-β-Dxylopyranoside] = 622. Posietogenin 3-O-[3-O-methyl-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl-(1→4)-[β-Dglucopyranosyl-(1→2)]-6-deoxy-β-Dglucopyranosyl-(1→2)-4-O-sulfato-β-Dxylopyranoside] = 623. (–)-Prehalenaquinone = 334. Prianicin B = 456. Pseudoalteromone A = 1000. Pseudodehydrothyrsiferol = 613. Pseudopterosin A = 79. Pseudopterosin B = 80. Pseudopterosin C = 81. Pseudopterosin D = 82. Pseudopterosin E = 83. Pseudopterosin F = 84. Pseudopterosin G = 85. Pseudopterosin H = 86. Pseudopterosin I = 87. Pseudopterosin J = 88. Pseudopterosin K = 89. Pseudopterosin L = 90. Pseudopterosin P = 91. Pseudopterosin P1aA = 91. Pseudopterosin P1bD = 92. Pseudopterosin Q = 93. Pseudopterosin Q‡ = 94. Pseudopterosin Q1a3 = 93. Pseudopterosin Q1a4 = 91. Pseudopterosin Q1b3 = 94. Pseudopterosin R1a1 = 93. Pseudopterosin T1aA = 95. Pseudopterosin U = 97. Pseudopterosin U1a3 = 96. Pseudopterosin U1a4 = 97. Pseudopterosin V = 96. Pseudopterosin V1a3 = 96. Pseudopterosin V1a4 = 97. Pseudopterosin W = 98. Pseudopterosin X = 99. Pseudopterosin Y = 95. Pseudopteroxazole = 100. Puupehedione = 1001.

(–)-Puupehenone = 1002. (+)-Puupehenone = 1003. R Raspacionin = 760. (–)-Reiswigin A = 251. Reiswigin B = 252. Renierin B = 1004. Rhabdastrellic acid A = 753. Rhopaloic acid A = 391. Rhopaloic acid B = 392. Rhopaloic acid C = 393. Rietone = 1005. Rossinone A = 1006. Rossinone B = 1007. S Sacrohydroquinone sulfate A = 1008. Sacrohydroquinone sulfate B = 1009. Sacrohydroquinone sulfate C = 1010. Salmahyrtisol C = 535. Sarasinoside A1 = 696. Sarasinoside B1 = 697. Sarcochromenol A = 1011. Sarcochromenol B = 1012. Sarcophytin = 308. Sarcotin A = 375. Sarcotin B = 376. Sarcotin C = 377. Sarcotin D = 378. Sarcotin E = 379. Sargachromenol = 1013. Sargadiol I = 1014. Sargadiol II = 1015. Sargaol = 1016. Sargasal I = 1017. Sargasal II = 1018. Scabellone B = 1019. Scalaradial = 536. 12-epi-Scalaradial = 537. 18-epi-Scalaradial = 538. Scalarafuran = 539. 16-epi-Scalarolbutenolide = 540. Sch 50678 = 1029. Sch 50680 = 1055. Secoadociaquinone A = 335. Secoadociaquinone B = 336. Secomanoalide = 432.

411

412

Index 1 Compound Name and Synonym Index

Seco-pseudopterosin A = 101. Seco-pseudopterosin B = 102. Seco-pseudopterosin C = 103. Seco-pseudopterosin D = 104. Secopseudopterosin H = 241. Secopseudopterosin I = 242. Secopseudopteroxazole = 243. (1α,4αH)-14-Serrulatene = 244. 14-Serrulaten-7-ol = 245. Sesterstatin 1 = 541. Sesterstatin 2 = 542. Sesterstatin 3 = 543. Sexangulic acid = 698. Shaagrockol B = 1020. Shaagrockol C = 1021. Sigmosceptrellin A = 455. Sigmosceptrellin B = 456. Sigmosceptrellin C = 457. Similan A = 544. Sinulobatin A = 105. Sinulobatin B = 106. Sinulobatin C = 107. Sinulobatin D = 113. Sinutriangulin A = 289. Siphonodictyal C = 1022. Siphonodictyal sulfate = 1023. Smenorthoquinone = 1024. Smenospondiol = 1025. Sodwanone A = 761. Sodwanone G = 762. Sodwanone H = 763. Sodwanone I = 764. Sodwanone M = 765. 13,16-Spatadiene-5,15,18,19-tetrol = 49. (+)-Spatol = 50. 3,17-Sphenolobadiene-5,16-dione = 252. 3-Sphenolobene-5,16-dione = 251. (–)-Spongianolide A = 484. Spongianolide B = 485. Spongianolide C = 486. Spongianolide D = 487. Spongianolide E = 488. Spongianolide F = 489. (–)-Sporochnol A = 1026. (+)-Sporochnol A = 1027. Sporochnol C = 1028. Stellettin F = 753. Stellettin A = 754. Stellettin B = 755.

Stellettin C = 756. Stellettin D = 757. Stellettin E = 758. Stelliferin G = 759. Stichoposide A = 672. Stolonidiol = 31. Strongylin A = 1029. Strongylophorine 1 = 1030. Strongylophorine 2 = 1031. Strongylophorine 3 = 1032. (14R)-Stypodiol = 1033. epi-Stypodiol = 1033. (–)-Stypoldione = 1034. Stypoquinonic acid = 1035. Stypotriol = 1036. Suberitenone A = 598. Suberitenone B = 599. (+)-Subersic acid = 1037. (–)-Subersic acid = 1038. T epi-Taondiol = 1039. Taxol = 61. Terretonin F = 1040. Terretonin G = 1041. Territrem B = 1042. (+)-Testudinariol A = 783. (+)-Testudinariol B = 784. (9Z,9′Z)-5,5′,6,6′-Tetrahydro-β,β-carotene-4,4′diol = 792. (9Z,9′Z)-5,5′,6,6′-Tetrahydro-β,β-carotene-4,4′dione = 790. Tetrahydrohalenaquinone A = 337. Tetrahydrohalenaquinone B = 338. (9Z,9′Z)-5,5′,6,6′-Tetrahydro4′-hydroxy–β,βcaroten-4-one = 791. 2-Tetraprenylbenzoquinol = 1043. Teurilene = 614. Thaimoluccensin A = 780. Thaimoluccensin C = 721. Thorectandrol A = 458. Thorectandrol B = 459. Thorectidaeolide A = 433. Thorectidaeolide B = 434. Thorectolide-25-acetate = 380. Thyrsenol A = 615. Thyrsenol B = 616. Thyrsiferol 23-acetate = 617. α-Tocomonoenol = 1044.

Index 1 Compound Name and Synonym Index

δ-Tocotrienol = 1045. δ-Tocotrinol epoxide = 1046. 15α,19,20-Tri-O-acetylpuupehenol = 1047. Tricycloalternarene A = 1048. Tricycloalternarene B = 1049. Tricycloalternarene C = 1050. (12β,16α,24ξ)-Trihydroxy-17-scalaren-25,24olide = 545. Tropolactone A = 1051. Tropolactone B = 1052. Tropolactone C = 1053. Tsitsixenicin A = 153. Tsitsixenicin B = 154. Tsitsixenicin C = 155. Tsitsixenicin D = 156. Typicoside A1 = 699. Typicoside C1 = 700. U Untenic acid = 394. Untenospongin B = 395. Untenospongin C = 396. Ursolic acid = 781. V Venustatriol = 618. W Wiedendiol A = 1054. Wiedendiol B = 1055. X Xeniafaraunol A = 290. Xeniafaraunol B = 291. 1(9),6,13-Xenicatriene-18,19-dial = 143. 1(9),6,13-Xenicatrien-18-oic acid = 146. 1(9),6,13-Xenicatrien-19,18-olide = 145.

Xeniolactone B = 157. Xeniolide I = 158. Xestoquinolide A = 1056. Xestoquinolide B1 = 1057. Xestoquinolide B2 = 1058. Xestoquinol 16-sulfate = 339. Xestoquinone = 340. Xestosaprol A = 341. Xestosaprol A epimer = 338. Xestosaprol A 13-hydroxy-16-ketone isomer = 342. Xestosaprol B = 343. Xestosaprol F = 344. Xestosaprol G = 345. Xestosaprol H = 346. Xestosaprol I = 347. Xestosaprol J = 348. Xestosaprol K = 349. Xestosaprol L = 350. Xestosaprol M = 351. Xestosaprol O = 352. Xylorumphiin I = 722. Y Yahazunol = 1059. Z Zahavin A = 159. Zahavin B = 160. Zizanin A = 492. Zoanthamide = 771. Zoanthamine = 772. Zoanthenamine = 773. Zonaquinone acetate = 1060. (+)-Zonarol = 1061. Zooxanthellamine = 774.

413

Index 2 Compound Molecular Formula Index The Molecular Formula Index of HAMNP Volume 2 lists the molecular formulae of all 1,061 active isolated compounds from marine organisms given in the HAMNP Volume 2 in Hill convention order. Under a bold formula, all related compound names following code numbers are listed in the code number order too. C13 C13H20O3 – 3-Hydroxy-5-megastigmene-7,9dione, 801.

C18H28O2 – Elisabethin C, 271. C18H28O3 – Conidiogenone H, 320.

C15 C15H22O4 – 9ʹ-Apo-fucoxanthinone, 798.

C19 C19H24O3 – Acalycixeniolide D, 164. C19H24O4 – JBIR 65, 303. C19H24O5 – Myrocin D, 304. – Erythrolic acid D, 916. C19H25NO6S – Conthiaquinone A, 873. C19H26O2 – Acalycixeniolide B, 162. C19H26O3 – Acalycixeniolide C‡, 163. – Caribenol A, 293. C19H26O4 – Elisabanolide, 298. – 3-epi-Elisabanolide, 299. C19H27NO4 – Glaciapyrrole A, 936. C19H28O2 – Cespitularin E, 57. – Acalycixeniolide A, 161. – Elisabethin B, 270. C19H28O3 – Acalycixeniolide K, 167. – Acalycixeniolide L, 168. – Caribenol B, 294. C19H28O5 – Globostelletin A, 733. C19H33O3 – Conidiogenone I, 321.

C16 C16H20Br2O2 – Cyclocymopol, 887. C16H20O2 – epi-Conicol, 872. C16H22O – (–)-Sporochnol A, 1026. – (+)-Sporochnol A, 1027. C16H22O2 – Sporochnol C, 1028. C17 C17H18O3 – Sargasal II, 1018. C17H20O3 – Sargasal I, 1017. C17H24O2 – Amphilectolide, 264. C17H24O5 – Guignardone B, 937. C17H26O5 – Guignardone I, 938. C17H28O3 – Cavernosine, 799. C18 C18H23BrO5 – Hamigeran E, 943. C18H24O5 – Pseudoalteromone A, 1000. C18H26O3 – Nanolobatolide, 305.

C20 C20H12O5 – Halenaquinone, 327.

Index 2 Compound Molecular Formula Index

C20H13ClO5 – 15-Chloro-14-hydroxyxestoquinone, 310. – 14-Chloro-15-hydroxyxestoquinone, 311. C20H14O4 – Xestoquinone, 340. C20H14O5 – Halenaquinol, 325. C20H14O8S – Halenaquinol O16-Sulfate, 326. C20H16O2 – Xestosaprol M, 351. C20H16O4 – Xestoquinolide A, 1056. C20H16O5 – 14,15-Dihydroxymethylxestoquinone, 322. – (–)-Prehalenaquinone, 334. C20H16O7S – Xestoquinol 16-sulfate, 339. C20H18O3 – Xestosaprol I, 347. – Xestosaprol L, 350. C20H18O4 – Xestosaprol G, 345. – Xestosaprol K, 349. C20H20O5 – Tetrahydrohalenaquinone A, 337. – Tetrahydrohalenaquinone B, 338. – Xestosaprol A, 341. – Xestosaprol A 13-hydroxy-16-ketone isomer, 342. C20H22O5 – Xestosaprol B, 343. C20H24O2 – Frondosin B, 931. C20H26O3 – Halimedalactone, 277. – Halimedatrial, 278. – Colombiasin A, 312. – Elisapterosin B, 324. C20H26O4 – Blumiolide C, 137. – Aberrarone, 309. C20H27NO6S – Conthiaquinone A methyl ether, 874. C20H28O – Cespitularin B, 54. – Sinulobatin B, 106.

415

C20H28O2 – (1R*)-Dolabella-4(16),7,11(12)-triene-3,13dione, 17. – (1R*,12R*)-Dolabella-4(16),7,10-triene-3,13dione, 21. – Cyanthiwigin B, 36. – Cespitularin A, 53. – Acalycigorgin C, 121. – Deoxyxeniolide B, 141. – Xeniafaraunol A, 290. C20H28O3 – Clavirolide B, 9. – Clavirolide D, 11. – Clavirolide E, 12. – Clavulactne, 13. – Dolabella-4(16),7-diene-10,11-epoxy-3,13dione, 18. – Dolabella-4(16),10-diene-7,8-epoxy-3,13dione, 19. – Cespitularin F, 58. – Cespitularin H, 59. – 8-Deoxyxeniolide A, 140. – 8-Deoxyxeniolide B, 142. – Florlide D, 149. – Phomactin B2, 283. – Phomactin C, 284. – Xeniafaraunol B, 291. C20H28O4 – Clavirolide A, 8. – 7-Hydroperoxydolabella-4(16),8(17),11(12)triene-3,13-dione, 28. – Cespitularin D, 56. – Blumiolide A, 135. – Blumiolide B, 136. – 9-Deoxy-7,8-epoxy-isoxeniolide A, 139. – Xeniolactone B, 157. – Elisabethin D, 300. – Globostelletin B, 734. C20H28O5 – Elisapterosin A, 323. – Jaspiferal G, 751. C20H28O6 – Xeniolide I, 158. C20H29ClO3 – Molokinenone, 979. C20H30 – (1α,4αH)-14-Serrulatene, 244. C20H30O – 3,7,18-Dolabellatrien-9-one, 22.

416

Index 2 Compound Molecular Formula Index

– Cyanthiwigin A, 35. – Cyanthiwigin F, 40. – 14-Serrulaten-7-ol, 245. – Conidiogenone B, 314. C20H30O2 – Claenone, 7. – 3,4-Epoxy-14-oxo-7,18-dolabelladiene, 27. – (1R*,3R*)-3-Hydroxydolabella-4(16),7,11(12)triene-3,13-dione, 29. – Cyanthiwigin E, 39. – Cyanthiwigin U, 42. – Cyanthiwigin Z, 43. – Acalycigorgin E, 123. – Dictyodial, 143. – Dictyolactone, 145. – Reiswigin B, 252. – Focardin, 274. – Conidiogenone C, 315. – Conidiogenone D, 316. – Conidiogenone E, 317. – Conidiogenone F, 318. – Conidiogenone G, 319. C20H30O3 – Clavirolide C, 10. – Dolabellanone 9, 20. – (+)-Spatol, 50. – Acalycixeniolide I, 125. – Acalycixeniolide J, 126. – Hydroxydictyodial, 151. – Acalycixeniolide F, 166. – Lobatrienolide, 194. – 3-Epiaplykurodinone B, 272. – Epoxyfocardin, 273. – Phomactin D, 285. – Phomactin E, 286. – Phomactin G, 288. C20H30O4 – Florlide B, 170. – Phomactin A, 280. – Phomactin B, 281. – Phomactin B1, 282. – Phomactin F, 287. C20H30O5 – Asterolaurin L, 134. C20H30O6 – Novaxenicin B, 152. C20H31BrO2 – Aplysiadiol, 171.

C20H32 – Ineleganene, 188. – Emmottene, 203. – 4,9,15-Bifloratriene, 204. C20H32O – 3,4-Epoxy-7,18-dolabelladiene, 23. – 7,8-Epoxy-3,18-dolabelladiene, 24. – Palominol, 30. – Cyanthiwigin C, 37. – Cespitularin C, 55. – Eunicol, 172. – Faraunatin, 175. – 17R,18-Epoxy-8,10,13(15)-lobatriene, 179. – Fuscol, 183. – Isopachydictyol A, 201. – Pachydictyol A, 202. C20H32O2 – 7,8-Epoxy-3,12-dolabelladien-14-one, 25. – 3,4-Epoxy-14-hydroxy-7,18-dolabelladiene, 26. – Cyanthiwigin D, 38. – Dilophic acid, 146. – Cyclolobatriene, 177. – Dictyoxepin, 178. – 14,18-Epoxyloba-8,10,13(15)-trien-17-ol, 180. – Eunicidiol, 182. – Lobatriene, 190. – Acutilol A, 195. – Acutilol B, 197. – Dictyol F, 199. – Epidictyol F, 200. – (–)-Reiswigin A, 251. – Sinutriangulin A, 289. C20H32O3 – Dolatriol, 33. – Cyanthiwigin J, 41. – Lobocompactol A, 173. – Lobocompactol B, 174. C20H32O4 – Stolonidiol, 31. – 13,16-Spatadiene-5,15,18,19-tetrol, 49. C20H32O6 – Bicycloalternarene A, 859. C20H34BrClO2 – Dactylomelol, 260. C20H34O – Palmatol, 176.

Index 2 Compound Molecular Formula Index

C20H34O2 – (17R)-Loba-8,10,13(15)-triene-17,18-diol, 192. – Dictyol C, 198. – Conidiogenol, 313. C20H34O3 – Loba-8,10,13(15)-triene-16,17,18-triol, 193. C20H35BrO2 – 14-Bromo-1-obtusene-3,11-diol, 249. C21 C21H14O6 – 14-Methoxyhalenaquinone, 331. C21H16O5 – 15-Hydroxymethylxestoquinone, 328. – 14-Hydroxymethylxestoquinone, 329. – 15-Methoxyxestoquinone, 332. – 14-Methoxyxestoquinone, 333. C21H19NO7S – Xestosaprol O, 352. C21H20O4 – Xestosaprol J, 348. – Neopetrosiquinone A, 983. C21H22O3 – Neopetrosiquinone B, 984. C21H24O5 – Rossinone B, 1007. C21H26O2 – Frondosin C, 932. C21H26O3 – Furospongin 5, 363. – Cyclofurospongin 2, 384. – 1,11-Di-3-furanyl-4,8-dimethyl-1,4,8-undecatrien-6-ol, 385. – Furospongin 2, 386. – Untenospongin B, 395. – Untenospongin C, 396. – (+)-Frondosin D, 933. – (–)-Frondosin D, 934. – Puupehedione, 1001. C21H26O6 – Plumarellide, 306. C21H27NO – Pseudopteroxazole, 100. C21H28O2 – Helioporin E, 68. – Helioporin F, 69. – Helioporin G, 70. – Arenarone, 839. – Avarone, 854.

417

– Frondosin A, 929. – (–)-Frondosin A, 930. – Neoavarone, 982. C21H28O3 – Helioporin A, 64. – Helioporin C, 66. – Cacospongienone A, 382. – Cacospongienone B, 383. – Furospongolide, 387. – Untenic acid, 394. – 3ʹ-Hydroxyavarone, 953. – (–)-Puupehenone, 1002. – (+)-Puupehenone, 1003. C21H28O4 – 3ʹ,6ʹ-Dihydroxyavarone, 907. – 15-Oxopuupehenol, 991. – Penicillipyrone B, 992. – Rossinone A, 1006. C21H28O7 – Asperdemin, 844. C21H29ClO2 – 6ʹ-Chloroaureol, 868. C21H29NO – Secopseudopteroxazole, 243. C21H30O2 – Helioporin D, 67. – Metachromin V, 822. – Arenarol, 838. – Aureol, 845. – Avarol, 853. – Chromazonarol, 870. – ent-Chromazonarol, 871. – Farnesylhydroquinone, 926. – Isozonarol, 963. – Neoavarol, 981. – (+)-Zonarol, 1061. C21H30O3 – Helioporin B, 65. – 6ʹ-Hydroxyavarol, 952. C21H30O5 – Acalycixeniolide H, 124. – Sarcophytin, 308. C21H30O6 – Bicycloalternarene C, 861. – Bicycloalternarene D, 862. C21H31N – 7-Isocyano-10,14-amphilectadiene, 72. – 7-Isocyanoamphilecta-11(20),15-diene, 73. – 7-Isocyano-11,14-epi-amphilectadiene, 74.

418

Index 2 Compound Molecular Formula Index

– 7-Isocyano-11(20),14-epi-amphilectadiene, 75. – 7-Isocyano-1(14),15-neoamphilectadiene, 77. – 7-Isocyano-11-cycloamphilectene, 110. – 7-Isocyano-10-cycloamphilectene, 111. – (1S*,3S*,4R*,7S,8S*,11R*,12R*,13S*,20S*)-7Isocyanoisocycloamphilect-14-ene, 117. C21H31NO2 – Kalihipyran A, 236. – Kalihipyran C, 238. C21H31NOS – 7-Isothiocyanato-11(20),14-epiamphilectadien-12-ol, 78. C21H32ClNO2 – Kalihinol Y, 234. – Δ9-Kalihinol Y, 235. – Kalihipyran B, 237. C21H32O3 – (1R*,2R*,4S*,15E)-Loba-8,10,13(14),15(16)tetraen-17,18-diol-17-acetate, 189. – Yahazunol, 1059. C21H32O4 – Chatancin, 295. – Tricycloalternarene A, 1048. – Tricycloalternarene C, 1050. C21H33NO – (1R*)-7-Formamido-11(20),14-amphilectadiene, 62. – (1S*)-7-Formamido-11(20),15-amphilectadiene, 63. – 7-Formamido-11(20)-cycloamphilectene, 109. – Cavernene A, 206. C21H33NO2 – Cavernene D, 209. – Elisabethamine, 210. – Kalihinene F, 222. C21H33NS – 10-Isothiocyanatobiflora-4,15-diene, 218. C21H34ClNO2 – Kalihinene E, 221. – Kalihinene X, 223. – Kalihinene Y, 224. – Kalihinene Z, 225. C21H34O – Fuscol methyl ether, 184. C21H34O6 – Bicycloalternarene B, 860. C21H35NO – Cavernene B, 207. – Cavernene C, 208.

C22 C22H19NO6S – Xestoquinolide B1, 1057. – Xestoquinolide B2, 1058. C22H19NO7S – Secoadociaquinone A, 335. – Secoadociaquinone B, 336. C22H22O5 – Xestosaprol F, 344. – Xestosaprol H, 346. C22H26O3 – Metachromin W, 823. C22H26O4 – Halitunal, 261. C22H26O9 – Bielschowskysin, 292. C22H27NO3 – 15-Cyanopuupehenone, 886. C22H28O3 – Frondosin E, 935. C22H28O4 – Metachromin E, 817. – Corallidictyal A, 875. – Corallidictyal B, 876. – 10,17-O-Cyano-4,5-di-epi-dactylospongiaquinone, 884. – 8-epi-Dactyloquinone, 899. – Dactyloquinone B, 900. – Liphagal, 964. – Renierin B, 1004. C22H29BrO3 – Peyssonol A, 995. C22H29NO3 – 15-Cyanopuupehenol, 885. C22H30O3 – Sinulobatin A, 105. – Globostelletin C, 735. – Globostelletin D, 736. – Metachromin U, 821. – APS451275-1, 837. C22H30O4 – Globostelletin E, 737. – Globostelletin F, 738. – Metachromin A, 814. – Metachromin C, 815. – Bolinaquinone, 866. – Corallidictyal C, 877. – Corallidictyal D, 878. – 4,5-Di-epi-dactylospongiaquinone, 906.

Index 2 Compound Molecular Formula Index

– 5,8-Di-epi-ilimaquinone, 908. – (–)-Hyatellaquinone, 950. – (+)-Hyatellaquinone, 951. – Isometachromin, 960. – Isospongiaquinone, 961. – 5-epi-Isospongiaquinone, 962. – Mamanuthaquinone, 966. C22H30O5 – Elisabethin D acetate, 301. – Jaspiferal E, 749. – Jaspiferal F, 750. – Cystodione C, 895. – Cystodione D, 896. C22H30O6 – Asterolaurin F, 133. C22H30O7S – Siphonodictyal C, 1022. C22H30O10S2 – Akadisulfate B, 835. C22H32Br2O5 – 10-Acetoxyangasiol, 250. C22H32N2 – 7,20-Diisocyanoisocycloamphilectane, 114. C22H32N2O – (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20Isocyano-7-isocyanoisocycloamphilectane, 116. – (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20Isocyanato-7-isocyanoisocycloamphilectane, 118. – Kalihinene, 220. C22H32N2O2 – 6-Hydroxykalihinene, 217. C22H32N2O2S – 10-Isothiocyanatokalihinol C, 219. C22H32N2O3S C22H32N2S – 7-Isocyano-15-isothiocyanato-11(20)-amphilectene, 76. – (1S,3S,4R,7S,8S,11S,12S,13S,15R,20R)-20Isocyano-7-isothiocyanatoisocycloamphilectane, 112. C22H32N9O2 – Bis(sulfato)cyclosiphonodictyol A, 865. C22H32O3 – 3-Acetoxy-4E,8,18-dolabellatrien-16-al, 3. – Sinulobatin C, 107. – Acetylcoriacenone, 263. – Isoacetylcoriacenone, 279.

419

– 15α-Methylpuupehenol, 977. – Strongylin A, 1029. – Wiedendiol A, 1054. – Wiedendiol B, 1055. C22H32O4 – 16-Acetoxy-7,8-epoxy-3,12(18)-dolabelladien13-one, 4. – Dilophus ether, 52. – Dilopholide, 147. – 4-Acetoxycrenulide, 169. – 15-Methoxypuupehenol, 974. – Penicilliumin A, 993. C22H32O5 – 6-Acetoxy-7,8-epoxy-3,12-dolabelladien-13one, 5. – Cespitulin G, 60. – Asterolaurin D, 131. C22H32O7S – Siphonodictyal sulfate, 1023. C22H32O10S2 – Akadisulfate A, 834. C22H33ClN2O2 – Kalihinol A, 226. – Kalihinol D, 227. – Kalihinol E, 228. C22H33ClN2O2S – Kalihinol X, 232. – 10-epi-Kalihinol X, 233. C22H33ClN2O2S2 – 10-epi-kalihinol I, 230. C22H34N2O – 7-Formamido-20isocyanoisocycloamphilectane, 115. C22H34N2O2 – 15-Formamidokalihinene, 213. C22H34O2 – Durbinal C, 248. C22H34O3 – 14,17-Epoxyloba-8,10,13(15)-trien-18-ol acetate, 181. – Acutilol A acetate, 196. C22H34O4 – Dolatriol-6-acetate, 34. – Fukurinolal, 150. – 4-Acetylaplykurodin B, 262. – Epoxyphomalin D, 915. C22H34O5 – Tricycloalternarene B, 1049. – Stolonidiol-17-acetate, 32.

420

Index 2 Compound Molecular Formula Index

C22H35ClN2O3 – 10-Formamidokalihinol A, 215. – 10-Formamidokalihinol E, 216. C22H35ClN2O3S – 10-Formamido-5-isothiocyanatokalihinol A, 212. – Kalihinol J, 231. C22H35ClN2O4 – 10-Formamido-5-isocyanatokalihinol A, 211. C22H36N2O2 – 7,20-Diformamidoisocycloamphilectane, 108. C22H36O2 – 18-Acetoxy-dolabelladiene, 2. C22H36O3 – 18-Acetoxy-10-hydroxy-2,7-dolabelladiene, 6. – Loba-8,10,13(15)-triene-17-acetoxy-18-ol, 191. C22H36O4 – 5-Acetoxy-10,18-dihydroxy-2,7dolabelladiene, 1. – Dictyoepoxide, 144. C23 C23H28O3 – Dysideavarone A, 911. – Dysideavarone B, 912. – Dysideavarone C, 913. – Dysideavarone D, 914. C23H29ClO5 – Ascofuranone, 842. C23H30O4 – 20-O-Acetylpuupehenone, 825. C23H30O6 – Acalycixeniolide E, 165. C23H31ClO5 – Ascofuranol, 841. C23H32O3 – Dictyoceratin C, 905. C23H32O4 – 6ʹ-Acetoxyavarol, 824. – Cystoazorone A, 891. – Cystoazorone B, 892. – Smenorthoquinone, 1024. – Smenospondiol, 1025. C23H32O5 – Cyclospongiacatechol, 888. – Dictyoceratin B, 904.

C23H32O7 – Ethyl plumarellate, 302. C23H33NO5S – Melemeleone B, 967. C23H33N3O2 – Kalihinol F, 229. C23H33N3O2S3 – 5,10-Biisothiocyanatokalihinol G, 205. C23H34N2O2 – 10-Formamidokalihinene, 214. C23H34O4 – Acalycigorgin D, 122. C23H34O5 – Irciformonin I, 388. C23H36O3 – Durbinal B, 247. C24 C24H30O7 – Cristaxenicin A, 138. C24H32O2 – Plakotenin, 997. C24H32O3 – Phorone A, 597. C24H32O4 – Peyssonol B, 996. C24H32O6 – Tsitsixenicin D, 156. – Rietone, 1005. C24H32O7 – Tsitsixenicin C, 155. C24H32O8 – Asterolaurin E, 132. C24H33NO4 – Beauversetin, 858. C24H34O4 – Sinulobatin D, 113. – Polyfibrospongol A, 998. C24H34O5 – 2,13-Diacetoxy-3,7,18-dolabellatrien-9one, 15. – 19,20-Diacetoxy-7,8-epoxy-3,12,13dolabellatrien, 16. – Tsitsixenicin A, 153. – Metachromin D, 816. – Polyfibrospongol B, 999. C24H34O6 – Dilkamural, 51. – Tsitsixenicin B, 154.

Index 2 Compound Molecular Formula Index

– 19-Hydroxypolyfibrospongol B, 956. C24H34O8 – Chromodorolide C, 297. C24H36O3 – Rhopaloic acid C, 393. – Petrosaspongiolide K, 594. C24H36O5 – 10,18-Diacetoxydolabella-2,7E-dien-6one, 14. C24H38O3 – Rhopaloic acid A, 391. – Rhopaloic acid B, 392. – 3-Hydroxy-3,4,6-trimethyl-6-(2-methyl-10phenyl-9-decenyl)-1,2-dioxane, 410. C24H40O3 – 3-Hydroxy-3,4,6-trimethyl-6-(2-methyl-10phenyldecyl)-1,2-dioxane, 411. C24H40O4 – 13R,16R,17R-Muqubilin A, 420. – 13R,16S,17R-Muqubilin A, 421. – 13S,16R,17S-Muqubilin A, 422. – Sigmosceptrellin A, 455. – Sigmosceptrellin B, 456. – Sigmosceptrellin C, 457. C24H40O6 – Aikupikoxide A, 381. – ent-(–)-Muqubilone, 389. – (+)-Muqubilone B, 390. C24H42O5 – Mycaperoxide A, 451. – Mycaperoxide B, 452. C25 C25H28O5 – 8,9-Dehydroircinin 1, 355. C25H29ClO4 – Merochlorin A, 590. – Merochlorin B, 591. C25H30O5 – (S)-Ircinin 1, 365. – (R)-Ircinin 1, 366. – Ircinin 2, 369. – Sarcotin D, 378. – Sarcotin E, 379. C25H30O8S – (S)-Ircinin 1 O-sulfate, 367. – (S)-Ircinin 1 O-sulfate Δ11-isomer, 368. C25H32O3 – Isophorbasone A, 585.

C25H32O4 – Hippospongin, 407. – Phorbaketal I, 431. C25H32O8 – Austalide U, 852. C25H32O9 – Austalide R, 851. C25H33O21− – Homoplakotenin sodium salt, 949. C25H34O2 – Ophiobolin G, 493. – 6-epi-Ophiobolin G, 494. – Homoplakotenin, 948. C25H34O3 – Phorbasone A, 595. C25H34O4 – Fasciculatin, 357. – Isofasciculatin, 370. – Isopalinurin, 371. – Palinurin, 374. – Sarcotin A, 375. – Sarcotin B, 376. – Sarcotin C, 377. – Alotaketal A, 400. – Phorbaketal A, 427. – Phorbaketal H, 430. – Luffarin C, 447. – Globostelletin G, 739. – Jaspolide F, 752. – 2ʹ,5ʹ-Diacetylavarol, 903. C25H34O5 – Demethylfurospongin 4, 356. – Jaspiferal C, 747. – Jaspiferal D, 748. C25H34O6 – Fasciospongide A, 406. C25H34O7 – Acalycigorgin A, 119. – Austalide P acid, 850. C25H34O7S – Fasciculatin O-sulfate, 358. C25H34O8 – Acalycigorgin B, 120. C25H36O2 – 6-epi-Ophiobolin N, 497. – Ophiobolin U, 500. C25H36O3 – Cyclolinteinone, 403. – Isodehydroluffariellolide, 412.

421

422

Index 2 Compound Molecular Formula Index

– Luffariolide A, 414. – Palauolide, 453. – 25-Hydroxy-13(24),15,17-cheilanthatrien -19,25-olide, 465. – Ophiobolin K, 496. – 25-Deoxycacospongionolide B, 575. – Hippospongide A, 579. – 13E-Lintenone, 586. – 13Z-Lintenone, 587. C25H36O4 – Cacospongionolide D, 354. – 5-[13-(3-Furanyl)-2,6,10-trimethyl-3,5tridecadienyl]-4-hydroxy-3-methyl-2(5H)furanone, 361. – Okinonellin B, 373. – Cyclolinteinol, 401. – Luffariolide E, 418. – (6E)-Neomanoalid-24-al, 424. – Phorbaketal B, 428. – Phorbaketal C, 429. – Thorectidaeolide A, 433. – Thorectidaeolide B, 434. – Ophiobolin A, 491. – 24-Methyl-25-nor-12,24-dioxo-16-scalaren-22oic acid, 531. – Cacospongionolide B, 572. – Cacospongionolide E, 573. – Cacospongionolide F, 574. – Metachromin F, 818. C25H36O5 – Manoalide, 419. – Secomanoalide, 432. – Luffarin A, 446. – Petrosaspongiolide R, 483. – Luffariellin A, 588. – Luffariellin B, 589. C25H36O6 – Pseudopterosin A, 79. – Pseudopterosin F, 84. – Pseudopterosin T1aA, 95. – Halorosellinic acid, 490. C25H36O7 – Fasciospongide B, 359. – Fasciospongide C, 360. – Petrosaspongiolide H, 476. C25H37BrO5 – Neomangicol B, 593. C25H37ClO5 – Neomangicol A, 592.

C25H38O – Furospinulosin 1, 362. C25H38O2 – Luffarin Q, 372. – 16-Deoxoisodehydroluffariellolide, 404. C25H38O3 – (–)-Idiadione, 364. – Luffariellolide, 413. – Thorectandrol A, 458. – Hamiltonin E, 463. – 25-Hydroxy-13(24),17-cheilanthadien-16,19olide, 464. – Ophiobolin C, 492. – Ophiobolin H, 495. – 12-Deacetoxyscalaradial, 508. – 12-epi-O-Deacetyl-19-deoxyscalarin, 511. – 12-Deacetyl-12,18-diepi-Scalaradial, 512. – 12-Desacetylfuroscalarol, 517. – 24,25-Epoxy-25-hydroxy-16-scalaren-12-one, 520. – Asperterpenoid A, 569. – (–)-Hyrtiosal, 581. C25H38O4 – Durbinal A, 246. – Luffariolide B, 415. – Luffariolide D, 417. – (6Z)-Neomanoalide, 425. – (6E)-Neomanoalide, 426. – Cladocoran B, 438. – Luffarin K, 449. – Luffarin L, 450. – Palauolol, 454. – 13,16-Epoxy-25-hydroxy-17-cheilanthen-19,25olide, 462. – Lintenolide C, 467. – 16-O-Deacetyl-16-epi-scalarobutenolide, 513. – 12α,25α-Dihydroxy-16-scalaren-24,25-olide, 519. – Salmahyrtisol C, 535. – Sesterstatin 1, 541. – Sesterstatin 2, 542. – Sesterstatin 3, 543. C25H38O5 – 3-Hydroxy-4,6-dimethyl-6-(2-methyl-10phenyl-9-decenyl)-1,2-dioxan-3-acetic acid, 408. – Lintenolide D, 468. – Lintenolide E, 469.

Index 2 Compound Molecular Formula Index

– Petrosaspongiolide P, 481. – Hyrtiolide, 529. – (12β,16α,24ξ)-Trihydroxy-17-scalaren-25,24olide, 545. C25H38O6 – Secopseudopterosin A, 101. C25H40O2 – Bilosespene A, 435. – Bilosespene B, 436. – (+)-Dysideapalaunic acid, 439. – Kohamaic acid A, 443. C25H40O3 – Kohamaic acid B, 444. – 24,25-Epoxy-16-scalarene-12β,25α-diol, 521. – Hippospongide B, 580. C25H40O4 – Barangcadoic acid A, 353. – (Z)-2,3-Dihydroneomanoalide, 405. – Luffariolide C, 416. – (3β,12α,25α)-24,25-Epoxy-16-scalarene -3,12,25-triol, 522. C25H40O5 – Fuscoside B, 185. – 3-Hydroxy-4,6-dimethyl-6-(2-methyl-10phenyldecyl)-1,2-dioxan-3-acetic acid, 409. C25H40O5S – Halisulfate 7, 440. C25H40O6 – Fuscoside C, 186. – Fuscoside D, 187. C25H40O6S – Halisulfate 9, 441. C25H40O7S – 25-Hydroxyhalisulfate 9, 442. C25H42O – Asperterpenol A, 570. C25H42O2 – Asperterpenol B, 571. C25H42O5 – Muqubilin B, 423. C25H44O5 – Diacarperoxide S, 576. C26 C26H30O8 – Terretonin F, 1040. C26H32O6 – 7-Deacetylgedunin, 779. – Tropolactone C, 1053.

423

C26H33NO5 – 15α-Cyano-19,20-di-O-acetylpuupehenol, 883. C26H34O3 – Avarone adduct A, 855. – Avarone adduct B, 856. C26H34O4 – Strongylophorine 2, 1031. C26H34O7 – Tropolactone A, 1051. C26H35NO7 – 15α-Nitromethyl-19,20-di-O-acetylpuupehenol, 986. C26H36O3 – Avarone adduct C, 857. C26H36O4 – Strongylophorine 3, 1032. C26H36O5 – 24-Methyl-12,24,25-trioxo-16-scalaren-22-oic acid, 560. – 15α-Methyl-19,20-di-O-acetylpuupehenol, 976. C26H36O7 – Zahavin A, 159. – Austalide B, 846. C26H36O8 – 7,8-Epoxyzahavin A, 148. – Zahavin B, 160. – Plumisclerin A, 307. C26H36O9 – Asterolaurin B, 129. – Asterolaurin C, 130. – Chromodorolide B, 296. C26H36O10 – Asterolaurin A, 128. C26H37NO – Homopseudopteroxazole, 71. C26H38O2 – Phyllofenone D, 561. – Fasciquinol B, 928. – 2-Tetraprenylbenzoquinol, 1043. C26H38O3 – Norscalaral C, 534. C26H38O4 – Chevalone E, 867. – Halioxepine, 941. C26H38O5S – Fasciquinol A, 927.

424

Index 2 Compound Molecular Formula Index

C26H38O6 – Pseudopterosin E, 83. – Pseudopterosin G, 85. – Pseudopterosin K, 89. C26H39NO3 – Metachromin H, 820. C26H40O3 – Hyrtial, 528. – Similan A, 544. C26H40O4 – Norscalaral A, 532. – Norscalaral B, 533. C26H40O5 – 16α,22-Dihydroxy-24-methyl-24-oxo-25,12scalaranolide, 552. – 16β,22-Dihydroxy-24-methyl-24-oxo-25,12scalaranolide, 553. C27 C27H27ClO3 – 21-Chloropuupehenol, 869. C27H30O7 – Brevione H, 258. C27H32O5 – Brevione F, 256. – Brevione G, 257. C27H32O7 – 11α-Dehydroxyisoterreulactone A, 902. C27H32O8 – 6R-Hydroxymexicanolide, 717. C27H34O4 – Brevione A, 253. C27H34O5 – Brevione I, 259. C27H34O8 – Austalide I, 847. C27H35BrO4 – Bromophycolide R, 810. C27H35NO6 – Ircinianin lactam A, 584. C27H36Br2O4 – Bromophycolide M, 805. – Bromophycolide N, 806. – Bromophycolide P, 808. – Bromophycolide Q, 809. – Bromophycolide S, 811. – Bromophycolide T, 812. – Bromophycolide U, 813.

C27H36O4 – Brevione B, 254. – Phorbasone A acetate, 596. – Globostelletin H, 740. – Globostelletin I, 741. – Menzoquinone, 968. – Sargachromenol, 1013. C27H36O5 – Jaspiferal A, 745. – Jaspiferal B, 746. – Debromophycolide A, 901. – Meroterphenol D, 972. C27H36O7 – 15α,19,20-Tri-O-acetylpuupehenol, 1047. C27H36O8 – Thaimoluccensin A, 780. C27H36O9 – Austalide M, 848. C27H37BrO3 – Bromophycoic acid E, 269. C27H37Br3O4 – Bromophycolide A, 802. – Bromophycolide B, 803. – Bromophycolide O, 807. C27H37NO7 – 15α-Nitroethyl-19,20-di-O-acetylpuupehenol, 985. C27H38O2 – Sargaol, 1016. C27H38O3 – 9ʹ-Hydroxysarquinone, 957. – Isojaspic acid, 959. – Makassaric acid, 965. – Sargadiol I, 1014. – Sargadiol II, 1015. – (+)-Subersic acid, 1037. – (–)-Subersic acid, 1038. C27H38O4 – Inorolide B, 583. – Noscomin, 989. – Strongylophorine 1, 1030. – (–)-Stypoldione, 1034. – Stypoquinonic acid, 1035. C27H38O5 – 4-Acetoxy-thorectidaeolide A, 398. – Cyclolinteinol acetate, 402. – Ansellone A, 460. – Ansellone B (2012), 568. – Bifurcarenone, 863.

Index 2 Compound Molecular Formula Index

– Meroterphenol A, 969. – Meroterphenol B, 970. C27H38O6 – Thorectolide-25-acetate, 380. – Luffalactone, 445. C27H38O7 – Pseudopterosin B, 80. – Pseudopterosin C, 81. – Pseudopterosin D, 82. – Pseudopterosin P1bD, 92. – Pseudopterosin U1a3, 96. – Pseudopterosin U1a4, 97. – Petrosaspongiolide E, 474. C27H38O8 – Petrosaspongiolide F, 475. C27H38O9 – Terretonin G, 1041. C27H40O2 – δ-Tocotrienol, 1045. C27H40O3 – 3-Methoxy-5-(3,7,11,15-tetramethyl-2,6,10,14hexadecatetraenyl)-1,2-benzenediol, 975. – (14R)-Stypodiol, 1033. – Epi-taondiol, 1039. – δ-Tocotrinol epoxide, 1046. C27H40O4 – 12-epi-Acetylscalarolide, 506. – 12-Deacetoxyscalarin 19-acetate, 509. – 12,16-diepi-12-O-Deacetyl-16-O-acetylfuroscalarol, 510. – Furoscalarol, 523. – Scalaradial, 536. – 12-epi-Scalaradial, 537. – 18-epi-Scalaradial, 538. – Suberitenone A, 598. – Stypotriol, 1036. C27H40O5 – (Z)-24-Acetoxyneomanoalide, 397. – Cladocoran A, 437. – Luffarin D, 448. – Thorectandrol B, 459. – Inorolide C, 466. – 12-O-Acetyl-16-O-deacetyl-16-episcalarobutenolide, 502. – 12-O-Acetyl-16-O-deacetyl-12,16-diepi-scalarolbutenolide, 503. – 12-Deacetoxy-21-acetoxyscalarin, 507. – Deoxoscalarin-3-one, 515. – 12-epi-Deoxoscalarin-3-one, 516.

– Hippospongide C, 526. – 16-epi-Scalarolbutenolide, 540. – Inorolide A, 582. – Meroterphenol C, 971. C27H40O6 – Cavernosolide, 461. – Petrosaspongiolide A, 470. – Petrosaspongiolide B, 471. – Petrosaspongiolide M, 479. – (–)-Spongianolide A, 484. – Spongianolide C, 486. – Spongianolide D, 487. C27H40O7 – Secopseudopterosin B, 102. – Secopseudopterosin C, 103. – Secopseudopterosin D, 104. – Secopseudopterosin H, 241. – Secopseudopterosin I, 242. – Petrosaspongiolide D, 473. – Petrosaspongiolide Q, 482. C27H41BrO5 – Bromophycoic acid D, 268. C27H41NO3 – Ascosalipyrrolidinone A, 843. C27H42O4 – Deoxoscalarin, 514. – 19-Dihydroscalaradial, 518. – Phyllolactone E, 566. – Flabelliferin B, 578. C27H42O5 – (Z)-24-Acetyl-2,3-dihydroneomanoalide, 399. – 21-Hydroxydeoxoscalarin, 527. – Suberitenone B, 599. C27H43BrO4 – Bromophycoic acid A, 265. C27H43BrO5 – Bromophycoic acid B, 266. C27H43BrO6 – Bromophycoic acid C, 267. C27H44O4 – Ophiobolin O, 498. – 6-epi-Ophiobolin O, 499. C27H44O6 – Fuscoside E, 276. C27H44O7 – Fuscoside A, 275. C27H49O4 – Scalarafuran, 539.

425

426

Index 2 Compound Molecular Formula Index

C28 C28H32O8 – Arisugacin A, 840. C28H34O7 – Brevione E, 255. C28H36O8 – Tropolactone B, 1052. C28H36O10 – Austalide N, 849. C28H40Br2O5 – Bromophycolide J, 804. C28H40O5 – 5′-Methoxy-(2E)-bifurcarenone, 973. C28H40O6 – Cystodione A, 893. – Cystodione B, 894. C28H40O7 – Pseudopterosin H, 86. – Pseudopterosin I, 87. – Pseudopterosin J, 88. – Pseudopterosin L, 90. – Pseudopterosin P1aA, 91. – Pseudopterosin Q1a3, 93. – Cystodione E, 897. – Cystodione F, 898. C28H42O5 – 12α-Acetoxy-22-hydroxy-24-methyl-24-oxo16-scalaren-25-al, 548. – 12β-Hydroxy-22-acetoxy-24-methyl-24-oxo16-scalaren-25-al, 556. C28H42O6 – 16β-Hydroxy-22-acetoxy-24-methyl-24-oxo25,12-scalaranolide, 555. – Alotaketal C, 567. C28H44O6 – 12β,16β,22-Dihydroxy-22-acetoxy24β-methylscalaran-25,24olide, 551. C28H44O7 – Lemnabourside B, 239. – Lemnabourside C, 240. C29 C29H34O9 – Territrem B, 1042. C29H36O5 – Expansol B, 925. C29H36O9 – 2-Hydroxyfissinolide, 716.

C29H37NO3 – Metachromin G, 819. C29H40O4 – Zonaquinone acetate, 1060. C29H40O8 – Pseudopterosin Q1b3, 94. – Pseudopterosin W, 98. – Pseudopterosin X, 99. C29H42O5 – 16-Acetylfuroscalarol, 504. C29H42O8 – Petrosaspongiolide C, 472. – Petrosaspongiolide I, 477. – Petrosaspongiolide N, 480. C29H44O5 – Hyrtiosin E, 530. – Phyllolactone C, 564. – Cystoazorol A, 889. C29H44O6 – 21-Acetoxydeoxoscalarin, 501. – Heteronemin, 524. – 12-epi-Heteronemin, 525. – Cystoazorol B, 890. C29H44O7 – Spongianolide B, 485. – Spongianolide E, 488. – Spongianolide F, 489. C29H44O8 – Petrosaspongiolide J, 478. C29H46O5 – 12-Acetoxy-16-hydroxy-20,24-dimethyl-24oxo-25-scalaranal, 547. – (12α,16β,25ξ)-23,25-Cyclo-12-Acetoxy-16,25dihydroxy-20,24-dimethyl-24-scalaranone, 549. C29H48O2 – α-Tocomonoenol, 1044. C29H48O4 – 12α-Acetoxy-24,25-epoxy-24-hydroxy-20,24dimethylscalarane, 546. – Lovenone, 778. C29H50O5 – Crassumtocopherol A, 881. C30 C30H37NO7 – Zoanthamide, 771. C30H38O4 – Stellettin A, 754.

Index 2 Compound Molecular Formula Index

– Stellettin B, 755. C30H38O5 – Expansol A, 924. C30H39NO5 – 28-Deoxyzoanthenamine, 767. – 22-epi-28-Deoxyzoanthenamine, 768. C30H39NO6 – Zoanthenamine, 773. C30H40O4 – Stellettin F, 753. – Stellettin E, 758. C30H41NO5 – Zoanthamine, 772. C30H41NO6 – Cyclozoanthamine, 766. – Oxyzoanthamine, 769. – epi-Oxyzoanthamine, 770. C30H42O6 – Sodwanone G, 762. C30H44O6 – Sodwanone A, 761. C30H45NO5 – Zooxanthellamine, 774. C30H46O3 – Hippospongic acid A, 605. – Penasterone, 692. C30H46O4 – Limatulone, 782. – (+)-Testudinariol A, 783. – (+)-Testudinariol B, 784. C30H46O5 – Dendalone, 550. – Phyllolactone B, 563. C30H46O7S – Methyl 3β-hydroxy-23-oxo-29-nor-lanosta8,24-dien-28-oate 3-sulfate, 687. – Methyl 3β-Hydroxy-23-oxo-29-nor-cycloart24-en-28-oate 3-sulfate, 713. C30H48O3 – Ursolic acid, 781. C30H48O4 – Sexangulic acid, 698. – Sodwanone H, 763. C30H48O5S – 3β-Hydroxycycloart-24-en-23-one 3-sulfate, 709. C30H48O6 – Flabelliferin A, 577.

427

C30H48O6S – Cycloart-24-en-23-one-28-sulfate-3-ol, 707. – 3β,28-Dihydroxy-cycloart-24-en-23-one 3-Osulfate, 708. C30H48O7S – Methyl 3β,23R-dihydroxy-29-nor-lanosta8,24-dien-28-oate 3-sulfate, 686. – Methyl 3β,23R-dihydroxy-29-nor-cycloart-24en-28-oate 3-sulfate, 711. C30H48O9S2 – Cycloart-24-ene-23-one-3β,28-diol 3,28disulfate, 705. C30H50O5 – Sodwanone I, 764. – Sodwanone M, 765. C30H50O5S – Cycloart-24-ene-3β,23R-diol 3-O-sulfate, 704. C30H50O6S – Cycloart-24-ene-3β,23R,28-triol 3-sulfate, 706. C30H50O7 – Martiriol, 612. C30H50O9S2 – Cycloartane-23-one-3β,28-diol 3,28-disulfate, 702. C30H51BrO5 – Magireol B, 610. – Magireol C, 611. C30H51BrO6 – 10-epi-Dehydrothyrsiferol, 603. – Dioxepandehydrothyrsiferol, 604. – Isodehydrothyrsiferol, 607. C30H51BrO7 – Callicladol, 602. – 16-epi-Hydroxydehydrothyrsiferol, 606. C30H51BrO8 – Thyrsenol A, 615. – Thyrsenol B, 616. C30H52O – Lobophytene, 608. C30H52O5 – Teurilene, 614. C30H52O7 – Pseudodehydrothyrsiferol, 613. C30H52O9S2 – Cycloartane-3,28-disulfate-23-ol, 701. – Cycloartane-3β,23ξ,28-triol 3,28-disulfate, 703.

428

Index 2 Compound Molecular Formula Index

C30H53BrO6 – Magireol A, 609. C30H53BrO7 – Aurilol, 601. – Venustatriol, 618. C31 C31H40O10 – Moluccensin R, 719. C31H44O2 – 2-Methyl-2-(tetraprenylmethyl)-2H-1-benzopyran-6-ol, 978. C31H46O2 – Coscinoquinol, 879. C31H46O5S – 2-Pentaprenyl-1,4-benzenediol-4-sulfate, 994. C31H46O6 – Globostellatic acid D, 732. C31H46O6S – Hipposulfate A, 947. C31H46O7 – 12-Acetyl-12-epi-heteronemin, 505. C31H48O5 – Phyllolactone A, 562. C31H48O6 – Fusidic acid, 775. C31H48O6S – Coscinosulfate, 880. – Halisulfate 1, 942. C31H48O7S – Methyl 3β-hydroxy-23-oxocycloart-24-en-28oate 3-sulfate, 712. C31H50O5S – Ircinol sulfate, 958. C31H50O7S – Methyl 3β,23R-dihydroxycycloart-24-en-28oate 3-sulfate, 710. C31H52O – Miliacin, 728. C31H52O6 – Crassumtocopherol B, 882. C32 C32H38O7 – Godavarin A, 714. C32H40O9 – Godavarin D, 715.

C32H42O5 – Stellettin C, 756. – Stellettin D, 757. C32H42O10 – Moluccensin S, 720. C32H44O7 – Globostellatic acid A, 729. C32H46O9 – Euplexide F, 922. – Euplexide G, 923. C32H48O5 – Acetylenoxolone, 723. – 29-Hydroxystelliferin A, 742. – Stelliferin G, 759. C32H48O6 – Phyllolactone D, 565. C32H50O4 – Acetylpenasterol, 620. C32H52O5 – 12α-O-(3-Hydroxy-4-methylpentanoyl)-16αhydroxy-20,24-dimethyl-25-nor-17-scalaren-24-one, 557. C32H52O6 – Foliaspongin, 554. C32H55BrO8 – Thyrsiferol 23-acetate, 617. C33 C33H40O10 – Antheliatin, 127. C33H40O11 – Thaimoluccensin C, 721. C33H44O8 – Helvolic acid, 776. C33H46O9 – 25-Hydroxy-24,25-Dihydrohelvolic acid, 777. C33H48O7 – Globostellatic acid B, 730. – Globostellatic acid C, 731. C34 C34H42O6 – Scabellone B, 1019. C34H48O10 – Euplexide C, 919. C34H48O11 – Euplexide A, 917. – Euplexide D, 920. – Moritoside, 980.

Index 2 Compound Molecular Formula Index

C34H50O6 – 29-Hydroxystelliferin E, 743. – 3-epi-29-Hydroxystelliferin E, 744. C34H56O7 – Raspacionin, 760. C34H58O8 – Auriculol, 600. C35 C35H50O11 – Euplexide E, 921. C35H56O7 – 12α-O-(3-Hydroxypentanoyloxy)-16α-ethoxy24β-hydroxy-20,24-dimethyl-17-scalaren25,24-olide, 558. – 12α-O-(3-Hydroxypentanoyloxy)-16α-ethoxy24α-hydroxy-20,24-dimethyl-17-scalaren25,24-olide, 559. C36 C36H50O11 – Hypoxysordarin, 330. C36H50O12 – 2-Hydroxyxylorumphiin F, 718. – Euplexide B, 918. C36H52O2 – Sarcochromenol A, 1011. C36H54O2 – 2-Hexaprenyl-1,4-benzenediol, 946. C36H54O5S – Sacrohydroquinone sulfate A, 1008. C36H54O6S – Adociasulfate 4, 829. – Adociasulfate 5, 830. – Adociasulfate 6, 831. – Adociasulfate 7, 832. C36H54O8S2 – Akaterpin, 836. C36H54O9S2 – Adociasulfate 1, 826. – Adociasulfate 2, 827. C36H56O9S2 – Adociasulfate 8, 833. C36H56O10S2 – Adociasulfate 3, 828. – Shaagrockol C, 1021. C36H56O12S2 – Shaagrockol B, 1020.

429

C37 C37H50O12 – Xylorumphiin I, 722. C38 C38H56O5 – Halicloic acid A, 939. – Halicloic acid B, 940. C40 C40H52O2 – Canthaxanthin, 788. C40H52O4 (3S,3’S)-Astaxanthin, 786. C40H56 – β-Carotene, 789. C40H56O2 – Cucumariaxanthin A, 790. – Lutein, 795. C40H56O3 – Myxol, 796. C40H56O5 – Fucoxanthinol, 794. C40H58O2 – Cucumariaxanthin B, 791. C40H60O2 – Cucumariaxanthin C, 792. C41 C41H60O2 – Sarcochromenol B, 1012. C41H62O2 – Heptaprenylhydroquinone, 945. C41H62O3 – 5ʹ-Hydroxy-2-heptaprenyl-1,4-benzenediol, 954. C41H62O5S – 2-Heptaprenyl-1,4-benzenediol-4-sulfate, 944. C41H62O8S2 – Sacrohydroquinone sulfate B, 1009. C41H64O13 – Holothurinoside D, 670. C41H64O17S – Holothurin B, 667. C41H66O12 – Eryloside F, 656. C41H66O16S – Echinoside B, 653.

430

Index 2 Compound Molecular Formula Index

C41H66O17S – Leucospilotaside B, 681. C42 C42H50O6 – Dipuupehedione, 909. C42H54O6 – Bispuupehenone, 864. C42H54O10 – Gukulenin A, 44. – Gukulenin F, 48. C42H57NO10 – Gukulenin D, 46. C42H57NO11S – Gukulenin E, 47. C42H58O6 – Fucoxanthin, 793. C42H68O12 – Eryloside F1, 657. C43 C43H59NO10 – Gukulenin C, 45. C43H66O16S – Pentactaside III, 695. C45 C45H74O9 – Plakopolyprenoside, 797. C46 C46H62O9 – (3S,3’S)-Astaxanthin β-D-glucoside, 787. C46H64O8 – (3S,3ʹR)-Adonixanthin-β-D-glucoside, 785. C46H70O2 – Octaprenylhydroquinone, 990. C46H70O5S – Sacrohydroquinone sulfate C, 1010. C46H70O6S – 25ʹ-Hydroxy-2-octaprenyl-1,4-benzenediol-4sulfate, 955. C46H74O19 – Ectyoplaside A, 654. C46H74O20 – Ectyoplaside B, 655.

C47 C47H51NO14 – Taxol, 61. C47H70O17 – Cucumarioside B2, 644. C47H76O18 – Catunaroside A, 724. C48 C48H74O20 – Cucumarioside A10, 642. C48H74O20S – Pentactaside I, 693. – Pentactaside II, 694. C48H78O17 – Catunaroside B, 725. C49 C49H70O9 – Diapolycopenedioic xylosyl ester A, 800. C49H79NO16 – Eryloside H, 659. C50 C50H81NO16 – Eryloside J, 661. C50H81NO17 – Eryloside G, 658. C51 C51H78O3 – Nonaprenylhydroquinone, 987. C51H78O5S – Nonaprenylhydroquinone sulfate, 988. C51H83NO17 – Eryloside I, 660. C52 C52H70O8 – Distrongylophorine, 910. C53 C53H84O25S – Patagonicoside B, 690. C53H86O23 – Catunaroside D, 727.

Index 2 Compound Molecular Formula Index

C54 C54H84O26S – Cucumarioside H3, 646. C54H84O27S – Calcigeroside B, 622. C54H84O28S – Calcigeroside C1, 623. C54H84O28S2 – Hemoiedemoside A, 665. C54H84O31S3 – Hemoiedemoside B, 666. C54H86O23 – Holothurinoside C, 669. C54H86O28S2 – Typicoside C1, 700. C54H87NO21 – Formoside B, 662. C54H88O23 – Catunaroside C, 726. C54H88O29S2 – Patagonicoside A, 689. – Patagonicoside C, 691.

C58H88O12S – Crellastatin K, 634. C58H88O13S – Crellastatin J, 633. C58H88O15S2 – Crellastatin M, 636. C58H90O29S – Cucumarioside H8, 651. C58H94O25 – Holotoxin G, 678.

C55 C55H84O23 – Cucumarioside A13, 643. C55H84O25S – Typicoside A1, 699. C55H86O22 – Cucumarioside A1, 637. C55H90O22 – Cucumarioside A8, 641.

C60 C60H92O29S – Cucumarioside H5, 648. C60H94O29S – Cucumarioside H6, 649. C60H94O32S2 – Cucumarioside I1, 652. C60H96O29 – Holothurinoside A, 668. C60H96O29S – Cucumarioside H7, 650. – Frondoside A, 663.

C56 C56H88O32S3 – Liouvilloside A, 682. C56H90O32S3 – Liouvilloside B, 683.

C59 C59H92O26 – Cladoloside B, 625. C59H92O32S2 – Cucumarioside A3, 639. – Cucumarioside A62, 640. C59H94O29S – Calcigeroside C2, 624. C59H96O25 – Holotoxin F, 677.

C57 C57H84O11S – Crellastatin L, 635. C57H88O24 – Cucumarioside A2, 638.

C61 C61H96O29S – Cucumarioside H2, 645. C61H98N2O25 – Sarasinoside B1, 697. C61H100O35S3 – Frondoside C, 664.

C58 C58H88O11S – Crellastatin I, 632.

C62 C62H100N2O26 – Sarasinoside A1, 696.

431

432

Index 2 Compound Molecular Formula Index

C63 C63H98O30 – Cladoloside B2, 627. C63H100O29S – Cucumarioside H4, 647. C63H100O30 – Cladoloside B1, 626. C65 C65H100O32 – Holotoxin D1, 675. C65H102O31 – Holotoxin E, 676. C65H102O32 – 26-Nor-25-oxo-holotoxin A1, 688. C66 C66H104O31 – Holotoxin A1, 672. C66H104O32 – Holotoxin B, 673. – Holotoxin D, 674. C66H106O32 – Cladoloside C2, 630.

C67 C67H106O32 – Holotoxin A, 671. C67H108O32 – Impatienside A, 680. – Marmoratoside A, 684. C67H108O33 – 17α-Hydroxyimpatienside A, 679. – Marmoratoside B, 685. C67H110O32 – Bivittoside D, 621. C68 C68H106O34 – Cladoloside D, 631. C69 C69H112O34 – 25-Acetoxybivittoside D, 619. C70 C70H110O35 – Cladoloside C, 628. C70H112O35 – Cladoloside C1, 629.

Index 3 Compound Organism Source Index This index lists in alphabetical order all 435 marine organism in Latin names in HAMNP Volume 2, following a code sequence of related active compounds. When one hopes to know the English type name of any marine organism, please see an entry of a related compound in the code sequence. For example, if one hopes to know the English common type name of “Haliclona sp.”, from entry 826 of this index, one will know that the Haliclona sp. is a sponge. A Acalycigorgia inermis 124, 125, 126, 161, 162, 163, 164, 165, 166, 167, 168. Acalycigorgia sp. 119, 120, 121, 122. Acanthella cavernosa 204, 206, 207, 208, 209, 211, 212, 213, 213, 214, 214, 215, 216, 217, 220, 221, 222, 223, 223, 224, 224, 225, 231, 234, 236, 236, 237, 238. Acanthella klethra 220. Acanthella sp. 205, 217, 220, 226, 226, 227, 230, 233, 235. Acanthella spp. 226, 227, 228, 229, 232, 234. Acanthodendrilla sp. 965, 1037. Acanthogorgia sp. 123. Acanthogorgia turgida 123, 162. Acanthoprimnoa cristata 138. Acremonium sp. 841, 842. Actinocucumis typica 699, 700. Actinomadura sp. 303. Actinopyga agassizi 667. Actinopyga echinites 653. Actinopyga flammea 667. Actinopyga lecanora 667. Actinopyga mauritiana 653. Adalaria loveni 778. Adocia aculeata 830. Adocia sp. 114, 327, 340. Adocia sp. [Syn. Haliclona sp.] 826, 827, 828, 829, 830, 831, 832, 833. Adocia spp. 73, 75. Agrobacterium aurantiacum 785, 787. Aka corallifagum 877, 878. Aka coralliphaga 834, 835, 964, 1023. Aka coralliphaga [Syn. Siphonodictyon coralliphaga] 875, 876. Aka sp. 1022. Alcyonium aureum 159, 160. Alcyonium fauri 1005. Alcyonium palmatum 176.

Alternaria sp. 859, 860, 861, 862, 1048, 1049, 1050. Amphidinium sp. 798. Amphiscolops sp. 774. Anthelia glauca 127, 159, 160. Aplidium conicum 873, 874. Aplidium scabellum 1019. Aplidium sp. 1006, 1007. Aplysia dactylomela 249, 260, 1034, 1039. Aplysia depilans 143, 145, 198, 200, 202. Aplysia fasciata 262, 272. Aplysia kurodai 171. Aplysia sp. 297. Aplysia vaccaria 202. Aplysina lacunosa 845. Apostichopus japonicas 625, 672, 673, 674, 675, 676, 677, 678, 688. Arthrinium sp. 304. Arthrospira sp. 789. Ascochyta salicorniae 843. Aspergillus aureolatus HDN14-107 846, 847, 850, 852. Aspergillus insuetus 1040. Aspergillus similanensis sp. nov KUFA 0013 867. Aspergillus sp. 498, 499, 569, 570, 571, 848, 849, 851, 1051, 1052, 1053. Aspergillus sp. OPMF00272 1041. Aspergillus sydowi PFW1-13 776, 777. Aspergillus terreus PT06-2 1042. Aspergillus terreus SCSGAF0162 840, 902. Aspergillus ustus 500. Aspergillus versicolor 844. Asteropus sarasinosum 696, 697. Asterospicularia laurae 128, 129, 130, 131, 132, 133, 134. Axinella weltneri 761, 762, 763, 764, 765. B Beauveria bassiana 858. Bifurcaria galapagensis 863.

434

Index 3 Compound Organism Source Index

Bohadschia bivittata 621. Bohadschia marmorata 619, 621, 679, 680, 684, 685. Brachiaster sp. 509. Briareum polyanthes 203. Bruguiera sexangula 698. C Cacospongia cf. linteiformis 401, 402, 467, 468, 469, 586, 586, 587. Cacospongia linteiformis 403, 486, 487. Cacospongia mollior 508, 523, 536. Cacospongia scalaris 355, 370, 382, 383, 504, 506, 508, 518, 524, 532, 533, 534, 536, 538. Cacospongia sp. 413. Cacospongia spp. 959. Cadlina luteomarginata 460. Callophycus serratus 802, 803, 804, 805, 806, 807, 808, 809, 810, 811, 812, 813, 901. Callophycus sp. 265, 266, 267, 268, 269. Callyspongia sp. 836, 859, 860, 861, 862, 1048, 1049, 1050. Capnella thyrsoidea 153, 154, 155, 156. Carteriospongia flabellifera 577, 578. Carteriospongia foliascens 546, 547, 549, 557, 558, 559. Carteriospongia sp. 362. Catunaregam spinosa 724, 725, 726, 727. Ceramium rubrum 793. Cespitularia hypotentaculata 53, 54, 55, 56, 57, 58, 59. Cespitularia taeniata 60. Chaetomium olivaceum 728. Chionoecetes opilio 280, 281, 282, 283, 284, 285. Chlorella pyrenoidosa 795. Chlorella zofingiensis 789. Chromodoris cavae 296. Chromodoris hamiltoni 463. Chromodoris inornata 466, 501, 503, 515, 516, 527, 582, 583. Cladocora cespitosa 437, 438. Cladolabes schmeltzii 626, 627, 628, 629, 630, 631. Cladolabes sp. 625. Clavularia inflata 17, 18, 19, 21, 28, 29. Clavularia sp. 7, 31. Clavularia viridis 8, 9, 10, 11, 12, 13.

Codium fragile 500. Coelastrella striolata var. multistriata 788. Collisella limatula 782. Colpomenia peregrine 793. Convexella magelhaenica 15, 22. Coscinoderma matthewsi 880. Coscinoderma sp. 440, 879. Crella sp. 632, 633, 634, 635, 636. Cribrochalina sp. 204. Cucumaria frondosa 663, 664. Cucumaria japonica 639, 640, 790, 791, 792. Cylindrotheca closterium 793. Cymbastela hooperi 62, 63, 72, 73, 74, 75, 76, 77, 78, 108, 109, 110, 111, 112, 114, 115, 116, 117, 118, 218. Cymopolia barbata 887. Cystophora expansa 1045. Cystoseira abies-marina 889, 890, 891, 892. Cystoseira amentacea var. stricta 973. Cystoseira stricta 863. Cystoseira tamariscifolia 973, 973. Cystoseira usneoides 893, 894, 895, 896, 897, 898. D Dactylospongia elegans 884, 888, 899, 900, 906, 908. Dactylospongia sp. 470, 471, 905. Darwinella australensis 441. Dendrodoris grandiflora 357. Desmarestia menziesii 968. Diacarnus bismarckensis 389, 390. Diacarnus cf. spinopoculum 420, 421, 423, 456, 457. Diacarnus erythraeanus 381. Diacarnus erythraenus 381, 420, 456. Diacarnus megaspinorhabdosa 576. Dictyopteris undulata 870, 926, 1059, 1061. Dictyopteris undulata [Syn. Dictyopteris zonaroides] 963. Dictyopteris zonaroides [Syn. Dictyopteris undulate] 963. Dictyota acutiloba 178, 195, 196, 197. Dictyota binghamiae 202. Dictyota crenulata 143, 150, 169. Dictyota dentata 198, 202. Dictyota dichotoma 1, 2, 6, 23, 24, 26, 27, 145, 150, 198, 199, 200, 201, 202, 202. Dictyota flabellata 143.

Index 3 Compound Organism Source Index

Dictyota patens 143. Dictyota sp. 3, 144. Dictyota spinulosa 151. Dilophus dichotoma 198. Dilophus guineensis 146. Dilophus ligulatus 147, 150, 169, 263, 279. Dilophus lingulatus 145. Dilophus mediterraneus 143. Dilophus okamurai 51, 52, 150. Dolabella auricularia 33, 34, 600, 601. Dunaliella salina 789. Dysidea arenaria 838, 839, 956, 998, 999. Dysidea avara 853, 854, 903, 911, 912, 913, 914. Dysidea cinerea 435, 436, 824, 907, 952, 953. Dysidea frondosa 929, 931, 932, 933, 935. Dysidea herbacea 387. Dysidea pallescens 871. Dysidea sp. 14, 371, 439, 855, 856, 857, 866, 879, 942, 967, 981, 982, 1003. E Echinopora lamellosa 723. Ectyoplasia ferox 654, 655, 915. Eleutherobia aurea 148. Emericella variecolor GF10 491, 492, 493, 494, 495, 496, 497. Epipolasis reiswigi 35, 36, 37, 38, 251, 252. Erylus formosus 656, 657, 662. Erylus nobilis 658, 659, 660, 661. Erythrobacter sp. 916. Eunicea calyculata 30. Eunicea fusca 172, 182, 183, 184, 185, 186, 187, 275, 276. Eunicea laciniata 30. Eunicea sp. 20. Eunicea tourneforti 4, 5, 16, 25. Eupentacta fraudatrix 637, 638, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652. Euplexaura anastomosans 917, 918, 919, 920, 921, 922, 923. Euplexaura sp. 980. Euplotes focardii 273, 274. Euryspongia sp. 930, 934. Excoecaria agallocha 924, 925. F Fascaplysinopsis reticulata 412, 413. Fascaplysinopsis sp. 453, 454.

435

Fasciospongia cavernosa 354, 461, 572, 573, 574, 575, 799. Fasciospongia rimosa 961. Fasciospongia sp. 359, 360, 362, 406, 440, 441, 442, 927, 928, 966, 975. Flavobacterium sp. 796. Fucus virsoides 793. Fusarium heterosporum CNC-477 592, 593. G Geodia cydonium 304. Geodia japonica 754. Glossodoris atromarginata 520, 521. Glossodoris sedna 556. Glossodoris tricolor 514. Guignardia mangiferae 937. Guignardia sp. 937, 938. H Haematococcus pluvialis 786. Halichondria spp. 531. Haliclona sp. 826, 827, 828, 829, 830, 831, 832, 833, 939, 940, 941. Haliclona sp. [Syn. Adocia sp.] 826, 827, 828, 829, 830, 831, 832, 833. Halimeda scabra 277. Halimeda spp. 278. Halimeda tuna 261, 277. Halorosellinia oceanica BCC5149 490. Hamigera sp. 400. Hamigera tarangaensis 943. Heliopora coerulea 64, 65, 66, 67, 68, 69, 70. Hemioedema spectabilis 665, 666. Heteronema erecta 511, 524. Hijikia fusiformis 793. Hippospongia cf. metachromia 814, 815, 947. Hippospongia communis 386, 945, 990. Hippospongia metachromia 816, 817, 818, 819, 820. Hippospongia sp. 353, 395, 396, 407, 505, 509, 524, 526, 530, 539, 579, 580, 605, 904, 962, 1025. Holothuria atra 667. Holothuria edulis 667. Holothuria floridiana 667. Holothuria forskolii 668, 669, 670. Holothuria impatiens 680. Holothuria leucospilota 667, 681. Holothuria lubrica 667.

436

Index 3 Compound Organism Source Index

Holothuria pervicax 671. Homaxinella sp. 796. Hyatella intestinalis 524, 950, 951. Hypoxylon croceum 330. Hypselodoris orsini 514. Hyrtios cf. erecta 404, 412. Hyrtios cf. erectus 502, 507, 513. Hyrtios communis 398, 433, 434. Hyrtios erecta 419, 425, 426, 505, 511, 521, 522, 524, 525, 528, 530, 535, 537, 541, 542, 543, 581. Hyrtios erectus 529. Hyrtios eubamma 864, 1003. Hyrtios gumminae 511, 529, 539, 544, 545, 581. Hyrtios sp. 380, 517, 519, 845, 864, 869, 886, 909, 974, 979, 1002. Hyrtios spp. 991. I Ianthella basta 357. Ircinia fasciculata 357, 358, 944, 990, 1012. Ircinia formosana 388. Ircinia muscarum 946, 1043. Ircinia oros 365, 367, 368, 369. Ircinia sp. 443, 444, 462, 464, 465, 470, 471, 944, 954, 958, 978, 994, 1008, 1011, 1012. Ircinia spinosula 362. Ircinia spinulosa 944, 946, 955, 990, 1010, 1043. Ircinia spp. 369. Ircinia variabilis 367, 368, 374. Isochrysis aff. galbana 793. J Jaspis sp. 742, 743, 744, 752, 759. Jaspis splendens 1038. Jaspis stellifera 745, 746, 747, 748, 749, 750, 751, 755. L Laurencia japonensis 171. Laurencia obtusa 609, 610, 611, 614, 617. Laurencia sp. 171, 250, 313, 314, 320, 321, 602. Laurencia venusta 618. Laurencia viridis 604, 606, 612, 613, 615, 616. Laurencia viridis sp. nov. 603, 607.

Leiosella idia 524. Lemnalia bournei 239, 240. Lendenfeldia frondosa 552. Lendenfeldia sp. 387, 548, 551, 553, 555, 560. Lobophytum compactum 173, 174. Lobophytum crassum 881, 882, 1000. Lobophytum hirsutum 193. Lobophytum pauciflorum 172, 177, 180, 181, 183, 184, 190, 191. Lobophytum sp. 179, 190, 192, 193, 608. Luffariella geometrica 372, 446, 447, 448, 449, 450. Luffariella sp. 397, 399, 405, 413, 414, 415, 416, 417, 418, 424, 425, 426. Luffariella variabilis 419, 425, 426, 432, 445, 588, 589. M Monanchora sp. 430, 431. Mycale cf. spongiosa 451. Mycale sp. 451, 452. Myrmekioderma styx 35, 36, 37, 38, 39, 40, 41, 42, 43. Myxilla incrustans 858. N Neopetrosia proxima 983, 984. Nephthea sp. 1016. Nostoc commune 989. O Occurs in all higher plants, microorganisms 795. Occurs in animal organisms 962. Occurs in driftwood 330. Occurs in higher plants 728. Occurs in marine animals 962. Occurs in marine invertebrate, pigment in egg yolk and leaves 795. Occurs in marine organisms eg. sponges, esp. of the Poecilosclerida and Axinellida 789. Occurs in plants and animals 789. Occurs in plants, e.g. Labiatae spp., Apocynaceae spp., Rosaceae spp., Oleaceae spp. Arctostaphylos uva-ursi 781. Occurs in sponges 962. Occurs in sponges and other marine organisms 1003. Odontella aurita 793.

Index 3 Compound Organism Source Index

Oncorhynchus keta 1044. P Pachydictyon coriaceum 202, 263, 279. Panicum miliaceum 728. Paraconiothyrium cf. sporulosum 915. Penares incrustans 620, 692. Penicillium chrysogenum 313, 314, 320, 321. Penicillium expansum 924, 925. Penicillium sp. 253, 254, 256, 256, 257, 257, 259, 926, 992. Penicillium sp. F00120 993. Penicillium sp. F23-2 314, 315, 316, 317, 318, 319. Penicillium sp. MCCC 3A00005 255, 256, 257, 258. Pentacta quadrangularis 693, 694, 695. Pentamera calcigera 622, 623, 624. Petalonia binghamiae 793. Petrosaspongia metachromia 905. Petrosaspongia nigra 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 594. Petrosia alfiani 322, 328, 329. Petrosia ficiformis 1040. Peyssonnelia sp. 995, 996. Phaeodactylum tricornutum 793. Phakellia pulcherrima 219, 235. Phialocephala sp. 837. Phoma sp. 285, 286, 287, 288. Phoma sp. SANK11486 281, 282, 283, 284. Phoma sp. SANK11486 and P10364 280. Phorbas gukulensis 44, 45, 46, 47, 48. Phorbas sp. 427, 428, 429, 460, 567, 568, 585, 595, 596, 597. Phyllospongia dendyi 550. Phyllospongia foliascens 554, 561. Phyllospongia lamellosa 562, 563, 564, 565, 566. Phyllospongia sp. 547. Plakortis lita 948, 949, 997. Plakortis simplex 797. Plakortis sp. 408, 409, 410, 411. Pleurobranchus testudinarius 783, 784. Plumarella sp. 302, 306. Plumigorgia terminosclera 307. Polyfibrospongia australis 998, 999. Polysiphonia nigrescens 793.

437

Porphyra spp. 795. Potamon dehaani 795. Prianos sp. 422, 456. Prorocentrum minimum 801. Psammocinia sp. 361, 584. Psammoclema sp. 246, 247, 248. Pseudoalteromonas sp. CGH2XX 1000. Pseudopterogorgia elisabethae 71, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 100, 210, 241, 242, 243, 244, 245, 264, 270, 271, 293, 294, 298, 298, 299, 299, 300, 300, 301, 301, 309, 312, 323, 323, 324, 324. Pseudopterogorgia kallos 292. Pseudopterogorgia sp. 101, 102, 103, 104. Psolus patagonicus 689, 690, 691. Ptilocaulis spiculifer 761. R Raspaciona aculeata 760. Raspaciona larvacid 760. Reniera mucosa 1004. Rhabdastrella globostellata 733, 734, 735, 736, 737, 738, 739, 740, 741, 752, 753, 753, 754, 756, 757, 758. Rhopaloeides sp. 391, 392, 393. Rubritalea squalenifaciens 800. S Sarcophyton elegans 308. Sarcophyton sp. 295. Sarcotragus sp. 988, 1010. Sarcotragus spinosulus 945, 987, 990. Sarcotragus spinulosus 1008, 1009, 1010. Sarcotragus spp. 366, 369, 375, 376, 377, 378, 379. Sargassum serratifolium 1013. Sargassum tortile 957, 1014, 1015, 1016, 1017, 1018, 1045, 1046. Sargassum yezoense 969, 970, 971, 972. Scyphiphora hydrophyllacea 937, 938. Sigmosceptrella laevis 455, 456, 457. Sigmosceptrella quadrilobata 14. Sinularia flexibilis 194. Sinularia inelegans 188. Sinularia nanolobata 105, 106, 107, 113, 305. Sinularia pavida 295, 308. Sinularia sp. 180, 181, 189, 193, 194.

438

Index 3 Compound Organism Source Index

Sinularia triangula 289. Siphonodictyon coralliphaga [Syn. Aka coralliphaga] 875, 876. Siphonodictyon coralliphagum 865, 1022. Smenospongia aurea 845, 868. Smenospongia sp. 419, 1024. Smenospongia spp. 1025. Spatoglossum howleii 50. Spatoglossum schmittii 50. Spongia agaricina 510, 540. Spongia hispida 962. Spongia idia 362, 364, 512, 524, 539. Spongia officinalis 356, 363, 384, 386, 514. Spongia sp. 327, 484, 485, 486, 487, 488, 489, 520, 521, 950. Spongia virgultosa 385. Spongionella sp. 373. Sporochnus bolleanus 1026, 1027, 1028. Sporochnus comosus 793. Staurocucumis liouvillei 682, 683. Stelletta globostellata 729, 730, 731, 732, 744, 754, 755. Stelletta sp. 753, 754, 755, 756, 757, 841, 842. Stelletta tenuis 754. Stichopus chloronotus 667. Stichopus japonicus 671, 672, 673. Stilbella aciculosa 775. Stoechospermum marginatum 49. Strepsichordaia lendenfeldi 547. Streptomyces sp. 590, 591. Streptomyces sp. NPS008187 936. Strongylophora durissima 1030, 1031, 1032. Strongylophora hartmani 1003, 1029. Strongylophora sp. 910. Stypopodium flabelliforme 1034, 1039. Stypopodium zonale 1033, 1034, 1035, 1036, 1039, 1060. Suberites sp. 598, 599. Symbiodinium sp. Y-6 774. Synoicum castellatum 872. T Taxomyces andreanae 61. Terrestrial fungus Penicillium brevicompactum 253, 254, 255. Terrestrial fungus Penicillium cyclopium 313. Terrestrial plants Taxus spp. 61. Tethya aurantium 848, 849.

Thelenota ananas 621, 667. Thorecta horridus 372. Thorecta reticulata 821, 822, 823. Thorecta sp. 362. Thorectandra sp. 454, 458, 459. Toxiclona toxius 1020, 1021. Tricleocarpa fragilis 686, 687, 704, 706, 708, 709, 710, 711, 712, 713. Tuemoya sp. 701, 707. Tydemania expeditionis 701, 702, 703, 705. U Ulva sp. 843. Undaria pinnatifida 793, 794. Unidentified mangrove 569, 570, 571. Unidentified marine alga (family Cladophorace) 781. Unidentified sponge 296, 846, 847, 850, 851, 852, 1051, 1052, 1053. Unidentified sponge (family Adocidae) 218. Unidentified sponge (family Halichondriidae) 394, 942. Unidentified sponge (family Spongiidae) 960. Unidentified sponge (order Dictyoceratida) 531, 825, 883, 976, 977, 985, 986, 991, 1047. Unidentified sponge (order Verongida) 825, 883, 976, 977, 985, 986, 991, 1047. V Verongida sp. 885, 886, 1001. X Xenia blumi 135, 135, 136, 136, 137, 139, 157. Xenia elongata 141. Xenia faraunensis 175, 290, 291. Xenia florida 149, 157, 170, 291. Xenia novaebrittanniae 152, 158. Xenia sp. 140, 142. Xestospongia carbonaria 325, 326, 327, 340. Xestospongia cf. carbonaria 331, 337, 338, 1056, 1057, 1058. Xestospongia exigua 327. Xestospongia sapra 325, 326, 334, 339, 340, 341, 342, 343. Xestospongia sp. 310, 311, 327, 331, 332, 333, 335, 336, 340, 344, 345, 346, 347, 348, 349, 350, 351. Xestospongia vansoesti 352.

Index 3 Compound Organism Source Index

Xestospongia wiedenmayeri 1029, 1054, 1055. Xylocarpus moluccensis 714, 715, 716, 717, 719, 720, 721, 779, 780. Xylocarpus rumphii 718, 722.

439

Z Zoanthus sp. 498, 499, 766, 767, 769, 770, 771, 772, 772, 773. Zoanthus spp. 768.

Index 4 Compound Sampling Geographic Locality Index In this index, all geographic locations in HAMNP Volume 2 have been devided as 17 large areas: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

CHINA JAPAN RUSSIA KOREA WATERS R. O. KOREA ASIA AUSTRALIA OCEANIA EUROPE AFRICA USA NORTH AMERICA CARIBBEAN SEA SOUTH AMERICA PACIFIC OCEAN ATLANTIC OCEAN ANTARCTIC/ARCTIC

For all 166 compound sampling geographic locations, each of them has put into one large area, and then within the area, all related geographic places are listed in alphabetical order with the detail information in the texts of the “Handbook of Active Marine Natural Products Volume 2” and a number code sequence of the related compounds follows the detail information immediately. There are 846 related compounds with geographic information in HAMNP Volume 2. 1 CHINA China, China waters 754, 776, 777, 924, 925. China, Dalian coast, Bohai Sea 625, 672, 673, 674, 675, 676, 677, 678, 688. China, Dongsha Atoll, South China Sea 881, 882. China, Hainan 619, 621, 679, 680, 681, 684, 685, 698, 733, 734, 735, 736, 737, 738, 739, 740, 741, 752, 753, 756, 757, 758. China, Sanya Bay, Hainan 295, 308. China, Sanya, Hainan 724, 725, 726, 727, 859, 860, 861, 862, 1048, 1049, 1050. China, Weizhou I., Guangxi 313, 314, 320, 321. China, Wenchang, Hainan 937, 938. China, Xisha Is., South China Sea 9, 10, 11, 13, 206, 207, 208, 209, 213, 214, 221, 222, 223, 224, 236, 238, 846, 847, 850, 852, 911, 912, 913, 914.

China, Yalong Bay, Hainan 226, 227, 233. China, Zhanjiang, Guangdong, South China Sea 693, 694, 695. China, Zhoushan Is., Zhejiang 500. South China Sea, Nha Trang Gulf, South China Sea 626, 627, 628, 629, 630, 631. South China Sea, South China Sea 8, 239, 240, 570, 571, 956, 998, 999. South China Sea, Yongxing I., South China Sea, China 561. Taiwan, Green I. 60, 135, 136, 137, 139, 157. Taiwan, Southeastern Taiwan 134. Taiwan, Taitung County 289, 505, 509, 524, 526, 530, 539, 579, 580. Taiwan, Taiwan waters 17, 18, 19, 21, 28, 29, 53, 54, 55, 56, 57, 58, 59, 128, 129, 130, 131, 132, 133, 188, 305, 388, 998, 999, 1000.

Index 4 Compound Sampling Geographic Locality Index

2 JAPAN Japan, Ayamaru Cape, Amami Is. 498, 499. Japan, Ayamaru coast of Amami Is. 766, 769, 772. Japan, Japan waters 51, 105, 106, 107, 113, 119, 120, 121, 122, 123, 141, 149, 170, 204, 211, 212, 215, 216, 218, 223, 224, 225, 291, 391, 392, 393, 466, 501, 502, 503, 507, 508, 513, 515, 516, 521, 522, 527, 535, 536, 582, 583, 600, 605, 729, 730, 731, 732, 793. Japan, near Tonga 742, 743, 744, 759. Japan, Yakushima-Shinsone, Kagoshima 138. Okinawa, Ishigaki I. 303. Okinawa, Okinawa 7, 64, 65, 66, 67, 68, 69, 70, 194, 205, 217, 220, 226, 230, 334, 395, 396, 414, 415, 416, 417, 418, 443, 444, 517, 519, 554, 581, 620, 692, 745, 746, 747, 748, 749, 750, 751, 816, 817, 818, 819, 820, 947, 981, 982. Okinawa, Taketomijima I. 172, 177, 183, 190. 3 RUSSIA Kuril Is., near Kuril Is., Northwestern Pacific Ocean 302, 306. Kuril Is., near Paramushir I., among Kuril Is. 728. Sea of Japan, Russia Troitsa Bay, Sea of Japan 648, 649, 650, 651. Sea of Okhotsk, Russia Sakhalin Bay, Sea of Okhotsk 844. 4 KOREA WATERS Korea waters, 163, 164, 165, 166, 658, 659, 660, 661, 841, 842, 917, 918, 919, 920, 921, 969, 970, 971, 972. 5 R. O. KOREA Cheju I. Cheju I. 366, 369, 375, 376, 377, 378, 379. Gageo I. Gageo I. 44, 45, 46, 47, 48, 427, 428, 429, 430, 431, 595. R. O. Korea 568, 585, 596, 597. 6 ASIA Arabian Sea Vizhinjam coast, Arabian Sea 699, 700. Far Eastern 645, 646, 647. India Andhra Pradesh 716, 717, 719, 720.

441

India Godavari estuary, Andhra Pradesh 714, 715. India Grandi I., Goa 123, 162. India waters 193, 511, 521, 772, 944, 1012. Indian Ocean Andaman and Nicobar Is. 308. Indonesia 331. Indonesia Baubau Buton I. 941. Indonesia Pula Baranglompo I. 576. Indonesia Sangalaki 344, 345, 346, 347, 348, 349, 350, 351. Indonesia Sulawesi 557, 558, 559. Indo-Pacific Sea Indo-Pacific 601. Malaysia Kudat 755. Malaysia 322, 328, 329, 754, 884, 888, 899, 906, 908. Malaysia N. Borneo I., Sabah 171, 250. Maldives 541, 542, 543. Philippines Culasian Point Leyte 939, 940. Philippines Palawan I. 352. Philippines 140, 142, 219. Red Sea 175, 290, 291, 381, 420, 422, 456, 824, 907, 952, 953, 995, 996, 1020, 1021. Sea of Japan Peter, Great Bay, Russia 622, 623, 624, 637, 638, 641, 642, 643, 644, 652. Thailand 231, 234, 451, 452, 490. Thailand Kudee I. 718, 722. Thailand Phuket province, Southern Thailand 721, 779, 780. Thailand Similan Is., Andaman Sea 511, 529, 539, 544, 545, 581. Vietnam 602, 608. Vietnam Bay Canh I., Khanh Hoa 173, 174. 7 AUSTRALIA Australia 202, 296, 297, 361, 372, 446, 447, 448, 449, 450, 950, 988, 1010. Australia Bass Strait, Tasmania (State) 371. Australia Hunter I., Tasmania 821, 822, 823. Australia Kelso Reef, Queensland 62, 63, 108, 109, 115. Australia New South Wales Victoria 584. Great Barrier Reef, Australia Bowden Reef 180, 181, 189, 193, 194. Great Barrier Reef, 72, 73, 74, 76, 77, 78, 110, 111, 112, 114, 114, 116, 117, 118, 192, 218, 397, 399, 405, 424, 425, 426, 547, 832, 833, 879.

442

Index 4 Compound Sampling Geographic Locality Index

Great Barrier Reef, Australia north side of Pelorus I. 397, 399, 405, 424, 425, 426. Queensland 462, 464, 465, 793. Southern Australia off Southern Australia 927, 928. 8 OCEANIA Federated States of Micronesia Chuuk State 930, 934. Federated States of Micronesia Pohnpei I. 931. Federated States of Micronesia Truk I. Lagoon 838, 839. Fiji 217, 265, 266, 267, 268, 269, 325, 326, 327, 340, 966. Fiji Yanuca I. 804, 805, 806, 807, 808, 809, 810, 811, 812, 813. New Zealand 855, 856, 857, 943. New Zealand Hauraki Gulf 1019. Palau, Oceania 14, 440, 441, 442, 453, 454, 454, 458, 459, 796, 827, 830, 831, 884, 888, 899, 906, 908, 948, 949, 962. Palau, Oceania Northern Reef region 398, 433, 434. Papua New Guinea 389, 390, 420, 421, 423, 456, 457. Papua New Guinea Milne Bay 400. Papua New Guinea Sanaroa 389, 390. Solomon Is. 420, 421, 423, 456, 457, 552, 697, 967. Vanuatu 327, 340, 632, 633, 634, 635, 636. 9 EUROPE Adriatic Sea 572, 573, 575, 944, 955, 1010. Adriatic Sea Northern Adriatic Sea 367, 368, 574. Adriatic Sea, Italy Adriatic Sea 304. Black Sea 781. Germany 858. Gibraltar Strait 893, 894, 895, 896, 897, 898. Italy Bay of Naples 354, 461. Italy Naples 514. Italy Porto Cesareo, Lecce 873, 874. Mediterranean Sea 147, 150, 169, 176, 198, 263, 279, 437, 438, 508, 760, 783, 784, 1040. Mediterranean Sea Callejones, Ceuta 945, 987, 990. Mediterranean Sea Italy 848, 849. Spain 272, 385, 1004.

Spain Cádiz 1, 2, 6, 24, 201, 510, 540. Spain Canary Is. 615, 616, 1035. Spain La Caleta, Cadiz 356, 363, 384, 386. Spain Macaronesia in Canary Is. 603, 607. Spain off Canary Is. 604, 606, 612, 613. Spain Tarifa I., Cádiz 504, 506, 518, 532, 533, 534, 538. Spain Tenerife I., Canary Is. 770. 10 AFRICA Comoros Is. 14, 765. Comoros Is. Mayotte I., Madagascar Channel 307. Egypt Abu-Bakr, Red Sea 202. Eritrea Dahlak archipelago 435, 436. Kenya 152, 158. Morocco 973. Somalia 754. South Africa 127, 148, 153, 154, 155, 156, 159, 160, 463, 761, 762, 763, 764, 950, 1005. South Africa Sodwana Bay, Durban 246, 247, 248. 11 USA Alaska, USA 936. California, USA Oceanside 590, 591. Florida, USA 485, 486, 487, 488, 489. Florida, USA estuary, in Everglades 330. Florida, USA Florida Keys 210. Florida, USA Hillsboro Ledge 182. Guam, USA 226. Guam, USA Orote Peninsula 408, 409, 410, 411. Hawaii, USA 195, 196, 197, 686, 687, 704, 706, 708, 709, 710, 711, 712, 713, 869, 886, 886, 979, 1001, 1051, 1052, 1053. Maui, USA 864. Puerto Rico 887. Texas, USA Trinity Bay, Galveston 916. 12 NORTH AMERICA Barbados 198, 202. Canada Ansell Point, Howe Sound, British Columbia 567. Canada Ansell Pt., British Columbia 460, 460. Canada British Columbia 202. Costa Rica 556. Mexico 144. Mexico Quintana Roo 834, 835, 1023.

Index 4 Compound Sampling Geographic Locality Index

13 CARIBBEAN SEA Bahamas Caribbean Sea 403, 486, 487, 586, 592, 593, 1054, 1055. Bahamas Little San Salvador I. 875, 876. Bahamas off Bahamas 1003. Caribbean Sea 30, 185, 186, 204, 275, 401, 402, 467, 468, 469, 586, 587, 654, 655, 656, 657, 662, 868, 1027, 1028. Caribbean Sea West Indian Sea 100, 292, 298, 299, 300, 301, 323, 324. Dominica 964. Dominica Lauro Club Reef, Dominica, Caribbean 915. Jamaica 35, 36, 37, 38, 39, 40, 41, 42, 43, 1060. Jamaica off Jamaica 35, 36, 37, 38. Jamaica St Ann’s Bay 983, 984. 14 SOUTH AMERICA Argentina Argentine Patagonian coast 665, 666. Argentina Bridges I., Tierra del Fuego 690, 691. Columbia 100, 243, 264, 270, 271, 298, 299, 300, 301, 312, 323, 324. Colombia off San Andres I. 309. Colombia Old Providence I. 20. Colombia San Andres Archipelago 293, 294. Colombia Santa Marta Bay, Caribbean Sea 183, 276.

443

15 PACIFIC OCEAN East Pacific Ocean 253, 254, 255, 256, 256, 257, 257, 258, 259. New Caledoinia (Fr.) 359, 360, 380, 406, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 525, 594, 864, 880, 909, 954, 958, 974, 978, 1002, 1011, 1012. New Caledoinia (Fr.) New Caledonian coast 944, 994, 1008. Northern Pacific Ocean 639, 640. Pacific Ocean 1044. Pacific Ocean Tahiti 864. 16 ATLANTIC OCEAN Atlantic Ocean Mosteiros Sao Miguel I., Azores 889, 890, 891, 892. Bermuda 887. North Atlantic Ocean 663. South Atlantic Ocean South Atlantic site 15, 22. 17 ANTARCTIC/ARCTIC Antarctic 273, 274, 682, 683, 968, 1006, 1007. Antarctic King George I. 598, 599. Antarctica McMurdo Sound 598, 599. Arctic 664.

Index 5 Compound Pharmacological Activity Index In this index, a set of very formatted pharmacological activity codes have been used, specially for all types of cancer cells, please see “List of Cancer Cells Codes”. A special note is that the word “Cytotoxic” means in vitro anticancer activities, while the word “Antineoplastic” means in vivo anticancer activities. A A lead for inhibitors of tumour immune escape 352. Aantihelmintic, high activity against rodentpathogenic roundworm Nippostongylus brasiliensis 226. ACE inhibitor 374. Acetylcholine esterase inhibitor 1042. Acetylcholinesterase inhibitor 570, 571. Activator of cAMP signaling pathway, HEK-293 cells in absence of hormone binding 400, 460. Activator of HIF-1 322, 328, 329. Activator of PPARγ 969, 970, 971, 972. African sleeping sickness 389, 390. Aldose reductase inhibitor 374, 439. Algicide 49, 143, 178, 198, 202, 1039. Allelochemical 760. Allelopathic 255. Allelopathic, etiolated wheat coleoptiles bioassay 253, 254. Analgesic 946, 1043, 945, 79, 80, 81, 82, 101, 102, 103, 104, 767, 768, 853, 990, 419. Angiogenesis inhibitor 781. Anthelmintic 231, 1014. Anti-atherosclerosis 598, 1054. Antibacterial 140, 142, 244, 245, 265, 266, 267, 268, 269, 453, 484, 487, 863, 945. Antibacterial inactive, MRSA 320, 321, 810, 811, 812. Antibacterial inactive, Pseudomonas aeruginosa 320, 321. Antibacterial inactive, Pseudomonas fluorescens 320, 321. Antibacterial inactive, Staphylococcus epidermidis 320, 321. Antibacterial inactive, VREF 810, 812. Antibacterial, Aeromonas salmonisida 149, 170.

Antibacterial, Agrobacterium tumefaciens 973. Antibacterial, Bacillus cereus 989. Antibacterial, Bacillus megaterium 843, 1035. Antibacterial, Bacillus subtilis 51, 158, 226, 229, 327, 397, 399, 405, 424, 425, 426, 432, 451, 452, 454, 493, 495, 574, 776, 777, 855, 856, 857, 904, 943, 1025, 1041. Antibacterial, Bacillus subtilis, MMOA: isocitrate lyase inhibition 879, 942. Antibacterial, Clostridium spp. 776. Antibacterial, Corynebacterium spp. 776. Antibacterial, Enterococcus faecalis 92, 94, 79, 80, 81, 82, 89, 83. Antibacterial, Escherichia coli 114, 397, 399, 405, 424, 500, 776, 777, 973, 989, 1035. Antibacterial, Escherichia coli ATCC 158. Antibacterial, gram-positive and -negative bacteria 23, 26, 27. Antibacterial, gram-positive bacteria 407, 775, 927, 928, 942. Antibacterial, gram-positive bacterium Bacillus subtilis 592. Antibacterial, Halomonas aquamarina 848, 849, 851. Antibacterial, inhibits growth of marine bacteria 278. Antibacterial, Micrococcus luteus 397, 399, 405, 424, 574, 1041. Antibacterial, Micrococcus lysoleikticus 776, 777. Antibacterial, Micrococcus sp. 962. Antibacterial, Micrococcus spp. 776. Antibacterial, MRSA 314, 590, 591, 802, 803, 804, 805, 806, 807, 808, 809, 813, 937, 938. Antibacterial, MRSA, along with significant feeding deterrence against sea star Odontaster validus 968.

Index 5 Compound Pharmacological Activity Index

Antibacterial, MRSA, synergism with Antibiotic oxacillin 867. Antibacterial, MSSA, along with significant feeding deterrence against sea star Odontaster validus 968. Antibacterial, Myobacterium spp. 776. Antibacterial, Polaribacter irgensii 848, 849, 851. Antibacterial, Pseudoalteromonas elyakovii 848, 849, 851. Antibacterial, Pseudomonas aeruginosa 314. Antibacterial, Pseudomonas fluorescens 313, 314. Antibacterial, Pseudomonas spp 776. Antibacterial, Roseobacter litoralis 848, 849, 851. Antibacterial, Salmonella sp. 171. Antibacterial, Salmonella spp 776. Antibacterial, Sarcina lutea 751. Antibacterial, Shewanella putrefaciens 848, 849, 851. Antibacterial, Shigella spp 776. Antibacterial, Staphylococcus aureus 79, 80, 81, 82, 83, 89, 92, 94, 149, 170, 171, 226, 229, 250, 327, 408, 409, 410, 411, 419, 425, 426, 432, 451, 452, 454, 542, 938, 943, 961, 962, 974, 1041. Antibacterial, Staphylococcus epidermidis 313, 314, 959, 989. Antibacterial, Staphylococcus sp. 171, 250. Antibacterial, Staphylococcus spp. 776. Antibacterial, Staphyrococcus aureus 1025, 904. Antibacterial, Streptococcus pyogenes 79, 80, 81, 82, 83, 89. Antibacterial, Streptococcus pyogenes, selective 92, 94. Antibacterial, Streptococcus spp 776. Antibacterial, Streptomyces pyogenes 419. Antibacterial, Streptomyces sp. 85E 440, 441, 442. Antibacterial, Vibrio carchariae 848, 849, 851. Antibacterial, Vibrio cholera 250. Antibacterial, Vibrio harveyi 114, 848, 849, 851. Antibacterial, Vibrio natriegens 848, 849, 851. Antibacterial, Vibrio proteolyticus 848, 849, 851. Antibacterial, VREF 802, 803, 811, 813.

445

Antibacterial, VREF, along with significant feeding deterrence against sea star Odontaster validus 968. Antibiotic 219, 325, 327, 365, 491, 841. Anticonvulsant and antiepileptic agent 192. antidementia 519. Antifeedant 52, 202, 262, 467, 468, 469, 523, 587, 714, 715, 716, 717, 719, 720, 798, 870, 1028. Antifeedant, ecologically relevant reef fish Thalassoma bifasciatum 662. Antifeedant, fish 197, 278, 508, 525, 782, 1026, 1027. Antifeedant, fish Carassius auratus 586. Antifeedant, fish Carassius auratus high feeding deterrence 403. Antifeedant, fishes 195, 196. Antifeedant, inhibits feeding in omnivorous fish Tilapia mossambica 151. Antifeedant, marine herbivore 195, 196, 197. Antifeedant, second-instar larvae of diamondback moth Plutella xylostella 724, 725, 726, 727. Antifeedant, urchins 195, 196, 197. Antifoulant 236, 237, 276, 387, 793. Antifoulant, inhibits cyprid larval settlement and metamorphosis of barnacle Balanus amphitrite 223, 224, 225, 226, 228. Antifoulant, inhibits settlement and metamorphosis of barnacle larvae 204, 211, 212, 215, 216. Antifungal 637, 641, 699, 1061. Antifungal inactive, ABRCA 802, 803, 810, 811, 812, 901. Antifungal inactive, Candida albicans SC5314 688. Antifungal inactive, Candida tropicalis 688. Antifungal inactive, Cryptococcus neoformans BLS108 688. Antifungal, ABRCA 813. Antifungal, Absidia glauca 330. Antifungal, Aspergillus fumigatus 619, 621, 679, 680, 684, 685. Antifungal, Aspergillus fumigatus 0504656 625, 672, 673, 674, 676, 677, 678, 688. Antifungal, Aspergillus niger 926. Antifungal, Aspergillus oryzae 926, 1002. Antifungal, Botrytis cinerea 973. Antifungal, broad spectrum 675.

446

Index 5 Compound Pharmacological Activity Index

Antifungal, Candida albicans 226, 229, 619, 621, 679, 680, 684, 685, 942, 943, 1002, 1003, 1020, 1021. Antifungal, Candida albicans SC5314 625, 672, 673, 674, 676, 677, 678. Antifungal, Candida krusei 619, 621, 679, 680, 684, 685. Antifungal, Candida tropicalis 625, 672, 673, 674, 676, 677, 678, 619, 621, 679, 680, 684, 685. Antifungal, Cladosporium cucumerinum 690, 691. Antifungal, Cryptococcus neoformans 751, 619, 621, 679, 680, 684, 685. Antifungal, Cryptococcus neoformans BLS108 625, 672, 673, 674, 676, 677, 678. Antifungal, especially Penicillium notatum and Aspergillus oryzae 1003. Antifungal, Fusarium oxysporum f. sp. lycopersici 973. Antifungal, inhibits growth of marine fungi 278. Antifungal, Microbotryum violacea 843. Antifungal, Microsporum gypseum 31388 688, 625, 672, 673, 674, 676, 677, 678. Antifungal, Mortierella romannicus 220. Antifungal, Mucor miehei 330. Antifungal, Mycotypha microspora 843. Antifungal, oomycete fungi 61. Antifungal, Paecilomyces variotii 330. Antifungal, pathogenic fungus Cladosporium cucumerinum 689. Antifungal, Penicillium chrysogenum 220. Antifungal, Penicillium islandicum 330. Antifungal, Penicillium notatum 330, 885, 1002. Antifungal, phytopathogenic fungus Cladosporium cucumerinum 180, 184, 191, 665, 666. Antifungal, RS321 Inhibitor 4, 5. Antifungal, Saccharomyces cerevisiae 885, 926, 1002. Antifungal, Sclerotinia libertiana 926. Antifungal, Sporothrix schenckii 667. Antifungal, Trichophyton mentagrophytes 667, 749, 750, 751, 855, 856, 857, 885, 1002. Antifungal, Trichophyton rubrum 619, 621, 679, 680, 684, 685.

Antifungal, Trichophyton rubrum 0501124 625, 672, 673, 674, 676, 677, 678, 688. Antifungal, Ustilago violacea 404. Antifungal, Verticillium alboatrum 973. Antihelmintic, high activity against rodentpathogenic roundworm Nippostongylus brasiliensis 232, 234, 235. Anti-HIV 775, 1005, 853, 929, 935. Anti-HIV-1 43. Anti-HIV-1 inactive 35, 37, 38, 42. Anti-HIV-1, 96USHIPS7 strain 802. Anti-HIV-1, but not efficient in clinical treatment of patients with AIDS 853, 854. Anti-HIV-1, HIV-1 36. Anti-HIV-1, HIV-1 replication C8166 258. Anti-HIV-1, UG/92/029 strain 802. Anti-inflammatory 67, 79, 80, 81, 82, 84, 85, 86, 87, 88, 89, 90, 101, 102, 103, 104, 182, 186, 187, 275, 359, 360, 372, 382, 383, 403, 406, 413, 419, 454, 486, 505, 512, 524, 528, 536, 551, 552, 553, 554, 555, 560, 572, 767, 768, 771, 772, 773, 853, 854, 1006, 1007. Anti-inflammatory, diabetic KK-Ay mice model in vivo and in vitro 793. Anti-inflammatory, hmn neutrophils in response to fMLP/CB, elastase release inhibition assay 129, 130, 131, 132, 133. Anti-inflammatory, hmn neutrophils in response to fMLP/CB, superoxide anion generation assay 129, 130, 131, 132, 133. Anti-inflammatory, in vivo 550. Anti-inflammatory, inhibits secretory PLA2 437, 438. Anti-inflammatory, mouse peritoneal macrophage, selectively inhibits synthesis of leukotrienes LTB4 and LTC4, but not PGE2 185. Anti-inflammatory, NO and TNF-R production inhibitor 842. Anti-inflammatory, NO production inhibitor, LPS-activated murine macrophage J774.A1 cells 718, 722. Anti-inflammatory, platelet aggregation inhibitor 548. Anti-inflammatory, RAW264.7 macrophage-like cells and 3T3-F442A adipocytes, reduction of iNOS, COX-2, MCP-1 and IL-6 mRNA over-expression 794.

Index 5 Compound Pharmacological Activity Index

Anti-inflammatory, release effect on rat microglia stimulated by PMA: O2•−, TXB2, LDH 91, 93, 96, 97, 98, 99, 241, 242. Anti-inflammatory, TPA-induced mouse ear edema assay 183, 276. Anti-inflammatory, with very low acute toxicity in mice, appears to act by a novel mechanism of pharmacological action 83. Antileishmanial, Leishmania amazonesis 138. Antileukemia, in vitro and in vivo 853, 854. Antimalarial 235, 265, 266, 267, 268, 269, 869. Antimalarial, CRPF FcB1 974. Antimalarial, CRPF PFB 974. Antimalarial, CSPF F32 974, 1002. Antimalarial, Plasmodium falciparum 490. Antimalarial, Plasmodium falciparum 3D7 804, 805, 806, 807, 808, 809. Antimalarial, Plasmodium falciparum D6 420, 456, 991. Antimalarial, Plasmodium falciparum W2 420, 456, 991. Antimicrobial 95, 99, 151, 198, 199, 200, 277, 361, 382, 383, 422, 463, 471, 531, 572, 868, 975, 1024, 1059. Antimicrobial inhibition halos 1001. Antimicrobial, wide range 795. Antimitotic 198, 202, 880, 1039. Antimutagenic 795, 854. Antimutagenic, with inhibiting effect on benzo [a]pyrene monooxygenase 853. Antimycobacterial 244, 245. Antineoplastic, in vivo 270, 292, 795, 842. Antineoplastic, in vivo, arrests proliferation of various cell lines, including those that have been transformed by oncogenic PTKs 327. Antineoplastic, in vivo, especially melanoma and ovarian tumours, use limited by low solubility 61. Antineoplastic, in vivo, L1210 814. Antineoplastic, in vivo, life-prolonging effect on P388 leukemia implanted mice 535. Antineoplastic, in vivo, P388 541, 542, 543, 1003. Antineuroinflammatory 305. Anti-obesity and anti-diabetic, high fat-diet mice, reduction of body and adipose tissue weight and reduction of lipogenesis and promotion of β-oxidation 793.

447

Anti-obesity and anti-diabetic, high-fat diet mice model, suppression of adipose tissue and body weight gain and reduction of MCP-1 mRNA expressions 793. Anti-obesity, diabetic KK-Ay mice model, suppression of white adipose tissue weight gain 793. Anti-obesity, through UCP1 expression in white adipose tissues 793. Antioxidant 785, 787, 795, 796, 800, 834, 835, 917, 918, 919, 921, 941, 1023. Antioxidant, ABTS∙+ assay 893, 894, 895, 896, 897, 898. Antioxidant, DPPH radical scavenger 838, 889, 890, 926, 1004. Antioxidant, hmn neutrophils, iInhibits generation of superoxide anion 1000. Antioxidant, hydroxyl and superoxide radical scavenger 793. Antioxidant, identical to that of α-Tocopherol 1044. Antioxidant, oxygen radical absorbance 845. Antioxidant, peroxy radical scavenger 173, 174. Antioxidant, radical H2O2 scavenging 786. Antioxidant, radical HO• scavenging 786. Antioxidant, radical NO2 scavenger 789. Antioxidant, radical O2•− scavenging 786. Antioxidant, radical ONOO− scavenger 789. Antioxidant, radical ONOOH scavenger 789. Antioxidant, rbt cell neutrophils 148. Antioxidant, reactive chlorous species RCS quencher [HOCl] 786. Antioxidant, reactive nitrogen species RNS quencher [NO•, ONOO−] 786. Antioxidant, reactive oxygen species 1O2 quencher 786, 788, 789. Antioxidant, reactive oxygen species 1O2 quencher radicals scavenging, O2•−, HO•, ONOO−, HOCl, DPPH•, etc 793. Antioxidant, reactive oxygen species ROS quencher [NO•, LOOH, ONOO−, HOCl] 786. Antioxidant, scavenger 303. Antioxidant, superoxide anion ∙O2– scavenger 155, 156. Antioxidant, superoxide anion scavenger, in both rbt and hmn cell neutrophils 153, 154.

448

Index 5 Compound Pharmacological Activity Index

Antiparasitic 492. Antiplasmodial inactive, Plasmodium falciparum D6 218. Antiplasmodial inactive, Plasmodium falciparum W2 218. Antiplasmodial, CRPF W2 293. Antiplasmodial, DRPF 1019. Antiplasmodial, FM3C 205, 217, 220, 226. Antiplasmodial, Plasmodium falciparum 20, 138, 205, 217, 220, 226, 230, 292, 309, 312, 810, 811, 812, 813. Antiplasmodial, Plasmodium falciparum D6 72, 73, 74, 75, 76, 77, 78, 110, 111, 112, 114, 115, 116, 117, 118. Antiplasmodial, Plasmodium falciparum FCR3F86 62, 63, 108, 109, 115. Antiplasmodial, Plasmodium falciparum K1 843. Antiplasmodial, Plasmodium falciparum NF 54 843. Antiplasmodial, Plasmodium falciparum W2 72, 73, 74, 75, 76, 77, 78, 110, 111, 112, 114, 115, 116, 117, 118. Antiproliferation, MCF7 484. Antiproliferative 1006, 1007, 1060. Antiproliferative, 1, 4- benzoquinone moiety demonstrated as essential for activity 884, 888, 899, 906, 908. Antiproliferative, cultures of mouse fibroblasts and activity was linked to the presence of ortho-hydroquinone moiety 877, 878. Antiproliferative, KB 581. Antipsoriatic 425, 426, 419. Antispasmodic 407. Antitoxoplasma, Toxoplasma gondii without significant toxicity 420, 456. Antitrypanosomal, Trypanosoma brucei 389, 390. Antitrypanosomal, Trypanosoma congolense 138. Antituberculosis 271, 298, 299, 300, 301, 323. Antituberculosis inactive, Mycobacterium tuberculosis 810, 811, 812. Antituberculosis inactive, Mycobacterium tuberculosis H37Ra 490. Antituberculosis Mycobacterium tuberculosis 38. Antituberculosis Mycobacterium tuberculosis H37Rv 524.

Antituberculosis, mPTPB inhibitor 569. Antituberculosis, Mycobacterium tuberculosis 35, 36, 37, 293, 294, 813. Antituberculosis, Mycobacterium tuberculosis H37Rv 71, 100, 243, 264, 324, 825, 883, 885, 886, 976, 977, 985, 986, 991, 1003, 1047. Antiulcer 723, 781. Antiviral 252, 618. Antiviral inactive, HBV 35, 36. Antiviral, A59 hepatitis virus 251. Antiviral, BHK/VSV 991. Antiviral, CV-1/MSV-1 991. Antiviral, HBV 37. Antiviral, Herpes simplex virus HSV-1 451, 452. Antiviral, HSV virus 840, 902. Antiviral, HSV-1 64, 65, 251, 381, 420, 682, 683. Antiviral, HSV-2 885. Antiviral, influenza and adenovirus viruses 23, 26, 27. Antiviral, influenza PR-8 1029. Antiviral, influenza virus A H1N1 846, 847, 850, 852. Antiviral, murine corona virus A59 261. Antiviral, Mv 1 Lu/HSV I1 864, 991. Antiviral, potent irreversible inhibitor of Rous sarcoma virus 325. Antiviral, VSV cells in BHK 668, 669, 670. Antiviral, Vesicular stomatitis virus VSV 451, 452. ATP inhibitor 946. ATPase of kinesins inhibitor 828, 829. B BACE1, a central role in etiology of Alzheimer’s disease 346. BACE1 aspartic protease inhibitor 344, 345, 346, 347, 348, 349, 350, 351. Bee venom inhibitor 537. Binds to neuropeptide Y receptor 946, 954, 958, 978, 994, 1011, 1012. Bradycardia activity, isolated gpg heart 10. C Ca2+ deposition enhancer, in osteoblasts 595. Ca2+ influx activator 656, 657. Ca2+-ATPase activator 394. Calcium channel blocker 12.

Index 5 Compound Pharmacological Activity Index

Calcium channel blocker, rbt, isolated smooth muscle 9, 10, 11. Calcium homeostasis modifier 588. Cardiotonic 325, 340. Cardiotonic activity 327. Cdc25 phosphatase inhibitor 880. CDK/cyclin D1 inhibitor 1022. Cell cycle arrest, MCF7, through activation of MAPK signaling pathways 498. Cell division inhibitor 50. Cell division inhibitor, fertilized ascidian eggs 278. Cell division inhibitor, fertilized sea urchin egg assay 1034. Cell division inhibitor, fertilized starfish eggs 355, 370. Cell division inhibitor, starfish embryos 373. CETP inhibitor 598, 1054, 1055. CETP inhibitor, used to mediate transfer of cholesteryl ester and triglyceride between high and low-density lipoproteins 599. Chain-breaking Antioxidant 786. CMV protease inhibitor 701, 707. Cobra venom PLA2 inhibitor 380. Coronary vasodilator 395, 815. COX-2 expression regulator 403. Cyclooxygenase-2 inhibitor, ten-fold stronger than reference compound indomethacine 1055. Cytostatic, increase in number of eggs in fourcell stage blastomere 844. Cytotoxic 15, 22, 31, 50, 249, 265, 266, 267, 268, 269, 277, 278, 307, 373, 382, 383, 419, 422, 463, 484, 525, 561, 576, 609, 610, 611, 622, 623, 624, 637, 644, 648, 649, 650, 651, 693, 694, 695, 696, 699, 761, 772, 797, 798, 838, 872, 873, 874, 881, 882, 911, 912, 913, 914, 922, 923, 973, 1039. Cytotoxic inactive, 786-0 421. Cytotoxic inactive, A2780 304, 733, 734, 738. Cytotoxic inactive, A2780CisR 304. Cytotoxic inactive, A375 295, 308, 993. Cytotoxic inactive, A549 17, 21, 56, 58, 206, 207, 208, 209, 221, 222, 238, 253, 259, 295, 308, 314, 315, 318, 428, 733, 734, 735, 736, 737, 738, 739, 740, 741, 752, 753, 764, 864, 983, 984. Cytotoxic inactive, A549/ATCC 421.

449

Cytotoxic inactive, ascite cell of EAC 645, 646, 647. Cytotoxic inactive, AsPC-1 984. Cytotoxic inactive, B16 993. Cytotoxic inactive, B16-F-10 936. Cytotoxic inactive, Bel7402 314, 317, 319, 733, 734, 735, 736, 737, 738, 739, 740, 741, 752. Cytotoxic inactive, BGC823 295, 308, 733, 734, 737, 738, 739, 740, 741, 752, 753, 758. Cytotoxic inactive, BT-549 421. Cytotoxic inactive, Calu 210. Cytotoxic inactive, CHO-K1 823, 900. Cytotoxic inactive, CV-1 864. Cytotoxic inactive, DLD-1 509, 539, 579, 580. Cytotoxic inactive, EAC 9, 10, 239, 240. Cytotoxic inactive, H460 821, 823, 900. Cytotoxic inactive, H69AR 511, 539, 544, 581. Cytotoxic inactive, HCT8 295, 308, 733, 734, 737, 738, 739, 740, 741, 752, 753, 758. Cytotoxic inactive, HCT116 208, 209, 213, 214, 222, 224, 236, 238, 509, 539, 579, 580, 1051, 1052, 1053. Cytotoxic inactive, HeLa 206, 207, 208, 209, 222, 238, 539, 544, 890, 892, 993. Cytotoxic inactive, HeLa, lag phase 891. Cytotoxic inactive, HepA 239, 240. Cytotoxic inactive, HepG2 295, 308. Cytotoxic inactive, HL60 295, 308, 330, 420. Cytotoxic inactive, HT29 17, 21, 56, 57, 58, 59, 428, 429, 763, 764, 821, 823, 864, 900, 936. Cytotoxic inactive, HuCCA-1 511, 529, 539, 544, 545. Cytotoxic inactive, IGROV1 420. Cytotoxic inactive, K562 304, 509, 539, 579, 580, 658, 659, 660, 661. Cytotoxic inactive, KB 72, 73, 74, 76, 77, 110, 111, 115, 117, 169, 218, 263, 279, 516, 527, 539, 544, 745, 746, 747, 748, 816, 819, 864. Cytotoxic inactive, KM12 420, 421. Cytotoxic inactive, KYSE70 1005. Cytotoxic inactive, KYSE180 1005. Cytotoxic inactive, KYSE520 1005. Cytotoxic inactive, LoVo 864. Cytotoxic inactive, MALME-3M 458, 459. Cytotoxic inactive, MCF7 300, 458, 459, 823, 900.

450

Index 5 Compound Pharmacological Activity Index

Cytotoxic inactive, MDA-MB-231 206, 207, 208, 209, 213, 236, 238, 544. Cytotoxic inactive, MEL28 763, 764. Cytotoxic inactive, Molt4 314, 315, 318, 420, 421. Cytotoxic inactive, mouse spleen lymphocytes 645, 646. Cytotoxic inactive, NCI-ADR-Res 983, 984. Cytotoxic inactive, NCI-H460 300. Cytotoxic inactive, NSCLC-N6 169. Cytotoxic inactive, P388 58, 59, 169, 356, 384, 443, 709, 710, 712, 763, 764, 864, 960, 1014, 1015, 1016, 1029. Cytotoxic inactive, P388/Dox 169, 263, 279. Cytotoxic inactive, panel of 11 tumour cell lines 901. Cytotoxic inactive, QGY-7701 206, 207, 208, 209, 222, 238. Cytotoxic inactive, S180A 239, 240. Cytotoxic inactive, SF268 300, 821, 900. Cytotoxic inactive, SK-MEL-2 375. Cytotoxic inactive, T47D 509, 529, 539, 544, 545, 579, 580. Cytotoxic inactive, Vero 381, 890, 892. Cytotoxic inactive, Vero, lag phase 891. Cytotoxic inactive, WHCO1 1005. Cytotoxic inactive, WHCO5 1005. Cytotoxic inactive, WHCO6 1005. Cytotoxic, 36 hmn tumour cell lines 915. Cytotoxic, 786-0 456, 457. Cytotoxic, 786-0, GI50 > 5.0 μmol/L 423. Cytotoxic, A2780 735, 736, 737, 739, 740, 741, 752, 753, 758. Cytotoxic, A431 172, 177, 183, 190. Cytotoxic, A498 430, 431. Cytotoxic, A549 1, 2, 6, 18, 19, 24, 28, 29, 44, 45, 46, 47, 48, 53, 54, 55, 57, 59, 127, 159, 160, 188, 201, 213, 214, 223, 224, 227, 233, 236, 272, 316, 317, 319, 366, 369, 375, 376, 377, 378, 379, 427, 429, 451, 452, 504, 506, 510, 518, 532, 533, 534, 538, 540, 603, 604, 606, 607, 608, 612, 613, 615, 616, 639, 640, 664, 668, 669, 670, 698, 758, 762, 763, 871, 925, 947, 956, 960, 979, 991, 998, 999, 1002, 1003, 1003, 1025. Cytotoxic, A549/ATCC: CCL8 381. Cytotoxic, A549, mixture with Bilosespene A 436.

Cytotoxic, A549, mixture with Bilosespene B 435. Cytotoxic, A549/ATCC 456, 457. Cytotoxic, A549/ATCC, GI50 > 5.0 μmol/L 423. Cytotoxic, ACHN 496. Cytotoxic, anti-oesophageal cancers 1005. Cytotoxic, ascite cells of EAC 638, 641, 642, 643. Cytotoxic, AsPC-1 983. Cytotoxic, B16 668, 669. Cytotoxic, Bel7402 315, 316, 318, 753, 758. Cytotoxic, BGC823 735, 736. Cytotoxic, brine shrimp Artemia salina 903. Cytotoxic, BT-549 456, 457. Cytotoxic, BXF-1218L, selective 915. Cytotoxic, BXPC3 754. Cytotoxic, CAKI-1 292. Cytotoxic, CCRF-CEM 289. Cytotoxic, CHO-K1 793, 821, 822. Cytotoxic, CML K562 945, 987, 990. Cytotoxic, CV-1 991, 1002. Cytotoxic, differentiation-inducing activity to K562 cells into erythroblast 905, 1025. Cytotoxic, DLD-1 289, 505, 524, 530, 581, 983, 984. Cytotoxic, Doay 134. Cytotoxic, EAC 8, 11, 13. Cytotoxic, EKVX 292. Cytotoxic, four HTCLs 526. Cytotoxic, GM7373 14. Cytotoxic, H460 181, 189, 193, 194, 793, 822. Cytotoxic, HCT8 735, 736, 1003. Cytotoxic, HCT15 366, 369, 375, 376, 377, 378, 379. Cytotoxic, HCT116 30, 206, 207, 221, 223, 496, 505, 524, 530, 581, 592, 593, 866, 966. Cytotoxic, HeLa 213, 214, 221, 223, 224, 236, 256, 257, 258, 511, 529, 545, 581, 668, 669, 756, 757, 889, 962. Cytotoxic, HeLa, lag phase 889, 890, 891, 892. Cytotoxic, HeLa-S3 600, 601. Cytotoxic, Hep2 134. Cytotoxic, HepA 903. Cytotoxic, HepG2 128, 427, 428, 429, 962. Cytotoxic, HEY 778. Cytotoxic, HL60 314, 315, 316, 317, 318, 319, 421, 456, 698, 753, 756, 757, 924, 925, 962.

Index 5 Compound Pharmacological Activity Index

Cytotoxic, HL60(KB) 457. Cytotoxic, HL60(KB), GI50 > 5.0 μmol/L 423. Cytotoxic, hmn breast tumour cells 964. Cytotoxic, hmn colon tumour cell lines 577, 578, 964. Cytotoxic, hmn thyroid carcinoma 520. Cytotoxic, HOP-18 496. Cytotoxic, HT29 1, 2, 6, 18, 19, 24, 28, 29, 53, 54, 55, 127, 135, 136, 137, 139, 157, 159, 160, 201, 272, 427, 451, 452, 504, 506, 510, 518, 532, 533, 534, 538, 540, 603, 604, 606, 607, 608, 612, 613, 615, 616, 639, 640, 664, 762, 793, 822, 871, 947, 979, 991, 1002, 1003. Cytotoxic, HT29 ATCC: HTB38 381. Cytotoxic, HT29, mixture with Bilosespene A 436. Cytotoxic, HT29, mixture with Bilosespene B 435. Cytotoxic, HuCCA-1 581. Cytotoxic, IGROV1 421, 423, 456, 457. Cytotoxic, J774 14. Cytotoxic, K462 917, 918, 919, 920, 921. Cytotoxic, K562 44, 45, 46, 47, 48, 124, 125, 126, 163, 164, 165, 166, 167, 168, 391, 505, 524, 530, 581, 837. Cytotoxic, KB 23, 26, 27, 75, 78, 105, 106, 107, 112, 113, 114, 116, 118, 147, 150, 380, 466, 501, 503, 511, 515, 529, 545, 581, 582, 583, 614, 749, 750, 751, 817, 818, 820, 885, 903, 909, 974, 991, 997, 1002. Cytotoxic, KB16 956, 998, 999, 1025. Cytotoxic, KM12 456, 457. Cytotoxic, KM12, GI50 > 5.0 μmol/L 423. Cytotoxic, L1210 105, 106, 107, 113, 391, 396, 414, 415, 416, 417, 418, 466, 501, 503, 515, 516, 527, 582, 583, 745, 746, 747, 748, 749, 750, 751, 816, 817, 818, 819, 820, 997, 1024. Cytotoxic, L1210, very potent 508. Cytotoxic, L5178Y 304. Cytotoxic, LNCaP 210. Cytotoxic, LoVo 991, 1002. Cytotoxic, LOX-IMVI 421, 457. Cytotoxic, MALME-3M 454. Cytotoxic, MALME-3M, mixture with 13E-29Hydroxystelliferin A 742.

451

Cytotoxic, MALME-3M, mixture with 13E-29Hydroxystelliferin E 743. Cytotoxic, MALME-3M, mixture with 13E-3-epi29-Hydroxystelliferin E 744. Cytotoxic, MALME-3M, mixture with 13EStelliferin G 759. Cytotoxic, MCF7 134, 181, 189, 193, 194, 253, 259, 324, 454, 754, 793, 821, 822, 962, 1003. Cytotoxic, MCF12 1005. Cytotoxic, MDA-MB-231 61, 214, 221, 222, 223, 224, 496, 511, 529, 539, 545, 581. Cytotoxic, MEL28 1, 2, 6, 24, 127, 159, 160, 201, 272, 504, 506, 518, 532, 533, 534, 538, 603, 604, 606, 607, 612, 613, 615, 616, 639, 640, 664, 762, 871, 947. Cytotoxic, MEL28, mixture with Bilosespene A 436. Cytotoxic, MEL28, mixture with Bilosespene B 435. Cytotoxic, MKN1 535. Cytotoxic, MKN7 535. Cytotoxic, MKN74 535. Cytotoxic, Molt4 316, 317, 319, 391, 456, 457, 1000. Cytotoxic, Molt4, GI50 > 5.0 μmol/L 423. Cytotoxic, Molt4, mixture with 13E-29Hydroxystelliferin A 742. Cytotoxic, Molt4, mixture with 13E-29Hydroxystelliferin E 743. Cytotoxic, Molt4, mixture with 13E-3-epi-29Hydroxystelliferin E 744. Cytotoxic, Molt4, mixture with 13E-Stelliferin G 759. Cytotoxic, mouse spleen lymphocytes 638, 641, 642, 643, 647. Cytotoxic, murine hepatoma cells 992. Cytotoxic, mus J774 monocyte-macro-phage 654, 655. Cytotoxic, NCI-H460 324, 496, 962. Cytotoxic, neoplastic cell lines analyzed 1001. Cytotoxic, neuroblastoma cell line 494, 497. Cytotoxic, NIH3T3 61. Cytotoxic, NMuMG 61. Cytotoxic, non-small cell lung tumour cells 916. Cytotoxic, NSCLC 632, 633, 634, 635, 636.

452

Index 5 Compound Pharmacological Activity Index

Cytotoxic, NSCLC-N6 147, 150, 263, 279, 470, 471, 472, 473, 474, 475, 476, 477, 478, 594. Cytotoxic, P388 1, 2, 6, 14, 17, 18, 19, 21, 24, 28, 29, 33, 34, 53, 54, 55, 56, 57, 66, 67, 68, 69, 70, 127, 135, 136, 137, 139, 147, 150, 157, 159, 160, 175, 188, 201, 220, 246, 247, 248, 263, 272, 279, 290, 291, 296, 297, 363, 444, 451, 452, 471, 498, 499, 502, 504, 506, 507, 510, 511, 511, 513, 513, 518, 521, 522, 532, 533, 534, 535, 535, 538, 540, 602, 603, 604, 606, 607, 612, 613, 615, 616, 617, 639, 640, 654, 655, 664, 668, 669, 670, 686, 687, 704, 706, 708, 711, 713, 729, 730, 731, 732, 754, 755, 762, 765, 766, 769, 781, 824, 837, 839, 855, 856, 857, 871, 907, 947, 953, 956, 957, 979, 991, 998, 999, 1002, 1003, 1017, 1018, 1025, 496. Cytotoxic, P388 ATCC: CCL46 381. Cytotoxic, P388, mixture with Bilosespene A 436. Cytotoxic, P388, mixture with Bilosespene B 435. Cytotoxic, P388/ADR 496. Cytotoxic, P388/Dox 147, 150. Cytotoxic, PANC1 983, 984. Cytotoxic, panel of 6 cell lines, moderate 858. Cytotoxic, panel of 11 tumour cell lines 802, 803. Cytotoxic, panel of 12 tumour cell lines, mean IC50 = 16 μmol/L 811, 813. Cytotoxic, panel of 12 tumour cell lines, mean IC50 = 19 μmol/L 810. Cytotoxic, panel of 12 tumour cell lines, mean IC50 = 24 μmol/L 812. Cytotoxic, panel of hmn tumour cell lines, moderate 681. Cytotoxic, PC3M, selective 915. Cytotoxic, QGY-7701 213, 214, 221, 223, 224, 236. Cytotoxic, RB 7. Cytotoxic, SCHABEL 504, 506, 518, 532, 533, 534, 538, 639, 640, 664. Cytotoxic, sea urchin Strongylocentrotus eggs 1034. Cytotoxic, SF268 181, 189, 193, 194, 324, 793, 822, 823, 962.

Cytotoxic, SK-MEL-2 366, 369, 376, 377, 378, 379. Cytotoxic, SK-OV-3 366, 369, 375, 376, 377, 378, 379. Cytotoxic, strong 626, 627, 628, 629, 630, 631. Cytotoxic, T47D 496, 505, 511, 524, 530, 539, 581, 581, 1000. Cytotoxic, topoII 991. Cytotoxic, tumour tissues obtained from patients undergoing surgical resections 35, 37, 38, 39, 40, 41. Cytotoxic, U2OS 61. Cytotoxic, U373 778. Cytotoxic, Vero 420, 456, 889, 991. Cytotoxic, Vero, lag phase 891. Cytotoxic, weak 652. Cytotoxic, WEHI-164 14, 654, 655. Cytotoxic, WiDr 134. Cytotoxic, WMF 7. Cytotoxic, XF498 366, 369, 375, 376, 377, 378, 379. Cytotoxicity studies carried out suggest bolinaquinone acts by interfering with or damaging DNA 866. D Defensive agent 273, 274. Degranulation inhibitor 83. Differential Cytotoxicity, softagar assay, zone differential of 250 units is expected for “selectiveactivity”, M17-L1210 420, 421, 456, 457. Differential Cytotoxicity, softagar assay, zone differential of 250 units is expected for “selectiveactivity”, C38-L1210 456, 421. DNA polymerase inhibitor 824, 952. DNA topoisomerase I inhibitor 327, 339, 341, 342, 343. Down-regulation of pro-inflammatory cytokines expressions, 793. E EBV activation inhibitor 790, 791, 792. Effect on cell cycle progression and apoptosis, A2780 802. Elastase release inhibitor 60. Elastase release inhibitor, hmn neutrophils 1000.

Index 5 Compound Pharmacological Activity Index

Elastase stimulant, used in cosmetic antiwrinkle creams 79. Enhances production of antibody 785, 787. Enhances respiration and decreases mitochondrial membrane potential 329. Enzyme inhibitor 1003. Extracellular antimicrobial 801. F Folate biosynthesis inhibitor of bacteria 232, 234. For significant activity ED50 ≤ 4.0 μg/mL is required 53. G Glycerol-3-phosphate dehydrogenase inhibitor 842. Growth and gporulation inhibitor, Streptomyces sp. 85E 440, 441, 442. H Haemolytic 637, 644, 648, 649, 650, 651, 667, 671, 699. Haemolytic inactive, mouse erythrocytes 645. Haemolytic, mouse erythrocytes 646, 647. Haemolytic, mouse erythrocytes, high activity 638, 641, 643. Haemolytic, strong 626, 627, 628, 629, 630, 631, 652. Hemolytic, mouse-blood erythrocytes 302, 306. Hepatotoxin 1014. HIF-1 activator 899, 906. HIF-1 inhibitor 398, 433, 434. HIV-1 envelope-mediated fusion inhibitor 562, 563, 564, 565, 566. HIV-1 inhibitor 930, 934. HIV-1 protease inhibitor 781. HIV-1 replication inhibitor, C8166 256, 257. HIV-integrase inhibitor 946, 954, 958, 978, 994, 1011, 1012. HIV-rt inhibitor 143, 950, 951, 952, 995, 996. Hmn kinase EGFR inhibitor 327. hRCE protease inhibitor, hmn Ras-converting enzyme 557, 558, 559. Hyperactive effects upon reef-dwelling dish Eupomacentrus leucostictus 1033.

453

Hypoglycemic, high-fat diet mice, promotion of Adrb3 and GLUT4 mRNA expressions in skeletal muscle tissues 793. I Ichthyotoxic 31, 49, 141, 176, 202, 262, 853, 981, 982, 1034. Ichthyotoxic, mosquito fish Gambusia affinis 403, 587. Ichthyotoxin 146, 198, 354, 362, 367, 368, 455, 457, 508, 512, 525, 536, 546, 547, 549, 696, 697, 783, 784, 799, 870, 1030, 1031, 1032, 1033, 1039. Ichtyotoxin 782. IDO inhibitor 352, 939, 940. IL-6 production inhibitor 769, 772. IL-8 receptor inhibitor 931, 932, 933, 935. Immune system activity, glycoside lysosomal activity 663. Immune system activity, phagocytosis and ROS activator 663. Immunomodulator 885, 886. Immunomodulator, MLR mixed lymphocyte reaction 991. Immunomodulator, MLR mixed lymphocyte reaction, IM activity; LCV lymphocyte viability 979. Immunomodulatory 864. Immunostimulant 853, 854. Inducer of apoptosis, transformed mammalian cells 152. Inducer of hemolysis, erythrocytes 728. Induces apoptosis, HL60 cells in M/G2 phase 753. Induces hydroid Conjue uchidal settling, hydroid Conjue uchidal is epiphytic on brown alga Sargassum tortile 1045, 1046. Inducing apoptosis 498. Inductor of quinone reductase, indicating a possible cancer preventative role 992. Inhibitory effects on maturation of starfish oocytes and cell cycle arrest in HepG2 cell line were evaluated 962. Inhibits anti-IgE-induced release of histamine rat peritoneal mast cells 620, 692. Inhibits binding of [3H]-LTB4 to hmn neutrophils 865.

454

Index 5 Compound Pharmacological Activity Index

Inhibits binding of PAF to its receptors 286, 287, 288, 295. Inhibits cell division, fertilised starfish eggs 162. Inhibits cell division, fertilized ascidian eggs 119, 120, 121, 122, 123. Inhibits cell division, fertilized sea urchin eggs 7. Inhibits cell proliferation 925. Inhibits cell proliferation, peripheral blood mononuclear cells 388. Inhibits development of starfish embryo 980. Inhibits DNA synthesis, rheumatoid synovial fibroblast 948, 949, 997. Inhibits etiolated wheat coleoptile growth 493, 495. Inhibits feeding by copepod Tigriopus californicus 798. Inhibits gastrulation of sea star embryo Asterina pectinifera 391, 392, 393. Inhibits gastrulation of starfish embryos 605. Inhibits growth of fibroblasts, lymphocytic leukemia and lymphoblastic B and T cells 853, 854. Inhibits hallmarkers 786. Inhibits plant pathogenic mold Colletotrichum lagenarium 51. Inhibits polymerization of microtubules with a novel mechanism 1034. Inhibits RS321 16, 25. Inhibits superoxide production 148. Inhibits VEGF-A dependent endothelial cell sprouting 304. iNOS expression regulator 403. Inosine monophosphate dehydrogenase inhibitor 357, 358. Insecticidal, coconut pest Brontispa longissima 714, 715. Insecticidal, third-instar larvae of Brontispa longissima 716, 717, 719, 720. Insecticide 1003. Interleukin-8 receptor inhibitor 929. K Kinase PfGSK-3 inhibitor inactive 340. Kinase Pfnek-1 inhibitor, Plasmodium falciparum 340. Kinase PfPK5 inhibitor 340. Kinesin motor protein inhibitor 826, 830, 831.

L Larvicide 760. LC50 brine shrimp 910, 1002. LC50 brine shrimp Artemia salina 573. LC50 fish 573. LD50 brine shrimp 203, 944, 955, 1010. LD50 brine shrimp Artemia salina 586, 853, 903. LD50 fish 944, 955, 1010. LD50 mice 83. LD50 mosquito fish Gambusia affinis 586. LD50 mus ipr 61, 492, 776, 853. LD50 mus ivn 61. LD50 mus orl 491, 776. LD50 rat ipr 842. Leads for treatment of inflammatory pain, epilepsy and both breathing or movement disorders 584. Leucotriene formation inhibitor 83. Lipid peroxidation inhibitor 786, 800. Lipoxygenase inhibitor 83. Lipoxygenase inhibitor, hmn 1038. M Macrophage activation inhibitor 401, 402. Macrophage activation modulator 403. MAPKAP kinase 2 inhibitor 965, 1037. Markedly less active in all assays 700. Membranolytic, causing increase in number of lysed cells 844. Mitochondrial oxygen uptake inhibitor 842. Mitochondrial respiratory chain inhibitor, mammalian, interacting with NADH oxidase 1040. Mitogen-activated and stress-activated kinase MSK1 inhibitor 462, 464, 465. Mitogen-activated protein kinase activated protein kinase MAPKAPK-2 inhibitor 462, 464, 465. Molluscacidal 3, 424, 512. MT-stimulated kinesin motor protein inhibitor 827. Multi-functional nutrient 793. Muscle relaxant 990. Mycotoxin 841. N Na/K-ATPase inhibitor 789, 793, 1008, 1009, 1010.

Index 5 Compound Pharmacological Activity Index

Narcotic 1033. Negative inotropic activity, isolated gpg atria muscles 10. Nervous system activity, butyrylcholinesterase inhibitor 1013. Neurotrophic factor, ChAT inducer, basal forebrain cells 31. NF-κB inhibitor, RAW264.7 cells 859, 860, 861, 862, 1048, 1049, 1050. NGF synthesis stimulator 519. Nicotinic receptor inhibitor 446, 447, 448, 449, 450. NO generation inhibitor 403. NO production inhibitor, LPS-stimulated RAW264.7 cells 568, 585, 596, 597. NO production inhibitor, stimulated macrophages 721, 779, 780. Norepinephrin inhibitor 144. Norepinephrine antagonist 145, 202. O Oedema inhibitor 445. Ornithine decarboxylase inhibitor 425, 426, 419. Osteoporosis drug 770. P p56lck Tyrosine kinase inhibitor 412. PAcF antagonist 280. PAcF antagonist, inhibited PAcF binding to its receptor 285. PAF antagonist 286, 287, 288. PAF binding inhibitor 281, 282, 283, 284. Phosphoinositide-3-kinase PI3K inhibitor, 10 folder higher potency against PI3Kα than towards PI3Kγ 964. Phosphoinositol-specific phospholipase C inhibitor 836. Photosynthesis inhibitor 491, 492. Phytotoxic 776. Phytotoxin 491, 492, 493. Piscicide 667, 963. PKA inhibitor 875, 876. PKC inhibitor 484, 485, 486, 487, 488, 781, 875, 929, 931, 932, 933, 935. PKC inhibitor, good selectivity 876. PLA inhibitor 489.

455

PLA2 inhibitor 359, 360, 406, 488, 512, 524, 536, 572, 588, 589, 887, 917, 918, 922, 923, 942, 1034. PLA2 inhibitor, anti-inflammatory 413, 419. PLA2 inhibitor, bee venom PLA2 453, 454, 845. PLA2 inhibitor, hmn secretory 573. PLA2 inhibitor, mammalian 556. PLA2 inhibitor, selective 479, 480, 481, 482, 483. PLA2 is linked to initial step in cascade of enzymatic reactions that lead to generation of inflammatory mediators 413, 419. Platelet aggregation inhibitor 281, 282, 283, 284, 285, 523, 581. Platelet aggregation inhibitor, PAF-induced 286, 287, 288, 295. PP inhibitor 371. PP2A inhibitor 617. PTK inhibitor 333, 337, 338, 1057, 1058. PTK pp60 inhibitor 702, 703, 705. Putative biosynthetic precursor to halenaquinol and xestoquinone 334. R RCE-protease inhibitor 353. Recombinant hmn Cdc25b phosphatase inhibitor, an activator of cyclin dependent kinase Cdc2 whose presence is required for entry into mitosis phase of cell cycle 327. Reduction of pro-inflammatory MCP-1, PAI-1, IL6 and TNF-α mRNA expressions 793. Reverse transcriptase inhibitor 966. S Serine protease inhibitor 942. Similar levels of activation of cAMP signalling to the standard probe, forskolin 567. Specific inhibitors of PLA2 considered as potential drugs for treatment of inflammation and related diseases 413, 419. Starfish egg division inhibitor 161. Stimulates catalase 789. Stimulates catalase glutathione transferase 793. Stimulates GS transferase 789.

456

Index 5 Compound Pharmacological Activity Index

Stimulates nerve growth factor synth. 517. Superoxide production inhibitor, stimulated hmn neutrophils 60. Superoxide release inhibitor 159. T Thrombin receptor antagonist 656. T-lymphotropic cytostatic activity 853. Topoisomerase I inhibitor 229, 340. Topoisomerase II inhibitor 310, 311, 332, 333, 335, 336. Toxic, brine shrimp 119, 120, 121, 122, 123, 176, 179, 181, 190, 260, 354, 367, 368, 369, 386, 514, 572, 687, 711, 955, 980, 1010. Toxic, brine shrimp and abalone larvae 524. Toxic, brine shrimp Artemia salina 461, 575, 586, 586, 665, 666, 853. Toxic, brine shrimp lethality 944. Toxic, brine shrimp, Artemiasalina bioassay 574. Toxic, fish 574, 572, 955. Toxic, fish Gambusia salina 461. Toxic, fish lethality 1010, 944. Toxic, mice and other organism 653. Toxic, mosquito fish Gambusia affinis 586. Toxic, several predatory marine organisms: sea star, abalone larvae, brine shrimp 364.

(The End of HAMNP Volume 2)

Toxic, threshold brine shrimp 203. Toxin 774, 1036. TPK inhibitor 331, 944, 946, 954, 958, 978, 994, 1011, 1012, 1008, 1056. Treating macular degeneration potentially useful 795. Tremorgenic mycotoxin 1042. Tyrosine kinase inhibitor 1035. Tyrosine kinase inhibitor, TKp56lck 843. Tyrosine kinase pp60V-SRC inhibitor 325, 326, 327, 340, 967. V Vacular H+-ATPase inhibitor 826, 832, 833. Vasodilator, coronary 385. Vasodilator, coronary, markedly inhibits KClinduced contraction of rabbit isolated coronary artery 814. Vasopressin receptor antagonist 144. Vasopressin-V1 receptor antagonist 145, 202. VZV protease inhibitor 701, 707. α α11,3-Fucosyltransferase VII inhibitor 1010, 988.