Handbook of Active Marine Natural Products: Volume 5 Polyketides and Steroids 9783110653922, 9783110653632

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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 : 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 : 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 5: Polyketides and Steroids

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

ISBN 978-3-11-065363-2 e-ISBN (PDF) 978-3-11-065392-2 e-ISBN (EPUB) 978-3-11-065371-7 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 Aromatic 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 handbooks represent 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/10.1515/9783110653922-201

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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 handbook. 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 XXI List of Abbreviations and Acronyms XXV List of Cancer Cell Codes XXXV 1

Polyketides 1 1.1 Linear Polyketides 1 1.2 Nactins 16 1.3 Cytovaricins 17 1.4 Colletodiols 21 1.5 Malyngamides and Related Amides 23 1.6 Ansamycins 40 1.7 Other Polyenes Antibiotics 41 1.8 Linear Tetracyclines 43 1.9 Anguyclines 43 1.10 Palytoxins Nonmacrolide Polyethers 49 1.11 Amphidinols Nonmacrolide Polyethers 50 1.12 Other Nonmacrolide Polyethers 52 1.13 Ladder Polyethers 55 1.14 Polyether Antibiotics 83 1.15 Aplysiatoxins 96 1.16 Aflatoxins and Related Polyketides 101 1.17 Sorbicillin Polymers 106 1.18 Phorbaside Polyketides 118 1.19 Bafilomycins 120 1.20 Erythromycins 125 1.21 Kijanimicins 126 1.22 Resorcylic Acid Lactones 130 1.23 Antimycins 138 1.24 Bryostatins 145 1.25 Copiamycins 155 1.26 Fujimycins 155 1.27 Amphidinolides 156 1.28 Aplyronines 171 1.29 Lasonolides 174 1.30 Pectenotoxins 176 1.31 Sphinxolides 180 1.32 Swinholides 185

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1.33 1.34 1.35 1.36 2

Other Macrocyclic Polyketide Lactones 192 Bicyclic Polyketides 239 Tricyclic Polyketides 244 Tetra-and Higher-cyclic Polyketides 249

Steroids 251 2.1 Pregnane Steroids (C21) 251 2.2 Cholan-24-oic acid Steroids 255 2.3 Cholestane Steroids (C27) 256 2.4 Norcholestane and Dinorcholestane Steroids 327 2.5 A-nor-steroids 330 2.6 Ecdysteroids 331 2.7 Furostane Steroids (C27) 332 2.8 Ergostane Steroids (Excluding Withanolides) (C28) 339 2.9 27-Norergostane Steroids 402 2.10 Withanolide Steroids (C28) 402 2.11 Stigmastane Steroids (C29) 406 2.12 Gorgostane and Other Cyclopropacholestane Steroids 431 2.13 Seco-steroids 441 2.14 Miscellaneous Steroids 447

Index 1 Compound Name and Synonym Index 453 Index 2 Compound Molecular Formula Index 472 Index 3 Compound Organism Source Index 496 Index 4 Compound Sampling Geographic Locality Index 504 Index 5 Compound Pharmacological Activity Index 508

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/10.1515/9783110653922-202

Introduction The Handbook of Active Marine Natural Products covers eight volumes. This book is Volume 5: Polyketides and Steroids, which includes 1,144 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 1,144 for volume 5) and the main name. The following seven 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 1,144 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 the 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 129 Mayamycin is

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HO O

OH

O

OH O

H N

OH

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

Source Terms The source data of compound 129 Mayamycin is Source: Marine-derived streptomycete Streptomyces sp. HB202 (Baltic Sea) and sponge Halichondria panicea (Baltic Sea). 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) English-type name + Latin name of source 2 (sampling place)

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 129 Mayamycin, a set of multiple biodata is presented as follows:

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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)

Pharm: Antibacterial (Bacillus subtilis, IC50 = 8.0 μmol/L, control chloramphenicol, IC50 = 9.0 μmol/L; Brevibacterium epidermidis, IC50 = 7.45 μmol/L, control tetracycline, IC50 = 13.9 μmol/L; Dermabacter hominis, IC50 = 8.4 μmol/L, tetracycline, IC50 = 1.2 μmol/L; Klebsiella pneumonia, IC50 = 2.5 μmol/L; Propionibacterium acnes, IC50 = 31.2 μmol/L, chloramphenicol, IC50 = 1.0 μmol/L; Pseudomonas aeruginosa, IC50 = 2.5 μmol/L, chloramphenicol, IC50 = 27.3 μmol/L; Staphylococcus aureus, IC50 = 2.5 μmol/L, control moxifloxacin, IC50 = 7.5 μmol/L; Staphylococcus aureus MRSA, IC50 = 1.25 μmol/L; Staphylococcus epidermidis, IC50 = 0.31 μmol/L; Staphylococcus lentus, IC50 = 8.0 μmol/L, chloramphenicol, IC50 = 2.3 μmol/L; Xanthomonas campestris, IC50 = 30.0 μmol/L, chloramphenicol, IC50 = 3.6 μmol/L); cytotoxic (HepG2, IC50 = 0.2 μmol/L, control tamoxifen, IC50 = 23.4 μmol/L; HT29, IC50 = 0.3 μmol/L, tamoxifen, IC50 = 38.6 μmol/L; GXF-251 L, IC50 = 0.2 μmol/L, control ADM, IC50 = 0.052 μmol/L; LXF-529 L, IC50 = 0.16 μmol/L, ADM, IC50 = 0.052 μmol/L; MAXF-401 NL, IC50 = 0.29 μmol/L, ADM,

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IC50 = 0.052 μmol/L; MEXF-462 NL, IC50 = 0.13 μmol/L, ADM, IC50 = 0.052 μmol/L; PAXF-1657 L, IC50 = 0.15 μmol/L, ADM, IC50 = 0.052 μmol/L; RXF-486 L, IC50 = 0.33 μmol/L, ADM, IC50 = 0.052 μmol/L). The format is as follows: Pharm: Term name 1 (formatted detail information) Term name 2 (formatted detail information) Under the term name Antibacterial, a set of multiple antibacterial biodata is presented as follows: Antibacterial (Bacterium Bacillus subtilis, IC50 = 8.0 μmol/L, control chloramphenicol, IC50 = 9.0 μmol/L; Bacterium Brevibacterium epidermidis, IC50 = 7.45 μmol/L, control tetracycline, IC50 = 13.9 μmol/L; Bacterium Dermabacter hominis, IC50 = 8.4 μmol/L, tetracycline, IC50 = 1.2 μmol/L; Bacterium Klebsiella pneumonia, IC50 = 2.5 μmol/L; Bacterium Propionibacterium acnes, IC50 = 31.2 μmol/L, chloramphenicol, IC50 = 1.0 μmol/L; Bacterium Pseudomonas aeruginosa, IC50 = 2.5 μmol/L, chloramphenicol, IC50 = 27.3 μmol/L; Bacterium Staphylococcus aureus, IC50 = 2.5 μmol/L, control moxifloxacin, IC50 = 7.5 μmol/L; Bacterium Staphylococcus aureus MRSA, IC50 = 1.25 μmol/L; Bacterium Staphylococcus epidermidis, IC50 = 0.31 μmol/L; Bacterium Staphylococcus lentus, IC50 = 8.0 μmol/L, chloramphenicol, IC50 = 2.3 μmol/L; Bacterium Xanthomonas campestris, IC50 = 30.0 μmol/L, chloramphenicol, IC50 = 3.6 μmol/L). The format is as follows: Antibacterial (bacterium 1, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 2, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 3, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 4, quantitative data, positive control compound, control’s quantitative data (if any);

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bacterium 5, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 6, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 7, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 8, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 9, quantitative data, positive control compound, control’s quantitative data (if any); bacterium 10, quantitative data, positive control compound, control’s quantitative data (if any)). Under the term name Cytotoxic, a set of multiple cytotoxic biodata is presented as follows: Cytotoxic (in vitro HepG2, IC50 = 0.2 μmol/L, control tamoxifen, IC50 = 23.4 μmol/L; HT29, IC50 = 0.3 μmol/L, tamoxifen, IC50 = 38.6 μmol/L; GXF-251 L, IC50 = 0.2 μmol/L, control ADM, IC50 = 0.052 μmol/L; LXF-529 L, IC50 = 0.16 μmol/L, ADM, IC50 = 0.052 μmol/L; MAXF-401 NL, IC50 = 0.29 μmol/L, ADM, IC50 = 0.052 μmol/L; MEXF-462 NL, IC50 = 0.13 μmol/L, ADM, IC50 = 0.052 μmol/L; PAXF-1657 L, IC50 = 0.15 μmol/L, ADM, IC50 = 0.052 μmol/L; RXF-486 L, IC50 = 0.33 μmol/L, ADM, IC50 = 0.052 μmol/L). The format is as follows: Term name (in vitro/in vivo, target cancer cell 1, quantitative quantitative data (if any); target cancer cell 2, quantitative quantitative data (if any); target cancer cell 3, quantitative quantitative data (if any); target cancer cell 4, quantitative quantitative data (if any); target cancer cell 5, quantitative quantitative data (if any); target cancer cell 6, quantitative quantitative data (if any); target cancer cell 7, quantitative quantitative data (if any);

data, positive control compound, control’s data, positive control compound, control’s data, positive control compound, control’s data, positive control compound, control’s data, positive control compound, control’s data, positive control compound, control’s data, positive control compound, control’s

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target cancer cell 8, 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 have normalized expressions of almost all the pharmacological data discussed in the books. For complete information in volume 5, of all 853 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, as the author of those books, 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 a 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 on Marine Natural Products. At the same time, I also give my 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)

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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, I thank my family members. Without their complete and never-ending support, this book would never have been possible.

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

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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 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

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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) Source(s) Type 1

Type 5

Type 2

Type 6

Compound(s)

Type 4

Pharm-activity

Type 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 polyketides are isolated from cyanobacterium of genus Lyngbya? From index 3 of volume 5, one will get the following related data in detail: Lyngbya bouillonii 3, 545. Lyngbya gracilis 247. https://doi.org/10.1515/9783110653922-204

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How to Use the HAMNP Books

Lyngbya majuscula 64, 65, 66, 66, 70, 71, 72, 74, 76, 77, 78, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 90, 91, 244, 247, 249, 250, 251, 256, 257, 508. Lyngbya sordida 73. Lyngbya sp. 6, 77, 493, 494, 495, 544, 545. Since compounds 1–625 in volume 5 are polyketides, the answer of the current question must be these 37 compounds: 3, 6, 64–66, 70–74, 76–87, 90, 91, 244, 247, 249~251, 256, 257, 493–495, 508, 544, 545. Then, readers can enjoy studying these 37 compounds by reading the book, including their pharm-activity (question of types 3 and 5). For example, with entry 3, a reader will know that the compound 3 cyanolide A had already been isolated from cyanobacterium Lyngbya bouillonii (Pigeon I., Papua New Guinea), and it has Molluscicidal activity (snail vector Biomphalaria glabrata, LC50 = 1.2 μmol/L, very potent; molluscicides play a critical role in control of schistosomiasis transmission) and toxic activity (brine shrimp, LC50 = 10.8 μmol/L). O

O O

O

O O

O H O

O H H

H O

O OO O O O

(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 A549 from polyketides and steroids? And what are their marine sources?” To browse Index 5 of volume 5, searching “Cytotoxic, A549” and “Cytotoxic inactive, A549,” respectively, the following results were obtained (the “Cytotoxic inactive” means that pharmacological assay has been done, but the result is not active or activity is being very low): Cytotoxic, A549 28, 30, 42, 43, 44, 90, 112, 113, 115, 314, 315, 316, 317, 440, 441, 442, 443, 444, 445, 518, 556, 588, 592 (above polyketides), 631, 646, 647, 673, 674, 725, 729, 738, 744, 764, 765, 766, 767, 768, 769, 772, 774, 800, 810, 811, 828, 829, 840, 842, 843, 844, 849, 850, 888, 919, 920, 938, 939, 944, 947, 950, 951, 952, 959, 960, 961, 962, 969, 970, 971, 972, 974, 975, 979, 980, 981, 1003, 1004, 1005, 1021, 1024, 1044, 1046, 1047, 1048, 1050, 1051, 1053, 1055, 1056, 1065, 1098, 1099, 1101, 1105, 1106, 1123, 1124, 1129, 1139 (above steroids).

How to Use the HAMNP Books

XXIII

Cytotoxic inactive, A549 10, 11, 22, 23, 41, 275, 276, 279, 285, 301, 614 (above polyketides), 631, 677, 710, 721, 762, 763, 856, 876, 877, 878, 879, 883, 889, 891, 896, 897, 914, 916, 940, 941, 942, 943, 945, 946, 948, 965, 977, 1077, 1130 (above steroids). Further, from the entry bodies of the 98 active compounds (28, 30, 42,. . ., 1124, 1129, and 1139), all sources can be obtained (see Table 2). Table 2: Answer to the Above Type 4, 2, and 6 Questions. Vol.

Code Compound Name

Type

Related Sources





-Hydroxymethyldiscodermolate

Linear polyketides tetra- and higher branched

Lithistid sponge Discodermia sp. (numerous places, Bahamas, using Johnson-Sea-Link submersible)





Lingshuiol

Linear polyketides tetra- and higher branched

Dinoflagellate Amphidinium sp.





Z-Siphonarienfuranone

Linear polyketides tetra- and higher branched

Pulmonate limpets Siphonaria pectinata (Cádiz, Spain, °′ W°´N) and Siphonaria grisea

. . .. . . . . .. . . . . .. . . 

 -O-Deacetylluffasterol B



 Hirsutosterol A



 Lobophytosterol‡

. . .. . . ,-Seco-steroids Sponge Spongia agaricina (Cádiz, Spain) ,-Seco-steroids Soft coral Cladiella hirsuta (Taiwan waters) Miscellaneous steroids

Soft coral Lobophytum laevigatum (KhanhHoa province, Vietnam)

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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XXVI

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 MG-MID 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

XXVII

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 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

XXVIII

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

XXIX

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

XXX

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

XXXI

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

XXXII

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 co-localized 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

XXXIII

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)

https://doi.org/10.1515/9783110653922-206

XXXVI

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)

XXXVII

XXXVIII

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)

XXXIX

XL

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)

XLI

XLII

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

List of Cancer Cell Codes

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 ascite 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)

XLIII

XLIV

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)

1 Polyketides 1.1 Linear Polyketides 1 Balticolid Type: Linear polyketides nobranched. C12H16O4 Colorless oil, [α]D22 = +135.2° (c = 0.35, MeOH). Source: An unidentified ascomycetous fungus (drift-wood, Greifswalder Bodden, Baltic Sea, Germany). Pharm: Anti-HSV-1 (IC50 = 0.45 μmol/L). Ref: M. A. M. Shushni, et al, Mar. Drugs, 2011, 9, 844│S. Z. Moghadamtousi, et al, Mar. Drugs, 2015, 13, 4520 (rev) HO O O O

2 Aureoverticillactam Type: Linear polyketides monobranched. C28H39NO4 Amorph. solid. Source: Marinederived streptomycete Streptomyces aureoverticillatus NPS001583. Pharm: Cytotoxic (HT29, EC50 = (3.6 ± 2.6)μmol/L; B16-F-10, EC50 = (2.2 ± 0.9)μmol/L; JurKat, EC50 = (2.3 ± 1.1)μmol/L). Ref: S. S. Mitchell, et al, JNP, 2004, 67, 1400 OH O

HO OH

HN

3 Cyanolide A Type: Linear polyketides dibranched. C42H72O16 Oil, [α]D23 = −59° (c = 0.6, CHCl3). Source: Cyanobacterium Lyngbya bouillonii (Pigeon I., Papua New Guinea). Pharm: Molluscacidal (snail vector Biomphalaria glabrata, LC50 = 1.2 μmol/L, very potent; molluscacides play a critical role in control of schistosomiasis transmission); toxic (brine shrimp, LC50 = 10.8 μmol/L). Ref: H. Kim, et al, Org. Lett., 2010, 12, 2880│A. R. Pereira, et al, JNP, 2010, 73, 217

https://doi.org/10.1515/9783110653922-001

2

1 Polyketides

O

O

O

O

O

O

O H O

H H

O H O

O OO O O O

4 Formosalide A Type: Linear polyketides dibranched. C32H50O9 Amorph. solid, [α]D25 = +17.3° (c = 0.01, MeOH). Source: Dinoflagellate Prorocentrum sp. (seaweed washings, South Bay, Taiwan). Pharm: Cytotoxic (CCRF-CEM, LD50 = 0.54 μg/mL, DLD-1, LD50 > 40 μg/mL). Ref: C. -K. Lu, et al, Tet. Lett., 2009, 50, 1825 HO HO HO

OH 8

O O

O HO O

5 Formosalide B Type: Linear polyketides dibranched. C33H52O9 Amorph. solid, [α]D24 = +18.8° (c = 0.04, MeOH). Source: Dinoflagellate Prorocentrum sp. (seaweed washings, South Bay, Taiwan). Pharm: Cytotoxic (CCRF-CEM, LD50 = 0.43 μg/mL, DLD-1, LD50 = 2.73 μg/mL). Ref: C. -K. Lu, et al, Tet. Lett., 2009, 50, 1825 HO HO HO

8

O

O O

O HO O

6 Koshikalide Type: Linear polyketides dibranched. C17H26O4 Oil, [α]D22 = +156° (c = 0.03, MeOH). Source: Cyanobacterium Lyngbya sp. Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 42 μg/mL, weak). Ref: A. Iwasaki, et al, Tet. Lett., 2010, 51, 959

1.1 Linear Polyketides

3

O

O

O HO

7 Colopsinol A Type: Linear polyketides tribranched. C72H120O25S [α]D20 = −11° (c = 0.35, MeOH). Source: Dinoflagellate Amphidinium sp. Y-5. Pharm: DNA polymerase α inhibitor (IC50 = 13 μmol/L). DNA polymerase β inhibitor (IC50 = 7 μmol/L). Ref: J. Kobayashi, et al, JOC, 1999, 64, 1478│T. Kubota, et al, JCS Perkin I, 1999, 3483│J. Kobayashi, et al, Pure Appl Chem, 2003, 75:337 OH OH OH

O

O

O

OH

O

H

OH

O

O O S O

OH

O OH O

HO

H

OH

O

HO

OH OH

O

O

8 Colopsinol C Type: Linear polyketides tribranched. C62H104O20S Amorph. solid (Na salt). Source: Dinoflagellate Amphidinium sp. Y-5. Pharm: Cytotoxic (L1210, IC50 = 7.8 μg/mL). Ref: J. Kobayashi, et al, JOC, 1999, 64, 1478│T. Kubota, et al, JCS Perkin I, 1999, 3483│J. Kobayashi, et al, Pure Appl Chem, 2003, 75:337 OH H

O

OH OH

OH

O

O

O OH O

HO

O O

S

OH

O OH

OH OH

O H

O

4

1 Polyketides

9 Colopsinol E Type: Linear polyketides tribranched. C65H110O20S Amorph. solid (Na salt). Source: Dinoflagellate Amphidinium sp. Y-5. Pharm: Cytotoxic (L1210, IC50 = 7.0 μg/mL). Ref: T. Kubota, et al, CPB, 2000, 48, 1447│J. Kobayashi, et al, Pure Appl Chem, 2003, 75:337 OH

OH

O H

OH

O

O

OH

O S O OH OH

O

O

O

O OH

O OH OH

OH

10 2-[3,5-Diethyl-5-(2-ethyl-3-hexen-1-yl)-2(5H)-furanylidene]acetic acid methyl ester Methyl 9,10-didehydro-3,6-epoxy-4,6,8-triethyl-2,4-dodecadienoic acid ester Type: Linear polyketides tribranched. C19H30O3 [α]D = −175° (c = 1.4, CCl4). Source: Sponges Monotria japonica, Plakortis halichondrioides and Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 = (2.6 ± 0.3)μmol/L; K562, IC50 = (0.8 ± 0.1)μmol/L; A549, IC50 > 100 μmol/L; Bel7402, IC50 > 100 μmol/L, control Adriamycin: HeLa, IC50 = (0.6 ± 0.0)μmol/L; K562, IC50 = (0.3 ± 0.0)μmol/L; A549, IC50 = (0.2 ± 0.0)μmol/L) (Zhang, 2013); oocyte-lytic activity (non-selectively lyses immature starfish oocytes Asterina pectinifera, lysed both oocyte’s plasma membrane and nuclear envelope, MEC = 25 μg/mL). Ref: D. B. Stierle, et al, JOC, 1980, 45, 3396│A. Rudi, et al, JNP, 1993, 56, 1827│E. W. Schmidt, et al, Tet. Lett., 1996, 37, 6681│ M. Yanai, et al, BoMC, 2003, 11, 1715│C. W. Lim, et al, Agric. Chem. Biotechnol., 2006, 49, 21│J. Zhang, et al, JNP, 2013, 76, 600

O O

O

11 2-[3,5-Diethyl-5-(2-ethylhexyl)-2(5H)-furanylidene]acetic acid methyl ester Methyl(2Z,6R,8S)-3,6-epoxy-4,6,8-triethyldodeca-2,4-dienoate Type: Linear polyketides tribranched. C19H32O3 Oil, [α]D = −78° (c = 0.19, CHCl3). Source: Sponges Plakortis aff. angulospiculatus (Palau, Oceania) and Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Antileishmanial (effects on proliferation of Leishmania mexicana promastigotes, LD50 = 2.71 μg/mL; control 1 sponge metabolite Ilimaquinone,

1.1 Linear Polyketides

5

LD50 = 5.6 μg/mL, control 2 Ketoconozole, LD50 = 0.06 μg/mL) (Compagnone, 1998); cytotoxic (HeLa, IC50 = (4.2 ± 0.4)μmol/L; K562, IC50 = (5.3 ± 0.5)μmol/L; A549, IC50 > 100 μmol/L; Bel7402, IC50 > 100 μmol/L, control Adriamycin: HeLa, IC50 = (0.6 ± 0.0)μmol/L; K562, IC50 = (0.3 ± 0.0)μmol/L; A549, IC50 = (0.2 ± 0.0)μmol/L)) (Zhang, 2013). Ref: R. S. Compagnone, et al, Tetrahedron, 1998, 54, 3057│J. Zhang, et al, JNP, 2013, 76, 600

O O

O

12 Gracilioether B Type: Linear polyketides tribranched. C19H28O4 Amorph. solid, [α]D35 = −120° (c = 0.03, MeOH). Source: Sponge Agelas gracilis (Oshima-Shinsone, Japan). Pharm: Antiplasmodial (Plasmodium falciparum ItG, IC50 = 0.5 μg/mL); antileishmanial (Leishmania major). Ref: R. Ueoka, et al, JOC, 2009, 74, 4203

11

O O

O

O

13 Gracilioether C Type: Linear polyketides tribranched. C19H30O4 Amorph. solid, [α]D32 = −24° (c = 0.02, MeOH). Source: Sponge Agelas gracilis (Oshima-Shinsone, Japan). Pharm: Antimalarial; cytotoxic. Ref: R. Ueoka, et al, JOC, 2009, 74, 4203

11

O OH

O

O

14 Methyl(2Z,6R,8S)-4,6-diethyl-3,6-epoxy-8-methyldodeca-2,4-dienoate Type: Linear polyketides tribranched. C18H30O3 Oil, [α]D = −92° (c = 1.1, CHCl3). Source: Sponge Plakortis aff. angulospiculatus (Palau, Oceania). Pharm: Antileishmanial (effects on proliferation of Leishmania mexicana promastigotes, LD50 = 1.86 μg/mL; control 1 sponge metabolite Ilimaquinone, LD50 = 5.6 μg/mL, control 2 Ketoconozole, (LD50 = 0.06 μg/mL)). Ref: R. S. Compagnone, et al, Tetrahedron, 1998, 54, 3057│J. C. Braekman, et al, JNP, 1998, 61, 1038

6

1 Polyketides

O O

O

15 Methyl 3,6-epoxy-4R, 8R-diethyl-6S-methyl-2Z, 9E-dodecadienoate Type: Linear polyketides tribranched. C18H30O3 Oil, [α]D25 = +20° (c = 0.001, CHCl3). Source: Sponge Plakortis simplex (Caribbean Sea). Pharm: Cytotoxic (WEHI-164, IC50 = 10 μg/mL). Ref: F. Cafieri, et al, Tetrahedron, 1999, 55, 7045

O O O

16 Methyl-3,6-epoxy-4,8-diethyl-6-methyl-2-dodecenoate Type: Linear polyketides tribranched. C18H32O3 Oil, [α]D25 = +5° (c = 0.001, CHCl3). Source: Sponge Plakortis simplex (Caribbean Sea). Pharm: Cytotoxic (WEHI-164, IC50 = 15.5 μg/mL). Ref: F. Cafieri, et al, Tetrahedron, 1999, 55, 7045

O O O

17 Ostreol A Type: Linear polyketides tribranched. C67H112N2O23 Source: Dinofiagellate Ostreopsis cf. ovata (epiphytic, benthic, Jeju I., R. O. Korea). Pharm: Toxic (brine shrimp, significantl). Ref: B. S. Hwang, et al, Bioorg. Med. Chem. Lett., 2013,23, 3023 OH NH2 OH O HO OH

OH N H

OH

OH OH OH OH

OH

OH

OH

HO OH

OH OH

O

3

OH

OH

O OH

1.1 Linear Polyketides

7

18 Prorocentrol Type: Linear polyketides tribranched. C68H114O34 Source: Dinoflagellate Prorocentrum hoffmannianum CCMP683. Pharm: Cytotoxic (P388, moderate); algicide, active against diatom Nitzschia sp. Ref: K. Sugahara, et al, JOC, 2011, 76, 3131 OH

OH

OH

HO

OH

HO

O

OH

HO

OH

OH

OH

OH

O O

OH OH

OH

OH

OH HO OH

OH

OH

OH HO OH

OH

O

OH OH

OH

OH

OH

19 Spongidepsin Type: Linear polyketides tribranched. C27H39NO3 White amorph. solid, [α]D = −61.8° (c = 0.014 g/100ml, MeOH). Source: Sponge Spongia sp. (family Spongidae, class Demospongiae, Vanuatu, May 1997, voucher specimens R1739 in IRD Center of Nouméa, New Caledonia). Pharm: Cytotoxic (antiproliferative, mus monocyte/macrophage cell line J774.A1, IC50 = 0.56 μmol/L, control 6-MP (6-Mercaptopurine), IC50 = 0.003 μmol/L; hmn epithelial kidney cell line HEK-293, IC50 = 0.66 μmol/L, 6-MP, IC50 = 0.007 μmol/L; WEHI-164, IC50 = 0.42 μmol/L, 6-MP IC50 = 0.017 μmol/L). Ref: A. Grassia, et al, Tetrahedron, 2001, 57, 6257 O N O

O

20 Amphidinin A Type: Linear polyketides tetra- and higher-branched. C22H38O4 Colorless oil, [α]D18 = 300° (c = 0.03, MeOH). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 3.6 μg/mL; KB, IC50 = 3.0 μg/mL). Ref: J. Kobayashi, et al, Tet. Lett., 1994, 35, 7049 HO

OH O OH

8

1 Polyketides

21 Amphirionin 4 Type: Linear polyketides tetra- and higher-branched. C26H40O3 Source: Dinofiagellate Amphidinium sp. Pharm: Cell growth promoter (murine bone marrow stromal ST-2 cells, very potent and selective). Ref: M. Minamida, et al, Org. Lett., 2014, 16, 4858

OH

O OH

22 Aspericin A Type: Linear polyketides tetra- and higher-branched. C17H30O4 Pale yellow wax, [α]D22 = +24° (c = 0.1, CHCl3). Source: Marine-derived fungus Rhizopus sp. 2-PDA-61 from bryozoan Bugula sp. (China waters). Pharm: Cytotoxic (P388, IC50 > 100 μmol/L, control VP-16, IC50 = 0.064 μmol/L; HL60, IC50 = 49.3 μmol/L, VP-16, IC50 = 0.083 μmol/L; A549, IC50 > 100 μmol/L, VP-16, IC50 = 1.400 μmol/L; Bel7402, IC50 = 55.1 μmol/L, VP-16, IC50 = 1.025 μmol/L). Ref: F. Wang, et al, Magn. Reson. Chem., 2010, 48, 155 O O

O OH

23 Aspericin C Type: Linear polyketides tetra- and higher-branched. C17H30O4 Wax, [α]D22 = −2° (c = 0.1, CHCl3). Source: Marine-derived fungus Rhizopus sp. 2-PDA-61 from bryozoan Bugula sp. (China waters). Pharm: Cytotoxic (P388, IC50 = 14.6 μmol/L, control VP-16, IC50 = 0.064 μmol/L; HL60, IC50 = 7.1 μmol/L, VP-16, IC50 = 0.083 μmol/L; A549, IC50 = 61.4 μmol/L, VP-16, IC50 = 1.400 μmol/L; Bel7402, IC50 = 24.2 μmol/L, VP-16, IC50 = 1.025 μmol/L). Ref: F. Wang, et al, Magn. Reson. Chem., 2010, 48, 155 HO O O

O

24 Belizeanolic acid Type: Linear polyketides tetra- and higher-branched. C81H134O21 Amorph. solid, [α]D25 = −5.2° (c = 0.002, MeOH). Source: Dinoflagellate Prorocentrum belizeanum. Pharm: Cytotoxic (A2780, GI50 = (0.26 ± 0.09)μmol/L; SW1573, GI50 = (0.31 ± 0.06) μmol/L; HBL100, GI50 = (0.32 ± 0.04)μmol/L; T47D, GI50 = (0.40 ± 0.09)μmol/L;

1.1 Linear Polyketides

9

WiDr, GI50 = (0.41 ± 0.04)μmol/L). Ref: J. G. Napolitano, et al, Angew. Chem., Int. Ed., 2009, 48, 796 HO

OH

OH

HO

53

O

H OH

O

OH

HO H

OH

O

OH

COOH OH

OH

H

1

OH

OH O

HO

OH

H

H

25 Denticulatin A Type: Linear polyketides tetra- and higher-branched. C23H40O5 Oil, [α]D = −30.7° (c = 1.49, CHCl3). Source: Pulmonate limpet Siphonaria denticulata. Pharm: Ichthyotoxin. Ref: J. E. Hochlowski, et al, JACS, 1983, 105, 7413│I. Peterson, et al, Tet. Lett., 1992, 33, 801 OH O

O O OH H

26 Denticulatin B Type: Linear polyketides tetra- and higher-branched. C23H40O5 Cryst., mp 137–141 °C, [α]D = −26.4° (c = 0.39, CHCl3). Source: Pulmonate limpet Siphonaria denticulata. Pharm: Ichthyotoxin. Ref: J. E. Hochlowski, et al, JACS, 1983, 105, 7413│I. Peterson, et al, Tet. Lett., 1992, 33, 801 H

O

OH 10

O

O OH

27 Halichomycin Type: Linear polyketides tetra- and higher-branched. C33H49NO5 Oil, [α]D20 = +3.8° (c = 1.2, CHCl3). Source: Marine-derived streptomycete Streptomyces hygroscopicus

10

1 Polyketides

from fish Halichoeres bleekeri. Pharm: Cytotoxic (P388, ED50 = 0.13 μg/mL). Ref: C. Takahashi, et al, Tet. Lett., 1994, 35, 5013

H

O

H H

O

H NH

O

O O

28 5-Hydroxymethyl-discodermolate Type: Linear polyketides tetra- and higher-branched. C34H59NO9 Solid, [α]D21 = +14.6° (c = 0.1, MeOH). Source: Lithistid sponge Discodermia sp. (numerous places, Bahamas, using Johnson-Sea-Link submersible). Pharm: Cytotoxic (P388, IC50 = 65.8 nmol/L; A549, IC50 = 74 nmol/L). Ref: S. P. Gunasekera, et al, JNP, 2002, 65, 1643│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

HO HO

OH

O

OH

O

NH2 O

OH

O

29 Karatungiol A Type: Linear polyketides tetra- and higher-branched. C73H132O28 Pale yellow solid, [α]D17 = +3.6° (c = 0.1, MeOH). Source: Dinoflagellate Amphidinium sp. Pharm: Antifungal. Ref: K. Washida, et al, Tet. Lett., 2006, 47, 2521 HO 15 14

HO HO

OH

HO

O OH OH

OH

OH

HO OH OH H

OH

OH

OH OH

H OH

O H

HO OH 5

OH OH

O

H

OH

OH OH

OH

1.1 Linear Polyketides

11

30 Lingshuiol Type: Linear polyketides tetra- and higher-branched. C69H122O25 Pale yellow solid, [α]D25 = −8° (c = 0.28, MeOH). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (A549, IC50 = 0.21 μmol/L; HL60, IC50 = 0.23 μmol/L); toxic (primary rat hepatocytes, IC50 = 0.21 μmol/L). Ref: X. -C. Huang, et al, BoMCL, 2004, 14, 3117│X. M. Qi, et al, Toxicon, 2007, 50, 278

HO

OH

HO HO

O OH OH

OH

OH

OH OH

OH

OH

OH

OH OH

HO OH

OH

O

OH

OH

O

5

OH

OH

31 Luteophanol A Type: Linear polyketides tetra- and higher-branched. C60H102O25S Amorph. solid, [α]D29 = −7.6° (c = 1, MeOH). Source: Dinoflagellate Amphidinium sp. Y-52 from flatworm Pseudaphanostoma luteocoloris. Pharm: Antibacterial (Staphylococcus aureus, MIC = 33 μg/mL, Sarcina lutea, MIC = 33 μg/mL, Bacillus subtilis, MIC = 66 μg/mL); phycotoxin. Ref: Y. Doi, et al, JOC, 1997, 62, 3820 O O HO

S O OH OH

OH

OH

OH

OH OH

OH

OH

OH

O

OH OH

OH

OH

HO O

OH

OH

OH OH

12

1 Polyketides

32 Myriaporone 3 Antibiotic MT 332 Type: Linear polyketides tetra- and higher-branched. C19H32O7 Source: Bryozoan Myriapora truncata. Pharm: Cytotoxic (inseparable equilibrium mixture with Myriaporone 4, 0.2 μg/mL, L1210, InRt = 88%). Ref: M. Pérez, et al, Angew. Chem., Int. Ed., 2004, 43, 1724│K. N. Fleming, et al, Angew. Chem., Int. Ed., 2004, 43, 2728│J.-F. Cheng, et al, JNP, 2007, 70, 332 OH

O

OH O OH

O OH

33 Myriaporone 4 Type: Linear polyketides tetra- and higher-branched. C19H32O7 Source: Bryozoan Myriapora truncata. Pharm: Cytotoxic (inseparable equilibrium mixture with Myriaporone 3, 0.2 μg/mL, L1210, InRt = 88%). Ref: M. Pérez, et al, Angew. Chem., Int. Ed., 2004, 43, 1724│K. N. Fleming, et al, Angew. Chem., Int. Ed., 2004, 43, 2728│J. -F. Cheng, et al, JNP, 2007, 70, 332

O

OH

OH

OH

O

OH

O

34 Niuhinone A Type: Linear polyketides tetra- and higher-branched. C24H36O3 Oil, [α]D = +55° (c = 0.68, Hexane). Source: Cephalaspids Bulla occidentalis (Yucatan coast, Gulf of Mexico) and Philinopsis speciosa. Pharm: Toxic (brine shrimp). Ref: S. J. Coval, et al, Tet. Lett., 1985, 26, 5359│A. Cutignano, et al, Tet. Lett., 2011, 52, 4595

O O

O

35 Niuhinone B Type: Linear polyketides tetra- and higher-branched. C25H38O3 [α]D = +55° (c = 0.47, Hexane). Source: Cephalaspids Bulla occidentalis (Yucatan coast, Gulf of Mexico), Bulla gouldiana, Navanax inermis and Philinopsis speciosa. Pharm: Toxic (brine shrimp). Ref: S. J. Coval, et al, Tet. Lett., 1985, 26, 5359│A. Spinella, et al, Tetrahedron, 1993, 49, 3203│A. Cutignano, et al, Tet. Lett., 2011, 52, 4595

1.1 Linear Polyketides

O

O

O

13

36 Saiyacenol A Type: Linear polyketides tetra- and higher-branched. C30H51BrO6 Source: Red alga Laurencia viridis (Callao Salvaje, Tenerife, Canary Is., Spain). Pharm: Cytotoxic. Ref: F. Cen-Pacheco, et al, Tetrahedron, 2012, 68, 7275

O

O

O OH

O O Br

37 Saiyacenol B Type: Linear polyketides tetra- and higher-branched. C30H51BrO6 Source: Red alga Laurencia viridis (Callao Salvaje, Tenerife, Canary Is., Spain). Pharm: Cytotoxic. Ref: F. Cen-Pacheco, et al, Tetrahedron, 2012, 68, 7275

O

O

O OH

O O Br

38 Saliniketal A Type: Linear polyketides tetra- and higher-branched. C22H37NO5 Amorph. powder, [α]D = −13.7° (c = 0.13, MeOH). Source: Marine-derived bacterium Salinispora arenicola YM23-082, marine derived streptomycete Streptomyces arenicola CNR-005. Pharm: Antibacterial (Staphylococcus aureus IFO 12732, MIC = 37 μg/mL; Bacillus subtilis IFO 3134, MIC = 111 μg/mL; Cytophaga marinoflava IFO 14170, MIC > 200 μg/mL; Escherichia coli IFO 3301, MIC > 200 μg/mL; Pseudomonas aeruginosa IFO 3446, MIC > 200 μg/mL); antifungal (Candida albicans IFO 1060, MIC > 200 μg/mL); ornithine decarboxylase induction inhibitor (IC50 = 1.9–7.8 μg/mL). Ref: S. Matsuda, et al, J. Antibiot., 2009, 62, 519│P. G. Williams, et al, JNP, 2007, 70, 83 H O

OH

OH

O H2N

O

14

1 Polyketides

39 Saliniketal B Type: Linear polyketides tetra- and higher-branched. C22H37NO6 Amorph. powder, [α]D = −22.4° (c = 0.11, MeOH). Source: Marine-derived streptomycete Streptomyces arenicola CNR-059. Pharm: Ornithine decarboxylase induction inhibitor (IC50 = 1.9–7.8 μg/mL). Ref: P. G. Williams, et al, JNP, 2007, 70, 83 H O

OH

OH

OH

O H2N

O

40 Simplakidine A Type: Linear polyketides tetra- and higher-branched. C24H37NO6 Amorph. solid, [α]D25 = −21.7° (c = 1.2, MeOH). Source: Sponge Plakortis simplex. Pharm: Cytotoxic (weak). Ref: C. Campagnuolo, et al, Org. Lett., 2003, 5, 673

H

OH O O

OH

O

–

N

+

O

41 Siphonarienedione Type: Linear polyketides tetra- and higher-branched. C21H36O2 Oil, [α]D = +32.5° (c = 0.52, CHCl3). Source: Pulmonate limpets Siphonaria pectinata (Cádiz, Spain, 6°18ʹW36°32ʹN) and Siphonaria grisea. Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all ED50 ≥ 10 μg/mL); antibacterial (gram-positive bacteria); antifungal. Ref: M. Norte, et al, Tetrahedron, 1990, 46, 1669│ M. C. Paul, et al, Tetrahedron, 1997, 53, 2303│ M. A. Calter, et al, JACS, 2002, 124, 13127

O

O

42 Z-Siphonarienfuranone Type: Linear polyketides tetra- and higher-branched. C20H34O3 Source: Pulmonate limpets Siphonaria pectinata (Cádiz, Spain, 6°18ʹW36°32ʹN) and Siphonaria grisea. Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all ED50 = 2.5 μg/mL); antibacterial (gram-positive bacteria). Ref: Norte, M. et al, Tetrahedron, 1990, 46, 1669│ M. C. Paul, et al, Tetrahedron, 1997, 53, 2303

1.1 Linear Polyketides

15

O HO O

43 Siphonarienfuranone Type: Linear polyketides tetra- and higher-branched. C20H34O3 Oil, [α]D = +101.5° (c = 0.14, CHCl3). Source: Pulmonate limpets Siphonaria pectinata (Cádiz, Spain, 6°18ʹW36°32ʹN) and Siphonaria grisea. Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all ED50 = 5 μg/mL); antibacterial (gram-positive bacteria). Ref: Norte, M. et al, Tetrahedron, 1990, 46, 1669│ M. C. Paul, et al, Tetrahedron, 1997, 53, 2303

O O HO

44 Siphonarienolone Type: Linear polyketides tetra- and higher-branched. C20H38O2 Oil, [α]D = +19.6° (c = 0.11, CHCl3). Source: Pulmonate limpets Siphonaria pectinata (Cádiz, Spain, 6°18ʹW36°32ʹN) and Siphonaria grisea. Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all ED50 = 2.5 μg/mL); antibacterial (gram-positive bacteria); antifungal. Ref: M. Norte, et al, Tetrahedron, 1990, 46, 1669│ M. C. Paul, et al, Tetrahedron, 1997, 53, 2303│ M. A. Calter, et al, JACS, 2002, 124, 13127

OH

O

45 Vatoxin-a Type: Linear polyketides tetra- and higher-branched. C132H228N2O51 Source: Dinoflagellate Ostreopsis ovata (seawater, Adriatic and Tyrrhenian coasts, Italy). Pharm: Toxic (in vivo, mice, lethal over a very short time period and also caused limb paralysis). Ref: P. Ciminiello, et al, J. Am. Soc. Mass Spectrom., 2008, 19, 111│P. Ciminiello, et al, Chem.-Eur. J., 2012, 18, 16836│P. Ciminiello, et al, JACS, 2012, 134, 1869

16

1 Polyketides

OH

O

OH

O

OH OH

HO

OH O

OH

O

OH

OH

HO

OH OH

OH

OH OH

N H

N H

HO

O

OH O

OH O

OH OH

OH

OH

OH

O

OH

HO OH

OH

O

O

HO

OHOH OH O

O

OH OH

OH

OH OH

OH OH

OH

1.2 Nactins 46 Feigrisolide C Nonactyl homononactoate Type: Nactins. C21H36O7 Powder, [α]D20 = +17.2° (c = 0.4, MeOH). Source: Marine-derived streptomycete Streptomyces sp. Pharm: Antibacterial. Ref: H. Laatsch, Dissertation, Univ. of Göttingen, 2005 O HO

OH

O

H

H

O

O

H

H O

47 Feigrisolide D Homononactyl homononactoate Type: Nactins. C22H38O7 Oil, [α]D20 = +15.7° (c = 0.2, MeOH). Source: Marine-derived streptomycete Streptomyces sp. Pharm: Antibacterial. Ref: Y. Q. Tang, et al, J. Antibiot., 2000, 53, 934 O HO

O

H

H O

O

H

H

OH

O

48 Nonactin Werramycin Type: Nactins. C40H64O12 Needles (MeOH), mp 149–150 °C, [α]D20 = 0° (c = 2, CHCl3). Source: Marine-derived streptomycete Streptomyces sp. KORDI-3238.

1.3 Cytovaricins

17

Pharm: Antibacterial (gram-positive bacteria); Potassium ion membrane transporter; selectively complexes with ammonium (Thallium and Potassium ions, used in ammonium-specific electrodes). Ref: S.-Y. Jeong, et al, J. Antibiot., 2006, 59, 234 O

H

H O O

H

H

O

O O

O O

O

O

H

H

O

H

O

H

1.3 Cytovaricins 49 Antibiotic IB 96212 Type: Cytovaricins. C54H94O16 Cryst., mp 165–166 °C, [α]D25 = −42.3° (c = 0.22, CHCl3). Source: Marine-derived bacterium Micromonospora sp. (fermentation liquid). Pharm: Cytotoxic. Ref: L. M. Cañedo, et al, J. Antibiot., 2000, 53, 479 OH O HO

OH

O OH

OH

OH

OH

OH

O O OH

O O

OH

50 Maclafungin Type: Cytovaricins. C46H80O12 Powder, mp 195 °C, [α]D = +32.8° (c = 0.41, CHCl3). Source: An unidentified actinomycete Y-8521050. Pharm: Antifungal. Ref: T. Mukhopadhyay, et al, Tetrahedron, 1998, 54, 13621

18

1 Polyketides

OH OH

OH

O

OH

O

HO

O O OH

O

OH

51 Neomaclafungin A Type: Cytovaricins. C44H76O11 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974 OH OH

O

OH

HO

OH O O

O O

OH

52 Neomaclafungin B Type: Cytovaricins. C45H78O11 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974 OH OH

O

OH

HO

OH O O

O O

OH

1.3 Cytovaricins

19

53 Neomaclafungin C Type: Cytovaricins. C45H78O11 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974

OH OH

O

OH

HO

OH O O

O O

OH

54 Neomaclafungin D Type: Cytovaricins. C46H80O11 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974

OH OH

O

OH

HO

OH O O

O O

OH

55 Neomaclafungin E Type: Cytovaricins. C43H74O10 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974

20

1 Polyketides

OH OH

O

OH

OH O O

O O

OH

56 Neomaclafungin F Type: Cytovaricins. C44H76O10 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974 OH OH

O

OH

OH O O

O O

OH

57 Neomaclafungin G Type: Cytovaricins. C45H78O10 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974 OH OH

OH

O

OH O O

O O

OH

1.4 Colletodiols

21

58 Neomaclafungin H Type: Cytovaricins. C45H78O10 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974

OH OH

O

OH

OH O O

O O

OH

59 Neomaclafungin I Type: Cytovaricins. C46H80O10 Source: Marine-derived actinomycete Actinoalloteichus sp. (sediment, Usa Bay, Kochi Prefecture, Japan). Pharm: Antifungal (Trichophyton mentagrophytes). Ref: S. Sato, et al, JNP, 2012, 75, 1974

OH OH

OH

O

OH O O

O O

OH

1.4 Colletodiols 60 Clonostachydiol Type: Colletodiols macrodilides. C14H20O6 Cryst., mp 164 °C, [α]D20 = +103° (c = 1, MeOH). Source: Marine-derived fungus Gliocladium sp. Pharm: Anthelmintic. Ref: S. Grabley, et al, J. Antibiot., 1993, 46, 343│A. V. R. Rao, et al, Tet. Lett., 1995, 36, 139; 143

22

1 Polyketides

O O

1 5

HO

12

O

8

OH O

61 Colletoketol Grahamimycin A Type: Colletodiols macrodilides. C14H18O6 Prisms (Me2CO/petrol), mp 147.5–150 °C (dec), mp 142–143 °C, [α]D25 = −34.2° (c = 0.05, CHCl3). Source: Marine-derived fungus Varicosporina ramulosa (Tenerife I., Canary Is., Spain). Pharm: Antialgal. Ref: U. Höller, et al, Acta Crystallogr., Sect. C, 1999, 55, 1310 O O 1

OH

12

O

8

O O

62 9,10-Dihydrocolletodiol Type: Colletodiols macrodilides. C14H22O6 Solid, mp 152–154 °C, [α]D20 = −48° (c = 0.3, CHCl3). Source: Marine-derived fungus Varicosporina ramulosa. Pharm: Antifungal (fungus Eurotium repens, IZD = 2 mm, inhibits growth of fungus Eurotium repens). Ref: U. Höller, et al, EurJOC, 1999, 2949 O O 1

OH

12

O

8

OH O

63 Grahamimycin A1 Type: Colletodiols macrodilides. C14H18O6 Yellow rhomboids, mp 91–92 °C, [α]D22 = −14.7° (c = 0.76, CHCl3). Source: Marine fungus Varicosporina ramulosa. Pharm: Antibacterial (gram-positive and -negative bacteria, weak); anticyanobacterial (blue-green algae, weak), spore germination inhibitor. Ref: R. C. Ronald, et al, Tet. Lett., 1980, 21, 681

1.5 Malyngamides and Related Amides

23

O O

1 5

O

12

O

8

O O

1.5 Malyngamides and Related Amides 64 8-O-Acetylmalyngamide C Type: Malyngamides and related amides. C26H40ClNO6 Oil, [α]D = −32.4° (c = 1.4, EtOH). Source: Cyanobacterium Lyngbya majuscula. Pharm: Cytotoxic (MTT assay, NCI-H460, IC50 = 0.98 μg/mL; neuro-2a, IC50 = 0.91 μg/mL; HCT116, IC50 = 0.8 μg/mL); cytotoxic (disk diffusion soft agar colony formation assay (Valeriote, 2002), C38 and L1210, different ZU < 250); VGSC activation activity (3 μg/mL, toxic, 1 μg/mL, activation 45%, 0.3 μg/mL, inactive). Ref: R. D. Ainslie, et al, JOC, 1985, 50, 2859│H. Gross, et al, Phytochemistry, 2010, 71, 1729 O

O Cl

N H O O

O 9 4 8

O

65 8-O-Acetyl-8-epi-malyngamide C Type: Malyngamides and related amides. C26H40ClNO6 Source: Cyanobacterium Lyngbya majuscula (True Blue Bay, Grenada). Pharm: Cytotoxic (MTT, NCI-H460, IC50 = 4.2 μg/mL; neuro-2a, IC50 = 5.3 μg/mL); cytotoxic (disk diffusion soft agar colony formation assay (Valeriote, 2002), C38 and L1210, different ZU < 250); VGSC blocking activity (3 μg/mL, blocking 71%, 1 μg/mL, blocking 10%, 0.3 μg/mL, inactive). Ref: H. Gross, et al, Phytochemistry, 2010, 71, 1729 O

O Cl

N H O O

O 9 4 8

O

24

1 Polyketides

66 6-O-Acetylmalyngamide F Type: Malyngamides and related amides. C26H40ClNO5 Oil, [α]D25 = −15.1° (c = 3.6, CHCl3). Source: Cyanobacterium Lyngbya majuscula, Cyanobacterium Lyngbya majuscula (shallow-water variety). Pharm: Cytotoxic (MTT, NCI-H460, IC50 = 7.6 μg/mL; neuro-2a, IC50 = 3.1 μg/mL; HCT116, inactive); cytotoxic (disk diffusion soft agar colony formation assay (Valeriote, 2002), C38 and L1210, different ZU = 250); VGSC activation activity (3 μg/mL, activation 19%, 1 μg/mL, inactive); VGSC blocking activity (3 μg/mL, blocking 29%, 1 μg/mL, blocking 15%, 0.3 μg/mL, inactive). Ref: W. H. Gerwick, et al, Phytochemistry, 1987, 26, 1701│H. Gross, et al, Phytochemistry, 2010, 71, 1729 O

O

Cl

N H

O

O

O

67 15-De-O-methylonnamide Type: Malyngamides and related amides. C38H61N5O12 Glassy solid, [α]D23 = +70° (c = 0.1, MeOH). Source: Lithistid sponge Theonella sp. Pharm: Cytotoxic (P388, IC50 = 0.15 μg/mL). Ref: S. Sakemi, et al, JACS, 1988, 110, 4851│S. Matsunaga, et al, Tetrahedron, 1992, 48, 8369 O H N

H 2N NH

OH O N H

4E

6

11

HO

O

O

OH

O

H H N O

O 15

O

H

OH

68 6,7-Dihydroonnamide A Type: Malyngamides and related amides. C39H65N5O12 Source: Lithistid sponges Theonella sp. (yield = 1.3 × 10−4%ww, off Kerama I., Okinawa) and Theonella sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 0.0046 μg/mL; KB, IC50 = 0.0050 μg/mL) (Kobayashi, 1993); cytotoxic (P388, IC50 = 0.04 μg/mL) (Matsunaga, 1992). Ref: S. Matsunaga, et al, Tetrahedron, 1992, 48, 8369│J. Kobayashi, et al, JNP, 1993, 56, 976

1.5 Malyngamides and Related Amides

OH

O 6

OH

O

COOH N H

7

O

25

O

H N

HN

O

O

O

O

NH NH2

69 6,7-Dihydro-11-oxoonnamide A Type: Malyngamides and related amides. C39H63N5O12 Solid, [α]D24 = +39° (c = 0.42, MeOH). Source: Lithistid sponge Theonella sp. (yield = 5.6 × 10−5%ww, off Kerama I., Okinawa). Pharm: Cytotoxic (L1210, IC50 = 0.016 μg/mL; KB, IC50 = 0.023 μg/mL). Ref: J. Kobayashi, et al, JNP, 1993, 56, 976 HO

O

O

N H

6

11

NH2

HN NH

O

O OH

O

H N

O O

O O

O

70 Isomalyngamide A Type: Malyngamides and related amides. C29H45ClN2O6 Colorless oil, [α]D29 = −4.8° (c = 2.9, CH2Cl2), [α]D25 = −5.7° (c = 0.21, MeOH). Source: Cyanobacterium Lyngbya majuscula (Taiwan waters). Pharm: Cytotoxic (MTT assay, MCF7 anti-proliferation IC50 = 4.6 μmol/L; MDA-MB-231 anti-proliferation IC50 = 2.8 μmol/L; MDA-MB-231 inhibition of migration IC50 = 0.060 μmol/L; rat liver α-2,3-sialyltransferase inhibition IC50 = 77.2 μmol/L); lethal toxicity (crayfish Procambarus clarkia, ip, at 250 μg/kg). Ref: Y. Kan, et al, JNP, 2000, 63, 1599│T. T. Chang, et al, Eur. J. Med. Chem. 2011, 46, 3810 O

O

O

O 2'Z

O

N Cl

N

H

O

26

1 Polyketides

71 Isomalyngamide A1 Type: Malyngamides and related amides. C28H43ClN2O4 Pale yellow oil, [α]D25 = −7.3° (c = 0.53, MeOH). Source: Cyanobacterium Lyngbya majuscula (Taiwan waters). Pharm: Cytotoxic (MTT assay, MCF7 anti-proliferation, 20 μmol/L 28%; MDA-MB-231 anti-proliferation IC50 = 12.7 μmol/L; MDA-MB-231 inhibition of migration IC50 = 0.337 μmol/L; rat liver α-2,3-sialyltransferase inhibition IC50 = 65.7 μmol/L). Ref: T. T. Chang, et al, Eur. J. Med. Chem., 2011, 46, 3810 O

O O

N

O O N

Z

O

Cl

72 Isomalyngamide B Type: Malyngamides and related amides. C28H45ClN2O6 [α]D27 = +46.0° (c = 0.4, CH2Cl2). Source: Cyanobacterium Lyngbya majuscula (Taiwan waters). Pharm: Lethal toxic (crayfish Procambarus clarkia, ip, at 500 μg/kg). Ref: Y. Kan, et al, JNP, 2000, 63, 1599 OH

O

O

O

N O

N 2'Z

Cl

H

O

73 Malyngamide 2 Type: Malyngamides and related amides. C25H42ClNO6 Pale yellow oil; [α]D = 1.1° (c = 2.5, CHCl3). Source: Cyanobacterium Lyngbya sordida (Dutchess Is., Papua New Guinea). Pharm: Cytotoxic (MTT assay, H460, IC50 = 27.3 μmol/L); neuro-2a sodium channel activation; anti-inflammatory (NO production assay, LPS-induced RAW macrophage cells, IC50 = 8.0 μmol/L, with only modest cytotoxicity). Ref: K. L. Malloy, et al, JNP 2011, 74, 95

1.5 Malyngamides and Related Amides

27

OH 8R* 15'

O

HO

O 1'

7'S

N H

1

3

6R*

OH

5

H H

14'

9R* 4S*

Cl

O

74 Malyngamide 3 Type: Malyngamides and related amides. C29H48ClNO7 Colorless amorphous powder, [α]D25 = −10.1° (c = 0.36, MeOH). Source: Cyanobacterium Lyngbya majuscula (Cocos Lagoon, Guam). Pharm: Cytotoxic (MCF7, IC50 = 29 μmol/L; HT29, IC50 = 48 μmol/L). Ref: S. P. Gunasekera, et al, JNP, 2011, 74, 871 O N O

Cl

O

O

O

OH O

75 Malyngamide 4 Type: Malyngamides and related amides. C28H43ClN2O5 Source: Cyanobacterium Moorea producens (Jiddah, Saudi Arabia). Pharm: Cytotoxic (several HTCLs, moderate). Ref: L. A. Shaala, et al, Phytochem. Lett., 2013, 6, 183

O

O

O

N O

N Cl

O

76 Malyngamide A N-[2-(Chloromethylene)-6-(2,5-dihydro-4-methoxy-2-oxo-1H-pyrrol-1-yl)-4-methoxy-6oxo-4-hexenyl]-7-methoxy-N-methyl-4-tetradecenamide Type: Malyngamides and related amides. C29H45ClN2O6 Oil, [α]D25 = −6.5° (c = 0.77, CH2Cl2). Source: Cyanobacterium Lyngbya majuscula (shallow-water varieties). Pharm: Antifeedant (dietary preference study using sea hare Stylocheilus longicauda, increases feeding at low concentrations and inhibits feeding at higher concentrations). Ref: J. H. Cardellina, et al, Phytochemistry, 1978, 17, 2091│D. G. Nagle,et al, Mar. Biol., 1998, 132, 267│W. A. Gallimore, JNP, 2000, 63, 1422

28

1 Polyketides

O

O

N

O

O

O

N 2'E

H

O Cl

77 Malyngamide B Type: Malyngamides and related amides. C28H45ClN2O6 Source: Cyanobacteria Lyngbya sp. (Piti Bomb Holes, Guam) and Lyngbya majuscula (shallow-water variety). Pharm: Antifeedant (dietary preference study using sea hare Stylocheilus longicauda, increases feeding at low concentrations and inhibits feeding at higher concentrations); cannabinomimetics (decreasing forskolin-induced cAMP accumulation). Ref: J. H. Cardellina, et al, Phytochemistry, 1978, 17, 2091│D. G. Nagle,et al, Mar. Biol., 1998, 132, 267│W. A. Gallimore, et al, JNP, 2000, 63, 1422│R. Montaser, et al, Chem, Bio, Chem, 2012, 13, 2676 OH

O

N

O

O

O

N 2'E

H

O Cl

78 Malyngamide C Type: Malyngamides and related amides. C24H38ClNO5 Oil, [α]D23.5 = −19.6° (c = 1.4, CHCl3), [α]D = −27.4° (c = 5.8, EtOH). Source: Cyanobacterium Lyngbya majuscula, Cyanobacterium Lyngbya majuscula (shallow-water variety). Pharm: Cytotoxic (MTT, NCI-H460, IC50 = 1.4 μg/mL; neuro-2a, IC50 = 3.1 μg/mL; HCT116, IC50 = 0.2 μg/mL); cytotoxic (HT29, IC50 = 5.2 μmol/L); inhibits bacterial quorum sensing (in a reporter gene assay);VGSC activation activity (3 μg/mL, activation 67%, 1 μg/mL, activation 19%, 0.3 μg/mL, inactive). Ref: J. H. Cardellina, et al, Phytochemistry, 1978, 17, 2091│R. D. Ainslie, et al, JOC, 1985, 50, 2859│ J. C. Kwan, et al, JNP, 2010, 73, 463│H. Gross, et al, Phytochemistry, 2010, 71, 1729 O

O Cl

N H O

O 9 4 8

HO

1.5 Malyngamides and Related Amides

29

79 8-epi-Malyngamide C Type: Malyngamides and related amides. C24H38ClNO5 Light brown oil, [α]D20 = −8° (c = 0.36, MeOH). Source: Cyanobacterium Lyngbya majuscula (Bush Key, Dry Tortugas, Florida). Pharm: Cytotoxic (MTT, NCI-H460, IC50 = 4.5 μg/mL; neuro-2a, IC50 = 10.9 μg/mL); cytotoxic (HT29, IC50 = 15.4 μmol/L); inhibits bacterial quorum sensing (in a reporter gene assay). Ref: H. Gross, et al, Phytochemistry, 2010, 71, 1729│J. C. Kwan, et al, JNP, 2010, 73, 463 O

O

Cl

N H O

O 9 4 8

HO

80 Malyngamide D Type: Malyngamides and related amides. C31H57NO7 [α]D25 = −33° (c = 0.53, CHCl3). Source: Cyanobacterium Lyngbya majuscula (depth of 80–100ft). Pharm: Cytotoxic (KB, ID50 < 30 μg/mL). Ref: J. S. Mynderse, et al, JOC, 1978, 43, 4359│ W. H. Gerwick, et al, Phytochemistry, 1987, 26, 1701 O

O

O

OH

N H

O

HO

OH

81 Malyngamide E N-[2-Hydroxy-2-(4-hydroxy-3,5,5-trimethyl-6-oxo-1-cyclohexen-1-yl)-1-(methoxymethyl) ethyl]-7-methoxy-9-methyl-4-hexadecenamide Type: Malyngamides and related amides. C31H55NO6 [α]D24 = +24.2° (c = 0.6, CHCl3). Source: Cyanobacterium Lyngbya majuscula (depth of 80–100ft). Pharm: Antibacterial (Mycobacterium smegmatis and Bacillus subtilis, mild). Ref: J. S. Mynderse, et al, JOC, 1978, 43, 4359 O O

O OH N H

O

OH

30

1 Polyketides

82 Malyngamide F Type: Malyngamides and related amides. C24H38ClNO4 [α]D25 = +17° (c = 0.9, CHCl3). Source: Cyanobacterium Lyngbya majuscula. Pharm: Cytotoxic (mild). Ref: W. H. Gerwick, et al, Phytochemistry, 1987, 26, 1701 O

O Cl

N H

O

OH

83 Malyngamide H Type: Malyngamides and related amides. C26H41NO4 Yellowish oil, [α]D26 = +26.1° (c = 0.5, CHCl3). Source: Cyanobacterium Lyngbya majuscula. Pharm: VGSC blocking activity (10 μg/mL, blocking 82%, 3 μg/mL, blocking 69%, 1 μg/mL, blocking 53%, 0.3 μg/mL, blocking 9%); ichthyotoxic. Ref: J. Orjala, et al, JNP, 1995, 58, 764│J. S. Todd, et al, Tet. Lett., 1995, 36, 7837│H. Gross, et al, Phytochemistry, 2010, 71, 1729 O

O

O N H

O

84 Malyngamide I Type: Malyngamides and related amides. C26H42ClNO5 [α]D27 = +10.6° (MeOH). Source: Cyanobacterium Lyngbya majuscula (Okinawa). Pharm: LD50 (brine shrimp) = 35 μg/mL, (goldfish) < 10 μg/mL. Ref: J. Orjala, et al, JNP, 1995, 58, 764│J. S. Todd, et al, Tet. Lett., 1995, 36, 7837

O

OH

O

O N Cl

O

85 Malyngamide J Type: Malyngamides and related amides. C33H53NO9 [α]D = +64° (c = 0.1, CHCl3). Source: Cyanobacterium Lyngbya majuscula. Pharm: Cytotoxic (MTT, NCI-H460, IC50 = 10.8 μg/mL; neuro-2a, IC50 = 4.0 μg/mL; HCT116, inactive); cytotoxic (disk diffusion soft agar colony formation assay (Valeriote, 2002), C38 and L1210, different ZU < 250); VGSC blocking activity (3 μg/mL, blocking 44%, 1 μg/mL, blocking 19%,

1.5 Malyngamides and Related Amides

31

0.3 μg/mL, inactive); ichthyotoxic. (fish, LC50 = 7 μg/mL); toxic (brine shrimp, LC50 = 18 μg/mL). Ref: M. Wu, et al, Tetrahedron, 1997, 53, 15983│H. Gross, et al, Phytochemistry, 2010, 71, 1729 O

O

O

N H

O OO OH O O

86 Malyngamide K Dideoxymalyngamide C Type: Malyngamides and related amides. C24H38ClNO3 [α]D = −8.4° (c = 0.3, CHCl3). Source: Cyanobacterium Lyngbya majuscula. Pharm: Cytotoxic (MTT, NCI-H460, IC50 = 1.1 μg/mL; neuro-2a, IC50 = 0.49 μg/mL; HCT116, inactive); cytotoxic (disk diffusion soft agar colony formation assay (Valeriote, 2002), C38 and L1210, different ZU < 250); ichthyotoxic (fish, LC50 = 8 μg/mL); toxic (brine shrimp, LC50 = 40 μg/mL). Ref: M. Wu, et al, Tetrahedron, 1997, 53, 15983; 15986│H. Gross, et al, Phytochemistry, 2010, 71, 1729 O

O

Cl

N H

O 9 4 8

87 Malyngamide L Type: Malyngamides and related amides. C26H42ClNO4 Oil, [α]D = +17.3° (c = 0.1, EtOH). Source: Cyanobacterium Lyngbya majuscula (Curacao). Pharm: Ichthyotoxic (fish, LC50 = 15 μg/mL); toxic (brine shrimp, LC50 = 6 μg/mL). Ref: M. Wu, et al, Tetrahedron, 1997, 53, 15983 O

OH

O N O Cl

32

1 Polyketides

88 Malyngamide M Type: Malyngamides and related amides. C26H40ClNO3 [α]D = −35° (c = 0.06, MeOH). Source: Red alga Gracilaria coronopifolia. Pharm: Cytotoxic (mus neuroblastoma cells, IC50 > 20 μmol/L). Ref: Y, Kan, et al, JNP, 1998, 61, 152

HO

O

O

N Cl

89 Malyngamide N Deacetoxystylocheilamide Type: Malyngamides and related amides. C26H40ClNO4 [α]D25 = 11.3° (c = 15.7, MeOH). Source: Red alga Gracilaria coronopifolia, sea hare Stylocheilus longicauda (Hawaii). Pharm: Cytotoxic (mus neuroblastoma cells, IC50 = 4.9 μg/mL). Ref: A. F. Rose et al, JACS, 1978, 100, 7665│Y, Kan, et al, JNP, 1998, 61, 152 O

7

O

O N

6

2 3

Cl

O

90 Malyngamide O Type: Malyngamides and related amides. C25H42ClNO5 Pale yellow oil, [α]D = −55.6° (c = 0.018, MeOH). Source: Cyanobacterium Lyngbya majuscula. Pharm: Cytotoxic (P388, IC50 = 2 μg/mL; A549 and HT29, moderate). Ref: W. A. Gallimore, et al, JNP, 2000, 63, 1022; 1422

O 6

O

O

O

N Cl

O

91 Malyngamide R Type: Malyngamides and related amides. C30H47ClN2O7 Pale yellow oil, [α]D25 = +2.0° (c = 0.9, MeOH). Source: Cyanobacterium Lyngbya majuscula (Madagascarr). Pharm: Toxic (brine shrimp, LD50 = 18 ppm, MeOH, c = 0.8). Ref: K. E. Milligan, et al, JNP, 2000, 63, 965

1.5 Malyngamides and Related Amides

33

O HO O

O

N

O

O

N O

Cl

92 Malyngamide X Type: Malyngamides and related amides. C33H57N3O7 Pale yellow oil, [α]D27 = −6.8° (c = 0.18, CHCl3). Source: Sea hare Bursatella leachii. Pharm: Cytotoxic (moderate). Ref: S. Suntornchashwej, et al, Chem. Asian J., 2007, 2, 114 O

O

OH

H N

N

O N

O

O O

93 4Z-Onnamide A Type: Malyngamides and related amides. C39H63N5O12 Solid, [α]D23 = +81° (c = 0.59, MeOH). Source: Lithistid sponge Theonella sp. (yield = 7.9 × 10−5%ww, off Kerama I., Okinawa). Pharm: Cytotoxic (L1210, IC50 = 0.0015 μg/mL; KB, IC50 = 0.0029 μg/mL). Ref: J. Kobayashi, et al, JNP, 1993, 56, 976

HO

O

HO

O 4

NH2

HN

N H O

O

OH

O

H N

O

NH O

O

O

94 Onnamide A Type: Malyngamides and related amides. C39H63N5O12 Pale yellow solid, [α]D20 = +99.1° (c = 5.5, MeOH). Source: Lithistid sponges Theonella swinhoei and Theonella sp. (yield = 8.8 × 10−4% ww, Kerama I., Okinawa). Pharm: Induces activation of p38 kinase and JNK; antiviral; cytotoxic (L1210, IC50 = 0.002 μg/mL; KB, IC50 = 0.0036 μg/mL); cytotoxic (P388, IC50 = 0.01 μg/mL). Ref: S. Sakemi, et al, JACS, 1988, 110, 4851│S. Matsunaga, et al, Tetrahedron, 1992, 48, 8369│J. Kobayashi, et al, JNP, 1993, 56, 976│K.-H. Lee,et al, Cancer Sci. 2005, 96, 357│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev)

34

1 Polyketides

O

OH

H N

H 2N

O

N H

NH

6

4E

11

HO

O

O

OH

H H N

O 15

22

O

O

O

H

O

95 Onnamide B Type: Malyngamides and related amides. C37H61N5O12 Glassy solid, [α]D23 = +61.8° (c = 0.5, MeOH). Source: Lithistid sponge Theonella sp. Pharm: Cytotoxic (P388, IC50 = 0.13 μg/mL). Ref: S. Matsunaga, et al, Tetrahedron, 1992, 48, 8369 OH

O

O

O

OH

O

COOH

O

H N

N H O

H N

NH2

O O

HN

96 Onnamide C Type: Malyngamides and related amides. C39H61N5O14 Glassy solid, [α]D23 = +45.4° (c = 0.2, MeOH). Source: Lithistid sponge Theonella sp. Pharm: Cytotoxic (P388, IC50 = 0.07 μg/mL). Ref: S. Matsunaga, et al, Tetrahedron, 1992, 48, 8369 O

O O

O

OH

O COOH

HO H N

N H

O

H N

O O O

O

NH2 HN

97 Onnamide D Type: Malyngamides and related amides. C38H63N5O11 Glassy solid, [α]D23 = +51.4° (c = 0.1, MeOH). Source: Lithistid sponge Theonella sp. Pharm: Cytotoxic (P388, IC50 = 0.02 μg/mL). Ref: S. Matsunaga, et al, Tetrahedron, 1992, 48, 8369

1.5 Malyngamides and Related Amides

35

OH O O

OH

O

O

H N O

COOH N H

OH

O

H N

NH2

HN

98 Onnamide F Type: Malyngamides and related amides. C31H51NO10 Pale yellow solid, [α]D22 = +22° (c = 0.16, MeOH). Source: Sponge Trachycladus laevispirulifer (South Australia). Pharm: Nematocidal (potent); antifungal. Ref: D. Vuong, et al, JNP, 2001, 64, 640 OH COOH

O

OH

O

O

H N

O

O

O

99 11-Oxoonnamide A Type: Malyngamides and related amides. C39H61N5O12 Solid, [α]D23 = +90° (c = 0.24, MeOH). Source: Lithistid sponge Theonella sp. (yield = 3.0 × 10−5%ww, off Kerama I., Okinawa). Pharm: Cytotoxic (L1210, IC50 = 0.0092 μg/mL; KB, IC50 = 0.013 μg/mL). Ref: J. Kobayashi, et al, JNP, 1993, 56, 976 O

HO

O

N H 11

NH2

HN NH

O

O

O OH

O

O

H N

O O

O

100 17-Oxoonnamide B Type: Malyngamides and related amides. C37H59N5O12 Glassy solid, [α]D23 = +59.7° (c = 0.2, MeOH). Source: Lithistid sponge Theonella sp. Pharm: Cytotoxic (P388, IC50 = 0.10 μg/mL). Ref: S. Matsunaga, et al, Tetrahedron, 1992, 48, 8369

36

1 Polyketides

O OH O O

O

O

COOH

O

H N

N H O

O

O

H N

NH2

HN

101 Stylocheilamide Acetoxycrenulide Type: Malyngamides and related amides. C28H44ClNO6 Non-cryst., [α]D28 = +10.6° (c = 28.2, MeOH). Source: Brown alga Dictyota crenulata, sea hares Stylocheilus longicauda (Hawaii) and Aplysia vaccaria. Pharm: Cytotoxic (mus neuroblastoma cells, IC50 = 7.1 μg/mL). Ref: A. F. Rose, et al, JACS, 1978, 100, 7665│J. S. Todd, et al, Tet. Lett., 1995, 36, 7837 (Struct. revised)│Y, Kan, et al, JNP, 1998, 61, 152 O

O

O

O

O N O

Cl

102 Theopederin A Type: Malyngamides and related amides. C27H45NO10 [α]D = +88.1° (c = 0.1, CHCl3). Source: Lithistid sponges Theonella swinhoei (off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE) and Theonella sp. Pharm: Cytotoxic (P388, IC50 = 0.05 ng/mL); antineoplastic (P388, 0.1 mg/kg/day, treated on days 1,2, and 4–6, ip, T/C = 205%). Ref: N. Fusetani, et al, JOC, 1992, 57, 3828│S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697

H

21

O O O OH

O H H N O

OH

O

O

H

O

103 Theopederin B Type: Malyngamides and related amides. C28H47NO11 [α]D = +49.1° (c = 0.03, CHCl3). Source: Lithistid sponges Theonella swinhoei (yield = 2.1 × 10−5%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE) and Theonella sp. Pharm: Cytotoxic (P388, IC50 = 0.1 ng/mL); antineoplastic (P388, 0.4 mg/kg/day, treated on days 1,2, and 4–6, ip, T/C = 173%); induces activation of p38 kinase and JNK.

1.5 Malyngamides and Related Amides

37

Ref: N. Fusetani, et al, JOC, 1992, 57, 3828│S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) O O

R

O

O H H N

O OH

OH

O

O

O

H

O

104 Theopederin C Type: Malyngamides and related amides. C27H43NO10 [α]D = +172° (c = 0.03, CHCl3). Source: Lithistid sponges Theonella swinhoei (yield = 2.8 × 10−5%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE) and Theonella sp. (Japan waters). Pharm: Cytotoxic (P388, IC50 = 0.7 ng/mL). Ref: N. Fusetani, et al, JOC, 1992, 57, 3828│S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697

H O O

O H H N

O OH

O

O

O

O

H

O

105 Theopederin D Type: Malyngamides and related amides. C26H41NO10 [α]D = +80° (c = 0.04, CHCl3). Source: Lithistid sponge Theonella sp. (Japan waters). Pharm: Cytotoxic (P388, IC50 = 1.0 ng/mL); antineoplastic (mus). Ref: N. Fusetani, et al, JOC, 1992, 57, 3828│P. J. Kocienski, et al, Synlett., 1998, 869; 1432 H O O

O H H N

O OH

O

O

O

H

O

O

38

1 Polyketides

106 Theopederin E Type: Malyngamides and related amides. C22H37NO9 [α]D = +136.7° (c = 0.03, CHCl3). Source: Lithistid sponges Theonella swinhoei (yield = 1.6 × 10−5%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE) and Theonella sp. Pharm: Cytotoxic (P388, IC50 = 9.0 ng/mL); antineoplastic (mus). Ref: N. Fusetani, et al, JOC, 1992, 57, 3828│J. S. Simpson, et al, JNP, 2000, 63, 704│S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697 HO O

O

H H N

O OH

O

O

O

H

O

107 Theopederin F Type: Malyngamides and related amides. C27H47NO10 [α]D24 = +32° (c = 0.3, MeOH). Source: Lithistid sponge Theonella swinhoei (yield = 5.7 × 10−6%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE). Pharm: Antifungal (inhibits growth of wild type Saccharomyces cerevisiae, 10 pg/disk, IZD = 11 mm; erg6mutant, 1 μg/disk, IZD = 12 mm); cytotoxic (P388, IC50 = 0.28 nmol/L = 15 ng/mL). Ref: S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697 OH OH

6

O

O

O

O OH

H N H

O H O

O

108 Theopederin G Type: Malyngamides and related amides. C30H47NO11 [α]D24 = +45° (c = 0.12, MeOH). Source: Lithistid sponge Theonella swinhoei (yield = 2.1 × 10−6%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE). Pharm: Antifungal; cytotoxic (P388, lC50 < 90 ng/mL). Ref: S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697 OH HOOC

O

OH

O

OH

H N O O

O

O

1.5 Malyngamides and Related Amides

39

109 Theopederin H Type: Malyngamides and related amides. C30H45NO11 [α]D24 = +60° (c = 0.02, MeOH). Source: Lithistid sponge Theonella swinhoei (yield = 4.3 × 10−7%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE). Pharm: Antifungal; cytotoxic (P388, lC50 < 90 ng/mL). Ref: S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697 O HOOC

O

OH

O

OH

H N O O

O

O

110 Theopederin I Type: Malyngamides and related amides. C32H49NO11 [α]D24 = +54° (c = 0.08, MeOH). Source: Lithistid sponge Theonella swinhoei (yield = 1.4 × 10−6%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE). Pharm: Antifungal; cytotoxic (P388, lC50 < 90 ng/mL). Ref: S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697 OH HOOC 3

O

OH

OH

O

H N

O O

O

O

111 Theopederin J Type: Malyngamides and related amides. C34H51NO11 [α]D24 = +48° (c = 0.04, MeOH). Source: Lithistid sponge Theonella swinhoei (yield = 7.1 × 10−7%ww, off Kerama I., Ryukyu Archipelago, Japan, 26ʹʹ13ʹN, 127ʹʹ23ʹE). Pharm: Antifungal; cytotoxic (P388, lC50 < 90 ng/mL). Ref: S. Tsukamoto, et al, Tetrahedron, 1999, 55, 13697 O HOOC 3

O

OH

OH

O

H N

O O

O

O

40

1 Polyketides

112 Theopederin K Discalamide A Type: Malyngamides and related amides. C32H49NO11 Amorph. powder, [α]D21 = +90.3° (c = 0.43, MeOH). Source: Lithistid sponge Discodermia sp. (four specimens, off north coast of Honduras, depth of 121–125m, using Johnson-Sea-Link submersible). Pharm: Cytotoxic (P388, with IC50 = 0.1 nmol/L; A549, IC50 = 1.5 nmol/ L). Ref: G. K. Paul, et al, JNP, 2002, 65, 59│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) O 17

6

O

O

O

O

H N H

OH

O H O

O

HO

O

113 Theopederin L Discalamide B Type: Malyngamides and related amides. C31H47NO11 Amorph. powder, [α]D21 = +34° (c = 0.05, MeOH). Source: Lithistid sponge Discodermia sp. (four specimens, off north coast of Honduras, depth of 121–125m, using Johnson-Sea-Link submersible). Pharm: Cytotoxic (P388, with IC50 = 7.3 nmol/L; A549, IC50 = 3.2 nmol/L). Ref: G. K. Paul, et al, JNP, 2002, 65, 59│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) OH 17

6

O

O OH

O

O

H N H

O H O

O

HO

O

1.6 Ansamycins 114 Rifamycin S Type: Ansamycins. C37H45NO12 Yellow-orange cryst. (MeOH), mp 179–181 °C (dec), [α]D20 = +476° (c = 0.1, MeOH). Source: Marine-derived bacterium Salinispora arenicola YM23-082. Pharm: Antibacterial (Staphylococcus aureus IFO 12732, MIC = 0.0056 μg/mL; Bacillus subtilis IFO 3134, MIC = 1.4 μg/mL; Cytophaga marinoflava IFO 14170, MIC = 12.3 μg/mL; Escherichia coli IFO 3301, MIC > 200 μg/mL;

1.7 Other Polyenes Antibiotics

41

Pseudomonas aeruginosa IFO 3446, MIC > 200 μg/mL); antifungal (Candida albicans IFO 1060, MIC > 200 μg/mL). Ref: S. K. Arora, et al, J. Antibiot., 1992, 45, 428│ S. Matsuda, et al, J. Antibiot., 2009, 62, 519

HO O O

OH OH

O

O O NH

O O

O O

115 Salinisporamycin Type: Ansamycins. C33H43NO9 Amorph. solid, [α]D = +36° (c = 0.7, MeOH). Source: Marine-derived actinomycete Salinispora arenicola CNH643. Pharm: Cytotoxic (A549, IC50 = 3 μg/mL); antibacterial (Staphylococcus aureus IFO 12732, MIC = 0.46 μg/mL; MIC = 4.1 μg/mL; Bacillus subtilis IFO 3134, Cytophaga marinoflava IFO 14170, MIC > 200 μg/mL; Escherichia coli IFO 3301, MIC > 200 μg/mL; Pseudomonas aeruginosa IFO 3446, MIC > 200 μg/mL); antifungal (Candida albicans IFO 1060, MIC > 200 μg/mL). Ref: S. Matsuda, et al, J. Antibiot., 2009, 62, 519 H O

OH O

OH

OH

O N H

O

HO O

1.7 Other Polyenes Antibiotics 116 Antibiotic ML 449 Type: Other polyenes antibiotics. C29H39NO3 Source: Marine-derived streptomycete Streptomyces sp. MP39-85. Pharm: Antifungal (Micrococcus luteus, Candida albicans, Candida glabrata). Ref: H. Jørgensen, et al, Appl. Environ. Microbiol., 2010, 76, 283

42

1 Polyketides

O HO

NH

HO

117 Bahamaolide A Type: Other polyenes antibiotics. C39H64O11 Source: Marine-derived streptomycete Streptomyces sp. (sediment, North Cat Cay, Bahamas). Pharm: Isocitrate lyase inhibitor (Candida albicans, strong). Ref: D. -G. Kim, et al, JNP, 2012, 75, 959 O

OH 1

12E

O

OH

OH

OH

OH

OH

OH

OH

OH

118 Symbiodinolide Type: Other polyenes antibiotics. C137H233NO57S Oil, [α]D20 = +9.6° (c = 0.4, CHCl3). Source: Dinoflagellate Symbiodinium sp. Pharm: Voltage-dependent N-type Ca2+ channel activator (IC50 = 7 nmol/L, MMOA: cyclooxygenase 1 inhibitor). Ref: M. Kita, et al, Tetrahedron, 2007, 63, 6241 OH

OH

OH

O

O OH

OH

OH

HO OH

OH

OH

O

O

HO

S O

HO O

OH

OH

OH

O

OH

OH

OH

OH

OH

HO OH

OH

H HO

H

O

OH

O OH

OH

OH

O

OH

H OH HO

OH

OH H O

HO OH O

OH

OH H

H O

OH HO

OH OH OH

OH

NH

OH

1.9 Anguyclines

43

1.8 Linear Tetracyclines 119 Seragakinone A Type: Linear tetracyclines. C26H26O12 Pale yellow amorph. solid, [α]D26 = +146° (c = 1.0, MeOH). Source: An unidentified marine-derived fungus K063 from red alga Ceratodictyon spongiosum (Okinawa). Pharm: Antibacterial (Staphylococcus aureus 209P, MIC = 10 μg/mL, Micrococcus luteus IFM 2066, MIC = 20 μg/mL, Corynebacterium xerosis IFM 2057, MIC = 20 μg/mL, Bacillus subtilis, MIC = 41 μg/mL); antifungal (Candida albicans ATCC 90028, MIC = 83 μg/mL). Ref: H. Shigemori, et al, Tetrahedron, 1999, 55, 14925│A. Takada, et al, Angew. Chem., Int. Ed., 2011, 50, 2297

OH O

O

MeO

OH O OH

O

OH

OH OH O

1.9 Anguyclines 120 Antibiotic SS-228Y Type: Anguyclines. C19H14O6 Yellow-brown powder, mp 256–266 °C (dec), [α]D = −85°, (c = 1.0, Me2CO). Source: Marine fungi Chainia spp. (shallow sea mud). Pharm: Antibacterial (gram-positive bacteria); dopamine β-hydroxylase inhibitor; LD50 (mus, ivn) = 6–12 mg/kg, LD50 (mus, ipr) = 1.5–5.5 mg/kg. Ref: T. Okazaki, et al, Antibiotics, 1975, 28, 176│T. Kitahara, et al, J. Antibiotics, 1975, 28, 280│ N. Imamura, et al, J. Antibiotics, 1982, 35, 602│Y. Tamura, et al, JOC, 1985, 50, 2273 O O

HO OH

OH

O

121 Grincamycin A Antibiotic A300 Type: Anguyclines. C49H62O18 Yellow powder or pale red powder, mp 153–158 °C, [α]D22 = −48° (c = 0.1, CHCl3), [α]D25 = −61° (c = 0.33, CHCl3). Source: Marine-derived streptomycete Streptomyces lusitanus SCSIO LR32 (deep sea sediment, South China Sea). Pharm: Cytotoxic (B16, IC50 = 1.1 μmol/L, control 5-FU,

44

1 Polyketides

IC50 = 33 μmol/L, control Doxorubicin, IC50 = 1.7 μmol/L; HepG2, IC50 = 5.3 μmol/L, 5-FU, IC50 = 34 μmol/L, Doxorubicin, IC50 = 7.1 μmol/L; SW1990, IC50 = 6.4 μmol/L, 5-FU, IC50 = 45 μmol/L, Doxorubicin, IC50 = 5.3 μmol/L; HeLa, IC50 = 5.3 μmol/L, 5-FU, IC50 = 43 μmol/L, Doxorubicin, IC50 = 11 μmol/L; NCI-H460, IC50 = 11 μmol/L, 5-FU, IC50 = 29 μmol/L, Doxorubicin, IC50 = 6.9 μmol/L; MCF7, IC50 = 2.1 μmol/L, 5-FU, IC50 = 35 μmol/L); antimicrobial. Ref: H. Huang, et al, JNP, 2012, 75, 202 O O HO

O

OH O

O OH

O

O O

OH

O

O

O O O

O

122 Grincamycin B Type: Anguyclines. C49H62O18 Red solid, [α]D25 = −18° (c = 0.4, CHCl3). Source: Marine-derived streptomycete Streptomyces lusitanus SCSIO LR32 (deep sea sediment, South China Sea). Pharm: Cytotoxic (B16, IC50 = 2.1 μmol/L, control 5-FU, IC50 = 33 μmol/L, control Doxorubicin, IC50 = 1.7 μmol/L; HepG2, IC50 = 8.5 μmol/L, 5-FU, IC50 = 34 μmol/L, Doxorubicin, IC50 = 7.1 μmol/L; SW1990, IC50 = 11 μmol/L, 5-FU, IC50 = 45 μmol/L, Doxorubicin, IC50 = 5.3 μmol/L; HeLa, IC50 = 6.4 μmol/L, 5-FU, IC50 = 43 μmol/L, Doxorubicin, IC50 = 11 μmol/L; NCI-H460, IC50 > 100 μmol/L, 5-FU, IC50 = 29 μmol/L, Doxorubicin, IC50 = 6.9 μmol/L; MCF7, IC50 = 12 μmol/L, 5-FU, IC50 = 35 μmol/L). Ref: H. Huang, et al, JNP, 2012, 75, 202 O

OH

COOH

O

O OH

O

O

O

OH

O

O O

O O

O

O

1.9 Anguyclines

45

123 Grincamycin C Type: Anguyclines. C37H44O14 Red amorph. solid, [α]D25 = −41° (c = 0.73, CHCl3). Source: Marine-derived streptomycete Streptomyces lusitanus SCSIO LR32 (deep sea sediment, South China Sea). Pharm: Cytotoxic (HepG2, IC50 = 31 μmol/L, control 5-FU, IC50 = 34 μmol/L, control Doxorubicin, IC50 = 7.1 μmol/L; SW1990, IC50 = 31 μmol/L, 5-FU, IC50 = 45 μmol/L, Doxorubicin, IC50 = 5.3 μmol/L; MCF7, IC50 = 11 μmol/L, 5-FU, IC50 = 35 μmol/L). Ref: H. Huang, et al, JNP, 2012, 75, 202

O

O

O O

HO O

OH

HO O

O

COOH O

HO

124 Grincamycin D Type: Anguyclines. C43H50O16 Brown-yellow amorph. solid, [α]D25 = +70° (c = 0.55, CHCl3). Source: Marine-derived streptomycete Streptomyces lusitanus SCSIO LR32 (deep sea sediment, South China Sea). Pharm: Cytotoxic (B16, IC50 = 9.7 μmol/L, control 5-FU, IC50 = 33 μmol/L, control Doxorubicin, IC50 = 1.7 μmol/L; HepG2, IC50 = 9.7 μmol/L, 5-FU, IC50 = 34 μmol/L, Doxorubicin, IC50 = 7.1 μmol/L; SW1990, IC50 = 22 μmol/L, 5-FU, IC50 = 45 μmol/L, Doxorubicin, IC50 = 5.3 μmol/L; HeLa, IC50 = 12 μmol/L, 5-FU, IC50 = 43 μmol/L, Doxorubicin, IC50 = 11 μmol/L; NCI-H460, IC50 = 30 μmol/L, 5-FU, IC50 = 29 μmol/L, Doxorubicin, IC50 = 6.9 μmol/L; MCF7, IC50 = 6.1 μmol/L, 5-FU, IC50 = 35 μmol/L). Ref: H. Huang, et al, JNP, 2012, 75, 202 O

OH

COOH

O

O OH

O

O

O

O

O

O

O

O

O

125 Grincamycin E Type: Anguyclines. C49H60O17 Yellowish powder, [α]D25 = −112° (c = 0.17, CHCl3). Source: Marine-derived streptomycete Streptomyces lusitanus SCSIO LR32 (deep sea sediment, South China Sea). Pharm: Cytotoxic (B16, IC50 = 5.4 μmol/L, control 5-FU,

46

1 Polyketides

IC50 = 33 μmol/L, control Doxorubicin, IC50 = 1.7 μmol/L; HepG2, IC50 = 11 5-FU, IC50 = 34 μmol/L, Doxorubicin, IC50 = 7.1 μmol/L; SW1990, IC50 = 16 5-FU, IC50 = 45 μmol/L, Doxorubicin, IC50 = 5.3 μmol/L; HeLa, IC50 = 11 5-FU, IC50 = 43 μmol/L, Doxorubicin, IC50 = 11 μmol/L; MCF7, IC50 = 8.7 control 5-FU, IC50 = 35 μmol/L). Ref: H. Huang, et al, JNP, 2012, 75, 202 O

OH

O

O OH

O

O

O

OH

O

μmol/L, μmol/L, μmol/L, μmol/L,

O

O

O

O

O O

O

126 Grincamycin F Type: Anguyclines. C57H66O20 Dark red powder, [α]D25 = +110° (c = 0.09, CHCl3MeOH, 9:1). Source: Marine-derived streptomycete Streptomyces lusitanus SCSIO LR32 (deep sea sediment, South China Sea). Pharm: Cytotoxic (B16, HepG2, SW1990, HeLa and NCI-H460, IC50 > 100 μmol/L; MCF7, IC50 = 19 μmol/L, control 5-FU, IC50 = 35 μmol/L). Ref: H. Huang, et al, JNP, 2012, 75, 202 HO

O O

O HO

O OH O

O O

O

O

OH

O

O O

O

O

O

O

127 Marmycin A Type: Anguyclines. C26H23NO4 Red needles (THF/pentane), mp 257–259 °C (dec), [α]D20 = +520° (c = 0.05, THF). Source: Marine-derived streptomycete Streptomyces sp. Pharm: Cytotoxic (HCT116, IC50 = 60.5 nmol/L); cytotoxic (panel of 12 hmn tumor cell lines (breast, prostate, colon, lung, and leukemia), after 72h drug exposure, mean IC50 = 0.022 μmol/L, range IC50 = 0.007–0.058 μmol/L). cytotoxic

1.9 Anguyclines

47

(induction of modest apoptosis and arrest in G1 phase of cell cycle: dose 20 nmol/L, 4.4% apoptosis, 2.9% < G1, 48% G1, 41% S, 7.3% G2, 0.8% > G2; dose 60 nmol/L, 6.9% apoptosis, 4.1% < G1, 50% G1, 39% S, 4.5% G2, 1.9% > G2; dose 200 nmol/L, 5.8% apoptosis, 2.4% < G1, 55% G1, 35% S, 8.0% G2, 0.6% > G2). Ref: G. D. A. Martin, et al, JNP, 2007, 70, 1406 O 11

O O

HO N H

128 Marmycin B Type: Anguyclines. C26H22ClNO4 Pink needles (THF/pentane), mp 291–293 °C (dec), [α]D20 = +600° (c = 0.1, THF). Source: Marine-derived streptomycete Streptomyces sp. Pharm: Cytotoxic (HCT116, IC50 = 1.09 μmol/L); cytotoxic (panel of 12 hmn tumor cell lines (breast, prostate, colon, lung and leukemia), after 72h drug exposure, mean IC50 = 3.5 μmol/L, range IC50 = 1.0–4.4 μmol/L). Ref: G. D. A. Martin, et al, JNP, 2007, 70, 1406 Cl

O

11

O O

HO N H

129 Mayamycin Type: Anguyclines. C26H25NO7 Dark brown powder. Source: Marine-derived streptomycete Streptomyces sp. HB202 from sponge Halichondria panicea (Baltic Sea). Pharm: Antibacterial (Bacillus subtilis, IC50 = 8.0 μmol/L, control Chloramphenicol, IC50 = 9.0 μmol/L; Brevibacterium epidermidis, IC50 = 7.45 μmol/L, control Tetracycline, IC50 = 13.9 μmol/L; Dermabacter hominis, IC50 = 8.4 μmol/L, Tetracycline, IC50 = 1.2 μmol/L; Klebsiella pneumonia, IC50 = 2.5 μmol/L; Propionibacterium acnes, IC50 = 31.2 μmol/L, Chloramphenicol, IC50 = 1.0 μmol/L; Pseudomonas aeruginosa, IC50 = 2.5 μmol/L, Chloramphenicol, IC50 = 27.3 μmol/L; Staphylococcus aureus, IC50 = 2.5 μmol/L, control Moxifloxacin, IC50 = 7.5 μmol/L; Staphylococcus aureus MRSA, IC50 = 1.25 μmol/L; Staphylococcus epidermidis, IC50 = 0.31 μmol/L; Staphylococcus lentus, IC50 = 8.0 μmol/L, Chloramphenicol, IC50 = 2.3 μmol/L; Xanthomonas campestris, IC50 = 30.0 μmol/L, Chloramphenicol,

48

1 Polyketides

IC50 = 3.6 μmol/L); cytotoxic (HepG2, IC50 = 0.2 μmol/L, control Tamoxifen, IC50 = 23.4 μmol/L; HT29, IC50 = 0.3 μmol/L, Tamoxifen, IC50 = 38.6 μmol/L; GXF0.052 μmol/L; LXF-529L, 251L, IC50 = 0.2 μmol/L, control ADM, IC50 = IC50 = 0.16 μmol/L, ADM, IC50 = 0.052 μmol/L; MAXF-401NL, IC50 = 0.29 μmol/L, ADM, IC50 = 0.052 μmol/L; MEXF-462NL, IC50 = 0.13 μmol/L, ADM, IC50 = 0.052 μmol/L; PAXF-1657L, IC50 = 0.15 μmol/L, ADM, IC50 = 0.052 μmol/L; RXF486L, IC50 = 0.33 μmol/L, ADM, IC50 = 0.052 μmol/L). Ref: I. Schneemann, et al, JNP, 2010, 73, 1309 HO O

OH

O

OH HO N OH

130 Urdamycin E Type: Anguyclines. C44H58O17S Red amorph. solid. Source: Marine-derived streptomycete Streptomyces sp. from sponge Xestospongia sp. (Sichang I., Chonburi, Thailand). Pharm: Antimalarial (Plasmodium falciparum K1, potent); antituberculosis (Mycobacterium tuberculosis). Ref: K. Supong, et al, Phytochem. Lett., 2012, 5, 651 OO O

O OH

OH O

5

OH O

OH S

O OH

O

OO OH OH

131 Urdamycinone G Type: Anguyclines. C26H26O9S Source: Marine-derived streptomycete Streptomyces sp. from sponge Xestospongia sp. (Sichang I., Chonburi, Thailand). Pharm: Antimalarial (Plasmodium falciparum K1, potent); antituberculosis (Mycobacterium tuberculosis). Ref: M. Sezaki, et al, Tetrahedron, 1970, 26, 5171│K. Supong, et al, Phytochem. Lett., 2012, 5, 651

49

1.10 Palytoxins Nonmacrolide Polyethers

O

O

OH

O

OH S

OH

HO

O

OH

1.10 Palytoxins Nonmacrolide Polyethers 132 Palytoxin PTX Type: Palytoxins nonmacrolide polyethers. C129H223N3O54 Sol. Py, DMSO, H2O; fairly sol. MeOH, EtOH; poorly sol. CHCl3, Me2CO. Source: Zoanthids Polythoa toxica, Polythoa tuberculosa and Polythoa sp. (Ishigaki I., Okinawa). Pharm: Toxic (the most lethal non-proteinous toxin); NaK-ATPase inhibitor; sperm motility inhibitor; cardiotoxic and haemolytic agent; coronary vasoconstrictor; LD50 (mus, iv) = 0.45 mg/kg, LD50 (mus, ipr) = 0.05 mg/kg, LD50 (crab) = 62.5 ng/kg. Ref: R. E. Moore, et al, Science, 1971, 172, 495│D. Uemura, et al, Tetrahedron, 1985, 41, 1007│ E. M. Suh, et al, JACS., 1994, 116, 11 205│Y. Kan, et al, Tet. Lett., 2001, 42, 3197 OH O

O

OH

OH

OH

OH

HO

O

OH

OH

O OH

HO

OH OH OH

OH [R6] NH2

OH OH

[R1]

OH

OH

O

NH

O

HO

OH

HO O

OH [R2] O

[R3]

OH OH

OH

O

HN

O

OH

HO OH

OH

O

HO

OH [R4] OH O OH HO [R5]

OH OH OH

OH OH

OH OH

OH

50

1 Polyketides

1.11 Amphidinols Nonmacrolide Polyethers 133 Amphidinol 1 Amphidinol Type: Amphidinols nonmacrolide polyethers. C73H126O27S Pale yellow solid (Na salt), [α]D23 = −25° (c = 0.18, MeOH). Source: Dinoflagellate Amphidinium klebsii. Pharm: Antifungal (Aspergillus niger, 6 μg/disk, growth inhibiting activity was 3 times that of amphotericin B); hemolytic (mouse blood cells, hemolytic activity was 120 times that of control saponin). Ref: M. Satake, et al, JACS, 1991, 113, 9859 OH HO HO

OH

OH O O OH

OH

HO

OH OH OH

OH

OH

O HO OH

OH

S O O

3

OH

OH

OH

OH

134 Amphidinol 2 Type: Amphidinols nonmacrolide polyethers. C77H122O25 Pale yellow solid, [α]D25 = +2.1° (c = 0.1, MeOH). Source: Dinoflagellate Amphidinium klebsii. Pharm: Hemolytic (hmn erythrocytes, EC50 = 7.3 nmol/L, about several hundred times more efficacious than control Saponin); antifungal (Aspergillus niger, 6 μg/disk); algicide; toxic (primary rat hepatocytes, IC50 = 6.4 μmol/L). Ref: G. K. Paul, et al, Tet. Lett., 1995, 36, 6279│X. M. Qi, et al, Toxicon, 2007, 50, 278 OH HO OH

OH

OH

OH OH

O OH

OH

OH

OH

O HO

OH HO

HO

OH HO

OH 1

O OH OH OH

OH

1.11 Amphidinols Nonmacrolide Polyethers

51

135 Amphidinol 5 Type: Amphidinols nonmacrolide polyethers. C72H122O24 Pale yellow solid, [α]D26 = −52° (c = 0.1, MeOH). Source: Dinoflagellate Amphidinium klebsii. Pharm: Disrubts cholesterol-containing lipid membranes. Ref: G. K. Paul, et al, J. Mar. Biotechnol., 1997, 5, 124 OH HO OH

OH

OH OH

O OH

OH

O HO

OH

OH

OH OH

OH

HO OH OH OH OH

OH OH

OH

136 Amphidinol 6 Type: Amphidinols nonmacrolide polyethers. C70H120O24 Amorph. solid, [α]D27 = −29.9° (c = 0.08, MeOH). Source: Dinoflagellate Amphidinium klebsii. Pharm: Disrubts cholesterol-containing lipid membranes. Ref: G. K. Paul, et al, J. Mar. Biotechnol., 1997, 5, 124 OH HO OH

OH

OH OH

O OH

OH

O HO

OH

OH OH

HO OH OH OH

OH OH OH OH

OH OH

52

1 Polyketides

137 Amphidinol 17 AM17 Type: Amphidinols nonmacrolide polyethers. C63H110O24S Pale yellow semisolid, [α]D25 = −6° (c = 0.1, MeOH). Source: Dinoflagellate Amphidinium carterae. Pharm: Hemolytic (hmn red blood cells, EC50 = 4.9 μmol/L). Ref: Y. Meng, et al, JNP, 2010, 73, 409 OH

OH

OH

OH

OH OH

OH OH

OH

OH

OH HO OH

O

OH

OH

O

OH OH

OH

O O

S

OH O

1.12 Other Nonmacrolide Polyethers 138 (65E)-chloro-KmTx1 Type: Other nonmacrolide polyethers. C69H125ClO24 Source: Dinoflagellate Karlodinium veneficum CCMP 2936 (culture, Delaware Bays, USA). Pharm: Haemolytic. Ref: R. M. Van Wagoner, et al, Tet. Lett., 2008, 49, 6457 OH OH

OH OH

OH OH

HO

OH

OH

OH 3

OH

OH

OH

OH

HO OH

OH OH

O

OH OH

65E

O

9

Cl

OH

OH

139 (64E)-Chloro-KmTx3 Type: Other nonmacrolide polyethers. C68H123ClO24 Source: Dinoflagellate Karlodinium veneficum CCMP 2936 (culture, Delaware Bays, USA). Pharm: Haemolytic. Ref: R. M. Van Wagoner, et al, Tet. Lett., 2008, 49, 6457

1.12 Other Nonmacrolide Polyethers

53

OH OH

OH

OH OH

HO

OH

OH

OH

OH 3

OH

OH

OH

OH

OH

HO OH

O

OH OH

OH

64E

O

8

OH

OH

Cl

140 KmTx3 Karlotoxin 3 Type: Other nonmacrolide polyethers. C68H124O24 Source: Dinoflagellate Karlodinium veneficum CCMP 2936 (culture, Delaware Bays, USA). Pharm: Haemolytic. Ref: R. M. Van Wagoner, et al, Tet. Lett., 2008, 49, 6457 OH HO

OH

OH OH

OH OH

OH

OH

OH 3

OH

OH

OH

OH

HO OH

OH OH

O

OH OH

O

8

OH

OH

141 Ostreocin D 42-Hydroxy-3,26-didemethyl-19,44-dideoxypalytoxin Type: Other nonmacrolide polyethers. C127H219N3O53 [α]D23 = +16.6° (c = 0.1, H2O). Source: Dinoflagellate Ostreopsis siamensis. Pharm: Cytotoxic; hemolytic; LD50 (mus ip) = 0.75 mg/kg. Ref: M. Usami, et al, JACS, 1995, 117, 5389│T. Ukena, et al, Biosci. Biotechnol. Biochem., 2001, 65, 2585│T. Ukena, et al, Rapid Commun. Mass Spectrom., 2002, 16, 2387

54

1 Polyketides

O

HO

HO

O

OH

O

OH NH2

OH

O

H N

OH

OH

HO

O

OH

OH HO

OH OH OH

OH 73

OH HN HO

OH O OH

O

OH

HO OH

H O

OH

OH

OH OH

HO

O

OH

HO O

O

OH OH H

HO O

H

OH

OH

OH OH

OH OH OH

OH

OH

142 Symbiopolyol Type: Other nonmacrolide polyethers. C60H100O23S Source: Dinoflagellate Amphidinium sp. from jellyfish Mastigias papua (symbiont, Kochi, Japan). Pharm: Inhibits expression in HUVEC models. Ref: N. Hanif, et al, JNP, 2010, 73, 1318

HO

O OH S O O OH

OH

OH

OH

OH OH

OH

OH

OH HO OH

OH OH

O OH

O

3

OH

OH

143 10-O-Sulfo-KmTx1 Type: Other nonmacrolide polyethers. C69H126O27S Source: Dinoflagellate Karlodinium veneficum CCMP 2936 (culture, Delaware Bays, USA). Pharm: Haemolytic. Ref: R. M. Van Wagoner, et al, Tet. Lett., 2008, 49, 6457

1.13 Ladder Polyethers

55

10

O O S OH OH O

HO

OH OH

OH OH

OH

OH

OH 3

OH

OH

OH

OH

OH

HO OH

O

OH OH

OH O

9

OH

OH

144 10-O-Sulfo-KmTx3 Type: Other nonmacrolide polyethers. C68H124O27S Source: Dinoflagellate Karlodinium veneficum CCMP 2936 (culture, Delaware Bays, USA). Pharm: Haemolytic. Ref: R. M. Van Wagoner, et al, Tet. Lett., 2008, 49, 6457 O O S OH OH O

OH

10

HO

OH

OH OH

OH

OH

OH 3

OH

OH

OH

OH

OH

HO OH

O

OH OH

OH O

8

OH

OH

1.13 Ladder Polyethers 145 Adriatoxin Type: Ladder Polyethers. C42H66O24S3 Source: Mussel Mytilus galloprovincialis (digestive glands, Adriatic coast of Italy). Pharm: Toxin. Ref: P. Ciminiello, et al, Tet. Lett., 1998, 39, 8897 OH O S O O

OH

O O H

H H

O S O

O

OH H

H O

H H

O

O

H

H

H

H O H

H O

O

OH O H H

O

OH O S O O

56

1 Polyketides

146 Brevetoxin A Toxin GB1; PbTx1 Type: Ladder Polyethers. C49H70O13 Fine prisms (MeCN), mp 197–199 °C, mp 218–220 °C (double mp). Source: Dinoflagellate Gymnodinium breve [Syn. Ptychodiscus brevis] (Florida red tide). Pharm: Neurotoxin; ichthyotoxin. Ref: Y. Shimizu, et al, JACS, 1986, 108, 514│J. Pawlak, et al, JACS, 1987, 109, 1144│ K. S. Rein, et al, JOC, 1994, 59, 2101; 2107

H

H

O

24

4

O H

O

H

44

H O

25

H H O

O 1

49

HO H H

O H

O

O H

H O H

O H

O H H

H

147 Brevetoxin B PbTx2 Type: Ladder Polyethers. C50H70O14 Cryst., mp 295–297 °C. Source: Dinoflagellate Gymnodinium breve [Syn. Ptychodiscus brevis] (Florida red tide). Pharm: Ichthyotoxin; cardiotoxic; Na1+ channel activator. Ref: Y. Lin, et al, JACS, 1981, 103, 6773│Y. Shimizu, et al, JACS, 1986, 108, 514│K. S. Rein, et al, JOC, 1994, 59, 2101; 2107

HO

H O

1

O

H O

5

O

H

H H

H

O H

H

H

H O

O

42

H H

O H

H

O

O

O

O O

28 27

H

H

148 Brevetoxin B1 BTXB1 Type: Ladder Polyethers. C52H75NO17S Amorph. solid (Na salt). Source: Cockle Austrovenus stutchburyi. Pharm: Polyether marine toxin; MLD (mus ip) = 0.05 mg/kg. Ref: H. Ishida, et al, Tet. Lett., 1995, 36, 725│A. Morohashi, et al, Tet. Lett., 1995, 36, 8995 HO

H O O

H O

H

H

O

O H

H O

H

O

O

NH

H

O

O H

H

O

H

H H

O

O

H

O S

H HO

O

57

1.13 Ladder Polyethers

149 Brevetoxin B2 BTXB2 Type: Ladder Polyethers. C51H75NO17S Amorph. solid, [α]D25 = +19° (c = 0.6, MeCN aq). Source: Green mussel Perna canaliculus (New Zealand). Pharm: Cytotoxic (neuroblastoma cells through Na-channel, activating potency was one third that of PbTx-3); MLD (ddy mus ip) = 306 μg/kg. Ref: K. Murata, et al, Tetrahedron, 1998, 54, 735

H

HO O

H

O

O

O H

H

O H

H

O

O

O

H

H H

O

H O

O

S

O

H O

H

O

H

NH2

OH

HO

H

H

150 Brevetoxin B3a BTXB3A Type: Ladder Polyethers. C64H96O17 Source: Green mussel Perna canaliculus. Pharm: Polyether marine toxin. Ref: H. Ishida, et al, Tet. Lett., 1995, 36, 725│ A. Morohashi, et al, Tet. Lett., 1995, 36, 8995 12

H O O

O O

O H

H O

HO

O O

H

H

H H

O

H

H

COOH

O

H

O

O

H O

H O

H

H

151 Brevetoxin B3b BTXB3B Type: Ladder Polyethers. C66H100O17 Source: Green mussel Perna canaliculus. Pharm: Polyether marine toxin. Ref: H. Ishida, et al, Tet. Lett., 1995, 36, 725│ A. Morohashi, et al, Tet. Lett., 1995, 36, 8995

12

H O O

O O H

O H

H O

H

HO

O

H O

H O H

H O

H

COOH

O

H

O

O

H O H

H

58

1 Polyketides

152 Brevetoxin B4b Type: Ladder Polyethers. C69H109NO18S Source: Green mussel Perna canaliculus (New Zealand). Pharm: Toxin. Ref: A. Morohashi, et al, Nat. Toxins, 1999, 7, 45 H O

O

O

O

H

O

OH

O H

H H

HO

O

O

H

H

H O H

O

N H

H O

H

S O O

O

H

HO

O

H

H

H

153 Brevetoxin PbTx5 PbTx5 Type: Ladder Polyethers. C52H72O15 Amorph. Source: Dinoflagellate Gymnodinium breve [Syn. Ptychodiscus brevis] (Florida red tide). Pharm: Ichthyotoxin. Ref: H. -N. Chou, et al, Tet. Lett., 1982, 23, 5521; 1985, 26, 2865 H O

O

1

H

5

O H

O O H

O

H O

O

H H

H

O

O

H

H

H O

H

37

O

H O

H

O H 27

42

O

28

H

154 Brevetoxin PbTx6 PbTx6 Type: Ladder Polyethers. C50H70O15 Cryst. (MeOH), mp 295–297 °C, sinters at 255 °C. Source: Dinoflagellate Gymnodinium breve [Syn. Ptychodiscus brevis] (Florida red tide). Pharm: Ichthyotoxin; neurotoxin. Ref: H. -N. Chou, et al, Tet. Lett., 1982, 23, 5521; 1985, 26, 2865 H O O

H

1

O

5

O H

HO

H H

O

H O

H H H

O H

H

O

42

H

O

O H

H O 27

28

O

O H H

O

1.13 Ladder Polyethers

59

155 Brevetoxin PbTx7 PbTx7 Type: Ladder Polyethers. C49H72O13 Source: Dinoflagellate Gymnodinium breve [Syn. Ptychodiscus brevis] (Florida red tide). Pharm: Neurotoxin; ichthyotoxin. Ref: Y. Shimizu, et al, JACS, 1986, 108, 514│K. S. Rein, et al, JOC, 1994, 59, 2101; 2107

H O H

4

O 1

O

H

O

H H O

H H O H

24

H

H

25

O

HO H

49

O

44

O H

O

H H

O

OH

H

H

156 Brevetoxin PbTx8 PbTx8; Brevetoxin C Type: Ladder Polyethers. C49H69ClO14 Source: Dinoflagellate Ptychodiscus brevis [Syn. Gymnodinium breve]. Pharm: Toxin. Ref: J. Golik, et al, Tet. Lett., 1982, 23, 2535

H O

O

H O

O

H

HO

H O

H

H

O H

H

H H

O Cl

O

O

O

O

H H

O

O H

H

H

157 Brevisin Type: Ladder Polyethers. C39H62O11 Amorph. solid, [α]D25 = −21° (c = 0.33, MeOH). Source: Dinoflagellate Karenia brevis. (Wilson’s 58 clone). Pharm: Inhibits binding of Brevetoxin-3 to voltage-sensitive sodium channels (rat brain synaptosomes). Ref: M. Satake, et al, JOC, 2009, 74, 989│R. M. Van Wagoner, et al, JNP, 2010, 73, 1177 OH

O

H

OH O

OH H

OH

H O O

H

H

O H

O

O

H

60

1 Polyketides

158 Brevisulcenal F Type: Ladder Polyethers. C107H160O38 Source: Dinoflagellate Karenia brevisulcata (Wellington, New Zealand). Pharm: Cytotoxic (P388); mouse lethality. Ref: P. T. Holl and, et al, Harmful Algae, 2012, 13, 47│Y. Hamamoto, et al, JACS, 2012, 134, 4963 O

H

OH O

O O

OH

O

O

O

O

O

O

O

O

O

O

O

OH HO

O O

OH

OH

O

OH O

O

OH

O

O

O

OH

OH OH

OH

O

O OH

159 Caribbean ciguatoxin 1 C-CTX-1 Type: Ladder Polyethers. C62H92O19 Amorph. solid. Source: Horse-eye jack Caranx latus. Pharm: Na1+ channel activator (binding quasi-irreversibly to site 5 on the voltage sensitive sodium channel, VSSC); toxin (causes ciguatera food poisoning). Ref: R. J. Lewis, et al, JACS, 1998, 120, 5914

HO H H O

H O

HO 1

H

H

O H H O

O

H

H O

H

H

H O O H O H H

H

O H

H O H

OH O H

H

O

O

OH

56

H OH

160 Caribbean ciguatoxin 2 C-CTX-2 Type: Ladder Polyethers. C62H92O19 Source: Horse-eye jack Caranx latus. Pharm: Sodium channel activator (binding quasi-irreversibly to site 5 on the voltage sensitive sodium channel, VSSC); toxin (causes ciguatera food poisoning). Ref: R. J. Lewis, et al, JACS, 1998, 120, 5914

61

1.13 Ladder Polyethers

HO

H H O

H

H

H H O

O

O H

O

OH

O H

H

O H H

O

H O H

H

O O

H

H

H

H

H

H

O

1

O

H

H

HO

O

OH

56

OH

56 epi

161 1-Desulfoyessotoxin Type: Ladder Polyethers. C55H82O18S Source: Mussel Mytilus edulis (digestive glands, Norway). Pharm: Toxin. Ref: M. Satake, et al, Nat. Toxins, 1997, 5, 107; 164; 1998, 6, 235 1

OH

55

HO H

O H O

O O

H

H

S OH

H

O

H

O H

9

O

H

H

O

45

41 40 39

O

H

H

H H

O

H

O

H O

32

H OH

O

H

H

O

162 Dihydrobrevetoxin B PbTx3 Type: Ladder Polyethers. C50H72O14 Needles (MeCN), mp 291–293 °C. Source: Dinoflagellate Gymnodinium breve [Syn. Ptychodiscus brevis] (Florida red tide). Pharm: Ichthyotoxin; neurotoxin. Ref: H. -N. Chou, et al, Tet. Lett., 1982, 23, 5521; 1985, 26, 2865│R. C. Crouch, et al, Tetrahedron, 1995, 51, 8409 1

OH

55

HO O

O O

O H H

S OH

H

H O

9

O H H

H H O

H

H O

H H O

H O H O

H O

32

O H

H OH

O

41 40 39

H

45

62

1 Polyketides

163 2,3-Dihydro-2,3-dihydroxyciguatoxin 3C Ciguatoxin 2A1 Type: Ladder Polyethers. C57H84O18 Source: Dinoflagellate Gambierdiscus toxicus. Pharm: Toxin. Ref: M. Satake, et al, Tet. Lett., 1998, 39, 1197 H

HO

HO HO

H

3

H O 6

2

O

H

H OH

H

O

H H O

H O

H O H

O

O H H

H

OH

O H

O H H

H O

H O H

49

O 52

50

H

164 Gambieric acid A GA-A Type: Ladder Polyethers. C59H92O16 White amorph. solid, [α]D20 = +33° (c = 0.49, MeOH). Source: Dinoflagellate Gambierdiscus toxicus (culture). Pharm: Antifungal (potent). Ref: H. Nagai, et al, JACS, 1992, 114, 1102│H. Nagai, et al, JOC, 1992, 57, 5448│A. Morohashi, et al, Tetrahedron, 2000, 56, 8995

H HO

H

12

HO H O

O H

H

O

H O

H

O

O

O

OH H O H

H H O H

H

O H

H

H 49

COOH

OH

165 Gambieric acid B GA-B Type: Ladder Polyethers. C60H94O16 White amorph. solid. Source: Dinoflagellate Gambierdiscus toxicus (culture). Pharm: Antifungal (potent). Ref: H. Nagai, et al, JACS, 1992, 114, 1102│H. Nagai, et al, JOC, 1992, 57, 5448│A. Morohashi, et al, Tetrahedron, 2000, 56, 8995 H HO

H

12

HO

O H

H

H

O

H O

H

O

O

OH H

O

O H

H H

H O H O

O

H

H

H COOH

OH

1.13 Ladder Polyethers

63

166 Gambieric acid C GA-C Type: Ladder Polyethers. C65H100O19 White amorph. solid. Source: Dinoflagellate Gambierdiscus toxicus (culture). Pharm: Antifungal (potent). Ref: H. Nagai, et al, JACS, 1992, 114, 1102│H. Nagai, et al, JOC, 1992, 57, 5448│A. Morohashi, et al, Tetrahedron, 2000, 56, 8995

H HO

O O

O H

HO

O

H

12

H

H O

H

O

H

H

OH H O H

H O H O

H

H 49

O

O

H

H

O COOH

COOH

167 Gambieric acid D GA-D Type: Ladder Polyethers. C66H102O19 White amorph. solid. Source: Dinoflagellate Gambierdiscus toxicus (culture). Pharm: Antifungal (potent). Ref: H. Nagai, et al, JACS, 1992, 114, 1102│H. Nagai, et al, JOC, 1992, 57, 5448│A. Morohashi, et al, Tetrahedron, 2000, 56, 8995

H HO HO

O

H

12

O O H H

H

H

H O

H

O

O

H

OH H O H

H O H O H O

O H

H O

COOH

COOH

168 Gambierol Type: Ladder Polyethers. C43H64O11 Amorph. solid, Sol. MeOH, Py, CH2Cl2; poorly sol. H2O. Source: Dinoflagellate Gambierdiscus toxicus (Polynesia (Fr.), Oceania). Pharm: Toxin. Ref: M. Satake, et al, JACS, 1993, 115, 361│A. Morohashi, et al, Tet. Lett., 1999, 40, 97

64

1 Polyketides

OH

H

H O

O

H H

O O

O H

H

H

H

H

O

O

H

O OH

H

OH

169 Gymnocin A Type: Ladder Polyethers. C55H80O18 Amorph. solid, [α]D20 = +12.5° (c = 0.11, CHCl3). Source: Dinoflagellate Karenia mikimotoi [Syn. Gymnodinium mikimotoi] (red tide). Pharm: Cytotoxic (P388, IC50 = 1.3 μmol/L). Ref: M. Satake, et al, Tet. Lett., 2002, 43, 5829│C. Tsukano, et al, Tet. Lett., 2006, 47, 6803 OH H

O

H

H

H

H

O

O O

OH H

H O

H

O

O H H

O H

H

H

H

O

H

H O O

H

H

H

H

O

O H OH

O H

H

H O

170 Gymnocin A2 Type: Ladder Polyethers. C55H80O18 Source: Dinofiagellate Gymnodinium mikimotoi (Syn. Karenia mikimotoi) (Kushimoto Bay, Wakayama, Japan). Pharm: cytotoxic (P388, moderate). Ref: Y. Tanaka, et al, Heterocycles, 2013, 87, 2037 OH

OH O O

HO O O

O

O O

H

O

O

O

O

O

O

OH O

171 Gymnocin B Type: Ladder Polyethers. C62H92O20 Amorph. solid. Source: Dinoflagellate Karenia mikimotoi [Syn. Gymnodinium mikimotoi] (red tide). Pharm: Cytotoxic (P388, IC50 = 1.47 μg/mL). Ref: M. Satake, et al, Tet. Lett., 2005, 46, 3537

65

1.13 Ladder Polyethers

OH H OH H O

H

H

H O

O OH

H

O

O

H

H

H O

H

H

H

O

H

O

O

OH

H

H H O

O H

H

H O

O H H

OH

O H

OH

172 Halichondrin B Type: Ladder Polyethers. C60H86O19 Cryst., mp 164–166 °C, [α]D = −58.9° (c = 0.94, MeOH). Source: Sponges Lissodendoryx sp. (yield = 5.1 × 10−5%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992), Phakellia carteri (yield = 3.5 × 10−6%, Comoros), Axinella spp., Halichondria okadai and Lissodendoryx sp. Pharm: Cytotoxic (MMOA: microtubule depolymerizer); cytotoxic (P388, IC50 = 0.78 ng/mL) (Litaudon, 1994); cytotoxic (NCl’s hmn tumour cell lines panel, mean panel GI50 = 1.38 × 10–10 mol/L, COMPARE Correlation Cocff. = 1.00 (Halichondrin B as “seed”) (Litaudon, 1994); undergoing preclinical trials at U.S. Natl. Cancer Inst. (1994)); inhibited binding of radiolabeled vinblastine and GTP to tubulin; antimitotic (caused accumulation of cells arrested in mitosis). Ref: Y. Hirata, et al, Pure Appl. Chem., 1986, 58, 701│T. D. Aicher, et al, JACS, 1992, 114, 3162│G. R. Pettit, et al, JOC, 1993, 58, 2538│ M. Litaudon, et al, Tet. Lett., 1994, 35, 9435│G. R. Pettit, et al, J. Med. Chem., 1994, 37, 1165│ M. Litaudon, et al, JOC, 1997, 62, 1868│ K. L. Jackson, et al, Chem. Rev., 2009, 109, 3044│S. J. H. Hickford,et al, BoMC, 2009, 17, 2199 H H

O

H O

O O H O

H H HO

H

O

H

O

O

H O

O H H O

H H

H

O

O O

O

H

O

OH OH

173 Halichondrin B-1020 Type: Ladder Polyethers. C56H76O17 White solid. Source: Sponge Lissodendoryx sp. (large collection, Kaikoura, New Zealand). Pharm: Cytotoxic (P388, IC50 = 1.1 ng/mL). Ref: S. J. H. Hickford,et al, BoMC, 2009, 17, 2199

66

1 Polyketides

O

O

O O 44

O

O

O

O O

O

O

O O O O

O O

174 Halichondrin B-1076 Type: Ladder Polyethers. C59H80O18 White solid. Source: Sponge Lissodendoryx sp. (large collection, Kaikoura, New Zealand). Pharm: Cytotoxic (P388, IC50 = 1.1 ng/mL). Ref: S. J. H. Hickford,et al, BoMC, 2009, 17, 2199 O

O

O O 44

O

O

O

O O

O

O

O O O O

O O O

175 Halichondrin B-1092 Type: Ladder Polyethers. C61H86O17 White solid. Source: Sponge Lissodendoryx sp. (large collection, Kaikoura, New Zealand). Pharm: Cytotoxic (P388, IC50 = 0.76 ng/mL). Ref: S. J. H. Hickford,et al, BoMC, 2009, 17, 2199 O

O

O O 44

O

O

O

O

O O

O

O

O O

O HO

O

1.13 Ladder Polyethers

67

176 Halichondrin B-1140 Type: Ladder Polyethers. C61H85ClO18 White solid. Source: Sponge Lissodendoryx sp. (large collection, Kaikoura, New Zealand). Pharm: Cytotoxic (P388, IC50 = 2.0 ng/mL). Ref: S. J. H. Hickford,et al, BoMC, 2009, 17, 2199

O

O

O O 44

O

O

O

O O

O

O

O

O O

O

O O

Cl

HO

177 Halichondrin C Type: Ladder Polyethers. C60H86O20 Cryst., mp 169–172 °C, [α]D = −41.6° (c = 0.49, MeOH). Source: Sponge Halichondria okadai. Pharm: Cytotoxic (MMOA: microtubule depolymerizer); cytotoxic. Ref: Y. Hirata, et al, Pure Appl Chem, 1986, 58, 701│K. L. Jackson, et al, Chem. Rev., 2009, 109, 3044 OH H

H O

H

O

O

OH OH

H

H

O H

H

O O

O

H H

O O O

O

H

O H H O O

H H

O 10

H

O 12

OH

178 Halistatin 1 10-Hydroxyhalichondrin B; Isohalichondrin C Type: Ladder Polyethers. C60H86O20 Amorph. solid, [α]D25 = −58.4° (c = 0.57, MeOH). Source: Sponges Phakellia carteri

68

1 Polyketides

(yield = 8.8 × 10−7%, Comoros) and Axinella carteri. Pharm: Cytotoxic (P388, ED50 = 4 × 10−4 μg/mL; NCI’s 60-cell lines antitumor screening panel, average overall panel GI50 = 7 × 10−10 mol/L); antimitotic (caused accumulation of cells arrested in mitosis); inhibited tubulin polymerization; inhibited binding of radiolabeled vinblastine and GTP to tubulin. Ref: G. R. Pettit, et al, JOC, 1993, 58, 2538 H H HO

H

O

H O

O O

O OH

H O O

H

H

H

O

O

H H O

H

H

H

O

O

H

O OH 10

O O

OH

12

O

179 Halistatin 2 Type: Ladder Polyethers. C61H86O20 Source: Sponge Axinella carteri. Pharm: Tubulin polymerisation inhibitor. Ref: G. R. Pettit, et al, Gazz. Chim. Ital., 1993, 123, 371 H H

H HO

H

O O

OH

H

O

H O

O O

H

H O O

H

H

H

O

O H O

O H H O

H H

O

OH 10

O O

O

12 13

180 Halistatin 3 Neohomohalichondrin B Type: Ladder Polyethers. C61H88O19 mp 185–187 °C, [α]D25 = −62° (c = 0.04, MeOH). Source: Sponges Phakellia sp. and Lissodendoryx sp. (yield = 8 × 10−6%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992). Pharm: Cytotoxic (P388, IC50 = 0.8 ng/mL); cytotoxic (P388, ED50 = 3.5 × 10−5 μg/mL); cytotoxic (SF295, GI50 = 3.5 × 10−5 μg/mL; OVCAR-3, GI50 = 1.3 × 10−5 μg/mL; A498, GI50 = 5.6 × 10−5 μg/mL; SK-MEL-5, GI50 = 2.5 × 10−5 μg/mL). Ref: G. R. Pettit, et al, J. Chem. Soc., Chem. Commun., 1995, 383│ M. Litaudon, et al, JOC, 1997, 62, 1868

1.13 Ladder Polyethers

H

H H H

O

O

H

O

O

HO

O O

O H

O

H

H

69

H

O

O

H

H H O

O

H H

O

H 10

O O

12

HO O

OH

181 Hemibrevetoxin B GB-N Type: Ladder Polyethers. C28H42O7 Non-cryst. solid, [α]D22 = +115° (c = 0.1, CHCl3). Source: Dinoflagellate Gymnodinium breve. Pharm: Cytotoxic (cultured mouse neuroblastoma cells, 5 μmol/L, causes characteristic rounding); toxin. Ref: V. K. Prasad, et al, JACS, 1989, 111, 6476│I. Kadota, et al, Tet. Lett., 1995, 36, 5777│ M. Morimoto, et al, Tet. Lett., 1996, 37, 6365

H

O

H

OH

O O HO

H

H

H

O

O H

182 Homohalichondrin A Type: Ladder Polyethers. C61H86O21 [α]D = −97.1° (c = 1.23, MeOH). Source: Sponges Halichondria okadai and Axinella sp. Pharm: Cytotoxic (MMOA: microtubule depolymerizer); cytotoxic. Ref: Y. Hirata, et al, Pure Appl. Chem., 1986, 58, 701 H

H OH H

H

H O

O

H

O

H

H

O

O O

HO

O

O H

H

H

O

O H O

O H H O

H H

O

O H O

10

O

13

12

OH

OH

183 Homohalichondrin B Type: Ladder Polyethers. C61H86O19 Source: Sponges Lissodendoryx sp. (yield = 5.3 × 10−5%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992), Phakellia carteri (yield = 3.4 × 10−6%, Comoros), Halichondria okadai and Axinella

70

1 Polyketides

carteri. Pharm: Cytotoxic (MMOA: microtubule depolymerizer); cytotoxic (P388, IC50 = 0.22 ng/mL); cytotoxic (NCl’s hmn tumour cell lines panel, mean panel GI50 = 1.58 × 10–10 mol/L, COMPARE Correlation Cocff. = 0.91 (Halichondrin B as “seed”)); antimitotic (caused accumulation of cells arrested in mitosis); inhibited binding of radiolabeled vinblastine and GTP to tubulin. Ref: Y. Hirata, et al, Pure Appl. Chem., 1986, 58, 701│T. D. Aicher, et al, JACS, 1992, 114, 3162│G. R. Pettit, et al, JOC, 1993, 58, 2538│ M. Litaudon, et al, Tet. Lett., 1994, 35, 9435│G. R. Pettit, et al, J. Med. Chem., 1994, 37, 1165│ M. Litaudon, et al, JOC, 1997, 62, 1868│ S. J. H. Hickford,et al, BoMC, 2009, 17, 2199 H

H O

H

OH H H O

H

O

H

O

O O

HO

O

O H

H

H

O

O

O H H O

H O

H

H O

H

10

O OH 12

O

13

184 Homohalichondrin C Type: Ladder Polyethers. C61H86O20 Source: Sponge Halichondria okadai. Pharm: Cytotoxic (MMOA: microtubule depolymerizer). Ref: Y. Hirata, et al, Pure Appl. Chem., 1986, 58, 701│T. D. Aicher, et al, JACS, 1992, 114, 3162 H

H H

OH H H O HO

H

O

H

H

O

O O

O

O

O H

H

H

O

O H O

O H H O

H H

H 10

O O

O

O

12

OH 13

185 51-Hydroxyciguatoxin 3C 51-HydroxyCTX 3C Type: Ladder Polyethers. C57H82O17 Source: Dinoflagellate Gambierdiscus toxicus. Pharm: LD (mus) = 0.27 μg/kg. Ref: M. Satake, et al, Tet. Lett., 1998, 39, 1197

1.13 Ladder Polyethers

H

OH

H

O H H

H

H O

H O

1

O

O H

H O

OH O H

O H

H H

O H

O O

49

52

H

H

O

H

H

O

6

50

H

H H OH

71

51

OH

186 45-Hydroxyyessotoxin Type: Ladder Polyethers. C55H82O22S2 Amorph. solid. Source: Scallop Patinopecten yessoensis, mussel Mytilus galloprovincialis. Pharm: LD50 (mus, ipr) = 0.5 mg/kg. Ref: M. Satake, et al, Tet. Lett., 1996, 37, 5955│A. Morohashi, et al, Biosci., Biotechnol., Biochem., 2000, 64, 1761

O

55

O HO

S OH 1

H

O H H

O

O

S OH

9

H

H

H

O

H

O

O

H H

41

45

HO

40 39

H

H

O

O

O

H

H

O

H O O

O H

O

H

32

H OH

H O

187 Isohomohalichondrin B Type: Ladder Polyethers. C61H86O19 Source: Sponge Lissodendoryx sp. (yield = 6.7 × 10−5%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992). Pharm: Cytotoxic (in vitro, P388, IC50 = 0.18 ng/mL); cytotoxic (NCl’s hmn tumour cell lines panel, mean panel GI50 = 1.15 × 10–10 mol/L, COMPARE Correlation Cocff. = 0.80 (Halichondrin B as “seed”)); tubulin polymerisation inhibitor; antimitotic. Ref: S. J. H. Hickford,et al, BoMC, 2009, 17, 2199│ M. Litaudon, et al, Tet. Lett., 1994, 35, 9435│ M. Litaudon, et al, JOC, 1997, 62, 1868

72

1 Polyketides

O

O

O O 44

O

O

O O

O

O

O

O O O O

O HO O OH

188 38-epi-Isohomohalichondrin B Type: Ladder Polyethers. C61H86O19 Source: Sponge Lissodendoryx sp. (depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992). Pharm: Cytotoxic (P388, IC50 = 3.4 ng/mL). Ref: M. Litaudon, et al, JOC, 1997, 62, 1868 HO H O O

O H 55

OH

H 44

O H

O 38

H

O

H

O H

O H

O

H

H O

O

O H

H

O O

O O

H O

189 Lituarine A 4,5-Dideoxy-lituarine C Type: Ladder Polyethers. C38H55NO9 Cryst., mp 83–85 °C. Source: Sea pen Lituaria australasiae (New Caledonia). Pharm: Cytotoxic (KB, IC50 = 3.7–5.0 ng/mL). Ref: J. -P. Vidal, et al, JOC, 1992, 57, 5857

1.13 Ladder Polyethers

O

H H

73

O H

H

O

O

5

H

O

4

O O O H N O

190 Lituarine B 5-Acetyl-lituarine C Type: Ladder Polyethers. C40H57NO12 Cryst., mp 126–129 °C. Source: Sea pen Lituaria australasiae (New Caledonia). Pharm: Cytotoxic (KB, IC50 = 1–2 ng/mL). Ref: J. -P. Vidal, et al, JOC, 1992, 57, 5857

O

H

H

O H

H

O

O

H

O

O O

5 4

O

OH

O O H N O

191 Lituarine C Type: Ladder Polyethers. C38H55NO11 Cryst., mp 153–157 °C. Source: Sea pen Lituaria australasiae (New Caledonia). Pharm: Cytotoxic (KB, IC50 = 5–6 ng/mL); antineoplastic; antifungal. Ref: J. -P. Vidal, et al, JOC, 1992, 57, 5857 O

H

H

O H

H

O

O

H

OH

O

OH

O O O H N

O

74

1 Polyketides

192 Maitotoxin (MTX) Type: Ladder Polyethers. C164H258O68S2 Amorph. solid (di-Na salt). Source: Dinoflagellate Gambierdiscus toxicus GII-1. Pharm: Toxic (lagest (3422Da) and most lethal toxin); LD50 (mus ip) = 0.17 μg/kg; one of most potent non-proteinaceous toxins; phycotoxin; neurotoxin; Ca2+ channel and protein kinase activator. Ref: T. Yasumoto, et al, Chem. Rer., 1993, 93, 1897│ M. Murata, et al, JACS, 1993, 115, 2060; 1994, 116, 7098│W. Zheng, et al, JACS, 1996, 118, 7946│ M. Sasaki, et al, Angew. Chem., Int. Ed. Engl., 1996, 35, 1672│T. Nonomura, et al, Angew. Chem., Int. Ed. Engl., 1996, 35, 1675

OH H HO

O H H O H

O

H H

O

O H

O

OH

O H

O H

O H

H

H

O O H

H O H O

H O

HO H

H

O

O

HO HO

OH OH O

S O

H

O

O O

OH

OH

O

H

H

O

H

OH OH

O

HO

O

H

OH H

O

O

H

H O

H

OH

O H OH

H

H

O

H

OH

H

O

H

OH

H

O

H

H

OH

O

OH

O H

H

HO

H H

HO

S

H

O

O

H

OH

OH

H

OH

H O OH

H HO OH

H

O H

OH

OH

193 53-Methoxy-neoisohomohalichondrin B Type: Ladder Polyethers. C62H88O19 Oil. Source: Sponge Lissodendoryx sp. (yield = 1.8 × 10−5%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992). Pharm: Cytotoxic (P388, IC50 = 0.1 ng/mL). Ref: M. Litaudon, et al, JOC, 1997, 62, 1868

1.13 Ladder Polyethers

H

HO H O O

O

H

H

O

O O

O

H O O

H

H

H

O

O

H

75

H

O

O

H

H

O

O O O O

194 55-O-Methylisohomohalichondrin B Type: Ladder Polyethers. C62H88O19 Oil. Source: Sponge Lissodendoryx sp. (yield = 8 × 10−7%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992). Pharm: Cytotoxic (P388, IC50 = 10 ng/mL). Ref: M. Litaudon, et al, JOC, 1997, 62, 1868

O

O

O O 44

O

O

O

O O

O

O

O

O O

O

O HO O 55

O

195 Neonorhalichondrin B Type: Ladder Polyethers. C59H84O20 Oil. Source: Sponge Lissodendoryx sp. (yield = 1 × 10−6%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992). Pharm: Cytotoxic (P388, IC50 = 0.4 ng/mL). Ref: M. Litaudon, et al, JOC, 1997, 62, 1868 H

H O

O

H

H

O

O O

HO O HO

OH

O H

H

H

O

O

H

O

H

H

O

O

O O O

O

76

1 Polyketides

196 Norhalichondrin A Type: Ladder Polyethers. C59H82O21 [α]D = −47.8° (c = 1.13, MeOH). Source: Sponge Halichondria okadai. Pharm: Cytotoxic (MMOA: microtubule depolymerizer). Ref: D. Uemura, et al, JACS, 1985, 107, 4796 H

H H

HO

O

O

H

H

O

O O

O O

O

H

H

H

O

H

H

O

O H

H

O

O

O O

O

OH

OH

12

13

O

H

OH

197 Norhalichondrin B Type: Ladder Polyethers. C59H82O19 Source: Sponges Lissodendoryx sp. (yield = 7 × 10−7%, depth of 100m, off the Kaikoura coast, New Zealand, Feb 1992) and Halichondria okadai. Pharm: Cytotoxic (MMOA: microtubule depolymerizer). Ref: Y. Hirata, et al, Pure Appl. Chem., 1986, 58, 701│T. D. Aicher, et al, JACS, 1992, 114, 3162│ M. Litaudon, et al, JOC, 1997, 62, 1868 H

H H

HO

O

O

H

H

O

O O

O

O

O H

H

H

O

H

H

O

O H

H

O

O

O O

OH

O

H

12

13

O

198 Norhalichondrin C Type: Ladder Polyethers. C59H82O20 Source: Sponge Halichondria okadai. Pharm: Cytotoxic (MMOA: microtubule depolymerizer). Ref: Y. Hirata, et al, Pure Appl. Chem., 1986, 58, 701 H H

HO

O O O

H

H O

O

H

H

O

O O H

H

H

O

O H O

OH

H O

O H OO

H

O 12

O

13

OH

77

1.13 Ladder Polyethers

199 Pacific ciguatoxin 1 P-CTX 1 Type: Ladder Polyethers. C60H86O19 Source: Dinoflagellate Gambierdiscus toxicus, moray eel Gymnothorax javanicus and other fish and shellfish esp. coral reef spp., carnivorous fishes (Polynesia (Fr.), Oceania). Pharm: Toxic (causes hmn intoxication when eating tropical reef fishes such as moray eels); toxic (causes ciguatera food poisoning, Gambierdiscus toxicus is the primary cause). Ref: P. J. Scheuer, Bioact. Mol., 1989, 10, 265│ M. Murata, et al, JACS, 1990, 112, 4380│ M. Murata, et al, Tet. Lett., 1992, 33, 525│H. Oguri, et al, Tenrahedron, 1997, 53, 3057│ M. Satake, et al, JACS, 1997, 119, 11325│T. Yasumoto, et al, JACS, 2000, 122, 4988

H O O

HO

H

H

OH

O H

O

H H O

H H O

H

H

H

HO

H

O

H

OH H O

H O H

O H H

O H H

H O H OH

O

OH

200 Pacific ciguatoxin 2 P-CTX 2 Type: Ladder Polyethers. C60H86O18 Source: Moray eel Lycodontis javanicus. Pharm: Cardiotoxin. Ref: R. J. Lewis, et al, Toxicon, 1993, 31, 637 H

HO H O O HO

H

H

H H O

H

O H H

O O

O H H H HO

H

H

O

O H H

OH H

O H H O H

O

O 52 54

H

OH

201 Pacific ciguatoxin 3C P-CTX 3C Type: Ladder Polyethers. C57H82O16 Source: Dinoflagellate Gambierdiscus toxicus (culture). Pharm: Highly toxin, LD50 (mus, ipr) 0.0013 mg/kg. Ref: M. Murata, et al, JACS, 1990, 112, 4380 H

OH

H

O H

3 2

H

H

H HO

O 6

OH

O H OH

H

O O H H

O H H

O H

H H

O

OH H

H H O H

O 49

O 50

52

78

1 Polyketides

202 Pacific ciguatoxin 4B Type: Ladder Polyethers. C60H84O16 Source: Dinoflagellate Gambierdiscus toxicus. Pharm: Neurotoxin; cardiotoxin; ichthyotoxin. Ref: M. Satake, et al, Biosci., Biotechnol., Biochem., 1997, 60, 2103

H

H HO

H

O

H

H H O

H H O

O H

O

H

HO H

O H H

O H H

O H O H H H OH

O H

OH H O

O

H

203 Protoceratin I 1a-Homoyessotoxin Type: Ladder Polyethers. C56H84O21S2 Amorph. solid (di-Na salt), [α]D20 = −5.5° (c = 1, MeOH) (di-Na salt). Source: Dinoflagellate Protoceratium reticulatum, unidentified mussels. Pharm: Cytotoxic (hmn cancer cell lines, IC50 < 0.0005 μmol/L, demonstrated some cell-line selectivity). Ref: M. Konishi, et al, JNP, 2004, 67, 1309 O O S O OH

HO

O H O O

O

H H

S OH

H O

O H H O

H H

H H O H

O H

H H O O

H O

O

H

O H OH H

204 Protoceratin II Type: Ladder Polyethers. C66H100O29S2 [α]D20 = +12.1° (c = 0.2, MeOH). Source: Dinoflagellate Protoceratium reticulatum. Pharm: Cytotoxic (hmn cancer cell lines, IC50 < 0.0005 μmol/L, demonstrated some cell-line selectivity). Ref: M. Konishi, et al, JNP, 2004, 67, 1309

1.13 Ladder Polyethers

O O S O OH

HO

O H O O

H O H

S OH

H O

H

O

79

H O H

H H O

H O H

H

H O H

O H 32

H O

O H O H O

O

OH O

O

HO HO

OH

OH

205 Protoceratin III Type: Ladder Polyethers. C61H92O25S2 Source: Dinoflagellate Protoceratium reticulatum. Pharm: Cytotoxic (hmn cancer cell lines, IC50 < 0.0005 μmol/L, demonstrated some cell-line selectivity). Ref: M. Konishi, et al, JNP, 2004, 67, 1309 O O

S

O OH

O

O

H

O

O

H

H

S OH

HO H

O H

H

O

H

H H

O

H O

H O H

H

O

O

H O O

H O

H

32

H

HO

H O OH O OH

206 Protoceratin IV Type: Ladder Polyethers. C71H108O33S2 Source: Dinoflagellate Protoceratium reticulatum. Pharm: Cytotoxic (hmn cancer cell lines, IC50 < 0.0005 μmol/L, demonstrated some cell-line selectivity). Ref: M. Konishi, et al, JNP, 2004, 67, 1309

80

1 Polyketides

O O

S

O OH

O

H

H

O

O

H

S

O

HO H

O

OH

H

H

O H

O

H

H O H

O

H

H

H

O

32

H O

O

H

H O

O

HO

H

O

H O

OH

O

HO

O

O

OH

O

HO

OH

HO

207 Prymnesin 1 Type: Ladder Polyethers. C107H154Cl3NO44 Source: Red tide alga Prymnesium parvum (class Haptophyceae). Pharm: Hemolytic; ichthyotoxin. Ref: T. lgarashi, et al, JACS, 1996, 118, 479; 1999, 121, 8499│ M. Sasaki, et al, Tet. Lett., 2001, 42, 5725 OH

HO

OH O O 77

HO

OH 82

OH

Cl

OH OH

OH O OH O HO OH Cl HO H HO O O H O H O H O O H HO H OH OH OH

OH

78

HO HO

HO H H O O H H HO

H H O O H H

H O H O H H HO Cl

H O

H

H

H

O

H

O

H

H

O

NH2

208 Prymnesin 2 Type: Ladder Polyethers. C96H136Cl3NO44 Pale yellow solid, [α]D23 = +21.2° (c = 0.1, dioxane/AcOH). Source: Red tide alga Prymnesium parvum (class Haptophyceae). Pharm: Hemolytic; ichthyotoxic. Ref: T. lgarashi, et al, JACS, 1996, 118, 479│ L. Glendenning, et al, Bull. Chem. Soc. Jpn., 1996, 69, 2253│T. lgarashi, et al, JACS, 1999, 121, 8499│ M. Sasaki, et al, Tet. Lett., 2001, 42, 5725

1.13 Ladder Polyethers

OH

OH

HO

Cl O

OH

OH

O HO

Cl H H O

OH

H O H O

HO H H O

OH

OH

OH

HO

O H H HO

O H HO

H H O O H H

H

H

O

O HO H H HO Cl

H

H

H

O

H O O

H

H

NH2

H OH OH OH

HO

81

209 Tamulamide A Type: Ladder Polyethers. C35H45NO9 Source: Dinoflagellate Karenia brevis (Wilson’s 58 clone). Pharm: Competes with Brevetoxin-3 binding site (rat brain synaptosomes, without accompanying toxicity associated with brevetoxins). Ref: L. T. Truxal, et al, JNP, 2010, 73, 536 O

O

O HN

O

O O O

O

O

210 Tamulamide B Type: Ladder Polyethers. C34H43NO9 Source: Dinoflagellate Karenia brevis (Wilson’s 58 clone). Pharm: Competes with Brevetoxin-3 binding site (rat brain synaptosomes, without accompanying toxicity associated with brevetoxins). Ref: L. T. Truxal, et al, JNP, 2010, 73, 536 O

O HN

H

O O

O

O O

O

O

82

1 Polyketides

211 45,46,47-Trinoryessotoxin Type: Ladder Polyethers. C52H78O21S2 Amorph. solid. Source: Scallop Patinopecten yessoensis. Pharm: Toxic; LD50 (mus, ipr) = 0.22 mg/kg. Ref: M. Satake, et al, Tet. Lett., 1996, 37, 5955

O

O S

OH

O

1

HO H

O

H

S H

41 40 39

H O

9

OH

O

H

O

O O

H

H

O

H H

H

O H

O

H

O

H

32

H H O

O

H

O H

OH

H

O

212 Yessotoxin YTX Type: Ladder Polyethers. C55H82O21S2 Amorph. solid (di-Na salt), [α]D20 = +3.01° (c = 0.45, MeOH). Source: Dinoflagellates Protoceratium reticulatum and Gonyaulax spinifer, scallop Patinopecten yessoensis, mussel (blue mussel) Mytilus galloprovincialis. Pharm: Toxic constituent of scallops; LD50 (mus, ipr) = 0.1 mg/kg. Ref: M. Murata, et al, Tet. Lett., 1987, 28, 5869│ M. Kumagai, et al, CA, 1988, 108, 70214v│ H. Takahashi, et al, Tet. Lett., 1996, 37, 7087

OH

O S

1

O

O

55

HO O

H

H

O

O

O H

9

O

40

O

H

H H

H H O

H H

41

H O

H

S HO

45

H

O

O

H O O

H O

39

O

H

H

OH

H

1.14 Polyether Antibiotics

83

1.14 Polyether Antibiotics 213 Acanthifolicin Acanthifolic acid Type: Polyether antibiotics. C44H68O13S Cryst. (CHCl3/C6H6), mp 167–169 °C, [α]D = +25.3° (c = 0.08, CHCl3). Source: Sponge Pandaros acanthifolium and other sponges. Pharm: Cytotoxic (P388, ED50 = 2.8 × 10−4 μg/mL; KB, ED50 = 2.1 × 10−3 μg/mL; L1210, ED50 = 3.9 × 10−3 μg/mL); antineoplastic; useful as growth stimulant or in treatment of coccidiosis; ichthyotoxin; phycotoxin; protein phosphatase inhibitor; smooth muscle contractor; ionophoric agent; LD50 (mus, ivn) = 0.14 mg/kg. Ref: F. J. Schmitz, et al, JACS, 1981, 103, 2467│US Pat., 1981, 4 302 470; CA, 96, 74612 │CRC press, DNP on DVD, 2012, version 20.2 OH HO 2

O

S 9

O 7

10

H

O

14

O

H

O

OH

H

OH 31

19

27

H

O

H

OH

H

O

O 34

214 13-Demethylspirolide C SPX Type: Polyether antibiotics. C42H61NO7 Source: Unidentified scallops (contaminated), an unidentified phytoplankton, dinflagellate Alexandrium ostenfeldii from unidentified phytoplankton assemblages (Nova Scotia). Pharm: Microalgal toxin; anti-AD preclinical trial (Target: Decrease GSK-3β and ERK. Animal Model: 3xTg mice cortical neurons. Effects: Glutamate-induced neurotoxicity inhibition both in control and 3xTg neurons) (Russo, 2016). Ref: T. Hu, et al, J. Chem. Soc., Chem. Commun., 1995, 2159│T. Hu, et al, JNP, 2001, 64, 308│S. L. MacKinnon, et al, JOC, 2006, 71, 8724│ M.D. Lebar, et al, NPR, 2007, 24, 774 (rev)│P. Russo, et al, Mar. Drugs, 2016, 14, 5 (review)

N O

2 3

O

27

O

19

H

O

O

OH

13

HO

215 7-Deoxyokadaic acid Type: Polyether antibiotics. C44H68O12 Cryst. Source: Dinoflagellate Prorocentrum lima. Pharm: Antifungal (10 μg/disc, Aspergillus niger, Penicillium funiculosum and Candida rugosa); cytotoxic; serine/threonine-specific protein phosphatase inhibitor.

84

1 Polyketides

Ref: H. Nagai, et al, J. Appl. Phycol., 1990, 2, 305│A. B. Dounay, et al, Angew. Chem., Int. Ed., 1999, 38, 2258 O 10

OH

2

HO

O

H

9 7

O

14

O

OH 31

19

O

H

H

27

H

O

H

H

O

O 34

OH

216 13,19-Didemethylspirolide C Type: Polyether antibiotics. C41H59NO7 Source: Dinoflagellate Alexandrium ostenfeldii in contaminated shellfish. Pharm: Microalgal toxin. Ref: S. L. MacKinnon, et al, JNP, 2006, 69, 983│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

N O

27

O

O

19

H

2 3

H

O

O

OH 13

HO

217 14,15-Dihydrodinophysistoxin 1 Type: Polyether antibiotics. C45H72O13 Amorph. solid, [α]D25 = +19° ( c = 0.36, CHCl3). Source: Sponge Phakellia sp. (Coast of Maine). Pharm: Cytotoxic (L1210); antiviral (HSV-1 and VSV). Ref: R. Sakai, et al, JNP, 1995, 58, 773

O

15 14

H

H O

OH

O O HO

2

OH

H

OH

O

O H

O H

OH

H

O

35

1.14 Polyether Antibiotics

85

218 Dinophysistoxin 1 DTX1 Type: Polyether antibiotics. C45H70O13 Solid, mp 134 °C, [α]D20 = +28°. Source: Dinoflagellate Dinophysis fortii, scallop Patinopecten yessoensis, mussels. Pharm: Toxic (diarrhetic shellfish poisoning). Ref: T. Yasumoto, et al, Terrahedron, 1985, 41. 1019│T. Suzuki, et al, Toxicon, 1999, 37, 187│K. Larsen, et al, Chem. Res. Toxicol., 2007, 20, 868 OH OH 2

O H

O

O

O

H

H

OH O

O

OH

H

O

H

H

OH

O

35

219 Dinophysistoxin 2 DTX2 Type: Polyether antibiotics. C44H68O13 Amorph. solid, mp 128–130 °C, [α]D = +15.49° (c = 0.213, CHCl3). Source: Dinoflagellates Dinophysis spp., mussel (blue mussel) Mytilus edulis. Pharm: Toxic (diarrhetic shellfish poison). Ref: M. Murata, et al, Bull. Jpn. Soc. Sci. Fish., 1982, 48, 549│T. Yasumoto, et al, Tetrahedron, 1985, 41, 1019│T. Hu, et al, Chem. Comm., 1992, 39│K. Larsen, et al, Chem. Res. Toxicol., 2007, 20, 868 OH OH

O

HO 2

H

9

O 7

H

10

O OH

O

14

O H

15

31

19 27

H

O H

O H

H

O 34 35S

OH

220 Dinophysistoxin 4 DTX4 Type: Polyether antibiotics. C66H104O30S3 Solid, mp > 300 °C (dec), [α]D26 = −12.0° (c = 0.1, MeOH). Source: Dinoflagellate Protocentrum lima. Pharm: Phosphatases PP1 inhibitor; phosphatase PP2A inhibitor; LD50 (mus) = 610 μg/kg. Ref: T. Hu, et al, J. Chem. Soc., Chem. Commun., 1995, 597

86

1 Polyketides

OH H O

H O

HO

H

H

O O

O

H O

OH

O O HO

S

OH

OH O

O

OH

O O

S HO O

O

O

OH O

O

O

O

S

O

OH

221 Dinophysistoxin 5a DTX5a Type: Polyether antibiotics. C65H101NO27S2 Source: Dinoflagellate Protocentrum maculusum [Syn. Protocentrum concavum] (culture). Pharm: Phosphatase PP1 inhibitor; phosphatase PP2A inhibitor. Ref: T. Hu, et al, JNP, 1992, 55, 1631│T. Hu, et al, Tet. Lett., 1995, 36, 9273

O O

H

H

HO

OH O

H

H O O

H

O

OH

OH

HO S O O

O

OH

O OH H N

O O O

O

O

O

O S O OH

OH

87

1.14 Polyether Antibiotics

222 Dinophysistoxin 5b DTX5b Type: Polyether antibiotics. C66H103NO27S2 Source: Dinoflagellate Protocentrum maculusum [Syn. Protocentrum concavum] (culture). Pharm: Phosphatase PP1 inhibitor; phosphatase PP2A inhibitor. Ref: T. Hu, et al, JNP, 1992, 55, 1631│T. Hu, et al, Tet. Lett., 1995, 36, 9273

H

O O

H

HO

OH O

H

H O O

H

OH O S O

O OH

O

O

O O HO

O

OH

OH

OH

O

O

N H

S O

O

O OH

223 20-Methylspirolide G Type: Polyether antibiotics. C43H63NO7 Source: Dinoflagellate Alexandrium ostenfeldii in contaminated shellfish. Pharm: Microalgal toxin. Ref: M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

N O

O

27

HO O 17

2 3

O

20

O OH

224 Okadaic acid Type: Polyether antibiotics. C44H68O13 Crystal (C6H6/CHCl3), mp 164–166 °C, [α]D20 = +53.3° (c = 0.182, CHCl3); mp 127–133 °C, [α]D25 = +28° (c = 0.38, CHCl3). Source: Dinoflagellate Protocentrum lima, sponges Halichondria okadai (Japan waters) and Halichondria melanodocia (Caribbean Sea). Pharm: Cytotoxic (hmn, epidermoid

88

1 Polyketides

carcinoma); protein phosphatase 1 and 2A inhibitors (KD = 0.96 nmol/L, MMOA: okadaic acid binding to proteins OABP1 and OABP2); LD50 (mus ip) = 192 μg/kg. Ref: K. Tachibana, et al, JACS, 1981, 103, 2469│ M. Murakami, et al, Bull. Jpn. Soc. Sci. Fish., 1982, 48, 69│T. Hu, et al, J. Chem. Soc., Chem. Commun., 1995, 597│ N. B. Perry, et al, Nat. Prod. Lett., 1998, 11, 305│S. V. Ley, et al, JCS Perkin I, 1998, 3907│N. Sugiyama, et al, Biochemistry, 2007, 46, 11410

OH O

O

O

OH

O

O

O OH

H

OH

H

O

H

OH

H

O

225 19-epi-Okadaic acid Type: Polyether antibiotics. C44H68O13 Source: Sponge Prorocentrum belizeanum. Pharm: Protein phosphatase 2A inhibitor (IC50 = 0.47 nmol/L). Ref: P. G. Cruz, et al, Org. Lett., 2007, 9, 3045│B. Paz, et al, Mar. Drugs, 2008, 6, 489

O H

H

OH O

O

H

OH

19

O H

O

H

OH

H

O

O O HO

OH

226 Okadaic acid 7-hydroxy-2,4-dimethyl-2E,4E-heptadienyl ester Type: Polyether antibiotics. C53H82O14 Amorph. powder, [α]D = +21.4° (c = 0.5, CHCl3). Source: Dinoflagellate Prorocentrum lima PL2. Pharm: Enzyme inhibitor; toxic; tumour promotor. Ref: M. Norte, et al, Tetrahedron, 1991, 47, 7437; 1994, 50, 9175

1.14 Polyether Antibiotics

89

O HO

2

O 9

O

10

OH 7

O

H 14

OH

H

O

O

H

OH

19

H

O

27

H HO

31

H

O

O 34

227 Okadaic acid 7-hydroxy-4-methyl-2-methylene-4E-heptenyl ester Type: Polyether antibiotics. C53H82O14 Amorph. powder, [α]D = +17.3° (c = 0.1, CHCl3). Source: Dinoflagellate Prorocentrum lima PL2. Pharm: Enzyme inhibitor; toxic; tumour promotor. Ref: M. Norte, et al, Tetrahedron, 1991, 47, 7437; 1994, 50, 9175│T. Hu, et al, JNP, 1992, 55, 1631 O HO 2

O 9

O

10

OH 7

O OH

H 14

H

O

O

H

H

O

OH

27

H 31

HO H

O

O 34

228 17-O-Palmitoyl-20-methylspirolide G Type: Polyether antibiotics. C59H93NO8 Source: Dinoflagellate Alexandrium ostenfeldii in contaminated shellfish. Pharm: Microalgal toxin. Ref: J. Aasen, et al, Rapid Commun. Mass Spectrom., 2006, 20, 1531│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

90

1 Polyketides

O

N O

27

O

O

O 17

2 3

20

O

O

OH

229 Pinnatoxin A Type: Polyether antibiotics. C41H61NO9 [α]D = +2.5° (c = 0.32, MeOH). Source: Greenshell mussels Pinna muricata (Okinawa), Pinna attenuata and Pinna atropurpurea (Principal toxin), oyster Crassostrea gigas (digestive glands, South Australian Pacific). Pharm: Ca2+ channel activator; smooth muscle contractant (showing tetrodotoxin-like effect); toxic (shellfish poisoning, highly); LD50 (mus, ip, acute toxicity) = 2.7 μg/mus. Ref: D. Uemura, et al, JACS, 1995, 117, 1155│J. A. McCauley, et al, JACS, 1998, 120, 7647│N. Takada, et al, Tet. Lett., 2001, 42, 3491│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39│A. I. Selwood, et al, J. Agric. Food Chem., 2010, 58, 6532

N O

H

H O O O

OH OH O

O

OH H

230 Pinnatoxin B Type: Polyether antibiotics. C42H64N2O9 Source: Greenshell mussel Pinna muricata (Okinawa). Pharm: Toxic (most active member of pinnatoxin family); LD50 (ip, mus) of Pinnatoxin B and C 1:1 mixture = 0.99 μg/kg. Ref: N. Takada, et al, Tet. Lett., 2001, 42, 3491│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39│F. Matsuura, et al, Org. Lett., 2006, 8, 332

1.14 Polyether Antibiotics

91

O

N S

H

OH

H O O O

NH2 OH O

O

OH H

231 Pinnatoxin C Type: Polyether antibiotics. C42H64N2O9 Source: Greenshell mussel Pinna muricata (Okinawa). Pharm: Toxin (most active member of pinnatoxin family); LD50 (ip, mus) of Pinnatoxin B and C 1:1 mixture = 0.99 μg/kg. Ref: N. Takada, et al, Tet. Lett., 2001, 42, 3491│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39│F. Matsuura, et al, Org. Lett., 2006, 8, 332

O

N R

H

OH

H O O O

NH2 OH O

O

OH H

232 Pinnatoxin D Type: Polyether antibiotics. C45H67NO10 Solid, [α]D = +42.5° (c = 0.5, MeOH). Source: Greenshell mussels Pinna muricata, Pinna attenuata and Pinna atropurpurea, oyster Crassostrea gigas (digestive glands, South Australian Pacific). Pharm: Ca2+ channel activator; toxic (highly, LD50 (mus, ip, acute toxicity) > 10 μg/mus, less toxic to mammals than other pinnatoxins); cytotoxic (murine leukaemia P388, IC50 = 2.5 μg/ mL, most potent). Ref: T. Chou, et al, Tet. Lett., 1996, 37, 4023; 4027│ M. Falk, et al, Tetrahedron, 2001, 57, 8659│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39│A. I. Selwood, et al, J. Agric. Food Chem., 2010, 58, 6532

92

1 Polyketides

O

N

OH

H O

O O

O

O

O

OH

OH

233 Pteriatoxin A Type: Polyether antibiotics. C45H70N2O10S Source: Greenshell mussel Pteria penguin (Okinawa). Pharm: Toxic (mice, from bivalve Pteria penguin, acutely). Ref: N. Takada, et al, Tet. Lett., 2001, 42, 3495│ M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39│F. Matsuura, et al, JACS, 2006, 128, 7463; 7742

O

N 34

2'

H

H

S OH

O

OH

O

O O

OH NH2

OH O

H

234 Pteriatoxin B Type: Polyether antibiotics. C45H70N2O10S Source: Greenshell mussel Pteria penguin (Okinawa). Pharm: Toxic (mice, from bivalve Pteria penguin, acutely). Ref: N. Takada, et al, Tet. Lett., 2001, 42, 3495│F. Matsuura, et al, JACS, 2006, 128, 7463; 7742

NH2

N 34

S

H

H O

O OH

O O H

OH 2'

OH OH O

O

1.14 Polyether Antibiotics

93

235 Pteriatoxin C Type: Polyether antibiotics. C45H70N2O10S Source: Greenshell mussel Pteria penguin (Okinawa). Pharm: Toxic (mice, from bivalve Pteria penguin, acutely). Ref: N. Takada, et al, Tet. Lett., 2001, 42, 3495│F. Matsuura, et al, JACS, 2006, 128, 7463; 7742

NH

N 34

S

OH

H

H

2'

O

O OH OH

O O OH

O

O H

236 Spirolide A Type: Polyether antibiotics. C42H61NO7 Source: Unidentified scallops (contaminated), an unidentified phytoplankton, dinflagellate Alexandrium ostenfeldii from unidentified phytoplankton assemblages (Nova Scotia). Pharm: Microalgal toxin; LD50 = 250 μg/kg. Ref: T. Hu, et al, J. Chem. Soc., Chem. Commun., 1995, 2159│ T. Hu, et al, JNP, 2001, 64, 308│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

N

O

2 3

O

27

O

19

H

O

O

OH 13

HO

237 Spirolide B Type: Polyether antibiotics. C42H64NO71+ Source: Dinoflagellate Alexandrium ostenfeldii in various contaminated shellfish (such as mussel Mytilus edulis, Placopecten magellanicus). Pharm: Type L-Ca channel activator (weak); toxic (phycotoxin). Ref: T. Hu, et al, J. Chem. Soc., Chem. Commun., 1995, 2159│ M. Falk, et al, Tetrahedron, 2001, 57, 8659│L. Sleno, et al, Anal. Bioanal. Chem., 2004, 378, 969; 977│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

94

1 Polyketides

H N

+

O

HO

O

O

O

O

OH

238 Spirolide C Type: Polyether antibiotics. C43H63NO7 Source: Unidentified scallops (contaminated), an unidentified phytoplankton, dinflagellate Alexandrium ostenfeldii from unidentified phytoplankton assemblages (Nova Scotia). Pharm: Microalgal toxin. Ref: T. Hu, et al, J. Chem. Soc., Chem. Commun., 1995, 2159│T. Hu, et al, JNP, 2001, 64, 308│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

N

O

2 3

O

27

O

19

H

O

O

OH 13

HO

239 Spirolide D Type: Polyether antibiotics. C43H66NO71+ Source: Dinoflagellate Alexandrium ostenfeldii in contaminated shellfish. Pharm: Type L-Ca2+ channel activator (weak); toxin. Ref: T. Hu, et al, J. Chem. Soc., Chem. Commun., 1995, 2159│ M. Falk, et al, Tetrahedron, 2001, 57, 8659│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

H N

+

O

HO

O

O

O OH

O

1.14 Polyether Antibiotics

95

240 Spirolide E Type: Polyether antibiotics. C42H63NO8 Source: Dinoflagellate Alexandrium ostenfeldii in contaminated shellfish. Pharm: Microalgal toxin. Ref: T. Hu, et al, Tet. Lett., 1996, 37, 7671│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) NH2 O

O

O

O

2 3

O

O OH

HO

241 Spirolide F Type: Polyether antibiotics. C42H65NO8 Source: Dinoflagellate Alexandrium ostenfeldii in contaminated shellfish. Pharm: Microalgal toxin. Ref: T. Hu, et al, Tet. Lett., 1996, 37, 7671│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) NH2 O

O

O

O

2 3

O

O

OH

HO

242 Spirolide G Type: Polyether antibiotics. C42H61NO7 Source: Dinoflagellate Alexandrium ostenfeldii in contaminated shellfish. Pharm: Microalgal toxin. Ref: J. Aasen, et al, Chem. Res. Toxicol., 2005, 18, 509│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

N O

O

27

HO O 17

2 3

O

20

O OH

96

1 Polyketides

1.15 Aplysiatoxins 243 Anhydrodebromoaplysiatoxin Type: Aplysiatoxins. C32H46O9 Cryst. (Et2O/pentane), mp 116–117.5 °C, [α]D = +25.6° (c = 0.02, MeOH). Source: Red alga Gracilaria coronopifolia. Pharm: Tumour promoter; causes diarrhea (mus); toxin. Ref: H. Nagai, et al, Biosci. Biotechnol. Biochem., 1998, 62, 1011

HO

O

3

4

O

O

O

O

O

O

OH

244 Aplysiatoxin Type: Aplysiatoxins. C32H47BrO10 Oil. Source: Cyanobacterium Lyngbya majuscula, sea hare Stylocheilus longicauda (Hawaii). Pharm: Toxin; LD100 (mus ip) = 0.3 mg/kg. Ref: Y. Kato, et al, Pure Appl. Chem., 1975, 41, 1│R. E. Moore, et al, JOC, 1984, 49, 2484│H. Nagai, et al, JNP, 1997, 60, 925

OH

OH

O O

O O

O

O

Br

O

OH

245 19-Bromoaplysiatoxin Type: Aplysiatoxins. C32H46Br2O10 Source: Cyanobacteria Schizothrix calcicola and Oscillatoria nigroviridis. Pharm: Toxin. Ref: J. S. Mynderse, et al, JOC, 1978, 43, 2301

1.15 Aplysiatoxins

97

Br HO HO O O

O

O

O

O

Br H

O H OH

246 17-Bromooscillatoxin A Type: Aplysiatoxins. C31H45BrO10 Source: Cyanobacteria Schizothrix calcicola and Oscillatoria nigroviridis. Pharm: Toxin. Ref: J. S. Mynderse, et al, JOC, 1978, 43, 2301 HO HO

O

O

O

O

Br

O

O

H

O H OH

247 Debromoaplysiatoxin Type: Aplysiatoxins. C32H48O10 Source: Cyanobacteria Lyngbya majuscula (shallowwater), Lyngbya gracilis. and other cyanobacteria, sea hare Stylocheilus longicauda. Pharm: Irritant; toxin; tumour promotor; LD50 (mus, ipr) = 0.5 mg/kg. Ref: Y. Kato, et al, JACS, 1974, 96, 2245│Y. Kato, et al, Pure Appl. Chem., 1975, 41, 1│ J. S. Mynderse, et al, Science, 1977, 196, 538│D. J. Faulkner, Tetrahedron, 1977, 33, 1421J. H. Cardellina, II, et al, Science, 1979, 204, 193│R. E. Moore, et al, JOC, 1984, 49, 2484│P. Park, et al, JACS, 1987, 109, 6205│H. Nagai, T. Yasumoto, et al, JNP, 1997, 60, 925 OH

O

OH O

O

HO H

O O O

H

O

98

1 Polyketides

248 17,19-Dibromooscillatoxin A 19,21-Dibromooscillatoxin A Type: Aplysiatoxins. C31H44Br2O10 Source: Cyanobacteria Schizothrix calcicola and Oscillatoria nigroviridis. Pharm: Toxin. Ref: J. S. Mynderse, et al, JOC, 1978, 43, 2301 Br HO

17

HO

O O

Br H O

O

O

O

19

H HO

O

249 Manauealide A Type: Aplysiatoxins. C32H47ClO10 [α]D = +13.8° (c = 0.55, MeOH). Source: Cyanobacterium Lyngbya majuscula. Pharm: Toxin. Ref: R. E. Moore, et al, JOC, 1984, 49, 2484│H. Nagai, T. Yasumoto, et al, JNP, 1997, 60, 925

Cl

O

OH

O O

O O

O

O

O

OH

250 Manauealide B Type: Aplysiatoxins. C32H47BrO10 [α]D = +21.3° (c = 0.3, CHCl3). Source: Cyanobacterium Lyngbya majuscula. Pharm: Toxin. Ref: R. E. Moore, et al, JOC, 1984, 49, 2484│H. Nagai, T. Yasumoto, et al, JNP, 1997, 60, 925

OH

OH

O O

O O

O

O

O Br OH

1.15 Aplysiatoxins

99

251 Manauealide C Type: Aplysiatoxins. C34H50O11 [α]D = +33.1° (c = 1.0, CHCl3). Source: Cyanobacterium Lyngbya majuscula. Pharm: Toxin. Ref: R. E. Moore, et al, JOC, 1984, 49, 2484│ H. Nagai, T. Yasumoto, et al, JNP, 1997, 60, 925 OH

O OH O

O O

O

O

O

OH

O

252 3-Methoxyaplysiatoxin Type: Aplysiatoxins. C33H49BrO10 Source: Cyanobacterium Trichodesmium erythraeum. Pharm: Antiviral (Chikungunya virus inhibitor). Ref: D. K. Gupta, et al, Mar. Drugs, 2014, 12, 115

O O O

O

O

O O

Br O HO

OH

253 3-Methoxydebromoaplysiatoxin Type: Aplysiatoxins. C33H50O10 Source: Cyanobacterium Trichodesmium erythraeum. Pharm: Antiviral (Chikungunya virus inhibitor). Ref: D. K. Gupta, et al, Mar. Drugs, 2014, 12, 115

O O O

O

O

O O O

OH

HO

100

1 Polyketides

254 31-Noroscillatoxin B Type: Aplysiatoxins. C31H44O10 Gum, Sol. MeOH, CHCl3; poorly sol. H2O, hexane. Source: Cyanobacteria Schizothrix calcicola and Oscillatoria nigroviridis (mixture). Pharm: Toxin. Ref: M. Entzeroth, et al, JOC, 1985, 50, 1255 HO O O

O

HO

O

O

O O OH

255 Oscillatoxin A Type: Aplysiatoxins. C31H46O10 Source: Cyanobacteria Schizothrix calcicola and Oscillatoria nigroviridis. Pharm: Toxic (major toxic metabolite). Ref: J. S. Mynderse, et al, JOC, 1978, 43, 2301 HO HO

O

O O

H O

O

O

HO

O

H

256 Oscillatoxin B1 Type: Aplysiatoxins. C32H46O10 Solid, mp 89 °C (dec). Source: Cyanobacterium Lyngbya majuscula (deep water). Pharm: Toxin. Ref: M. Entzeroth, et al, JOC, 1985, 50, 1255 HO O O

O

HO

O

O

O O OH

1.16 Aflatoxins and Related Polyketides

101

257 Oscillatoxin B2 Type: Aplysiatoxins. C32H46O10 Solid. Source: Cyanobacterium Lyngbya majuscula (deep water). Pharm: Toxin. Ref: M. Entzeroth, et al, JOC, 1985, 50, 1255 HO O O

O

HO

O

O

O O OH

1.16 Aflatoxins and Related Polyketides 258 Acyl-hemiacetal sterigmatocystin Type: Aflatoxins and related polyketides. C20H16O8 Light yellow amorphous powder, [α]D25 = −20° (c = 0.5, MeOH/CHCl3 5:3). Source: Marine-derived fungus Aspergillus versicolor MF359. Pharm: Antibacterial (Staphylococcus aureus (ATCC 6538), Bacillus subtilis (ATCC 6633), MRSA (clinical isolate 309) and Pseudomonas aeruginosa (ATCC 15692), all MICs > 100 μg/mL). Ref: F. H. Song, et al, Appl. Microbiol. Biotechnol., 2014, 98, 3753 O

O

OH

O

O

O O

O

259 Asperxanthone Type: Aflatoxins and related polyketides. C18H12O6 Amorph. powder, [α]D21 = −32° (c = 0.36, MeOH). Source: Marine-derived fungus Aspergillus sp. MF-93 (sea water, China). Pharm: Antiviral (inhibits TMV multiplication, 0.2 mg/mL, InRt = 62.9%). Ref: Z.-J. Wu, et al, Pest Manag. Sci., 2009, 65, 60

102

1 Polyketides

H OH

O

O

O

H O

O

260 Aversin Type: Aflatoxins and related polyketides. C20H16O7 Golden needles (Me2CO), mp 217 °C, [α]D20 = −222° (c = 0.248, CHCl3). Source: Marine-derived fungi Aspergillus versicolor from brown alga Sargassum thunbergii (Pingtan I., Fujian, China) and Aspergillus versicolor MF359. Pharm: Antibacterial (30 μg/disk: Escherichia coli, IZD = 6 mm, control Chloramphenicol, IZD = 32 mm; Staphylococcus aureus, IZD = 6 mm, Chloramphenicol, IZD = 31 mm); toxic (brine shrimp Artemia salina, 30 μg/disk, Lethal Rate = 17.5%); mycotoxin; Antibacterial (Staphylococcus aureus (ATCC 6538), Bacillus subtilis (ATCC 6633), MRSA (clinical isolate 309) and Pseudomonas aeruginosa (ATCC 15692), all MICs > 100 μg/mL) (Song, 2014). Ref: C. Shao, et al, Magn. Reson. Chem., 2007, 45, 434│F. -P. Miao, et al, Mar. Drugs, 2012, 10, 131│F. H. Song, et al, Appl. Microbiol. Biotechnol., 2014, 98, 3753 O

O

OH

H O O

O

H

O

261 Averufin Type: Aflatoxins and related polyketides. C20H16O7 Bright orange-red laths (Me2CO), mp 280–282 °C (dec), [α]D = 0°. Source: Marine-derived fungus Aspergillus niger (seawater, China). Pharm: Antiviral (TMV, moderate). Ref: Z. J. Wu, et al, Chin. J. Chem., 2008, 26, 759 O HO

O O OH

O

OH

262 6,8-Di-O-methylaverufin Type: Aflatoxins and related polyketides. C22H20O7 Cryst. (Me2CO), mp 208–209 °C. Source: Marine-derived fungus Aspergillus versicolor from brown alga Sargassum thunbergii (Pingtan I., Fujian, China), marine-derived fungus Penicillium flavidorsum SHK1-27. Pharm: Antibacterial (30 μg/disk: Escherichia coli, IZD = 10 mm, control

1.16 Aflatoxins and Related Polyketides

103

Chloramphenicol, IZD = 32 mm; Staphylococcus aureus, IZD = 10 mm, Chloramphenicol, IZD = 31 mm); toxic (brine shrimp Artemia salina, 30 μg/disk, Lethal Rate = 100%, LC50 = 0.5 μg/mL). Ref: F. -P. Miao, et al, Mar. Drugs, 2012, 10, 131│H. Ren, et al, Chin. J. Med. Chem. 2007, 17, 148

O

O

OH O

O

O O

263 6,8-Di-O-methylnidurufin Anthraquinone Type: Aflatoxins and related polyketides. C22H20O8 Cryst. (Me2CO/ hexane), mp 211–213 °C, [α]D25 = −77° (c = 0.15, CHCl3). Source: Marine-derived fungus Aspergillus versicolor from brown alga Sargassum thunbergii (Pingtan I., Fujian, China). Pharm: Antibacterial (30 μg/disk: Escherichia coli, IZD = 7 mm, control Chloramphenicol, IZD = 32 mm; Staphylococcus aureus, IZD = 7 mm, Chloramphenicol, IZD = 31 mm); toxic (brine shrimp Artemia salina, 30 μg/disk, Lethal Rate = 29.1%). Ref: F. -P. Miao, et al, Mar. Drugs, 2012, 10, 131│Y. Zhang, et al, Biosci., Biotechnol., Biochem., 2012, 76, 1774

O

O

OH

OH

O O

O O

264 Hemiacetal sterigmatocystin Type: Aflatoxins and related polyketides. C18H14O7 Light yellow amorphous powder, [α]D25 = −78.7° (c = 0.13, MeOH/CHCl3 5:3). Source: Marine-derived fungus Aspergillus versicolor MF359. Pharm: Antibacterial (Staphylococcus aureus (ATCC 6538), Bacillus subtilis (ATCC 6633), MRSA (clinical isolate 309) and Pseudomonas aeruginosa (ATCC 15692), all MICs > 100 μg/mL). Ref: F. H. Song, et al, Appl. Microbiol. Biotechnol., 2014, 98, 3753

104

1 Polyketides

O

O

OH

O

O O OH

265 5-Methoxydihydrosterigmatocystin Type: Aflatoxins and related polyketides. C19H16O7 Light yellow amorphous powder, [α]D25 = −168.7° (c = 0.10, MeOH/CHCl3 5:3). Source: Marine-derived fungus Aspergillus versicolor MF359. Pharm: Antibacterial (Staphylococcus aureus (ATCC 6538), MIC = 12.5 μg/mL, control Vancomycin, MIC = 1 μg/mL; Bacillus subtilis (ATCC 6633), MIC = 3.125 μg/mL, Vancomycin, MIC = 0.5 μg/mL; MRSA (clinical isolate 309), MIC > 100 μg/mL, Vancomycin, MIC = 1 μg/mL; Pseudomonas aeruginosa (ATCC 15692), MIC > 100 μg/mL, Vancomycin, MIC = 1 μg/mL). Ref: F. H. Song, et al, Appl. Microbiol. Biotechnol., 2014, 98, 3753│L. Xu, et al, Mar. Drugs, 2015, 13, 3479 (rev) O

O

OH

O

O

O O

266 6-O-Methylaverufin Type: Aflatoxins and related polyketides. C21H18O7 Source: Marine-derived fungus Aspergillus versicolor from brown alga Sargassum thunbergii (Pingtan I., Fujian, China). Pharm: Antibacterial (30 μg/disk: Escherichia coli, IZD = 10 mm, controlChloramphenicol, IZD = 32 mm; Staphylococcus aureus, IZD = 10 mm, Chloramphenicol, IZD = 31 mm); toxic (brine shrimp Artemia salina, 30 μg/disk, Lethal Rate = 38.5%). Ref: F. -P. Miao, et al, Mar. Drugs, 2012, 10, 131 OH

O

OH O

O

O O

1.16 Aflatoxins and Related Polyketides

105

267 Nidurufin Type: Aflatoxins and related polyketides. C20H16O7 Cryst. (MeOH/CHCl3), mp 188 °C. Source: An unidentified mangrove-derived fungus 2526 (South China Sea) from an unidentified mangrove, marine-derived fungus Aspergillus niger (seawater, China). Pharm: Antiviral (TMV, moderate). Ref: F. Zhu, et al, Youji Huaxue, 2004, 24, 1114│ M. Saleem, et al, NPR, 2007, 24, 1142 (rev)│Z. J. Wu, et al, Chin. J. Chem., 2008, 26, 759

OH

O

OH

OH H O

HO

O O

268 Sterigmatocystin Type: Aflatoxins and related polyketides. C18H12O6 Pale yellow needles, mp 246 °C (dec), [α]D21 = −387° (c = 0.424, CHCl3). Source: An unidentified marine-derived fungus 1850. Pharm: Mycotoxin; antifungal (Mycotypha microspore, 50 μg/disk, IZD = 11 mm); antialgal (Chlorella fusca, 50 μg/disk, IZD = 5 mm). Ref: Kralj, et al, JNP, 2006, 69, 995│F. Zhu, et al, Chem. Nat. Compd. (Engl. Transl.), 2007, 43, 132

O

OH O

O O

O

269 Versicolorin C Type: Aflatoxins and related polyketides. C18H12O7 Orange-red needles (Me2CO), mp 350 °C. Source: An unidentified mangrove-derived fungus 2526 (South China Sea) from an unidentified mangrove. Pharm: Mycotoxin. Ref: F. Zhu, et al, Youji Huaxue, 2004, 24, 1114│ M. Saleem, et al, NPR, 2007, 24, 1142 (rev) OH

O

OH

O O

OH O

106

1 Polyketides

1.17 Sorbicillin Polymers 270 Antibiotic JBIR 59 JBIR-59 Type: Sorbicillin polymers. C23H28O7 Amorph. yellow solid, [α]D27 = −350° (c = 0.1, MeOH). Source: Marine-derived fungus Penicillium citrinum SpI080624G1f01 from an unidentified sponge (class Demospongiae, Ishigaki I., Okinawa). Pharm: Antioxidant; glutamate toxicity inhibitor (neuronal hybridoma N18-RE-105 cells, EC50 = 71 μmol/L). Ref: J. Ueda, et al, J. Antibiot., 2010, 63, 203

OH O

O

H

O HO

OH

OH

271 Bisorbibutenolide Bislongiquinolide Type: Sorbicillin polymers. C28H32O8 Amorph. yellow powder, [α]D27 = +124.4° (c = 0.5, MeOH). Source: Marine-derived fungus Trichoderma sp. f-13 (Chinese sediment sample). Pharm: Cytotoxic (HL60 cell line, IC50 > 50 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 8.0%, negative control MeOH, sub-G1 = 2.3%). Ref: N. Abe, et al, Biosci., Biotechnol., Biochem., 1998, 62, 2120│S. Sperry, et al, JOC, 1998, 63, 10011│L. Du, et al, CPB, 2009, 57, 220 O O O

OH

HO H

HO 9

O

O

272 Bisorbicillinol Type: Sorbicillin polymers. C28H32O8 Amorph. yellow powder, [α]D28 = +195.2° (c = 0.5, MeOH). Source: Marine-derived fungus Trichoderma sp. f-13 (Chinese sediment sample). Pharm: Cytotoxic (HL60 cell line, IC50 > 50 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 7.3%, negative control MeOH, sub-G1 = 2.3%); antioxidant (DPPH scavenger). Ref: L. Du, et al, CPB, 2009, 57, 220│N. Abe, et al, Biosci., Biotechnol., Biochem., 1998, 62, 661; 2120

1.17 Sorbicillin Polymers

107

OH O O

O

OH

O

HO HO

273 Bisvertinolone Type: Sorbicillin polymers. C28H32O9 Source: Marine-derived fungi Trichoderma sp. f-13 (Chinese sediment sample) and Penicillium chrysogenum. Pharm: Cytotoxic (HL60 cell line, IC50 = 5.3 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 89.6%, negative control MeOH, subG1 = 2.3%); antioxidant (DPPH scavenger). Ref: M. Kontani, et al, Tet. Lett., 1994, 35, 2577│L. Du, et al, CPB, 2009, 57, 220

OH

OH

O

O

H

OH

HO

O

O OH

274 Bisvertinoquinol Type: Sorbicillin polymers. C28H34O8 Yellow triangular prisms, mp 160–163 °C (dec), [α]D20 = +329° (c = 0.2, CHCl3). Source: Marine-derived fungus Trichoderma sp. f-13 (Chinese sediment sample). Pharm: Cytotoxic (HL60 cell line, IC50 > 50 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, subG1 = 4.0%, negative control MeOH, sub-G1 = 2.3%). Ref: L. S. Trifonov, et al, Tetrahedron, 1983, 39, 4243│L. Du, et al, CPB, 2009, 57, 220 OH O O

OH

O HO HO

O

108

1 Polyketides

275 Chloctanspirone A Type: Sorbicillin polymers. C21H23ClO7 Yellow powder, [α]D25 = +304° (c = 0.1, MeOH). Source: Marine-derived fungus Penicillium terrestre (sediment, Jiaozhou Bay, Shandong, China). Pharm: Cytotoxic (HL60, IC50 = 9.2 μmol/L; A549, IC50 = 39.7 μmol/L). Ref: D. Li, et al, Tetrahedron, 2011, 67, 7913 HO O

O

OH HO

O

HO

Cl

276 Chloctanspirone B Type: Sorbicillin polymers. C21H23ClO7 Yellow powder, [α]D25 = +110° (c = 0.1, MeOH). Source: Marine-derived fungus Penicillium terrestre (sediment, Jiaozhou Bay, Shandong, China). Pharm: Cytotoxic (HL60, IC50 = 37.8 μmol/L; A549, IC50 > 100 μmol/L). Ref: D. Li, et al, Tetrahedron, 2011, 67, 7913 HO O

O OH

HO

O

HO

Cl

277 10,11-Dihydrobisvertinolone 2′′,3′′-Dihydrobisvertinolone Type: Sorbicillin polymers. C28H34O9 Yellow solid (MeOH), [α]D20 = −340° (c = 0.32, MeOH). Source: Marine-derived fungus Trichoderma sp. f-13 (Chinese sediment sample). Pharm: Cytotoxic (HL60 cell line, IC50 = 49.0 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, subG1 = 22.6%, negative control MeOH, sub-G1 = 2.3%). Ref: L. Du, et al, CPB, 2009, 57, 220

OH

O HO

OH

O

H

OH

O

O OH

1.17 Sorbicillin Polymers

109

278 Dihydrodemethylsorbicillin Type: Sorbicillin polymers. C13H16O3 Pale yellow powder. Source: Marine-derived fungus Phialocephala sp. (deep sea sediment, East Pacific Ocean). Pharm: Cytotoxic (P388, IC50 = (0.1 ± 0.1)μmol/L, control CDDP, IC50 = (0.04 ± 0.03)μmol/L; K562, IC50 = (4.8 ± 0.3)μmol/L, CDDP, IC50 = (0.08 ± 0.05)μmol/L). Ref: D. -H. Li, et al, Chem. Biodiversity, 2011, 8, 895 OH

O

HO

279 10,11-Dihydro-oxosorbiquinol Dihydrooxosorbiquinol Type: Sorbicillin polymers. C28H34O9 Brown syrup, [α]D20 = +94° (c = 0.08, MeOH). Source: Deep-sea fungus Phialocephala sp. FL30r (depth of 5059m, deep-sea sediments). Pharm: Cytotoxic (P388, IC50 = 40.3 μmol/L; A549, IC50 = 97.6 μmol/L; HL60, IC50 = 10.5 μmol/L; Bel7402, IC50 = 31.8 μmol/L; K562, IC50 = 68.2 μmol/L). Ref: D. H. Li, et al, J. Antibiot., 2007, 60, 317 O HO OH H

H O O

O

OH

HO

OH

280 2ʹ,3ʹ-Dihydrosorbicillin Type: Sorbicillin polymers. C14H18O3 Needles (Et2O/pentane), mp 67–70 °C. Source: Marine-derived fungus Trichoderma sp. f-13 (Chinese sediment sample). Pharm: Cytotoxic (HL60 cell line, IC50 > 50 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 4.5%, negative control MeOH, sub-G1 = 2.3%); mycotoxin. Ref: R. P. Maskey, et al, JNP, 2005, 68, 865│ L. Du, et al, CPB, 2009, 57, 220 OH

HO

O

110

1 Polyketides

281 Dihydrotrichodermolide Type: Sorbicillin polymers. C24H30O5 Deep yellow syrup, [α]D20 = +31.5° (c = 0.10, MeOH). Source: Marine-derived fungus Phialocephala sp. (deep sea sediment, East Pacific Ocean). Pharm: Cytotoxic (P388, IC50 = (11.5 ± 1.4)μmol/L, control CDDP, IC50 = (0.04 ± 0.03)μmol/L; K562, IC50 = (22.9 ± 0.8)μmol/L, CDDP, IC50 = (0.08 ± 0.05) μmol/L). Ref: D. -H. Li, et al, Chem. Biodiversity, 2011, 8, 895 O O

O

O O

282 Dihydrotrichodimerol Type: Sorbicillin polymers. C28H34O8 Yellow powder, mp 82–83 °C, mp 112–117 °C, [α]D = +99° (c = 0.01, MeOH). Source: Marine-derived fungi Trichoderma sp. f-13 (Chinese sediment sample) and Penicillium terrestre, an unidentified fungus B00853. Pharm: Cytotoxic (HL60 cell line, IC50 = 36.4 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 55.7%, negative control MeOH, sub-G1 = 2.3%). Ref: D. Lee, et al, J. Antibiot., 2005, 58, 615│L. Du, et al, CPB, 2009, 57, 220

HO

O

O OH

H

H

HO OH O O

283 Epoxysorbicillinol Type: Sorbicillin polymers. C14H16O5 Amorph. yellow powder, [α]D = +75° (c = 0.15, MeOH). Source: Marine-derived fungus Trichoderma longibrachiatum from sponge Haliclona sp. (Indonesia). Pharm: Pigment. Ref: S. Sperry, et al, JOC, 1998, 63, 10011│J. L. Wood, et al, JACS, 2001, 123, 2097

1.17 Sorbicillin Polymers

OH

111

O

O O OH

284 JBIR-124 Type: Sorbicillin polymers. C25H32O6 Source: Marine-derived fungus Penicillium citrinum from an unidentified sponge (Ishigaki I., Okinawa). Pharm: Antioxidant (DPPH scavenger). Ref: T. Kawahara,et al, J. Antibiot., 2012, 65, 45 O

OH

H

O

HO HO HO

285 Oxosorbiquinol Type: Sorbicillin polymers. C28H32O9 Brown syrup, [α]D20 = +255° (c = 0.1, MeOH). Source: Marine-derived fungus Phialocephala sp. FL30r (depth of 5059m, deep-sea sediments). Pharm: Cytotoxic (P388, IC50 = 29.9 μmol/L; A549, IC50 = 103.5 μmol/L; HL60, IC50 = 8.9 μmol/L; Bel7402, IC50 = 12.7 μmol/L; K562, IC50 = 56.3 μmol/L). Ref: D. H. Li, et al, J. Antibiot., 2007, 60, 317 O HO OH H

H O O

O

OH HO

OH

286 Sorbicatechol A Type: Sorbicillin polymers. C23H26O6 Source: Marine-derived fungus Penicillium chrysogenum PJX-17. Pharm: Antiviral (influenza virus (IFV) virus, IC50 = 85 μmol/L). Ref: J. Peng, et al, JNP, 2014, 77, 424

112

1 Polyketides

O HO

O

H OH

O OH

287 Sorbicatechol B Type: Sorbicillin polymers. C23H26O6 Source: Marine-derived fungus Penicillium chrysogenum PJX-17. Pharm: Antiviral (influenza virus (IFV) virus, IC50 = 113 μmol/L). Ref: J. Peng, et al, JNP, 2014, 77, 424 O

O HO

HO

O OH

H

288 Sorbicillactone A Type: Sorbicillin polymers. C21H23NO8 Yellow needles (MeOH aq), mp 205 °C (dec), [α]D20 = −939° (c = 0.2, MeOH). Source: Marine-derived fungus Penicillium chrysogenum (100g scale) from sponge Ircinia fasciculata. Pharm: Cytostatic (L5178Y); AntiHIV. Ref: G. Bringmann, et al, Prog. Mol. Subcell. Biol., 2003, 37, 231│ G. Bringmann, et al, Tetrahedron, 2005, 61, 7252│G. Bringmann, et al, Mar. Drugs, 2007, 5, 23 O

OH

H

O

HO

OH N H

O O

O

289 Sorbicillamine A Type: Sorbicillin polymers. C18H23NO4 Source: Deep-sea fungus Penicillium sp. F23-2. Pharm: Cytotoxic (HeLa, Bel7402, HCT116, P388 and HEK-293 cell lines, all IC50 > 10 μmol/L, weak). Ref: W. Guo, et al, JNP, 2013, 76, 2106

1.17 Sorbicillin Polymers

113

O HO OH H

O N H

290 (R)-Sorbicillamine B Type: Sorbicillin polymers. C28H35NO8 Source: Deep-sea fungus Penicillium sp. F23-2. Pharm: Cytotoxic (HeLa, Bel7402, HCT116, P388 and HEK-293 cell lines, all IC50 > 10 μmol/L, weak). Ref: W. Guo, et al, JNP, 2013, 76, 2106

OH

O O

O

H 17R

N H HO

O OH

OH

291 (S)-Sorbicillamine B Type: Sorbicillin polymers. C28H35NO8 Source: Deep-sea fungus Penicillium sp. F23-2. Pharm: Cytotoxic (HeLa, Bel7402, HCT116, P388 and HEK-293 cell lines, all IC50 > 10 μmol/L, weak). Ref: W. Guo, et al, JNP, 2013, 76, 2106

OH

O O

O

H 17S

N H HO

O OH

OH

292 Sorbicillamine C Type: Sorbicillin polymers. C28H33NO8 Source: Deep-sea fungus Penicillium sp. F23-2. Pharm: Cytotoxic (HeLa, Bel7402, HCT116, P388 and HEK-293 cell lines, all IC50 > 10 μmol/L, weak). Ref: W. Guo, et al, JNP, 2013, 76, 2106

114

1 Polyketides

OH

O O

O

H H 2N O OH

HO

OH

293 Sorbicillamine D Type: Sorbicillin polymers. C42H49NO12 Source: Deep-sea fungus Penicillium sp. F23-2. Pharm: Cytotoxic (HeLa, Bel7402, HCT116, P388 and HEK-293 cell lines, all IC50 > 10 μmol/L, weak). Ref: W. Guo, et al, JNP, 2013, 76, 2106 O HO O

H

O H H O H 2N

O H

HO

OH

HO

O

O HO

294 Sorbicillamine E Type: Sorbicillin polymers. C28H32O9 Source: Deep-sea fungus Penicillium sp. F23-2. Pharm: Cytotoxic (HeLa, Bel7402, HCT116, P388 and HEK-293 cell lines, all IC50 > 10 μmol/L, weak). Ref: W. Guo, et al, JNP, 2013, 76, 2106

OH

OH O H

O

O HO

O OH

OH

1.17 Sorbicillin Polymers

115

295 Sorbicillin Type: Sorbicillin polymers. C14H16O3 Orange plates or yellow cryst., mp 122–125 °C. Source: Marine-derived fungus Trichoderma sp. f-13 (Chinese sediment sample). Pharm: Cytotoxic (HL60, IC50 = 12.7 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 79.9%, negative control MeOH, sub-G1 = 2.3%), antioxidant (DPPH scavenger); mycotoxin. Ref: L. Du, et al, CPB, 2009, 57, 220 OH

O

HO

296 Sorbiterrin A Type: Sorbicillin polymers. C20H20O6 Source: Marine-derived fungus Penicillium terrestre (sediment, Jiaozhou Bay, Shandong, China). Pharm: AChE inhibitor (moderate). Ref: L. Chen, et al, Tet. Lett., 2012, 53, 325 O O

OH

H H

HO O

OH

297 Trichodermanone A Type: Sorbicillin polymers. C21H28O8 Yellowish viscous oil, [α]D22 = +203° (c = 0.24, MeOH). Source: Marine-derived fungus Trichoderma sp. from sponge Agelas dispar (Caribbean Sea). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: K. Neumann, et al, EurJOC, 2007, 2268 O

OH

HO

H O

O HO

7 10

OH

H

O

298 Trichodermanone B Type: Sorbicillin polymers. C21H28O8 Yellowish viscous oil, [α]D22 = +251° (c = 0.2, MeOH). Source: Marine-derived fungus Trichoderma sp. from sponge Agelas dispar

116

1 Polyketides

(Caribbean Sea). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: K. Neumann, et al, EurJOC, 2007, 2268 O

OH

HO

H O

H

7

O

OH

10

HO

O

299 Trichodermanone C Type: Sorbicillin polymers. C20H26O8 Yellowish viscous oil, [α]D22 = +265.7° (c = 0.5, MeOH). Source: Marine-derived fungus Trichoderma sp. from sponge Agelas dispar (Caribbean Sea). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: K. Neumann, et al, EurJOC, 2007, 2268 O

OH

HO

H O

HO HO

H

7

OH

10

O

300 Trichodimerol Type: Sorbicillin polymers. C28H32O8 Pale yellow cryst., mp 166–167 °C, [α]D = −376° (c = 0.26, MeOH). Source: Marine-derived fungi Trichoderma sp. f-13 (Chinese sediment sample) and Penicillium terrestre. Pharm: Cytotoxic (HL60 cell line, IC50 = 7.8 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 89.3%, negative control MeOH, sub-G1 = 2.3%); antioxidant (DPPH scavenger). Ref: Q. Gao, et al, JNP, 1995, 58, 1817│G. A. Warr, et al, J. Antibiot., 1996, 49, 234│L. Du, et al, CPB, 2009, 57, 220 HO

O

O OH

H

H

HO OH O O

1.17 Sorbicillin Polymers

117

301 Trisorbicillinone A Type: Sorbicillin polymers. C42H48O13 Brown syrup. Source: Deep-sea fungus Phialocephala sp. FL30r (depth of 5059m, deep-sea sediments). Pharm: Cytotoxic (MTT assay, HL60, IC50 = 9.10 μmol/L; P388, IC50 = 9.10 μmol/L; K562, IC50 = 30.2 μmol/L Bel7402, IC50 = 60.3 μmol/L; A549, IC50 > 100 μmol/L). Ref: D. Li, et al, Tet. Lett., 2007, 48, 5235 OH

O

H H HO HO

O H

O O

H HO

O O

OH

OH

OH

302 Trisorbicillinone B Type: Sorbicillin polymers. C42H48O13 Source: Marine-derived fungus Phialocephala sp. FL30r (depth of 5059m, deep-sea sediments). Pharm: Cytotoxic (P388, IC50 = 77.1 μmol/L; K562, IC50 = 88.2 μmol/L, very weak). Ref: D. H. Li, et al, Tetrahedron, 2010, 66, 5101

O OH H

O

OH OH

HO

O

HO H

O OH

OH HO O

303 Trisorbicillinone C Type: Sorbicillin polymers. C42H48O13 Source: Marine-derived fungus Phialocephala sp. FL30r (depth of 5059m, deep-sea sediments). Pharm: Cytotoxic (P388, IC50 = 78.3 μmol/L; K562, IC50 = 54.3 μmol/L, very weak). Ref: D. H. Li, et al, Tetrahedron, 2010, 66, 5101

118

1 Polyketides

O OH

O

H

OH OH

HO

O

HO H

O OH

OH HO O

304 Trisorbicillinone D Type: Sorbicillin polymers. C42H48O12 Source: Marine-derived fungus Phialocephala sp. FL30r (depth of 5059m, deep-sea sediments). Pharm: Cytotoxic (P388, IC50 = 65.7 μmol/L; K562, IC50 = 51.2 μmol/L, very weak). Ref: D. H. Li, et al, Tetrahedron, 2010, 66, 5101 OH

O

H H O O OH HO

OH OH

O

O

O OH

1.18 Phorbaside Polyketides 305 Phorbaside A Type: Phorbaside polyketides. C33H49ClO10 Solid, [α]D23 = +38° (c = 0.06, MeOH). Source: Sponge Phorbas sp. Pharm: Cytotoxic (HCT116, IC50 = 30.0 μmol/L). Ref: C. K. Skepper, et al, JACS, 2007, 129, 4150│J. B. MacMillan, et al, JOC, 2008, 73, 3699

1.18 Phorbaside Polyketides

OH

119

O

O 4A

OH

H

2A

O

OH O L-evalose

2

O

O

O

H

Cl

306 Phorbaside C Type: Phorbaside polyketides. C40H61ClO14 Source: Sponge Phorbas sp. Pharm: Cytotoxic (HCT116, IC50 = 2.0 μmol/L). Ref: J. B. MacMillan, et al, JOC, 2008, 73, 3699 O

OH

O H

O

O

4A

HO

2B OH

O

2A OH

2

O O

O

Cl

O

H

OH

307 Phorbaside D Type: Phorbaside polyketides. C34H48ClNO10 Source: Sponge Phorbas sp. Pharm: Cytotoxic (HCT116, IC50 = 61.9 μmol/L). Ref: J. B. MacMillan, et al, JOC, 2008, 73, 3699 O

O 4

A

O

OH

H

2A

HN

O

O

2

O O

O

O

H

Cl

308 Phorbaside E Type: Phorbaside polyketides. C40H61ClO14 Source: Sponge Phorbas sp. Pharm: Cytotoxic (HCT116, IC50 = 10.2 μmol/L). Ref: J. B. MacMillan, et al, JOC, 2008, 73, 3699

120

1 Polyketides

HO

O

O

4A

HO

OH

H

2A

O

OH O O

2

O

O

O

2B OH O H

Cl

1.19 Bafilomycins 309 Bafilomycin D Tubaymycin; Antibiotic 3D5 Type: Bafilomycins. C35H56O8 Microcryst. powder (diisopropyl ether), mp 106 °C, [α]D25 = −251° (c = 0.6, CHCl3). Source: Marine-derived streptomycete Streptomyces sp. RJA635, streptomycetes Streptomyces griseus and Streptomyces hygroscopicus. Pharm: Antibacterial (gram-positive bacteria), antifungal, insecticide, herbicide. Ref: A. Kretschmer, et al, Agric. Biol. Chem., 1985, 49, 2509│ M. G. O‘Shea, et al, J. Antibiot., 1997, 50, 1073│G. Carr, et al, JNP, 2010, 73, 422 O OH

O OH

O

OH

O

8

H

24

O

310 Bafilomycin F Type: Bafilomycins. C42H65NO13S Glass, [α]D20 = +10° (c = 0.3, MeOH). Source: Marine-derived streptomycete Streptomyces sp. RJA635. Pharm: Autophagy inhibitor. Ref: G. Carr, et al, JNP, 2010, 73, 422 O HO

H N

O

S

O O

OH O

OH

O

O

OH

O H

O

1.19 Bafilomycins

121

311 Bafilomycin G Type: Bafilomycins. C36H60O9 Glass, [α]D20 = −29° (c = 0.4, MeOH). Source: Marinederived streptomycete Streptomyces sp. RJA71. Pharm: Insecticide, antiparasite (worms and nematodes). Ref: G. Carr, et al, JNP, 2010, 73, 422 O OH

O

O

OH O O

H

OH

O

312 Bafilomycin I Type: Bafilomycins. C36H56O7 Glass, [α]D20 = +140° (c = 0.1, MeOH). Source: Marinederived streptomycete Streptomyces sp. RJA71. Pharm: Autophagy inhibitor. Ref: G. Carr, et al, JNP, 2010, 73, 422 O OH

O

O

O

H

O O

313 11ʹ,12ʹ-Dehydroelaiophylin Type: Bafilomycins. C56H90O15 Source: Marine-derived streptomycete Streptomyces sp. (sediment, Heishijiao Bay, Dalian, China). Pharm: Antibacterial (MRSA and VRE). Ref: C. Wu, et al, JNP, 2013, 76, 2153 O HO HO

O O

OH

OH

O O

O

O

O O

OH OH

314 Halichoblelide A Type: Bafilomycins. C55H88O18 Source: Marine-derived streptomycete Streptomyces hygroscopicus OUPS-N92 from fish Halichoeres bleekeri. Pharm: Cytotoxic (breast: HBC4, Log10 GI50 (mol/L) = −5.72; BSY1, Log10 GI50 (mol/L) = −5.78; HBC5, Log10 GI50 (mol/L) = −5.81; MCF7, Log10 GI50 (mol/L) = −5.70; MDA-MB-231, Log10 GI50 (mol/L) = −5.63; CNS: U251, Log10 GI50 = −5.73; SF268, Log10 GI50 (mol/L) = −5.74; SF295, Log10 GI50 (mol/L) = −5.75; SF539, Log10 GI50 (mol/L) = −5.96; SNB75, Log10 GI50 (mol/L) = −5.95; SNB78, Log10 GI50 (mol/L) = −5.85; colon: HCC2998, Log10 GI50 (mol/L) = −5.75; KM12, Log10 GI50 (mol/L) = −5.74; HT29, Log10 GI50 (mol/L) = −7.73; HCT15, Log10 GI50 (mol/L) = −5.75; HCT116, Log10 GI50 (mol/L) = −5.78; lung:

122

1 Polyketides

NCI-H23, Log10 GI50 (mol/L) = −5.68; NCI-H226, Log10 GI50 (mol/L) = −5.79; NCI-H522, Log10 GI50 (mol/L) = −5.73; NCI-H460, Log10 GI50 (mol/L) = −5.71; A549, Log10 GI50 (mol/L) = −5.72; DMS273, Log10 GI50 (mol/L) = −5.68; DMS114, Log10 GI50 (mol/L) = −5.81; Melanoma: LOX-IMVI, Log10 GI50 (mol/L) = −5.69; ovary: OVCAR-3, Log10 GI50 (mol/L) = −5.73; OVCAR-4, Log10 GI50 (mol/L) = −5.73; OVCAR-5, Log10 GI50 (mol/L) = −5.74; OVCAR-8, Log10 GI50 (mol/L) = −5.70; SK-OV-3, Log10 GI50 (mol/L) = −5.74; kidney: RXF-631L, Log10 GI50 (mol/L) = −5.74; ACHN, Log10 GI50 (mol/L) = −5.77; stomach: St4, Log10 GI50 (mol/L) = −5.71; MKN1, Log10 GI50 (mol/L) = −5.75; MKN7, Log10 GI50 = −5.77; MKN28, Log10 GI50 (mol/L) = −5.70; MKN45, Log10 GI50 (mol/L) = −5.73; MKN74, Log10 GI50 (mol/L) = −5.76; prostate: DU145, Log10 GI50 (mol/L) = −5.75; PC3, Log10 GI50 (mol/L) = −5.72; MG-MID (Mean value of log10 GI50 (mol/L) all cell lines tested): Log10 GI50 (mol/L) = −5.75; Delta (Difference of most sensitive cell and MG-MID) = 0.22; Range (Difference of most sensitive cell and least sensitive cell) = 0.33). Ref: T. Yamada, et al, Tet. Lett., 2002, 43, 1721; 2012, 53, 2842 O O

OH OH

HO O O

O O

HO

OH O

O O

O O

OH OH

315 Halichoblelide B Type: Bafilomycins. C51H84O15 Source: Marine-derived streptomycete Streptomyces hygroscopicus from fish Halichoeres bleekeri. Pharm: Cytotoxic (breast: HBC4, Log10 GI50 (mol/L) = −5.72; BSY1, Log10 GI50 (mol/L) = −5.71; HBC5, Log10 GI50 (mol/L) = −5.71; MCF7, Log10 GI50 (mol/L) = −5.69; MDA-MB-231, Log10 GI50 (mol/L) = −5.71; CNS: U251, Log10 GI50 (mol/L) = −5.75; SF268, Log10 GI50 (mol/L) = −5.76; SF295, Log10 GI50 (mol/L) = −5.74; SF539, Log10 GI50 (mol/L) = −5.59; SNB75, Log10 GI50 (mol/L) = −5.73; SNB78, Log10 GI50 (mol/L) = −5.63; colon: HCC2998, Log10 GI50 (mol/L) = −5.71; KM12, Log10 GI50 (mol/L) = −5.71; HT29, Log10 GI50 (mol/L) = −5.72; HCT15, Log10 GI50 (mol/L) = −5.71; HCT116, Log10 GI50 (mol/L) = −5.73; lung: NCI-H23, Log10 GI50 (mol/L) = −5.71; NCI-H226, Log10 GI50 (mol/L) = −5.74; NCI-H522, Log10 GI50 (mol/L) = −5.78; NCI-H460, Log10 GI50 (mol/L) = −5.75; A549, Log10 GI50 (mol/L) = −5.75; DMS273, Log10 GI50 (mol/L) = −5.76; DMS114, Log10 GI50 (mol/L) = −5.75; Melanoma: LOX-IMVI, Log10 GI50 (mol/L) = −5.69; ovary: OVCAR-3, Log10 GI50 (mol/L) = −5.71; OVCAR-4, Log10 GI50 (mol/L) = −5.65; OVCAR-5, Log10 GI50 (mol/L) = −5.72; OVCAR-8, Log10 GI50

1.19 Bafilomycins

123

(mol/L) = −5.70; SK-OV-3, Log10 GI50 (mol/L) = −5.70; kidney: RXF-631L, Log10 GI50 (mol/L) = −5.76; ACHN, Log10 GI50 (mol/L) = −5.74; stomach: St4, Log10 GI50 (mol/L) = −5.78; MKN1, Log10 GI50 (mol/L) = −5.76; MKN7, Log10 GI50 (mol/L) = −5.80; MKN28, Log10 GI50 (mol/L) = −5.72; MKN45, Log10 GI50 (mol/L) = −5.71; MKN74, Log10 GI50 (mol/L) = −5.75; prostate: DU145, Log10 GI50 (mol/L) = −5.71; PC3, Log10 GI50 (mol/L) = −5.72; MG-MID (Mean value of log10 GI50 (mol/L) all cell lines tested): Log10 GI50 (mol/L) = −5.72; Delta (Difference of most sensitive cell and MG-MID) = 0.08; Range (Difference of most sensitive cell and least sensitive cell) = 0.21). Ref: T. Yamada, et al, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 2001, 43, 455│T. Yamada, et al, Tet. Lett., 2002, 43, 1721; 2012, 53, 2842 O

O O O

O

OH

O

O

OH

O

O

O

O HO OH

316 Halichoblelide C Type: Bafilomycins. C50H82O15 Source: Marine-derived streptomycete Streptomyces hygroscopicus from fish Halichoeres bleekeri. Pharm: Cytotoxic (breast: HBC4, Log10 GI50 (mol/L) = −5.70; BSY1, Log10 GI50 (mol/L) = −6.20; HBC5, Log10 GI50 (mol/L) = −6.03; MCF7, Log10 GI50 (mol/L) = −5.73; MDA-MB-231, Log10 GI50 (mol/L) = −5.89; CNS: U251, Log10 GI50 (mol/L) = −5.84; SF268, Log10 GI50 (mol/L) = −5.65; SF295, Log10 GI50 (mol/L) = −5.78; SF539, Log10 GI50 (mol/L) = −5.79; SNB75, Log10 GI50 (mol/L) = −6.01; SNB78, Log10 GI50 (mol/L) = −5.56; colon: HCC2998, Log10 GI50 (mol/L) = −5.95; KM12, Log10 GI50 (mol/L) = −5.82; HT29, Log10 GI50 (mol/L) = −5.80; HCT15, Log10 GI50 (mol/L) = −5.75; HCT116, Log10 GI50 (mol/L) = −5.81; lung: NCIH23, Log10 GI50 (mol/L) = −5.90; NCI-H226, Log10 GI50 (mol/L) = −6.18; NCI-H522, Log10 GI50 (mol/L) = −6.32; NCI-H460, Log10 GI50 (mol/L) = −5.96; A549, Log10 GI50 (mol/L) = −6.12; DMS273, Log10 GI50 (mol/L) = −6.23; DMS114, Log10 GI50 (mol/L) = −6.56; Melanoma: LOX-IMVI, Log10 GI50 = −5.74; ovary: OVCAR-3, Log10 GI50 (mol/L) = −6.43; OVCAR-4, Log10 GI50 (mol/L) = −5.73; OVCAR-5, Log10 GI50 (mol/L) = −5.77; OVCAR-8, Log10 GI50 (mol/L) = −5.80; SK-OV-3, Log10 GI50 (mol/L) = −5.61; kidney: RXF-631L, Log10 GI50 (mol/L) = −6.52; ACHN, Log10 GI50 (mol/L) = −5.73; stomach: St4, Log10 GI50 (mol/L) = −5.85; MKN1, Log10 GI50 (mol/L) = −5.81; MKN7, Log10 GI50 (mol/L) = −5.88; MKN28, Log10 GI50 (mol/L) = −5.69; MKN45, Log10 GI50 (mol/L) = −6.26; MKN74, Log10 GI50 (mol/L) = −6.31; prostate: DU145, Log10 GI50 (mol/L) = −5.78; PC3, Log10 GI50 (mol/L) = −5.98; MG-MID (Mean value of log10 GI50 (mol/L) all cell lines tested): Log10 GI50 (mol/L) = −5.93; Delta (Difference of most sensitive cell and MG-MID) = 0.63; Range (Difference of

124

1 Polyketides

most sensitive cell and least sensitive cell) = 1.00). Ref: T. Yamada, et al, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 2001, 43, 455│T. Yamada, et al, Tet. Lett., 2002, 43, 1721; 2012, 53, 2842

O O

OH

O O

O

O

O

O

HO

HO

O O

O

HO

317 Leiodermatolide Type: Bafilomycins. C34H51NO8 Source: Lithistid sponge Leiodermatium sp. (Miami Terrace, Straits of Florida, depth of 401m, using the Johnson-Sea-Link submersible). Pharm: Antimitotic (potent, with a unique mode of action compared with other G2/M blocking agent); cytotoxic (very potent: A549, IC50 = 3.3 nmol/L; NCI-ADR-Res, 233 nmol/L; P388, IC50 = 3.3 nmol/L; PANC1, IC50 = 5.0 nmol/L; DLD-1, IC50 = 8.3 nmol/ L). Ref: I. Paterson,et al, Angew. Chem. Int. Ed. 2011, 50, 3219│ P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) O

H 2N O

OH HO O

O O

O

318 Micromonospolide A Type: Bafilomycins. C46H65NO13 Pale yellow needles, mp 141–142 °C (dec), [α]D25 = +14.3° (c = 0.63, MeOH). Source: Marine-derived bacterium Micromonospora sp. Pharm: Inhibits gastrulation of starfish (Asterina pectinifer embryo, MIC = 0.010 μg/mL). Ref: E. Ohta, et al, Tetrahedron, 2001, 57, 8463│E. Ohta, et al, Tet. Lett., 2001, 42, 4179 OH O

O

N H

O

O OH

O O OH O

21

O

OH

H O

8

1.20 Erythromycins

125

319 Micromonospolide B Type: Bafilomycins. C37H58O9 Colorless needles, mp 111–114 °C (diethyl ether-hexane), [α]D25 = +22° (c = 0.06, MeOH). Source: Marine-derived bacterium Micromonospora sp. Pharm: Inhibits gastrulation of starfish (Asterina pectinifer embryo, MIC = 0.011 μg/mL). Ref: E. Ohta, et al, Tetrahedron, 2001, 57, 8463 O OH

OH O

OH

O O

OH

O

320 Micromonospolide C Type: Bafilomycins. C37H56O8 White amorph. solid, mp 54–58 °C, [α]D25 = −23° (c = 0.1, MeOH). Source: Marine-derived bacterium Micromonospora sp. Pharm: Inhibits gastrulation of starfish (Asterina pectinifer embryo, MIC = 1.6 μg/mL). Ref: E. Ohta, et al, Tetrahedron, 2001, 57, 8463 O OH

O OH

O

OH

O

O

1.20 Erythromycins 321 Cochliomycin A Type: Erythromycins. C22H28O7 Source: Marine-derived fungus Cochliobolus lunatus from gorgonian Dichotella gemmacea (Weizhou Reef, South China Sea). Pharm: Antifoulant (barnacle Balanus amphitrite larvae, potent); antibacterial (Staphylococcus aureus, moderate); Ref: C. -L. Shao, et al, JNP, 2011, 74, 629 OH

O O

O

OH O O

126

1 Polyketides

1.21 Kijanimicins 322 Lobophorin A Type: Kijanimicins. C61H92N2O19 [α]D22 = −175° (c = 0.28, MeOH). Source: An unidentified marine-derived actinomycete CNB-837 (cultured, tropical marine) from brown alga Lobophora convolute (surface, Belize). Pharm: Anti-inflammatory (mus ear assay, inhibits topical PMA-induced edema). Ref: Z. -D. Jiang, et al, BoMCL, 1999, 9, 2003 OH O

O

HO

O

O

O

O

O H

OH H H N

O

H 3E

O

O

O

O

O

HO

O NH2

H HO

323 Lobophorin B 3B-De-O-digitoxosylkijanimicin Type: Kijanimicins. C61H90N2O21 Powder, [α]D = −129.5° (c = 0.3, MeOH). Source: An unidentified marine-derived actinomycete CNB-837 (cultured, tropical marine) from brown alga Lobophora convolute (surface, Belize). Pharm: Anti-inflammatory (mus ear assay, inhibits topical PMA-induced edema). Ref: Z. -D. Jiang, et al, BoMCL, 1999, 9, 2003 OH O

O

HO

O

O

O

O

O H

OH H H N

O

H O

O O O

N O

O

O O

HO H HO

1.21 Kijanimicins

127

324 Lobophorin G Type: Kijanimicins. C63H84N2O20 Source: Marine-derived streptomycete Streptomyces sp. (sediment, S. China Sea). Pharm: Antibacterial (Bacille Calmette-Guérin (BCG) strain of Mycobacterium bovis and Bacillus subtilis); antituberculosis (Mycobacterium tuberculosis, moderate). Ref: C. Chen, et al, Appl. Microbiol. Biotechnol., 2013, 97, 3885 OH O

O

HO

O

O

O

O H

O

O

O

H

OH

HN H 2N

H

O

O

HO O

O O H O O

325 Lobophorin H Type: Kijanimicins. C61H87N2O20 Source: Marine-derived streptomycete Streptomyces sp. (deep-sea sediment, S. China Sea). Pharm: Antibacterial (Bacillus subtilis, significant; Staphylococcus aureus, moderate). Ref: H. -Q. Pan, et al, Mar. Drugs, 2013, 11, 3891 OH O

O

HO O

O

O

H

OH O

O H O HO

HN O O

O

N

H

O

O

O

O H

O

H

128

1 Polyketides

326 Lobophorin I Type: Kijanimicins. C48H68N2O15 Source: Marine-derived streptomycete Streptomyces sp. (deep-sea sediment, S. China Sea). Pharm: Antibacterial (Bacillus subtilis and Staphylococcus aureus, much less active than Lobophorin H). Ref: H. -Q. Pan, et al, Mar. Drugs, 2013, 11, 3891

HO O HO H O

O

O H O

HN O

H

HO

O N

O

O

O

O H

HO

327 Tetromycin 1 Type: Kijanimicins. C50H65NO13 Light yellow amorph. solid, [α]D20 = −40.2° (c = 1.92, MeOH). Source: Marine-derived streptomycete Streptomyces axinellae Pol001 from sponge Axinella polypoides (Banyuls-sur-Mer, France). Pharm: Antitrypanosomal (Trypanosoma brucei brucei, 48h, IC50 = 29.30 μmol/L; 72h, IC50 = 31.69 μmol/L); antileishmanial (Leishmania major, IC50 > 100 μmol/L); cytotoxic (293T kidney epithelial cells, IC50 > 100 μmol/L; J774.1 macrophages, IC50 > 100 μmol/L). Ref: S. Pimentel-Elardo, et al, Mar. Drugs, 2011, 9, 1682 OH O OH

O O

NH

O HO

HO

O

O HO

O

O

328 Tetromycin 2 Type: Kijanimicins. C50H64O14 Light yellow amorph. solid, [α]D20 = −38.8° (c = 2.50, MeOH). Source: Marine-derived streptomycete Streptomyces axinellae Pol001 from sponge Axinella polypoides (Banyuls-sur-Mer, France). Pharm: Antitrypanosomal

1.21 Kijanimicins

129

(Trypanosoma brucei brucei, 48h, IC50 = 45.39 μmol/L; 72h, IC50 = 80.27 μmol/L); antileishmanial (Leishmania major, IC50 > 100 μmol/L); cytotoxic (293T kidney epithelial cells, IC50 > 100 μmol/L; J774.1 macrophages, IC50 = 50.21 μmol/L). Ref: S. Pimentel-Elardo, et al, Mar. Drugs, 2011, 9, 1682 OH O

OH

O O O

O HO

HO

O

O

O

O

O

329 Tetromycin 3 Type: Kijanimicins. C49H62O14 Light yellow amorph. solid, [α]D20 = −47.7° (c = 3.00, MeOH). Source: Marine-derived streptomycete Streptomyces axinellae Pol001 from sponge Axinella polypoides (Banyuls-sur-Mer, France). Pharm: Antitrypanosomal (Trypanosoma brucei brucei, 48h, IC50 = 26.90 μmol/L; 72h, IC50 = 30.35 μmol/L); antileishmanial(Leishmania major, IC50 = 36.80 μmol/L); cytotoxic (293T kidney epithelial cells, IC50 = 33.38 μmol/L; J774.1 macrophages, IC50 = 25.72 μmol/L); cathepsin L-like proteases inhibitors (Rhodesain, Ki = (2.10 ± 0.90)μmol/L; Falcipain-2, Ki = (1.65 ± 0.25)μmol/L; Cathepsin L, Ki = (15.0 ± 1.95)μmol/L; Cathepsin B, Ki = (0.57 ± 0.04)μmol/L). Ref: S. Pimentel-Elardo, et al, Mar. Drugs, 2011, 9, 1682 OH O

OH

O O O

O HO

HO

O

O O

OH

O

330 Tetromycin 4 Type: Kijanimicins. C49H62O14 Light yellow amorph. solid, [α]D20 = −44.1° (c = 3.83, MeOH). Source: Marine-derived streptomycete Streptomyces axinellae Pol001 from sponge Axinella polypoides (Banyuls-sur-Mer, France). Pharm: Antitrypanosomal (Trypanosoma brucei brucei, 48h, IC50 = 35.85 μmol/L; 72h, IC50 = 41.61 μmol/L); antileishmanial(Leishmania major, IC50 > 100 μmol/L); cytotoxic (293T kidney epithelial cells, IC50 = 58.58 μmol/L; J774.1 macrophages, IC50 = 27.54 μmol/L); cathepsin L-like proteases inhibitors (Rhodesain, Ki = (4.00 ± 0.30)μmol/L; Falcipain-2, Ki = (3.10 ± 0.20)μmol/L; Cathepsin L, Ki = (22.40 ± 0.80)μmol/L; Cathepsin B,

130

1 Polyketides

Ki = (1.60 ± 0.10)μmol/L; SARS-CoV-PL, Ki = (40.00 ± 6.50)μmol/L). Ref: S. Pimentel-Elardo, et al, Mar. Drugs, 2011, 9, 1682 OH O

OH

O O

O

O O

O

HO

HO

O

OH

O

331 Tetromycin B Type: Kijanimicins. C34H46O5 Light yellow amorph. solid, [α]D20 = −12.0° (c = 1.83, MeOH); mp 143–146 °C, [α]D24 = −0.2° (c = 0.59, MeOH). Source: Marine-derived streptomycete Streptomyces axinellae Pol001 from sponge Axinella polypoides (Banyuls-sur-Mer, France), terrestrial streptomycete (Streptomyces sp. MK67-CF9). Pharm: Antitrypanosomal (Trypanosoma brucei brucei, 48h, IC50 = 30.87 μmol/L; 72h, IC50 = 34.22 μmol/L); antileishmanial (Leishmania major, IC50 > 100 μmol/L); cytotoxic (293T kidney epithelial cells, IC50 = 71.77 μmol/L; J774.1 macrophages, IC50 = 20.20 μmol/L); cathepsin L-like proteases inhibitors (Rhodesain, Ki = (0.62 ± 0.03)μmol/L; Falcipain-2, Ki = (1.42 ± 0.01)μmol/L; Cathepsin L, Ki = (32.50 ± 0.05)μmol/L; Cathepsin B, Ki = (1.59 ± 0.09)μmol/L; SARS-CoV-PL, Ki = (69.60 ± 7.20)μmol/L). Ref: T. Takeuchi, et al, Jpn. Kokai Tokkyo Koho, 1996, JP 08165286│S. Pimentel-Elardo, et al, Mar. Drugs, 2011, 9, 1682

OH

O

H O

O

H OH

1.22 Resorcylic Acid Lactones 332 Aigialomycin A Type: Resorcylic acid lactones. C19H22O8 Cryst., mp 166–168 °C, [α]D = +17° (c = 0.5, CHCl3). Source: Marine-derived fungus Aigialus parvus BCC 5311 from an unidentified mangrove. Pharm: Cytotoxic (KB, IC50 > 20 μg/mL, control Ellipticine, IC50 = 0.46 μg/mL; BC-1 cell, IC50 = 11 μg/mL, control Ellipticine, IC50 = 0.60 μg/mL; Vero, IC50 = 4.3 μg/mL, control Ellipticine, IC50 = 1.0 μg/mL). Ref: M. Isaka, et al, JOC, 2002, 67, 1561

1.22 Resorcylic Acid Lactones

OH

131

O O 5E

O

OH O O

9

11

OH

333 Aigialomycin D Type: Resorcylic acid lactones. C18H22O6 Cryst., mp 83–85 °C, [α]D24 = −19° (c = 0.24, MeOH). Source: Marine-derived fungus Aigialus parvus BCC 5311 from an unidentified mangrove. Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 6.6 μg/mL, control Chloroquine diphosphate, IC50 = 0.16 μg/mL); cytotoxic (KB, IC50 = 3.0 μg/mL, control Ellipticine, IC50 = 0.46 μg/mL; BC-1 cell, IC50 = 18 μg/mL, control Ellipticine, IC50 = 0.60 μg/mL; Vero, IC50 = 1.8 μg/mL, control Ellipticine, IC50 = 1.0 μg/mL). Ref: M. Isaka, et al, JOC, 2002, 67, 1561│L. -X. Xu, et al, JNP, 2010, 73, 885 OH

O O 5E

HO 11E

OH OH

334 Aigialomycin E Type: Resorcylic acid lactones. C18H22O6 Amorph. solid, mp 91–94 °C, [α]D24 = +14° (c = 0.28, MeOH). Source: Marine-derived fungus Aigialus parvus BCC 5311 from an unidentified mangrove. Pharm: Cytotoxic (KB, IC50 > 20 μg/mL, control Ellipticine, IC50 = 0.46 μg/mL; BC-1, IC50 = 15 μg/mL, control Ellipticine, IC50 = 0.60 μg/mL; Vero, IC50 > 20 μg/mL, control Ellipticine, IC50 = 1.0 μg/mL). Ref: M. Isaka, et al, JOC, 2002, 67, 1561 OH

O O 5E

HO 11Z

OH OH

132

1 Polyketides

335 Curvulone A Type: Resorcylic acid lactones. C16H16O6 Cryst., mp 63–65 °C, [α]D25 = −76° (c = 0.75, EtOH). Source: Marine-derived fungus Curvularia sp. 6540 from red alga Gracilaria sp. (Gulf of Mexico at John’s Pass, Madeira Beach, Florida). Pharm: Antibacterial (gram positive bacterium Bacillus megaterium, final concentration 0.4 μg/mL, InRt = 92%); antifungal (final concentration 0.4 μg/mL: Microbotryum violaceum, InRt = 68%; Septoria tritici, InRt = 62%); antialgal (Chlorella fusca, final concentration 0.4 μg/mL, InRt = 59%). Ref: J. Dai, et al, EurJOC, 2010, 6928 HO

O O O O O H

336 Curvulone B Type: Resorcylic acid lactones. C17H22O6 Oil, [α]D25 = −22° (c = 0.27, EtOH). Source: Marine-derived fungus Curvularia sp. 6540 from red alga Gracilaria sp. (Gulf of Mexico at John’s Pass, Madeira Beach, Florida). Pharm: Antibacterial (gram positive bacterium Bacillus megaterium, final concentration 0.4 μg/mL, InRt = 88%); antifungal (final concentration 0.4 μg/mL: Microbotryum violaceum, InRt = 79%; Septoria tritici, InRt = 68%); antialgal (Chlorella fusca, final concentration 0.4 μg/mL, InRt = 74%). Ref: J. Dai, et al, EurJOC, 2010, 6928 O

O

HO

OH

O

O

337 10,11-Dehydrocurvularin Type: Resorcylic acid lactones. C16H18O5 Amorph. solid, [α]D22 = +79.1° (c = 0.4, MeOH). Source: Marine-derived fungus Curvularia sp. 6540 from red algae Gracilaria sp. (Gulf of Mexico at John’s Pass, Madeira Beach, Florida), marinederived fungus Curvularia sp. 768 from red alga Acanthophora spicifera. Pharm: Antibacterial (gram positive bacterium Bacillus megaterium, final concentration 0.4 μg/mL, InRt = 72%); antifungal (final concentration 0.4 μg/mL: Microbotryum violaceum, InRt = 60%; Septoria tritici, InRt = 43%); antialgal (Chlorella fusca, final concentration 0.4 μg/mL, InRt = 11%); cytotoxic (panel of 36 hmn tumour cell lines, mean IC50 = 1.25 μmol/L; bladder BXF-1218L, IC50 = 0.43 μmol/L; bladder BXF-T24,

1.22 Resorcylic Acid Lactones

133

IC50 = 0.5 μmol/L; glioblastoma CNXF-498NL, IC50 = 1.98 μmol/L; glioblastoma CNXF-SF268, IC50 = 0.36 μmol/L; colon CXF-HCT116, IC50 = 3.35 μmol/L; colon CXFHT29, IC50 = 3.22 μmol/L; stomach GXF-251L, IC50 = 0.81 μmol/L; head & neck HNXF-536L, IC50 = 1.84 μmol/L; lung LXF-1121L, IC50 = 1.56 μmol/L; lung LXF-289L, IC50 = 0.28 μmol/L; lung LXF-526L, IC50 = 1.11 μmol/L; lung LXF-529L, IC50 = 1.4 μmol/L; lung LXF-629L, IC50 = 2.17 μmol/L; lung LXF-H460, IC50 = 2.88 μmol/L; breast MAXF-401NL, IC50 = 0.4 μmol/L; breast MAXF-MCF7, IC50 = 2.63 μmol/L; melanoma MEXF-276L, IC50 = 5.45 μmol/L; melanoma MEXF394NL, IC50 = 0.68 μmol/L; melanoma MEXF-462NL, IC50 = 0.38 μmol/L; melanoma MEXF-514L, IC50 = 0.5 μmol/L; melanoma MEXF-520L, IC50 = 1.27 μmol/L; ovary OVXF-1619L, IC50 = 1.75 μmol/L; ovary OVXF-899L, IC50 = 0.58 μmol/L; ovary OVXFOVCAR3, IC50 = 1.84 μmol/L; pancreas PAXF-1657L, IC50 = 4.54 μmol/L; pancreas PAXF-PANC1, IC50 = 1.99 μmol/L; prostate PRXF-22RV1, IC50 = 0.76 μmol/L; prostate PRXF-DU145, IC50 = 0.81 μmol/L; prostate PRXF-LNCAP, IC50 = 3.75 μmol/L; prostate PRXF-PC3M, IC50 = 0.4 μmol/L; mesothelioma PXF-1752L, IC50 = 0.79 μmol/L; kidney RXF-1781L, IC50 = 2.14 μmol/L; kidney RXF-393NL, IC50 = 2.03 μmol/L; kidney RXF-486L, IC50 = 3.27 μmol/L; kidney RXF-944L, IC50 = 2.31 μmol/L; uterus UXF1138L, IC50 = 0.89 μmol/L) (Greve, 2008). Ref: J. Zhan, et al, J. Antibiot., 2004, 57, 341│H. Greve, et al, EurJOC, 2008, 5085│J. Dai, et al, EurJOC, 2010, 6928 O

O

HO 6 10 11

OH

O

338 10,11-Dehydro-13-hydroxycurvularin Type: Resorcylic acid lactones. C16H18O6 Amorph. solid, [α]D25 = +126.5° (c = 0.29, EtOH). Source: Marine-derived fungus Curvularia sp. 768 from red alga Acanthophora spicifera (Guam). Pharm: Cytotoxic (panel of 36 hmn tumour cell lines, mean IC50 = 30.06 μmol/L; bladder BXF-1218L, IC50 = 12.3 μmol/L; bladder BXF-T24, IC50 > 32.64 μmol/L; glioblastoma CNXF-498NL, IC50 = 13.88 μmol/L; glioblastoma CNXF-SF268, IC50 = 24.01 μmol/L; colon CXF-HCT116, IC50 > 32.64 μmol/L; colon CXF-HT29, IC50 > 32.64 μmol/L; stomach GXF-251L, IC50 > 32.64 μmol/L; head & neck HNXF-536L, IC50 = 15.55 μmol/L; lung LXF-1121L, IC50 = 23.67 μmol/L; lung LXF-289L, IC50 > 32.64 μmol/L; lung LXF-526L, IC50 > 32.64 μmol/L; lung LXF-529L, IC50 > 32.64 μmol/L; lung LXF-629L, IC50 > 32.64 μmol/L; lung LXF-H460, IC50 > 32.64 μmol/L; breast MAXF-401NL, IC50 = 16.99 μmol/L; breast MAXF-MCF7, IC50 > 32.64 μmol/L; melanoma MEXF-276L, IC50 = 21.47 μmol/L; melanoma MEXF394NL, IC50 = 14.31 μmol/L; melanoma MEXF-462NL, IC50 > 32.64 μmol/L; melanoma MEXF-514L, IC50 > 32.64 μmol/L; melanoma MEXF-520L, IC50 = 25.93 μmol/L;

134

1 Polyketides

ovary OVXF-1619L, IC50 > 32.64 μmol/L; ovary OVXF-899L, IC50 > 32.64 μmol/L; ovary OVXF-OVCAR3, IC50 > 32.64 μmol/L; pancreas PAXF-1657L, IC50 = 32.64 μmol/L; pancreas PAXF-PANC1, IC50 > 32.64 μmol/L; prostate PRXF-22RV1, IC50 > 32.64 μmol/L; prostate PRXF-DU145, IC50 > 32.64 μmol/L; prostate PRXFLNCAP, IC50 > 32.64 μmol/L; prostate PRXF-PC3M, IC50 > 32.64 μmol/L; mesothelioma PXF-1752L, IC50 = 28.18 μmol/L; kidney RXF-1781L, IC50 > 32.64 μmol/L; kidney RXF-393NL, IC50 > 32.64 μmol/L; kidney RXF-486L, IC50 > 32.64 μmol/L; kidney RXF-944L, IC50 = 33.94 μmol/L; uterus UXF-1138L, IC50 > 32.64 μmol/L). Ref: H. Greve, et al, EurJOC, 2008, 5085 O

O

HO

OH 6 10 11

OH

O

339 11α-Hydroxycurvularin Type: Resorcylic acid lactones. C16H20O6 Amorph. solid, [α]D22 = +6.9° (c = 0.47, EtOH). Source: Marine-derived fungus Curvularia sp. 768 from red alga Acanthophora spicifera (Guam). Pharm: Cytotoxic (panel of 36 hmn tumour cell lines, mean IC50 = 6.09 μmol/L; bladder BXF-1218L, IC50 = 7.34 μmol/L; bladder BXF-T24, IC50 = 3.14 μmol/L; glioblastoma CNXF-498NL, IC50 = 1.75 μmol/L; glioblastoma CNXF-SF268, IC50 = 2.96 μmol/L; colon CXF-HCT116, IC50 = 11.11 μmol/L; colon CXF-HT29, IC50 = 8.78 μmol/L; stomach GXF-251L, IC50 = 12.51 μmol/L; head & neck HNXF-536L, IC50 = 7.35 μmol/L; lung LXF-1121L, IC50 = 7.66 μmol/L; lung LXF289L, IC50 = 13.34 μmol/L; lung LXF-526L, IC50 = 9.63 μmol/L; lung LXF-529L, IC50 = 3.59 μmol/L; lung LXF-629L, IC50 = 7.93 μmol/L; lung LXF-H460, IC50 = 11.2 μmol/L; breast MAXF-401NL, IC50 = 1.86 μmol/L; breast MAXF-MCF7, IC50 = 4.44 μmol/L; melanoma MEXF-276L, IC50 = 14.04 μmol/L; melanoma MEXF394NL, IC50 = 0.92 μmol/L; melanoma MEXF-462NL, IC50 = 10.96 μmol/L; melanoma MEXF-514L, IC50 = 3.84 μmol/L; melanoma MEXF-520L, IC50 = 2.22 μmol/L; ovary OVXF-1619L, IC50 = 6.04 μmol/L; ovary OVXF-899L, IC50 = 10.61 μmol/L; ovary OVXF-OVCAR3, IC50 = 13.09 μmol/L; pancreas PAXF-1657L, IC50 = 14.14 μmol/L; pancreas PAXF-PANC1, IC50 = 4.02 μmol/L; prostate PRXF-22RV1, IC50 = 2.5 μmol/L; prostate PRXF-DU145, IC50 = 2.44 μmol/L; prostate PRXF-LNCAP, IC50 = 6.55 μmol/L; prostate PRXF-PC3M, IC50 = 3.24 μmol/L; mesothelioma PXF-1752L, IC50 = 16.21 μmol/L; kidney RXF-1781L, IC50 = 12.04 μmol/L; kidney RXF-393NL, IC50 = 11.9 μmol/L; kidney RXF-486L, IC50 = 9.07 μmol/L; kidney RXF-944L, IC50 = 4.57 μmol/L; uterus UXF-1138L, IC50 = 8.96 μmol/L). Ref: H. Greve, et al, EurJOC, 2008, 5085

1.22 Resorcylic Acid Lactones

O

135

16

O 1

15R

3

HO

11S 6

8

OH

10

H

O

OH

340 11β-Hydroxycurvularin Type: Resorcylic acid lactones. C16H20O6 Amorph. solid, [α]D22 = +25.2° (c = 0.26, EtOH). Source: Marine-derived fungus Curvularia sp. 6540 from red alga Gracilaria sp. (Gulf of Mexico at John’s Pass, Madeira Beach, Florida), marine-derived fungus Curvularia sp. 768 from red alga Acanthophora spicifera. Pharm: Antibacterial (gram-positive bacterium Bacillus megaterium, final concentration 0.4 μg/mL, InRt = 78%); antifungal (final concentration 0.4 μg/mL: Microbotryum violaceum, InRt = 80%; Septoria tritici, InRt = 56%); antialgal (Chlorella fusca, final concentration 0.4 μg/mL, InRt = 74%); cytotoxic (panel of 36 hmn tumour cell lines, mean IC50 = 12.99 μmol/L; bladder BXF-1218L, IC50 = 13.17 μmol/L; bladder BXF-T24, IC50 = 10.67 μmol/L; glioblastoma CNXF-498NL, IC50 = 11.34 μmol/L; glioblastoma CNXF-SF268, IC50 = 10.12 μmol/L; colon CXF-HCT116, IC50 = 21.2 μmol/L; colon CXF-HT29, IC50 = 13.0 μmol/L; stomach GXF-251L, IC50 = 16.66 μmol/L; head & neck HNXF-536L, IC50 = 8.0 μmol/L; lung LXF1121L, IC50 = 13.63 μmol/L; lung LXF-289L, IC50 = 17.92 μmol/L; lung LXF-526L, IC50 = 16.18 μmol/L; lung LXF-529L, IC50 = 9.78 μmol/L; lung LXF-629L, IC50 = 13.31 μmol/L; lung LXF-H460, IC50 = 17.11 μmol/L; breast MAXF-401NL, IC50 = 16.87 μmol/L; breast MAXF-MCF7, IC50 = 11.31 μmol/L; melanoma MEXF-276L, IC50 = 19.01 μmol/L; melanoma MEXF-394NL, IC50 = 2.05 μmol/L; melanoma MEXF-462NL, IC50 = 13.45 μmol/L; melanoma MEXF-514L, IC50 = 14.77 μmol/L; melanoma MEXF520L, IC50 = 10.26 μmol/L; ovary OVXF-1619L, IC50 = 8.02 μmol/L; ovary OVXF-899L, IC50 = 11.23 μmol/L; ovary OVXF-OVCAR3, IC50 = 23.46 μmol/L; pancreas PAXF-1657L, IC50 = 18.0 μmol/L; pancreas PAXF-PANC1, IC50 = 10.77 μmol/L; prostate PRXF-22RV1, IC50 = 11.45 μmol/L; prostate PRXF-DU145, IC50 = 9.77 μmol/L; prostate PRXF-LNCAP, IC50 = 20.46 μmol/L; prostate PRXF-PC3M, IC50 = 9.58 μmol/L; mesothelioma PXF1752L, IC50 = > 32.43 μmol/L; kidney RXF-1781L, IC50 = 15.73 μmol/L; kidney RXF393NL, IC50 = 15.5 μmol/L; kidney RXF-486L, IC50 = 14.88 μmol/L; kidney RXF-944L, IC50 = 11.84 μmol/L; uterus UXF-1138L, IC50 = 12.48 μmol/L). Ref: J. Zhan, et al, J. Antibiot., 2004, 57, 341│H. Greve, et al, EurJOC, 2008, 5085│J. Dai, et al, EurJOC, 2010, 6928 O

O HO

11R

OH

O

H OH

136

1 Polyketides

341 Hypothemycin Type: Resorcylic acid lactones. C19H22O8 Prisms (MeOH), mp 173–174 °C. Source: Mangrove-derived fungus Aigialus parvus BCC 5311. Pharm: Antiplasmodial (Plasmodium falciparum, IC50 = 2.2 μg/mL, control Chloroquine diphosphate, IC50 = 0.16 μg/mL); cytotoxic (KB, IC50 = 17 μg/mL, control Ellipticine, IC50 = 0.46 μg/mL; BC-1 cell, IC50 = 6.2 μg/mL, control Ellipticine, IC50 = 0.60 μg/mL; Vero, IC50 = 6.3 μg/mL, control Ellipticine, IC50 = 1.0 μg/mL); antifungal (against protozoa and plant pathogenic fungi); MEK kinase inhibitor. Ref: A. Zhao, et al, J. Antibiot., 1999, 52, 1086│ M. Isaka, et al, JOC, 2002, 67, 1561 OH

O O

O

OH

O

O

9

11

OH

342 Salicylihalamide A Type: Resorcylic acid lactones. C26H33NO5 [α]D = −35° (c = 0.7, MeOH). Source: Sponge Haliclona sp. (Western Australia). Pharm: Antineoplastic. (member of potentially important new class of antitumour agents). Ref: K. L. Erickson, et al, JOC, 1997, 62, 8188; 2001, 66, 1532 (correction) 17E

OH

H N

O O

O OH

15S 13R 12S

343 Salicylihalamide B Type: Resorcylic acid lactones. C26H33NO5 Amorph. solid, [α]D = −73° (c = 0.3, MeOH). Source: Sponge Haliclona sp. (Western Australia). Pharm: Antineoplastic. (member of potentially important new class of antitumour agents). Ref: K. L. Erickson, et al, JOC, 1997, 62, 8188; 2001, 66, 1532 (correction) 17Z

OH

H N

O

OH O

15S 13R 12S

O

1.22 Resorcylic Acid Lactones

137

344 (3R,5R)-Sonnerlactone Type: Resorcylic acid lactones. C14H18O5 Cryst. (MeOH aq), mp 146–147 °C, [α]D20 = +9° (c = 1, EtOH). Source: An unidentified mangrove-derived fungus Zh6-B1 from mangrove Sonneratia apetala (bark, Zhu Hai, Guangdong, China). Pharm: Cytotoxic (multi-drug resistant cancer cell line KV/MDR, 100 μmol/L, inhibits KV/MDR growth by 42.4%, might possess beneficial therapeutic potential against drug-resistant tumors). Ref: K. -K. Li, et al, BoMCL, 2010, 20, 3326 OH

O O

3 5

HO

OH

345 (3R,5S)-Sonnerlactone Type: Resorcylic acid lactones. C14H18O5 Powder, mp 159–160 °C, [α]D20 = +64° (c = 1, EtOH). Source: An unidentified mangrove-derived fungus Zh6-B1 from mangrove Sonneratia apetala (bark, Zhu Hai, Guangdong, China). Pharm: Cytotoxic (multi-drug resistant cancer cell line KV/MDR, 100 μmol/L, inhibits KV/MDR growth by 41.6%, might possess beneficial therapeutic potential against drug-resistant tumors). Ref: K. -K. Li, et al, BoMCL, 2010, 20, 3326 OH

O O

3 5

HO

OH

346 Sumalarin A Type: Resorcylic acid lactones. C20H26O8S Source: Mangrove-derived fungus Penicillium sumatrense from mangrove Lumnitzera racemosa (rhizosphere, WenChang, Hainan I., South China Sea). Pharm: Cytotoxic (several HTCLs). Ref: L. -H. Meng, et al, JNP, 2013, 76, 2145 O

O

HO

OH

O

S O

HO O

138

1 Polyketides

347 Sumalarin B Type: Resorcylic acid lactones. C25H32O11S Source: Mangrove-derived fungus Penicillium sumatrense from mangrove Lumnitzera racemosa (rhizosphere, WenChang, Hainan I., South China Sea). Pharm: Cytotoxic (several HTCLs). Ref: L. -H. Meng, et al, JNP, 2013, 76, 2145 O

O

HO

O OH O O

S

O O

O O

348 Sumalarin C Type: Resorcylic acid lactones. C19H24O8S Source: Mangrove-derived fungus Penicillium sumatrense from mangrove Lumnitzera racemosa (rhizosphere, WenChang, Hainan I., South China Sea). Pharm: Cytotoxic (several HTCLs). Ref: L. -H. Meng, et al, JNP, 2013, 76, 2145 O

O

HO

OH

O

S OH

HO O

1.23 Antimycins 349 Antimycin A19 Type: Antimycins. C28H40N2O8 Source: Marine-derived streptomycete Streptomyces antibioticus (sediment, Guangdong, China). Pharm: Antifungal (yeast Candida albicans, potent). Ref: L. -Y. Xu, et al, J. Antibiot., 2011, 64, 661 O O O H

N H

H N O

O

O O O

1.23 Antimycins

139

350 Antimycin A20 Type: Antimycins. C24H32N2O9 Source: Marine-derived streptomycete Streptomyces antibioticus (sediment, Guangdong, China). Pharm: Antifungal (yeast Candida albicans, potent). Ref: L. -Y. Xu, et al, J. Antibiot., 2011, 64, 661 O O O H

N H

OH

O

O

H N

O

O

O

351 Antimycin B2 Type: Antimycins. C26H30N2O10 Light-brown amorph. solid, [α]D25 = 0° (c = 0.1, CH3OH). Source: Mangrove-derived streptomycete Streptomyces lusitanus from mangrove Avicennia marina (sediment, Fujian, China). Pharm: Antibacterial (Staphylococcus aureus, MIC = 32.0 μg/mL, control Penicillin G, MIC = 0.25 μg/mL; Laribacter hongkongensis, MIC = 8.0 μg/mL, Penicillin G, MIC = 2.00 μg/mL). Ref: Z. Han, et al, Mar. Drugs, 2012, 10, 668 O H

N H

O

H N OH

O O

O

O

COOH

OH

352 Splenocin A Type: Antimycins. C26H28N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 5.0 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 5.0 nmol/L; cytotoxicity LD50 > 7100 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O O

O NH

O

O O O

140

1 Polyketides

353 Splenocin B Type: Antimycins. C28H32N2O9 Amorph. powder, [α]D = +68° (c = 0.1, MeOH). Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Anti-inflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 3.1 nmol/L; cytotoxicity LD50 > 1800 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O O

O NH

O

O O O

354 Splenocin C Type: Antimycins. C29H34N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 6.7 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 7.3 nmol/L; cytotoxicity LD50 > 560 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O

O

O NH

O

O O O

355 Splenocin D Type: Antimycins. C26H28N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 47.9 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 43.7 nmol/L; cytotoxicity LD50 > 550 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317

1.23 Antimycins

O

H N

141

OH O

O

O NH

O

O O O

356 Splenocin E Type: Antimycins. C28H32N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 16.6 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 15.9 nmol/L; cytotoxicity LD50 > 570 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O

O

O NH

O

O O O

357 Splenocin F Type: Antimycins. C29H34N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 9.4 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 6.8 nmol/L; cytotoxicity LD50 > 560 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O O

O NH

O

O O O

142

1 Polyketides

358 Splenocin G Type: Antimycins. C30H36N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 5.0 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 5.2 nmol/L; cytotoxicity LD50 > 550 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O

O

O NH

O

O O O

359 Splenocin H Type: Antimycins. C31H38N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 4.3 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 5.1 nmol/L; cytotoxicity LD50 > 1600 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O

O

O NH

O

O O O

360 Splenocin I Type: Antimycins. C31H30N2O9 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 15.8 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 15.2 nmol/L; cytotoxicity LD50 > 540 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317

1.23 Antimycins

O

H N

143

OH O

O

O NH

O

O O O

361 Splenocin J Type: Antimycins. C24H26N2O8 Amorph. powder. Source: Marine-derived streptomycete Streptomyces sp. CNQ-431 (sediment, La Jolla, California). Pharm: Antiinflammatory (pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine interleukin 5 (IL-5), IC50 = 1023 nmol/L; TH2 T lymphocyte cytokine interleukin 13 (IL-13), IC50 = 826 nmol/L; cytotoxicity LD50 > 6000 nmol/L). Ref: W. K. Strangman, et al, JMC, 2009, 52, 2317 O

H N

OH O O NH

OH

O O O

362 Streptobactin Type: Antimycins. C51H69N15O18 Source: Marine-derived streptomycete Streptomyces sp. from brown alga Analipus japonicus (Charatsunai beach, Muroran, Japan). Pharm: Siderophore; iron chelating activity (comparable to that of deferoxamine mesylate). Ref: Y. Matsuo, et al, JNP, 2011, 74, 2371 OH OH O

NH

HN NH

O

NH2

N H O

O

N H HO HO

O O

O

O

O

HN

NH H 2N

O

O

H N

N H

OH O

NH

OH

NH HN

NH2

144

1 Polyketides

363 Tribenarthin Type: Antimycins. C51H71N15O19 Source: Marine-derived streptomycete Streptomyces sp. from brown alga Analipus japonicus (Charatsunai beach, Muroran, Japan). Pharm: Siderophore. Ref: Y. Matsuo, et al, JNP, 2011, 74, 2371 OH OH O

NH

HN

NH2

N H

O

NH O

OH COOH NH H 2N

O

HN N H

O

O O

O

O N H

H N

OH O

NH

OH

NH

HO HN

NH2

HO

364 Urauchimycin A Type: Antimycins. C22H30N2O8 [α]D26 = +46.7° (c = 0.03, MeOH). Source: Marinederived streptomycete Streptomyces sp. Ni-80. Pharm: Phytotoxic; antifungal. Ref: N. Imamura, et al, J. Antibiot., 1993, 46, 241│K.-I. Hayashi, et al, J. Antibiot., 1999, 52, 325 O

H N

OH O O N H

OH

O O O

365 Urauchimycin B Type: Antimycins. C22H30N2O8 [α]D26 = +50° (c = 0.1, MeOH). Source: Marinederived streptomycetes Streptomyces sp. Ni-80 and Streptomyces sp. B1751. Pharm: Morphological differentiation inhibitor. Ref: N. Imamura, et al, J. Antibiot., 1993, 46, 241│C. B. F. Yao, et al, Z. Naturforsch., B, 2006, 61, 320

1.24 Bryostatins

O

H N

145

OH O O N H

OH

O O O

1.24 Bryostatins 366 Bryostatin 1 Type: Bryostatins. C47H68O17 Cryst. (CH2Cl2/MeOH), mp 230–235 °C, [α]D25 = +34.1° (c = 0.044, MeOH). Source: Bryozoans Bugula neritina and Amathia convoluta. Pharm: Pharmacology of Bryostatin 1 (Bryostatin 1 is emblematic of marine drugs potential, since it is exploited in non-correlated different diseases including cancer, HIV and neurodegenerative diseases); antineoplastic (promising results were obtained in phase II clinical trials when Bryostatin 1 was administered in combinations with cytotoxic agents such as cisplatin for the treatment of metastatic or unresectable stomach cancer); potent modulator of PKC (Bryostatin 1 awakens a fast short activation and self-phosphorylation of PKCs that consecutively induces PKCs membrane translocation with succeeding PKCs down-regulation. The down-regulation of PKC-δ isozyme shows a distinctive biphasic pattern: at low concentrations ‒ a down-regulation and at higher concentrations ‒ a mechanism of protection. So Bryostatin 1 is an attractive drug for pharmaceutical development); anti-AD preclinical studies (preclinical studies show that Bryostatin 1 is able to: (i) enhance spatial learning and long-term memory (rats, mice, rabbits and nudibranch), (ii) increase spinophilin and synaptophysin, synaptic proteins levels causing synapses structural changes, (iii) exert neuroprotective effects (AD transgenic mice), (iv) improve memory (APP/PS1 mice bearing Swedish mutation, transgenic mouse), (v) reduce Aβ levels (in monomeric Aβ-treated cells in vitro, in Tg2576 AD mouse in vivo), (vi) recover neurotrophic activity and synapses loss, (vii) prevent neuronal apoptosis, (viii) inhibit τ phosphorylation, (ix) enhance synaptogenesis); anti-AD clinical trials (3 clinical trials are going on: Trial A NCT00606164 Verified, Title: Safety, Efficacy, Pharmacokinetics, and Pharmacodynamics. Purpose: Find out single-dose safety and to determine how effective a single dose of Bryostatin 1, to find out what happens to Bryostatin 1 once it enters in bloodn and to measure PKC-C in the blood. Trial B NCT02221947 Terminated Verified. Title: Study to Evaluate the Preliminary Safety, Efficacy, PK and PD. Purpose: Evaluate the safety and tolerability following a single intravenous dose. Trial C NCT02431468 Verified. Title: A Study Assessing Bryostatin 1 in the Treatment of Moderately Severe to

146

1 Polyketides

Severe AD. Purpose: To compare different doses for the treatment of moderately severe to severe AD) (Russo, 2016). Ref: G. R. Pettit, et al, JACS, 1982, 104, 6846; 1984, 106, 6768│J. B. Smith, et al, Biochem. Biophys. Res. Commun., 1985, 132, 939│ M. Gschwendt, et al, Carcinogenesis (London), 1988, 9, 555│P. Russo, et al, Mar. Drugs, 2016, 14, 5 (review)

H

O

HO

O 7

O

O

O

O H

H

O OH

O

H

OH

O H

20

HO

O

O

O O

367 Bryostatin 2 Type: Bryostatins. C45H66O16 Fine cryst. (CH2Cl2/MeOH), mp 201–203 °C, [α]D25 = +50° (c = 0.05, MeOH). Source: Bryozoans Bugula neritina and Amathia convoluta. Pharm: Antineoplastic. Ref: G. R. Pettit, et al, JNP, 1983, 46, 528; 1986, 49, 231; 661│J. B. Smith, et al, Biochem. Biophys. Res. Commun., 1985, 132, 939

H

O

HO OH 7

O

O

O H

H

O OH

O

H

OH

O

O H

20

HO O

O O

368 20-epi-Bryostatin 3 Type: Bryostatins. C46H64O17 Amorph. solid, [α]D25 = +61° (c = 0.26, MeOH). Source: Bryozoan Bugula neritina. Pharm: Antineoplastic. Ref: G. N. Chmurny, et al, JOC, 1992, 57, 5260

1.24 Bryostatins

O O

H

OH

O

O

147

O O H

H

O OH O O

O

H

OH

O

20

H

OH

O O

369 Bryostatin 3 Type: Bryostatins. C46H64O17 Source: Bryozoan Bugula neritina. Pharm: Antineoplastic (P388). Ref: G. R. Pettit, et al, JOC, 1983, 48, 5354; 1991, 56, 1337│D. E. Schaufelberger, et al, JOC, 1991, 56, 2895│K. Ohmori, et al, Angew. Chem., Int. Ed., 2000, 29, 2290

HO O

O O

O

O

O O

OH O

OH

O

H O

O O

OH

O

370 Bryostatin 4 Type: Bryostatins. C46H70O17 Amorph. powder, mp 198–200 °C. Source: Sponge Lissodendoryx isodictyalis, Bryozoans Bugula neritina and Amathia convoluta, ascidian Aplidium californicum. Pharm: Cytotoxic (murine P388 lymphocytic leukaemia); protein phosphorylation stimulator; protein kinase C binding agent; polymorphonuclear leucocyte activator. Ref: G. R. Pettit, et al, JACS, 1982, 104, 6846; 1984, 106, 6768│G. R. Pettit, et al, JNP, 1983, 46, 528; 1986, 49, 231; 661│G. R. Pettit, et al, Pure Appl. Chem., 1986, 58, 415

148

1 Polyketides

OH

H

O O

H

O

O

O 7

H

O O

OH

OH

H

O

O

20

HO

O

O

O O

371 Bryostatin 5 Type: Bryostatins. C44H66O17 Needles (CH2Cl2/MeOH), mp 169–172 °C, [α]D27 = +106.92° (c = 0.028, MeOH). Source: Sponge Lissodendoryx isodictyalis, bryozoans Bugula neritina and Amathia convoluta, ascidian Aplidium californicum. Pharm: Cytotoxic (murine P388 lymphocytic leukaemia). Ref: G. R. Pettit, et al, JNP, 1983, 46, 528; 1986, 49, 231; 661│G. R. Pettit, et al, Pure Appl. Chem., 1986, 58, 415

OH

H

O O

H

O

O

O 7

H

O O

OH

O

OH

H

O

20

HO

O

O

O O

372 Bryostatin 6 NSC 362617 Type: Bryostatins. C43H64O17 Needles (CH2Cl2/MeOH), mp 172–175 °C, [α]D27 = +39.92° (c = 0.05, MeOH). Source: Sponge Lissodendoryx isodictyalis, bryozoans Bugula neritina and Amathia convoluta. Pharm: Antineoplastic (P388). Ref: G. R. Pettit, et al, Tetrahedron, 1985, 41, 985│G. R. Pettit, et al, Pure Appl. Chem., 1986, 58, 415│G. R. Pettit, et al, JOC, 1991, 56, 1337

1.24 Bryostatins

H

O O

H

OH

O

O H

O

149

O O

OH

H OH

O

O

O OH

O

H

O O

373 Bryostatin 7 Type: Bryostatins. C41H60O17 Needles (CH2Cl2/MeOH), mp 176–179 °C, [α]D27 = +39.92° (c = 0.05, MeOH). Source: Bryozoans Bugula neritina and Amathia convoluta. Pharm: Cytotoxic (murine lymphocytic leukaemia P388 cell lines). Ref: G .R. Pettit, et al, Can. J. Chem., 1985, 63, 1204

OH

H

O O

H

O

O

O 7

H

O O

OH

O

OH

H

O

20

HO

O

O

O O

374 Bryostatin 8 Type: Bryostatins. C45H68O17 Amorph. powder, mp 170–173 °C, [α]D27 = +49.9° (c = 0.04, MeOH). Source: Bryozoans Bugula neritina and Amathia convoluta. Pharm: Cytotoxic (murine P388 lymphocytic leukaemia); antineoplastic (P388). Ref: G. R. Pettit, et al, Tetrahedron, 1985, 41, 985│G. R. Pettit, et al, Pure Appl. Chem., 1986, 58, 415

150

1 Polyketides

OH

H

O O

H

O

O

O 7

H

O O

OH

O

OH

H

O

20

HO

O

O

O O

375 Bryostatin 9 Type: Bryostatins. C43H64O17 Needles, mp 159–162 °C, [α]D28 = +87.31° (c = 0.04, MeOH). Source: Bryozoan Bugula neritina. Pharm: Antineoplastic. Ref: G. R. Pettit, et al, JNP, 1983, 46, 528; 1986, 49, 231; 661 OH

H

O O

H

O

O

O 7

H

O O

OH

O

OH

H

O

20

HO

O

O

O O

376 Bryostatin 10 Type: Bryostatins. C42H64O15 Plates (MeOH/CH2Cl2), mp 161–164 °C, [α]D27 = +99.8° (c = 0.04, MeOH). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (in vitro P388 lymphocytic leukemia (PS) cells, ED50 = 7.6 × 10−4 μg/mL); toxic (fertilized sea urchin egg assay, ED50 = 0.16 μg/mL; P388, ED50 = 0.0018 μg/mL); stimulator steroidogenesis (fluorometrically steroidogenesis assay: primary cultured bovine adrenocortical cells, amount of hormone was determined fluorometrically using cortisol as standard, results were expressed as picomoles of cortisol production per 105cells/h (pmol/105cells/h), increase in ACTH-induced steroidogenesis by bryostatin 10 was found to be about 1.8 times (1141 pmol 105cells/h, the amount of steroidogenesis when stimulating only with 10 pmol/L ACTH is 635 pmol/105 cells/ h)); toxic (brine shrimp). Ref: G. R. Pettit, et al, JOC, 1987, 52, 2848│Y. Kamano, et al, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 1993, 35, 282│Y. Kamano, et al, JNP, 1995, 58, 1868

1.24 Bryostatins

H

O

OH

151

O 7

O

O

O

O

H

H

O

OH H OH O

O

19 20

H

21

HO O O

377 Bryostatin 11 Type: Bryostatins. C39H58O15 Needles (MeOH/CH2Cl2), mp 171–173 °C, [α]D27 = +42.5° (c = 0.05, MeOH). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (in vitro, P388 lymphocytic leukemia (PS) cells, ED50 = 1.8 × 10−5 μg/mL); antineoplastic (in vivo, P388 lymphocytic leukemia (PS) cells, 92.5 μg/kg, lead to 64% life extension). Ref: G. R. Pettit, et al, JOC, 1987, 52, 2848 H

O

OH

O 7

O

O

O

O

H

H

OH

O

H OH O

19 20

O

H

21

HO O O

378 Bryostatin 12 Type: Bryostatins. C49H72O17 [α]D27 = +39° (c = 0.108, MeOH). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (in vitro, P388 lymphocytic leukemia (PS) cells, ED50 = 0.014 μg/mL); antineoplastic (in vivo, P388 lymphocytic leukemia (PS) cells, 30–50 μg/kg, lead to 47–68% life extension); RNA biosynthisis inhibitor. Ref: G. R. Pettit, et al, JOC, 1987, 52, 2854

152

1 Polyketides

H

O

OH

O 7

O

O

O

O

H

H

O

OH H OH O

O

O

19 20

H

21

O

HO O O

379 Bryostatin 13 Type: Bryostatins. C41H62O15 Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (in vitro, P388 lymphocytic leukemia (PS) cells, ED50 = 0.0054 μg/mL); antineoplastic (in vivo, P388 lymphocytic leukemia (PS) cells, 92.5 μg/kg, lead to 64% life extension). Ref: G. R. Pettit, et al, JOC, 1987, 52, 2854 H

O

OH

O 7

O

O

O

O

H

H

OH

O

H OH

O

O

19 20

H

21

HO O O

380 Bryostatin 14 Type: Bryostatins. C42H64O16 Amorph. powder, mp 174–176 °C, [α]D22 = +41.3° (c = 0.9, CH2Cl2). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic. Ref: G. R. Pettit, et al, Tetrahedron, 1991, 47, 3601 H

O

HO

O 7

O

O

O

O H

H

O OH H O 20

HO

HO O O

OH O H

1.24 Bryostatins

153

381 Bryostatin 15 Type: Bryostatins. C47H68O18 [α]D25 = +26° (c = 0.3, MeOH). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic. Ref: G. R. Pettit, et al, Tetrahedron, 1991, 47, 3601

H

O

HO O 7

O

O

O

O

H

H O OH

OH

O

H

OH O H

20

O

HO O

O O

382 Bryostatin 16 Type: Bryostatins. C42H62O14 [α]D = +84° (c = 0.4, MeOH). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (murine lymphocytic leukemia P388 cell lines, ED50 = 9.3 × 10−3 μg/mL). Ref: G. R. Pettit, et al, JNP, 1996, 59, 286

OH

H

O O

H

O

O

O 7

H

O O

19

O

OH

H

20

O

HO O O

383 Bryostatin 17 Type: Bryostatins. C42H62O14 [α]D = +231° (c = 0.3, MeOH). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (murine lymphocytic leukemia P388 cell lines, ED50 = 1.9 × 10−2 μg/mL). Ref: G. R. Pettit, et al, JNP, 1996, 59, 286

154

1 Polyketides

OH

H

O H

O

O

O

H

O 7

O O

O

OH

H

O

19 20

HO

21Z

O O

384 Bryostatin 18 Type: Bryostatins. C42H64O15 [α]D = +136° (c = 0.7, MeOH). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (murine lymphocytic leukemia P388 cell lines, ED50 = 3.3 × 10−3 μg/mL). Ref: G. R. Pettit, et al, JNP, 1996, 59, 286 OH

H

O H

O

O

O

H

O 7

O O

OH H O

OH

O

20

HO

21Z

O O

385 Miyakolide Type: Bryostatins. C36H54O12 Cryst. (CH2Cl2/MeOH), mp 197–199 °C, [α]D24 = −24° (c = 1.05, CHCl3), Sol. MeOH, CHCl3; poorly sol. H2O. Source: Sponge Polyfibrospongia sp. (Japan waters). Pharm: Cytotoxic (weak); antineoplastic (mus, P388 leukemia, in vitro IC50 = 17.5 μg/mL, in vivo T/C = 127% at 800 μg/kg). Ref: T. Higa, et al, JACS, 1992, 114, 7587

H O

H

OH

O OH

O O

OH

O

O

H

H OH

O O

1.26 Fujimycins

155

1.25 Copiamycins 386 Azalomycin F4a 2-ethylpentyl ester Type: Copiamycins. C63H109N3O17 White amorph. powder, [α]D30 = +4.7° (c = 0.1, MeOH). Source: Mangrove-derived streptomycete Streptomyces sp. from mangrove Heritiera globosa (rhizosphere soil, Wenchang, Hainan, China). Pharm: Antifungal (yeast Candida albicans, MIC = 2.34 μg/mL); cytotoxic (HCT116 cell line, IC50 = 5.64 μg/mL). Ref: G. J. Yuan, et al, Chin. Chem. Lett., 2010, 21, 947│G. Yuan, et al, Magn. Reson. Chem., 2011, 49, 30 O O

O OH

OH OH OH

O O

OH O

HO HO

N

OH

HO OH

O

N H

H 2N

387 Azalomycin F5a 2-ethylpentyl ester Type: Copiamycins. C64H111N3O17 White amorph. powder, [α]D30 = +4.7° (c = 0.1, MeOH). Source: Mangrove-derived streptomycete Streptomyces sp. from mangrove Heritiera globosa (rhizosphere soil, Wenchang, Hainan, China). Pharm: Antifungal (yeast Candida albicans, MIC = 12.5 μg/mL); cytotoxic (HCT116 cell line, IC50 = 2.58 μg/mL). Ref: G. Yuan, et al, Magn. Reson. Chem., 2011, 49, 30 O O

O OH

OH OH OH

O O

OH O

HO HO

N HN

OH

O

HO OH

N H

1.26 Fujimycins 388 Nocardiopsin B Type: Fujimycins. C33H53NO7 Oil, [α]D = −72° (c = 0.1, MeOH). Source: Marinederived actinomycete Nocardiopsis sp. CMB-M0232. Pharm: Immunophilin FKBP12binding agent. Ref: R. Raju, et al, Chem. Eur. J., 2010, 16, 3194

156

1 Polyketides

HO

HO O

28

O

O O N

O

1.27 Amphidinolides 389 Amphidinolactone B Type: Amphidinolides. C32H54O8 Amorph. solid. Source: Dinoflagellate Amphidinium sp. Y-25. Pharm: Cytotoxic (L1210, IC50 = 3.3 μg/mL; KB, IC50 = 5.3 μg/mL). Ref: Y. Takahashi, et al, J. Antibiot., 2007, 60, 376│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) OH

O O OH HO O OH

O

390 Amphidinolide A Type: Amphidinolides. C31H46O7 Needles, mp 130–133 °C, [α]D24 = +46° (c = 1, CHCl3). Source: Dinoflagellate Amphidinium sp. Y-5 from marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 2.0 μg/mL; KB, IC50 = 5.7 μg/mL); antineoplastic (number of human cancer cell lines). Ref: J. Kobayashi, et al, Tet. Lett., 1986, 27, 5755│J. Kobayashi, et al, JNP, 1991, 54, 1435│B. M. Trost, et al, JACS, 2005, 127, 13589; 13598│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O HO

O

O

HO HO OH

391 Amphidinolide B Amphidinolide B1 Type: Amphidinolides. C32H50O8 Needles (hexane/CH2Cl2), mp 82–84 °C, [α]D25 = −62.5° (c = 0.4, CHCl3), [α]D25 = −45° (c = 1, CHCl3). Source: Dinoflagellate Amphidinium sp. (yield = 0.14%dw). Pharm: Cytotoxic (hmn colon

1.27 Amphidinolides

157

tumor cell line HCT116, IC50 = 0.122 μg/mL) (Bauer, 1994); cytotoxic (L1210, IC50 = 0.14 ng/mL) (Ishibashi, 1987); cytotoxic (cultured tumor cells in vitro, IC50 = 0.00014–0.0045 g/mL) (Shimbo, 2005). Ref: M. Ishibashi,et al, J. Chem. SOC. Chem. Commun. 1987, 1127.│J. Kobayashi, et al, JOC, 1991, 56, 5221; 2002, 67, 6585│I. Bauer, et al, JACS, 1994, 116, 2657│K. Shimbo, et al, BoMC, 2005, 13, 5066│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) OH OH

O OH

16

18 22

HO 26

H 7

H

6 1

O

O O

392 Amphidinolide B2 Type: Amphidinolides. C32H50O8 Amorph. solid, [α]D25 = −43.9° (c = 0.4, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (HCT116, IC50 = 7.5 μg/mL). Ref: I. Bauer, et al, JACS, 1994, 116, 2657 OH OH

O OH

16

18 22

HO 26

H 7

H

6 1

O

O O

393 Amphidinolide B3 Type: Amphidinolides. C32H50O8 [α]D25 = −69.4° (c = 0.2, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (HCT116, IC50 = 0.206 μg/mL). Ref: I. Bauer, et al, JACS, 1994, 116, 2657 OH OH

O OH

16

18 22

HO 26

H 7

H

6 1

O O

O

158

1 Polyketides

394 Amphidinolide B4 Amphidinolide H Type: Amphidinolides. C32H50O7 Oil, [α]D23 = −13° (c = 0.2, CHCl3). Source: Dinoflagellates Amphidinium spp. Y-25 and Amphidinium sp. Pharm: Cytotoxic (murine lymphoma L1210, IC50 = 0.00012 μg/mL; human epidermoid carcinoma KB cells, IC50 = 0.001 μg/mL); cytotoxic (cultured tumor cells in vitro, IC50 = 0.00014–0.0045 μg/mL); binds to actin covalently. Ref: M. Tsuda,et al, Mar. Drugs, 2005, 3, 1│K. Oguchi, et al, JNP, 2007, 70, 1676│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)

OH

O OH

18S

16S

21R 22S

HO

23R 26

11R

8S 9S

25R

6 7

O 2

O

O

395 Amphidinolide B5 Type: Amphidinolides. C32H50O7 Oil, [α]D = −25° (c = 0.2, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (murine lymphoma L1210, IC50 = 0.0014 μg/mL; human epidermoid carcinoma KB cells, IC50 = 0.004 μg/mL). Ref: M. Tsuda,et al, Mar. Drugs, 2005, 3, 1│J. Kobayashi, et al, J. Antibiot., 2008, 61 (5), 271 (rev)

OH

O OH

16

18 22

HO H

26

O H

O

7

6

O

396 Amphidinolide B6 Type: Amphidinolides. C32H54O8 Oil, [α]D17 = +29° (c = 0.01, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (hmn B lymphocyte DG-75 cells, IC50 = 0.02 μg/mL). Ref: K. Oguchi, et al, JNP, 2007, 70, 1676

1.27 Amphidinolides

159

O

OH

OH 16

18 22

HO 26

H 7

H

6 1

3S

O

2S

O

OH

O

397 Amphidinolide B7 Type: Amphidinolides. C32H52O7 Oil, [α]D = −22° (c = 0.01, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (hmn B lymphocyte DG-75 cells, IC50 = 0.4 μg/mL). Ref: K. Oguchi, et al, JNP, 2007, 70, 1676 O

OH

OH 16

18 22

HO 26

H 7

H

6 1

O

O O

398 Amphidinolide C Type: Amphidinolides. C41H62O10 Amorph., [α]D26 = −106° (c = 1, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.0058 μg/mL; KB, IC50 = 0.0046 μg/mL); ATP-ase activator. Ref: J. Kobayashi, et al, JACS, 1988, 110, 490│T. Kubota, et al, Org. Lett., 2001, 3, 1363│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O O H OH

OH O

OH O OH

H

29

H

O O

160

1 Polyketides

399 Amphidinolide C2 Type: Amphidinolides. C43H64O11 Colorless oil. Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.8 μg/mL; KB, IC50 = 3 μg/mL). Ref: T. Kubota, et al, Mar. Drugs, 2004, 2, 83│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O O

O

H O

OH O

OH O OH

29

H

H

O O

400 Amphidinolide C3 Type: Amphidinolides. C41H60O10 Source: Dinoflagellate Amphidinium sp. Y-56 from marine acoel flatworm Amphiscolops sp. (Zanpa, Okinawa). Pharm: Cytotoxic (P388, L1210 and KB cells). Ref: T. Kubota, et al, Heterocycles, 2010, 82, 333 O O

OH

O O

OH O

O

OH

O

401 Amphidinolide D Type: Amphidinolides. C32H50O8 Amorph. solid, [α]D30 = −30° (c = 0.5, CHCl3). Source: Dinoflagellate Amphidinium sp., marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 0.019 μg/mL; KB, IC50 = 0.08 μg/mL). Ref: J. Kobayashi, et al, JNP, 1989, 52, 1036│J. Kobayashi, et al, JOC, 2002, 67, 6585│ J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) OH OH

O OH

16

18 22

HO 26

H 7

H

6 1

O O

O

1.27 Amphidinolides

161

402 Amphidinolide E Type: Amphidinolides. C30H44O6 Amorph. solid. Source: Dinoflagellate Amphidinium sp., marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 2.0 μg/mL; KB, IC50 = 10 μg/mL). Ref: J. Kobayashi, et al, JOC, 1990, 55, 3421│T. Kubota, et al, JOC, 2002, 67, 1651│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) H

H O HO

OH

O

HO

O

403 Amphidinolide F Type: Amphidinolides. C35H52O9 Amorph. solid, [α]D30 = −57° (c = 0.1, CHCl3). Source: Dinoflagellate Amphidinium sp. from marine acoel flatworm Amphiscolops magniviridis. Pharm: Cytotoxic (L1210, IC50 = 1.5 μg/mL; KB, IC50 = 3.2 μg/mL). Ref: J. Kobayashi, et al, J. Antibiot., 1991, 44, 1259; 2008, 61(5), 271 (rev) O O

OH

H

H

O

OH O OH

H

O H

O

404 Amphidinolide G1 Type: Amphidinolides. C32H50O8 Amorph. powder, [α]D22 = −60.1° (c = 0.15, CHCl3). Source: Dinoflagellate Amphidinium sp., marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 0.0054 μg/mL; KB, IC50 = 0.0059 μg/mL; IC50 = 0.0046 μg/mL). Ref: J. Kobayashi, et al, JOC, 1991, 56, 5221; 2002, 67, 6585│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) OH

O OH

16

18 22

HO H 7

H

OH

6

26 1

O

O O

162

1 Polyketides

405 Amphidinolide G2 Type: Amphidinolides. C32H50O8 Oil, [α]D25 = −47° (c = 0.14, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.3 μg/mL; KB, IC50 = 0.8 μg/mL). Ref: J. Kobayashi, et al, JOC, 2002, 67, 6585 OH

O OH

16

18 22

HO H 7

H

OH

6

26 1

O

O O

406 Amphidinolide G3 Type: Amphidinolides. C32H52O8 Oil, [α]D25 = −89° (c = 0.14, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.72 μg/mL; KB, IC50 = 1.3 μg/mL). Ref: J. Kobayashi, et al, JOC, 2002, 67, 6585 OH

O OH

16

18 22

HO H 7

H

OH

6

26 1

O

O O

407 Amphidinolide H1 Amphidinolide H Type: Amphidinolides. C32H50O8 Needles (C6H6/hexane), mp 131–132 °C, [α]D18 = −32.3° (c = 0.2, CHCl3). Source: Dinoflagellate Amphidinium sp., marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 0.00048 μg/mL; KB, IC50 = 0.00052 μg/mL); cytotoxic (cultured tumor cells in vitro, IC50 = 0.00014–0.0045 g/mL, bind to actin subdomain 4 covalently) (Shimbo, 2005). Ref: J. Kobayashi, et al, JOC, 1991, 56, 5221; 2002, 67, 6585│Kobayashi, J. et al, Org. Lett., 2000, 2, 2805│T. Usui,et al, Chem. Biol. 2004, 11, 1269│K. Shimbo, et al, BoMC, 2005, 13, 5066│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)

1.27 Amphidinolides

OH

163

O OH

16

18 22

OH

HO H

H

26

6

7

1

O

O O

408 Amphidinolide H2 Type: Amphidinolides. C32H50O8 Oil, [α]D25 = −90° (c = 0.1, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.06 μg/mL; KB, IC50 = 0.06 μg/mL). Ref: J. Kobayashi, et al, JOC, 2002, 67, 6585│J. Kobayashi, et al, Pure Appl. Chem., 2003, 75, 337 OH

O OH

16

18 22

HO H

26

6

7

H

OH

1

O

O O

409 Amphidinolide H3 Type: Amphidinolides. C32H50O8 Oil, [α]D24 = −61° (c = 0.05, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.002 μg/mL; KB, IC50 = 0.022 μg/mL). Ref: J. Kobayashi, et al, JOC, 2002, 67, 6585│J. Kobayashi, et al, Pure Appl. Chem., 2003, 75, 337 OH

O OH

16

18 22

OH

HO H 7

H

26

6 1

O

O O

410 Amphidinolide H4 Type: Amphidinolides. C32H52O8 Oil, [α]D26 = −30° (c = 0.1, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.18 μg/mL; KB,

164

1 Polyketides

IC50 = 0.23 μg/mL). Ref: J. Kobayashi, et al, JOC, 2002, 67, 6585│J. Kobayashi, et al, Pure Appl. Chem., 2003, 75, 337 O

OH

OH 16

18 22

HO H 7

H

OH 26

6 1

O

O O

411 Amphidinolide H5 Type: Amphidinolides. C32H52O8 Oil, [α]D26 = −54° (c = 0.14, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.2 μg/mL; KB, IC50 = 0.6 μg/mL). Ref: J. Kobayashi, et al, JOC, 2002, 67, 6585│J. Kobayashi, et al, Pure Appl. Chem., 2003, 75, 337 O

OH

OH 16

18 22

HO H 7

H

OH 26

6 1

O

O

O

412 Amphidinolide J Type: Amphidinolides. C24H38O4 Oil, [α]D26 = +12° (c = 0.7, MeOH). Source: Dinoflagellate Amphidinium sp. from marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 2.7 μg/mL; KB, IC50 = 3.9 μg/mL). Ref: J. Kobayashi, et al, JOC, 1993, 58, 2645│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)

HO 9

OH H O O

1.27 Amphidinolides

165

413 Amphidinolide K Type: Amphidinolides. C27H40O5 Oil, [α]D21 = −71° (c = 0.05, MeOH). Source: Dinoflagellate Amphidinium sp. from marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 1.65 μg/mL; KB, IC50 = 2.9 μg/mL). Ref: M. Ishibashi, et al, JOC, 1993, 58, 6928│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O

H

O

OH

H

O O

414 Amphidinolide L Type: Amphidinolides. C32H50O8 Amorph. solid, [α]D27 = −50° (c = 0.1, C6H6). Source: Dinoflagellate Amphidinium sp. from marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 0.092 μg/mL; KB, IC50 = 0.1 μg/mL). Ref: M. Tsuda, et al, JOC, 1994, 59, 3734│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)

HO H

HO

HO

O OH O O

O

415 Amphidinolide M Type: Amphidinolides. C43H66O9 Colorless amorph. solid, [α]D26 = +4.5° (c = 1, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (mus L1210 leukemia cells, IC50 = 1.1 μg/mL; KB cells in vitro, IC50 = 0.44 μg/mL). Ref: J. Kobayashi, et al, JOC, 1994, 59, 4698 HO

O OH

O

OH O O

OH

O

166

1 Polyketides

416 Amphidinolide N Type: Amphidinolides. C33H52O11 Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.00005 μg/mL; KB, IC50 = 0.00006 μg/mL). Ref: M. Ishibashi, et al, J. Chem. Soc., Chem. Commun., 1994, 1455│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)│Y. Takahashi, et al, J. Antibiot., 2013, 66, 277 (structure revised) HO HO OH

O O

OH

OH O

O O

O

417 Amphidinolide O Type: Amphidinolides. C21H28O6 Needles, [α]D20 = +6.5° (c = 0.1, MeOH). Source: Dinoflagellate Amphidinium sp., marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 1.7 μg/mL; KB, IC50 = 3.6 μg/mL). Ref: M. Ishibashi, et al, JOC, 1995, 60, 6062│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O

O

H

O O

HO

H O

418 Amphidinolide P Type: Amphidinolides. C22H30O5 Amorph. solid, [α]D20 = +31° (c = 0.1, MeOH). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 1.6 μg/mL; KB, IC50 = 5.8 μg/mL). Ref: M. Ishibashi, et al, JOC, 1995, 60, 6062│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O

H

O O

HO

H O

1.27 Amphidinolides

167

419 Amphidinolide Q Type: Amphidinolides. C21H34O4 Oil, [α]D20 = +47° (c = 0.04, MeOH). Source: Dinoflagellate Amphidinium sp. Y-5. Pharm: Cytotoxic (L1210, IC50 = 6.4 μg/mL; KB, IC50 > 10 μg/mL). Ref: J. Kobayashi, et al, Tet. Lett., 1996, 37, 1449│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)│Y. Takahashi, et al, Org. Lett., 2008, 10, 3709

O O

HO O

420 Amphidinolide R Type: Amphidinolides. C34H38O4 Oil, [α]D20 = +23° (c = 0.5, MeOH). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 1.4 μg/mL; KB, IC50 = 0.67 μg/mL). Ref: M. Ishibashi, et al, Tetrahedron, 1997, 53, 7827│ J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)

HO OH

H O O

421 Amphidinolide S Type: Amphidinolides. C24H36O4 Oil, [α]D20 = +5° (c = 0.17, MeOH). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 4.0 μg/mL; KB, IC50 = 6.5 μg/mL). Ref: M. Ishibashi, et al, Tetrahedron, 1997, 53, 7827│ J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)

O 9

OH H O O

168

1 Polyketides

422 Amphidinolide T1 Amphidinolide T Type: Amphidinolides. C25H42O5 Colorless needles cryst. (methanol-water), mp 63–66 °C, [α]D24 = +18° (c = 0.3, CHCl3). Source: Dinoflagellate Amphidinium sp. Y-56 from marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 18 μg/mL; KB, IC50 = 35 μg/mL). Ref: J. Kobayashi, et al, JOC, 2001, 66, 134│ M. Tsuda, et al, JOC, 2000, 65, 1349│T. Kubota, et al, Tetrahedron, 2001, 57, 6175│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) OH O 12 14

O O O

423 Amphidinolide T2 Type: Amphidinolides. C26H44O6 Oil. Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 10 μg/mL; KB, IC50 = 11.5 μg/mL). Ref: J. Kobayashi, et al, JOC, 2001, 66, 134 O HO 12 14

S

OH O O O

424 Amphidinolide T3 Type: Amphidinolides. C25H42O5 Oil. Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 7.0 μg/mL; KB, IC50 = 10 μg/mL). Ref: J. Kobayashi, et al, JOC, 2001, 66, 134 O HO 12 14

O O O

1.27 Amphidinolides

169

425 Amphidinolide T4 Type: Amphidinolides. C25H42O5 Oil. Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 11 μg/mL; KB, IC50 = 18 μg/mL). Ref: J. Kobayashi, et al, JOC, 2001, 66, 134 O HO 12 14

O O O

426 Amphidinolide T5 Type: Amphidinolides. C25H42O5 Colorless oil. Source: Dinoflagellate Amphidinium sp., marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (mus L1210 IC50 = 15 μg/mL, hmn epidermoid carcinoma KB cells IC50 = 20 μg/mL). Ref: T. Kubota, et al, Tetrahedron, 2001, 57, 6175 O HO

12S

14

O O O

427 Amphidinolide U Type: Amphidinolides. C34H50O7 Source: Dinoflagellate Amphidinium sp.from marine acoel flatworm Amphiscolops sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 12 μg/mL; KB, IC50 > 20 μg/mL). Ref: M. Tsuda, et al, Tetrahedron, 1999, 55, 14565│ J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) H

O

O

H O H

HO O

O

OH

170

1 Polyketides

428 Amphidinolide V Type: Amphidinolides. C25H32O4 Oil, [α]D20 = −9.3° (c = 0.6, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210 cells, IC50 = 3.2 μg/mL; KB cells, IC50 = 7 μg/mL). Ref: T. Kubota, et al, Tet. Lett., 2000, 41, 713│A. Fürstner, et al, Angew. Chem., Int. Ed., 2007, 46, 5545

H

O

H

O

OH O

429 Amphidinolide W Type: Amphidinolides. C24H38O4 Oil. Source: Dinoflagellate Amphidinium sp. Y-42 from marine acoel flatworm Amphiscolops sp. Pharm: Cytotoxic (L1210, IC50 = 3.9 μg/mL; KB, IC50 > 10 μg/mL). Ref: K. Shimbo, et al, JOC, 2002, 67, 1020│A. K. Ghosh, et al, JOC, 2006, 71, 1085│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O

H O

O OH

430 Amphidinolide X Type: Amphidinolides. C26H40O6 Oil, [α]D17 = −12° (c = 1, CHCl3). Source: Dinoflagellate Amphidinium sp. Y-42. Pharm: Cytotoxic (L1210, IC50 = 0.6 μg/mL; KB, IC50 = 7.5 μg/mL). Ref: M. Tsuda, et al, JOC, 2003, 68, 5339│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev) O O

O O

O

O

431 Amphidinolide Y Type: Amphidinolides. C26H42O6 Oil, [α]D17 = −33° (c = 1, CHCl3). Source: Dinoflagellate Amphidinium sp. Pharm: Cytotoxic (L1210, IC50 = 0.8 μg/mL; KB, IC50 = 8.0 μg/mL). Ref: M. Tsuda, et al, JOC, 2003, 68, 9109│J. Kobayashi, et al, J. Antibiot., 2008, 61(5), 271 (rev)

1.28 Aplyronines

171

OH H

O

O H

HO O O

1.28 Aplyronines 432 Aplyronine A Aplyronine C O7-(2-dimethylamino-3-methoxypropanoyl) Type: Aplyronines. C59H101N3O14 [α]D28 = +32° (c = 0.26, MeOH). Source: Sea hare Aplysia kurodai (Japan waters). Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 0.48 ng/mL); antineoplastic (in vivo schedule ip days 1–5, Aplyronine A was dissolved in 0.08 mg/mL DMSO and then diluted with NaCl physiological solution: P388 leukemia, dose = 0.08 mg/(kg·day), 0.04 mg/(kg·day), 0.02mg/(kg·day), survival time test/control 545%, 418%, 157%, number of survivors after 60 days = 4/6, 2/6, 0/6; colon C26 carcinoma, dose = 0.08 mg/(kg·day), 0.04 mg/(kg·day), 0.02mg/(kg·day), survival time test/ control 255%, 248%, 159%, number of survivors after 60 days = 0/6, 1/6, 1/6; Lewis lung carcinoma, dose = 0.08 mg/(kg·day), 0.04 mg/(kg·day), 0.02mg/(kg·day), survival time test/control 86%, 556%, 555%, number of survivors after 60 days = 0/6, 6/6, 4/6; B16 melanoma, dose = 0.08 mg/(kg·day), 0.04 mg/(kg·day), 0.02mg/ (kg·day), survival time test/control 43%, 201%, 185%, number of survivors after 60 days = 0/6, 0/6, 0/6; Ehrlich carcinoma, dose = 0.08 mg/(kg·day), 0.04 mg/ (kg·day), 0.02mg/(kg·day), survival time test/control 80%, 398%, 220%, number of survivors after 60 days = 0/6, 2/6, 1/6); interaction with actin (1, to form 1:1 complex with monomer G-actin, 2, inhibited polymerization of G-actin to polymer fibrous Factin, 3, severed depolymerized F-actin to G-actin). Ref: M. Ojika, et al, Tet. Lett., 1993, 34, 8501│ M. Ojika, et al, Tet. Lett., 1993, 34, 8505│K. Yamada, et al, JACS., 1993, 115, 11020│ M. Ojika, et al, JACS., 1994, 116, 7441│ M. Ojika, et al, Tetrahedron, 2007, 63, 3138│K. Yamada, et al, NPR, 2009, 26, 27 O OH 9

O

N O

O N

7

O OH

O 22

O

O

O

38

O

O

O

N

172

1 Polyketides

433 Aplyronine B Aplyronine C O9-(2-dimethylamino-3-methoxypropanoyl) Type: Aplyronines. C59H101N3O14 [α]D27 = +3.7° (c = 0.19, MeOH). Source: Sea hare Aplysia kurodai. Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 3.11 ng/mL); antineoplastic. Ref: K. Yamada, et al, JACS, 1993, 115, 11 020│ M. Ojika, et al, Tet. Lett., 1993, 34, 8501│ M. Ojika, et al, Tet. Lett., 1993, 34, 8505│K. Suenaga, et al, Tet. Lett., 1995, 36, 5053│ M. Ojika, et al, Tetrahedron, 2007, 63, 3138│K. Yamada, et al, NPR, 2009, 26, 27 O O

N OH

O

O N

9

7

O OH

O

O

O

38

O

N

O

O

22

O

434 Aplyronine C Type: Aplyronines. C53H90N2O12 [α]D27 = +18° (c = 0.017, MeOH). Source: Sea hare Aplysia kurodai. Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 21.2 ng/mL); antineoplastic. Ref: K. Yamada, et al, JACS, 1993, 115, 11 020│ M. Ojika, et al, Tet. Lett., 1993, 34, 8501; 8505│K. Suenaga, et al, Tet. Lett., 1995, 36, 5053│ M. Ojika, et al, Tetrahedron, 2007, 63, 3138│K. Yamada, et al, NPR, 2009, 26, 27 OH

O

OH

N 9

7

O OH

O

O

O

38

O

O

N

O

22

O

435 Aplyronine D Type: Aplyronines. C58H99N3O14 White powder, [α]D28 = +14° (c = 0.09, MeOH). Source: Sea hare Aplysia kurodai (Mie Prefecture, Japan). Pharm: Cytotoxic (HeLaS3 cells, IC50 = 0.075 nmol/L). Ref: M. Ojika, et al, Tetrahedron, 2007, 63, 3138│ K. Yamada, et al, NPR, 2009, 26, 27 (rev)│ M. Ojika,et al, Tetrahedron, 2012, 68, 982 O O OH

O O

N

O O O

O

O O O

OH

N

O

N

1.28 Aplyronines

173

436 Aplyronine E Type: Aplyronines. C60H103N3O14 White powder, [α]D28 = +23° (c = 0.19, MeOH). Source: Sea hare Aplysia kurodai (Mie Prefecture, Japan). Pharm: Cytotoxic (HeLaS3 cells, IC50 = 0.18 nmol/L). Ref: M. Ojika, et al, Tetrahedron, 2007, 63, 3138│ K. Yamada, et al, NPR, 2009, 26, 27 (rev)│ M. Ojika,et al, Tetrahedron, 2012, 68, 982 O O

O

OH

O

N

O O O

O O O

OH

O

N

N

O

437 Aplyronine F Type: Aplyronines. C58H99N3O14 White powder, [α]D28 = +24° (c = 0.05, MeOH). Source: Sea hare Aplysia kurodai (Mie Prefecture, Japan). Pharm: Cytotoxic (HeLaS3 cells, IC50 = 0.19 nmol/L). Ref: M. Ojika, et al, Tetrahedron, 2007, 63, 3138│ K. Yamada, et al, NPR, 2009, 26, 27 (rev)│ M. Ojika,et al, Tetrahedron, 2012, 68, 982 O O

O

OH

O

N

O O O

O O O

OH

O

N

NH

O

438 Aplyronine G Type: Aplyronines. C58H99N3O14 White powder, [α]D28 = +28° (c = 0.13, MeOH). Source: Sea hare Aplysia kurodai (Mie Prefecture, Japan). Pharm: Cytotoxic (HeLaS3 cells, IC50 = 0.12 nmol/L). Ref: M. Ojika, et al, Tetrahedron, 2007, 63, 3138│ K. Yamada, et al, NPR, 2009, 26, 27 (rev)│ M. Ojika,et al, Tetrahedron, 2012, 68, 982 O OH 9

O

H N O

O N

7

O OH

O 22

O

O

O

38

O

O

O

N

174

1 Polyketides

439 Aplyronine H Type: Aplyronines. C58H99N3O14 White powder, [α]D28 = 0° (c = 0.05, MeOH). Source: Sea hare Aplysia kurodai (Mie Prefecture, Japan). Pharm: Cytotoxic (HeLaS3 cells, IC50 = 9.8 nmol/L). Ref: M. Ojika, et al, Tetrahedron, 2007, 63, 3138│ K. Yamada, et al, NPR, 2009, 26, 27 (rev)│ M. Ojika,et al, Tetrahedron, 2012, 68, 982 O O

H N OH

O

O O O O

O O O

OH

O

N

N

O

1.29 Lasonolides 440 Lasonolide A Type: Lasonolides. C41H60O9 Pale orange solid, [α]D10 = +24.2° (c = 0.20, CHCl3). Source: Sponges Forecpia sp. (Caribbean Sea), Acarnus sp., Hemitedania sp., Tedania sp. and Lissodendoryx sp. Pharm: PKC inhibitor (IC50 = 27 nmol/L, to inhibit the phorbol ester-stimulated adherence of EL-4 and IL-2, mouse thymoma cells within 30 min); signal transduction agent; cell adhesion inhibitor; cytotoxic (hmn lung carcinoma A549, IC50 = 0.0086 μmol/L; hmn pancreatic carcinoma PANC1, IC50 = 0.089 μmol/L; hmn breast cancer cell line NCI-ADR-Res (formerly MCF7/ADR), IC50 = 0.49 μmol/L). Ref: P. A. Horton, et al, JACS, 1994, 116, 6015│H. Y. Song, et al, JOC, 2003, 68, 8080│A. E. Wright, et al, JNP, 2004, 67, 1351│R. A. Isbrucker,et al, J. Pharmacol. Exp. Ther. 2009, 331, 733│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH O 28

O

O

31

OH O

O

O OH

441 Lasonolide C Type: Lasonolides. C41H60O10 Powder, [α]D20 = −9.8° (c = 0.32, CHCl3). Source: Sponge Forcepia sp. Pharm: Cytotoxic (hmn lung carcinoma A549, IC50 = 0.13 μmol/L;

1.29 Lasonolides

175

hmn pancreatic carcinoma PANC1, IC50 = 0.38 μmol/L; hmn breast cancer cell line NCI-ADR-Res (formerly MCF7/ADR), IC50 = 1.12 μmol/L). Ref: A. E. Wright, et al, JNP, 2004, 67, 1351 OH O 28

O

O OH

31

O

O

OH

OH

O

442 Lasonolide D Type: Lasonolides. C32H46O7 Oil, [α]D20 = −5.3° (c = 0.34, MeOH/CHCl3). Source: Sponge Forcepia sp. Pharm: Cytotoxic (hmn lung carcinoma A549, IC50 = 4.50 μmol/L; hmn pancreatic carcinoma PANC1, IC50 = 4.89 μmol/L; hmn breast cancer cell line NCI-ADRRes (formerly MCF7/ADR), IC50 > 9 μmol/L). Ref: A. E. Wright, et al, JNP, 2004, 67, 1351 HO

28

O

31

O

OH

O OH

O

443 Lasonolide E Type: Lasonolides. C35H50O9 Oil, [α]D20 = −18° (c = 0.3, MeOH/CHCl3). Source: Sponge Forcepia sp. Pharm: Cytotoxic (hmn lung carcinoma A549, IC50 = 0.31 μmol/L; hmn pancreatic carcinoma PANC1, IC50 = 0.57 μmol/L; hmn breast cancer cell line NCI-ADR-Res (formerly MCF7/ADR), IC50 > 8 μmol/L). Ref: A. E. Wright, et al, JNP, 2004, 67, 1351 OH O 28

O

O

31

OH O

O

O OH

176

1 Polyketides

444 Lasonolide F Type: Lasonolides. C33H46O9 Oil, [α]D20 = −23.5° (c = 0.23, MeOH). Source: Sponge Forcepia sp. Pharm: Cytotoxic (hmn lung carcinoma A549, IC50 > 9 μmol/L; hmn pancreatic carcinoma PANC1, IC50 = 15.6 μmol/L; hmn breast cancer cell line NCIADR-Res (formerly MCF7/ADR), IC50 > 9 μmol/L). Ref: A. E. Wright, et al, JNP, 2004, 67, 1351 OH O 28

O

OH

31

OH

O

O

OH

O

445 Lasonolide G Type: Lasonolides. C53H82O11 Source: Sponge Forcepia sp. Pharm: Cytotoxic (hmn lung carcinoma A549, IC50 > 6 μmol/L; hmn pancreatic carcinoma PANC1, IC50 > 6 μmol/L; hmn breast cancer cell line NCI-ADR-Res (formerly MCF7/ADR), IC50 > 6 μmol/L). Ref: A. E. Wright, et al, JNP, 2004, 67, 1351 OH O 28

O

O OH O

31

O

O O

O OH

1.30 Pectenotoxins 446 Pectenotoxin 1 PTX1 Type: Pectenotoxins. C47H70O15 Cryst. (MeCN aq), mp 208–209 °C, [α]D20 = +17.1° (c = 0.41, MeOH). Source: An unidentified shellfish. Pharm: Ichthyotoxin (component toxin of shellfish poisoning); cytotoxic. Ref: T. Yasumoto, et al, Tetrahedron, 1985, 41, 1019

1.30 Pectenotoxins

177

O H

O

H

O

47

OH OH 38 36

O

H

O

OH O

H O

H

O

O

O

33

H

11 7

O

OH

32

43

H

447 Pectenotoxin 2 PTX2 Type: Pectenotoxins. C47H70O14 Amorph., [α]D20 = +16.2° (c = 0.105, MeOH). Source: Sponges Poecillastra sp. and Jaspis sp., dinoflagellates Dinophysis acuminata and Dinophysis fortii. Pharm: Shellfish toxin; ichthyotoxin; hepatotoxin; nephrotoxin; cytotoxic (KB cells). Ref: T. Yasumoto, et al, Tetrahedron, 1985, 41, 1019│ J. H. Jung, et al, JNP, 1995, 58, 1722│T. Suzuki, et al, Toxicon, 2001, 39, 507 O H

O

H

O

47

OH 38 36

H

O

O

O

OH

H

OH

H

O

O

O

33

H 11

7

O

O

43

32

H

448 Pectenotoxin 3 PTX3 Type: Pectenotoxins. C47H68O15 Amorph., mp 159–160 °C, [α]D20 = +2.22° (c = 0.135, MeOH). Source: Dinoflagellates Dinophysis acuminata and Dinophysis fortii. Pharm: Shellfish toxin; ichthyotoxin. Ref: K. Sasaki, et al, JOC, 1998, 63, 2475 O H

O

H

O

O

33 47

OH OH 38 36

O

H

H O

H

11 7

H

O

O OH

O

O

32

H

O

O 43

449 Pectenotoxin 4 PTX4 Type: Pectenotoxins. C47H70O15 Solid, [α]D20 = +2.07° (c = 0.193, MeOH). Source: Dinoflagellate Dinophysis acuminata. Pharm: Shellfish toxin; ichthyotoxin. Ref: K. Sasaki, et al, JOC, 1998, 63, 2475

178

1 Polyketides

O H

O

H

O

47

H

O

O

O

OH

H

OH

38 36

H

O

O

O

33

OH

H 11

7

O

O

OH

32

43

H

450 Pectenotoxin 6 PTX6 Type: Pectenotoxins. C47H68O16 [α]D20 = +8.80° (c = 0.11, MeOH), [α]D20 = +37.1° (c = 0.15, CHCl3). Source: Dinoflagellate Dinophysis sp. Pharm: Shellfish toxin; phycotoxin. Ref: J. S. Lee, et al, Bioact. Mol., 1989, 10, 327 O H

O

H

O

47

38 36

H

O

O

O

OH

H

OH

H

O

O

O

33

OH

H 11

7

O

O

43

O

32

H

OH

451 Pectenotoxin 7 PTX7 Type: Pectenotoxins. C47H68O16 [α]D20 = +11.5° (c = 0.131, MeOH). Source: Dinoflagellate Dinophysis sp. Pharm: Phycotoxin; LD (mus ip) = 770 μg/kg. Ref: K. Sasaki, et al, JOC, 1998, 63, 2475 O H

O

H

O

47

38 36

O

H

O

OH

H O

H

O

O

O

33

OH OH

H

11 7

O

O

43

OH

32

H

O

452 Pectenotoxin 11 PTX11 Type: Pectenotoxins. C47H70O15 Source: Dinoflagellate Dinophysis acuta. Pharm: Shellfish toxin. Ref: T. Suzuki, et al, Chem. Res. Toxicol., 2006, 19, 310 O H

O

H

O

HO 47

OH

34S

33

OH

38 36

O

O

H 11

7

OH

O

O H

H

O

O

O H

O

43

1.30 Pectenotoxins

179

453 (36R)-Pectenotoxin 12 36-αOH-PTX12 Type: Pectenotoxins. C47H68O14 Source: Dinoflagellates Dinophysis acuminata and Dinophysis norvegica. Pharm: Shellfish toxin. Ref: C. O. Miles, et al, Chem. Res. Toxicol., 2004, 17, 1423 O H

O

H

O

O

33

OH

47

38 36

H

O

O

H

O

O

O

OH

H

OH

H 11

7

O

O

43

32

H

454 (36S)-Pectenotoxin 12 36-βOH-PTX12 Type: Pectenotoxins. C47H68O14 Source: Dinoflagellates Dinophysis acuminata and Dinophysis norvegica. Pharm: Shellfish toxin. Ref: C. O. Miles, et al, Chem. Res. Toxicol., 2004, 17, 1423 O H

O

H

O

O

33

OH

47

38 36

O

H

O

H

O

O

O

OH

H

OH

H 11

7

O

O

43

32

H

455 Poecillastrin A NSC 726108 Type: Pectenotoxins. C79H131N3O20 [α]D27 = −8.3° (c = 0.056, MeOH). Source: Sponge Poecillastra sp. Pharm: Cytotoxic (four different hmn tumor cell lines and two murine mast cell lines, Range of EC50 from < 25 nmol/L to > 10000 nmol/L, which were comparable to those observed with Chondropsins). Ref: A. Rashid, et al, Org. Lett., 2002, 4, 3293│E. J. J. Bowman, Biol. Chem., 2003, 278, 44147 H N OH

O

OH

OH 53

OH

O O HN

O O

OH

OH

OH

40

41

O

OH

H N

O 1

O HO

OH O

OH

180

1 Polyketides

456 Poecillastrin B Type: Pectenotoxins. C79H131N3O20 Gum, [α]D25 = +56° (c = 0.02, MeOH). Source: Sponge Poecillastra sp. Pharm: Cytotoxic (mixture with poecillastrin C, hmn melanoma cell line LOX, IC50 < 1 μg/mL). Ref: E. J. J. Bowman, Biol. Chem., 2003, 278, 44147│K. Takada, et al, JNP, 2007, 70, 428

H N OH

O

OH

OH 53

OH

O O HN 41

O

OH

OH

OH

OH

O

H N

O

O

1

O HO

OH

OH O

457 Poecillastrin C Type: Pectenotoxins. C78H129N3O20 Gum, [α]D25 = +31° (c = 0.02, MeOH). Source: Sponges Jaspis serpentina and Poecillastra sp. Pharm: Cytotoxic (mixture with Poecillastrin B, hmn melanoma cell line LOX, IC50 < 1 μg/mL). Ref: E. J. J. Bowman, Biol. Chem., 2003, 278, 44147│K. Takada, et al, JNP, 2007, 70, 428│D. Takemoto, et al, Biosci., Biotechnol., Biochem., 2007, 71, 2697

H N OH

O

OH

OH

53

OH

O O HN 41

O

OH

OH

O

OH

OH

O

H N 1

O HO

OH

O OH

O

1.31 Sphinxolides 458 Reidispongiolide A Type: Sphinxolides. C54H87NO13 [α]D = −4.8°. Source: Lithistid sponge Reidispongia coerulea (off New Caledonia). Pharm: Cytotoxic (NSCLC-N6, IC50 = 0.07 μg/mL,

1.31 Sphinxolides

181

P388/Dox, IC50 = 0.01 μg/mL, P388, IC50 = 0.16 μg/mL, KB, IC50 = 0.10 μg/mL, HT29, IC50 = 0.04 μg/mL); cytotoxic (actin-binding activity; disrupts actin cytoskeleton). Ref: M. V. D’Auria, et al, Tetrahedron, 1994, 50, 4829│I. Paterson, et al, Chem. Asian J., 2008, 3, 367│A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) O

O

O O

O 8

H

10

O

H

O

O O

O

O

N

19

O

H

O

459 Reidispongiolide B Type: Sphinxolides. C53H85NO13 [α]D = +3.5°. Source: Lithistid sponge Reidispongia coerulea (off New Caledonia). Pharm: Cytotoxic (NSCLC-N6, IC50 = 0.05 μg/mL, P388/Dox, IC50 = 0.02 μg/mL, P388, IC50 = 0.06 μg/mL, KB, IC50 = 0.06 μg/mL, HT29, IC50 = 0.04 μg/mL); disrupts actin cytoskeleton. Ref: M. V. D’Auria, et al, Tetrahedron, 1994, 50, 4829│A. E. Wright, Current Opinion in Biotechnology, 2010, 21, 801 O

O

O O

O 8

H

10

O

H

O

O O

O

O 19

O

OH

N H

460 Reidispongiolide C Type: Sphinxolides. C52H84O14 Amorph. powder, [α]D20 = +9.0° (c = 0.006, CHCl3). Source: Lithistid sponge Reidispongia coerulea (New Caledonia). Pharm: Cytotoxic (NC1’s screening assay, mean Log10 IC50 (mol/L) = −6.5). Ref: S. Carbonclli, et al, Tetrahedron, 1999, 55, 14665

182

1 Polyketides

O

O

O

O O

8

10

O

O

H

H

O O

O

O

OH

19

O

O

461 Sphinxolide A Type: Sphinxolides. C54H87NO15 Microcryst. powder (EtOAc), mp 90–92 °C, [α]D25 = −10.5° (c = 0.15, MeOH). Source: Lithistid sponge Neosiphonia superstes, an unidentified marine nudibranch. Pharm: Antineoplastic; apoptosis inducer; disrupts actin cytoskeleton. Ref: G. Guella, et al, Helv. Chim. Acta, 1989, 72, 237│ M. V. D’Auria, et al, Tetrahedron, 1993, 49, 8657; 10439│A. E. Wright, Current Opinion in Biotechnology, 2010, 21, 801 O

O

O O

O

O 8

H OH 10

O

H

O

O O

O

O

N

19

O

H

OH

462 Sphinxolide B Type: Sphinxolides. C53H85NO14 [α]D = +2.8° (MeOH). Source: Lithistid sponge Neosiphonia superstes. Pharm: Antineoplastic; disrupts actin cytoskeleton. Ref: M. V. D’Auria, et al, Tetrahedron, 1993, 49, 8657; 10439│A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801 O

O

O O

O 8

H OH 10

O

H

O

O O

O

O 19

O

OH

N H

1.31 Sphinxolides

183

463 Sphinxolide C Type: Sphinxolides. C55H89NO15 [α]D = −11.8° (MeOH). Source: Lithistid sponge Neosiphonia superstes. Pharm: Antineoplastic; apoptosis inducer; disrupts actin cytoskeleton. Ref: M. V. D’Auria, et al, Tetrahedron, 1993, 49, 8657; 10439│ A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801 O

O

O O

O

O 8

H OH 10

O

H

O

O O

O

O

N

19

O

H

O

464 Sphinxolide D Type: Sphinxolides. C54H87NO14 [α]D = −3.2° (MeOH). Source: Lithistid sponges Neosiphonia superstes and Reidispongia coerulea. Pharm: Antineoplastic; apoptosis inducer; disrupts actin cytoskeleton. Ref: M. V. D’Auria, et al, Tetrahedron, 1993, 49, 8657; 10439│A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801 O

O

O O

O 8

H 10

O

O

OH O H

O

O

O 19

O

O

N H

465 Sphinxolide E Type: Sphinxolides. C55H89NO16 Amorph. powder, [α]D20 = +2.9° (c = 0.004, CHCl3). Source: Lithistid sponge Neosiphonia superstes. Pharm: Cytotoxic (NC1’s screening assay, mean Log10 IC50 (mol/L) = −8.1); disrupts actin cytoskeleton. Ref: S. Carbonelli, et al, Tetrahedron, 1999, 55, 14665│A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801

184

1 Polyketides

O

O

O

O

O O

O

8

H OH 10

O

H

O

O O

O

O

N

19

O

H

O

466 Sphinxolide F Type: Sphinxolides. C52H84O16 Amorph. powder, [α]D20 = +24.3° (c = 0.001, CHCl3). Source: Lithistid sponge Neosiphonia superstes (New Caledonia). Pharm: Cytotoxic (NC1’s screening assay, mean Log10 IC50 (mol/L) = −7.2). Ref: S. Carbonclli, et al, Tetrahedron, 1999, 55, 14665

O

O

O

O

O

O 8

10

O

O

H OH O H

O

O

O

OH

19

O

OH

467 Sphinxolide G Type: Sphinxolides. C52H84O15 Amorph. powder, [α]D20 = +8.0° (c = 0.004, CHCl3). Source: Lithistid sponge Neosiphonia superstes (New Caledonia). Pharm: Cytotoxic (NC1’s screening assay, mean Log10 IC50 (mol/L) = −6.2). Ref: S. Carbonclli, et al, Tetrahedron, 1999, 55, 14665

O

O

O

O O

8

10

O

O

H OH O H

O

O

O 19

O

O

OH

1.32 Swinholides

185

1.32 Swinholides 468 Ankaraholide A 16,16′-Didemethyl-swinholide A 7,7′-bis-O-(2,3-di-O-methyl-β-L-lyxopyranoside) Type: Swinholides. C90H152O28 Yellowish oil, [α]D25 = −47° (c = 0.12, CHCl3). Source: Cyanobacterium Geitlerinema sp. Pharm: Cytotoxic (MDA-MB-435 breast carcinoma, IC50 = 8.9 nmol/L; NCI-H460 lung tumor, IC50 = 119 nmol/L; hmn neuro-2a, IC50 = 262 nmol/L); Anticancer-Cell-Effect (model: rat aorta A-10 cells, mechanism: 60 nmol/L, loss of filamentous F-actin). Ref: E. H. Andrianasolo, et al, Org. Lett. 2005, 7, 1375│ M. Costa, et al, Mar. Drugs, 2012, 10, 2181 (rev) O

O OH

OH O

O

O H

7

O

O

O H

O 7'

16

O

H OH

O

OH O

16'

H

OH beta-L-xylo O

O HO

O

OH

OH

O O O

O

beta-L-xylo

26 29

O

469 Ankaraholide B 16-Demethyl-swinholide A 7,7′-bis-O-(2,3-di-O-methyl-β-L-lyxopyranoside) Type: Swinholides. C91H154O28 Yellowish oil, [α]D25 = −37° (c = 0.07, CHCl3). Source: Cyanobacterium Geitlerinema sp. (Nosy Mitso-ankaraha I., Madagascarr). Pharm: Cytotoxic (30 nmol/L and 60 nmol/L, causes complete loss of filamentous actin with disruption of actin cytoskeleton). Ref: E. H. Andrianasolo, et al, Org. Lett., 2005, 7, 1375│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

186

1 Polyketides

O

31'

27'

O OH

O

23'

OH

beta-L-Lyxose

OH O

OH

O

O

19'

17'

7

1

O

H O

H

O O

21'

O H

O 1'

7'

O

19

17

OH

OH

16

21

OH H

O HO

O

23

O

O 31

27

O O beta-L-Lyxose O

470 Bistheonellide A Misakinolide A Type: Swinholides. C74H128O20 Oil, [α]D20 = −21.4° (c = 5.6, CHCl3). Source: Lithistid sponge Theonella sp. Pharm: Cytotoxic (tumor cell lines, nanomolar); disrupts actin cytoskeleton (inhibits polymerization of G-actin and depolymerizes F-actin in concentration-dependent fashion, important biochemical probe to study actin dynamics). Ref: R. Sakai, et al, Chem. Lett., 1986, 1499│Y. Kato, et al, Tet. Lett., 1987, 28, 6225│J. Tanaka, et al, CPB, 1990, 38, 2967│T. Higa, et al, ACS Symp. Ser., 2000, 745, 12│A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801 O

O OH

OH O

OH

OH

O

O

O

H

O

O H

H

O OH O

O

O HO

OH

OH

H

1.32 Swinholides

187

471 Bistheonellide B Type: Swinholides. C73H126O20 Source: Lithistid sponge Theonella sp. Pharm: Cytotoxic. Ref: R. Sakai, et al, Chem. Lett., 1986, 1499│Y. Kato, et al, Tet. Lett., 1987, 28, 6225│ J. Tanaka, et al, CPB, 1990, 38, 2967│T. Higa, et al, ACS Symp. Ser., 2000, 745, 12 O

O HO

OH O

OH

OH H

O

14'

O

O

H

H

O

O

O

H

OH O

O HO

OH OH

H

O

472 Hurghadolide A Type: Swinholides. C76H130O20 Light yellow solid, [α]D25 = −29.4° (c = 0.08, MeOH). Source: Lithistid sponge Theonella swinhoei (Hurghada, Red Sea coast, Egypt). Pharm: Cytotoxic (HCT116, in vitro, IC50 = 5.6 nmol/L, very potent); cytotoxic (disruption of actin cytoskeleton, 70 nmol/L); antifungal (yeast Candida albicans, MIC = 31.3 μg/mL). Ref: D. T. A. Youssef, et al, JNP, 2006, 69, 154│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) O

O OH

OH O

OH

OH

O

O

O

H

O

O H

O OH O

O

O HO

H

OH

OH

H

188

1 Polyketides

473 Isoswinholide A Type: Swinholides. C78H132O20 Amorph. powder + 1H2O, [α]D29 = −42° (c = 0.51, CHCl3). Source: Lithistid sponge Theonella swinhoei (Red Sea). Pharm: Cytotoxic (KB cell line, IC50 = 1.1 μg/mL). Ref: J. Tanaka, et al, CPB, 1990, 38, 2960; 2967 O

27'

O

31'

23'

OH OH

O 21'

O O

7

1

OH

O

OH

HO

O

HO

O

HO

OH O O O

O

474 Swinholide A Type: Swinholides. C78H132O20 Microcryst. + H2O (EtOAc), mp 102 °C, [α]D24 = +16° (c = 1.3, CHCl3). Source: Lithistid sponge Theonella swinhoei (Red Sea), cyanobacterium Symploca cf. sp. (Fiji). Pharm: Cytotoxic (KB nasopharyngeal epidermoid carcinoma cell line in vitro, IC50 = 1.2 nmol/L, very potent); cytotoxic (L1210 cells, IC50 = 0.03 μg/mL; KB cells, IC50 = 0.04 μg/mL); antifungal; disrupts actin cytoskeleton (to rapidly sever F-actin, important biochemical probe to study actin dynamics). Ref: S. Carmely, et al, Tet. Lett., 1985, 26, 511│S. Carmely, et al, Magn. Reson. Chem., 1986, 24, 343│ M. Kobayashi, et al, Tet. Lett., 1989, 30, 2963│I. Kitagawa, et al, JACS, 1990, 112, 3710│ M. Doi, et al, JOC, 1991, 56, 3629│I. Paterson, et al, JACS., 1994, 116, 9391│A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)│S. De Marino, et al, Mar. Drugs, 2011, 9, 1133

1.32 Swinholides

189

O

O

OH

OH O

OH

OH

O

16'

7

O

O

H O

H

O 7'

H

H

16

O

OH

O HO

OH

OH

O 26 29

O

475 Swinholide B Type: Swinholides. C77H130O20 Amorph. powder + 1H2O, [α]D22 = +2.5° (c = 6.1, CHCl3). Source: Lithistid sponges Theonella sp. and Theonella swinhoei (Red Sea). Pharm: Cytotoxic (KB cell line, IC50 = 0.041 μg/mL). Ref: M. Kobayashi, et al, CPB, 1990, 38, 2960; 2967 O

27'

O

31'

23'

OH OH

OH

OH

O

H

21' 16'

O

19'

17'

7

1

O

O

H O

O 1'

7'

O

19

17

OH

OH

21

H

O HO

OH

23

O 31

O

27

H

190

1 Polyketides

476 Swinholide C Type: Swinholides. C77H130O20 Amorph. powder + 2H2O, [α]D24 = +5.4° (c = 5.4, CHCl3). Source: Lithistid sponges Theonella sp.and Theonella swinhoei (Red Sea). Pharm: Cytotoxic (KB cell line, IC50 = 0.052 μg/mL). Ref: M. Kobayashi, et al, CPB, 1990, 38, 2960; 2967

OH

27'

O

31'

23'

OH

OH O

OH

OH

H

21'

O

19'

17'

1

7

O

H O

O O

1'

7'

O

19

17

OH

OH

H

21

H

O HO

OH

23

O 31

27

O

477 Swinholide H Type: Swinholides. C80H136O20 Solid, mp 90–91 °C, [α]D20 = −82° (c = 0.165, EtOH). Source: Sponge Lamellomorpha strongylata (yield = 8.5 × 10−3%ww, New Zealand). Pharm: Cytotoxic (NCI’s in vitro 60 cell line screening system, mean Log10 GI50 (mol/L) = −8.00 (Δ = 0.60, range = 1.49); mean Log10 TGI (mol/L) = −6.71 (Δ = 1.90, range = 4.00); mean Log10 LC50 (mol/L) = −5.60 (Δ = 1.81, range = 2.80)). Ref: E. J. Dumdei, et al, JOC, 1997, 62, 2636

1.32 Swinholides

191

O

O OH

OH

OH

O

O

O

O

O

O O

O

O O

HO

OH

OH

O

O

478 Swinholide I Type: Swinholides. C78H132O21 Light yellow solid, [α]D25 = −42.5° (c = 0.04, MeOH). Source: Lithistid sponge Theonella swinhoei (Hurghada, Red Sea coast, Egypt). Pharm: Cytotoxic (HCT116, in vitro, IC50 = 365 nmol/L, very potent); cytotoxic (disruption of actin cytoskeleton, 70 nmol/L); antifungal (yeast Candida albicans, MIC = 62.2 μg/mL). Ref: D. T. A. Youssef, et al, JNP, 2006, 69, 154│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) O

27'

O

23'

OH

31'

OH O

OH

OH

H

21'

O

19'

17'

1

7

O

H O

O O

1'

7'

O

19

17

OH

OH

21

H

O HO OH

OH O 31

O

27

23

H

192

1 Polyketides

479 Swinholide K Type: Swinholides. C78H132O21 Source: Lithistid sponge Theonella swinhoei (Bunaken Marine Park, Manado, Indonesia). Pharm: Cytotoxic (HepG2, significant potency). Ref: A. Sinisi, et al, Bioorg. Med. Chem., 2013, 21, 5332 O

O O

OH O

OH

OH

OH

O HO O

O

O

O

OH

OH

O

HO

HO O

O

1.33 Other Macrocyclic Polyketide Lactones 480 Acuminolide A Type: Other macrocyclic polyketide lactones. C48H64O19S Source: Dinofiagellate Dinophysis acuminata Pharm: Actomyosin ATPase stimulator (potent). Ref: B. S. Hwang, et al, Org. Lett., 2014, 16, 5362 OH O

OH OH

S

HO

O O

O O

HO H

O

O O

O

H O

O

OH

O OH

1.33 Other Macrocyclic Polyketide Lactones

193

481 Altohyrtin B Type: Other macrocyclic polyketide lactones. C63H95BrO21 Amorph. solid, [α]D = +45° (c = 0.2, MeOH). Source: Sponge Hyrtios altum (Okinawa). Pharm: Cytotoxic (KB, IC50 = 0.02 ng/mL). Ref: M. Kobayashi, et al, Tet. Lett., 1993, 34, 2795│ M. Kobayashi, et al, CPB, 1993, 41, 989│ M. Kobayashi, et al, Tet. Lett., 1994, 35, 1243 Br 50

OH O

O H

OH

HO HO

5

O

O

OH O

O

H

H O

O H

O OH

HO

O

H O H

15

H

O O O

482 Amphilactam A Type: Other macrocyclic polyketide lactones. C35H51NO7 Yellow oil, [α]D = +11.8° (c = 0.35, CHCl3). Source: Sponge Amphimedon sp. (Southern Australia). Pharm: Nematocide. Ref: S. P. B. Ovenden, et al, JOC, 1999, 64, 1140

O

O

O O

2

O

H N O

OH

483 Amphilactam B Type: Other macrocyclic polyketide lactones. C36H53NO7 Yellow oil, [α]D = +8.5° (c = 0.38, CHCl3). Source: Sponge Amphimedon sp. (Southern Australia). Pharm: Nematocide. Ref: S. P. B. Ovenden, et al, JOC, 1999, 64, 1140

194

1 Polyketides

O

O

O O

2

O

H N OH

O

484 Amphilactam C Type: Other macrocyclic polyketide lactones. C35H51NO7 Yellow oil, [α]D = +17.3° (c = 0.48, CHCl3). Source: Sponge Amphimedon sp. (Southern Australia). Pharm: Nematocide. Ref: S. P. B. Ovenden, et al, JOC, 1999, 64, 1140

O

O

O 2E

O

O

NH O

OH

485 Amphilactam D Type: Other macrocyclic polyketide lactones. C36H53NO7 Yellow oil, [α]D = +2.5° (c = 0.03, CHCl3). Source: Sponge Amphimedon sp. (Southern Australia). Pharm: Nematocide. Ref: S. P. B. Ovenden, et al, JOC, 1999, 64, 1140

O

O O

O 2E

O

NH O

OH

486 Antibiotic BK 223B Type: Other macrocyclic polyketide lactones. C32H38O15 [α]D22 = −5° (c = 0.8, MeOH). Source: Marine-derived fungus Hypoxylon oceanicum LL-15G256. Pharm: Antifungal. Ref: J. Breinholt, et al, J. Antibiot., 1993, 46, 1101│G. Schlingmann, et al, Tetrahedron, 2002, 58, 6825

1.33 Other Macrocyclic Polyketide Lactones

O

O OH

O

HO

O

O OH

195

O

O

O

OH

O O OH

487 Aplasmomycin A Aplasmomycin Type: Other macrocyclic polyketide lactones. C40H60BO141- Na salt: needles (MeOH), mp 283–285 °C (dec), [α]D22 = +225° (c = 1.24, CHCl3), ionophore. Source: Marine-derived streptomycete Streptomyces griseus. Pharm: Antibacterial (gram-positive bacteria); insecticide; acaricide. Ref: H. Nakamura, et al, J. Antibiot., 1977, 30, 714│K. Sato, et al, J. Antibiot., 1978, 31, 632 H

OH 9

O H

H

O H

O O

O

O

–

B O O

H

H 9'

O

O

O O

H

HO H

488 Aplasmomycin B Type: Other macrocyclic polyketide lactones. C42H62BO151- [α]D = +188° (MeOH) (Na salt). Source: Marine-derived streptomycete Streptomyces griseus. Pharm: Antibacterial (gram-positive bacteria). Ref: H. Nakamura, et al, J. Antibiot., 1977, 30, 714│K. Sato, et al, J. Antibiot., 1978, 31, 632

196

1 Polyketides

H

OH 9

O H O

H H

O O

O

O

–

B O O

H H

H 9'

O

O

O

O

O

O H

489 Aplasmomycin C Type: Other macrocyclic polyketide lactones. C44H64BO151- [α]D = +134° (MeOH) (Na salt). Source: Marine-derived streptomycete Streptomyces griseus. Pharm: Antibacterial (gram-positive bacteria). Ref: H. Nakamura, et al, J. Antibiot., 1977, 30, 714│K. Sato, et al, J. Antibiot., 1978, 31, 632 H

O 9

O H O

H

O O

O

O

B

–

O

H H

H

O

O

O

O

9'

O

H

O

O

O H

490 Arenolide Type: Other macrocyclic polyketide lactones. C25H42O6 Viscous oil, [α]D = +13.0° (c = 0.64, CHCl3). Source: Sponge Dysidea sp. (Palau, Oceania). Pharm: Cytotoxic (hmn colon carcinoma HCT116 cells, hmn ovarian carcinoma A2780 cells). Ref: Q. Lu, et al, JNP, 1998, 61, 1096

1.33 Other Macrocyclic Polyketide Lactones

197

O

HO O

OH

OH

OH

491 Belizeanolide Type: Other macrocyclic polyketide lactones. C81H132O20 Amorph. solid, [α]D25 = −9.2° (c = 0.001, MeOH). Source: Dinoflagellate Prorocentrum belizeanum. Pharm: Cytotoxic (A2780, GI50 = (3.28 ± 0.45)μmol/L; SW1573, GI50 = (3.23 ± 0.45)μmol/L; HBL100, GI50 = (3.23 ± 0.38)μmol/L; T47D, GI50 = (3.16 ± 0.40)μmol/L; WiDr, GI50 = (4.58 ± 0.40)μmol/L). Ref: J. G. Napolitano, et al, Angew. Chem., Int. Ed., 2009, 48, 796 HO

OH

O OH O

OH

HO

OH

O OH OH

OH

53

HO

O O O OH

OH

OH OH

492 Belizentrin Type: Other macrocyclic polyketide lactones. C49H75NO17 Source: Dinofiagellate Prorocentrum belizeanum Pharm: cell toxic (potent effects on neuronal network integrity in cerebellar cells, ultimately resulting in cell death). Ref: H. J. Domíınguez, et al, Org. Lett., 2014, 16, 4546

198

1 Polyketides

OH

O O

O

O

HO

OH

HO H N

OH HO

O

HO O O

HO

OH HO

493 Biselyngbyaside Type: Other macrocyclic polyketide lactones. C34H52O9 [α]D25 = −36° (c = 0.1, CHCl3). Source: Cyanobacterium Lyngbya sp. Pharm: Cytotoxic (SRB assay, human HeLa-S3 epithelial carcinoma, IC50 = 0.1 μg/mL; SNB78 central nervous system cancer; GI50 = 0.036 μmol/L; NCI-H522 lung cancer, GI50 = 0.067 μmol/L); cytotoxic (diseaseoriented panel of 39 hmn cancer cell lines (HCC panel), average GI50 = 0.60 μmol/L); cytotoxic (COMPARE negative, inhibits cancer cell proliferation with a novel mechanism). Ref: T. Yamori,et al, Cancer Res. 1999, 59, 4042│T. Teruya, et al, Org. Lett. 2009, 11, 2421

O

O

HO OO

O

O OH

OH

494 Biselyngbyaside B Type: Other macrocyclic polyketide lactones. C34H54O10 Source: Cyanobacterium Lyngbya sp. (sample 2, Tokunoshima I., Japan). Pharm: Cytotoxic (HeLa-S3 and HL60 cells, inhibits growth and induces apoptosis with increased cytosolic Ca2+ concentration in HeLa-S3 Cells). Ref: T. Teruya, et al, Org. Lett., 2009, 11, 2421│ M. Morita, et al, Tetrahedron, 2012, 68, 5984

1.33 Other Macrocyclic Polyketide Lactones

O

O

O

O

199

OH

HO

OH

O

OH O

495 Biselyngbyolide A Type: Other macrocyclic polyketide lactones. C27H42O5 Source: Cyanobacterium Lyngbya sp. (sample 1, Tokunoshima I., Japan). Pharm: Cytotoxic (HeLa-S3 and HL60 cells, potent apoptosis-inducer). Ref: M. Morita, et al, Chem. Lett., 2012, 41, 165

O

O

OH

O

OH

496 Borophycin Type: Other macrocyclic polyketide lactones. C44H68BO141- Cryst. (CH2Cl2/MeOH) (Na salt), [α]D = −23.7° (c = 1.4, CHCl3) (Na salt). Source: Cyanobacteria Nostoc linckia and Nostoc spongiaeformia. Pharm: Cytotoxic (potent). Ref: T. Hemscheidt, et al, JOC, 1994, 59, 3467

O O

O O OH O O

O

O B

O

HO

O O O

497 Brefeldin A Ascotoxin; Cyanein Type: Other macrocyclic polyketide lactones. C16H24O4 Prisms (MeOH/Et2O), mp 204–205 °C, [α]D22 = +96° (MeOH). Source: Marine-derived fungus Penicillium sp. PSU-F44 from gorgonian sea fan Annella sp. (Thailand), an unidentified fungus (soil sample, Chile, 1998), an unidentified fungus 0GOS1620. Pharm:

200

1 Polyketides

Cytotoxic (P388, GI50 = 0.23 μg/mL; OVCAR-3, GI50 = 0.041 μg/mL; NCI-H460, GI50 = 0.28 μg/mL; KM20L2, GI50 = 0.022 μg/mL; DU145, GI50 = 0.13 μg/mL; BXPC3, GI50 = 0.07 μg/mL; MCF7, GI50 = 0.047 μg/mL; SF268, GI50 = 0.21 μg/mL; SF295, GI50 = 0.38 μg/mL); antibacterial (MRSA SK1); antifungal (MG SH-MU-4, MIC = 64 μg/mL); fish toxin; anti-HIV; LD50 (mus, ipr) = 200 mg/kg. Ref: G. R. Pettit, et al, JNP 2008, 71, 438│K. Trisuwan, et al, CPB, 2009, 57, 1100 OH O

H

O OH H

498 Calcaride A Type: Other macrocyclic polyketide lactones. C33H40O14 Source: Marine fungus Calcarisporium sp. Pharm: Antibacterial (Staphylococcus epidermidis, MIC = 68.8 μg/mL; Xanthomonas campestris, MIC = 5.5 μg/mL). Ref: J. Silber, et al, Mar. Drugs, 2013, 11, 3309 O O

O

O

HO O

O

OH

O OH

O

O

O

O

499 Calcaride B Type: Other macrocyclic polyketide lactones. C33H40O15 Source: Marine fungus Calcarisporium sp. Pharm: Antibacterial (Staphylococcus epidermidis, MIC = 53.2 μg/mL; Xanthomonas campestris, MIC = 22.6 μg/mL). Ref: J. Silber, et al, Mar. Drugs, 2013, 11, 3309 O O

O

O

HO O

O

O OH

O O

OH

OH

O O

1.33 Other Macrocyclic Polyketide Lactones

201

500 Calcaride C Type: Other macrocyclic polyketide lactones. C33H40O15 Source: Marine fungus Calcarisporium sp. Pharm: Antibacterial (Staphylococcus epidermidis, MIC = 29.6 μg/mL; Xanthomonas campestris, MIC = 61.4 μg/mL). Ref: J. Silber, et al, Mar. Drugs, 2013, 11, 3309 O O

O

O

HO O

O

OH

O OH

O

O

O

O OH

501 Calcaride E Type: Other macrocyclic polyketide lactones. C33H42O15 Source: Marine fungus Calcarisporium sp. Pharm: Antibacterial (Staphylococcus epidermidis, MIC = 104.3 μg/mL; Xanthomonas campestris, MIC = 150 μg/mL). Ref: J. Silber, et al, Mar. Drugs, 2013, 11, 3309 O O O

HO O

O

OH

O OH

O O O

O

OH HO

502 Callipeltoside A Type: Other macrocyclic polyketide lactones. C35H48ClNO10 [α]D = −17.6° (c = 0.04, MeOH). Source: Lithistid sponge Callipelta sp. (off New Caledonia). Pharm: Cytotoxic (NSCLC-N6, IC50 = 16.6 μmol/L; P388, IC50 = 22.4 μmol/L; A2780, IC50 = 20.0 μmol/L); cell proliferation inhibitor. Ref: A. Zampella, et al, JACS, 1996, 118, 11085│B. M. Trost, et al, JACS, 2002, 124, 10396│C. K. Skepper, et al, JACS, 2007, 129, 4150│J. B. MacMillan, et al, JOC, 2008, 73, 3699│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

202

1 Polyketides

O

O H

OH

H

HN

O

O O O

O

O

O

H

Cl

503 Callipeltoside B Type: Other macrocyclic polyketide lactones. C35H50ClNO10 Source: Lithistid sponge Callipelta sp. (New Caledonia). Pharm: Cytotoxic (NSCLC-N6, IC50 = 15.1 μg/mL); cell proliferation inhibitor. Ref: A. Zampella, et al, Tetrahedron, 1997, 53, 3243│ J. Carpenter, et al, Angew. Chem., Int. Ed., 2008, 47, 3568 (Absolute config. Revised) OH H

O

N H

O

O

H

H O

OH O

O

O

O

H Cl

504 Callipeltoside C Type: Other macrocyclic polyketide lactones. C34H49ClO10 Source: Lithistid sponge Callipelta sp. (New Caledonia). Pharm: Cytotoxic (NSCLC-N6, IC50 = 30 μg/mL). Ref: A. Zampella, et al, Tetrahedron, 1997, 53, 3243│J. Carpenter, et al, Angew. Chem., Int. Ed., 2008, 47, 3568 (Absolute config. Revised)│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)│CRC Press, DNP on DVD, 2012, version 20.2

1.33 Other Macrocyclic Polyketide Lactones

203

OH OH

O

O

O

H

OH O

O

O

O

H Cl

505 Candidaspongiolide A Type: Other macrocyclic polyketide lactones. C34H52O14 Source: Sponge Candidaspongia sp. (Papua New Guinea). Pharm: Cytotoxic (Candidaspongiolide A/B mixture, A:B = 1.7:1, melanoma UACC-257, IC50 = (1.6 ± 0.5)nmol/L; melanoma LOX-IMVI, IC50 < 2.0 nmol/L; melanoma M14, IC50 = (7.5 ± 1.5)nmol/L; MCF7, IC50 < 2.0 nmol/L; NCI-H460, IC50 = (3.4 ± 0.2)nmol/L). Ref: E. L. Whitson, et al, Org. Lett., 2011, 13, 3518 O

OH O

O

OH

O O HO

O

O

OH

O OH

O

506 Candidaspongiolide B Type: Other macrocyclic polyketide lactones. C34H52O14 Source: Sponge Candidaspongia sp. (Papua New Guinea). Pharm: Cytotoxic (Candidaspongiolide A/B mixture, A:B = 1.7:1, melanoma UACC-257, IC50 = (1.6 ± 0.5)nmol/L; melanoma LOX-IMVI, IC50 < 2.0 nmol/L; melanoma M14, IC50 = (7.5 ± 1.5)nmol/L; MCF7, IC50 < 2.0 nmol/L; NCI-H460, IC50 = (3.4 ± 0.2)nmol/L). Ref: E. L. Whitson, et al, Org. Lett., 2011, 13, 3518

204

1 Polyketides

O

OH O

O

OH

O O HO

O

O

OH

O O

OH

507 Caribenolide I Type: Other macrocyclic polyketide lactones. C33H52O11 Microcryst. powder (2,2,4trimethylpentane/2-propanol), [α]D25 = +91° (c = 0.1, CH2Cl2). Source: Dinoflagellate Amphidinium sp. S1-36-5 (yield = 0.026%dw, St. Thomas, US Virgin Is.). Pharm: Cytotoxic (hmn colon tumor HCT116 cell line and its drug-resistant HCT116/VM46 cell line, IC50 = 0.001 μg/mL (= 1.6 nmol/L); control most potent dinoflagellate macrolide previously reported Amphidinolide B, HCT116, IC50 = 0.122 μg/mL); antineoplastic (in vivo, murine tumor P388, 0.03 mg/kg, T/C = 150%). Ref: I. Bauer, et al, JOC, 1995, 60, 1084 HO H

H

HO HO

O H

O

O O

OH

OH

O

O

508 Caylobolide A Type: Other macrocyclic polyketide lactones. C42H82O11 [α]D = −9.7° (c = 0.25, MeOH). Source: Cyanobacterium Lyngbya majuscula (Bahamas). Pharm: Cytotoxic (hmn HCT116 cell lines, IC50 = 9.9 μmol/L). Ref: J. B. MacMillan, et al, Org. Lett., 2002, 4, 1535│L. A. Salvador, et al, JNP 2010, 73, 1606 OH

OH

OH 13

42

O 1

7

40

O 36

33

OH

HO 21

HO

25

OH

OH

41

OH

1.33 Other Macrocyclic Polyketide Lactones

205

509 Caylobolide B Type: Other macrocyclic polyketide lactones. C42H80O11 Colorless amorph. solid, [α]D20 = −15° (c = 0.15, MeOH). Source: Cyanobacteria Phormidium spp. (breakwater at Fort Zachary Taylor State Park, Key West, Florida, June 24, 2008). Pharm: Cytotoxic (MTT assay, HT29 colorectal adenocarcinoma, IC50 = 4.5 μmol/L, HeLa cervical carcinoma, IC50 = 12.2 μmol/L). Ref: L. A. Salvador, et al, JNP 2010, 73, 1606 42

OH

OH

OH 13

O

40

O

1

7

36 33

OH

HO

OH

41

OH

OH

21

HO

25

510 Chondropsin A Type: Other macrocyclic polyketide lactones. C83H133N3O26 Powder, [α]D27 = +7.1° (c = 0.28, MeOH). Source: Sponges Ircinia ramosa (Australia), Chondropsis sp. and Psammoclemma sp. Pharm: Cytotoxic (NCIs 60-cell screen, mean-panel GI50 = 2.4 × 10−8 mol/L, range > 103 in relative sensitivities of individual cell lines; COMPARE-algorithm analyses revealed no significant correlation to any meangraph profiles contained in NCI’s standard agents database; different mechanism of tumor growth inhibition from that of conventional antitumor agents; it may be a new structural class for cancer therapeutics research). Ref: C. L. Cantrell, et al, JACS, 2000, 122, 8825│ M. A. Rashid, et al, Tet. Lett., 2001, 42, 1623 H N

O O

OH

O

O

OH

OH 73

HO

HO HN 32

O

OH

OH

OH HOOC

OH

O 67

OH

O O

H N O HO

O

1

O COOH

511 Chondropsin C Type: Other macrocyclic polyketide lactones. C81H131N3O23 Powder, [α]D = +2.7° (c = 0.3, MeOH). Source: Sponge Ircinia sp. (Philippines). Pharm: Cytotoxic (in vitro,

206

1 Polyketides

hmn melanoma LOX cell lines, IC50 = 0.8 ng/mL; hmn leukemia Molt4 cell lines, IC50 = 0.2 ng/mL). Ref: M. A. Rashid, et al, Tet. Lett., 2001, 42, 1623

73

O

O

OH

OH

OH

H N

HO HN

O

32 67

O

OH

OH

OH

OH

O

OH O

HOOC

O

H N

1

O

O HO

COOH

512 Chondropsin D Chondropsin B-32-O-(3-carboxy-3-hydroxypropanoyl)-(1→67)-Lactone Type: Other macrocyclic polyketide lactones. C83H133N3O26 Gum, [α]D27 = −5° (c = 0.06, MeOH). Source: Sponge Chondropsis sp. (depth of 20m, along shore of Bass I., Wollongong, Australia). Pharm: Cytotoxic (2-day in vitro assay, hmn melanoma LOX cell lines, IC50 = 10 ng/mL; hmn leukemia Molt4 cell lines, IC50 = 250 ng/mL). Ref: M. A. Rashid, et al, JNP, 2001, 64, 1341

H N

O

OH

OH

73

O

O

OH

O

OH

HO N H

32

HO

O

67

OH O

OH

OH

O

OH

O

O 1

HOOC

O

N H O

COOH OH

513 Dactylolide Type: Other macrocyclic polyketide lactones. C23H28O5 Amorph. solid, [α]D = +30° (c = 1, MeOH). Source: Sponge Dactylospongia sp. Pharm: Cytotoxic (3.2 μg/mL, L1210, InRt = 63%; SK-OV-3, InRt = 40%). Ref: A. Cutignano, et al, EurJOC, 2001, 775

1.33 Other Macrocyclic Polyketide Lactones

207

O

O O

O

O

514 7-Dehydrobrefeldin A 7-Oxobrefeldin A Type: Other macrocyclic polyketide lactones. C16H22O4 Source: Marine-derived fungus Penicillium sp. PSU-F44 from gorgonian sea fan Annella sp. (Thailand). Pharm: Antibacterial (MRSA SK1); phytotoxin. Ref: K. Trisuwan, et al, CPB, 2009, 57, 1100 OH O

H

O O H

515 19-O-DemethylscytophycinC Type: Other macrocyclic polyketide lactones. C44H73NO11 Amorph. solid. Source: Cyanobacteria Scytonema spp. Pharm: Cytotoxic (KB, MIC = 1–5 ng/mL; LoVo, MIC = 10–50 ng/mL); antifungal (agar diffusion assay: Aspergillus oryzae, Candida albicans, Penicillium notatum and Saccharomyces cerevisiae). Ref: S. Carmeli, et al, JNP, 1990, 53, 1533 H O

N

O H

O

OH 19

O

O

O

H O OH

O

OH

208

1 Polyketides

516 73-Deoxychondropsin A Type: Other macrocyclic polyketide lactones. C83H133N3O25 Powder, [α]D = +2° (c = 0.3, MeOH). Source: Sponge Ircinia ramosa (Australia). Pharm: Cytotoxic (in vitro, hmn melanoma LOX cell lines, IC50 = 0.8 ng/mL; hmn leukemia Molt4 cell lines, IC50 = 0.2 ng/mL). Ref: M. A. Rashid, et al, Tet. Lett., 2001, 42, 1623

O

OH

O

O

OH

OH

H N

O

73

HO HN 32

OH

OH

OH

O

O 67

OH

O

OH

O HOOC

H N O HO

O

1

O COOH

517 13-Deoxytedanolide Type: Other macrocyclic polyketide lactones. C32H50O10 [α]D = +84.4° (c = 0.26, CHCl3). Source: Sponge Mycale adhaerens. Pharm: Cytotoxic (P388, in vitro, IC50 = 94pg/mL); Antineoplastic (P388 in vivo, 0.125 mg/kg, T/C = 189%). Ref: N. Fusetani, et al, JOC, 1991, 56, 4971│S. Nishimura, et al, BoMC, 2005, 13, 449; 455│J. R. Dunetz, et al, JACS, 2008, 130, 16407 OH OH

O O

O

O

H O

13

OH

O

O

518 Dictyostatin Dictyostatin-1 Type: Other macrocyclic polyketide lactones. C32H52O6 Amorph. solid, mp 87–88 °C, [α]D22 = −20° (c = 0.1, MeOH). Source: Sponge Spongia sp. (Maldives), an unidentified lithistid sponge (family Neopeltidae, off north coast, Jamaica, depth of 442m, using Johnson-Sea-Link submersible). Pharm: Arrests cells in G2/M phase of cell cycle; cytotoxic (hmn cancer cell lines: A549, IC50 = 0.95 nmol/L, control Paclitaxel, IC50 = 5.13 nmol/L; MCF7, IC50 = 1.5 nmol/L, Paclitaxel, IC50 = 2.5 nmol/L; MES-SA, IC50 = 4.1 nmol/L, Paclitaxel, IC50 = 3.3 nmol/L; multidrugresistant NCI-ADR, IC50 = 20 nmol/L, Paclitaxel, IC50 = 3331 nmol/L; MES-SA/DX5,

1.33 Other Macrocyclic Polyketide Lactones

209

IC50 = 11 nmol/L, Paclitaxel, IC50 = 1654 nmol/L) (Isbrucker, 2004); cytotoxic (approximately tenfold greater cytotoxicity than discodermolide for majority of tumor cell lines assayed and has virtually no drop in potency in multi-drug resistant cancer cell lines expressing p-glycoprotein efflux pump); cytotoxic (mode of action: works through polymerization of tubulin and stabilization of microtubules); potent promotor of tubulin assembly (similar to paclitaxel and discodermolide); anti-AD preclinical trial (Target: MT-stabilizing agent, Animal Model: CD1 mice. Effects: MTstabilization in the brain one week after 5 mg/kg ip administration) (Russo, 2016). Ref: G. R. Pettit, et al, Chem. Comm., 1994, 1111│R. A. Isbrucker, et al, Biochem. Pharmacol., 2004, 66, 75│G. J. Florence, et al, NPR, 2008, 25, 342│A. E. Wright, Current Opinion in Biotechnology 2010, 21, 801│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)│P. Russo, et al, Mar. Drugs, 2016, 14, 5 (review)

OH HO O

OH

O

OH

519 Dihydroprorocentrolide Type: Other macrocyclic polyketide lactones. C56H87NO13 Source: Dinoflagellate Prorocentrum lima. Pharm: Paralytic phycotoxin; LD50 (mus, ipr) 0.14 mg/kg. Ref: K. Torigoe, et al, JACS, 1988, 110, 7876│K. Torigoe, et al, CA, 1989, 111, 173876d OH OH OH

O

N OH

O OH O

O

O

HO OH 9

OH 54

210

1 Polyketides

520 Dolabelide A Type: Other macrocyclic polyketide lactones. C43H72O13 [α]D25 = −13.5° (c = 1.45, CHCl3). Source: Sea hare Dolabella auricularia (yield = 8.8 × 10−5%ww). Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 6.3 μg/mL). Ref: M. Ojika, et al, Tet. Lett., 1995, 36, 7491

O

O

O

O

O

OH

O OH

O

O

OH

O

O

521 Dolabelide B Type: Other macrocyclic polyketide lactones. C41H70O12 [α]D24 = +4.0° (c = 0.43, CHCl3). Source: Sea hare Dolabella auricularia (yield = 2.4 × 10−5%ww). Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 1.3 μg/mL). Ref: M. Ojika, et al, Tet. Lett., 1995, 36, 7491

O

O

O

OH

O

O OH

HO

OH

O

O

O

522 Dolabelide C Type: Other macrocyclic polyketide lactones. C43H72O13 Oil, [α]D26 = +10° (c = 0.2, CHCl3). Source: Sea hare Dolabella auricularia (Japan waters). Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 1.9 μg/mL). Ref: K. Suenaga, et al, JNP, 1997, 60, 155 O

O O

O

OH 7

11

O

O

OH

O

O

O O

OH

1.33 Other Macrocyclic Polyketide Lactones

211

523 Dolabelide D Type: Other macrocyclic polyketide lactones. C39H68O11 Oil, [α]D29 = +2.6° (c = 0.3, CHCl3). Source: Sea hare Dolabella auricularia (Japan waters). Pharm: Cytotoxic (HeLa-S3 cells, IC50 = 1.9 μg/mL). Ref: K. Suenaga, et al, JNP, 1997, 60, 155 O O

OH

OH

7 11

OH

OH

O

O

O O

OH

524 Fijianolide A Isolaulimalide; Isolaulamide Type: Other macrocyclic polyketide lactones. C30H42O7 [α]D20 = −8° (c = 0.04, CHCl3). Source: Sponges Spongia mycofijiensis, Hyattella sp. and Fasciospongia rimosa, nudibranch Chromodoris lochi. Pharm: Microtubule stabilizer (potent); cytotoxic (moderate). Ref: Quiñoà, E. et al, JOC, 1988, 53, 3642│ D. G. Corley,et al, JOC, 1988, 53, 3644│J. Tanaka, et al, Chem. Lett., 1996, 255│ Gollner, et al, Chem. Eur. J., 2009, 15, 5979

O O O

OH O

H OH

O

525 Goniodomin A Type: Other macrocyclic polyketide lactones. C43H60O12 [α]D20 = +28° (c = 0.13, MeOH). Source: Dinoflagellate Alexandrium hiranoi [Syn. Goniodoma pseudogoniaulax]. Pharm: Antifungal; actinomyosin ATP-ase modulator. Ref: M. Murakami, et al, Tet. Lett., 1988, 29, 1149│K. I. Furukawa, et al, J. Biol. Chem., 1993, 268, 26026│ Y. Takeda, et al, Org. Lett., 2008, 10, 1013

212

1 Polyketides

H H H

O

OH OH

O

H

HO H O O

O

O

H

H

H

O

H

OH

O

526 Haterumalide B Type: Other macrocyclic polyketide lactones. C28H37ClO9 Oil, [α]D = 0° (CHCl3). Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic (inhibits cell division in fertilized sea urchin eggs at 0.01 μg/mL). Ref: K. Ueda, et al, Tet. Lett., 1999, 40, 6305│H. Kigoshi,et al, Org. Lett., 2003, 5, 957 H

Cl

9

O

O O O

H

OH O

H

O

3

O O

527 Haterumalide NA Type: Other macrocyclic polyketide lactones. C23H31O8Cl Powder, mp 106–108 °C, [α]D26 = −3.0° (c = 0.053, MeOH). Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic (P388 cells, IC50 = 0.32 μg/mL); LD99 = 0.24 μg/mL. Ref: N. Takada, et al, Tet. Lett., 1999, 40, 6309│H. Kigoshi,et al, Org. Lett., 2003, 5, 957 H

Cl

9

O O

H OH

O O

H

3 20

O

COOH

528 Haterumalide NB Type: Other macrocyclic polyketide lactones. C27H39ClO8 Oil. Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic. Ref: N. Takada, et al, Tet. Lett., 1999, 40, 6309│ H. Kigoshi,et al, Org. Lett., 2003, 5, 957

1.33 Other Macrocyclic Polyketide Lactones

213

H

Cl

9

O

H

O

OH

O

H O

3

O

O

20

O

529 Haterumalide NC Type: Other macrocyclic polyketide lactones. C27H39ClO9 Oil. Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic. Ref: N. Takada, et al, Tet. Lett., 1999, 40, 6309│ H. Kigoshi,et al, Org. Lett., 2003, 5, 957 HO H

Cl

9

O

H

O

OH

O

H O

3

O

O

20

O

530 Haterumalide ND Type: Other macrocyclic polyketide lactones. C23H31O9Cl Oil. Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic. Ref: N. Takada, et al, Tet. Lett., 1999, 40, 6309│ H. Kigoshi,et al, Org. Lett., 2003, 5, 957 HO H

Cl

9

O O

H OH

O O

H

3 20

OH

O O

531 Haterumalide NE Type: Other macrocyclic polyketide lactones. C21H29O7Cl Oil. Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic; antifungal. Ref: N. Takada, et al, Tet. Lett., 1999, 40, 6309│H. Kigoshi,et al, Org. Lett., 2003, 5, 957

214

1 Polyketides

H

Cl

O

H OH

OH O

H

O

COOH

532 13-Hydroxy-15-O-methylenigmazole A Type: Other macrocyclic polyketide lactones. C30H48NO10P Pale yellow solid, [α]D25 = −7.8° (c = 0.1, MeOH). Source: Sponge Cinachyrella enigmatica. Pharm: Cytotoxic. Ref: N. Oku, et al, JACS, 2010, 132, 10278 OH 13R 15

O O

OH O O

H

N

O

O

O P

HO

OH

533 6-Hydroxy-7-O-methylscytophycin E Type: Other macrocyclic polyketide lactones. C46H77NO13 Amorph. solid. Source: Cyanobacteria Scytonema musicola, Scytonema ocellatum, Scytonema mirabile, Scytonema burmanicum and Cylindrospermum musicola. Pharm: Cytotoxic (KB, MIC = 1–5 ng/mL; LoVo, MIC = 10–50 ng/mL); antifungal (agar diffusion assay: Aspergillus oryzae, Candida albicans, Penicillium notatum and Saccharomyces cerevisiae). Ref: S. Carmeli, et al, JNP, 1990, 53, 1533 H O

N

O

HO H

H

O O HO

O O

O

O

O

O

OH

1.33 Other Macrocyclic Polyketide Lactones

215

534 6-Hydroxyscytophycin B Type: Other macrocyclic polyketide lactones. C45H73NO13 Powder. Source: Cyanobacteria Scytonema spp. and Cylindrospermum musicola. Pharm: Cytotoxic. Ref: J. H. Jung, et al, Phytochemistry, 1991, 30, 3615 H O

N

O H

H

O O HO

O

O

O O O

OH

OH

O

535 Iejimalide A Type: Other macrocyclic polyketide lactones. C40H58N2O7 Non-cryst. solid, mp 71–73 °C, [α]D23 = −36.4° (c = 0.17, CHCl3). Source: Ascidians Eudistoma cf. rigida and Cystodytes sp. Pharm: Antineoplastic (mice bearing ip-innoculated P388 leukemia, 200 μg/kg/day, T/C = 120%); cytotoxic (39 human cancer cell lines, mean log GI50 (mol/L) = −6.31, COMPARE analyses were negative, indicating there are no standard anticancer drugs with a high correlation coefficient (R < 0.5)). Ref: J. Kobayashi, et al, JOC, 1988, 53, 6147│K. Nozawa, et al, BoMC, 2006, 14, 1063

O O

O O

N H

O NH

OH

O

536 Iejimalide B Type: Other macrocyclic polyketide lactones. C41H60N2O7 Non-cryst. solid, mp 69–71 °C, [α]D23 = −17.6° (c = 0.17, MeOH). Source: Ascidian Eudistoma cf. rigida. Pharm: Antineoplastic (mice bearing ip-innoculated P388 leukemia, 200 μg/kg/day, T/C = 120%); cytotoxic (39 human cancer cell lines, mean log GI50 (mol/L) = −6.67, COMPARE analyses were negative, indicating there are no standard anticancer drugs with a high correlation coefficient (R < 0.5)). Ref: J. Kobayashi, et al, JOC, 1988, 53, 6147│K. Nozawa, et al, BoMC, 2006, 14, 1063

216

1 Polyketides

O O O

O

NH

N H

O

OH

O

537 Iejimalide C Type: Other macrocyclic polyketide lactones. C40H58N2O10S [α]D20 = −56° (c = 0.13, MeOH). Source: Ascidians Eudistoma cf. rigida (Na salt) and Cystodytes sp. Pharm: Antineopalstic (mice bearing ip-innoculated P388 leukemia, 200 μg/kg/day, T/C = 150%); cytotoxic (39 human cancer cell lines, mean log GI50 (mol/L) = −6.11, COMPARE analyses were negative, indicating there are no standard anticancer drugs with a high correlation coefficient (R < 0.5)). Ref: Y. Kikuchi, et al, Tet. Lett., 1991, 32, 797│K. Nozawa, et al, BoMC, 2006, 14, 1063 O O O

O O

NH

N H

O O

S O OH

O

538 Iejimalide D Type: Other macrocyclic polyketide lactones. C41H60N2O10S Source: Ascidian Eudistoma cf. rigida. Pharm: Antineoplastic (mice bearing ip-innoculated P388 leukemia, 200 μg/kg/day, T/C = 150%); cytotoxic (39 human cancer cell lines, mean log GI50 (mol/L) = −6.28, COMPARE analyses were negative, indicating there are no standard anticancer drugs with a high correlation coefficient (R < 0.5)). Ref: Y. Kikuchi, et al, Tet. Lett., 1991, 32, 797│K. Nozawa, et al, BoMC, 2006, 14, 1063 O O O

O O

N H

NH

O O S O

O

OH

1.33 Other Macrocyclic Polyketide Lactones

217

539 Iriomoteolide 4a Type: Other macrocyclic polyketide lactones. C29H48O7 Source: Dinofiagellate Amphidinium sp. (sediment, Iriomote I., Okinawa). Pharm: Cytotoxic (DG-75, moderate). Ref: K. Kumagai,et al, Heterocycles, 2013, 87, 2615 OH

HO

OH

OH

O O

OH

540 Iriomoteolide 5a Type: Other macrocyclic polyketide lactones. C31H52O7 Source: Unidentified dinoflagellate. Pharm: Cytotoxic (DG-75, moderate). Ref: K. Kumagai,et al, Heterocycles, 2013, 87, 2615

OH

OH HO

OH O OH

O

541 Laulimalide Fijianolide B; Laulamide Type: Other macrocyclic polyketide lactones. C30H42O7 Oil, [α]D20 = −8° (c = 0.04, CHCl3). Source: Sponge Hyattella sp. Pharm: Cytotoxic (KB cell line, IC50 = 1.5 ng/mL). Ref: D. G. Corley, et al, JOC, 1988, 53, 3644 H O

H

O OH

O H

H OH O

O

218

1 Polyketides

542 Levantilide A Type: Other macrocyclic polyketide lactones. C30H52O6 Colorless amorph. solid, [α]D20 = −72.4° (c = 0.145, MeOH). Source: Marine-derived bacterium Micromonospora sp. M71-A77 (depth of 4400m, deep sea sediment, Levantine Sea, Eastern Mediterranean). Pharm: Cytotoxic (antiproliferative, GXF-251L, IC50 = 40.9 μmol/L, LXF-529L, IC50 = 39.4 μmol/L, MAXF-401NL, IC50 = 28.3 μmol/L, MEXF-462NL, IC50 = 48.6 μmol/L, PAXF-1657L, IC50 = 20.7 μmol/L, RXF-486L, IC50 = 52.4 μmol/L). Ref: A. Gärtner, et al, Mar. Drugs, 2011, 9, 98

O OH

OH O

HO

OH

543 Lustromycin Type: Other macrocyclic polyketide lactones. C32H38O13 Needles, mp 230–233 °C. Source: Marine-derived streptomycete Streptomyces sp. SK 1071. Pharm: Antibacterial (including Clostridium sp.). Ref: H. Tomoda, et al, J. Antibiot., 1986, 39, 1205│M. Handa, et al, Heterocycles, 2003, 59, 497

O OH

O

O

O O

O O O

O O

O OH

544 Lyngbouilloside Type: Other macrocyclic polyketide lactones. C31H52O10 Amorph. solid, [α]D25 = −38° (c = 0.46, CHCl3). Source: Cyanobacterium Lyngbya sp. (Papua New Guinea). Pharm: Cytotoxic (moderate). Ref: L. T. Tan, et al, JNP, 2002, 65, 925│ A. ElMarrouni, et al, Org. Lett., 2012, 14, 314

1.33 Other Macrocyclic Polyketide Lactones

219

OH O

O

O

O

HO O O

O OH

545 Lyngbyaloside Type: Other macrocyclic polyketide lactones. C31H49BrO10 Amorph. solid. Source: Cyanobacteria Lyngbya bouillonii and Lyngbya sp. (Palau, Oceania). Pharm: Cytotoxic (KB nasopharyngeal carcinoma and LoVo colon adenocarcinoma). Ref: D. Klein, et al, JNP, 1997, 60, 1057│H. Luesch, et al, JNP 2002, 65, 1945│ S. Matthew, et al, JNP, 2010, 73, 1544 O

O

O

O O HO

OH

H

O

O O

Br

546 Maduralide Type: Other macrocyclic polyketide lactones. C42H68O13 Oil, [α]D = −46.3° (c = 0.32, CHCl3). Source: An unidentified marine bacterium (Actinomycetales and Maduromycetes). Pharm: Antibacterial (weak). Ref: C. Pathirana, et al, Tet. Lett., 1991, 32, 2323 O

O

HO

O

O O

O OH

OH

O OH

O OH

220

1 Polyketides

547 Mandelalide A Type: Other macrocyclic polyketide lactones. C34H54O10 Source: Ascidian Lissoclinum sp. (Algoa Bay, southeast coast of South Africa). Pharm: Cytotoxic (hmn NCI-H460 lung, IC50 (at 48h) = 12 nmol/L, mouse neuro-2a neuroblastoma, IC50 (at 48h) = 44 nmol/L). Ref: J. Sikorska, et al, JOC, 2012, 77, 6066 OH O O O

O

O

O O

OH OH

548 Mandelalide B Type: Other macrocyclic polyketide lactones. C37H58O13 Source: Ascidian Lissoclinum sp. (Algoa Bay, southeast coast of South Africa). Pharm: Cytotoxic (hmn NCI-H460 lung, IC50 (at 48h) = 29 nmol/L, mouse neuro-2a neuroblastoma, IC50 (at 48h) = 84 nmol/L). Ref: J. Sikorska, et al, JOC, 2012, 77, 6066│J. Willwacher, et al, Chem. Eur. J., 2015, 21, 10416

H

H O HO

O

H

O HO O

O O

O HO

O

O OH

549 Mangromicin A Type: Other macrocyclic polyketide lactones. C22H34O7 Source: Mangrove Lechevalieria aerocolonigenes. Pharm: Antitrypanosomal (potent); antioxidant (DPPH radical scavenger). Ref: T. Nakashima, et al, J. Antibiot., 2014, 67, 253│T. Nakashima, et al, J. Antibiot., 2014, 67, 533

1.33 Other Macrocyclic Polyketide Lactones

221

OH

O

O

OH

O

O OH

550 Marinomycin A Type: Other macrocyclic polyketide lactones. C58H76O14 Yellow powder, [α]D = −161° (c = 0.13, EtOH). Source: Marine-derived actinomycete Marinispora sp. CNQ-140. Pharm: Antibacterial (Staphylococcus aureus and Enterococcus faecium, IC50 = 0.1–0.6 μmol/L). Ref: H. C. Kwon, et al, JACS, 2006, 128, 1622; 16410 HO 28

HO

2 8

O

O

OH

OH

OH OH

OH

OH

O

O

8'

OH

2

OH

551 Marinomycin B Type: Other macrocyclic polyketide lactones. C58H76O14 Yellow powder, [α]D = −245° (c = 0.15, EtOH). Source: Marine-derived actinomycete Marinispora sp. CNQ-140. Pharm: Antibacterial (Staphylococcus aureus and Enterococcus faecium, IC50 = 0.1–0.6 μmol/L). Ref: H. C. Kwon, et al, JACS, 2006, 128, 1622; 16410 HO

2

8Z

HO O

O

OH

OH

OH OH

OH

OH 8'Z

O

28

O OH

2

OH

552 Marinomycin C Type: Other macrocyclic polyketide lactones. C58H76O14 Yellow powder, [α]D = −161° (c = 0.13, EtOH). Source: Marine-derived actinomycete Marinispora sp. CNQ-140. Pharm: Antibacterial (Staphyloccocus aureus and Enterococcus faecium, IC50 = 0.1–0.6 μmol/L). Ref: H. C. Kwon, et al, JACS, 2006, 128, 1622; 16410

222

1 Polyketides

HO 28

2

8Z

HO O

O

OH

OH

OH

OH OH

OH

O

O

8'

OH 2

OH

553 Marinomycin D Type: Other macrocyclic polyketide lactones. C59H78O14 Yellow powder, [α]D = −233° (c = 0.03, EtOH). Source: Marine-derived actinomycete Marinispora sp. CNQ-140. Pharm: Antibacterial (Staphyloccocus aureus and Enterococcus faecium, IC50 = 0.1–0.6 μmol/L). Ref: H. C. Kwon, et al, JACS, 2006, 128, 1622; 16410 HO 28

2

8Z

HO O

O

OH

OH

OH

OH OH

OH

O 8'Z

O OH

2

OH

554 15-O-Methylenigmazole A Type: Other macrocyclic polyketide lactones. C30H48NO10P Pale yellow solid, [α]D25 = −13.3° (c = 0.1, MeOH). Source: Sponge Cinachyrella enigmatica. Pharm: Cytotoxic. Ref: N. Oku, et al, JACS, 2010, 132, 10278 13 15

O O

OH O O

N O

H O

O P

HO

OH

555 Mirabalin Mirabilin Type: Other macrocyclic polyketide lactones. C76H123N3O22 Pale yellow powder, [α]D25 = −14° (c = 0.05, MeOH). Source: Lithistid sponge Siliquariaspongia mirabilis (southeast of Chuuk Lagoon, Federated States of Micronesia). Pharm: Cytotoxic (HCT116 cell line, IC50 = 0.27 μmol/L, inhibits cell growth). Ref: A. Plaza, et al, JNP, 2008, 71, 473; 2009, 72, 324│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

1.33 Other Macrocyclic Polyketide Lactones

OH

223

OH

H N OH

O

H

O

HO

HO

HN

O

O

OH

OH

OH

OH H N

O

O HO

O

O

OH O

H

OH

O

556 Neolaulimalide Type: Other macrocyclic polyketide lactones. C30H42O7 [α]D26 = −57° (c = 0.09, CHCl3). Source: Sponge Fasciospongia rimosa (Okinawa). Pharm: Cytotoxic (P388, A549, HT29, MEL28 cells line, IC50 = 0.01–0.05 μg/mL). Ref: J. Tanaka, et al, Chem. Lett., 1996, 255│A. Gollner, et al, Chem. Eur. J., 2009, 15, 5979 H

H O O

O

HO

O

OH H

H

O

557 Neristatin I Type: Other macrocyclic polyketide lactones. C41H60O15 Powder, mp 214–216 °C, [α]D = +98° (c = 0.26, CH2Cl2). Source: Bryozoan Bugula neritina. Pharm: Cytotoxic (P388, ED50 = 10 μg/mL, weak); binds to Protein Kinase C (PKC). Ref: G. R. Pettit, et al, JACS, 1991, 113, 6693 O O

H

OH

O

O

H

H

O O OH

O

O

O

O

O

O H

OH

224

1 Polyketides

558 Octalactin A Type: Other macrocyclic polyketide lactones. C19H32O6 Crystals (CHCl3/EtOAc), mp 155–157 °C, [α]D = −14° (c = 1.8, CHCl3). Source: Marine-derived streptomycete Streptomyces sp. from an unidentified gorgonian. Pharm: Cytotoxic (B16-F-10, IC50 = 0.0072 μg/mL; HCT116, IC50 = 0.5 μg/mL). Ref: D. M. Tapiolas, et al, JACS, 1991, 113, 4682│ M. Kodama, M. et al, Chem. Lett., 1997, 117 O HO

O

OH

O

O

559 Orbuticin Type: Other macrocyclic polyketide lactones. C32H38O14 Amorph. solid, mp 240 °C (dec). Source: Marine-derived fungus Hypoxylon oceanicum LL-15G256. Pharm: Antifungal. Ref: J. Breinholt, et al, J. Antibiot., 1993, 46, 1101 OH O HO

O

O O

O

OH

O O

O O

OH O

560 Oscillariolide Type: Other macrocyclic polyketide lactones. C41H69BrO11 Source: Cyanobacterium Oscillatoria sp. Pharm: cytotoxic (inhibits development of fertilised echinoderm eggs). Ref: M. Murakami, et al, Tet. Lett., 1991, 32, 2391│R. T. Williamson, et al, JOC, 2002, 67, 7927 OH

Br

OH

OH

OH

OH

O O

O OH O

HO

1.33 Other Macrocyclic Polyketide Lactones

225

561 Paciforgin Type: Other macrocyclic polyketide lactones. C21H34O8 Cryst. Source: Soft coral Pacifigorgia sp. Pharm: Antifungal. Ref: R. M. Perez Gutierrez, et al, Drugs Exp. Clin. Res., 1990, 16, 505

OH OH OH HO

O

O O

HO

562 Palmerolide A Type: Other macrocyclic polyketide lactones. C33H48N2O7 Amorph. solid, [α]D24 = −1.6° (c = 0.5, MeOH). Source: Ascidian Synoicum adareanum (psychrophilic, cold water, circumpolar, colonial, near Anvers I., Antarctica). Pharm: Cytotoxic (melanoma, e.g. UACC62, LC50 = 18 nmol/L, in NCI’s 60 cell line panel with three orders of magnitude greater sensitivity relative to other cell lines tested, by inhibition of vacuolar ATPase, IC50 = 2 nmol/L). Ref: K. C. Nicolaou, et al, Angew. Chem., Int. Ed., 2007, 46, 5896│ X. Jiang, et al, JACS, 2007, 129, 6386│ M. D. Lebar, et al, Tet. Lett., 2007, 48, 8009│ M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

O H N

H

O

O

OH HO

O O

NH2

563 Palmyrolide A Type: Other macrocyclic polyketide lactones. C20H35NO3 Source: Cyanobacteria Leptolyngbya cf. and Oscillatoria spp. (assemblage, Palmyra Atoll, Northern Pacific Ocean). Pharm: Anticancer-Cell-Effect (model: mouse neuroblastoma neuro-2a cells, mechanism: sodium influx inhibition); sodium channel blocker (neuro-2a cells, IC50 = 5.2 μmol/L without appreciable cytotoxicity, since Palmyrolide A is a stronger veratridine and ouabain induced sodium overload inhibitor with IC50 = 3.70 μmol/L). Ref: A. R. Pereira, et al, Org. Lett., 2010, 12, 4490

226

1 Polyketides

O 18

16

N

1

O

20

13

5

19

O

7 8

12

11 9

10

Syn relative configuration between C5 and C7

564 Peloruside A Type: Other macrocyclic polyketide lactones. C27H48O11 Oil, [α]D20 = +16° (c = 0.3, CH2Cl2). Source: Sponge Mycale hentscheli. Pharm: Cytotoxic; antimitotic (Taxollike microtubule stabilizing activity). Ref: L. M. West, et al, JOC, 2000, 65, 445│ K. A. Hood, et al, Cancer Res., 2002, 62, 3356│X. Liao, et al, Angew. Chem., Int. Ed., 2003, 42, 1648 O OH OH O HO

3

OH

O

O

O O

HO

565 Peloruside B Type: Other macrocyclic polyketide lactones. C26H46O11 Source: Sponge Mycale hentscheli (Kapiti I., New Zealand). Pharm: Cytotoxic. Ref: A. J. Singh, et al, JOC, 2010, 75, 2 O OH OH O HO

O

3

OH

OH O O

HO

1.33 Other Macrocyclic Polyketide Lactones

227

566 Phormidolide Type: Other macrocyclic polyketide lactones. C59H97BrO12 Oil, [α]D25 = +48° (c = 0.25, CHCl3). Source: Cyanobacterium Phormidium sp. Pharm: Toxic (brine shrimp, LC50 = 1.5 μmol/L). Ref: R. T. Williamson, et al, JOC, 2002, 67, 7927; 2003, 68, 2060 O O

OH

O

O OH

OH

OH

OH

OH

Br O

O

567 Polycavernoside A Type: Other macrocyclic polyketide lactones. C43H68O15 Amorph. solid. Source: Red alga Polycavernosa tsudai [Syn. Gracilaria edulis]. Pharm: Causative agent of an outbreak of hmn illness and death in Guan that resulted from eating Polycavernosa tsudai; toxin; LD50 (mus, ipr.) = 0.2 mg/kg. Ref: M. Yotsu-Yamashita, et al, JACS, 1993, 115, 1147│ M. Yotsu-Yamashita, et al, Tet. Lett., 1995, 36, 5563│K. Fujiwara, et al, Chem. Lett., 1995, 191│K. Fujiwara, et al, Chem. Lett., 1995, 855│J. N. Johnson, et al, Tet. Lett., 1995, 36, 4341│K. Fujiwara, et al, JACS, 1998, 120, 10770│ L. A. Paquette, et al, JACS, 1999, 121, 4542│K. Fujiwara, et al, J. Synth. Org Chem., Jpn., 1999, 57, 993│L. A. Paquette, et al, JACS, 2000, 122, 619 O

HO O

HO

O

O

O O

O

O

O

O

O

O

O

568 Polycavernoside A2 Type: Other macrocyclic polyketide lactones. C42H66O15 Oil. Source: Red alga Polycavernosa tsudai [Syn. Gracilaria edulis]. Pharm: Toxin. Ref: M. Yotsu-Yamashita, et al, Tet. Lett., 1995, 36, 5563 HO O O HO O

HO

O O

O

O O

O

O

H O O

228

1 Polyketides

569 Polycavernoside A3 Type: Other macrocyclic polyketide lactones. C44H70O15 Oil. Source: Red alga Polycavernosa tsudai [Syn. Gracilaria edulis]. Pharm: Toxin. Ref: M. Yotsu-Yamashita, et al, Tet. Lett., 1995, 36, 5563

O HO O O

O

O

O

O

O

H

O

O

O

O

O

O

570 Polycavernoside B Type: Other macrocyclic polyketide lactones. C45H70O16 Oil. Source: Red alga Polycavernosa tsudai [Syn. Gracilaria edulis]. Pharm: Toxic (hmn intoxication). Ref: M. Yotsu-Yamashita, et al, Tet. Lett., 1995, 36, 5563 HO O O O

O

O

O O

O

O

H

O

O

O

O

O

O

571 Polycavernoside B2 Type: Other macrocyclic polyketide lactones. C43H68O15 Oil. Source: Red alga Polycavernosa tsudai [Syn. Gracilaria edulis]. Pharm: Toxin. Ref: M. Yotsu-Yamashita, et al, Tet. Lett., 1995, 36, 5563 HO O O H

HO O

O O

O O

O

O O

O O

O

572 Precandidaspongiolide A Type: Other macrocyclic polyketide lactones. C32H50O13 Source: Sponge Candidaspongia sp. (Papua New Guinea). Pharm: Cytotoxic (Precandidaspongiolide A/B mixture, A:B = 4.5:1, melanoma UACC-257, IC50 = (14.2 ± 0.2)nmol/L; melanoma LOX-IMVI, IC50 = (6.9 ± 1.0)nmol/L; melanoma M14, IC50 = (17.9 ± 4.4)nmol/L; MCF7,

1.33 Other Macrocyclic Polyketide Lactones

229

IC50 = (8.3 ± 0.5)nmol/L; NCI-H460, IC50 = (12.3 ± 1.0)nmol/L). Ref: E. L. Whitson, et al, Org. Lett., 2011, 13, 3518 OH O

O

OH

OH O HO

O

O

OH

O OH

O

573 Precandidaspongiolide B Type: Other macrocyclic polyketide lactones. C32H50O13 Source: Sponge Candidaspongia sp. (Papua New Guinea). Pharm: Cytotoxic (Precandidaspongiolide A/B mixture, A:B = 4.5:1, melanoma UACC-257, IC50 = (14.2 ± 0.2)nmol/L; melanoma LOX-IMVI, IC50 = (6.9 ± 1.0)nmol/L; melanoma M14, IC50 = (17.9 ± 4.4)nmol/L; MCF7, IC50 = (8.3 ± 0.5)nmol/L; NCI-H460, IC50 = (12.3 ± 1.0)nmol/L). Ref: E. L. Whitson, et al, Org. Lett., 2011, 13, 3518 OH O

O

OH

OH O HO

O

O

OH

O O

OH

574 Prorocentrolide Type: Other macrocyclic polyketide lactones. C56H85NO13 Amorph. solid, [α]D23 = +136.5° (c = 0.147, MeOH). Source: Dinoflagellate Prorocentrum lima. Pharm: Phycotoxin. Ref: K. Torigoe, et al, JACS, 1988, 110, 7876│K. Torigoe, et al, CA, 1989, 111, 173876d OH OH O OH N OH

O OH O

O

O

HO OH 9

OH 54

230

1 Polyketides

575 Prorocentrolide B Type: Other macrocyclic polyketide lactones. C56H85NO17S Solid, mp 199–201 °C, [α]D25 = +76.7° (c = 0.2, MeOH). Source: Dinoflagellate Prorocentrum maculosum. Pharm: Toxic (fast-acting). Ref: T. Hu, et al, JNP, 1996, 59, 1010 OH OH OH

O

N OH

O O

HO

O

O

O

OH OH

OH

O S

OH

O

576 Salarin A Type: Other macrocyclic polyketide lactones. C35H46N2O12 Pale yellow oil, [α]D23 = −57° (c = 0.37, CHCl3). Source: Sponge Fascaplysinopsis sp. Pharm: Cytotoxic (MTT assay, 0.5 μg/mL 3 days culture, UT7, InRt = 20%, 1 μg/mL, InRt = 45%; K562, inactive). Ref: A. Bishara, et al, Org. Lett., 2008, 10, 153; 2009, 11, 3538

H N

O O

N O

O

O

O

O O

O

O

O O

577 Scytophycin E Type: Other macrocyclic polyketide lactones. C45H75NO12 Amorph. solid, [α]D19 = −38° (c = 1.0, MeOH). Source: Cyanobacteria Scytonema pseudohofmanni and Cylindrospermum musicola. Pharm: Cytotoxic (KB, MIC = 1–5 ng/mL; LoVo, MIC = 10–50 ng/mL). Ref: M. Ishibashi, et al, JOC, 1986, 51, 5300│R. E. Moore, et al, CA, 1987, 106, 153049│S. Carmeli, et al, JNP, 1990, 53, 1533

1.33 Other Macrocyclic Polyketide Lactones

231

H O

HO

N

O 34

H

O

O O

O

O

H O OH

OH

O

578 Spiroprorocentrimine Type: Other macrocyclic polyketide lactones. C42H69NO13S Cryst. (MeOH), [α]D = −51.4° (c = 0.28, MeOH). Source: Dinoflagellate Prorocentrum sp. (benthic) from epiphytes of coral reef seaweeds (Taiwan waters). Pharm: Low toxic (intraperitoneal mus bioassay, much less toxic than other known cyclic imine toxins). Ref: C. -K. Lu, et al, Tet. Lett., 2001, 42, 1713 OH OH O OH

H N

O

+

O

S O

–

O

OH O

OH

O

OH

579 Spongistatin 1 Altohyrtin A Type: Other macrocyclic polyketide lactones. C63H95ClO21 Amorph. powder (Na salt), mp 161–162 °C (Na salt), [α]D22 = +26.2° (c = 0.32, MeOH) (Na salt). Source: Sponges Spongia sp. (Maldives) and Hyrtios altum (Okinawa). Pharm: Cytotoxic (in vitro NCI’s primary screen assay, mean GI50 = 1.17 × 10−10 mol/L, compare correlation coefficient = 1.00); cytotoxic (GI50 typically = 2.5–3.5 × 10−11 mol/L against a subset of highly chemoresistant tumor types, e.g., HL60, SR; NCI-H226, NCI-H23, NCI-H460, NCI-H522; DMS114, and DMS273; HCT116, HT29, KM12, KM20L2 and SW620; SF539, U251; SK-MEL-5; OVCAR-3; and RXF-393). Ref: G. R. Pettit, et al, JOC, 1993, 58, 1302│G. R. Pettit, et al, J. Chem. Soc., Chem. Commun., 1993, 1805│G. R. Pettit, et al, J. Chem. Soc., Chem. Commun., 1993, 1166│ M. Kobayashi, et al, CPB, 1993, 41, 989; 1996, 44, 2142

232

1 Polyketides

Cl 50

OH O

O H

OH

O HO HO

HO

5

O

OH

O

H

H O

O

O H

O OH

O

H O H

15

H

O O O

580 Spongistatin 2 Altohyrtin C Type: Other macrocyclic polyketide lactones. C63H96O21 Amorph. solid, mp 140–141 °C, [α]D = +24.5° (c = 0.39, MeOH); [α]D = +31° (c = 0.3, MeOH). Source: Sponges Spongia sp. (Maldives) and Hyrtios altum (Okinawa). Pharm: Cytotoxic (KB, IC50 = 0.4 ng/mL; L1210, IC50 = 1.3 ng/mL). Ref: G. R. Pettit, et al, JOC, 1993, 58, 1302│G. R. Pettit, et al, J. Chem. Soc., Chem. Commun., 1993, 1166│M. Kobayashi, et al, Tet. Lett., 1993, 34, 2795│ M. Kobayashi, et al, CPB, 1993, 41, 989│ M. Kobayashi, et al, Tet. Lett., 1994, 35, 1243│D. A. Evans, et al, Tetrahedron, 1999, 55, 8671

50

OH O

O H

OH

O HO HO

HO

5

O

OH

O

H

H O

O

O H

O OH

O

H O H

15

H

O O O

1.33 Other Macrocyclic Polyketide Lactones

233

581 Spongistatin 3 5-De-O-acetylaltohyrtin A Type: Other macrocyclic polyketide lactones. C61H93ClO20 Powder, mp 148–149 °C, [α]D = +28.1° (c = 0.15, MeOH). Source: Sponges Spongia sp. (Maldives) and Hyrtios altum (Okinawa). Pharm: Cytotoxic (KB, IC50 = 0.3 ng/mL). Ref: M. Kobayashi, et al, CPB, 1993, 41, 989│G. R. Pettit, et al, J. Chem. Soc., Chem. Commun., 1993, 1166│ M. Kobayashi, et al, Tet. Lett., 1994, 35, 1243

15

O

O

HO

O

O

O

O

O

O

5

HO

HO O

O OH

HO

O

50

O Cl

H

OH

OH

OH

582 Spongistatin 4 Cinachyrolide A Type: Other macrocyclic polyketide lactones. C61H93ClO20 Solid, mp 153–154 °C, [α]D22 = +23° (c = 0.2, MeOH). Source: Sponges Spirastrella spinispirulifera (the southest coast of Africa) and Cinachyra sp. (Japan waters). Pharm: Cytotoxic (in vitro NCI’s primary screen assay, mean panel GI50 = 1.02 × 10−10 mol/L, compare correlation coefficient = 0.93); cytotoxic (murine leukemia L1210 cells, IC50 < 0.6 ng/mL). Ref: N. Fusetani, et al, JACS, 1993, 115, 3977│G. R. Pettit, et al, J. Chem. Soc., Chem. Commun., 1993, 1805│G. R. Pettit, et al, Nat. Prod. Lett., 1993, 3, 239

O HO

O

OH H

O O

O

O

H HO

O O OH

O

HO

O O

Cl

O

OH

OH

OH

234

1 Polyketides

583 Spongistatin 5 Type: Other macrocyclic polyketide lactones. C59H89ClO19 mp 186–187 °C, [α]D22 = −11.1° (c = 0.2, MeOH). Source: Sponge Spirastrella spinispirulifera (southest coast of Africa). Pharm: Cytotoxic (in vitro NCI’s primary screen assay, mean panel GI50 = 1.23 × 10−10 mol/L, compare correlation coefficient = 0.92). Ref: G. R. Pettit, et al, J. Chem. Soc., Chem. Commun., 1993, 1805│G. R. Pettit, et al, Nat. Prod. Lett., 1993, 3, 239 O

O HO

O O

H

H

O O

O HO

HO O OH

O

HO

O O

Cl

OH

OH

OH

584 Spongistatin 8 Type: Other macrocyclic polyketide lactones. C61H92O20 mp 158–159 °C, [α]D22 = −32° (c = 0.2, MeOH). Source: Sponge Spirastrella spinispirulifera. Pharm: Cytotoxic; glutamate-induced tubulin polymerization inhibitor (potent). Ref: G. R. Pettit, et al, Nat. Prod. Lett., 1993, 3, 239 O

O HO

O O

O

O

H

H

O

H

O

H

HO O

O OH

O

HO

O

H

O

H

OH

OH

OH

585 Spongistatin 9 Type: Other macrocyclic polyketide lactones. C61H91ClO20 mp 164–165 °C, [α]D22 = −33.3° (c = 0.1, MeOH). Source: Sponge Spirastrella spinispirulifera. Pharm:

1.33 Other Macrocyclic Polyketide Lactones

235

Cytotoxic; glutamate-induced tubulin polymerization inhibitor (potent). Ref: G. R. Pettit, et al, Nat. Prod. Lett., 1993, 3, 239 O

O HO

O O

O

O

H

H

O O

H

O

H

HO O

O HO

OH

O

H

Cl

O

H

OH

OH

OH

586 Superstolide A Type: Other macrocyclic polyketide lactones. C36H52N2O7 Amorph. solid, [α]D = +54.1° (MeOH). Source: Sponge Neosiphonia superstes (off New Caledonia). Pharm: Cytotoxic (hmn bronchopulmunary non-small-cell lung carcinoma NSCLC-N6-L16 cells, IC50 = 0.04 μg/mL; murine leukemia cells espressing resistance toward doxorubicine P388/Dox, IC50 = 0.02 μg/mL; murine leukemia P388 cells IC50 = 0.003 μg/mL; hmn nasopharyngeal carcinoma KB cells, IC50 = 0.02 μg/mL; hmn colon carcinoma HT29 cells, IC50 = 0.04 μg/mL); cytotoxic (P388, IC50 = 5 nmol/L; hmn nasopharyngeal KB, IC50 = 8 nmol/L; NSCLC-N6-L16 non-small cell lung carcinoma cell line, IC50 = 6 nmol/L). Ref: M. V. D’Auria, et al, JACS, 1994, 116, 6658│ M. V. D‘Auria, et al, JNP, 1994, 57, 1595│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) O O

H

NH2 O 25

O

H

H

24

OH

O

N H

O

587 Superstolide B Type: Other macrocyclic polyketide lactones. C36H50N2O6 Amorph. solid, [α]D = +47° (MeOH). Source: Sponge Neosiphonia superstes (deep water, New Caledonia). Pharm: Cytotoxic (KB, IC50 = 0.005 μg/mL; P388, IC50 = 0.003 μg/mL; non-small-cell lung carcinoma NSCLC-N6-L16, IC50 = 0.039 μg/mL). Ref: M. V. D’Auria, et al, JNP, 1994, 57, 1595

236

1 Polyketides

O O

H

NH2 O 25

O

H

24

H

O

N H

O

588 Tartrolone D Type: Other macrocyclic polyketide lactones. C44H68O14 Amorph. solid, [α]D25 = +11° (c = 0.2, MeOH). Source: Marine-derived streptomycete Streptomyces sp. MDG-014-17069 (sediment, Madagascarr). Pharm: Cytotoxic (MDA-MB-231, GI50 = 0.79 μmol/L, TGI = 3.41 μmol/L, LC50 = 11.0 μmol/L; A549, GI50 = 0.16 μmol/L, TGI = 1.46 μmol/L, LC50 = 8.05 μmol/L; HT29, GI50 = 0.31 μmol/L, TGI = 1.71 μmol/L, LC50 = 8.41 μmol/L; control Doxorubicin: MDA-MB-231, GI50 = 0.02 μmol/L, TGI = 0.12 μmol/L, LC50 = 0.86 μmol/L; A549, GI50 = 0.08 μmol/L, TGI = 0.17 μmol/L, LC50 = 0.35 μmol/L; HT29, GI50 = 0.07 μmol/L, TGI = 0.33 μmol/L, LC50 > 17.2 μmol/L). Ref: M. Pérez, et al, JNP, 2009, 72, 2192

OH O

O

O H

O

OH OH

HO HO

O

H O O

O

OH

589 Tedanolide Type: Other macrocyclic polyketide lactones. C32H50O11 Cryst. (C6H6/CHCl3), mp 193–194 °C (dec), [α]D = +18.7° (c = 0.08, CHCl3). Source: Sponges Candidaspongia sp. (Papua New Guinea), Tedania ignis and Mycale sp. Pharm: Cytotoxic (melanoma UACC-257, IC50 = (5.9 ± 0.1)nmol/L; melanoma LOX-IMVI, IC50 = (2.5 ± 0.4)nmol/L; melanoma M14, IC50 = (8.6 ± 2.4)nmol/L; MCF7, IC50 = (3.6 ± 0.3)nmol/L; NCI-H460, IC50 = (7.0 ± 3.9)nmol/L). Ref: F. J. Schmitz, et al, JACS, 1984, 106, 7251│ J. R. Dunetz, et al, JACS, 2008, 130, 16407│E. L. Whitson, et al, Org. Lett., 2011, 13, 3518

1.33 Other Macrocyclic Polyketide Lactones

237

OH OH

O

H

17

O

O

O

O

13

OH

O

OH

O

590 Tolytoxin Type: Other macrocyclic polyketide lactones. C46H75NO13 Amorph. solid. Source: Cyanobacteria Tolypothrix conglutinata var. colorata and Scytonema spp. Pharm: Antileukemic; antifungal; cytotoxic; LD50 (mus, ipr) = 1.5 mg/kg. Ref: S. Carmeli, et al, JNP, 1990, 53, 1533 H O

N

O 34

H

O

O

O

27

16

O H

O OH

O

23

7

O

OH

6S

O

O

591 Tulearin A Type: Other macrocyclic polyketide lactones. C31H53NO6 Oil, [α]D23 = −45° (c = 0.17, CHCl3). Source: Sponge Fascaplysinopsis sp. (Salary Bay, Tulear, Madagascar). Pharm: Cytotoxic (MTT assay, K562, InRt = 65%; UT7, InRt = 32%). Ref: A. Bishara, et al, Org. Lett., 2008, 10, 153│A. Bishara, et al, Tet. Lett., 2009, 50, 3820

3

OH 8

O H 2N

O O

OH

O

592 Zampanolide Type: Other macrocyclic polyketide lactones. C29H37NO6 Amorph. solid, [α]D29 = −101° (c = 0.1, CH2Cl2). Source: Sponges Cacospongia mycofijiensis (‘Eua, Tonga) and Fasciospongia rimosa (Cape Zampa, Okinawa), Pharm: Cytotoxic (P388; A549; HT29;

238

1 Polyketides

MEL28 cell line; IC50 = 1–5 ng/mL). Ref: J. Tanaka, et al, Tet. Lett., 1996, 37, 5535│ A. B. Smith III, et al, JACS, 2001, 123, 12426│J. J. Field, et al, JMC, 2009, 52, 7328

O

O HO H O O

O

N H

593 Zooxanthellatoxin A Type: Other macrocyclic polyketide lactones. C140H233NO57S Amorph. solid + 18H2O (Na salt), mp 125–127 °C (Na salt), [α]D24 = +10° (c = 0.1, MeOH). Source: Dinoflagellate Symbiodinium sp. Y-6 from marine acoel flatworm Amphiscolops sp. Pharm: Vasoconstrictor. Ref: H. Nakamura, et al, JACS, 1995, 117, 550│ H. Nakamura, et al, Tet. Lett., 1995, 36, 7255

HO

OH

OH

OH

OH

OH

OH

OH

O

O

O H

HO

OH

O S O H

O O

OH

OH

OH

O OH

OH

OH

OH

OH

HO HO OH

OH

OH

O

O OH OH

OH

O

OH

OH HO

OH

OH HO

OH

O

OH O OH

OH O OH HO

OH OH

OH

OH

NH

OH

1.34 Bicyclic Polyketides

239

594 Zooxanthellatoxin B Type: Other macrocyclic polyketide lactones. C138H231NO56S mp 127–129 °C (Na salt), [α]D24 = +6.6° (c = 0.2, MeOH) (Na salt). Source: Dinoflagellate Symbiodinium sp. Y-6 from marine acoel flatworm Amphiscolops sp. Pharm: Vasoconstrictor. Ref: H. Nakamura, et al, JACS, 1995, 117, 550│H. Nakamura, et al, Tet. Lett., 1995, 36, 7255

HO

OH

OH

OH

O

OH

OH

OH

OH

O

O H

HO

OH

O S O

HO

O O

OH

O OH

HO

OH

OH

OH

OH

OH H

OH OH

OH

OH OH

O

O

HO

OH

O

OH

OH HO

OH

OH HO

H

O

OH O OH

OH

NH

O

O OH HO

OH

OH

OH

OH

1.34 Bicyclic Polyketides 595 Ascochlorin Type: Bicyclic polyketides. C23H29ClO4 Needles (Me2CO/hexane), mp 153–154 °C (dec), mp 172–173 °C, [α]D25 = −31° (c = 0.99, MeOH), [α]D25 = −35.8° (c = 0.50, MeOH). Source: Marine-derived fungus Acremonium sp. from sponge Stelletta sp. (Korea waters). Pharm: Anti-inflammatory (100 μmol/L, NO and TNF-R production inhibitor); antiviral; antibiotic. Ref: P. Zhang, et al, JNP, 2009, 72, 270 O

OH O

H OH Cl

240

1 Polyketides

596 Aspermytin A Type: Bicyclic polyketides. C16H26O3 [α]D25 = +1.2° (c = 0.1, CHCl3). Source: Marinederived fungus Aspergillus sp. (culture) from mussel Mytilus edulis. Pharm: Neurite outgrowth enhancer (50 μmol/L, rat pheochromocytoma PC12 cells). Ref: S. Tsukamoto, et al, BoMCL, 2004, 14, 417│ M. Saleem, et al, NPR, 2007, 24, 1142 (rev) H

OH

H O

OH

597 Cylindrol B Type: Bicyclic polyketides. C23H30O4 Amorph. powder, [α]D23 = −11.9° (c = 0.8, MeOH), [α]D25 = −27.8° (c = 0.38, MeOH). Source: Marine-derived fungus Acremonium sp. from sponge Stelletta sp. (Korea waters). Pharm: Farnesyl-protein transferase inhibitor. Ref: P. Zhang, et al, JNP, 2009, 72, 270 OH

O

O

H OH

598 Decumbenone C Craterellon C Type: Bicyclic polyketides. C16H26O5 Source: Marine-derived fungus Aspergillus sulphureus (sediment, location unspecified), terrestrial fungus (Craterellus odoratus). Pharm: Cytotoxic (SK-MEL-5 hmn melanoma cells, potent). Ref: O. I. Zhuravleva,et al, Arch. Pharmacal Res., 2012, 35, 1757│H. Guo, et al, Nat. Prod. Bioprospect., 2012, 2, 170 OH O OH OH

H OH

599 Dehydroxychlorofusarielin B 2-Chloro-2-deoxyfusarielin B Type: Bicyclic polyketides. C25H39ClO4 Cryst. (hexane/ Me2CO), [α]D20 = −125° (c = 0.4, MeOH). Source: Marine-derived fungus Aspergillus sp. from brown alga Sargassum horneri (surface, Korea). Pharm: Antibacterial

1.34 Bicyclic Polyketides

241

(Staphylococcus aureus, MIC = 62.5 μg/mL; MRSA, MIC = 62.5 μg/mL; MDRSA, MIC = 62.5 μg/mL, moderate). Ref: H. P. Nguyen, et al, JNP, 2007, 70, 1188

OH

HO

H

Cl 2

HO

H

O

600 Dinorspiculoic acid Dinorspiculoic acid A Type: Bicyclic polyketides. C25H32O3 Oil, [α]D24 = +65.4° (c = 0.09, CH2Cl2). Source: Sponge Plakortis zyggompha. Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC90 = 50 μg/mL). Ref: F. Berrué, et al, JNP, 2005, 68, 547│F. Berrue, et al, Tetrahedron, 2007, 63, 2328 H O H O

OH

601 Fusarielin A Type: Bicyclic polyketides. C25H38O4 Powder, mp 68–72 °C, [α]D25 = −132° (c = 0.1, MeOH). Source: Marine-derived fungi Fusarium tricinctum MFB392-2 and Fusarium sp. 95F858, terrestrial fungus (Fusarium sp. K432). Pharm: Antibacterial (Staphylococcus aureus, MIC = 32.5 μg/mL; MRSA, MIC = 32.5 μg/mL; MDRSA, MIC = 62.5 μg/mL, moderate); antifungal. Ref: H. P. Nguyen, et al, JNP, 2007, 70, 1188

HO

H O H

O

OH

242

1 Polyketides

602 Fusarielin B Type: Bicyclic polyketides. C25H40O5 Powder, mp 138–140 °C, [α]D = −100° (c = 0.1, MeOH). Source: Marine-derived fungus Fusarium sp. 05JANF165, terrestrial fungus (Fusarium sp. K432). Pharm: Antibacterial (Staphylococcus aureus, MIC = 62.5 μg/mL; MRSA, MIC = 62.5 μg/mL; MDRSA, MIC = 62.5 μg/mL, moderate); antifungal. Ref: H. Kobayashi, et al, J. Antibiot., 1995, 48, 42│H. P. Nguyen, et al, JNP, 2007, 70, 1188

HO

OH

H

HO 2

HO

H

O

603 Fusarielin E Type: Bicyclic polyketides. C25H39ClO4 Source: Marine-derived fungus Fusarium sp. (undisclosed origin). Pharm: Conidia growth inhibitor (Pyricularia oryzae, by swelling effect and induced curling deformation of mycelia). Ref: Y. Gai, et al, Chin. Chem. Lett., 2007, 18, 954

HO

OH

H

Cl 2

HO

H

O

604 10-Hydroxy-18-O-methylbetaenone C Type: Bicyclic polyketides. C22H36O6 Powder, [α]D = +16.6° (c = 1.25, EtOH). Source: Marine-derived fungus Microsphaeropsis sp. from sponge Aplysina aerophoba (Mediterranean Sea). Pharm: Kinases inhibitor (PKC-ε, IC50 = 36.0 μmol/L; CDK4/ cyclin D1, IC50 = 11.5 μmol/L; and EGFR, IC50 = 10.5 μmol/L). Ref: G. Brauers, et al, JNP, 2000, 63, 739

1.34 Bicyclic Polyketides

243

O

O 15 12

H

H 4 2

10

HO

OH

O

21

OH

605 Ilicicolin C Type: Bicyclic polyketides. C23H31ClO4 Cryst. (Me2CO/hexane), mp 130–131 °C, [α]D25 = +6° (c = 1, MeOH), [α]D25 = +5.24° (c = 0.20, MeOH). Source: Marine-derived fungus Acremonium sp. from sponge Stelletta sp. (Korea waters). Pharm: Antiinflammatory (100 μmol/L, selective NO production inhibitor). Ref: P. Zhang, et al, JNP, 2009, 72, 270 O

OH O

H OH Cl

606 Iso-9,10-deoxytridachione Type: Bicyclic polyketides. C22H30O3 Oil, [α]D = +5.9° (CHCl3). Source: Sacoglossan Elysia timida (Mediterranean Sea). Pharm: Ichthyotoxin. Ref: M. Gavagnin, et al, JNP, 1994, 57, 298 O O

O

607 LL-Z 1272 ε Type: Bicyclic polyketides. C23H32O4 [α]D25 = +3.86° (c = 0.50, MeOH). Source: Marine-derived fungus Acremonium sp. from sponge Stelletta sp. (Korea waters). Pharm: Anti-inflammatory (100 μmol/L, selective NO production inhibitor). Ref: S. B., Singh, et al, JOC, 1996, 61, 7727│P. Zhang, et al, JNP, 2009, 72, 270 O

OH O

H OH

244

1 Polyketides

608 24-Norisospiculoic acid Type: Bicyclic polyketides. C26H34O3 Oil, [α]D24 = +41.5° (c = 0.05, CHCl3). Source: Sponge Plakortis zyggompha. Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC90 = 50 μg/mL). Ref: F. Berrué, et al, Tetrahedron, 2007, 63, 2328 H O H O

OH

609 Norspiculoic acid A Type: Bicyclic polyketides. C26H34O3 Oil, [α]D24 = +147.8° (c = 0.11, CH2Cl2). Source: Sponge Plakortis zyggompha. Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC90 = 50 μg/mL). Ref: F. Berrué, et al, JNP, 2005, 68, 547│F. Berrue, et al, Tetrahedron, 2007, 63, 2328

H O H O

OH

610 Spiculoic acid A Type: Bicyclic polyketides. C27H36O3 Oil, [α]D = +110° (c = 0.1, CH2Cl2). Source: Sponge Plakortis angulospiculatus. Pharm: Cytotoxic (hmn breast cancer MCF7 cells, IC50 = 8 μg/mL). Ref: X. -H. Huang, et al, Org. Lett., 2004, 6, 75

H O H O

OH

1.35 Tricyclic Polyketides 611 Akaeolide Type: Tricyclic polyketides. C22H32O6 Source: Marine-derived streptomycete Streptomyces sp. (sediment, Miyazaki Harbour, Japan). Pharm: Cytotoxic (3Y1 rat fibroblasts, modest). Ref: Y. Igarashi, et al, Org. Lett., 2013, 15, 5678

1.35 Tricyclic Polyketides

245

O

O

O

O

O OH

612 Daporine Type: Tricyclic polyketides. C30H22O14 Source: Marine fungus Diaporthe sp. (endophytic). Pharm: Antineoplastic (in both cellular in vitro and animal models in vivo, induces conversion of tumour associated macrophages from M2 to M1 phenotype). Ref: H. C. Wu, et al, Org. Biomol. Chem., 2014, 12, 6545

O O

OH

O OH O

O

O O

OH

O

OH

O

O

613 Discodermide Type: Tricyclic polyketides. C27H34N2O6 mp 200 °C (dec), [α]D = +97.5° (c = 0.2, CHCl3/MeOH). Source: Lithistid sponge Discodermia dissoluta. Pharm: Antifungal; cytotoxic. Ref: S. P. Gunasekera, et al, JOC, 1991, 56, 4830

O

H

H N H

H

O H O

O OH N H OH

614 Herbarone Type: Tricyclic polyketides. C16H20O6 Off-white amorph. powder, [α]D15 = +10° (c = 0.04, MeOH). Source: Marine-derived fungus Torula herbarum from sea hare Notarchus leachii (Beibuwan Bay, Guangxi, China). Pharm: Cytotoxic (MG63, LoVo, and A549 cells, IC50 > 97.4 μmol/L, control Adriamycin, IC50 = 2.7 μmol/L). Ref: W. -L. Geng, et al, JNP, 2012, 75, 1828

246

1 Polyketides

O H

O

OH OH

O HO

615 Indoxamycin A Type: Tricyclic polyketides. C22H30O3 Oil, [α]D = −5.1° (c = 0.1, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS-643 (sediment, Kochi Harbour, Japan). Pharm: Cytotoxic (HT29 cells, IC50 = 0.59 μmol/L). Ref: S. Sato, et al, JOC, 2009, 74, 5502 O

H 4''

OH 10 6

O H

3''

7 11

616 Indoxamycin B Type: Tricyclic polyketides. C22H30O4 Oil, [α]D20 = −49.2° (c = 0.1, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS-643 (sediment, Kochi Harbour, Japan). Pharm: Cytotoxic (HT29 cells, IC50 > 3 μmol/L). Ref: S. Sato, et al, JOC, 2009, 74, 5502│O. F. Jeker, et al, Angew. Chem., Int. Ed., 2012, 51, 3474 (structure revised) H

OH

O COOH

617 Indoxamycin C Type: Tricyclic polyketides. C22H30O4 Oil, [α]D = −20.5° (c = 0.08, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS-643 (sediment, Kochi Harbour, Japan). Pharm: Cytotoxic (HT29 cells, IC50 > 3 μmol/L). Ref: S. Sato, et al, JOC, 2009, 74, 5502 H COOH

4'' 10

O 3''

6

H HO

7 11

1.35 Tricyclic Polyketides

247

618 Indoxamycin D Type: Tricyclic polyketides. C22H30O4 Oil, [α]D = −36.9° (c = 0.1, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS-643 (sediment, Kochi Harbour, Japan). Pharm: Cytotoxic (HT29 cells, IC50 > 3 μmol/L). Ref: S. Sato, et al, JOC, 2009, 74, 5502

OH

H COOH

4'' 10

O

6

H

3''

7 11

619 Indoxamycin E Type: Tricyclic polyketides. C22H30O4 Oil, [α]D = −30.6° (c = 0.1, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS-643 (sediment, Kochi Harbour, Japan). Pharm: Cytotoxic (HT29 cells, IC50 > 3 μmol/L). Ref: S. Sato, et al, JOC, 2009, 74, 5502

H COOH

4'' 10

O OH

6

H

7 11

3''

620 Indoxamycin F Type: Tricyclic polyketides. C22H30O4 Oil, [α]D = −55.8° (c = 0.1, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS-643 (sediment, Kochi Harbour, Japan). Pharm: Cytotoxic (HT29 cells, IC50 = 0.31 μmol/L). Ref: S. Sato, et al, JOC, 2009, 74, 5502

H COOH

4'' 6S

O 3''

H

7 11

10

OH

621 23-Norspiculoic acid B Type: Tricyclic polyketides. C35H32O2 Amorph. solid, [α]D25 = −18° (c = 0.23, CH2Cl2). Source: Sponge Plakortis angulospiculatus. Pharm: Anti-inflammatory. Ref: S. Ankisetty, et al, JNP, 2010, 73, 1494

248

1 Polyketides

H

H O

OH

622 Shimalactone A Type: Tricyclic polyketides. C29H40O4 Oil, [α]D23 = +12° (c = 0.57, MeOH). Source: Marine-derived fungus Emericella variecolor GF10 from sediment sample (Japan waters). Pharm: Neuritogenesis inducer (neuroblastoma neuro2a cells, 10 μg/mL); cytotoxic ( > 10 μg/mL). Ref: H. Wei, et al, Tetrahedron, 2005, 61, 8054

O

O

O 10 15

9 16

H HO

623 Shimalactone B Type: Tricyclic polyketides. C29H40O4 Oil, [α]D23 = −48° (c = 1.5, MeOH). Source: Marine-derived fungus Emericella variecolor GF10 from sediment sample (Japan waters). Pharm: Neuritogenesis inducer (neuroblastoma neuro2a cells, 10 μg/mL); cytotoxic ( > 10 μg/mL). Ref: H. Wei, et al, Heterocycles, 2006, 68, 111

O

O

O 10 15

9 16

H HO

624 Trichodermaketone A Type: Tricyclic polyketides. C16H24O5 Oil, [α]D20 = +73° (c = 0.17, MeOH). Source: Marine-derived fungus Trichoderma koningii MF349 (marine mud, South China Sea). Pharm: Antifungal (Candida albicans SC5314, 125 μg/mL with 0.05 μg/mL ketoconazole). Ref: F. Song, et al, JNP, 2010, 73, 806

1.36 Tetra-and Higher-cyclic Polyketides

249

OH H

O

OH 7

O

H

O

8 9 10

1.36 Tetra-and Higher-cyclic Polyketides 625 Portimine Type: Tetra-and higher-cyclic polyketides. C23H31NO5 Source: Dinofiagellate Vulcanodinium rugosum (benthic, Northland, New Zealand). Pharm: Cytotoxic (P388, potent). Ref: A. I. Selwood, et al, Tetrahedron Lett., 2013, 54, 4705

HO

N H O O

H O OH

2 Steroids 2.1 Pregnane Steroids (C21) 626 Astrosterioside C Type: Pregnane steroids. C55H88O31S Source: Starfish Astropecten monacanthus (extracts, Cat Ba I., Haiphong, Vietnam). Pharm: IL-6 production inhibitor (stimulated bone marrow-derived dendritic cells, mild). Ref: N. P. Thao, et al, JNP, 2013, 76, 1764 O H H HO O

O S

H O O

HO

HO

HO

O

O

HO

O

O

O

O

O OH

O O

OH O

OH OH

HO

H

OH OH OH

OH O OH

627 3,4-Dihydroxypregna-5,15-diene-20-one-19,2-carbolactone Type: Pregnane steroids. C21H26O5 [α]D = −130° (c = 1.5, CHCl3). Source: Sponge Strongylophora sp. (Hawaii). Pharm: Cytotoxic (KB, MIC = 1 μg/mL, LoVo, MIC = 5 μg/mL). Ref: J. M. Corgiat, et al, Tetrahedron, 1993, 49, 1557

O O O

HO OH

https://doi.org/10.1515/9783110653922-002

252

2 Steroids

628 3α,16β-Dihydroxy-5α-pregna-1,20-diene-3,16-diacetate Type: Pregnane steroids. C25H36O4 Oil, [α]D21 = +133.0° (c = 0.53, CHCl3). Source: Soft coral Capnella thyrsoidea (Two variants, South Africa). Pharm: Stimulates superoxide production (rbt neutrophils, cytotoxic due to the cell lysis increases superoxide level). Ref: G. J. Hooper, et al, Tetrahedron, 1995, 51, 9973

H H

O O

O O

H

629 Forbeside E3 (3β,5α,6α)-3,6-Dihydroxypregn-9(11)-en-20-one 6-O-(6-deoxy-β-D-glucopyranoside) 3-O-sulfate Type: Pregnane steroids. C27H42O10S Powder (Na salt), mp 206 °C (Na salt), [α]D28 = −3.5° (c = 0.004, H2O), [α]D = +20.9° (c = 0.33, MeOH). Source: Starfishes Asterias forbesi and Aphelasterias japonica. Pharm: Hemolytic. Ref: J. A. Findlay, et al, JNP, 1990, 53, 710│Z.-H. Jiang, et al, Liebigs Ann. Chem., 1993, 1179 O H H O HO

S

O

O

H O O OH OH

OH

630 16β-Hydroxy-5α-pregna-1,20-dien-3-one-16-acetate Type: Pregnane steroids. C23H32O3 Oil, [α]D21 = +91° (c = 0.58, CHCl3). Source: Soft coral Capnella thyrsoidea (Two variants, South Africa). Pharm: Stimulates superoxide production (rbt neutrophils, cytotoxic due to the cell lysis increases superoxide level). Ref: G. J. Hooper, et al, Tetrahedron, 1995, 51, 9973

H H

O O

O

H

2.1 Pregnane Steroids (C21)

253

631 Pregnenolone 3β-Hydroxypregn-5-en-20-one Type: Pregnane steroids. C21H32O2 Colorless gum, mp 192–194 °C, [α]D25 = +28.5° (c = 1.00, EtOH). Source: Sponge Haliclona rubens, soft corals Lobophytum sp., Sarcophyton crassocaule and Lobophytum laevigatum (Khanh Hoa province, Vietnam), several plant and animal spp. Pharm: Cytotoxic (P388, ED50 = 7.8 μg/mL; KB, ED50 > 50 μg/mL; A549, ED50 = 8.6 μg/mL; HT29, ED50 = 0.7 μg/mL); upregulats PPARs transcription (HepG2, dose-dependent). Ref: J. A. Ballantine, et al, Tet. Lett., 1977, 1547│S. R. Ammanamanchi, et al, JNP, 2000, 63, 112│J. H. Sheu, et al, JNP, 2000, 63, 149│T. H. Quang, et al, BoMCL, 2011, 21, 2845 O H H

HO

632 Sclerosteroid A Type: Pregnane steroids. C23H36O3 Source: Soft coral Scleronephthya gracillimum (Green I., Taiwan). Pharm: Anti-inflammatory (Inhibits expression of pro-inflammatory proteins iNOS and COX-2 in stimulated macrophages). Ref: H. -Y. Fang, et al, Tetrahedron, 2012, 68, 9694 O H O

H H

HO

H

H

633 Sclerosteroid B Type: Pregnane steroids. C23H38O4 Source: Soft coral Scleronephthya gracillimum (Green I., Taiwan). Pharm: Anti-inflammatory (Inhibits expression of pro-inflammatory proteins iNOS and COX-2 in stimulated macrophages). Ref: H. -Y. Fang, et al, Tetrahedron, 2012, 68, 9694 O H O

H

O

H O

H

H

254

2 Steroids

634 Sclerosteroid E Type: Pregnane steroids. C22H35O4 Source: Soft coral Scleronephthya gracillimum (Green I., Taiwan). Pharm: Anti-inflammatory (Inhibits expression of pro-inflammatory proteins iNOS and COX-2 in stimulated macrophages). Ref: H. -Y. Fang, et al, Tetrahedron, 2012, 68, 9694

H HO

O

O

H H

O

H

H

635 3-(4-O-Acetyl-6-deoxy-β-galactopyranosyloxy)-19-norpregna-1,3,5(10), 20-tetraene Type: 19-Norpregnane steroids. C28H38O6 [α]D22 = −96.5° (c = 0.055, CH2Cl2). Source: Soft coral Alcyonium gracillimum (Japan waters). Pharm: Antifoulant (barnacle Balanus Amphitrite (cyprid larvae), LD100 = 100 μg/mL). Ref: Y. Tomono, et al, JNP, 1999, 62, 1538

O O

H O O

HO OH

636 3-Methoxy-19-norpregna-1,3,5(10),20-tetraene Type: 19-Norpregnane steroids. C21H28O [α]D22 = +19.9° (c = 0.2). Source: Soft coral Alcyonium gracillimum (Japan waters). Pharm: Antifoulant (barnacle Balanus Amphitrite (cyprid larvae), LD100 = 100 μg/mL). Ref: Y. Tomono, et al, JNP, 1999, 62, 1538

H H

O

637 19-Norpregna-1,3,5(10),20-tetraen-3-O-α-fucopyranoside Type: 19-Norpregnane steroids. C26H36O5 Amorph. solid, [α]D25 = +47° (c = 0.26, MeOH). Source: Soft coral Scleronephthya pallida (Thailand). Pharm: Antimalarial

2.2 Cholan-24-oic acid Steroids

255

(inhibits growth of malarial protozoa Plasmodium falciparum, EC50 = 1.5 μg/mL); cytotoxic (breast carcinoma cell line BCA-1, ED50 = 10 μg/mL). Ref: P. Kittakoop, et al, JNP, 1999, 62, 318

H HO

O

HO

O OH

2.2 Cholan-24-oic acid Steroids 638 (20S,22E )-3-Oxochola-1,4,22-trien-24-oic acid methyl ester Type: Cholan-24-oic acid steroids. C25H34O3 [α]D22 = +53.6° (c = 0.28, CH2Cl2). Source: Soft corals Alcyonium gracillimum and Dendronephthya sp. (Japan waters). Pharm: Antifoulant (barnacle Balanus Amphitrite (cyprid larvae), LD100 = 100 μg/mL). Ref: Y. Tomono, et al, JNP, 1999, 62, 1538 O O

H H

O

639 3-Oxochol-4-en-24-oic acid Type: Cholan-24-oic acid steroids. C24H36O3 Cryst. (EtOH) or white solid, mp 185–187.5 °C, [α]D20 = +46.7° (c = 0.30, EtOH). Source: Soft coral Eleutherobia sp., stony coral Deltocyathus magnificus, nudibranch Aldisa sanguinea cooperi. Pharm: Ichthyotoxin; antifeedant (steroidal feeding inhibitor). Ref: S. W. Ayer,et al, Tetrahedron Lett. 1982, 23, 1039│A. Guerriero,et al, Helv. Chim.Acta 1996, 79, 982│S. C. Lievens, et al, JNP, 2004, 67, 2130 O H H

O

OH

256

2 Steroids

640 Solomonsterol A Type: Cholan-24-oic acid steroids. C24H42O12S3 Source: Lithistid sponge Theonella swinhoei (Solomon Is.). Pharm: PXR agonists (potent). Ref: C. Festa, et al, JMC, 2011, 54, 401│R. Teta, et al, Mar. Drugs, 2012, 10, 1383 O

OH

H

O S O

H

O H

O HO

O

S O

S O OH

H

H

O

641 Solomonsterol B Type: Cholan-24-oic acid steroids. C23H40O12S3 Source: Lithistid sponge Theonella swinhoei (Solomon Is.). Pharm: PXR agonists (potent). Ref: C. Festa, et al, JMC, 2011, 54, 401│R. Teta, et al, Mar. Drugs, 2012, 10, 1383

O OH

H

O S O

S OH O

H

O O HO

O

H

S O

H

H

O

2.3 Cholestane Steroids (C27) 642 Acalycigorgia inermis sterol A Type: Cholestane steroids. C29H46O5 Amorph. solid, mp 183–185 °C, [α]D25 = −28.3° (c = 0.1, MeOH). Source: Gorgonian Acalycigorgia inermis (Korea waters). Pharm: Cytotoxic (K562, LC50 = 1.1 μg/mL). Ref: J. -R. Rho, et al, Bull. Korean Chem. Soc., 2000, 21, 518 O

H H

HO

OH

O

O

2.3 Cholestane Steroids (C27)

257

643 Acalycigorgia inermis sterol B (3β,5α,25ξ )-3,5-Dihydroxy-26-acetoxy-cholestan-6-one Type: Cholestane steroids. C29H48O5 Amorph. solid, [α]D25 = −6.1° (c = 0.4, MeOH). Source: Gorgonian Acalycigorgia inermis (Korea waters). Pharm: Cytotoxic (K562, LC50 = 0.9 μg/mL). Ref: J. -R. Rho, et al, Bull. Korean Chem. Soc., 2000, 21, 518 O

H O

H

HO

OH

O

644 Acalycigorgia inermis sterol C Type: Cholestane steroids. C28H46O5 mp 202–205 °C, [α]D25 = −28.3° (c = 0.1, MeOH). Source: Gorgonian Acalycigorgia inermis (Korea waters). Pharm: Cytotoxic (K562, LC50 = 9.7 μg/mL). Ref: J. -R. Rho, et al, Bull. Korean Chem. Soc., 2000, 21, 518 H O

H

HO

OH

O

O

645 Acanthifolioside C Type: Cholestane steroids. C32H52O7 White amorph. solid, [α]D20 = −25.0° (c = 0.14, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Cytotoxic (L-6, IC50 = 31.9 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L); antiprotozoal (Trypanosoma brucei rhodesiense, IC50 = 32.3 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 30.6 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L; Leishmania donovani, IC50 = 7.5 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L; Plasmodium falciparum, IC50 = 8.8 μmol/L, control Chloroquine, IC50 = 0.20 μmol/L). Ref: E. L. Regalado, et al, Tetrahedron, 2011, 67, 1011

H H H HO

OH H

O

OH

HO O

OH

258

2 Steroids

646 12β-Acetoxycholest-4-ene-3,24-dione Type: Cholestane steroids. C29H44O4 Amorph. powder, [α]D25 = +68.7° (c = 0.1, CHCl3). Source: Gorgonian Dasystenella acanthina (psychrophilic, cold water, Antarctic). Pharm: Cytotoxic (DU145, GI50 = 4.2 μg/mL; LNCaP, GI50 = 1.6 μg/mL; IGROV, GI50 = 4.4 μg/mL; SKBR3, GI50 = 3.5 μg/mL; SK-MEL-28, GI50 = 3.6 μg/mL; A549, GI50 = 4.9 μg/mL; K562, GI50 = 1.6 μg/mL; PANC1, GI50 = 3.3 μg/mL; HT29, GI50 = 4.3 μg/mL; LoVo, GI50 = 2.0 μg/mL; LoVo-DOX, GI50 = 1.5 μg/mL; HeLa, GI50 = 3.4 μg/mL; cell growth inhibitor). Ref: G. G. Mellado, et al, Steroids, 2004, 69, 291│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O

O O

24

H H H

H

O

647 3α-Acetoxy-25-hydroxycholest-4-en-6-one Type: Cholestane steroids. C29H46O4 Amorph. powder, [α]D25 = +76.5° (c = 0.06, CHCl3). Source: Gorgonian Dasystenella acanthina (psychrophilic, cold water, Antarctic). Pharm: Cytotoxic (DU145, GI50 = 2.6 μg/mL; LNCaP, GI50 = 1.6 μg/mL; IGROV, GI50 = 2.1 μg/mL; SKBR3, GI50 = 3.0 μg/mL; SK-MEL-28, GI50 = 1.5 μg/mL; A549, GI50 = 3.8 μg/mL; K562, GI50 = 1.4 μg/mL; PANC1, GI50 = 2.1 μg/mL; HT29, GI50 = 2.2 μg/mL; LoVo, GI50 = 2.1 μg/mL; LoVo-DOX, GI50 = 2.9 μg/mL; HeLa, GI50 = 2.6 μg/mL; growth inhibitor). Ref: G. G. Mellado, et al, Steroids, 2004, 69, 291│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

H

24

OH

H O

H

H

O O

648 2-O-Acetylpinnasterol Type: Cholestane steroids. C29H44O6 Cryst., mp 105–107 °C, [α]D = +64° (MeOH). Source: Red alga Laurencia pinnata. Pharm: Moulting hormone activity. Ref: A. Fukuzawa, et al, Tet. Lett., 1981, 22, 4085

2.3 Cholestane Steroids (C27)

259

OH OH O O HO O

649 Agosterol A (3β,4β,5α,6α,11α,22R)-Cholest-7-ene-3,4,6-triacetoxy-11,22-diol Type: Cholestane steroids. C33H52O8 Amorph. solid, [α]D = +27.3° (c = 0.1, MeOH). Source: Sponge Spongia sp. (Japan waters). Pharm: Reversal of MDR (3 μg/mL: KB-C2, InRt = (88 ± 3)%; KB-CV60, InRt = (80 ± 2)%; KB-3-1, InRt = (5 ± 4)%). Ref: S. Aoki, et al, Tet. Lett., 1998, 39, 6303│S. Aoki, et al, Tetrahedron, 1999, 55, 13965│N. Murakami, et al, Chem. Eur. J., 2001, 7, 2663 OH H

HO O O O

O

O

O

650 Agosterol B Type: Cholestane steroids. C31H50O7 [α]D = −5.5° (c = 0.1, CHCl3). Source: Sponge Spongia sp. (Japan waters). Pharm: Reversal of MDR (3 μg/mL: KB-C2, InRt = (38 ± 10)%; KB-CV60, InRt = (77 ± 4)%; KB-3-1, InRt = (8 ± 5)%). Ref: S. Aoki, et al, Tetrahedron, 1999, 55, 13965 OH

HO

H

O O O

O

H

OH

651 Agosterol C Type: Cholestane steroids. C31H50O6 [α]D = +49.5° (c = 0.7, CHCl3). Source: Sponge Spongia sp. (Japan waters). Pharm: Reversal of MDR (10 μg/mL: KB-C2,

260

2 Steroids

InRt = (12 ± 11)%; KB-CV60, InRt = (8 ± 2)%; KB-3-1, InRt = (11 ± 6)%). Ref: S. Aoki, et al, Tetrahedron, 1999, 55, 13965 OH

H

HO O

O

H

O

O

652 Agosterol D2 Type: Cholestane steroids. C33H52O8 [α]D = +28.0° (c = 0.2, CHCl3). Source: Sponge Spongia sp. (Japan waters). Pharm: Reversal of MDR (10 μg/mL: KB-C2, InRt = (86 ± 3)%; KB-CV60, InRt = (73 ± 3)%; KB-3-1, InRt = (29 ± 9)%). Ref: S. Aoki, et al, Tetrahedron, 1999, 55, 13965 OH

OH

H

O O O

O

H

O

O

653 Amaranzole B Type: Cholestane steroids. C37H52N2O15S3 Source: Sponge Phorbas amaranthus (Dry Reef Rocks, Key Largo, Florida). Pharm: Antifeedant. Ref: B. I. Morinaka, et al, JOC, 2010, 75, 2453 O O O

OH O S O

O

O OH

N

H H H

O S

H N

H

O

OH H

S O

O OH

2.3 Cholestane Steroids (C27)

261

654 Amaranzole C Type: Cholestane steroids. C36H50N2O13S3 Source: Sponge Phorbas amaranthus (Dry Reef Rocks, Key Largo, Florida). Pharm: Antifeedant. Ref: B. I. Morinaka, et al, JOC, 2010, 75, 2453

N N OH O O S O O HO S O O

OH

H

H H

O

O S OH O

655 Amaranzole D Type: Cholestane steroids. C36H50N2O13S3 Source: Sponge Phorbas amaranthus (Dry Reef Rocks, Key Largo, Florida). Pharm: Antifeedant. Ref: B. I. Morinaka, et al, JOC, 2010, 75, 2453

N N

O

HO O

O S

OH O S

OH

H

O H O

H

O

S O

O OH

656 Amaranzole E Type: Cholestane steroids. C37H50N2O15S3 Source: Sponge Phorbas amaranthus (Dry Reef Rocks, Key Largo, Florida). Pharm: Antifeedant. Ref: B. I. Morinaka, et al, JOC, 2010, 75, 2453

262

2 Steroids

O

H N N

O

O

OH O S

OH

H

O H O O

S Oh

H O

O

S O

O OH

657 Amaranzole F Type: Cholestane steroids. C37H50N2O15S3 Source: Sponge Phorbas amaranthus (Dry Reef Rocks, Key Largo, Florida). Pharm: Antifeedant. Ref: B. I. Morinaka, et al, JOC, 2010, 75, 2453 O O

O

OH O S

H N N

OH

H

O H O O

S

H

O OH

O

S O

O OH

658 Amurensoside A (3β,5α,6α,15α,24S)-Cholestane-3,6,15,24-tetrol 24-O-β-D-xylopyranoside 15-O-sulfate Type: Cholestane steroids. C32H56O11S [α]D = +16.7° (MeOH). Source: Starfishes Asterias amurensis and Asterias rathbuni. Pharm: Cytostatic (cell division inhibitor, fertilized sea urchin eggs, IC100 = 1.9 × 10−4 mol/L). Ref: R. Riccio, et al, JCS Perkin I, 1988, 1337│N. V. Ivanchina, et al, JNP, 2001, 64, 945 O O OH OH

OH

H 15

6

HO

H

OH

O O S OH O

2.3 Cholestane Steroids (C27)

263

659 Anastomosacetal A (17α,20R,21R,24R)-21,24-Epoxy-17,21-dihydroxycholesta-1,4-dien-3-one Type: Cholestane steroids. C27H40O4 Solid, mp 134–136 °C, [α]D25 = +22.3° (c = 0.4, MeOH). Source: Gorgonian Euplexaura anastomosans. Pharm: Cytotoxic (P388, extract of Euplexaura anastomosans, LC50 = 73.3 μg/mL, compound inactive). Ref: Y. Seo, et al, JNP, 1996, 59, 1196

O

H

HO

OH

H

O

660 Archasteroside B (3β,5α,6α,16β,20S)-Cholest-9(11)-ene-3,6,16,20-tetrol 6-O-[6-deoxy-β-D-galactopyranosyl(1→2)-6-deoxy-β-D-glucopyranosyl-(1→4)-[6-deoxy-β-D-glucopyranosyl-(1→2)]-6-deoxyβ-D-glucopyranosyl-(1→3)-6-deoxy-β-D-glucopyranoside] 3-Sulfate Type: Cholestane steroids. C57H96O27S Amorph. powder, [α]D20 = +9.8° (c = 0.3, MeOH). Source: Starfish Archaster typicus (Quang Ninh, Vietnam). Pharm: Cytotoxic (HeLa, IC50 = 14 μmol/L; JB6 P+CI41, IC50 = 18 μmol/L). Ref: A. A. Kicha, et al, BoMCL, 2010, 20, 3826 OH H H O O

OH S

6

O

H OO O

O

OH OH OO OH

OO OH

OH

O O OH

HO

OH

OH

OH

OH

OH

264

2 Steroids

661 Asteriidoside A Type: Cholestane steroids. C63H104O33S [α]D = +5.9° (c = 1, MeOH). Source: An unidentified starfish (Asteriidae). Pharm: Cytotoxic (NSCLC-L16, IC50 > 30 μg/mL). Ref: S. De Marino, et al, JNP, 1998, 61, 1319

OH H

HO O

O

O S

O

H OO O

O OH BD-galap HO HO

OH

OH

OO OH

OO BD-galap OH HO OO HO OH O O HO OH OH OH BD-fucop OH

662 Asteriidoside C Type: Cholestane steroids. C62H102O31S [α]D = +10.7° (c = 1, MeOH). Source: An unidentified starfish (Asteriidae). Pharm: Cytotoxic (NSCLC-L16, IC50 = 19.7 μg/mL). Ref: S. De Marino, et al, JNP, 1998, 61, 1319 OH H

HO O

O S

O

H OO O

O OH HO OO BD-fucop O HO HO

OO

HO O OH

O

OH

OO OH

OH

OH OH BD-fucop BD-galap

OH

OH

2.3 Cholestane Steroids (C27)

265

663 Asteriidoside E (3β,5α,6α,20S)-Cholesta-9(11),24-diene-3,6,20-triol 6-O-[β-D-galactopyranosyl-(1→3)β-D-arabinopyranosyl-(1→2)-β-D-fucopyranosyl-(1→4)-[6-deoxy-β-D-glucopyranosyl(1→2)]-β-D-xylopyranosyl-(1→3)-6-deoxy-β-D-glucopyranoside] 3-O-sulfate Type: Cholestane steroids. C61H100O31S [α]D = +8.5° (c = 1, MeOH). Source: An unidentified starfish (Asteriidae). Pharm: Cytotoxic (NSCLC-L16, IC50 = 18.1 μg/mL). Ref: S. De Marino, et al, JNP, 1998, 61, 1319 OH H

HO O

O S

O

H OO O

BD-xylop

O

OH OH HO OO BD-fucop O

O

OH

O

OH OO OH HO

BD-arabp

OH

HO HO HO

O

O

OH

BD-galap OH

664 Asteriidoside F (3β,5α,6α,15β,16β,22E,25S)-Cholest-22-ene-3,6,8,15,16,26-hexol 3,26-di-O-β-D-xylopyranoside Type: Cholestane steroids. C37H62O14 [α]D = −8.3° (c = 1, MeOH). Source: An unidentified starfish (Asteriidae). Pharm: Cytotoxic (NSCLC-L16, IC50 > 30 μg/mL). Ref: S. De Marino, et al, JNP, 1998, 61, 1319 25S

H OH

OH OH

OO OH OH OH

H

OO

OH

15

OH OH

OH

266

2 Steroids

665 Asteriidoside I Type: Cholestane steroids. C37H62O17S [α]D = −8.8° (c = 1, MeOH). Source: An unidentified starfish (family Asteriidae, Antarctic). Pharm: Cytotoxic (NSCLC-L16, IC50 > 30 μg/mL). Ref: S. De Marino, et al, JNP, 1998, 61, 1319 OH HO

O

OH

O

H OH

HO

O

O O

HO

OH

O

S

OH

O

OH

OH

666 Astropectenol A Type: Cholestane steroids. C27H46O3 Source: Starfish Astropecten polyacanthus (Cat Ba I., Haiphong, Vietnam). Pharm: Cytotoxic (inactive or mild). Ref: N. P. Thao, et al, CPB, 2013, 61, 1044

H OH H

H

O HO

H H

667 Astropectenol B Type: Cholestane steroids. C27H44O4 Source: Starfish Astropecten polyacanthus (Cat Ba I., Haiphong, Vietnam). Pharm: Cytotoxic (inactive or mild). Ref: N. P. Thao, et al, CPB, 2013, 61, 1044

H

OH

H HO

O O

H

2.3 Cholestane Steroids (C27)

267

668 Astropectenol C Type: Cholestane steroids. C27H42O3 Source: Starfish Astropecten polyacanthus (Cat Ba I., Haiphong, Vietnam). Pharm: Cytotoxic (inactive or mild). Ref: N. P. Thao, et al, CPB, 2013, 61, 1044

H

O O

HO

H

669 Astropectenol D Type: Cholestane steroids. C27H46O2 Source: Starfish Astropecten polyacanthus (Cat Ba I., Haiphong, Vietnam). Pharm: Cytotoxic (inactive or mild). Ref: N. P. Thao, et al, CPB, 2013, 61, 1044

H OH H HO

H

670 Astrosterioside A Type: Cholestane steroids. C61H98O31S Source: Starfish Astropecten monacanthus (extracts, Cat Ba I., Haiphong, Vietnam). Pharm: IL-6 production inhibitor (stimulated bone marrow-derived dendritic cells, mild). Ref: N. P. Thao, et al, JNP, 2013, 76, 1764 O

H H HO O

O S

H O O

H O

HO HO HO

OH

O

O HO

O

O

O

O

O OH

OH

O

OH OH

HO

OH

O

OH OH O OH

268

2 Steroids

671 Blancasterol Type: Cholestane steroids. C31H50O8 Amorph. solid. Source: Sponge Pleraplysilla sp. (Vancouver, Canada). Pharm: Cytotoxic (in vitro, L1210, ED50 = 8 μg/mL; drugsensitive MCF7, ED50 = 3 μg/mL; MCF7 Adr, ED50 = 10 μg/mL). Ref: J. Pika, et al, Tetrahedron, 1993, 49, 8757 O O H HO

O

H HO O

OH

O

672 Carijoside A 3β-O-(3‘,4‘-Di-O-acetyl-β-D-arabinopyranosyl) -25ξ-cholestane-3β,5α,6β,26-tetrol-26acetate Type: Cholestane steroids. C38H62O11 White powder, mp 171–172 °C (dec), [α]D22 = −112° (c = 0.06, CHCl3). Source: Stolonifer Carijoa sp. (Pingtung county, Taiwan). Pharm: Cytotoxic (DLD-1, ED50 = 9.7 μg/mL; P388D1, ED50 = 10.4 μg/mL; HL60, ED50 = 12.0 μg/mL; CCRF-CEM, ED50 = 13.1 μg/mL); anti-inflammatory (hmn neutrophils: superoxide anion generation inhibitor, IC50 = 1.8 μg/mL; elastase release inhibitor, IC50 = 6.8 μg/mL). Ref: C. -Y. Liu, et al, Mar. Drugs, 2010, 8, 2014

H O

H H O O O

OH

OH

H

O

OH

O O O

673 Cholesta-5,23E-dien-3β,25-diol Type: Cholestane steroids. C27H44O2 Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.15 μg/mL; KB, ED50 = 0.61 μg/mL; A549, ED50 = 1.08 μg/mL; HT29, ED50 = 0.60 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1996, 59, 23

2.3 Cholestane Steroids (C27)

H

269

OH

HO

674 Cholesta-5,25-diene-3β,24ξ-diol Type: Cholestane steroids. C27H44O2 Powder, mp 193–195 °C, [α]D26 = −37° (c = 0.05, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.36 μg/mL; KB, ED50 = 0.67 μg/mL; A549, ED50 = 1.61 μg/mL; HT29, ED50 = 0.37 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1996, 59, 23 OH

H

HO

675 Cholesta-5,24-diene-3-O-sulfate-19-carboxylic acid Type: Cholestane steroids. C27H42O6S Amorph. powder. Source: Sponge Toxadocia zumi. Pharm: Antimicrobial; cytotoxic; ichthyotoxic; larvicide. Ref: T. Nakatsu, et al, Experientia, 1983, 39, 759

H HOOC

H O

O S O O

676 (3β,7β,22E)-Cholesta-5,22-diene-3,7,19-triol Type: Cholestane steroids. C27H44O3 Source: Black coral Antipathes subpinnata (Bay of Naples). Pharm: Toxic (lethal to brine shrimp, IC50 = 30.7 μg/mL). Ref: A. Aiello, et al, JNP, 1992, 55, 321

270

2 Steroids

H

HO

H OH

HO

677 Cholesta-7,22-diene-3β,5α,6β-triol Type: Cholestane steroids. C27H44O3 [α]D = −25° (MeOH). Source: Deep-sea fungus Trichoderma sp. GIBH-Mf082 (deep sea sediment, South China Sea), sponge Spongionella gracilis, bryozoan Myriapora truncata, clam Patinopecten yessoensis, crinoid Heliometra glacialis maxima. Pharm: Cytotoxic (A549, IC50 = 0.29 mmol/L); Taq DNA polymerase inhibitor (4.8 mmol/L, completely inhibition, IC50 = 0.45 mmol/L); HIV-1 protease inhibitor (0.24 mmol/L, 17.61% inhibition; HIV-1 induced cytopathic effect in MT-2 cells, 0.2 mmol/L, inactive). Ref: F. Cafieri, et al, JNP, 1985, 48, 944│H. Takami, et al, FEMS Microbiol. Lett., 1997, 152, 279│L. K. Shubina, et al, Comp. Biochem. Physiol., B: Biochem. Mol. Biol., 1998, 119, 505│J. You, et al, J. Ind. Microbiol. Biotechnol., 2010, 37, 245│CRC Press, DNP on DVD, 2012, version 20.2 22

H

7

HO

OH

OH

678 Cholesta-5-ene-3-O-sulfate-19-carboxylic acid Type: Cholestane steroids. C27H44O6S Source: Sponge Toxadocia zumi. Pharm: Antimicrobial; cytotoxic; ichthyotoxic; larvicide. Ref: T. Nakatsu, et al, Experientia, 1983, 39, 759

H HOOC

O HO

S O O

2.3 Cholestane Steroids (C27)

271

679 Cholestane-3α,6α-Diacetoxy-22S,25-diol Type: Cholestane steroids. C31H52O6 Oil, [α]D = +37.3° (c = 0.67, MeOH). Source: Soft coral Gersemia fruticosa (psychrophilic, cold water, Arctic, Northern Russia). Pharm: Cytotoxic (in vitro, inhibits growth of K562, IC50 = 14 μmol/L; HL60, IC50 = 29 μmol/L; P388, IC50 = 21 μmol/L); apoptosis inducer. Ref: R. Koljak, et al, Tetrahedron, 1998, 54, 179│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) OH

OH

H

O O O

O

680 Cholestane-3,6,8,15,16,25,26-heptol Type: Cholestane steroids. C27H48O7 Source: Starfish Echinasteridae sp. (Antarctic). Pharm: Cytotoxic (NSCLC-N6, IC50 = 3.3 μg/mL). Ref: M. Iorizzi, et al, Tetrahedron, 1996, 52, 10 997│S. De Marino, et al, Gazz. Chim. Ital., 1996, 126, 667 OH H OH

OH OH

OH HO OH

681 (3β,4β,5α,6β,8β,15β,24R)-Cholestane-3,4,6,8,15,24,25-heptol Type: Cholestane steroids. C27H48O7 Amorph. powder, [α]D = −2.4° (c = 0.3, MeOH). Source: Starfish Henricia leviuscula (psychrophilic, cold water, Sea of Okhotsk, Russia). Pharm: Hemolytic (mouse-erythrocytes assay, HC50 = 210 μmol/L). Ref: N. V. Ivanchina, et al, JNP, 2006, 69, 224│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) OH

H OH OH HO OH

OH

OH

272

2 Steroids

682 (25S)-5α-Cholestane-3β,5,6β,15α,16β,26-hexaol 26-sulfate Type: Cholestane steroids. C27H48O9S Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653 O

H O OH

S O OH

OH HO OH

OH

683 (25S)-5α-Cholestane-3β,5,6β,15α,16β,26-hexaol 16-sulfate Type: Cholestane steroids. C27H48O9S [α]D = +16.0°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653 OH

H

O O

S

H O

O OH HO OH

OH

684 (3β,4β,5α,6β,15α,24S)-Cholestane-3,4,6,8,15,24-hexol Type: Cholestane steroids. C27H48O6 Amorph. powder, [α]D25 = +14.7° (c = 0.1, MeOH). Source: Starfish Hippasteria kurilensis. Pharm: Inhibits sea urchin egg fertilization (compound-preincubated sperm of sea urchin Strongylocentrotus nudus, 1.3 × 10−5 mol/L, InRt = 100%). Ref: A. A. Kicha, et al, JNP, 2008, 71, 793 OH

H OH OH HO OH

H

OH

24S

2.3 Cholestane Steroids (C27)

273

685 (3β,4β,5α,6α,15β,24S)-Cholestane-3,4,6,8,15,24-hexol Type: Cholestane steroids. C27H48O6 [α]D = +7.2° (c = 0.4, MeOH). Source: Starfishes Gomophia watsoni and Nardoa tuberculata. Pharm: Toxic (brine shrimp). Ref: CRC Press, DNP on DVD, 2012, version 20.2 OH

H OH OH HO OH

H

OH

686 (3β,5α,6β,7α,15α,16β)-Cholestane-3,6,7,15,16,26-hexol Type: Cholestane steroids. C27H48O6 Cryst. (MeOH), mp 238–241 °C, [α]D = +3.8° (c = 0.5, MeOH). Source: Starfishes Luidia maculata and Luidia clathrata. Pharm: Antibarnacle. Ref: L. Minale, et al, JNP, 1984, 47, 784│M. Iorizzi, et al, JNP, 1995, 58, 653 OH

H H

OH OH

HO

OH OH

687 Cholestane-3,6,8,15,16,26-hexol Type: Cholestane steroids. C27H48O6 [α]D = +12.0° (MeOH). Source: Starfish Echinasteridae sp. (Antarctic). Pharm: Cytotoxic (NSCLC-N6, IC50 > 30 μg/mL). Ref: M. Iorizzi, et al, Tetrahedron, 1996, 52, 10 997│S. De Marino, et al, Gazz. Chim. Ital., 1996, 126, 667 OH H OH

OH OH

HO OH

274

2 Steroids

688 (25S)-5β-Cholestane-3β,6β,15α,16β,26-pentol Type: Cholestane steroids. C27H48O5 [α]D = +28°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653 OH

H OH OH HO H

OH

689 (25R)-5α-Cholestane-3β,6β,15α,16β,26-pentol Type: Cholestane steroids. C27H48O5 mp 133–135 °C, [α]D = +29.5° (c = 2.3, MeOH); [α]D = +5.0° (MeOH). Source: Starfish Echinasteridae sp. (Antarctic). Pharm: Cytotoxic (NSCLC-N6, IC50 > 30 μg/mL). Ref: M. lorizzi, et al, Tetrahedron, 1996, 52, 10997│S. De Marino, et al, Gazz. Chim. Ital., 1996, 126, 667│I. Izzo, et al, JOC, 1998, 63, 4438 OH

H OH OH HO OH

690 (24S)-5α-Cholestane-3β,5,6β,15α,24-pentol 15-sulfate Type: Cholestane steroids. C27H48O8S [α]D = +24.6°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653 OH

H

O O HO OH

S O

OH

OH

2.3 Cholestane Steroids (C27)

275

691 5α-Cholestane-3β,5,6β,15α,16β-pentol 16-sulfate Type: Cholestane steroids. C27H48O8S [α]D = +14.5°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653

H

O O

S

OH

O OH HO

OH

OH

692 5β-Cholestane-3α,4α,11β,21-tetraol 3,21-disulfate Type: Cholestane steroids. C27H48O10S2 Amorph. powder, [α]D = +41.3° (MeOH) (diNa salt). Source: Ophiuroids Ophiocoma dentata, Ophioderma longicaudum, Ophiarthrum elegans, Ophioplocus januarii, Ophiarachna incrassata, Ophiocoma scolopendrina, Ophionereis reticulata, Ophiozona impressa, Ophiocoma wendti and Ophiocoma echinata. Pharm: Protein tyrosine kinase inhibitor. Ref: M. V. D’Auria, et al, JOC, 1987, 52, 3947; 1989, 54, 234│M. V. D’Auria, et al, Nat. Prod. Lett., 1993, 3, 197│X. Fu, et al, JNP, 1994, 57, 1591│A. J. Roccatagliata, et al, JNP, 1996, 59, 887│CRC Press, DNP on DVD, 2012, version 20.2 O OH S O

O

H

HO H O HO

S O

O OH

H

693 (3α,4β,5α)-Cholestane-3,4,21-triol 3,21-di-O-sulfate Type: Cholestane steroids. C27H48O9S2 [α]D = +6.5° (c = 1.1, MeOH). Source: Starfish Pteraster pulvillus (psychrophilic, cold water, Kuril Is.), ophiuroid Gorgonocephalus chilensis. Pharm: Hemolytic (mouse-erythrocytes assay, HC50 = 4.5 × 10−5 mol/L). Ref: M. S. Maier, et al, Molecules, 2000, 5, 348│N. V. Ivanchina, et al, JNP, 2003, 66, 298│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

276

2 Steroids

HO O

O S

O

H H HO O

O S

O OH

H

694 Cholest-4-ene-3α,6β-diol Type: Cholestane steroids. C27H46O2 Source: Red algae Acanthophora spicifera. Pharm: Antifertility agent; antiviral (Semliki forest virus). Ref: S. Wahidulla, et al, Phytochemistry, 1998, 48, 1203

H

HO OH

695 3α-Cholest-5-ene-3,21-diol 3,21-disulfate Type: Cholestane steroids. C27H46O8S2 Cryst. (MeOH), mp 176–178 °C, [α]D20 = −11° (c = 0.1, EtOH). Source: Ophiuroids Gorgonocephalus chilensis, Ophioderma longicaudum, Ophionotus victoriae, Ophiothrix fragilis, Ophiura sarsi, Ophiura texturata, Ophiopholis aculeata, Ophiolepis superba, Ophiarachna incrassata, Ophiozona impressa and Stegophiura brachiactis. Pharm: Protein tyrosine kinase inhibitor. Ref: L. K. Shubina, et al, Comp. Biochem. Physiol., B: Biochem. Mol. Biol., 1998, 119, 505│CRC Press, DNP on DVD, 2012, version 20.2

HO O

O S

O H

HO O

O S

O

H

2.3 Cholestane Steroids (C27)

277

696 Cholest-4-ene-3,24-dione Type: Cholestane steroids. C27H42O2 Source: Soft coral Dendronephthya gigantean, Apis mellifer, ovary of queen honeybee. Pharm: Cytotoxic (P388, IC50 = 8.93 μmol/L, control Mithramycin, IC50 = 0.15 μmol/L; HT29, IC50 = 9.03 μmol/L, Mithramycin, IC50 = 0.21 μmol/L). Ref: M. J. Barbier, Chem. Ecol., 1987, 13, 1681│C. Y. Duh, et al, JNP, 2004, 67, 1650 O

H H

O

697 (3β,4β,5α,6α,7α,8β,15β,24R)-Cholest-22E-ene-3,4,6,7,8,15,24-heptol 6-O-sulfate Type: Cholestane steroids. C27H46O10S Amorph. powder, [α]D25 = 0° (c = 0.1, MeOH). Source: Starfish Hippasteria kurilensis. Pharm: Inhibits sea urchin egg fertilization (compound-preincubated sperm of sea urchin Strongylocentrotus nudus, EC100 = 8.9 × 10−5 mol/L). Ref: A. A. Kicha, et al, JNP, 2008, 71, 793 OH

H OH

24R

15

OH HO OH

H

OH O

S O

O OH

698 (3β,4β,5α,6α,8β,15β,22E,24R)-Cholest-22-ene-3,4,6,8,15,24-hexol Type: Cholestane steroids. C27H46O6 [α]D = +4.2° (c = 1, MeOH), [α]D = −10° (MeOH). Source: Starfishes Acodontaster conspicuus and Echinasteridae sp. (Antarctic). Pharm: Antibacterial (Antarctic marine bacteria McM13.3 and McM32.2, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, Gazz. Chim. Ital., 1996, 126, 667│M. Iorizzi, et al, Tetrahedron, 1996, 52, 10997│S. De Marino, et al, JNP, 1997, 60, 959

278

2 Steroids

OH 24R

H OH OH HO OH

H

OH

699 (25R)-Cholest-22-ene-3,6,8,15,16,26-hexol Type: Cholestane steroids. C27H46O6 [α]D = +16.0° (MeOH). Source: Starfish Echinasteridae sp. (Antarctic). Pharm: Cytotoxic (NSCLC-N6, IC50 > 30 μg/mL). Ref: M. Iorizzi, et al, Tetrahedron, 1996, 52, 10 997│S. De Marino, et al, Gazz. Chim. Ital., 1996, 126, 667 25R

OH H OH

OH OH

HO OH

700 Cholest-22E-ene-3β,6β,8β,15α,24R-pentol Type: Cholestane steroids. C27H46O5 [α]D = +12.3° (MeOH). Source: Starfish Echinasteridae sp. (Antarctic). Pharm: Cytotoxic (NSCLC-N6, IC50 > 30 μg/mL). Ref: M. Iorizzi, et al, Tetrahedron, 1996, 52, 10 997│S. De Marino, et al, Gazz. Chim. Ital., 1996, 126, 667 OH

H OH OH HO OH

701 (3β,7β,9α)-Cholest-5-ene-3,7,9,19-tetrol Type: Cholestane steroids. C27H46O4 Cryst., mp 165–167 °C. Source: Black coral Antipathes subpinnata (Bay of Naples). Pharm: Toxic (lethal to brine shrimp, IC50 = 7.2 μg/mL). Ref: A. Aiello, et al, JNP, 1992, 55, 321

2.3 Cholestane Steroids (C27)

279

H HO

H OH

HO

OH

702 (20R)-Cholest-5-ene-2α,3α,4β,21-tetrol 3,21-disulfate Type: Cholestane steroids. C27H46O10S2 Source: Ophiuroid Ophioderma longicaudum (Antarctic). Pharm: Cytotoxic (high active). Ref: M. V. D’Auria, et al, Nat. Prod. Lett., 1993, 3, 197

O

HO O

S

O

H

H

HO O HO O

S

O OH

703 (3β,7β)-Cholest-5-ene-3,7,19-triol Type: Cholestane steroids. C27H46O3 Cryst., mp 154–156 °C. Source: Black coral Antipathes subpinnata (Bay of Naples). Pharm: Toxic (lethal to brine shrimp, IC50 = 55.6 μg/mL). Ref: A. Aiello, et al, JNP, 1992, 55, 321

H HO

H H

HO

OH

704 Cholest-24-ene-(3α,6β,7β)-triol Type: Cholestane steroids. C27H46O3 Amorph. powder, [α]D = +47.4° (c = 2.1, MeOH). Source: Soft coral Gersemia fruticosa (psychrophilic, cold water, Arctic, Northern Russia). Pharm: Cytotoxic (in vitro, inhibits growth of K562, IC50 = 16 μmol/L; HL60, IC50 = 18 μmol/L; P388, IC50 = 21 μmol/L); apoptosis inducer. Ref: R. Koljak, et al, Tetrahedron, 1998, 54, 179│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

280

2 Steroids

H

HO

OH OH

705 Cholest-7-ene-3,5,6-triol Type: Cholestane steroids. C27H46O3 [α]D = −20.8° (MeOH). Source: Sea hares Patinopecten yessoensis and Aplysia juliana. Pharm: Cytotoxic (HeLa-S3, IC50 = 0.00016 ng/mL). Ref: Y. Yamaguchi, et al, Chem. Lett., 1992, 1713

H

HO OH

OH

706 (2β,3α)-Cholest-5-ene-2,3,21-triol 3,21-disulfate Type: Cholestane steroids. C27H46O9S2 [α]D = +8.7°. Source: Ophiuroids Gorgonocephalus chilensis, Gorgonocephalus caryi, Ophiothrix fragilis, Ophiura texturata, Ophiura leptoctenia, Ophioderma longicaudum (Antarctic) and Ophionotus victoriae, starfish Pteraster tessellatus. Pharm: Anti-HIV-1 (cytoprotective agent). Ref: M. V. D’Auria, et al, Nat. Prod. Lett., 1993, 3, 197│M. V. D’Auria, et al, JNP, 1995, 58, 189│L. K. Shubina, et al, Comp. Biochem. Physiol., B: Biochem. Mol. Biol., 1998, 119, 505

HO O

HO O HO O

S

O S

O

H

H

O

707 Cholest-5-ene-1,3,21-triol-3,21-disulfate Type: Cholestane steroids. C27H46O9S2 Amorph. solid, [α]D = +16.7° (c = 0.62, MeOH aq). Source: Ophiuroid (brittle star) Ophiarachna incrassata. Pharm: Protein tyrosine kinase inhibitor (a component of the protein tyrosine kinase inhibitor pp60). Ref: X. Fu, et al, JNP, 1994, 57, 1591

2.3 Cholestane Steroids (C27)

281

OH O

S

O

O

H OH

O HO

S

H

O O

708 (3β,5α,6α,23S)-Cholest-9(11)-ene-3,6,23-triol 3,6-disulfate (disodium salt) Type: Cholestane steroids. C27H44O9S22− [α]D = +24.2° (c = 1, MeOH). Source: Starfishes Plazaster borealis and Aphelasterias japonica (Japan waters). Pharm: Induces avoidance reaction in sea urchin Strongylocentrotus nudus. Ref: E. Finamore, et al, JNP, 1992, 55, 767│N. Takahashi, et al, Fish. Sci., 2000, 66, 412

H

OH

–

O O

S

O

O

O

O

S

–

O

O

709 (3β,5α)-Cholest-7-en-3-ol Lathosterol Type: Cholestane steroids. C27H46O Needles (Me2CO), mp 125–127 °C Source: Scallop Trochostoma orientale (edible), starfishes Asterias pectinifera, Asterias rubens, Henricia sanguinolenta and Arthasterias glacialis, sea cucumbers Bathyplotes natans, Cucumaria sp., Eupentacta fraudatrix, Holothuria nobilis, Holothuria scabra and Psolus fabricii. Pharm: Antimutagenic (might be useful as chemopreventive agent). Ref: V. A. Stonik, et al, Comp. Biochem. Physiol., B: Biochem. Mol. Biol., 1998, 120, 337│Y. H. Han, et al, Biol. Pharm. Bull., 2000, 23, 1247

H

HO

H

282

2 Steroids

710 Cholesterol Type: Cholestane steroids. C27H46O Pearly leaflets (EtOH aq), mp 148.5 °C (anhyd.), [α]D = −31.12° (Et2O); white powder, mp 148–149 °C, [α]D25 = −31.6° (c = 1.00, Et2O). Source: Gorgonian Eunicea fusca (Santa Marta Bay, Caribbean Sea, Colombia), Soft coral Lobophytum laevigatum (Khanh Hoa province, Vietnam); characteristic sterol of higher animals, fish liver oils, egg yolk, bile and gallstones etc., and occurs in many marine organisms. Pharm: Pharmaceutical aid (emulsifying agent); emollient. Ref: V. A. Stonik, et al, Comp. Biochem. Physiol., B: Biochem. Mol. Biol., 1998, 120, 337│L. Castellanos, et al, Biochem. Syst. Ecol. 2003, 31, 1163│T. H. Quang, et al, BoMCL, 2011, 21, 2845│E. Reina, et al, BoMCL, 2011, 21, 5888

H H

HO

711 Crellastatin A Type: Cholestane steroids. C58H88O12S Amorph. powder, [α]D = +55° (c = 1,MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Cytotoxic (NSCLC-N6, IC50 = 1.5 μg/mL). Ref: M. V. D’Auria, et al, JOC, 1998, 63, 7382

O

H HO

H

HO O

S

O O

2

O HO

O

O 6

2'

OH

OH

712 Crellastatin B 2-DeoxycrellastatinA Type: Cholestane steroids. C58H88O11S Amorph. powder, [α]D = +32° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Antineoplastic (NSCLC, in vitro, IC50 = 1.2 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│C. Giannini, et al, Tetrahedron, 1999, 55, 13749

2.3 Cholestane Steroids (C27)

283

O OH O

H

O S O O

H H O 2

OH

2'

O HO

OH 6

713 Crellastatin C 2ʹ-DeoxycrellastatinA Type: Cholestane steroids. C58H88O11S Amorph. powder, [α]D = +50.9° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Antineoplastic (NSCLC, in vitro, IC50 = 3.4 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│C. Giannini, et al, Tetrahedron, 1999, 55, 13749 O O O

H

OH O S O

H

H

O 2

HO HO

OH

2'

O 6

714 Crellastatin D 2,2′-DideoxycrellastatinA Type: Cholestane steroids. C58H88O10S Amorph. powder, [α]D = +51.6° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Antineoplastic (NSCLC, in vitro, IC50 = 5.94 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│C. Giannini, et al, Tetrahedron, 1999, 55, 13749 O O O H

H

OH O S O

H O OH

2 2'

O HO

6

284

2 Steroids

715 Crellastatin E Type: Cholestane steroids. C58H88O11S Amorph. powder, [α]D = +11.4° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Antineoplastic (NSCLC, in vitro, IC50 = 9.87 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│C. Giannini, et al, Tetrahedron, 1999, 55, 13749

O H

H

O

HO

O

S O

H

HO

O

O HO

O HO

716 Crellastatin F Type: Cholestane steroids. C58H90O16S2 Amorph. powder, [α]D = +60.3° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Antineoplastic (NSCLC, in vitro, IC50 = 2.7 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│C. Giannini, et al, Tetrahedron, 1999, 55, 13749

O O O H

H

OH O S O

H O

HO

2 2'

O HO

6

O

OH

OH S

O OH O

717 Crellastatin G Type: Cholestane steroids. C58H90O15S2 Amorph. powder, [α]D = +68.7° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Antineoplastic (NSCLC, in vitro, IC50 = 2.5 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│C. Giannini, et al, Tetrahedron, 1999, 55, 13749

2.3 Cholestane Steroids (C27)

285

O O O

O H

H HO

H

O

2

2'

O HO

OH O S

OH

6

O O S OH O

718 Crellastatin H Type: Cholestane steroids. C58H90O15S2 Amorph. powder, [α]D = +27.8° (c = 0.001, MeOH). Source: Sponge Crella sp. (Vanuatu). Pharm: Antineoplastic (NSCLC, in vitro, IC50 = 2.3 μg/mL). Ref: A. Zampella, et al, EurJOC, 1999, 949│C. Giannini, et al, Tetrahedron, 1999, 55, 13749

O H

H

O

O

HO S O

O

H

O HO

OH O

6

O

O

S

HO OH

O

719 Crossasteroside A (3β,5α,6α,7α,15α,24S)-Cholestane-3,6,7,8,15,24-hexol 24-O-[4-O-methyl-β-D-xylopyranosyl-(1→2)-3-O-methyl-β-D-xylopyranoside] Type: Cholestane steroids. C39H68O14 [α]D = −19.5° (c = 1.6, CHCl3). Source: Starfish Crossaster papposus. Pharm: Muscle contraction inhibitor. Ref: L. Andersson, et al, J. Chem. Res., Synop., 1985, 366; 1987, 246

286

2 Steroids

O H

24S

O O

OH HO

H

OH OO

OH OH

OH OH

O OH

720 Crossasteroside B (3β,5α,6α,15α,24S)-Cholestane-3,6,8,15,24-pentol 24-O-[4-O-methyl-β-D-xylopyranosyl(1→2)-3-O-methyl-β-D-xylopyranoside] Type: Cholestane steroids. C39H68O13 [α]D = −5° (MeOH). Source: Starfish Crossaster papposus. Pharm: Muscle contraction inhibitor. Ref: L. Andersson, et al, J. Chem. Res., Synop., 1987, 246; J. Chem. Res., Miniprint, 2085 O H OH

O

24

O

15

OH

OH

OH

OO HO

H

O OH

OH

721 24-Dehydrocholesterol Type: Cholestane steroids. C27H44O Cryst. (Me2CO/MeOH), mp 121.5–122.5 °C, [α]D20 = −38.2° (c = 1.143, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters), red algae Rhodymenia palmata and Halosaccion ramentaceum, scallop Patinopecten yessoensis, and occurs in many other marine organisms. Pharm: Cytotoxic (P388, ED50 = 33.53 μg/mL; KB, ED50 > 50 μg/mL; A549, ED50 > 50 μg/mL; HT29, ED50 > 50 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1996, 59, 23│CRC Press, DNP on DVD, 2012, version 20.2

H

HO

722 Dendronesterol B Type: Cholestane steroids. C29H50O6 Amorph. solid, [α]D25 = +1° (c = 0.9, MeOH). Source: Soft coral Dendronephthya gigantea (Japan waters). Pharm: Cytotoxic (L1210, IC50 = 5.2 μg/mL). Ref: K. Yoshikawa, et al, JNP, 2000, 63, 670

2.3 Cholestane Steroids (C27)

287

O O H H OH HO OH

OH

723 Dendronesterone A Type: Cholestane steroids. C27H42O Solid, [α]D25 = +16° (c = 0.3, CHCl3). Source: Soft Coral Dendronephthya gigantean. Pharm: Cytotoxic (P388, IC50 = 9.84 μmol/L, control Mithramycin, IC50 = 0.15 μmol/L; HT29, IC50 > 100 μmol/L). Ref: C. Y. Duh, et al, JNP, 2004, 67, 1650

H H

O

724 24-Desulfo-24-ketone-26-[(2-amino-2-carboxyethyl)lthio]-squalamine Type: Cholestane steroids. C37H68N4O4S White powder. Source: Dogfish shark Squalus acanthias (from liver). Pharm: Antibacterial (Staphylococcus aureus, IC50 = 8–16 μg/mL, Escherichia coli, IC50 = 256 μg/mL, Pseudomonas aeruginosa, IC50 = 256 μg/mL); antifungal (Candida albicans, IC50 = 128 μg/mL). Ref: M. N. Rao, et al, JNP, 2000, 63, 631 O 25 24

H H 2N

26

S

H H2N

HN N H

OH

HO

O

725 3α,11α-Diacetoxy-25-hydroxycholest-4-en-6-one Type: Cholestane steroids. C31H48O6 Amorph. powder, [α]D25 = +62.4° (c = 0.14, CHCl3). Source: Gorgonian Dasystenella acanthina (psychrophilic, cold water, Antarctic). Pharm: Cytotoxic (DU145, GI50 = 2.3 μg/mL; LNCaP, GI50 = 2.3 μg/mL; IGROV, GI50 = 2.2 μg/mL; SKBR3, GI50 = 3.2 μg/mL; SK-MEL-28, GI50 = 2.0 μg/mL;

288

2 Steroids

A549, GI50 = 4.2 μg/mL; K562, GI50 = 1.5 μg/mL; PANC1, GI50 = 2.4 μg/mL; HT29, GI50 = 2.9 μg/mL; LoVo, GI50 = 2.0 μg/mL; LoVo-DOX, GI50 = 1.7 μg/mL; HeLa, GI50 = 2.9 μg/mL; growth inhibitor). Ref: G. G. Mellado, et al, Steroids, 2004, 69, 291│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O H

O

24

OH

H O

H

H

O O

726 (20S)-18,20-Dihydroxycholesta-1,4-diene-3,16-dione Type: Cholestane steroids. C27H40O4 Source: Black coral Antipathes subpinnata (Bay of Naples). Pharm: Toxic (lethal to brine shrimp, IC50 = 39.4 μg/mL). Ref: A. Aiello, et al, JNP, 1992, 55, 321 OH HO H O

O

727 (5α,22ξ,23ξ)-22,23-Dihydroxycholesta-1,24-dien-3-one Type: Cholestane steroids. C27H42O3 Cryst., mp 106–109 °C, [α]D22 = −40.9° (c = 0.13, CH2Cl2). Source: Soft corals Alcyonium gracillimum (Japan waters) and Scleronephthya sp. Pharm: Antifoulant (barnacle Balanus Amphitrite (cyprid larvae), LD100 = 100 μg/mL). Ref: Y. Tomono, et al, JNP, 1999, 62, 1538 OH

H

OH

O

728 (3β,5α,6α)-3,6-Dihydroxycholesta-9(11),24-dien-23-one 3-sulfate Type: Cholestane steroids. C27H42O6S Amorph. powder, [α]D = +4.2° (c = 0.65, MeOH). Source: Starfishes Asterias rathbuni and Lysastrosoma anthosticta (Pacific Ocean). Pharm: Cytotoxicstatic (cell division inhibitor, fertilized sea urchin eggs,

2.3 Cholestane Steroids (C27)

289

IC100 = 2.9 × 10−5 mol/L). Ref: N. V. Ivanchina, et al, JNP, 2001, 64, 945│ E. V. Levina, et al, Russ. Chem. Bull. (Engl. Transl.), 2001, 50, 313

H

O

H HO O

O S

O

H

OH

729 (16S,20S)-16,20-Dihydroxycholestan-3-one Type: Cholestane steroids. C27H46O3 White solid. [α]D = +14.4° (c = 0.16, CHCl3). Source: Gorgonian Leptogorgia sarmentosa (Spain). Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all ED50s = 1 μg/mL). Ref: L. Garrido, et al, Steroids, 2000, 65, 85 OH H H H O

OH H

H

730 6β,16β-Dihydroxycholest-4-en-3-one Type: Cholestane steroids. C27H44O3 White solid, mp 163 °C. Source: Red alga Jania adhaerens (Al-Shoaiba coast, Red Sea). Pharm: Antigenotoxic (hmn peripheral blood cells). Ref: W. M. Alarif, et al, Nat. Prod. Res., 2012, 26, 785

H H H

OH H

O OH

731 3,6-Dihydroxy-24-nor-9-oxo-9,11-secocholesta-7,22-dien-11-al Type: Cholestane steroids. C26H40O4 Oil. Source: Soft coral Gersemia fruticosa (psychrophilic, cold water, Arctic, Northern Russia). Pharm: Cytotoxic (in vitro, inhibits growth of K562, IC50 > 60 μmol/L). Ref: R. Koljak, et al, Tetrahedron, 1998, 54, 179│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

290

2 Steroids

O

H H

O H HO

H

OH

732 Dimorphoside A 3-[(3-O-β-D-Arabinofuranosyl-β-D-glucopyranosyl)oxy]-7-hydroxycholest-5-en-19-oic acid Type: Cholestane steroids. C38H62O13 Amorph. solid, [α]D23 = −59° (c = 0.38, MeOH). Source: Gorgonian Anthoplexaura dimorpha. Pharm: Cell division inhibitor. Ref: N. Fusetani, et al, Tet. Lett., 1987, 28, 1187

H

O

HO

H HO OO

7

OH

OH HO O

O

OH

HO 2''

OH

733 5,8-epi-Dioxycholesta-6-en-3-ol Type: Cholestane steroids. C27H44O3 Source: Ascidian Cynthia sp. annelid polychaete worm Perinereis aibuhitensis. Pharm: Antibacterial, antifungal; cytotoxic. Ref: C. V. Minh, et al, Arch. Pharmacal Res., 2004, 27, 734

H

HO

O

O

734 Diplasterioside A Type: Cholestane steroids. C58H96O27S Source: Starfish Diplasterias brucei (Antarctic, Ross Sea, Terra Nova Bay). Pharm: Cytotoxic (hmn melanoma cell line, mild). Ref: N. V. Ivanchina, et al, Russ. J. Bioorg. Chem., 2011, 37, 499

2.3 Cholestane Steroids (C27)

291

O OH H H OH O O S O HO HO HO

OH OO HO O

HO

HO OO O O

O

OH

H H OO

OH

HO HO

735 Dysideasterol A Type: Cholestane steroids. C29H46O6 Cryst. (CHCl3/hexane), mp 229–230 °C, mp 204–205 °C, [α]D26 = +42.6° (c = 0.07, CHCl3), [α]D20 = +60° (c = 0.13, CHCl3). Source: Sponges Dysidea arenaria and Dysidea sp. Pharm: Cytotoxic (PS, ED50 = 4.9 μg/ mL); reverses fluconazole resistance in multidrug-efflux resistant fungi. Ref: S. P. Gunasekera, et al, JOC, 1983, 48, 885│Y. Fujimoto, et al, CPB, 1985, 33, 3129│M. R. Jacob, et al, JNP, 2003, 66, 1618│X. -C. Huang, et al, Helv. Chim. Acta, 2005, 88, 281│CRC press, DNP, on DVD, 2012, version 20.2

H HO

HO

O

OH

O

O

736 Dysideasterol F Type: Cholestane steroids. C29H46O6 Source: Sponge Dysidea sp. (Ishigaki I., Okinawa). Pharm: Cytotoxic (hmn epidermoid carcinoma cells). Ref: S. V. S. Govindam, et al, Biosci., Biotechnol., Biochem., 2012, 76, 999

292

2 Steroids

H

O

OH HO

OH

H

O O

737 Dysideasterol G Type: Cholestane steroids. C29H44O5 Source: Sponge Dysidea sp. (Ishigaki I., Okinawa). Pharm: Cytotoxic (hmn epidermoid carcinoma cells). Ref: S. V. S. Govindam, et al, Biosci., Biotechnol., Biochem., 2012, 76, 999

H O H HO

OH

O O

738 24ξ,25-Epoxy-12β-acetoxycholest-4-en-3-one Type: Cholestane steroids. C29H44O4 Amorph. powder, [α]D25 = +71.8° (c = 0.03, CHCl3). Source: Gorgonian Dasystenella acanthina (psychrophilic, cold water, Antarctic). Pharm: Cytotoxic (DU145, GI50 = 4.1 μg/mL; LNCaP, GI50 = 1.5 μg/mL; IGROV, GI50 = 5.2 μg/mL; SKBR3, GI50 = 3.4 μg/mL; SK-MEL-28, GI50 = 3.4 μg/mL; A549, GI50 = 4.4 μg/mL; K562, GI50 = 1.3 μg/mL; PANC1, GI50 = 2.9 μg/mL; HT29, GI50 = 3.5 μg/mL; LoVo, GI50 = 2.2 μg/mL; LoVo-DOX, GI50 = 1.9 μg/mL; HeLa, GI50 = 3.6 μg/mL; cell growth inhibitor). Ref: G. G. Mellado, et al, Steroids, 2004, 69, 291│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O O O H H H O

H

24

2.3 Cholestane Steroids (C27)

293

739 24ξ,25-Epoxy-23ξ-acetoxycholest-4-en-3-one Type: Cholestane steroids. C29H44O4 Amorph. powder, [α]D25 = +51.4° (c = 0.12, CHCl3). Source: Gorgonian Dasystenella acanthina (psychrophilic, cold water, Antarctic). Pharm: Cytotoxic (LNCaP, GI50 = 1.7 μg/mL; IGROV, GI50 = 5.0 μg/mL; SKBR3, GI50 = 2.2 μg/mL; SK-MEL-28, GI50 = 3.1 μg/mL; K562, GI50 = 1.2 μg/mL; PANC1, GI50 = 3.1 μg/mL; HT29, GI50 = 2.6 μg/mL; LoVo, GI50 = 2.9 μg/mL; LoVo-DOX, GI50 = 3.1 μg/mL; HeLa, GI50 = 3.4 μg/mL; cell growth inhibitor). Ref: G. G. Mellado, et al, Steroids, 2004, 69, 291│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O H

24

O

H O H

H

O

740 7α,8α-Epoxy-3β-acetoxy-,5α,6α-dihydroxycholest-24-ene Type: Cholestane steroids. C29H46O5 Source: Gorgonian Acabaria undulata (Korea waters). Pharm: Cytotoxic (P388, IC50 = 11.6 μg/mL; DLD-1, IC50 = 12.6 μg/mL; PLA2, 100 μg/mL, inactive). Ref: J. Shin, et al, JNP, 1996, 59, 679 H

O

O O

OH OH

741 18,22-Epoxycholesta-1,20(22)-dien-3-one Type: Cholestane steroids. C27H40O2 Cryst., mp 52–53 °C, [α]D = +34.0° (c = 0.5, CDCl3). Source: Soft coral Alcyonium gracillimum (Korea waters). Pharm: Cytotoxic (P388, IC50 = 7.8 μg/mL); antiviral (HSV-1); antiviral (hmn cytogalovirus, IC50 = 7.2 μg/mL). Ref: Y. Sco, et al, Tetrahedron, 1995, 51, 2497

O H

O

294

2 Steroids

742 7,8-Epoxycholestane-3,5,6-triol Type: Cholestane steroids. C27H46O4 White solid, mp 169–171 °C. Source: Gorgonian Acabaria undulata (Korea waters). Pharm: Cytotoxic (P388, IC50 = 17.9 μg/mL; DLD-1, IC50 = 19.6 μg/mL; PLA2, IC50 = 13.8 μg/mL). Ref: J. Shin, et al, JNP, 1996, 59, 679

H

O HO OH OH

743 5β,6β-Epoxycholest-24-ene-3β,7β-diol Type: Cholestane steroids. C27H44O3 Plates, mp 122–123 °C, [α]D = +49.5° (c = 2.87, MeOH). Source: Soft coral Gersemia fruticosa (psychrophilic, cold water, Arctic, Northern Russia). Pharm: Cytotoxic (against growth of K562, IC50 > 60 μmol/L); cytotoxic (in vitro, inhibits growth of K562, IC50 = 21 μmol/L; HL60, IC50 = 14 μmol/L; P388, IC50 = 18 μmol/L); apoptosis inducer (K562 with a characteristic internucleosomal DNA degradation). Ref: R. Koljak, et al, Tetrahedron, 1998, 54, 179│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

H

HO

OH

O

744 24,25(R/S)-Epoxy-6β-hydroxycholest-4-en-3-one Type: Cholestane steroids. C27H42O3 Powder, mp 205–208 °C. Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.75 μg/mL; KB, ED50 = 0.30 μg/mL; A549, ED50 = 3.14 μg/mL; HT29, ED50 = 0.87 μg/mL). Ref: J.-H. Sheu, et al, JNP, 1996, 59, 23 O H H

O OH

2.3 Cholestane Steroids (C27)

295

745 4,5-Epoxy-2,3,12,22-tetrahydroxy-14-methylcholesta-7,9(11)-diene-6,24-dione Type: Cholestane steroids. C28H40O7 Powder. Source: Sponge Xestospongia sp. (Philippines). Pharm: HIV-1 integrase inhibitor. Ref: M. L. Lerch, et al, Tetrahedron, 2001, 7, 4091 OH

O

OH H HO

HO

O

O

746 Eryloside A (3β,4α,5α,23S)-4-Methylcholesta-8,14-diene-3,23-diol 3-O-[β-D-galactopyranosyl-(1→2)β-D-galactopyranoside] Type: Cholestane steroids. C40H66O12 Amorph. powder, mp 214–219 °C, mp 168–172 °C, [α]D = +11° (c = 1.5, CHCl3). Source: Sponge Erylus lendenfeldi. Pharm: Antineoplastic; antifungal. Ref: S. Carmely, et al, JNP, 1989, 52, 167 23S

H OH OH

OH O

O H

HO OO

HO HO HO

OH

747 Euryspongiol A1 Type: Cholestane steroids. C27H46O7 [α]D21 = −42° (c = 0.001, MeOH). Source: Sponge Euryspongia sp. (New Caledonia). Pharm: Antihistaminic (strongly inhibit release of histamine from rat mastocysts). Ref: J. Dopeso, et al, Tetrahedron, 1994, 50, 3813 22

HO H HO

O

HO

H H

HO OH

H

OH

296

2 Steroids

748 Euryspongiol A2 Type: Cholestane steroids. C27H48O7 [α]D21 = −22° (c = 0.001, MeOH). Source: Sponge Euryspongia sp. (New Caledonia). Pharm: Antihistaminic (strongly inhibit release of histamine from rat mastocysts). Ref: J. Dopeso, et al, Tetrahedron, 1994, 50, 3813

HO H HO

O

HO

H H

HO OH

H

OH

749 Fibrosterol sulfate B Type: Cholestane steroids. C54H88O22S5 Amorph. solid, [α]D22 = +19.1° (c = 0.08, MeOH). Source: Sponge Lissodendoryx fibrosa [Syn. Acanthodoryx fibrosa] (Coron I., Philippines). Pharm: PKCξ inhibitor. Ref: E. L. Whitson, et al, JOC, 2009, 74, 5902

OH OH O

H

S O

H

O H HO

H

H

H

OH

H

O O

H

S OH O

O

H

H O

HO

S O O

S O O

O

H O

S O OH

750 Fibrosterol sulfate C Type: Cholestane steroids. C55H90O18S4 Amorph. solid, [α]D20 = +29.2° (c = 0.13, MeOH). Source: Sponge Lissodendoryx fibrosa [Syn. Acanthodoryx fibrosa] (Coron I., Philippines). Pharm: PKCξ inhibitor. Ref: E. L. Whitson, et al, JOC, 2009, 74, 5902

2.3 Cholestane Steroids (C27)

297

O H

OH O

S

O

H

H

O

H

H HO

H

H O

H

O

H

S

O OH

HO

O

S

H H

O

O

H O O

S

O

OH

751 Fragilioside A Type: Cholestane steroids. C36H58O9 Source: Gorgonian Dichotella fragilis (Meishan, Sanya, China). Pharm: Antifoulant. Ref: Y. -M. Zhou, et al, Nat. Prod. Commun., 2011, 6, 1239

O

H HO

H H

O H

O O

OH

O

HO

O

752 Fragilioside B Type: Cholestane steroids. C36H58O9 Source: Gorgonian Dichotella fragilis (Meishan, Sanya, China). Pharm: Antifoulant. Ref: Y. -M. Zhou, et al, Nat. Prod. Commun., 2011, 6, 1239

O

H HO

H H

O O O

OH O

OH

O H

298

2 Steroids

753 Gelliusterol C 3β-Hydroxycholest-5-en-23-yn-7-one Type: Cholestane steroids. C27H40O2 [α]D = −36.6° (c = 0.28, MeOH). Source: Sponge Gellius sp. (Caribbean coast of Panama). Pharm: Cytotoxic (HT29, 0.5 μg/mL). Ref: W. A. Gallimore, et al, JNP, 2001, 64, 741

H H

HO

O

754 Glaciasterol B 3-acetate Type: Cholestane steroids. C29H46O5 Cryst. (hexane/MeOH), mp 97–99 °C, [α]D = +4.2° (c = 0.15, CHCl3). Source: Sponge Fasciospongia cavernosa (Mediterranean Sea). Toxic (brine shrimp). Ref: S. De Rosa, et al, Nat. Prod. Lett., 1999, 13, 15

HO

H

O O H O

O

755 Goniopectenoside A (3β,5α,6α,22R)-3,6,20,25-Tetrahydroxycholesta-9(11),23-dien-22-one 6-O-[β-D-fucopyranosyl-(1→2)-6-deoxy-β-D-glucopyranosyl-(1→4)-[6-deoxy-3-O-methyl-β-D-glucopyranosyl(1→2)]-β-D-xylopyranosyl-(1→3)-6-deoxy-β-D-glucopyranoside] 3-O-sulfate Type: Cholestane steroids. C57H92O28S Amorph. powder, [α]D = +1.9° (c = 0.3, MeOH). Source: Starfish Goniopecten demonstrans. Pharm: Inhibits settlement of biofouling alga Hincksia irregulatus. Ref: S. De Marino, et al, EurJOC, 2000, 4093

2.3 Cholestane Steroids (C27)

OH

299

O

H

OH

H HO O

O S

H OO

OH

OH

O

OH

O

OH

O

O

OH O

HO

O

O

BD-xylop

O

O

O

OH

OH

OH

BD-fucop OH

756 Goniopectenoside B Type: Cholestane steroids. C57H94O27S Amorph. powder, [α]D = −7.5° (c = 0.2, MeOH). Source: Starfish Goniopecten demonstrans. Pharm: Inhibits settlement of biofouling alga Hincksia irregulatus. Ref: S. De Marino, et al, EurJOC, 2000, 4093 OH H O O HO O

S

O

OH

OH

O

OH

O

O

O

OH O

HO

H OO O

BD-xylop

O

O

O O

OH

OH

BD-fucop OH

OH

300

2 Steroids

757 Goniopectenoside C (3β,6α,22R)-3,6,20-Trihydroxy-9(11),24-cholestadien-22-one 6-O-[β-D-fucopyranosyl(1→2)-6-deoxy-β-D-glucopyranosyl-(1→4)-[6-deoxy-3-O-methyl-β-D-glucopyranosyl(1→2)]-β-D-xylopyranosyl-(1→3)-6-deoxy-β-D-glucopyranoside] 3-O-sulfate Type: Cholestane steroids. C57H92O27S Amorph. powder, [α]D = +6.6° (c = 0.4, MeOH). Source: Starfish Goniopecten demonstrans. Pharm: Inhibits settlement of biofouling alga Hincksia irregulatus. Ref: S. De Marino, et al, EurJOC, 2000, 4093

OH

O

H H HO O

O S

O OO O

BD-xylop

O

OH

OH

O

OH

O

OH

O

O

OH O

HO

O

O

OH

OH

OH

BD-fucop OH

758 Halistanol sulfate C Type: Cholestane steroids. C27H48O12S3 [α]D21 = +27.5° (c = 1, MeOH). Source: Sponge Epipolasis sp. (Japan waters). Pharm: Thrombin inhibitor (IC50 = 16 μg/mL). Ref: S. Kanazawa, et al, Tetrahedron, 1992, 48, 5467

O O

O O

S

OH

H H

O

O S

H OH

O S

O OH

O

759 Halityloside F (3β,5α,6β,15β,24S)-Cholestane-3,6,8,15,24-pentol 24-O-[2,4-di-O-methyl-β-D-xylopyranosyl-(1→2)-α-L-arabinofuranoside] Type: Cholestane steroids. C39H68O13

2.3 Cholestane Steroids (C27)

301

[α]D = −14.1° (MeOH). Source: Starfishes Halityle regularis, Culcita novaeguineae, Nardoa tuberculata and Gomophia watsoni. Pharm: Toxic (brine shrimp). Ref: R. Riccio, et al, Gazz. Chim. Ital., 1985, 115, 405│M. Iorizzi, et al, JNP, 1986, 49, 67

O H OH 6

HO

H

24

O OH

15

OH

HO

OO OH

OH O O

760 Herbasterol 2β,3α,6β,11,19-Pentahydroxy-9,11-secocholestan-9-one Type: Cholestane steroids. C27H48O6 Hygroscopic solid, mp 113–115 °C, [α]D = +1.4° (c = 8.4, MeOH). Source: Sponge Dysidea herbacea. Pharm: Ichthyotoxin; cytotoxic. Ref: R. J. Capon, et al, JOC, 1985, 50, 4771

HO H HO

O

HO

H H

HO

H

OH

761 Hippasterioside B (20R,22R,23S)-22,23-Epoxy-20-hydroxy-6α-O-{β-D-xylopyranosyl-(1→3)-β-D-fucopyranosyl(1→2)-β-D-quinovopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-dxylopyranosyl(1→3)-β-D-quinovopyranosyl}-5α-cholest-9(11)-en-3β-yl 3-sulfate Type: Cholestane steroids. C61H100O30S Colorless amorph. powder, [α]D25 = ± 0° (c = 0.1, MeOH). Source: Starfish Hippasteria kurilensis (Kuril Is., Sea of Okhotsk, Russia). Pharm: Cytotoxic (HT29, inhibiting colony formation, reduced colony number by 16%). Ref: A. A. Kicha, et al, Chem. Biodiversity, 2011, 8, 166

302

2 Steroids

O

OH H H H

O HO

S

O

HO HO

O

O

O O

HO O O

HO OO

OO HO

HO HO

HO HO

O

H

O

O OH HO

OH

762 Hirsutosterol D Type: Cholestane steroids. C29H48O5 White powder, [α]D25 = −44° (c = 0.45, CHCl3). Source: Soft coral Cladiella hirsuta (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 = 30.9 μmol/L, control Doxorubicin, IC50 = 0.4 μmol/L; HepG3B, IC50 = 22.5 μmol/L, Doxorubicin, IC50 = 1.3 μmol/L; Ca9-22, IC50 = 20.2 μmol/L, Doxorubicin, IC50 = 0.2 μmol/L; A549, IC50 = 31.7 μmol/L, Doxorubicin, IC50 = 2.6 μmol/L; MCF7, IC50 = 33.4 μmol/L, Doxorubicin, IC50 = 2.9 μmol/L; MDA-MB-231, IC50 = 31.3 μmol/L, Doxorubicin, IC50 = 2.0 μmol/L). Ref: B. -W. Chen, et al, Org. Biomol. Chem., 2011, 9, 3272

H

HO

O

OH O

H

H

OH

763 Hirsutosterol G Type: Cholestane steroids. C29H46O5 White powder, [α]D25 = −16° (c = 0.14, CHCl3). Source: Soft coral Cladiella hirsuta (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 = 35.0 μmol/L, control Doxorubicin, IC50 = 0.4 μmol/L; HepG3B, IC50 = 28.1 μmol/L, Doxorubicin, IC50 = 1.3 μmol/L; Ca9-22, IC50 = 26.6 μmol/L, Doxorubicin, IC50 = 0.2 μmol/L; A549, IC50 = 38.4 μmol/L, Doxorubicin, IC50 = 2.6 μmol/L; MCF7, IC50 = 29.7 μmol/L, Doxorubicin, IC50 = 2.9 μmol/L; MDA-MB-231, IC50 = 42.0 μmol/L, Doxorubicin, IC50 = 2.0 μmol/L). Ref: B. -W. Chen, et al, Org. Biomol. Chem., 2011, 9, 3272

2.3 Cholestane Steroids (C27)

H

HO

O

303

OH O

H

OH

764 25-Hydroperoxycholesta-4,23-diene-3,6-dione Type: Cholestane steroids. C27H40O4 mp 185–188 °C, [α]D28 = +7.0° (c = 0.20, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.14 μg/mL, KB, ED50 = 0.45 μg/mL, A549, ED50 = 1.54 μg/mL, HT29, ED50 = 0.55 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1997, 60, 900 OH H

O

O O

765 24ξ-Hydroperoxycholesta-4,25-diene-3,6-dione Type: Cholestane steroids. C27H40O4 mp 213–214 °C, [α]D30 = +10.0° (c = 0.19, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.19 μg/mL, KB, ED50 = 0.83 μg/mL, A549, ED50 = 2.37 μg/mL, HT29, ED50 = 0.30 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1997, 60, 900 O

OH

H

O O

766 25-Hydroperoxycholesta-5,(23E)-dien-3β-ol Type: Cholestane steroids. C27H44O3 Powder, mp 148–151 °C, [α]D20 = −41° (c = 0.05, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.22 μg/mL; KB, ED50 = 1.41 μg/mL; A549, ED50 = 1.68 μg/mL; HT29, ED50 = 1.27 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1996, 59, 23

304

2 Steroids

H

O OH

HO

767 24ξ-Hydroperoxycholesta-5,25-dien-3β-ol Type: Cholestane steroids. C27H44O3 Powder, [α]D24 = −38° (c = 0.2, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.26 μg/mL; KB, ED50 = 0.33 μg/mL; A549, ED50 = 0.64 μg/mL; HT29, ED50 = 0.43 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1996, 59, 23 O

OH

H

HO

768 24ξ-Hydroperoxy-6β-hydroxycholesta-4,25-dien-3-one Type: Cholestane steroids. C27H42O4 mp 166–167 °C, [α]D28 = +9.0° (c = 0.11, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.22 μg/mL, KB, ED50 = 0.79 μg/mL, A549, ED50 = 0.58 μg/mL, HT29, ED50 = 0.47 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1997, 60, 900 O

OH

H

O OH

769 25-Hydroperoxy-6β-hydroxycholesta-4,23-dien-3-one Type: Cholestane steroids. C27H42O4 mp 159–160 °C, [α]D30 = +6.0° (c = 0.07, CHCl3). Source: Red alga Galaxaura marginata (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.28 μg/mL, KB, ED50 = 0.40 μg/mL, A549, ED50 = 1.00 μg/mL, HT29, ED50 = 0.68 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1997, 60, 900

2.3 Cholestane Steroids (C27)

H

O

305

OH

O OH

770 (24R)-Hydroxycholesta-4,22E-dien-3-one Type: Cholestane steroids. C27H42O2 Amorph. powder, [α]D25 = +47.6° (c = 0.2, CHCl3). Source: Gorgonian Dasystenella acanthina (psychrophilic, cold water, Antarctic). Pharm: Cytotoxic (LNCaP, GI50 = 2.0 μg/mL; SKBR3, GI50 = 3.2 μg/mL; SK-MEL-28, GI50 = 4.2 μg/mL; K562, GI50 = 1.1 μg/mL; PANC1, GI50 = 3.9 μg/mL; HT29, GI50 = 3.3 μg/mL; LoVo, GI50 = 3.6 μg/mL; LoVo-DOX, GI50 = 4.0 μg/mL; HeLa, GI50 = 4.5 μg/mL; cell growth inhibitor). Ref: G. G. Mellado, et al, Steroids, 2004, 69, 291│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) OH 24

H H H

H

O

771 3β-Hydroxycholesta-5,24-dien-23-one Type: Cholestane steroids. C27H42O2 Plates, mp 103–104 °C, [α]D = +12.8° (c = 1.9, MeOH). Source: Soft coral Gersemia fruticosa (psychrophilic, cold water, Arctic, Northern Russia). Pharm: Cytotoxic (against growth of K562, IC50 = 29 μmol/L); cytotoxic (antiproliferative against other leukemia cell lines: HL60, IC50 = 29 μmol/L, P388D1, IC50 = 21 μmol/L); apoptosis inducer. Ref: R. Koljak, et al, Tetrahedron, 1998, 54, 179│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

H

HO

O

306

2 Steroids

772 (20S)-20-Hydroxycholestane-3,16-dione Type: Cholestane steroids. C27H44O3 White solid. [α]D = −47.3° (c = 0.11, CHCl3). Source: Gorgonian Leptogorgia sarmentosa (Spain). Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all ED50s = 1 μg/mL). Ref: L. Garrido, et al, Steroids, 2000, 65, 85 OH H H H O

O H

H

773 16β-Hydroxy-5α-cholestane-3,6-dione Type: Cholestane steroids. C27H44O3 Source: Red alga Jania rubens (Tunisia). Pharm: Cytotoxic (KB, ID50 = 0.5 μg/mL). Ref: L. Ktari, et al, BoMCL, 2000, 10, 2563

H H

O

OH

H O

774 (20S)-20-Hydroxycholest-1-ene-3,16-dione Type: Cholestane steroids. C27H42O3 White solid. [α]D = −48.3° (c = 0.06, CHCl3). Source: Gorgonian Leptogorgia sarmentosa (Spain). Pharm: Cytotoxic (P388, A549, HT29 and MEL28, ED50 ≈ 1 μg/mL (using a fraction contained the compound)). Ref: L. Garrido, et al, Steroids, 2000, 65, 85 OH H H H O

O H

H

775 3β-Hydroxycholest-5-en-7-one Type: Cholestane steroids. C27H44O2 Cryst. (CHCl3/Et2O), mp 157 °C and 170 °C (double mp), [α]D = −108° (c = 0.9, CHCl3). Source: Sponges Cliona copiosa

2.3 Cholestane Steroids (C27)

307

(Burrowing sponge) and Damiriana hawaiiana. Pharm: Antineoplastic. Ref: C. Delseth, et al, Helv. Chim. Acta, 1978, 61, 1470

HO

O

776 22(R)-Hydroxy-3,16-dioxocholest-4-en-18-al Type: Cholestane steroids. C27H40O4 Source: Gorgonian Ctenocella sp. (New Caledonia). Pharm: Cytotoxic (KB, IC50 = 0.23 μg/mL, NSCLC-N6, IC50 = 2.9 μg/mL, against carcinoma cell proliferation). Ref: X. C. Fretté, et al, Tet. Lett., 1996, 37, 2959 OH 22R

O H H

O

O

777 Incrustasterol A Incrusterol A Type: Cholestane steroids. C27H44O5 [α]D = +42.7° (c = 1.0, MeOH). Source: Sponge Dysidea incrustans (Mediterranean Sea). Pharm: Cytotoxic (hmn non-small cell lung carcinoma, IC50 = 8 μg/mL, hmn renal carcinoma E39, IC50 = 11 μg/mL, hmn melanoma cell lines, IC50 = 11.3 μg/mL). Ref: A. Casapullo, et al, Tet. Lett., 1995, 36, 2669

H

O

HO

OH

OH OH

778 Incrustasterol B Incrusterol B Type: Cholestane steroids. C27H42O5 [α]D = +10.6° (c = 1.0, MeOH). Source: Sponge Dysidea incrustans (Mediterranean Sea). Pharm: Cytotoxic (hmn non-small cell lung carcinoma, IC50 = 21 μg/mL, hmn renal carcinoma E39, IC50 = 29 μg/mL, hmn melanoma cell lines, IC50 = 26.6 μg/mL). Ref: A. Casapullo, et al, Tet. Lett., 1995, 36, 2669

308

2 Steroids

H

O

O

HO

OH

OH

779 Isogosterone A Type: Cholestane steroids. C29H42O5 [α]D22 = +28.3° (c = 0.145, MeOH). Source: Soft coral Dendronephthya sp. (off Izu Peninsula, Japan). Pharm: Antifoulant (inhibits larval settlement of barnacle Balanus amphitrite, EC50 = 2.2 μg/mL). Ref: Y. Tomono, et al, JOC, 1999, 64, 2272 O O 19

H

21

18

O O

22 25

20

H O

780 Isogosterone B Type: Cholestane steroids. C29H42O7 [α]D22 = +60° (c = 0.135, MeOH). Source: Soft coral Dendronephthya sp. (off Izu Peninsula, Japan). Pharm: Antifoulant (inhibits larval settlement of barnacle Balanus amphitrite, EC50 = 2.2 μg/mL). Ref: Y. Tomono, et al, JOC, 1999, 64, 2272 O O OH 19

H H

O

OH O 22

O

781 Isogosterone C Type: Cholestane steroids. C31H46O8 [α]D22 = +51.4° (c = 0.26, MeOH). Source: Soft coral Dendronephthya sp. (off Izu Peninsula, Japan). Pharm: Antifoulant (inhibits larval settlement of barnacle Balanus amphitrite, EC50 = 2.2 μg/mL). Ref: Y. Tomono, et al, JOC, 1999, 64, 2272

2.3 Cholestane Steroids (C27)

309

O O

O OH

19

H

O

OH O 22

H O

782 Isogosterone D Type: Cholestane steroids. C31H44O7 [α]D22 = +34.3° (c = 0.210, MeOH). Source: Soft coral Dendronephthya sp. (off Izu Peninsula, Japan). Pharm: Antifoulant (inhibits larval settlement of barnacle Balanus amphitrite, EC50 = 2.2 μg/mL). Ref: Y. Tomono, et al, JOC, 1999, 64, 2272 O O

O O O H

O

O

783 Kurilensoside A 3-O-(2-O-Methyl-β-D-xylopyranosinyl)-(3β,4β,5α,6β,15α,24S)-Cholestane-3,4,6,8,15,24hexol 24-O-[ɑ-L-arabinofuranosyl-(1→2)-3-O-sulfo-ɑ-L-arabinofuranoside] Type: Cholestane steroids. C43H74O21S Amorph. powder, [α]D25 = −48° (c = 0.1, MeOH aq). Source: Starfish Hippasteria kurilensis. Pharm: Inhibits sea urchin egg fertilization (compound-preincubated sperm of sea urchin Strongylocentrotus nudus, EC100 = 8.9 × 10−5 mol/L). Ref: A. A. Kicha, et al, JNP, 2008, 71, 793 O H HO

OH

O

O S

O O

OH HO

OO OH

OH

OH O

H

OH HO

O OH

O

OH

310

2 Steroids

784 Kurilensoside B (3β,4β,5α,6α,7α,8β,15β,24S)-Cholestane-3,4,6,7,8,15,24-heptol 3-O-(2,4-di-O-methylβ-D-xylopyranoside) 24-O-[β-D-xylopyranosyl-(1→5)-ɑ-L-arabinofuranoside] Type: Cholestane steroids. C44H76O19 Amorph. powder, [α]D25 = −16.8° (c = 0.1, MeOH aq). Source: Starfish Hippasteria kurilensis. Pharm: Inhibits sea urchin egg fertilization (compound-preincubated sperm of sea urchin Strongylocentrotus nudus, EC100 = 5.5 × 10−5 mol/L). Ref: A. A. Kicha, et al, JNP, 2008, 71, 793 O 24S

H OH

OO

15

OH

O OH OH

OH OO OH

OH

H

OH

OH

OH

OH

O O

785 Kurilensoside C (3β,4β,5α,6α,7α,8β,15β,24S)-Cholestane-3,4,6,7,8,15,24-heptol 3-(2-O-methyl-β-Dxylopyranoside) 24-[2-O-methyl-β-D-xylopyranosyl-(1→5)-ɑ-L-arabinofuranoside] Type: Cholestane steroids. C44H76O19 Amorph. powder, [α]D25 = −23.2° (c = 0.1, MeOH aq). Source: Starfish Hippasteria kurilensis. Pharm: Inhibits sea urchin egg fertilization (compound-preincubated sperm of sea urchin Strongylocentrotus nudus, EC100 = 5.5 × 10−5 mol/L). Ref: A. A. Kicha, et al, JNP, 2008, 71, 793 O 24S

H OH

OO

15

OH

O OH OH

OH OO OH

OH

H

OH OH

OH O

OH O

786 Kurilensoside D (3β,4β,5α,6α,15β,24S)-Cholestane-3,4,6,8,15,24-hexol 24-O-[2-O-methyl-β-D-xylopyranosyl-(1→5)-ɑ-L-arabinofuranoside] Type: Cholestane steroids. C38H66O14 Amorph. powder, [α]D25 = −4.6° (c = 0.1, MeOH aq). Source: Starfish Hippasteria kurilensis. Pharm: Inhibits sea urchin egg fertilization (compound-preincubated sperm of sea urchin Strongylocentrotus nudus, EC100 = 6.7 × 10−5 mol/L). Ref: A. A. Kicha, et al, JNP, 2008, 71, 793

2.3 Cholestane Steroids (C27)

311

O 24S

H OH

O

OH

H

OH

OH

O OH

OH

OH HO

O OH

O

787 Lethasterioside A Type: Cholestane steroids. C56H92O27S Source: Starfish Leptasterias fusca (Posyet Bay, Sea of Japan). Pharm: Cytotoxic (weak), inhibits colony formation of tumour cells (soft agar clonogenic assay). Ref: N. V. Ivanchina, et al, Nat. Prod. Commun., 2012, 7, 853

H

O

H HO O

O

H

S

O O

OH HO

HO

HO

O

O O O

O

OH

O

O

H

O

OH

OH

OH

O

OH OH

OH OH

788 Linckoside L1 Type: Cholestane steroids. C33H58O10 Source: Starfish Linckia laevigata (Vietnam). Pharm: Nervous system activity (neurite outgrowth inducer, IC50 (apparent) = 0.3 μmol/L). Ref: A. A. Kicha, et al, Nat. Prod. Commun., 2007, 2, 41

312

2 Steroids

OH

H

OH

OH O O HO

OH

HO

OH

O

789 Linckoside L2 Type: Cholestane steroids. C33H58O8 Source: Starfish Linckia laevigata (Vietnam). Pharm: Nervous system activity (neurite outgrowth inducer, IC50 (apparent) = 0.3 μmol/L). Ref: A. A. Kicha, et al, Nat. Prod. Commun., 2007, 2, 41 OH

H

OH O O HO

HO

OH O

790 Marthasteroside B (3β,5α,6α)-3,6-Dihydroxycholesta-9(11),24-dien-23-one 6-O-[β-D-fucopyranosyl-(1→2)β-D-fucopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-D-quinovopyranosyl-(1→3)β-D-glucopyranoside] 3-sulfate Type: Cholestane steroids. C57H92O27S [α]D = +9° (MeOH). Source: Starfishes Coscinasterias tenuispina, Marthasterias glacialis, Luidia clathrata and Luidia maculata. Pharm: Molluscacidal. Ref: I. Bruno, et al, JCS Perkin I, 1984, 1875│R. Riccio, et al, Bull. Soc. Chim. Belg., 1986, 95, 869

2.3 Cholestane Steroids (C27)

H

313

O

H HO O

O S

O

H OO

HO BD-quinop

O

O OH

OH OO

HO OH

BD-fucop

O

O

OH HO OO BD-fucop OH

OH

BD-quinop

OH OH

OH

791 Mediasteroside M1 (3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24-pentol 24-O-[2-O-methyl-β-D-xylopyranosyl(1→5)-ɑ-L-arabinofuranoside] Type: Cholestane steroids. C38H66O13 Amorph. powder, [α]D = −36° (c = 0.3, MeOH). Source: Starfish Mediaster murrayi. Pharm: Cell division inhibitor (fertilized sea urchin eggs). Ref: A. A. Kicha, et al, JNP, 1999, 62, 279│ M. Inagaki, et al, CPB, 1999, 47, 1184

O 24

H OH

OO

15

OH

O OH O

OH HO

OH H

O

OH

792 Mediasteroside M2 (3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24-pentol 24-O-[β-D-xylopyranosyl-(1→5)-ɑ-Larabinofuranoside] Type: Cholestane steroids. C37H64O13 Amorph. powder, [α]D = −15.8° (c = 1.2, MeOH). Source: Starfish Mediaster murrayi. Pharm: Cell division inhibitor (fertilized sea urchin eggs). Ref: A. A. Kicha, et al, JNP, 1999, 62, 279│M. Inagaki, et al, CPB, 1999, 47, 1184

314

2 Steroids

O H OH

O OH

24

OO

15

O

OH OH HO

OH H

OH

OH

793 Mediasteroside M3 (3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24-pentol 24-O-[2,4-di-O-methyl-β-D-xylopyranosyl-(1→5)-ɑ-L-arabinofuranoside] Type: Cholestane steroids. C39H68O13 Amorph. powder, [α]D = −22.5° (c = 0.4, MeOH). Source: Starfish Mediaster murrayi. Pharm: Cell division inhibitor (fertilized sea urchin eggs). Ref: A. A. Kicha, et al, JNP, 1999, 62, 279│M. Inagaki, et al, CPB, 1999, 47, 1184 O 24

H OH

O OH

OO

15

O

OH OH HO

H

O O

OH

794 Mediasteroside M4 (3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24-pentol 24-O-[2,3-di-O-methyl-β-D-xylopyranosyl-(1→2)-ɑ-L-arabinofuranoside] Type: Cholestane steroids. C39H68O13 Amorph. powder, [α]D = −10.4° (c = 0.2, MeOH). Source: Starfish Mediaster murrayi. Pharm: Cell division inhibitor (fertilized sea urchin eggs). Ref: A. A. Kicha, et al, JNP, 1999, 62, 279│M. Inagaki, et al, CPB, 1999, 47, 1184 O H OH

15

OH HO

H

O OH

24

HO OO O OH

OH

O

795 6-Methoxycholest-7-ene-3,5-diol Type: Cholestane steroids. C28H48O3 [α]D = −55.6° (c = 0.19, CHCl3); [α]D = −159° (c = 0.02, CHCl3). Source: Sea hare Aplysia juliana (egg ribbons). Pharm: Cytotoxic (HeLa-S3, IC50 = 0.28 μg/mL). Ref: Y. Yamaguchi, et al, Chem. Lett., 1992, 1713

2.3 Cholestane Steroids (C27)

315

H

HO OH

O

796 (3β,4α,5α)-4-Methylcholest-8-en-3-ol Type: Cholestane steroids. C28H48O Cryst., mp 136.5–137 °C, [α]D = 55° (c = 1.85, CHCl3). Source: Sponges Agelas flabelliformis, Agelas oroides and Agelas dispar, microalga Porphyridium cruentum. Pharm: Immunosuppressive. Ref: R. B. Ramsey, et al, J. Biol. Chem., 1971, 246, 6393│CRC Press, DNP on DVD, 2012, version 20.2

H

HO

H

797 Minabeolide 4 Type: Cholestane steroids. C27H40O3 Colorless prisms, mp 261–262 °C, [α]D24 = +18° (c = 4.81, CHCl3). Source: Soft corals Paraminabea acronocephala (Pingtung county, Taiwan) and Minabea sp. Pharm: Anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 macrophage cells, inhibition of LPS induced iNOS expression, reduced iNOS to (23.2 ± 4.6)%; inhibition of LPS induced COX-2 expression, reduced COX-2 to (22.4 ± 9.9)%). Ref: M. B. Ksebati,et al, JOC, 1988, 53, 3926│C. -H. Chao, et al, JNP, 2011, 74, 1132

H O H H

O H

O

798 Minabeolide 5 Type: Cholestane steroids. C29H42O5 Colorless oil, [α]D24 = +13° (c = 1.56, CHCl3). Source: Soft corals Paraminabea acronocephala (Pingtung county, Taiwan) and Minabea sp. Pharm: Anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 macrophage cells, inhibition of LPS induced iNOS expression, reduced iNOS to (6.3 ± 1.5)%; inhibition of LPS induced COX-2 expression, reduced COX-2 to

316

2 Steroids

(31.3 ± 10.7)%). Ref: M. B. Ksebati,et al, JOC, 1988, 53, 3926│C. -H. Chao, et al, JNP, 2011, 74, 1132 O O H O H

O

H

H

O

799 Minabeolide 8 Type: Cholestane steroids. C29H44O5 Colorless prisms, mp 260–261 °C, [α]D24 = +37° (c = 0.28, CHCl3). Source: Soft corals Paraminabea acronocephala (Pingtung county, Taiwan) and Minabea sp. Pharm: Anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 macrophage cells, inhibition of LPS induced iNOS expression, reduced iNOS to ≈ 95%; inhibition of LPS induced COX-2 expression, reduced COX2 to ≈ 80%). Ref: M. B. Ksebati,et al, JOC, 1988, 53, 3926│C. -H. Chao, et al, JNP, 2011, 74, 1132 O O

H O H

O

H

H

O

800 Nebrosteroid N Type: Cholestane steroids. C29H48O4 White amorph. powder, [α]D25 = +12.8° (c = 0.1, CHCl3). Source: Soft coral Nephthea chabroli (Taitung County, Taiwan). Pharm: Cytotoxic (A549, ED50 = 6.7 μg/mL, control Mithramycin, ED50 = 0.18 μg/mL; HT29, ED50 = 9.5 μg/mL, Mithramycin, ED50 = 0.21 μg/mL; P388, ED50 = 0.9 μg/mL, Mithramycin, ED50 = 0.15 μg/mL; HEL, ED50 = 23.5 μg/mL). Ref: S. -K. Wang, et al, Mar. Drugs, 2012, 10, 1288 O H O

H H

HO

H OH

2.3 Cholestane Steroids (C27)

317

801 Nω-(3-Aminopropyl)-squalamine Trodusquemine Type: Cholestane steroids. C37H72N4O5S White powder. Source: Dogfish shark Squalus acanthias (from liver). Pharm: Antibacterial; appetite suppressant. Ref: M. N. Rao, et al, JNP, 2000, 63, 631 OH

O

S

O

O H H N

H HN N H

NH2

OH

802 Ophidianoside F (3β,5α,6α,20S)-3,6,20-Trihydroxycholest-9(11)-en-23-one 6-O-[β-D-fucopyranosyl-(1→2)β-D-xylopyranosyl-(1→4)-[6-deoxy-β-D-glucopyranosyl-(1→2)]-β-D-xylopyranosyl-(1→3)6-deoxy-β-D-glucopyranoside] 3-O-sulfate Type: Cholestane steroids. C55H90O27S [α]D = +0.4° (MeOH). Source: Starfishes Oreaster reticulatus, Ophidiaster ophidianus, Luidia clathrata, Linckia laevigata, Thromidia catalai and Cosmasterias lurida. Pharm: Antibarnacle. Ref: R. Riccio, et al, JCS Perkin I, 1985, 655; 1988, 1337 OH H O O HO

S

O

O

H OO O BD-glucp

BD-xylop O OH

OH

BD-xylop

OH

OO O

OH O OH HO

OH O

deoxy-BD-glucp

O

O

OH OH

OH BD-fucop

318

2 Steroids

803 Ophirapstanol trisulfate Type: Cholestane steroids. C31H56O12S3 Powder, [α]D24 = +17.3° (c = 0.12, MeOH). Source: Sponge Topsentia ophiraphidites (deep water). Pharm: Inhibits guanosine diphosphate/G-protein RAS exchange. Ref: S. P. Gunasekera, et al, JNP, 1994, 57, 1751

S

H

O

O O HO

H

O

HO

O

S

H

O

O

O

S

O

OH

804 Pandaroside C Type: Cholestane steroids. C39H60O15 Amorph. solid, [α]D20 = +35.2° (c = 0.1, MeOH). Source: Sponge Pandaros acanthifolium. Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 66.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 120 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 120 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 25 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6 cells, IC50 120 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: N. Cachet, et al, Steroids, 2009, 74, 746

O OH

H OH O O HO HO HO

HO

H O O

O

O OH

H

H

O

2.3 Cholestane Steroids (C27)

319

805 Pandaroside C methyl ester Type: Cholestane steroids. C40H66O15 Amorph. solid, [α]D20 = +24.8° (c = 0.1, MeOH). Source: Sponge Pandaros acanthifolium. Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 61.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 100 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 44.2 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 25 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 120 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: N. Cachet, et al, Steroids, 2009, 74, 746

O OH

H O O O HO

HO

H

O

H

O

O

HO

H O O

OH

HO

806 Pandaroside D Type: Cholestane steroids. C33H50O10 Amorph. solid, [α]D20 = +45.1° (c = 01, MeOH). Source: Sponge Pandaros acanthifolium. Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 15.3 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 80.8 μmol/L, control BenznidazoleIC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 31.0 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 13.5 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 96.6 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: N. Cachet, et al, Steroids, 2009, 74, 746

O OH

H OH O O HO

H O O

H

O

H

OH

807 Pandaroside D methyl ester Type: Cholestane steroids. C34H52O10 Amorph. solid, [α]D20 = +35° (c = 0.1, MeOH). Source: Sponge Pandaros acanthifolium. Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 40.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 21.6 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L);

320

2 Steroids

Antileishmanial (Leishmania donovani, IC50 = 13.7 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 5.1 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 106 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: N. Cachet, et al, Steroids, 2009, 74, 746

O OH

H O O O HO

H O O

H

O

H

OH

808 Phrygioside B (3β,5α,6α,15α,24S)-Cholestane-3,6,8,15,24-pentol 24-O-(3-O-Methyl-4-O-sulfo-β-Dxylopyranoside) Type: Cholestane steroids. C33H58O12S Amorph. solid, [α]D = −6.9° (c = 0.2, MeOH). Source: Starfish Hippasteria phrygiana (psychrophilic, cold water, Sea of Okhotsk, Russia). Pharm: Induces apoptosis (Ehrlich cell, EC50 = 70 μg/mL); inhibits Ca2+ influx into mouse splenocytes. Ref: E. V. Levina, et al, JNP, 2005, 68, 1541│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O OH O S O O

O O OH H

15

6

HO

H

OH OH

OH

809 Pinnasterol Type: Cholestane steroids. C27H42O5 Cryst., mp 198–201 °C. Source: Red alga Laurencia pinnata. Pharm: Ecdysone and may act to protect the alga from crustacean predators. Ref: A. Fukuzawa, et al, Tet. Lett., 1981, 22, 4085 OH OH H HO HO O

2.3 Cholestane Steroids (C27)

321

810 Punicinol A Type: Cholestane steroids. C29H50O5 Source: Leptogorgia punicea. Pharm: Synergistic cytotoxicity (for paclitaxel); cytotoxic (A549, cell growth inhibitor). Ref: M. Moritz, et al, Mar. Drugs, 2014, 12, 5864 H

HO H

HO

OH

H

H

O

O

811 Punicinol B Type: Cholestane steroids. C29H50O5 Source: Leptogorgia punicea. Pharm: Synergistic cytotoxicity (for paclitaxel); cytotoxic (A549, cell growth inhibitor). Ref: M. Moritz, et al, Mar. Drugs, 2014, 12, 5864 HO H H

HO

OH

H

H

O

O

812 Rathbunioside R1 (3β,5α,6α,15β,24S)-Cholestane-3,6,15,24-tetrol 24-O-β-D-xylopyranoside Type: Cholestane steroids. C32H56O8 Amorph. powder, [α]D = −0.2° (c = 1.6, MeOH). Source: Starfish Asterias rathbuni (psychrophilic, cold water, Bering Sea). Pharm: Cytotoxic (cell division inhibitor, fertilized sea urchin eggs, 7.0 × 10−5 mol/L). Ref: N. V. Ivanchina, et al, JNP, 2001, 64, 945│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) HO HO

O O OH

15

6

HO

H

OH

H

OH

322

2 Steroids

813 Rathbunioside R2 (3β,5α,6β,15α,24S)-Cholestane-3,5,6,15,24-pentol 24-O-β-D-xylopyranoside Type: Cholestane steroids. C32H56O9 Amorph. powder, [α]D = +13.1° (c = 0.45, MeOH). Source: Starfish Asterias rathbuni (psychrophilic, cold water, Bering Sea). Pharm: Cytotoxic (cell division inhibitor, fertilized sea urchin eggs, IC100 = 1.7 × 10−4 mol/L). Ref: N. V. Ivanchina, et al, JNP, 2001, 64, 945│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

O H

O

24S

OH

H

OH OH OH

HO

OH

OH

814 Riisein A Type: Cholestane steroids. C36H60O10 Powder, mp 187–189 °C, [α]D25 = −61° (c = 0.1, CHCl3). Source: Octocoral Telesto riisei (Brazil). Pharm: Cytotoxic (HCT116, ED50 = 2.0 μg/mL). Ref: L. F. Maia, et al, JNP, 2000, 63, 1427

H

O

O

H

O O HO

OH OH

HO O

O

815 Riisein B Type: Cholestane steroids. C36H60O10 Powder, mp 188–191 °C, [α]D25 = −85° (c = 0.1, CHCl3). Source: Octocoral Telesto riisei (Brazil). Pharm: Cytotoxic (HCT116, ED50 = 2.0 μg/mL). Ref: L. F. Maia, et al, JNP, 2000, 63, 1427

2.3 Cholestane Steroids (C27)

H

O

323

O

H

O

OH

O HO O

OH

O OH

816 Sepositoside A Type: Cholestane steroids. C45H70O18 Amorph. powder (Na salt), [α]D = −68.5° (c = 1, H2O) (Na salt). Source: Starfish Echinaster sepositus. Pharm: LD50 (mus, ipr) = 43 mg/kg. Ref: F. De Simone, et al, JCS Perkin I, 1981, 1855

H O OH

O

OO O

OH OH HO HO

O OH

O

OH

O OH

OH O

817 Stellettasterol 2β,3β,6β,11,19-Pentahydroxy-9,11-secocholestan-9-one Type: Cholestane steroids. C27H48O6 Solid, [α]D23 = −18.5° (c = 0.35, MeOH). Source: Sponge Stelletta sp. (Japan waters). Pharm: Antifungal (Mortieralla ramanniana, MIC = 12.5 μg/mL). Ref: H. Li, et al, Experientia, 1994, 50, 771 HO H HO

O

HO

H H

HO

H

OH

324

2 Steroids

818 Streptoseolactone Type: Cholestane steroids. C29H42O5 Source: Marine-derived streptomycete Streptomyces seoulensis from shrimp Penaeus orientalis (gut, Qingdao, China). Pharm: Neuraminidase inhibitor. Ref: R. H. Jiao, et al, J. Appl. Microbiol., 2013, 114, 1046

O

H O H HO

H

O OH

819 Thornasteroside A Ophidianoside E Type: Cholestane steroids. C56H92O28S Cryst. (butanol) (Na salt), mp 203–204 °C (Na salt), [α]D25 = −7° (c = 0.5, H2O). Source: Starfishes Acanthaster planci (Indo-Pacific Sea), Luidia maculata, Ophidiaster ophidianus, Linckia laevigata and Asterias amurensis cf. versicolor. Pharm: Hypotensive. Ref: I. Kitagawa, et al, Tet. Lett., 1977, 859; I. Kitagawa, et al, CPB, 1978, 26, 1864│T. Komori, et al, Liebigs Ann. Chem., 1983, 37│Y. Itakura, et al, Liebigs Ann. Chem., 1983, 2079│T. Komori, et al, Liebigs Ann. Chem., 1983, 2092│T. Komori, et al, Annalen, 1983, 24│L. Minale, et al, Comp. Biochem. Physiol., B, 1985, 80, 113│R. Riccio, et al, JCS Perkin I, 1985, 655; 1988, 1337│R. Riccio, et al, JNP, 1985, 48, 97 OH H O O

HO

S

O

O

BD-xylop

O OH

HO HO BD-galap

H OO O OH

O O

deoxy-BD-glucop OH

O

OH O OH

HO OO OH OH BD-fucop OH

deoxy-BD-glucop OH

2.3 Cholestane Steroids (C27)

325

820 3,6,24-Trihydroxycholestan-15-one Type: Cholestane steroids. C27H46O4 Cryst. (MeOH), [α]D20 = +9.1° (c = 0.6, EtOH). Source: Starfish Henricia sanguinolenta (psychrophilic, cold water). Pharm: Cytostatic (fertilized sea urchin eggs, moderate). Ref: E. V. Levina, et al, Russ. Chem. Bull., 2003, 52, 1623│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

OH

H

H

O

HO OH

821 Wondosterol B Type: Cholestane steroids. C38H62O13 Amorph. solid, [α]D23 = +46.2° (c = 0.5, MeOH). Source: Sponges Poecillastra wondoensis and Jaspis wondoensis (association). Pharm: Cytotoxic (P388, IC50 = 46 μg/mL). Ref: G, Ryu, et al, Tetrahedron, 1999, 55, 13171

H HO

HO

OH

O

O

HO

O OH

OH

O

HO OH OH

822 Wondosterol C Type: Cholestane steroids. C38H62O13 Amorph. solid, [α]D23 = +62.7° (c = 0.8, MeOH). Source: Sponges Poecillastra wondoensis and Jaspis wondoensis (association). Pharm: Antibacterial (Pseudomonas aeruginosa, Escherichia coli, 10 μg/disk); cytotoxic (P388, IC50 = 46 μg/mL). Ref: G, Ryu, et al, Tetrahedron, 1999, 55, 13171

326

2 Steroids

H HO HO

OH

O

O

HO

O OH O

OH

HO OH OH

823 Xestobergsterol A Type: Cholestane steroids. C27H44O5 Amorph. white powder. Source: Sponges Xestospongia bergquistia and Ircinia sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 4.0 μg/mL); inhibits anti-IgE-induced release of histamine (rat, mast cells, in vitro, IC50 = 0.05 μmol/L); antiallergic (IC50 = 262 μmol/L). Ref: N. Shoji, et al, JOC, 1992, 57, 2996│J. Kobayashi, et al, JNP, 1995, 58, 312│M. E. Jung, et al, Org. Lett., 1999, 1, 1671│M. E. Jung, et al, Tetrahedron, 2001, 57, 1449 H H H H

H

HO

OH

O

OH H OH

824 Xestobergsterol B Type: Cholestane steroids. C27H44O7 Amorph. white powder. Source: Sponges Xestospongia bergquistia and Ircinia sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 > 10 μg/mL, weak); inhibits anti-IgE-induced release of histamine (rat, mast cells). Ref: N. Shoji, et al, JOC, 1992, 57, 2996│J. Kobayashi, et al, JNP, 1995, 58, 312 H OH

H

HO

H H

HO

H OH

H OH

O

OH

2.4 Norcholestane and Dinorcholestane Steroids

327

825 Xestobergsterol C Type: Cholestane steroids. C27H44O6 Powder, [α]D22 = −18.6° (c = 0.38, MeOH). Source: Sponge Ircinia sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 4.1 μg/mL). Ref: J. Kobayashi, et al, JNP, 1995, 58, 312 H H

HO

H H

H

OH

O

OH

HO H OH

2.4 Norcholestane and Dinorcholestane Steroids 826 Astrosterioside D Type: Norcholestane and dinorcholestane steroids. C56H90O29S Source: Starfish Astropecten monacanthus (extracts, Cat Ba I., Haiphong, Vietnam). Pharm: Inhibitior of IL-6, IL-12 p40 and TNF-a production (potent). Ref: N. P. Thao, et al, JNP, 2013, 76, 1764 OH H O

O

H HO O

O S

H O O

HO HO HO

O

HO O

O O

O

OH

O OH

O O

OH O

OH

OH

HO

H

OH OH

827 7,8-Epoxy-26,27-dinorergost-23-ene-3,5,6-triol Type: Norcholestane and dinorcholestane steroids. C26H42O4 Cryst., mp 184–185 °C. Source: Gorgonian Acabaria undulata (Korea waters). Pharm: Cytotoxic (P388, IC50 = 28.7 μg/mL; DLD-1, IC50 = 24.6 μg/mL; PLA2, IC50 = 21.5 μg/mL). Ref: J. Shin, et al, JNP, 1996, 59, 679

328

2 Steroids

H

O HO

OH OH

828 Gelliusterol A (3β,7α)-26,27-Dinorcholest-5-en-23-yne-3,7-diol Type: Norcholestane and dinorcholestane steroids. C25H38O2 [α]D = −25.7° (c = 0.07, MeOH). Source: Sponge Gellius sp. (Caribbean coast of Panama). Pharm: Cytotoxic (P388, HT29, A549, DU145, and MEL28, IC50 > 1 μg/mL). Ref: W. A. Gallimore, et al, JNP, 2001, 64, 741

H H

HO

OH

829 Gelliusterol B 3β-Hydroxy-26,27-dinorcholest-5-en-23-yn-7-one Type: Norcholestane and dinorcholestane steroids. C25H36O2 [ɑ]D = −16.6° (c = 0.02, MeOH). Source: Sponge Gellius sp. (Caribbean coast of Panama). Pharm: Cytotoxic (P388, HT29, A549, DU145, and MEL28, IC50 > 1 μg/mL). Ref: W. A. Gallimore, et al, JNP, 2001, 64, 741

H H

HO

O

830 Glaciasterol A Type: Norcholestane and dinorcholestane steroids. C26H40O4 Amorph. solid. Source: Sponge Aplysilla glacialis (British Columbia). Pharm: Cytotoxic (L1210, ED50 = 7 μg/mL; hmn breast cancer cells, ED50 ≈ 20 μg/mL). Ref: J. Pika, et al, Can. J. Chem., 1992, 70, 1506

2.4 Norcholestane and Dinorcholestane Steroids

329

HO H

O

H HO

O

831 Halistanol sulfate B Type: Norcholestane and dinorcholestane steroids. C26H44O12S3 [α]D21 = +11.4° (c = 1, MeOH). Source: Sponge Epipolasis sp. (Japan waters). Pharm: Thrombin inhibitor (IC50 = 23 μg/mL). Ref: S. Kanazawa, et al, Tetrahedron, 1992, 48, 5467

O O

O O

S

H

OH H

O O S

H OH

O S

O OH

O

832 Halistanol sulfate D Type: Norcholestane and dinorcholestane steroids. C26H44O12S3 [α]D21 = +13.7° (c = 0.56, MeOH). Source: Sponge Epipolasis sp. (Japan waters). Pharm: Thrombin inhibitor (IC50 = 47 μg/mL). Ref: S. Kanazawa, et al, Tetrahedron, 1992, 48, 5467

O O

O O

S

OH H

O O S

H OH

O S

O OH

O

833 Hippasterioside D (20R,22R,23S)-22,23-Epoxy-20-hydroxy-6α-O-{β-D-xylopyranosyl-(1→3)-β-D-fucopyranosyl(1→2)-β-D-quinovopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-dxylopyranosyl-(1→3)-β-D-quinovopyranosyl}-24-nor-5α-cholest-9(11)-en-3β-yl sulfate Type: Norcholestane and dinorcholestane steroids. C60H98O30S Colorless amorph. powder, [α]D25 = ± 0° (c = 0.1, MeOH). Source: Starfish Hippasteria kurilensis (Kuril Is., Sea of Okhotsk, Russia). Pharm: Cytotoxic (HT29, inhibiting colony formation, reduced colony number by 23%). Ref: A. A. Kicha, et al, Chem. Biodiversity, 2011, 8, 166

330

2 Steroids

O

OH H H H

O HO S O O

OO

HO OO

OO HO

HO HO HO

HO HO

H

O

O

OO HO HO

O

O OH HO

OH

834 24-Hydroxy-26,27-dinorergosta-4,22E-dien-3-one Type: Norcholestane and dinorcholestane steroids. C26H40O2 Amorph. powder, [α]D25 = +45.9° (c = 0.07, CHCl3). Source: Gorgonian Dasystenella acanthina (psychrophilic, cold water, Antarctic). Pharm: Cytotoxic (LNCaP, GI50 = 1.4 μg/mL; SKBR3, GI50 = 3.3 μg/mL; SK-MEL-28, GI50 = 4.9 μg/mL; K562, GI50 = 0.9 μg/mL; PANC1, GI50 = 3.7 μg/mL; HT29, GI50 = 5.0 μg/mL; LoVo, GI50 = 3.5 μg/mL; LoVoDOX, GI50 = 4.4 μg/mL; cell growth inhibitor). Ref: G. G. Mellado, et al, Steroids, 2004, 69, 291│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) HO 24

H H H

H

O

2.5 A-nor-steroids 835 (2α,5α,11β,20R,22S,24S)-4(3→2)-Abeo-22,25-epoxy-11,20-dihydroxy24-methylfurostan-3-oic acid A-nor-22-epi-hippurin-2α-carboxylic acid Type: A-nor-steroids. C28H44O6 Cryst., mp 263–264 °C, [α]D25 = −20° (c = 1.04, MeOH). Source: Gorgonian Isis hippuris. Pharm: Cytotoxic (HepG2, ED50 = 3.6 μg/mL; Hep3B, ED50 = 6.9 μg/mL). Ref: J. -H. Sheu, et al, Tet. Lett., 2004, 45, 6413

2.6 Ecdysteroids

HO

331

O

HO H O

H

O

HO H

836 17R-Methylincisterol Volemolide Type: A-nor-steroids. C22H34O3 Needles, mp 61–62 °C, [α]D23 = +215° (c = 0.1, CHCl3); mp 62–64 °C, [α]D = +185.72° (c = 0.61, CHCl3). Source: Sponge Dictyonella incisa, deep-sea fungus Aspergillus sydowi YH11-2 (Guam, depth of 1000m, N13ʹ26ʹʹ,E144ʹ 43ʹʹ). Pharm: Cytotoxic (P388, IC50 = 18.57 μmol/L, control CDDP, IC50 = 0.039 μmol/L); LD50 (brine shrimp Artemia salina) = 6.6 ppm. Ref: P. Ciminiello, et al, JACS, 1990, 112, 3505│A. Kurek-Tylik, et al, JACS, 1995, 117, 1849│H. Mitome, et al, Tet. Lett., 1995, 36, 8231│F. De Riccardis, et al, Tet. Lett., 1995, 36, 4303│L. Tian, et al, Arch. Pharm. Res., 2007, 30, 1051│J. -M. Kornprobst, Encyclopedia of Marine Natural Products, 2 Edition, 2014, Vol2, P758, Wiley Blackwell

17R

H O O

H

O

2.6 Ecdysteroids 837 Crustecdysone (2β,3β,5β,20R,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one; Ecdysterone Type: Ecdysteroids. C27H44O7 Plates (EtOAc/THF), mp 237.5–239.5 °C, mp 243 °C, [α]D = +61.8° (CHCl3). Source: Zoanthid Gerardia savaglia, marine crayfish Jasus lalandei (low yield = 2 mg/ton), silkworm, terrestrial plants (Polypodium vulgare and many other plants). Pharm: Moulting hormone (crustacean); anti-inflammatory; antiarrhythmic; antiulcer. Ref: M. N. Galbraith, et al, Chem. Comm., 1966, 905│ A. Stuararo, et al, Experientia, 1982, 38, 1184

332

2 Steroids

OH

OH H

OH

HO OH HO

H

O

838 Muristerone A Type: Ecdysteroids. C27H44O8 Cryst. (MeOH), mp 238–240 °c, [α]D20 = +49.6° (c = 1, Py). Source: Sponge Ptilocaulis spiculifer. Pharm: Moulting hormone (insects, very high). Ref: M. Diop, et al, JNP, 1996, 59, 271 OH OH H

HO HO OH HO OH

O

2.7 Furostane Steroids (C27) 839 (22S)-3α-Acetoxy-11β,18α-dihydroxy-24-methyl-18,20β:22,25-diepoxy-5αfurostane Type: Furostane steroids. C30H46O7 Powder, mp 269–271 °C, [α]D = −43° (c = 0.31, CHCl3). Source: Gorgonian Isis hippuris. Pharm: Cytotoxic (HepG2, IC50 > 20 μg/mL; MCF7, IC50 = 12.72 μg/mL; MDA-MB-231, IC50 > 20 μg/mL). Ref: C. -H. Chao, et al, JNP, 2005, 68, 880 21

O

HO HO

O

H

5

H

O 16 8

H

28 25 22

H H

1

O

18

11

19

O

2.7 Furostane Steroids (C27)

333

840 3-Acetyl-2-desacetyl-22S-epi-hippurin 1 Type: Furostane steroids. C30H48O7 Cryst., mp 248–250 °C. Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (HepG2, IC50 = 2.06 μg/mL; Hep3B, IC50 = 1.46 μg/mL; MCF7, IC50 = 2.41 μg/mL; MDA-MB-231, IC50 = 0.74 μg/mL); cytotoxic (P388, A549, HT29, MEL28, all IC50 > 10 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487│C. -H. Chao, et al, JNP, 2005, 68, 880 21

O

HO 18

HO HO O

16 8

H

5

O

H

1

O

22

H 11

19

28 25

H

H

841 3-Acetyl-2-desacetyl-22R-epi-hippurin-1 3-Acetyl-2-desacetylhippurin 1 Type: Furostane steroids. C30H48O7 Powder, mp > 300 °C, [α]D = +27° (c = 0.3, CHCl3). Source: Gorgonian Isis hippuris. Pharm: Cytotoxic (HepG2, IC50 = 0.72 μg/mL; Hep3B, IC50 = 0.46 μg/mL; MCF7, IC50 = 1.07 μg/mL; MDA-MB-231, IC50 = 0.21 μg/mL). Ref: C. -H. Chao, et al, JNP, 2005, 68, 880 21

HO 18

HO

16 8

H

5

O

O

H

1

28 25 22

H 11

19

HO O

O

H

H

842 3-Acetyl-22-epi-hippuristanol Type: Furostane steroids. C30H48O6 Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL; A549, IC50 = 0.125 μg/mL; HT29, IC50 = 0.5 μg/mL; MEL28, IC50 = 0.125 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487

HO HO

H H

O

H O H

H

O

H

O

334

2 Steroids

843 11-Dehydroxy-22-epi-hippuristanol Type: Furostane steroids. C28H46O4 Powder, [α]D26 = −23.1° (c = 0.625, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 = 5 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487

HO

O H

O

H H HO

22

H

H

844 11-Dehydroxy-22-epi-hippuristanol-3-one Type: Furostane steroids. C28H44O4 Powder, [α]D26 = −41.5° (c = 0.03, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 = 5 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487

HO

O H

H H O

22

O

H

H

845 2-Desacetyl-22S-epi-hippurin 1 Type: Furostane steroids. C28H46O6 Cryst., mp 260–261 °C. Source: Gorgonian Isis hippuris. Pharm: Cytotoxic (HepG2, IC50 = 0.62 μg/mL; Hep3B, IC50 = 0.77 μg/mL; MCF7, IC50 = 0.59 μg/mL; MDA-MB-231, IC50 = 0.75 μg/mL). Ref: T. Higa, et al, Chem. Lett., 1981, 1647│C. -H. Chao, et al, JNP, 2005, 68, 880

21 28

HO 18

HO

O

H

16

HO 1

H

5

H

8

H

25 22

H 11

19

HO

O

2.7 Furostane Steroids (C27)

335

846 (22S)-2α,3α-Diacetoxy-11β,18α-dihydroxy-24-methyl-18,20β:22,25-diepoxy5α-furostane Type: Furostane steroids. C32H48O9 Powder, mp 273–275 °C, [α]D = −23° (c = 0.38, CHCl3). Source: Gorgonian Isis hippuris. Pharm: Cytotoxic (HepG2, IC50 > 20 μg/mL; MCF7, IC50 = 11.39 μg/mL; MDA-MB-231, IC50 > 20 μg/mL). Ref: C. -H. Chao, et al, JNP, 2005, 68, 880

21

O

19

O

18

11

HO

28

O

O

HO

25 22

H O

H

16

O 1

H

5

O

8

H

H

847 Hippurin 1 22,25-Epoxy-24-methylfurostane-2-acetoxy-,3,11,20-tirol Type: Furostane steroids. C30H48O7 Cryst. (H2O/petrol), mp 183–185 °C, [α]D = +36.2° (c = 1, CHCl3). Source: Gorgonian Isis hippuris. Pharm: Cytotoxic (HepG2, IC50 = 0.56 μg/mL; Hep3B, IC50 = 0.10 μg/mL; MCF7, IC50 = 0.53 μg/mL; MDA-MB-231, IC50 = 0.41 μg/mL). Ref: R. Kazlauskas, et al, Tet. Lett., 1977, 18, 4439│T. Higa, et al, Chem. Lett., 1981, 1647│C. B. Rao, et al, JNP, 1988, 51, 954│C. -H. Chao, et al, JNP, 2005, 68, 880

21

HO O

18

HO

H 11

19

H

O 1

H

5

O

28 25 22

O

16 8

H

HO H

848 22-epi-Hippurin 1 Type: Furostane steroids. C30H48O7 Cryst. (MeOH), mp 243–245 °C. Source: Gorgonian Isis hippuris. Pharm: Cytotoxic (HepG2, IC50 = 4.64 μg/mL; Hep3B, IC50 = 0.68 μg/mL; MCF7, IC50 = 4.54 μg/mL; MDA-MB-231, IC50 = 2.64 μg/mL). Ref: T. Higa, et al, Chem. Lett., 1981, 1647│C. -H. Chao, et al, JNP, 2005, 68, 880

336

2 Steroids

21

O

HO 18

HO

O

O

H

O 1

16 8

H

5

22

H 11

19

28 25

H

HO H

849 Hippuristanol Type: Furostane steroids. C28H46O5 Cryst. (MeOH), mp 188–190 °C. Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, IC50 = 0.1 μg/mL; A549, IC50 = 0.1 μg/mL; HT29, IC50 = 0.1 μg/mL; MEL28, IC50 = 0.1 μg/mL). Ref: T. Higa, et al, Chem. Lett., 1981, 1647│C. B. Rao, et al, JNP, 1988, 51, 954│N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487

O

HO HO

22R

H H

HO

O

H

850 22-epi-Hippuristanol Type: Furostane steroids. C28H46O5 Cryst. (MeOH), mp 248–249 °C. Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (HepG2, IC50 = 0.08 μg/mL; Hep3B, IC50 = 0.10 μg/mL; MCF7, IC50 = 0.20 μg/mL; MDA-MB-231, IC50 = 0.13 μg/mL); cytotoxic (P388, IC50 = 0.1 μg/mL; A549, IC50 = 0.1 μg/mL; HT29, IC50 = 0.1 μg/mL; MEL28, IC50 = 0.1 μg/mL). Ref: T. Higa, et al, Chem. Lett., 1981, 1647│N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487│C. -H. Chao, et al, JNP, 2005, 68, 880 21

HO 18

HO

1

H

5

H

O

H

16 8

H

28 25 22

H 11

19

HO

O

2.7 Furostane Steroids (C27)

337

851 22ξ-Hydroxyfurosta-1,4-dien-3-one Type: Furostane steroids. C27H40O3 White solid, mp 123–124°, [α]D = −10.2° (c = 0.5, CHCl3). Source: Soft coral Alcyonium gracillimum (Korea waters). Pharm: Cytotoxic (moderate); antiviral (moderate). Ref: Y. Sco, et al, Tetrahedron, 1995, 51, 2497 OH H H

O

O

852 22ξ-Hydroxyfurost-1-en-3-one Type: Furostane steroids. C27H42O3 Solid, mp 43–45 °C, [α]D = −3.8° (c = 0.5, CHCl3). Source: Soft coral Alcyonium gracillimum (Korea waters). Pharm: Cytotoxic (P388, IC50 = 22.4 μg/mL); antiviral (HSV-1); antiviral (hmn cytogalovirus, IC50 = 3.7 μg/mL). Ref: Y. Seo, et al, Tetrahedron, 1995, 51, 2497 OH H H

O

O

853 2α-Hydroxyhippuristanol Type: Furostane steroids. C28H46O6 Amorph. solid. Source: Gorgonian Isis hippuris. Pharm: Antineoplastic. Ref: T. Higa, et al, Chem. Lett., 1981, 1647

HO HO

HO

H H

HO

O

O

H

854 Manadosterol A Type: Furostane steroids. C55H90O20S5 Source: Sponge Lissodendoryx fibrosa (North Sulawesi, Indonesia). Pharm: Inhibitor of ubiquitin Ubc13-Uev1a complex (potential as anticancer agent, potent). Ref: S. Ushiyama, et al, JNP, 2012, 75, 1495

338

2 Steroids

OH O

H

S O O

O O

S

O

OH

H

H

H O

H

H O

O O

S

S

Z

H OH

H

O O H

OH

H O

H

O

S

OH

O

855 Manadosterol B Type: Furostane steroids. C55H90O20S5 Source: Sponge Lissodendoryx fibrosa (North Sulawesi, Indonesia). Pharm: Inhibitor of ubiquitin Ubc13-Uev1a complex (potential as anticancer agent, potent). Ref: S. Ushiyama, et al, JNP, 2012, 75, 1495

OH O

H

S O O H

S OH

E

H O

O O

H

H

O

H O

O O S

S

H OH H

O O H

OH H

H O

O

S

OH

O

856 (22S,24S)-24-Methyl-22,25-epoxyfurost-5-ene-3β,20β-diol Type: Furostane steroids. C28H44O4 White powder, mp 213–216 °C, [α]D25 = −38.1° (c = 0.001, CHCl3). Source: Soft corals Lobophytum laevigatum (Khanh Hoa province, Vietnam) and Sarcophyton crassocaule (Andaman and Nicobar Is., Indian Ocean). Pharm: Cytotoxic (A549, IC50 > 20 μmol/L, control Mitoxantrone, IC50 = (7.8 ± 0.4) μmol/L; HCT116, IC50 = (6.9 ± 0.8)μmol/L, Mitoxantrone, IC50 = (7.2 ± 0.3)μmol/L; HL60, IC50 > 20 μmol/L, Mitoxantrone, IC50 = (8.2 ± 0.9)μmol/L); upregulats PPARs transcription (HepG2, dose-dependent). Ref: A. S. R. Anjaneyulu, et al, J. Chem. Res., Synop., 1997, 450; J. Chem. Res., Miniprint, 2743│T. H. Quang, et al, BoMCL, 2011, 21, 2845

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

HO

339

O H

H

O

HO

2.8 Ergostane Steroids (Excluding Withanolides) (C28) 857 Acanthifolioside A Type: Ergostane steroids. C33H52O7 White amorph. solid, [α]D20 = −87.3° (c = 0.14, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Cytotoxic (L-6, IC50 = 25.9 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L); antiprotozoal (Trypanosoma brucei rhodesiense, IC50 = 94.8 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 27.6 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L; Leishmania donovani, IC50 = 20.7 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L; Plasmodium falciparum, IC50 = 21.6 μmol/L, control Chloroquine, IC50 = 0.20 μmol/L). Ref: E. L. Regalado, et al, Tetrahedron, 2011, 67, 1011

H H H HO

O H

O

OH

HO O

OH

858 Acanthifolioside B Type: Ergostane steroids. C33H54O7 White amorph. solid, [α]D20 = −22.5° (c = 0.16, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Cytotoxic (L-6, IC50 = 42.3 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L); antiprotozoal (Trypanosoma brucei rhodesiense, IC50 = 32.0 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 28.6 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L; Leishmania donovani, IC50 = 8.5 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L; Plasmodium falciparum, IC50 = 7.6 μmol/L, control Chloroquine, IC50 = 0.20 μmol/L). Ref: E. L. Regalado, et al, Tetrahedron, 2011, 67, 1011

340

2 Steroids

H H H

OH H

O

OH

HO O

HO

OH

859 Acanthosterol sulfate I Type: Ergostane steroids. C30H48O8S [α]D25 = −11° (c = 0.15, MeOH). Source: Sponge Acanthodendrilla sp. (Japan waters). Pharm: Antifungal (yeast Saccharomyces cerevisiae A364A strain, IZD = 7 mm; STX338-2C strain, IZD = 8 mm; 14028g strain, IZD = 9 mm; GT160-45C strain, inactive; RAY-3Aa strain, inactive). Ref: S. Tsukamoto, et al, JNP, 1998, 61, 1374 O H O O

HO O HO

S

O

O

860 Acanthosterol sulfate J Type: Ergostane steroids. C30H48O8S [α]D25 = −25° (c = 0.092, MeOH). Source: Sponge Acanthodendrilla sp. (Japan waters). Pharm: Antifungal (yeast Saccharomyces cerevisiae A364A strain, IZD = 11 mm; STX338-2C strain, IZD = 10 mm; 14028g strain, IZD = 11 mm; GT160-45C strain, inactive; RAY-3Aa strain, inactive). Ref: S. Tsukamoto, et al, JNP, 1998, 61, 1374 O H O O HO O HO

S O

O

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

341

861 Acodontasteroside E (3β,4β,5α,6α,8β,15β,22E,24R,25S)-Ergost-22-ene-3,4,6,8,15,26-hexol 26-O-[2-O-methyl -β-D-xylopyranosyl-(1→2)-β-D-xylopyranoside] Type: Ergostane steroids. C39H66O14 Source: Starfish Acodontaster conspicuus (Antarctic). Pharm: Antibacterial (Antarctic marine bacteria McM13.3 and McM32.2, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, JNP, 1997, 60, 959

25S

H

24R

O

O

OH

OH

OH O

OH HO OH

H

O

OH OH OH O

862 Acodontasteroside G Type: Ergostane steroids. C39H66O14 [α]D = −14.4° (c = 1, MeOH). Source: Starfish Acodontaster conspicuus (Antarctic). Pharm: Antibacterial (Antarctic marine bacterium McM32.2, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, JNP, 1997, 60, 959

OO

H OH OH OH OH

OO

OH

HO OH

OH

OH O

863 Acodontasteroside H (3β,6α,15β,22E,24R,25S)-Ergosta-8(14),22-diene-3,6,15,26-tetrol 26-O-[2-O-Methyl-β-Dxylopyranosyl-(1→2)-β-D-xylopyranoside] Type: Ergostane steroids. C39H64O12 [α]D = −21.7° (c = 1, MeOH). Source: Starfish Acodontaster conspicuus (Antarctic). Pharm: Antibacterial (Antarctic marine bacterium McM11.5, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, JNP, 1997, 60, 959

342

2 Steroids

25S

O O

24R

H

OH OH OO

OH

OH

HO OH

OH O

864 Agosterol A4 Type: Ergostane steroids. C34H52O8 [α]D = +17.5° (c = 0.9, CHCl3). Source: Sponge Spongia sp. (Japan waters). Pharm: Reversal of MDR (3 μg/mL: KB-C2, InRt = (78 ± 4)%; KB-CV60, InRt = (75 ± 1)%; KB-3-1, InRt = (1 ± 1)%). Ref: S. Aoki, et al, Tetrahedron, 1999, 55, 13965 OH

H

HO

O O O

O

H

O

O

865 Agosterol A5 Type: Ergostane steroids. C35H54O8 [α]D = +8.2° (c = 0.3, CHCl3). Source: Sponge Spongia sp. (Japan waters). Pharm: Reversal of MDR (10 μg/mL: KB-C2, InRt = (90 ± 1)%; KB-CV60, InRt = (54 ± 7)%; KB-3-1, InRt = (23 ± 7)%). Ref: S. Aoki, et al, Tetrahedron, 1999, 55, 13965

H

HO

OH O O O

O

H

O

O

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

343

866 Anicequol Type: Ergostane steroids. C30H48O6 Needles， mp 174–175 °C, [α]D23 = +67.1° (c = 1, CHCl3/MeOH). Source: Marine-derived fungus Penicillium chrysogenum from red alga Laurencia sp., terrestrial fungus (Penicillium aurantiogriseum). Pharm: Antifungal (20 μg/disk, Aspergillus niger, slight inhibition, control AMPB, IZD = 24 mm, Alternaria brassicae, IZD = 6 mm, control AMPB, IZD = 16 mm); cytotoxic (anchorageindependent tumour growth inhibitor). Ref: Y. Igarashi, et al, J. Antibiot., 2002, 55, 371│S. -S. Gao, et al, BoMCL, 2011, 21, 2894

H

HO H

16

O O

HO

OH

H O

867 Annasterol sulfate Type: Ergostane steroids. C30H48O6S Cryst., mp 149–150 °C, [α]D = +28.6° (c = 0.35, MeOH). Source: Sponge Poecillastra laminaris (deep water, Pacific Ocean). Pharm: Endo-β-1,3-glucanases L0 inhibitor (1.0 μg/0.02 unit of activity); endo-β-1,3glucanases LIV4 inhibitor (2.8 μg/0.02 unit of activity). Ref: T. N. Makarieva, et al, Tet. Lett., 1995, 36, 129

H

O HO S

O

O

O O

868 asperversin A Type: Ergostane steroids. C47H58O10 Yellow cryst., mp 273–275 °C, [α]D25 = −309.7° (c = 0.12, CHCl3). Source: Marine-derived fungus Aspergillus versicolor from brown alga Sargassum thunbergii (Pingtan I., Fujian, China). Pharm: Antibacterial (30 μg/ disk: Escherichia coli, IZD = 7 mm, control Chloramphenicol, IZD = 32 mm; Staphylococcus aureus, IZD = 7 mm, Chloramphenicol, IZD = 31 mm); toxic (brine shrimp Artemia salina, 30 μg/disk, Lethal Rate = 1.8%). Ref: G. -Y. Li, et al, Org. Lett., 2009, 11, 3714│F. -P. Miao, et al, Mar. Drugs, 2012, 10, 131

344

2 Steroids

H

H

H O

O O O O

H O

O

O

O

OH

869 Asteriidoside L Type: Ergostane steroids. C33H56O12S [α]D = +5.7° (c = 1, MeOH). Source: An unidentified starfish (family Asteriidae, Antarctic). Pharm: Cytotoxic (NSCLC-L16, IC50 > 30 μg/mL). Ref: S. De Marino, et al, JNP, 1998, 61, 1319 O HO

S O O

H OH HO

O

HO

OH O

OH

OH

870 Biemnasterol Ergosta-7,22,25-triene-3,5,6-triol; 24-Methylcholesta-7,22,25-triene-3,5,6-triol Type: Ergostane steroids. C28H44O3 Cryst., mp 241–242 °C, [α]D19 = −7.6° (c = 0.43, MeOH). Source: Sponge Biemna sp. (Okinawa). Pharm: Cytotoxic (L1210, IC50 = 3.0 μg/mL; KB, IC50 = 1.3 μg/mL). Ref: C. Zeng, et al, JNP, 1993, 56, 2016

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

22

345

24

H

3

HO

5

6

OH OH

871 Cerevisterol Ergosta-7,22-diene-3β,5α,6β-triol Type: Ergostane steroids. C28H46O3 Cryst. (MeOH), mp 245–247 °C. Source: Deep-sea fungus Aspergillus sydowi YH11-2 (Guam, depth of 1000m, N13ʹ26ʹʹ,E144ʹ 43ʹʹ), deep-sea fungus Penicillium commune SD-118, marine-derived fungus Aspergillus versicolor from brown alga Sargassum thunbergii (Pingtan I., Fujian, China), sponges Dictyonella incisa and Spongionella gracilis., gorgonian Junceella juncea (Indian Ocean), crinoid Gymnocrinus richeri, bryozoan Myriapora truncata. Pharm: Cytotoxic (P388, IC50 = 0.12 μmol/L, control CDDP, IC50 = 0.039 μmol/L). Ref: F. Cafieri, et al, JNP, 1985, 48, 944│ V. J. Piccialli, Nat. Prod., 1987, 50, 915│H. Kawagishi, et al, Phytochemistry, 1988, 27, 2777│P. Ciminiello, et al, JACS, 1990, 112, 3505│A. S. R. Anjaneyulu, et al, JCS Perkin I, 1997, 959│P. -J. Sung, et al, Biochemical Systematics and Ecology, 2004, 32, 185 (rev)│L. Tian, et al, Arch. Pharm. Res., 2007, 30, 1051│F. -P. Miao, et al, Mar. Drugs, 2012, 10, 131│Z. Shang, et al, Chin. J. Oceanol. Limnol., 2012, 30, 305

H

HO

OH OH

872 Chabrosterol Type: Ergostane steroids. C27H42O2 Amorph. powder, [α]D25 = +28.5° (c = 0.1, CHCl3). Source: Soft coral Nephthea chabroli (extract, Siaoliouciou I., Taiwan). Pharm: Antiinflammatory (10 μmol/L, reduced level of iNOS protein (12.4 ± 2.9)%, reduced level of COX-2 protein (45.2 ± 5.4)%). Ref: S. -Y. Cheng, et al, Tet. Lett., 2009, 50, 802

346

2 Steroids

H H H HO

H O

873 Conicasterol B Type: Ergostane steroids. C29H44O Pale yellow oil, [α]D25 = +29° (c = 0.06, MeOH). Source: Lithistid sponge Theonella swinhoei (South China Sea; Malaita I. and Vangunu I., Solomon Is.). Pharm: Affects nuclear receptors (using HepG2 cell transfected with FXR or PXR, antagonist of FXR transactivation by chenodeoxycholic acid; agonist of PXR at 10 μmol/L); PXR agonist and FXR antagonist (Exposure of liver cells to this agent resulted in potent induction of PXR regulated genes and modulation of FXR regulated genes, highlighting its pharmacological potential in treatment of liver disorders). Ref: S. De Marino, et al, JMC, 2011, 54, 3065│ P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

HO

24

H

874 Conicasterol C Type: Ergostane steroids. C30H50O3 White amorph. solid, [α]D25 = +43° (c = 0.13, MeOH). Source: Lithistid sponge Theonella swinhoei (Malaita I. and Vangunu I., Solomon Is.). Pharm: PXR agonist; FXR antagonist. Ref: S. De Marino, et al, JMC, 2011, 54, 3065

H

O HO

H

OH

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

347

875 Conicasterol D Type: Ergostane steroids. C29H48O3 White amorph. solid, [α]D25 = +33° (c = 0.08, MeOH). Source: Lithistid sponge Theonella swinhoei (Malaita I. and Vangunu I., Solomon Is.). Pharm: PXR agonist; FXR antagonist. Ref: S. De Marino, et al, JMC, 2011, 54, 3065

H

OH

OH

HO H

876 Crassarosterol A Type: Ergostane steroids. C28H46O3 White powder, [α]D24 = −45° (c = 0.66, CHCl3). Source: Soft coral Sinularia crassa (Taitung county, Taiwan). Pharm: Cytotoxic (HepG2, IC50 = 14.9 μmol/L; HepG3, MCF7, MDA-MB-231 and A549, inactive); antiinflammatory antidromic action (immunoblot analysis, RAW264.7 cells, 10 μmol/L, stimulates expression of COX-2 protein). Ref: C. -H. Chao, et al, Mar. Drugs, 2012, 10, 439

H

HO H H

OH H

HO

877 Crassarosteroside A Type: Ergostane steroids. C36H58O8 White powder, [α]D24 = −34° (c = 0.18, CHCl3). Source: Soft coral Sinularia crassa (Taitung county, Taiwan). Pharm: Antiinflammatory antidromic action (immunoblot analysis, RAW264.7 cells, 10 μmol/L, stimulates expression of COX-2 protein); anti-inflammatory (immunoblot analysis, RAW264.7 cells, 10 μmol/L, inhibits expression of iNOS protein). Ref: C. -H. Chao, et al, Mar. Drugs, 2012, 10, 439

348

2 Steroids

H

HO H

HO

O

HO

H

OH H

O O O

878 Crassarosteroside B Type: Ergostane steroids. C36H58O8 White powder, [α]D24 = −17° (c = 0.16, CHCl3). Source: Soft coral Sinularia crassa (Taitung county, Taiwan). Pharm: Antiinflammatory antidromic action (immunoblot analysis, RAW264.7 cells, 10 μmol/L, stimulates expression of COX-2 protein). Ref: C. -H. Chao, et al, Mar. Drugs, 2012, 10, 439

H

HO H

HO O

O

O

H

OH H

O OH

879 Crassarosteroside C Type: Ergostane steroids. C36H58O8 White powder, [α]D24 = −52° (c = 0.18, CHCl3). Source: Soft coral Sinularia crassa (Taitung county, Taiwan). Pharm: Cytotoxic (HepG2, IC50 = 17.6 μmol/L; HepG3, IC50 = 18.9 μmol/L; MCF7, MDA-MB-231 and A549, inactive); anti-inflammatory (immunoblot analysis, RAW264.7 cells, 10 μmol/L, inhibits expression of iNOS protein). Ref: C. -H. Chao, et al, Mar. Drugs, 2012, 10, 439

H

HO

O

H

O

O

HO

H O

OH

OH H

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

349

880 Dankasterone A Type: Ergostane steroids. C28H40O3 Cryst. (MeOH), mp 133–134 °C, [α]D26 = +57.8° (c = 0.7, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica (Japan waters). Pharm: Cytotoxic (P388, ED50 = 2.2 μg/mL, inhibits growth significantly; hmn cancer cell lines, potent growth inhibition). Ref: T. Amagata, et al, Chem. Comm., 1999, 1321│C. Le, et al, Chin. J. Mar. Drugs. 1999, 18(2), 12│T. Amagata, et al, JNP, 2007, 70, 1731

H

O

O O

881 Dankasterone B Type: Ergostane steroids. C28H42O3 Powder, mp 182–183 °C, [α]D22 = +38.4° (c = 0.2, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica (Japan waters). Pharm: Cytotoxic (P388, inhibits growth significantly). Ref: T. Amagata, et al, JNP, 2007, 70, 1731

H

O

H

O O

882 Dehydroconicasterol 4-Methyleneergosta-8(14),24(28)-dien-3-ol Type: Ergostane steroids. C29H46O Amorph. solid, [α]D = +82° (c = 0.2, CHCl3). Source: Lithistid sponge Theonella swinhoei (South China Sea; Bunaken Marine Park, Indonesia). Pharm: Cytotoxic (C6, HeLa and H9c2, MIC = 70 μmol/L). Ref: R. F. Angawi, et al, JNP, 2009, 72, 2195│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

H HO

H

350

2 Steroids

883 9(11)-Dehydroergosterol peroxide 5α,8α-epi-Dioxy-24(R)-methylcholesta-6,9(11),22-trien-3β-ol Type: Ergostane steroids. C28H42O3 Source: Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters), terrestrial plant (Typha latifolia), deep-sea fungus Paecilomyces lilacinus ZBY-1. Pharm: Cytotoxic (MTT assay: P388, IC50 = 7.3 μmol/L; HL60, IC50 = 4.5 μmol/L; SRB assay: A549, IC50 = 60.7 μmol/L; Bel7402, IC50 = 73.1 μmol/L); cytotoxic (K562, MCF7, HL60 and BGC823 cells, IC50 = 22.3–139.0 μmol/L). Ref: F. Wang, et al, Steroids, 2008, 73, 19│X. Cui, et al, J. Int. Pharm. Res., 2013, 40, 177 (in Chinese)

H

O

O

H

HO

884 15-Dehydroxyconicasterol C Type: Ergostane steroids. C30H50O2 Source: Lithistid sponge Theonella swinhoei (South China Sea). Pharm: Affects nuclear receptors (using HepG2 cell transfected with FXR or PXR, antagonist of FXR transactivation by chenodeoxycholic acid; agonist of PXR at 10 μmol/L). Ref: P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

O HO

H

885 15-Dehydroxyconicasterol D Type: Ergostane steroids. C29H48O2 Source: Lithistid sponge Theonella swinhoei (South China Sea). Pharm: Affects nuclear receptors (using HepG2 cell transfected with FXR or PXR, antagonist of FXR transactivation by chenodeoxycholic acid; agonist of PXR at 10 μmol/L). Ref: P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

OH HO

H

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

351

886 29-Demethylgeodisterol-3-O-sulfate Type: Ergostane steroids. C27H40O6S Amorph. solid, [α]D29 = +14.5° (c = 0.18, MeOH). Source: Sponge Topsentia sp. (Chuuk, Micronesia). Pharm: Antifungal (Candida albicans and Saccharomyces cerevisiae, MMOA: MDR1 efflux pump inhibition). Ref: J. A. DiGirolamo, et al, JNP, 2009, 72, 1524 OH H H OH

H

O O

S

OH H

O

887 Desulfohaplosamate Type: Ergostane steroids. C30H53O9P Source: Sponge Dasychalina sp. (Bunaken Marine Park, Manado, Indonesia). Pharm: Cannabinoid CB2-receptor ligand (selective). Ref: G. Chianese, et al, Steroids, 2011, 76, 998

H H HO OH

H

O

H H

O P OH O

O

OH OH

888 3β,15a-Dihydroxy-(22E,24R)-ergosta-5,8(14),22-trien-7- one Type: Ergostane steroids. C28H42O3 Amorph. powder, [α]D21 = −217° (c = 0.12, CHCl3). Source: Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters). Pharm: Cytotoxic (MTT assay: P388, IC50 = 1.48 μmol/L; HL60, IC50 = 0.3 μmol/L; SRB assay: A549, IC50 = 4.9 μmol/L; Bel7402, IC50 = 5.2 μmol/L). Ref: F. Wang, et al, Steroids, 2008, 73, 19

H

H HO

OH O

352

2 Steroids

889 3β,15β-Dihydroxy-(22E,24R)-ergosta-5,8(14),22-trien-7-one Type: Ergostane steroids. C28H42O3 Amorph. powder, [α]D21 = −144° (c = 0.12, CHCl3). Source: Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters). Pharm: Cytotoxic (MTT assay: P388, IC50 = 1.8 μmol/L; HL60, IC50 = 0.5 μmol/L; SRB assay: A549, IC50 = 36.1 μmol/L; Bel7402, IC50 = 38.5 μmol/L). Ref: F. Wang, et al, Steroids, 2008, 73, 19

H

H HO

OH O

890 (3β,5α,6α,22E,24ξ)-3,6-Diihydroxy-11-acetoxy-27-nor-9,11-secoergosta7,22-dien-9-one Type: Ergostane steroids. C29H46O5 Oil, [α]D20 = +27° (c = 0.2, CHCl3). Source: Gorgonian Eunicella cavolini (Lichadonissia I., Greece). Pharm: Cytotoxic (MTT assay, 10 μmol/L: LNCaP cells in MEM+ 10% FBS, Growth inhibition InRt = (83 ± 2)%, IC50 = (5.4 ± 0.7)μmol/L; MCF7 cells in MEM+ 10% FBS, Growth inhibition InRt = (49 ± 6)%, IC50 = (7.0 ± 0.5)μmol/L; MCF7 cells in MEM+ 5% DCC-FBS+ 1 nM 17β-Estradiol, Growth inhibition InRt = (90 ± 13)%, IC50 = (5.4 ± 0.2)μmol/L). Ref: E. Ioannou, et al, BoMC, 2009, 17, 4537

O O

H O H

HO

H

OH

891 5α,8α-epi-Dioxyergosta-6,22-dien-3β-ol Ergosterol peroxide Type: Ergostane steroids. C28H44O3 Cryst. (MeOH), mp 181. 5–183 °C, mp 176–198 °C, [α]D = −29° (c = 0.8, CHCl3). Source: Deep-sea fungus Penicillium commune SD-118, deep-sea fungus Paecilomyces lilacinus ZBY-1, deepsea fungus Penicillium sp. F00120 (northern South China Sea, depth of 1300m), Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters), marine-derived fungus Aspergillus versicolor from brown alga Sargassum thunbergii (Pingtan I., Fujian, China), sponges Axinella cannabina and Thalysias juniperina, crinoid Gymnocrinus richeri, ascidian Ascidia nigra, and occurs widely in fungi and

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

353

lichens. Pharm: Cytotoxic (MTT assay: P388, IC50 = 6.7 μmol/L; HL60, IC50 = 15.3 μmol/L; SRB assay: A549, IC50 = 86.0 μmol/L; Bel7402, IC50 = 61.0 μmol/L); cytotoxic (K562, MCF7, HL60 and BGC823 cells, IC50 = 22.3–139.0 μmol/L); antituberculosis (Mycobacterium tuberculosis). Ref: A. A. C. Gunatilaka, et al, JOC, 1981, 46, 3860│M. Della Greca, et al, Gazz. Chim. Ital., 1990, 120, 391│F. Wang, et al, Steroids, 2008, 73, 19│F. -P. Miao, et al, Mar. Drugs, 2012, 10, 131│Z. Shang, et al, Chin. J. Oceanol. Limnol., 2012, 30, 305│X. Lin, et al, Mar. Drugs, 2012, 10, 106│X. Cui, et al, J. Int. Pharm. Res., 2013, 40, 177 (in Chinese)

H

O

HO

O

892 Diplasterioside B Type: Ergostane steroids. C59H98O27S Source: Starfish Diplasterias brucei (Antarctic, Ross Sea, Terra Nova Bay). Pharm: Cytotoxic (hmn melanoma cell line, mild). Ref: N. V. Ivanchina, et al, Russ. J. Bioorg. Chem., 2011, 37, 499

O OH H H O

HO HO HO HO

OH OO HO

OH S

O

H

O HO OO

H OO

O O

O

O

OH

HO HO

OH

893 Downeyoside A (3β,6α,16β,20R,22S,23S,24R)-16,22-Epoxyergost-9(11)-ene-3,6,20,23-tetrol 3-O-β-Dglucuronopyranoside 6-sulfate Type: Ergostane steroids. C34H54O14S Source: Sea cucumber Henricia downeyae (Gulf of Mexico). Pharm: Cytotoxic (hmn, non-small

354

2 Steroids

cell lung carcinoma cell, IC50 = 60 μg/mL); antifoulant; feeding deterrent. Ref: E. Palagiano, et al, Tetrahedron, 1995, 51, 12293 OH

H

OH 24R

H O OH

O

OO OH OH

O

S O

OH

O OH

894 Downeyoside B (3β,6α,16β,20R,22S,23S,24S)-16,22-Epoxyergost-9(11)-ene-3,6,20,23-tetrol 3-O-β-Dglucuronopyranoside 6-sulfate Type: Ergostane steroids. C34H54O14S Source: Sea cucumber Henricia downeyae (Gulf of Mexico). Pharm: Cytotoxic (hmn, non-small cell lung carcinoma cell, IC50 = 36 μg/mL). Ref: E. Palagiano, et al, Tetrahedron, 1995, 51, 12293 OH

H

OH 24S

H O OH

O

OO OH OH

O

S O

OH

O OH

895 Dysideasterol H Type: Ergostane steroids. C30H48O6 Source: Sponge Dysidea sp.(Ishigaki I., Okinawa). Pharm: Cytotoxic (inhibits hmn epidermoid carcinoma cells). Ref: S. V. S. Govindam, et al, Biosci., Biotechnol., Biochem., 2012, 76, 999

H

O

OH HO

OH

H

O O

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

355

896 5α,8α-Epidioxy-23,24(R)-dimethylcholesta-6,22-dien-3β-ol Type: Ergostane steroids. C29H46O3 Amorph. powder, [α]D16 = −37° (c = 0.05, CHCl3). Source: Marine-derived fungus Penicillium stoloniferum QY2-10 from an unidentified Chinese sea squid, marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters), terrestrial mushroom (shii-take Lentinus edodes). Pharm: Cytotoxic (MTT assay: P388, IC50 = 5.9 μmol/L; HL60, IC50 = 8.7 μmol/L; SRB assay: A549, IC50 > 100 μmol/L; Bel7402, IC50 > 100 μmol/L); cytotoxic (P388, IC50 = 4.07 μmol/L). Ref: Y. Yasunori, et al, CPB, 1998, 46, 944│Z. -H. Xin, et al, Arch. Pharmacal Res., 2007, 30, 816│F. Wang, et al, Steroids, 2008, 73, 19

H

O

O

H

HO

897 5,8-Epidioxy-23-methylergosta-6,9(11),22-trien-3-ol Type: Ergostane steroids. C29H44O3 Amorph. powder. Source: Marine-derived fungi Aspergillus niger, Rhizopus sp. from bryozoan Bugula sp. (China waters) and Rhizopus sp. Pharm: Cytotoxic (MTT assay: P388, IC50 = 7.9 μmol/L; HL60, IC50 = 2.7 μmol/L; SRB assay: A549, IC50 > 100 μmol/L; Bel7402, IC50 = 66.7 μmol/L). Ref: Y. Yaoita, et al, CPB, 1998, 46, 944│F. Wang, et al, Steroids, 2008, 73, 19

H

O

O

H

HO

898 7,8-Epoxyergost-22-ene-3,5,6-triol 7,8-Epoxy-24-methylcholest-22-ene-3,5,6-triol Type: Ergostane steroids. C28H46O4 Cryst., mp 187–188 °C. Source: Gorgonian Acabaria undulata (Korea waters). Pharm: Cytotoxic (P388, IC50 = 20.2 μg/mL; DLD-1, IC50 = 22.4 μg/mL). Ref: J. Shin, et al, JNP, 1996, 59, 679

356

2 Steroids

H

O HO

OH OH

899 (22E,24R)-5α,6α-Epoxy-3β-hydroxyergosta-22-ene-7-one Type: Ergostane steroids. C28H44O3 Source: Deep-sea fungus Paecilomyces lilacinus ZBY-1. Pharm: Cytotoxic (K562, MCF7, HL60 and BGC823 cells, IC50 = 22.3–139.0 μmol/L). Ref: X. Cui, et al, J. Int. Pharm. Res., 2013, 40, 177 (in Chinese)

H

HO

O

O

900 (3β,23S)-Ergosta-5,24(28)-diene-3,23-diol Type: Ergostane steroids. C28H46O2 Source: Soft coral Nephthea erecta (Taiwan waters). Pharm: Anti-inflammatory (LPS-stimulated RAW 264.7 cells, 10 μmol/L: inhibits up-regulation of pro-inflammatory iNOS to 45.8% and COX-2 to 68.1% compare with control LPS-stimulated cells alone; control CAPE inhibits iNOS to 1.5% and COX-2 to 70.2%; cell survival is not changed). Ref: S. Y. Cheng, et al, Chem. Biodivers. 2009, 6, 86

S

H

OH

H H

H

HO

901 (3β,23R)-Ergosta-5,24(28)-diene-3,23-diol Type: Ergostane steroids. C28H46O2 Source: Soft coral Nephthea erecta (Taiwan waters). Pharm: Anti-inflammatory (LPS-stimulated RAW 264.7 cells, 10 μmol/L: inhibits up-regulation of pro-inflammatory iNOS to 62.8%, doesn’t inhibit COX-2 protein expression compare with control LPS-stimulated cells alone;control CAPE

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

357

inhibits iNOS to 1.5% and COX-2 to 70.2%; cell survival is not changed). Ref: S. Y. Cheng, et al, Chem. Biodivers. 2009, 6, 86

R

H

OH

H H

H

HO

902 (3β,25)-Ergosta-5,24(28)-diene-3,25-diol Type: Ergostane steroids. C28H46O2 Source: Soft coral Nephthea erecta (Taiwan waters). Pharm: Anti-inflammatory (LPS-stimulatedRAW 264.7 cells, 10 μmol/L: inhibits up-regulation of pro-inflammatory iNOS to 15.6%, doesn’t inhibit COX-2 protein expression compare with control LPS-stimulated cells alone;control CAPE inhibits iNOS to 1.5% and COX-2 to 70.2%; cell survival is not changed). Ref: S. Y. Cheng, et al, Chem. Biodivers. 2009, 6, 86

H

OH

H H

H

HO

903 Ergosta-4,24(28)-diene-3β,6β-diol Type: Ergostane steroids. C28H46O2 Needles (Me2CO), mp 236–237 °C, [α]D = +20.5° (c = 0.15, MeOH). Source: Soft corals Alcyonium patagonicum (South China Sea) and Sinularia ovispiculata (India waters). Pharm: Cytotoxic (P388, IC50 = 1 μg/mL). Ref: V. Anjaneyulu, et al, Ind. J. Chem., Sect. B, 1994, 33, 806│L. Zeng, et al, JNP, 1995, 58, 296│J. G. Cui, et al, Steroids, 2001, 66, 33

24

H H

HO OH

358

2 Steroids

904 (22E)-Ergosta-7,22-diene-6α-hexadecanooxyl-3β,5α-diol Type: Ergostane steroids. C44H76O4 Oily solid, [α]D24 = +46° (c = 0.17, CHCl3). Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China), terrestrial plant (Astraeus hygrometricus). Pharm: Cytotoxic (B16 and SMMC-7721, mild). Ref: H. Gao, et al, Helv. Chim. Acta, 2007, 90, 1165

H

H HO

H

OH O O

905 (22E)-Ergosta-7,22-diene-6β-hexadecanooxyl-3β,5α-diol Type: Ergostane steroids. C44H76O4 Oily solid, [α]D25 = −63.4° (c = 0.19, CHCl3). Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China). Pharm: Cytotoxic (B16 and SMMC-7721, mild). Ref: H. Gao, et al, Helv. Chim. Acta, 2007, 90, 1165

H

H HO

OH

H

O O

906 (22E)-Ergosta-7,22-diene-6α-9Z,12Z-octadecadienooxyl-3β,5α-diol Type: Ergostane steroids. C46H76O4 Oily solid, [α]D25 = +6.6° (c = 0.18, CHCl3). Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China). Pharm: Cytotoxic (B16 and SMMC-7721, mild). Ref: H. Gao, et al, Helv. Chim. Acta, 2007, 90, 1165

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

359

H

H

H

HO OH

O O

907 (22E)-Ergosta-7,22-diene-6β-octadecanooxyl-3β,5α-diol Type: Ergostane steroids. C46H80O4 Oily solid, [α]D25 = −31.1° (c = 0.15, CHCl3). Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China). Pharm: Cytotoxic (B16 and SMMC-7721, mild). Ref: H. Gao, et al, Helv. Chim. Acta, 2007, 90, 1165

H

H

H

HO OH

O O

908 (22E)-Ergosta-7,22-diene-6α-octadecanooxyl-3β,5α-diol Type: Ergostane steroids. C46H80O4 Oily solid, [α]D26 = +23.7° (c = 0.17, CHCl3). Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China). Pharm: Cytotoxic (B16 and SMMC-7721, mild). Ref: H. Gao, et al, Helv. Chim. Acta, 2007, 90, 1165

H

H HO

OH

H

O O

360

2 Steroids

909 (22E)-Ergosta-7,22-diene-6α-9Z-octadecenooxyl-3β,5α-diol Type: Ergostane steroids. C46H78O4 Oily solid, [α]D26 = +31.4° (c = 0.23, CHCl3). Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China). Pharm: Cytotoxic (B16 and SMMC-7721, mild). Ref: H. Gao, et al, Helv. Chim. Acta, 2007, 90, 1165

H

H HO

H

OH O O

910 Ergosta-8(14),22-diene-3β,5α,6β,7α-tetraol Type: Ergostane steroids. C28H46O4 Cryst., mp 178–180 °C, [α]D25 = −65° (c = 0.2, CHCl3). Source: Marine-derived fungus Penicillium sp. from unidentified moss (South Pole), terrestrial mushroom (Grifola frondosa). Pharm: Cytotoxic (HepG, IC50 = 10.4 μg/mL). Ref: T. Ishizuka, et al, CPB, 1997, 45, 1756│Y. Sun, et al, Nat. Prod. Res., 2006, 20, 381

H

H HO

OH OH

OH

911 (3β,6α,15β,22E,24R,25S)-Ergosta-8(14),22-diene-3,6,15,26-tetrol Type: Ergostane steroids. C28H46O4 [α]D = −2.5° (c = 1, MeOH). Source: Starfish Acodontaster conspicuus (Antarctic). Pharm: Antibacterial (Antarctic marine bacteria McM13.3 and McM32.2, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, JNP, 1997, 60, 959 25S

H

OH HO OH

24R

OH

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

361

912 (3β,22S)-Ergosta-5,24(28)-diene-3,17,22-triol Type: Ergostane steroids. C27H46O3 Source: Soft coral Nephthea erecta (Taiwan waters). Pharm: Anti-inflammatory (LPS-stimulated RAW 264.7 cells, 10 μmol/L: inhibits up-regulation of pro-inflammatory iNOS to 33.6% and COX-2 to 10.3% compare with control LPS-stimulated cells alone;control CAPE inhibits iNOS to 1.5% and COX-2 to 70.2%; cell survival is not changed); cytotoxic (P388, ED50 = 3.7, control Mithramycin, ED50 = 0.06 μg/mL). Ref: S. Y. Cheng, et al, Chem. Biodivers. 2009, 6, 86 OH

OH H H

H

HO

913 24S-Ergostane-3β,5α,6β,7β-tetrol Type: Ergostane steroids. C28H50O4 Needles, mp 212–215 °C, [α]D = +16° (c = 0.5, Py). Source: Soft coral Anthelia glauca. Pharm: 5α-Reductase inhibitor. Ref: U. Sjöstrand, et al, Steroids, 1981, 38, 347│B. N. Ravi, et al, Aust. J. Chem., 1982, 35, 105

H H

HO

OH

OH OH

914 (3β,5α,6β,24ξ)-Ergostane-3,5,6,25-tetrol 25-acetate Type: Ergostane steroids. C30H52O5 Cryst., mp 226 °C, [α]D = −17° (c = 0.25, EtOH). Source: Soft corals Lobophytum sp. (Vietnam), Lobophytum mirabile and Sclerophytum sp. Pharm: Cytotoxic (A549, IC50 = 36.9 μmol/L, control Mitoxantrone, IC50 = 6.1 μmol/L; HT29, IC50 = 3.7 μmol/L, Mitoxantrone, IC50 = 6.5 μmol/L). Ref: C. B. Rao, et al, Ind. J. Chem., Sect. B, 1990, 29, 588│H. T. Nguyen, et al, Arch. Pharm. Res., 2010, 33, 503

362

2 Steroids

O H

O

H H HO

OH

OH

915 (22E,24R)-Ergosta-4,6,8(14),22-tetraen-3-one Type: Ergostane steroids. C28H40O Yellow plates (MeOH), mp 114–115 °C, [α]D24 = +610° (c = 1.1, CHCl3). Source: Sponge Dysidea herbacea. Pharm: Phytotoxin. Ref: M. Kobayashi, et al, CPB, 1992, 40, 72

H

O

916 (24S)-Ergost-5-ene-3β,7α-diol Type: Ergostane steroids. C28H48O2 White powder, mp 210–212 °C, [α]D25 = −75.2° (c = 0.45, CHCl3). Source: Soft corals Lobophytum laevigatum (Khanh Hoa province, Vietnam) and Sclerophytum sp. Pharm: Upregulats PPARs transcription (HepG2, dose-dependent). Ref: M. Kobayashi, et al, CPB, 1993, 41, 87│T. H. Quang, et al, BoMCL, 2011, 21, 2845

H H

HO

OH

917 (3β,5α,24R)-Ergost-7-en-3-ol methoxymethyl ether Type: Ergostane steroids. C30H52O2 Gum, [α]D24 = +240° (c = 0.03, CH2Cl2). Source: Sponge Scleritoderma cf. paccardi (Caribbean Sea). Pharm: Cytotoxic (P388, IC50 = 2.3 μg/mL). Ref: S. P. Gunasekera, et al, JNP, 1996, 59, 161

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

H

363

24R

O O

H

918 Fungisterol γ-Ergostenol; (3β,5α,24S)-Ergost-7-en-3-ol Type: Ergostane steroids. C28H48O Cryst. (EtOH), mp 152 °C, [α]D20 = −0.2° (CHCl3). Source: Green alga Chlorella ellipsoidea, sponge Axinella cannabina, some other sponges, some fungi. Pharm: Immunopotentiator; anticomplementary agent; immunohaemolysis inhibitor. Ref: G. W. Patterson, et al, Phytochemistry, 1974, 13, 191

H

24S

HO H

919 Gibberoepoxysterol Type: Ergostane steroids. C28H46O3 Powder, mp 156–157 °C, [α]D25 = −25° (c = 1.9, CHCl3). Source: Soft coral Sinularia gibberosa (Taiwan waters). Pharm: Cytotoxic (MTT assay, MDA-MB-231, IC50 = 15.9 μg/mL; A549, IC50 = 15.5 μg/mL). Ref: A. F. Ahmed, et al, JNP, 2006, 69, 1275

H OH H H HO

H

O

920 Gibberoketosterol Type: Ergostane steroids. C28H46O4 Cryst. (EtOAc), mp 140–141 °C, [α]D25 = −0.7° (c = 0.38, CHCl3). Source: Soft coral Sinularia gibberosa (Taiwan waters). Pharm: Cytotoxic (MTT assay, HepG2, IC50 = 13.0 μg/mL; MCF7, IC50 = 14.1 μg/mL; MDA-MB -231, IC50 = 14.4 μg/mL; A549, IC50 = 14.5 μg/mL); antiinflammatory (LPS-stimulated

364

2 Steroids

RAW 264.7 cells, 10 μmol/L, inhibits up-regulation of pro-inflammatory iNOS to 44.5% and COX-2 to 68.3% compare with control LPS-stimulated cells alone; 100 μmol/L, inhibits up-regulation of pro-inflammatory protein β-actin to 74%). Ref: A. F. Ahmed, et al, Steroids, 2003, 68, 377│A. F. Ahmed, et al, JNP, 2006, 69, 1275

H OH H H

H

HO OH O

921 Gymnasterone A Type: Ergostane steroids. C45H67NO5 Pale yellow oil, [α]D = −110.7° (c = 1.44, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica. Pharm: Cytotoxic (P388, ED50 = 10.1 μg/mL). Ref: T. Amagata, et al, Tet. Lett., 1998, 39, 3773│T. Amagata, et al, JNP, 2007, 70, 1731

H H OH HO O

NH

O

O

922 Gymnasterone B Type: Ergostane steroids. C28H40O3 Powder, mp 197–199 °C, [α]D = −76.3° (c = 0.76, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica (Japan, malt-glucose-yeast media). Pharm: Cytotoxic (P388, ED50 = 1.6 μg/mL). Ref: T. Amagata, et al, Tet. Lett., 1998, 39, 3773│T. Amagata, et al, JNP, 2007, 70, 1731

H

H O

H

O

O

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

365

923 Gymnasterone C Type: Ergostane steroids. C28H40O2 Yellow cryst. (MeOH), mp 197–199 °C, [α]D22 = +224° (c = 0.25, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica (Japan, malt-glucose-yeast media). Pharm: Cytotoxic (P388, inhibits growth significantly). Ref: T. Amagata, et al, JNP, 2007, 70, 1731

H

O HO

924 Gymnasterone D Type: Ergostane steroids. C28H38O2 Cryst. (MeOH), mp 166–168 °C, [α]D22 = +473.7° (c = 0.88, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica (Japan, malt-glucose-yeast media). Pharm: Cytotoxic (P388, inhibits growth significantly). Ref: T. Amagata, et al, JNP, 2007, 70, 1731

H

O O

925 Halicrasterol A Type: Ergostane steroids. C29H50O4 Source: Sponge Haliclona crassiloba (Dongshan I., Guangdong, China). Pharm: Antimicrobial (various microbial pathogens, moderate). Ref: Z. -B. Cheng, et al, Steroids, 2013, 78, 1353

HO H H HO

OH

OH

H

366

2 Steroids

926 Halicrasterol B Type: Ergostane steroids. C31H52O6 Source: Sponge Haliclona crassiloba (Dongshan I., Guangdong, China). Pharm: Antimicrobial (various microbial pathogens, moderate). Ref: Z. -B. Cheng, et al, Steroids, 2013, 78, 1353

O O H H HO

OH

OH H

OH

927 Halicrasterol C Type: Ergostane steroids. C28H48O4 Source: Sponge Haliclona crassiloba (Dongshan I., Guangdong, China). Pharm: Antimicrobial (various microbial pathogens, moderate). Ref: Z. -B. Cheng, et al, Steroids, 2013, 78, 1353

H

HO H H HO

H

OH OH

928 Halicrasterol D Type: Ergostane steroids. C30H50O5 Source: Sponge Haliclona crassiloba (Dongshan I., Guangdong, China). Pharm: Antimicrobial (various microbial pathogens, moderate). Ref: Z. -B. Cheng, et al, Steroids, 2013, 78, 1353

O H

O H H HO

OH

H

OH

929 Halistanol sulfate 25-Methylergostane-2,3,6-triol tri-O-sulfate Type: Ergostane steroids. C29H52O12S3 Cryst. (tri-Na salt), mp 159.5–160.5 °C (tri-Na salt), [α]D = +17°. Source: Sponges Aka

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

367

sp., Epipolasis kushimotoensis, Epipolasis sp. (Japan waters), Halichondria moorei, Halichondria cf. moorei, Trachyopsis sp., Haliclona sp. and Topsentia sp. Pharm: Thrombin inhibitor (IC50 = 17 μg/mL); CDK/cyclin D1 inhibitor (IC50 = 9.5 μg/mL); haemolytic; ichthyotoxic; adenosine receptor agonist; starfish fertilisation inhibitor; antimicrobial. Ref: N. Fusetani, et al, Tet. Lett., 1981, 22, 1985│S. Kanazawa, et al, Tetrahedron, 1992, 48, 5467│S. Sperry, et al, JNP, 1997, 60, 29│V. Mukku,et al, JNP 2003, 66, 686│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev)

O O

O O

S

H

OH H

O

O S

H OH

O S

O OH

O

930 Halistanol sulfate A Type: Ergostane steroids. C28H48O12S3 [α]D21 = +16.4° (c = 1, MeOH). Source: Sponge Epipolasis sp. (Japan waters). Pharm: Thrombin inhibitor (IC50 = 17 μg/mL). Ref: S. Kanazawa, et al, Tetrahedron, 1992, 48, 5467

O O

O O

S

H

OH H

O

O S

H OH

O S

O OH

O

931 Halistanol sulfate E Type: Ergostane steroids. C29H52O13S3 [α]D21 = +13.3° (c = 0.21, MeOH) (tri-Na salt). Source: Sponge Epipolasis sp. (Japan waters). Pharm: Thrombin inhibitor (IC50 = 90 μg/mL). Ref: S. Kanazawa, et al, Tetrahedron, 1992, 48, 5467

368

O

H

OH

S

O

2 Steroids

H

O

OH O

O

H

S

O

OH

O

O S

OH

O

932 Halistanol sulfate F Type: Ergostane steroids. C30H54O12S3 Source: Sponge Pseudoaxinissa digitata. Pharm: Anti-HIV (HIV inhibitor in vitro). Ref: G. Bifulco, et al, JNP, 1994, 57, 164

HO

S

O O HO

H

O

S

H

O

O

H

O

O

O S O OH

933 Halistanol sulfate G Type: Ergostane steroids. C28H50O12S3 Source: Sponge Pseudoaxinissa digitata. Pharm: Anti-HIV (HIV inhibitor in vitro). Ref: G. Bifulco, et al, JNP, 1994, 57, 164

HO

S

O O HO

H

O

S

H

O

O

H

O O

O S

O

OH

934 Halistanol sulfate H Type: Ergostane steroids. C28H48O12S3 Source: Sponge Pseudoaxinissa digitata. Pharm: Anti-HIV (in vitro). Ref: G. Bifulco, et al, JNP, 1994, 57, 164

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

HO

S

O HO

H

O

O

S

369

H

O

O

H

O O

O S

O

OH

935 Haplosamate A Type: Ergostane steroids. C29H51O12PS Solid (Na salt), mp 210 °C (dec) (Na salt), [α]D = −32° (c = 0.4, MeOH) (Na salt), [α]D24 = −6.9° (c = 2.5, MeOH) (Na salt). Source: Sponge Cribrochalina sp. (Japan waters), two unidentified sponges (order Haplosclerida, Phillipines). Pharm: Membrane-type matrix metallo-proteinase inhibitor. Ref: A. Qureshi, et al, Tetrahedron, 1999, 55, 8323│M. Fujita, et al, Tetrahedron, 2001, 57, 3885

H O

H HO O

O

O S

H O OH

H

H

O

OH

P

O

OH

OH

936 Haplosamate B Type: Ergostane steroids. C29H52O15P2S Solid (di-Na salt), mp 213 °C (dec) (di-Na salt), [α]D = −8° (c = 0.1, MeOH) (di-Na salt), Source: Sponge Cribrochalina sp. (Japan waters). Pharm: Membrane-type matrix metallo-proteinase inhibitor. Ref: A. Qureshi, et al, Tetrahedron, 1999, 55, 8323│M. Fujita, et al, Tetrahedron, 2001, 57, 3885

H O

H HO O

O

O S

H O OH

H

H

O

O OH

O

P OH

P OH

OH

O

370

2 Steroids

937 Hippasterioside A (20R,22R,23S,24S)-22,23-Epoxy-20-hydroxy-24-methyl-6α-O-{β-D-xylopyranosyl-(1→3)β-D-fucopyranosyl-(1→2)-β-D-quinovopyranosyl-(1→4)-[β-D-quinovopyranosyl-(1→2)]β-D-xylopyranosyl-(1→3)-β-D-quinovopyranosyl}-5α-cholest-9(11)-en-3β-yl sulfate Type: Ergostane steroids. C62H102O31S Colorless amorph. powder, [α]D25 = +1.3° (c = 0.2, H2O/ MeOH 1:3). Source: Starfish Hippasteria kurilensis (Kuril Is., Sea of Okhotsk). Pharm: Cytotoxic (HT29, inhibiting colony formation, reduced colony number by 17%). Ref: A. A. Kicha, et al, Chem. Biodiversity, 2011, 8, 166 O

OH H H H

O HO

S

O

OO

HO HO

O O HO

HO

O

HO OO HO O

O O

HO

O

H

O

O OH

HO HO

HO

OH

938 Hippuristerol A Type: Ergostane steroids. C33H54O7 Powder, [α]D25 = +6.1° (c = 0.4, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 = 1 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 O O O O OH

H H

O

H

HO H

939 Hippuristerol B Type: Ergostane steroids. C33H54O6 Powder, [α]D24 = +2.3° (c = 0.225, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 = 1.25 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

371

O O

O

O

O

H H

H

HO H

940 Hippuristerol D Type: Ergostane steroids. C32H54O6 Powder, [α]D27 = +3.7° (c = 0.175, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 > 10 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 O

OH

O

O O

H H H HO

H

H

941 Hippuristerone A Type: Ergostane steroids. C33H52O7 Cryst., mp 153–154 °C, [α]D25 = +17° (c = 0.5, CHCl3). Source: Gorgonian Isis hippuris (Indonesia, Taiwan). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 > 10 μg/mL). Ref: J. -H. Sheu, et al, Tet. Lett., 2000, 41, 7885│N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 O O O O H H O H

O OH

H

372

2 Steroids

942 Hippuristerone B Type: Ergostane steroids. C33H52O6 Powder, [α]D28 = +8.7° (c = 0.765, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 > 10 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 O O O O

O

H H

H O H

943 Hippuristerone D Type: Ergostane steroids. C32H52O6 Powder, [α]D23 = +7.38° (c = 0.38, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, A549, HT29, MEL28, all IC50 > 10 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 O

OH

O

H

O O

H H O

H

H

944 Hirsutosterol E Type: Ergostane steroids. C30H50O5 White power, [α]D25 = −22° (c = 1.02, CHCl3). Source: Soft coral Cladiella hirsuta (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 > 50 μmol/L, control Doxorubicin, IC50 = 0.4 μmol/L; HepG3B, IC50 > 50 μmol/L, Doxorubicin, IC50 = 1.3 μmol/L; Ca9-22, IC50 > 50 μmol/L, Doxorubicin, IC50 = 0.2 μmol/L; A549, IC50 = 18.4 μmol/L, Doxorubicin, IC50 = 2.6 μmol/L; MCF7, IC50 > 50 μmol/L, Doxorubicin, IC50 = 2.9 μmol/L; MDA-MB-231, IC50 > 50 μmol/L, Doxorubicin, IC50 = 2.0 μmol/L). Ref: B. -W. Chen, et al, Org. Biomol. Chem., 2011, 9, 3272

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

H

HO

O OH O

H

373

H

OH

945 Hirsutosterol F Type: Ergostane steroids. C30H48O5 White power, [α]D25 = −13° (c = 0.42, CHCl3). Source: Soft coral Cladiella hirsuta (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 = 32.0 μmol/L, control Doxorubicin, IC50 = 0.4 μmol/L; HepG3B, IC50 = 15.2 μmol/L, Doxorubicin, IC50 = 1.3 μmol/L; Ca9-22, IC50 = 17.6 μmol/L, Doxorubicin, IC50 = 0.2 μmol/L; A549, IC50 > 50 μmol/L, Doxorubicin, IC50 = 2.6 μmol/L; MCF7, IC50 = 34.6 μmol/L, Doxorubicin, IC50 = 2.9 μmol/L; MDA-MB-231, IC50 = 26.8 μmol/L, Doxorubicin, IC50 = 2.0 μmol/L). Ref: B. -W. Chen, et al, Org. Biomol. Chem., 2011, 9, 3272

H

HO

O

OH O

H

H OH

946 7β-Hydroperoxy-24-methylenecholersterol Type: Ergostane steroids. C28H46O3 mp 115–117 °C, [α]D26 = +45° (c = 0.1, CHCl3). Source: Soft coral Sinularia sp. (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 2.6 μg/mL; KB, ED50 > 50 μg/mL; A549, ED50 > 50 μg/mL; HT29, ED50 > 50 μg/mL). Ref: J. -H. Sheu, et al, J. Chin. Chem. Soc., 1999, 46, 253

H H

HO

O

OH

374

2 Steroids

947 (22E)-3β-Hydroxy-5α,6α:14α,15α-diepoxyergosta-22-en-7-one Type: Ergostane steroids. C28H42O4 Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China). Pharm: Cytotoxic (A549, weak). Ref: H. Gao, et al, Magn. Reson. Chem., 2010, 48, 38

H

H

O O

HO O

948 3β-Hydroxy-( 22E,24R)-ergosta-5,8,14,22-tetraen-7-one Type: Ergostane steroids. C28H40O2 Amorph. powder, [α]D22 = +50° (c = 0.1, CHCl3). Source: Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters). Pharm: Cytotoxic (MTT assay: P388, IC50 = 2.0 μmol/L; HL60, IC50 = 7.1 μmol/L; SRB assay: A549, IC50 > 100 μmol/L; Bel7402, IC50 = 85.5 μmol/L). Ref: F. Wang, et al, Steroids, 2008, 73, 19

H

HO

O

949 15α-Hydroxy-(22E,24R)-ergosta-3,5,8(14),22-tetraen-7-one Type: Ergostane steroids. C28H40O2 Colourless needles, [α]D20 = −16.5° (c = 1.0, CHCl3). Source: Mangrove-derived fungus Aspergillus aculeatus HTTM-Z07002 from mangrove Acanthus ebracteatus (South China Sea, 2007, identified by prof. Tian Li of the Frist Inst. of Oceanography SOA and Qingdao Univ. of Sci. and Tech., China). Pharm: Cytotoxic (MTT assay, PC3, IC50 = 0.7 μmol/L; trypan blue assay, P388, IC50 = 0.02 μmol/L, HL60, IC50 = 0.04 μmol/L). Ref: Y, Wang, et al, Yaoxue Xuebao, 2014, 49(1), 68

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

375

H

H

OH O

950 3β-Hydroxy-(22E,24R)-ergosta-5,8,22-trien-7,15-dione Type: Ergostane steroids. C28H40O3 Pale yellow oil, [α]D22 = +17° (c = 0.1, CHCl3). Source: Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters). Pharm: Cytotoxic (MTT assay: P388, IC50 = 9.3 μmol/L; HL60, IC50 = 3.1 μmol/L; SRB assay: A549, IC50 = 17.6 μmol/L; Bel7402, IC50 = 5.9 μmol/L). Ref: F. Wang, et al, Steroids, 2008, 73, 19

H

H HO

O

O

951 3β-Hydroxyl-(22E,24R)-ergosta-5,8(14),22-trien-7,15-dione Type: Ergostane steroids. C28H40O3 Amorph. powder, [α]D22 = −21° (c = 0.035, CHCl3). Source: Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters). Pharm: Cytotoxic (MTT assay: P388, IC50 = 4.8 μmol/L; SRB assay: A549, IC50 = 6.6 μmol/L). Ref: F. Wang, et al, Steroids, 2008, 73, 19

H

H HO

O O

952 3β-Hydroxyl-(22E,24R)-ergosta-5,8,22-trien-7-one Type: Ergostane steroids. C28H42O2 Amorph. powder, [α]D24 = −28.3° (c = 0.1, CHCl3). Source: Marine-derived fungus Rhizopus sp. from bryozoan Bugula sp. (China waters), terrestrial mushroom (Grifola frondosa, fruit body). Pharm: Cytotoxic (MTT assay: P388, IC50 = 3.0 μmol/L; HL60, IC50 = 4.2 μmol/L; SRB assay: A549,

376

2 Steroids

IC50 = 23.8 μmol/L; Bel7402, IC50 = 34.2 μmol/L). Ref: D. C. Burk, et al, J Chem Soc, 1953, 3237│T. Ishizuka, et al, CPB, 1997, 45, 1756│F. Wang, et al, Steroids, 2008, 73, 19

H

H HO

O

953 Hymenosulfate Hymenosulphate Type: Ergostane steroids. C29H48O4S Cryst. (MeOH) (Na salt), mp 247–250 °C (Na salt), [α]D22 = −23° (c = 0.1, MeOH) (Na salt). Source: Diatom Hymenomonas sp. Pharm: Calcium release agent. Ref: J. Kobayashi, et al, JCS Perkin I, 1989, 101

H H O HO O

S

O

954 Ibisterol C Type: Ergostane steroids. C30H50O12S3 Source: Sponge Xestospongia sp. (Philippines). Pharm: HIV-1 integrase Inhibitor. Ref: M. L. Lerch, et al, Tetrahedron, 2001, 7, 4091

O

HO O

O S

OH S

H

O

O

O O

S O

O OH

955 Ibisterol sulfate B Type: Ergostane steroids. C29H48O12S3 Powder, [α]D = +50° (c = 0.28, MeOH). Source: Sponge Xestospongia sp. (Philippines). Pharm: HIV-1 integrase Inhibitor. Ref: M. L. Lerch, et al, Tetrahedron, 2001, 7, 4091

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

OH O

377

H

O

S O O HO O

S O O

O S

OH O

956 Isocyathisterol Type: Ergostane steroids. C28H42O2 Source: Marine-derived fungus Aspergillus ustus cf-42 (algicolous). Pharm: Antibacterial (30 μg/disk: E. coli, IZ = 6.7 mm; Staphylococcus aureus, IZ = 5.7 mm). Ref: X. H. Liu, et al, Nat. Prod. Res., 2014, 28, 1182

H H H

OH

O

957 Linckoside M Type: Ergostane steroids. C39H64O14 Amorph. solid, [α]D16 = −35° (c = 0.22, MeOH). Source: Starfish Linckia laevigata (Okinawa). Pharm: Nervous system activity (neurite outgrowth inducer, IC50 (apparent) > 10 μmol/L, MMOA: dependent on xylose on side chain). Ref: C. Han, et al, J. Nat. Med. (Tokyo), 2007, 61, 138

25S 24R

H OH

OH OH

OO OH OH

OO OH OH

OH

OH O

958 Linckoside Q Type: Ergostane steroids. C33H56O10 Amorph. solid, [α]D = −16° (c = 0.25, MeOH). Source: Starfish Linckia laevigata (Okinawa). Pharm: Nervous system activity

378

2 Steroids

(neurite outgrowth inducer, IC50 (apparent) > 10 μmol/L, MMOA: dependent on xylose on side chain). Ref: C. Han, et al, J. Nat. Med. (Tokyo), 2007, 61, 138

25S 24R

OH

H OH

OH OH

OO OH OH

OH OH

959 Litosterol 3β-Ergosta-5,24(28)-diene-3,19-diol Type: Ergostane steroids. C28H46O2 Cryst., mp 147.5–150 °C, [α]D = −25.8° (c = 0.24, MeOH). Source: Soft corals Litophyton viridis and Nephthea erecta. Pharm: Cytotoxic (A549, ED50 = 1.76 μg/mL; HT29, ED50 = 1.31 μg/mL; KB, ED50 = 1.10 μg/mL; P388, ED50 = 0.45 μg/mL); antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 90%, MIC = 3.13 μg/mL). Ref: K. Iguchi, et al, CPB, 1989, 37, 2553│C. -Y. Duh, et al, JNP, 1998, 61, 1022│A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949

H HO H

HO

960 (22E)-7α-Methoxy-5α,6α-epoxyergosta-8(14),22-dien-3β-ol Type: Ergostane steroids. C29H46O3 Source: Mangrove-derived fungus Aspergillus awamori from soil around mangrove Acrostichum speciosum (Hainan, China). Pharm: Cytotoxic (A549, weak). Ref: H. Gao, et al, Magn. Reson. Chem., 2010, 48, 38

H

H HO

O

O

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

379

961 24-Methylcholesta-5,24(28)-diene-3β,15β,19-triol Type: Ergostane steroids. C28H46O3 Prisms, mp 204–205 °C, [α]D25 = −28.8° (c = 0.34, MeOH). Source: Soft coral Nephthea erecta. Pharm: Cytotoxic (A549, ED50 = 0.41 μg/mL; HT29, ED50 = 0.17 μg/mL; KB, ED50 = 0.60 μg/mL; P388, ED50 = 0.07 μg/mL). Ref: C. -Y. Duh, et al, JNP, 1998, 61, 1022

H HO H OH HO

962 24-Methylcholesta-5,24(28)-diene-3β,19-triol-7-one Type: Ergostane steroids. C28H44O3 Prisms, mp 165–167 °C, [α]D25 = −19.1° (c = 0.13, MeOH). Source: Soft coral Nephthea erecta. Pharm: Cytotoxic (A549, ED50 = 4.09 μg/mL; HT29, ED50 = 3.34 μg/mL; KB, ED50 > 50 μg/mL; P388, ED50 = 0.4 μg/mL). Ref: C. -Y. Duh, et al, Taiwan Shuichan Xuehuikan, 1997, 24, 127│C. -Y. Duh, et al, JNP, 1998, 61, 1022 22

H HO

H

HO

O

963 (24R)-24-Methyl-5α-cholestane-3β,5,6β,15α,24,28-hexaol 28-sulfate Type: Ergostane steroids. C28H50O9S [α]D = +17.0°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653 O HO

S

O

O

OH 24R

H H OH HO

OH

OH

380

2 Steroids

964 (24R,25S)-24-Methyl-5α-cholestane-3β,5,6β,15α,16β,26-hexaol 26-sulfate Type: Ergostane steroids. C28H50O9S [α]D = +22.6°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653

25S

O

24R

H H

O OH

S O OH

OH HO

OH OH

965 (24S)-24-Methylcholest-5-ene-3β,25-diol Type: Ergostane steroids. C28H48O2 White powder, mp 184–188 °C, [α]D25 = −51.3° (c = 1.00, CHCl3). Source: Soft corals Lobophytum laevigatum (Khanh Hoa province, Vietnam), Sarcophyton glaucum and Nephthea sp. Pharm: Cytotoxic (A549, IC50 > 20 μmol/L, control Mitoxantrone, IC50 = (7.8 ± 0.4)μmol/L; HCT116, IC50 = (18.1 ± 1.2)μmol/L, Mitoxantrone, IC50 = (7.2 ± 0.3)μmol/L; HL60, IC50 > 20 μmol/L, Mitoxantrone, IC50 = (8.2 ± 0.9)μmol/L; induction of apoptosis). Ref: J. P. Engelbrecht, et al, Steroids, 1972, 20, 121│M. Kobayashi, et al, CPB, 1983, 31, 1848│T. H. Quang, et al, BoMCL, 2011, 21, 2845

H

OH

H

HO

966 (22E,24R,25S)-24-Methyl-5α-cholest-22-ene-3β,5,6β,15α,26-pentol-26sulfate Type: Ergostane steroids. C28H48O8S [α]D = +24.3°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

381

25S

O

24R

H O

H

S OH

O

OH HO

OH OH

967 (22E,24S)-24-Methyl-5α-cholest-22-ene-3β,5,6β,15α,28-pentol 28-sulfate Type: Ergostane steroids. C28H48O8S [α]D = +5.4°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653 O O

S

OH O

24S

H H OH HO

OH

OH

968 24-Methylenecholesterol-5-ene-3β,16β-diol-3-O-α-L-fucopyranoside Type: Ergostane steroids. C34H56O6 Needles (CHCl3/MeOH), mp 248–251 °C, [α]D27 = −122° (c = 1, Py). Source: Soft corals Sinularia hirta and Sinularia conferta. Pharm: 5α-Reductase inhibitor. Ref: C. Subrahmanyam, et al, Ind. J. Chem., Sect. B, 1993, 32, 1093│V. Anjaneyulu, et al, Ind. J. Chem., Sect. B, 1994, 33, 144

H H

O OH

O

OH OH

OH

382

2 Steroids

969 Nebrosteroid O Type: Ergostane steroids. C30H48O5 White amorph. powder, [α]D25 = −32.2° (c = 0.1, CHCl3). Source: Soft coral Nephthea chabroli (Taitung county, Taiwan). Pharm: Cytotoxic (A549, ED50 = 5.9 μg/mL, control Mithramycin, ED50 = 0.18 μg/mL; HT29, ED50 = 5.9 μg/mL, Mithramycin, ED50 = 0.21 μg/mL; P388, ED50 = 1.2 μg/mL, Mithramycin, ED50 = 0.15 μg/mL; HEL, ED50 = 15.4 μg/mL). Ref: S. -K. Wang, et al, Mar. Drugs, 2012, 10, 1288

O H

HO O H H

H

HO O

970 Nebrosteroid P Type: Ergostane steroids. C29H50O4 White amorph. powder, [α]D25 = −44.0° (c = 0.1, CHCl3). Source: Soft coral Nephthea chabroli (Taitung county, Taiwan). Pharm: Cytotoxic (A549, ED50 = 7.2 μg/mL, control Mithramycin, ED50 = 0.18 μg/mL; HT29, ED50 = 9.5 μg/mL, Mithramycin, ED50 = 0.21 μg/mL; P388, ED50 = 1.7 μg/mL, Mithramycin, ED50 = 0.15 μg/mL; HEL, ED50 = 16.1 μg/mL). Ref: S. -K. Wang, et al, Mar. Drugs, 2012, 10, 1288

H HO H H

H

HO O

OH

971 Nephalsterol A (3β,5α,6β)-Ergost-24(28)-ene-3,5,6,19-tetrol; 24-Methylenecholestane-3,5,6,19-tetrol Type: Ergostane steroids. C28H48O4 Needles, mp 242–243 °C. Source: Soft corals Nephthea albida, Nephthea erecta, Nephthea tiexieral verseveldt and Sinularia sp. Pharm: Cytotoxic (A549, ED50 = 0.81 μg/mL; HT29, ED50 = 0.93 μg/mL; KB, ED50 = 0.39 μg/mL; P388, ED50 = 0.34 μg/mL). Ref: L. Zeng, et al, Gaodeng Xuexiao Huaxue Xuebao, 1991, 12, 910; CA, 117, 87078│L. -B. Ma, et al, Acta Chim. Sinica, 1993, 51, 167│C. -Y. Duh, et al, JNP, 1998, 61, 1022

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

HO

HO

383

H

OH OH

972 Nephalsterol B (3β,7β)-Ergosta-5,24(28)-diene-3,7,19-triol Type: Ergostane steroids. C28H46O3 Flakes (Me2CO), mp 160–162 °C. Source: Soft corals Litophyton arboreum, Litophyton viridis, Nephthea erecta and Nephthea albida. Pharm: Cytotoxic (A549, ED50 = 0.69 μg/mL; HT29, ED50 = 0.72 μg/mL; KB, ED50 = 0.58 μg/mL; P388, ED50 = 0.24 μg/mL); antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 69%). Ref: M. Bortolotto, et al, Steroids, 1976, 28, 461│D. Losman, et al, Acta Cryst. B, 1978, 34, 2586│L. Zeng, et al, Gaodeng Xuexiao Huaxue Xuebao, 1991, 12, 910│ J.-K. Liu, et al, Gaodeng Xuexiao Huaxue Xuebao, 1992, 13, 341│R. Li, et al, Steroids, 1994, 59, 503│C. -Y. Duh, et al, Taiwan Shuichan Xuehuikan, 1997, 24, 127│ C.-Y. Duh, et al, JNP, 1998, 61, 1022│A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 22

H HO

H

HO

OH

973 Nephalsterol C (3β,7β)-Ergosta-5,24(28)-diene-7-acetoxy-3,19-diol Type: Ergostane steroids. C30H48O4 Source: Soft corals Nephthea albida and Nephthea simulata. Pharm: Antituberculosis (Mycobacterium tuberculosis H37Rv, 12.5 μg/mL, InRt = 96%, MIC = 12.5 μg/mL). Ref: J.-K. Liu, et al, Gaodeng Xuexiao Huaxue Xuebao, 1992, 13, 341; 355│A. E. -S. Khalid, et al, Tetrahedron, 2000, 56, 949 22

H HO

H O

HO

O

384

2 Steroids

974 Nigerasterol A Type: Ergostane steroids. C28H42O4 Source: Mangrove-derived fungus Aspergillus niger (endophytic) from mangrove Avicennia marina (Hainan, China). Pharm: Cytotoxic (HTCLs, HL60 and A549, potent). Ref: D. Liu, et al, Helv. Chim. Acta, 2013, 96, 1055

H

O HO

OH

O

975 Nigerasterol B Type: Ergostane steroids. C28H42O4 Source: Mangrove-derived fungus Aspergillus niger (endophytic) from mangrove Avicennia marina (Hainan, China). Pharm: Cytotoxic (HTCLs, HL60 and A549, potent). Ref: D. Liu, et al, Helv. Chim. Acta, 2013, 96, 1055

H

O

OH

HO O

976 Norselic acid C 3-Oxoergosta-1,4,24(28)-trien-18-oic acid Type: Ergostane steroids. C28H40O3 Amorph. solid, [α]D20 = +43° (c = 0.2, CHCl3). Source: Sponge Crella sp. (Norsel Point, Palmer Station, Antarctica). Pharm: Antimicrobial (weak); antifeedant (mesograzers). Ref: W. S. Ma, et al, JNP, 2009, 72, 1842

HOOC

H H O

H

H

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

385

977 Numersterol A (1α,3β,5α,6β)-Ergost-24(28)-ene-1,3,5,6-tetrol Type: Ergostane steroids. C28H48O4 Cryst. (EtOH or MeOH), mp 297–299 °C, mp 268–270 °C, [α]D25 = +4.5° (c = 0.33, MeOH), [α]D22.5 = +15° (c = 0.02, EtOH). Source: Soft corals Sinularia microclavata, Sinularia numerosa and Sinularia sp. Pharm: Cytotoxic (P388, ED50 = 8.3 μg/mL; KB, ED50 = 1.9 μg/mL; A549, ED50 = 10.8 μg/mL; HT29, ED50 = 1.5 μg/mL). Ref: J. Su, et al, JNP, 1989, 52, 934│R. Li, et al, Steroids, 1992, 57, 3│J. H. Sheu, et al, JNP, 2000, 63, 149

H

OH

HO

H

OH OH

978 Orostanal Type: Ergostane steroids. C29H48O3 Amorph. solid, [α]D = +50.6° (c = 0.3, CHCl3). Source: Sponge Stelletta hiwasaensis (Japan waters). Pharm: Cytotoxic (HL60, 10 μg/mL, apoptosis inducer; IG50 = 1.7 μg/mL). Ref: T. Miyamoto, et al, Tet. Lett., 2001, 42, 6349

H H H HO

OH

H O

H

979 Orthohippurinsterol A Type: Ergostane steroids. C32H54O7 [α]D23 = +2.67egree (c = 0.07, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, IC50 = 2.5 μg/mL; A549, IC50 = 5 μg/mL; HT29, IC50 = 5 μg/mL; MEL28, IC50 = 5 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 OH O

O

O O

H H H HO

H

OH H

386

2 Steroids

980 Orthohippurinsterol B Type: Ergostane steroids. C32H54O7 Powder, [α]D27 = +11.7° (c = 0.07, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, IC50 > 10 μg/mL; A549, IC50 = 5 μg/mL; HT29, IC50 = 1 μg/mL; MEL28, IC50 > 10 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 OH O

O

O O

H H H

OH H

HO H

981 Orthohippurinsterone A Type: Ergostane steroids. C32H52O7 Powder, [α]D27 = −58.5° (c = 0.035, CHCl3). Source: Gorgonian Isis hippuris (Indonesia). Pharm: Cytotoxic (P388, IC50 = 2.5 μg/mL; A549, IC50 = 5 μg/mL; HT29, IC50 = 5 μg/mL; MEL28, IC50 = 5 μg/mL). Ref: N. Gonzalez, et al, Tetrahedron, 2001, 57, 3487 OH O

O

O O

H H H O

OH H

H

982 Ostreasterol Chalinasterol Type: Ergostane steroids. C28H46O Cryst., mp 142–143 °C, [α]D20 = −43.6° (CHCl3). Source: Green alga Capsosiphon fulvescens (edible), green algae (Ostreasterol is the major sterol), soft corals Sinularia gibberosa (Taiwan waters), Sinularia sp., crinoid Antedon bifida, urchins Echinus esculentus and Echinocardium cordatum, sea cucumbers Eupentacta fraudatrix, Holothuria nobilis and Synapta maculata, and occurs in many marine organisms. Pharm: Hypoglycemic (aldose reductase inhibitor) (rat lens aldose reductase RLAR inhibitor in vitro assays, IC50 = 345.27 μmol/L, control Quercetin, IC50 = 6.80 μmol/L). Ref: V. A. Stonik, et al, Comp. Biochem. Physiol., B: Biochem. Mol. Biol., 1998, 120, 337│J. -H. Sheu, et al, J. Chin. Chem. Soc. (Taipei), 1999, 46, 253│A. F. Ahmed, et al, JNP, 2006, 69, 1275│M. N. Islam, et al, Eur. J. Nutr., 2014, 53, 233

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

387

H H H

H

HO

983 Pandaroside E 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyloxyuronic acid]-5α,14βergosta-8,16,24(241)-triene-15,23-dione Type: Ergostane steroids. C39H56O14 White amorph. solid, [α]D20 = +30.0° (c = 0.10, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 9.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 71.6 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 15.9 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 13.8 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 40.9 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O OH H

OH

HO

O HO OO

OO

O

H

OH

HO OH

984 Pandaroside E methyl ester Type: Ergostane steroids. C40H58O14 White amorph. solid, [α]D20 = +37.0° (c = 0.10, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 14.3 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 61.9 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 41.3 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 5.9 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 76.9 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

388

2 Steroids

O OH H

O

HO

O HO OO

OO

O

H

OH

HO OH

985 Pandaroside F 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyloxyuronic acid]-5α,14βergost-8,16-diene-15,23-dione Type: Ergostane steroids. C39H58O14 White amorph. solid, [α]D20 = +52.7° (c = 0.16, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 2.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 20.3 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 4.3 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 5.7 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 10.8 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O OH H

OH

HO

O HO OO

OO

O

H

OH

HO OH

986 Pandaroside F methyl ester Type: Ergostane steroids. C40H60O14 White amorph. solid, [α]D20 = +47.3° (c = 0.10, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 54.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 25.1 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 26.8 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 9.9 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 42.1 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

389

O OH H

O

HO

O HO OO

O

H

OO OH

HO OH

987 Parguesterol A Type: Ergostane steroids. C28H44O2 Oil, [α]D25 = −44° (c = 1, CHCl3). Source: Sponge Svenzea zeai (Caribbean Sea). Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC = 7.8 μg/mL). Ref: X. Wei, et al, Tet. Lett., 2007, 48, 8851

H H

HO

O H

988 Parguesterol B Type: Ergostane steroids. C28H46O3 Oil, [α]D25 = +9.2° (c = 1, CHCl3). Source: Sponge Svenzea zeai (Caribbean Sea). Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC = 11.2 μg/mL). Ref: X. Wei, et al, Tet. Lett., 2007, 48, 8851

H H

HO

O

OH H

989 Patusterol A Type: Ergostane steroids. C28H46O3 Source: Soft coral Lobophytum patulum (Shundo, Kenya). Pharm: Toxic (brine shrimp assay, modest). Ref: D. Yeffet, et al, Nat. Prod. Commun., 2010, 5, 205

390

2 Steroids

H OH H H

H

HO

OH

990 PectiniosideB (3β,5α,6α,20R,22R,23S,24S)-22,23-Epoxyergost-9(11)-ene-3,6,20-triol 6-O-[β-D-galactopyranosyl-(1→4)-[β-D-fucopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-[6-deoxyβ-D-glucopyranosyl-(1→2)]-β-D-xylopyranosyl-(1→3)-6-deoxy-β-D-glucopyranoside] 3-O-sulfate Type: Ergostane steroids. C63H104O33S Needles, mp > 300 °C (dec), [α]D = +5.5° (c = 1.28, H2O). Source: Starfish Asterina pectinifera. Pharm: Antihypertensive; sedative; hypnotic. Ref: Y. Noguchi, et al, Annalen, 1987, 341 H O

OH H

H H O HO S

O

O H O

BD-xylop O OH

OH OH

HO

OO OH O

BD-galap O OH

O

OH

OH HO HO

O

O

O

O

O

OH OH

O

BD-fucop OH

OH

991 Penicisteroid A Type: Ergostane steroids. C30H50O6 Source: Marine-derived fungus Penicillium chrysogenum from red alga Laurencia sp. Pharm: Antifungal (20 μg/disk, Aspergillus niger, IZD = 18 mm, control AMPB, IZD = 24 mm, Alternaria brassicae, IZD = 8 mm, control AMPB, IZD = 16 mm); cytotoxic (HeLa, IC50 = 15 μg/mL; SW1990, IC50 = 31 μg/mL; NCI-H460, IC50 = 40 μg/mL). Ref: S. -S. Gao, et al, BoMCL, 2011, 21, 2894

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

H

HO H H HO

391

O

16

O H OH

H OH

992 Polymastiamide A Type: Ergostane steroids. C38H55NO8S Amorph. solid (Na salt), [α]D21 = +67.4° (c = 1.1, MeOH). Source: Sponge Polymastia boletiformis (psychrophilic, cold water, Norway). Pharm: Antibacterial (in vitro, 1/4 inch disk diffusion assay, various pathogens: Staphylococcus aureus, MIC = 100 μg/disk), antifungal (Candida albicans, MIC = 75 μg/disk, Pythium ultimum, MIC = 25 μg/disk). Ref: F. Kong, et al, JOC, 1993, 58, 6924│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)│S. Abbas, Mar. Drugs, 2011, 9, 2423 (rev)

4'

H

O HO O

O S

O

H N H O

OH

O

993 Regularoside A (3β,5α,6α,20R,22R,23S,24S)-22,23-Epoxyergost-9(11)-ene-3,6,20-triol 6-O-[β-D-fucopyranosyl-(1→2)-6-deoxy-β-D-glucopyranosyl-(1→4)-[6-deoxy-β-D-glucopyranosyl-(1→2)]6-deoxy-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside] 3-O-sulfate Type: Ergostane steroids. C58H96O28S [α]D = +12.3° (c = 0.5, MeOH) (Na salt). Source: Starfishes Halityle regularis and Archaster typicus. Pharm: Cytotoxic (HeLa, IC50 = 110 μmol/L; JB6 P+ CI41, 50 μmol/L, inactive). Ref: R. Riccio, et al, JNP, 1985, 48, 756│A. A. Kicha, et al, BoMCL, 2010, 20, 3826

392

2 Steroids

H OH

O

H H H HO

O S O

O

H OO

HO O O OH O

OH

OH

O

OH

O

O

OH

OH

O O OH

HO

OH

O

BD-fucop OH

994 Remeisterol (3β,23ξ,25ξ)-23,26-Dimethylergosta-5,24(28)-dien-3-ol Type: Ergostane steroids. C30H50O Source: Soft corals Sinularia leptoclados and Sinularia remei. Pharm: Hypotensor; antiarrhythmix. Ref: K. Long, et al, CA, 1982, 97, 107456h

H H

HO

995 Sanguinoside C (3β,4β,5α,6β,8β,15α,22E,24R,25S)-Ergost-22-ene-3,4,6,8,15,26-hexol 3-O-(2,3,4-tri-Omethyl-β-D-xylopyranoside) Type: Ergostane steroids. C36H62O10 Cryst. (MeOH), mp 178–179.5 °C, [α]D20 = −13° (c = 0.1, EtOH). Source: Starfish Henricia sanguinolenta (psychrophilic, cold water). Pharm: Cytotoxic (fertilized sea urchin eggs, moderate). Ref: E. V. Levina, et al, Russ. Chem. Bull., 2003, 52, 1623; 2005, 31, 467│M.D. Lebar, et al, NPR, 2007, 24, 774 (rev)

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

H

393

OH

OH OH

O

OO

O OH

O

OH

996 9,11-Seco-24-hydroxydinosterol 3,11,24-Trihydroxy-4,23-dimethyl-9,11-secoergost-22-en-9-one Type: Ergostane steroids. C30H52O4 Gum, [α]D = −11.4° (c = 0.08, CHCl3), [α]D = +6.8° (c = 2.7, MeOH). Source: Gorgonians Pseudopterogorgia americana and Pseudopterogorgia sp. (Florida). Pharm: PKCs inhibitor (PKC α, βI, βII, γ, δ, ε, η and ξ, IC50 = 12–50 μmol/L); cytotoxic (3–13 μmol/L with tritiated thymidine (3H-T), inhibits MCF7 proliferation). Ref: S. L. Miller, et al, Tet. Lett., 1995, 36, 1227│H. He, et al, Tetrahedron, 1995, 51, 51 OH HO H O H

HO

H

997 Sinulabasterol Type: Ergostane steroids. C30H46O6 Amorph. powder, [α]D25 = −17.6° (c = 0.27, CHCl3). Source: Soft coral Sinularia abrupta. Pharm: Antihistaminic (powerful). Ref: N. Shoji, et al, J. Pharm. Sci., 1994, 83, 761

HO HO OH

H

O

H

O O

998 Sinularoside A Type: Ergostane steroids. C34H56O7 Source: Soft coral Sinularia humilis (South China Sea). Pharm: Antifungal; Antimicroalga; antibacterial (gram-positive bacteria). Ref: P. Sun, et al, JNP, 2012, 75, 1656

394

2 Steroids

HO H O HO

H

O

H

HO

O OH

999 Sinularoside B Type: Ergostane steroids. C36H58O8 Source: Soft coral Sinularia humilis (South China Sea). Pharm: Antifungal; Antimicroalga; antibacterial (gram-positive bacteria). Ref: P. Sun, et al, JNP, 2012, 75, 1656

HO H

O

O H

O

O H

HO

O OH

1000 Stoloniferone A Type: Ergostane steroids. C29H46O3 Cryst. (MeCN), mp 148 °C, [α]D = +38.5° (CHCl3). Source: Soft coral Clavularia viridis (Okinawa). Pharm: Cytotoxic (P388); antiinflammatory. Ref: M. Kobayashi, et al, Tet. Lett., 1984, 25, 5925

H

HO O

H H

H

O

1001 Stoloniferone B Type: Ergostane steroids. C29H46O3 Cryst. (MeCN), mp 150 °C, [α]D = +33° (CHCl3). Source: Soft coral Clavularia viridis (Okinawa). Pharm: Cytotoxic (P388); antiinflammatory. Ref: M. Kobayashi, et al, Tet. Lett., 1984, 25, 5925

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

395

H HO O

H H

H

O

1002 Stoloniferone C Type: Ergostane steroids. C29H48O3 Cryst. (MeCN), mp 148°, [α]D = +40° (CHCl3). Source: Soft coral Clavularia viridis (Okinawa). Pharm: Cytotoxic (P388); antiinflammatory. Ref: M. Kobayashi, et al, Tet. Lett., 1984, 25, 5925

H

HO O

H H

H

O

1003 Stoloniferone E Type: Ergostane steroids. C28H44O3 Amorph. solid, [α]D25 = +10° (c = 0.05, CHCl3). Source: Soft coral Clavularia viridis. Pharm: Cytotoxic (A549, ED50 = 0.00032 μg/mL; HT29, ED50 = 0.0091 μg/mL; P388, ED50 = 0.00012 μg/mL). Ref: C. -Y. Duh, et al, JNP, 2002, 65, 1535

O

H

HO H

OH

1004 Stoloniferone F Type: Ergostane steroids. C28H46O5 Amorph. solid, [α]D25 = −30.6° (c = 0.11, CHCl3). Source: Soft coral Clavularia viridis. Pharm: Cytotoxic (A549, ED50 = 3.69 μg/mL; HT29, ED50 = 6.46 μg/mL; P388, ED50 = 2.36 μg/mL). Ref: C. -Y. Duh, et al, JNP, 2002, 65, 1535

396

2 Steroids

O

H

HO H

HO

OH OH

1005 Stoloniferone G 2,5,6,11-Tetrahydroxyergosta-3,24(28)-dien-1-one Type: Ergostane steroids. C28H44O5 Amorph. solid, [α]D25 = −21.7° (c = 0.12, CHCl3). Source: Soft coral Clavularia viridis. Pharm: Cytotoxic (A549, ED50 = 3.58 μg/mL; HT29, ED50 = 5.86 μg/mL; P388, ED50 = 2.12 μg/mL). Ref: C. -Y. Duh, et al, JNP, 2002, 65, 1535

O

H

HO H

HO

OH

OH

1006 Stoloniferone T (2β,5β,6β,11α,24S)-2,5,6,11-Tetrahydroxyergost-3-en-1-one Type: Ergostane steroids. C28H46O5 Amorph. solid, [α]D25 = +61.2° (c = 0.1, CHCl3). Source: Soft coral Clavularia viridis. Pharm: Anti-inflammatory (LPS-stimulated RAW 264.7 cell, upregulation of pro-inflammatory iNOS and COX-2 protein, 10 μmol/L, reduced levels of iNOS protein 40.2% compared with control cells stimulated with LPS; 10 μmol/L, reduced levels of COX-2 protein 58.4%). Ref: C. -H. Chang, et al, Steroids, 2008, 73, 562

O

H

HO H

HO

OH

OH

1007 Stoloniolide I Type: Ergostane steroids. C28H42O3 Source: Soft coral Clavularia viridis. Pharm: Antineoplastic. Ref: K. Iguchi, et al, Chem. Lett., 1995, 1109

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

397

H

HO

O O

1008 Stoloniolide II Type: Ergostane steroids. C28H44O3 Source: Soft coral Clavularia viridis. Pharm: Antineoplastic. Ref: K. Iguchi, et al, Chem. Lett., 1995, 1109

H

HO

O O

1009 Topsentiasterol sulfate A Type: Ergostane steroids. C30H46O16S3 [α]D = +48.4° (c = 0.2, MeOH) (tri-Na sat). Source: Sponge Topsentia sp. (Okinawa). Pharm: Antibacterial (Pseudomonas aeruginosa and Escherichia coli, 10 μg/disk). Ref: N. Fusetani, et al, Tetrahedron, 1994, 50, 7765

HO

S

O O HO

S

H

O

O O

OH

H

O

H OH O O S O OH

O

O

398

2 Steroids

1010 Topsentiasterol sulfate B Type: Ergostane steroids. C30H44O16S3 [α]D = +13.1° (c = 0.1, MeOH) (tri-Na sat). Source: Sponge Topsentia sp. (Okinawa). Pharm: Antibacterial (Pseudomonas aeruginosa and Escherichia coli, 10 μg/disk). Ref: N. Fusetani, et al, Tetrahedron, 1994, 50, 7765

HO O O HO

H

O S

S

H

O

O O

OH

H

O

O HO

O

O S

O

OH

1011 Topsentiasterol sulfate C Type: Ergostane steroids. C30H46O15S3 [α]D = +24.8° (c = 0.1, MeOH) (tri-Na sat). Source: Sponge Topsentia sp. (Okinawa). Pharm: Antibacterial (Pseudomonas aeruginosa and Escherichia coli, 10 μg/disk). Ref: N. Fusetani, et al, Tetrahedron, 1994, 50, 7765

HO O O HO

H

O S

S

H

O

O O

OH

H

O

O

O

O S O OH

1012 Topsentiasterol sulfate D Type: Ergostane steroids. C30H48O14S3 [α]D = +9.3° (c = 0.1, MeOH) (tri-Na sat). Source: Sponge Topsentia sp. (Okinawa). Pharm: Antibacterial (Pseudomonas aeruginosa and Escherichia coli, 10 μg/disk); antifungal (Mortierella remannianus and Candida albicans, 10 μg/disk). Ref: N. Fusetani, et al, Tetrahedron, 1994, 50, 7765

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

HO O O HO

H

O S

S

O

H

O

O O

399

OH

H

O

O S O OH

1013 Topsentiasterol sulfate E Type: Ergostane steroids. C31H52O13S3 [α]D = +58.3° (c = 0.1, MeOH). Source: Sponge Topsentia sp. (Okinawa). Pharm: Antibacterial (Pseudomonas aeruginosa and Escherichia coli, 10 μg/disk); antifungal (Mortierella remannianus and Candida albicans, 10 μg/disk). Ref: N. Fusetani, et al, Tetrahedron, 1994, 50, 7765

HO

S

O O HO

H

O

S

H

O

O O

OH

H

O

O S

O

OH

1014 3β,5α,9α-Trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one Type: Ergostane steroids. C28H44O4 Source: Deep-sea fungus Aspergillus versicolor ZBY-3. Pharm: Cytotoxic (K562, 100 μg/mL). Ref: Y. Dong, et al, Mar. Drugs, 2014, 12, 4326

H

OH HO

OH O

400

2 Steroids

1015 Wondosterol A Type: Ergostane steroids. C39H64O13 Amorph. solid, [α]D23 = +38.4° (c = 1.2, MeOH). Source: Sponges Poecillastra wondoensis and Jaspis wondoensis (association). Pharm: Antibacterial (Pseudomonas aeruginosa and Escherichia coli, 10 μg/disk); cytotoxic (P388, IC50 = 46 μg/mL). Ref: G, Ryu, et al, Tetrahedron, 1999, 55, 13171 OH HO O

HO

O

OH HO

H

O

O

H OH OH

HO OH

1016 Yonarasterol A Type: Ergostane steroids. C30H46O5 Amorph. solid, [α]D25 = −1.1° (c = 0.47, CHCl3). Source: Soft coral Clavularia viridis (Okinawa). Pharm: Cytotoxic (DLDH, IC50 = 3 μg/mL; Molt4, IC50 = 2.5 μg/mL). Ref: M. Iwashima, et al, Steroids, 2000, 65, 130; 2001, 66, 25

H

HO O H

OH O O

1017 Yonarasterol B Type: Ergostane steroids. C30H48O5 Amorph. solid, [α]D25 = +6° (c = 0.4, CHCl3). Source: Soft coral Clavularia viridis (Okinawa). Pharm: Cytotoxic (DLDH, IC50 = 3 μg/mL; Molt4, IC50 = 3 μg/mL). Ref: M. Iwashima, et al, Steroids, 2000, 65, 130; 2001, 66, 25

2.8 Ergostane Steroids (Excluding Withanolides) (C28)

401

H

HO O

OH O

O

1018 6-epi-Yonarasterol B Type: Ergostane steroids. C30H48O5 White powder, mp 93–94 °C, [α]D25 = −22° (c = 0.05, CHCl3). Source: Gorgonian Echinomuricea sp. (Taiwan waters). Pharm: Antioxidant (superoxide anion scavenger, IC50 = (2.98 ± 0.29)μg/mL; 10 μg/mL, InRt = (89.76 ± 5.63)%, control DPI, IC50 = (0.82 ± 0.31)μg/mL); elastase release inhibitor (stimulated hmn neutrophils, response to fMLP/CB, IC50 = (1.13 ± 0.55)μg/mL, InRt = (95.54 ± 6.17)%, control Elastatinal, IC50 = (31.82 ± 5.92)μg/mL). Ref: H. -M. Chung, et al, Mar. Drugs, 2012, 10, 1169

H

HO O H H

H

OH O O

1019 Yonarasterol E 4,5-Epoxy-6,11-dihydroxyergost-2-en-1-one Type: Ergostane steroids. C28H44O4 Amorph. solid, [α]D25 = −14.5° (c = 0.2, CHCl3). Source: Soft coral Clavularia viridis (Okinawa). Pharm: Cytotoxic (DLDH, IC50 = 0.02 μg/mL; Molt4, IC50 = 0.01 μg/mL). Ref: M. Iwashima, et al, Steroids, 2000, 65, 130; 2001, 66, 25

H

HO O H

6

O

OH

402

2 Steroids

2.9 27-Norergostane Steroids 1020 Leviusculoside J (3β,6β,8β,15α,16β,22E,24ξ)-27-Norergosta-4,22-diene-3,6,8,15,16,26-hexol 3-O-(2,3-di -O-methyl-β-D-xylopyranoside) Type: 27-Norergostane steroids. C34H56O10 Amorph. powder, [α]D = −12° (c = 0.1, MeOH). Source: Starfish Henricia leviuscula (psychrophilic, cold water, Sea of Okhotsk). Pharm: Hemolytic (mouse-erythrocytes assay, HC50 = 80 μmol/L). Ref: N. V. Ivanchina, et al, JNP, 2006, 69, 224│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

OH H OH

HO

O O

OH OH

O OH

O

2.10 Withanolide Steroids (C28) 1021 Minabeolide 1 3-Oxowitha-1,4,24-trienolide Type: Withanolide steroids. C28H38O3 Colorless oil, [α]D24 = +35° (c = 0.20, CHCl3). Source: Soft corals Paraminabea acronocephala (Pingtung county, Taiwan) and Minabea sp. Pharm: Cytotoxic (HepG2, Hep3B, MDAMB-231, MCF7 and A549; selective cytotoxicity toward HepG2, IC50 = 5.2 μmol/L; MCF7, IC50 = 18.7 μmol/L); anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS to (9.6 ± 1.9)%; inhibition of LPS induced COX-2 expression, reduced COX-2 to (18.3 ± 7.2)%). Ref: M. B. Ksebati,et al, JOC, 1988, 53, 3926│C. -H. Chao, et al, JNP, 2011, 74, 1132

H H H O

O O

H

2.10 Withanolide Steroids (C28)

403

1022 Minabeolide 2 Type: Withanolide steroids. C30H40O5 Colorless oil, [α]D24 = +45° (c = 0.32, CHCl3). Source: Soft corals Paraminabea acronocephala (Pingtung county, Taiwan) and Minabea sp. Pharm: Anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS to (45.7 ± 7.7)%; inhibition of LPS induced COX-2 expression, reduced COX-2 to (51.2 ± 11.5)%). Ref: M. B. Ksebati,et al, JOC, 1988, 53, 3926│C. -H. Chao, et al, JNP, 2011, 74, 1132 O O H

O

H H

O H

O

1023 Orthoesterol C disulfate Type: Withanolide steroids. C33H56O11S2 Amorph. powder. Source: Sponge Petrosia weinbergi. Pharm: Antiviral. Ref: J. L. Giner, et al, Steroids, 1999, 64, 820 O

OH S

O

O

28 24R

O O

S OH

O

H H

O

O

O

1024 Paraminabeolide A Type: Withanolide steroids. C28H36O4 Amorph. solid, [α]D24 = +83° (c = 0.18, CHCl3). Source: Soft coral Paraminabea acronocephala (Pingtung county, Taiwan). Pharm: Cytotoxic (HepG2, Hep3B, MDA-MB-231, MCF7 and A549; selective cytotoxicity toward HepG2, IC50 = 8.0 μmol/L); anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS to (11.0 ± 7.7)%). Ref: C. -H. Chao, et al, JNP, 2011, 74, 1132

404

2 Steroids

O

O

O

H H H

H

O

1025 Paraminabeolide B Type: Withanolide steroids. C30H42O5 Amorph. solid, [α]D24 = +8° (c = 0.09, CHCl3). Source: Soft coral Paraminabea acronocephala (Pingtung county, Taiwan). Pharm: Cytotoxic (MDA-MB-231, IC50 = 19.3 μmol/L; MCF7, IC50 = 14.9 μmol/L); antiinflammatory (Western blot analysis, 10 μmol/L, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS to (7.3 ± 1.0)%). Ref: C. -H. Chao, et al, JNP, 2011, 74, 1132

O O H

O

O

H H

H

O

1026 Paraminabeolide C Type: Withanolide steroids. C30H42O6 Amorph. solid, [α]D24 = +13° (c = 0.09, CHCl3). Source: Soft coral Paraminabea acronocephala (Pingtung county, Taiwan). Pharm: Anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS to (37.9 ± 9.9)%). Ref: C. -H. Chao, et al, JNP, 2011, 74, 1132 OH

O O H

O

H H O

H

O

2.10 Withanolide Steroids (C28)

405

1027 Paraminabeolide D Type: Withanolide steroids. C28H40O4 Amorph. solid, [α]D24 = +28° (c = 0.09, CHCl3). Source: Soft coral Paraminabea acronocephala (Pingtung county, Taiwan). Pharm: Anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS to (43.4 ± 9.5)%). Ref: C. -H. Chao, et al, JNP, 2011, 74, 1132 OH H O

H H

O

H

O

1028 Paraminabeolide E Type: Withanolide steroids. C28H40O4 Amorph. solid, [α]D24 = −33° (c = 0.12, CHCl3). Source: Soft coral Paraminabea acronocephala (Pingtung county, Taiwan). Pharm: Anti-inflammatory (Western blot analysis, 10 μmol/L, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS to ≈ 70%). Ref: C. -H. Chao, et al, JNP, 2011, 74, 1132 OH H O

H H

O

H

O

1029 Sinubrasolide A Type: Withanolide steroids. C28H38O4 Source: Soft coral Sinularia brassica (cultured specimens, Taiwan). Pharm: Cytotoxic (mild). Ref: C. -Y. Huang, et al, JNP, 2013, 76, 1902 O O H H O

H H O

H

406

2 Steroids

1030 Sinubrasolide B Type: Withanolide steroids. C28H38O4 Source: Soft coral Sinularia brassica (cultured specimens, Taiwan). Pharm: Cytotoxic (mild). Ref: C. -Y. Huang, et al, JNP, 2013, 76, 1902 O O H H O

H H

H

O

1031 Sinubrasolide E Type: Withanolide steroids. C28H38O5 Source: Soft coral Sinularia brassica (cultured specimens, Taiwan). Pharm: Cytotoxic (mild). Ref: C. -Y. Huang, et al, JNP, 2013, 76, 1902 OH

H H H

O

O

O

H

O

2.11 Stigmastane Steroids (C29) 1032 Acanthifolioside D Type: Stigmastane steroids. C35H62O8 White amorph. solid, [α]D20 = −15.6° (c = 0.13, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Cytotoxic (L-6, IC50 = 7.0 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L); antiprotozoal (Trypanosoma brucei rhodesiense, IC50 = 30.8 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 15.3 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L; Leishmania donovani, IC50 = 5.7 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L; Plasmodium falciparum, IC50 = 15.0 μmol/L, control Chloroquine, IC50 = 0.20 μmol/L). Ref: E. L. Regalado, et al, Tetrahedron, 2011, 67, 1011

2.11 Stigmastane Steroids (C29)

407

H OH H

O OH

H

H

O

OH

HO H

OH HO

1033 Acanthifolioside E Type: Stigmastane steroids. C35H60O8 White amorph. solid, [α]D20 = −30.0° (c = 0.07, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Cytotoxic (L-6, IC50 = 8.5 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L); antiprotozoal (Trypanosoma brucei rhodesiense, IC50 = 27.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 10.6 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L; Leishmania donovani, IC50 = 9.4 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L; Plasmodium falciparum, IC50 = 12.9 μmol/L, control Chloroquine, IC50 = 0.20 μmol/L). Ref: E. L. Regalado, et al, Tetrahedron, 2011, 67, 1011

H H

OH O OH

H

H

OH

O

HO OH HO

1034 Acanthifolioside F Type: Stigmastane steroids. C47H80O19 White amorph. solid, [α]D20 = −20.7° (c = 0.15, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Cytotoxic (L-6, IC50 = 89.9 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L); antiprotozoal (Trypanosoma brucei rhodesiense, IC50 = 24.8 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 77.4 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L; Leishmania donovani, IC50 = 29.0 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L; Plasmodium falciparum, IC50 = 37.0 μmol/L, control Chloroquine, IC50 = 0.20 μmol/L). Ref: E. L. Regalado, et al, Tetrahedron, 2011, 67, 1011

408

2 Steroids

H H H HO

H

HO

OH HO O

O OH

OH O O

O HO HO

OH O

O

OH OH

OH

1035 Acetyltheonellasterol Type: Stigmastane steroids. C32H52O2 Source: Lithistid sponge Theonella swinhoei (Pingtung county, Taiwan). Pharm: Cytotoxic (DLD-1, IC50 > 20 μg/mL; T47D, IC50 > 20 μg/mL; HCT116, IC50 > 20 μg/mL; MCF7, IC50 > 20 μg/mL; MDA-MB-231, IC50 > 20 μg/mL; K562, IC50 = 13.7 μg/mL, Doxorubicin, IC50 = 0.14 μg/mL; Molt4, IC50 = 17.8 μg/mL, Doxorubicin, IC50 = 0.009 μg/mL). Ref: J. -K. Guo, et al, Mar. Drugs, 2012, 10, 1536

H

O

H O

H

1036 Acodontasteroside D (3β,4β,5α,6α,8β,15β,24R)-Stigmastane-3,4,6,8,15,29-hexol 29-O-[β-D-xylopyranosyl-(1→2)β-D-xylopyranoside] Type: Stigmastane steroids. C39H68O14 [α]D = +8° (c = 1, MeOH). Source: Starfish Acodontaster conspicuus (Antarctic). Pharm: Antibacterial (Antarctic marine bacteria McM13.3 and McM32.2, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, JNP, 1997, 60, 959

2.11 Stigmastane Steroids (C29)

409

29

H

O

24R

O

OH

OH

OH OO OH

OH HO H OH

OH

OH

OH

1037 Acodontasteroside F (3β,4β,5α,6α,8β,15β,24R)-Stigmastane-3,4,6,8,15,29-hexol 29-O-[2-O-methyl-β-Dxylopyranosyl-(1→2)-β-D-xylopyranoside] Type: Stigmastane steroids. C40H70O14 [α]D = −14.4° (c = 1, MeOH). Source: Starfish Acodontaster conspicuus (Antarctic). Pharm: Antibacterial (Antarctic marine bacteria McM13.3 and McM32.2, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, JNP, 1997, 60, 959 29

H OH

O

24R

O

OH OH OO

OH

OH

HO H OH

OH

OH

O

1038 Acodontasteroside I (3β,6α,15β,24(28)E)-Stigmasta-8(14),24(28)-diene-3,6,15,29-tetrol 29-O-β-D-xylopyranoside Type: Stigmastane steroids. C34H56O8 [α]D = −20.8° (c = 1, MeOH). Source: Starfish Acodontaster conspicuus (Antarctic). Pharm: Antibacterial (Antarctic marine bacteria McM13.3 and McM32.2, may play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus). Ref: S. De Marino, et al, JNP, 1997, 60, 959 O

O

29

OH OH

H OH

OH HO OH

410

2 Steroids

1039 Agosterol C6 Type: Stigmastane steroids. C33H52O8 [α]D = +37.7° (c = 0.2, CHCl3). Source: Sponge Spongia sp. (Japan waters). Pharm: Reversal of MDR (10 μg/mL: KB-C2, InRt = (15 ± 7)%; KB-CV60, InRt = (21 ± 4)%; KB-3-1, InRt = (19 ± 7)%). Ref: S. Aoki, et al, Tetrahedron, 1999, 55, 13965 OH

OH

OH

HO O

H

O

O

O

1040 Archasteroside A (3β,5α,6α,22R,23S,24S)-22,23-Epoxystigmast-9(11)-ene-3,6,20-triol 6-O-[β-D-fucopyranosyl-(1→2)-6-deoxy-β-D-glucopyranosyl-(1→4)-[6-deoxy-β-D-glucopyranosyl-(1→2)]6-deoxy-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside] 3-O-sulfate Type: Stigmastane steroids. C59H98O28S Amorph. powder, [α]D20 = +4.8° (c = 0.2, MeOH). Source: Starfish Archaster typicus (Quang Ninh, Vietnam). Pharm: Cytotoxic (HeLa, IC50 = 24 μmol/L; JB6 P+ CI41, IC50 = 37 μmol/L). Ref: A. A. Kicha, et al, BoMCL, 2010, 20, 3826 H OH

O H H

H HO O

O 3

S O

H OO

HO O O OH O

OH

O

OH

O

O

OH

OH

O O OH

HO

OH

O

BD-fucop OH

OH

2.11 Stigmastane Steroids (C29)

411

1041 Clathsterol Type: Stigmastane steroids. C39H66O15S2 Powder, [α]D = +28° (c = 0.35, MeOH). Source: Sponge Clathria sp. Pharm: HIV-1 reverse transcriptase Inhibitor. Ref: A. Rudi, et al, JNP, 2001, 64, 1451

O O O O

HO O

O S

OH S

H

O H

O

O OH O

O O

1042 (3β,5α,8α,24R)-5,8-Epidioxy-24-hydroperoxystigmasta-6,28-dien-3-ol Type: Stigmastane steroids. C29H46O5 Source: Sponge Lendenfeldia chondrodes (Palau, Oceania). Pharm: Antifoulant (blue mussel Mytilus edulis galloprovincialis). Ref: Y. Sera, et al, JNP, 1999, 62, 152 OH O H

HO

O O

1043 (3β,5α,8α,24S)-5,8-Epidioxy-24-hydroperoxystigmasta-6,28-dien-3-ol Type: Stigmastane steroids. C29H46O5 Source: Sponge Lendenfeldia chondrodes (Palau, Oceania). Pharm: Antifoulant (blue mussel Mytilus edulis galloprovincialis). Ref: Y. Sera, et al, JNP, 1999, 62, 152 OH O H

HO

O O

412

2 Steroids

1044 24-Ethylcholesta-4,24(28)-diene-3,6-dione Type: Stigmastane steroids. C29H44O2 mp 134–136 °C, [α]D28 = −39° (c = 0.24, CHCl3). Source: Brown alga Turbinaria conoides (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.9 μg/mL, KB, ED50 = 4.6 μg/mL, A549, ED50 = 2.3 μg/mL, HT29, ED50 = 1.2 μg/mL). Ref: J.-H. Sheu, et al, JNP, 1999, 62, 224

H H

O O

1045 (24R)-24-Ethyl-5α-cholestane-3β,5,6β,15α,29-pentol 29-sulfate Type: Stigmastane steroids. C29H52O8S [α]D = +15.0°. Source: Starfish Luidia clathrata (Gulf of Mexico). Pharm: Antibacterial (inhibits growth of gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus); antifoulant (inhibits settlement of barnacle larvae). Ref: M. Iorizzi, et al, JNP, 1995, 58, 653 O

29

S O

H

OH O

24

H 3

6

OH

HO OH OH

1046 (24S)-24-Ethyl-7α-hydroperoxycholesta-5,25-dien-3β-ol Type: Stigmastane steroids. C29H48O3 White powder, mp 127–128 °C, [α]D24 = −87.6° (c = 0.14, CHCl3). Source: Green alga Codium arabicum. Pharm: Cytotoxic (P388, ED50 = 0.4 μg/mL; KB, ED50 = 1.0 μg/mL; A549, ED50 = 0.5 μg/mL; HT29, ED50 = 1.0 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1995, 58, 1521

2.11 Stigmastane Steroids (C29)

413

H

HO

O

OH

1047 (24S)-24-Ethyl-5α-hydroperoxycholesta-6,25-dien-3β-ol Type: Stigmastane steroids. C29H48O3 White powder, mp 152–153 °C, [α]D24 = −9.1° (c = 0.07, CHCl3). Source: Green alga Codium arabicum. Pharm: Cytotoxic (P388, ED50 = 0.5 μg/mL; KB, ED50 = 1.0 μg/mL; A549, ED50 = 1.1 μg/mL; HT29, ED50 = 0.9 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1995, 58, 1521

H H

HO O OH

1048 (24S)-24-Ethyl-3-oxocholesta-4,25-dien-6β-ol Type: Stigmastane steroids. C29H46O2 White powder, mp 194 °C. Source: Green alga Codium arabicum. Pharm: Cytotoxic (P388, ED50 = 0.7 μg/mL; KB, ED50 = 1.3 μg/mL; A549, ED50 = 2.1 μg/mL; HT29, ED50 = 0.3 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1995, 58, 1521

H H

O OH

1049 Fucosterol Type: Stigmastane steroids. C29H48O Needles (MeOH), mp 124 °C, [α]D20 = −38° (CHCl3), characteristic sterol of brown algae. Source: Brown algae Sargassum tortile,

414

2 Steroids

Cystoseira sp., Bifurcaria sp. and Turbinaria conoides (Fucosterol is a characteristic sterol of brown algae), sponges Stelletta clarella, Tethya aurantia, Lissodendoryx noxiosa, Haliclona permollis and Haliclona spp., gorgonian Eunicea fusca (Santa Marta Bay, Caribbean Sea, Colombia), scallop Patinopecten yessoensis. Pharm: Cytotoxic (P388, ED50 = 17.2 μg/mL, control Etoposide, ED50 = 0.24 μg/mL). Ref: I. Heilbron, et al, JCS, 1934, 1572│Y. M. Sheikh, et al, Tetrahedron, 1974, 30, 4095│W. C. M. C. Kokke, et al, JOC, 1984, 49, 3742│A. Numata, et al, CPB, 1991, 39, 2129│L. Castellanos, et al, Biochem. Syst. Ecol. 2003, 31, 1163│E. Reina, et al, BoMCL, 2011, 21, 5888

H H

HO

1050 24ξ-Hydroperoxy-24-ethylcholesta-4,28(29)-diene-3,6-dione Type: Stigmastane steroids. C29H44O4 [α]D34 = −39° (c = 0.075, CHCl3). Source: Brown alga Turbinaria conoides (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.4 μg/mL, KB, ED50 = 1.8 μg/mL, A549, ED50 = 1.8 μg/mL, HT29, ED50 = 1.7 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1999, 62, 224

OH O H H

O O

1051 24ξ-Hydroperoxy-6β-hydroxy- 24-ethylcholesta-4,28(29)-dien-3-one Type: Stigmastane steroids. C29H46O4 mp 151–152 °C, [α]D27 = +16° (c = 0.34, CHCl3). Source: Brown alga Turbinaria conoides (Taiwan waters). Pharm: Cytotoxic (P388, ED50 = 0.8 μg/mL, KB, ED50 = 4.0 μg/mL, A549, ED50 = 2.5 μg/mL, HT29, ED50 = 1.4 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1999, 62, 224

2.11 Stigmastane Steroids (C29)

415

OH O H H

O OH

1052 24-Hydroperoxy-24-vinylcholesterol Type: Stigmastane steroids. C29H48O3 Cryst., mp 140–145 °C, [α]D23 = −28.9° (c = 1.33, CHCl3). Source: Ascidians Phallusia mamillata and Ciona intestinalis. Pharm: Cytotoxic. Ref: M. Guyot, et al, Tet. Lett., 1982, 23, 1905│M. Guyot, et al, J. Chem. Res. (S), 1983, 188 OH O H H

HO

1053 6β-Hydroxy-24-ethylcholesta-4,24(28)-dien-3-one Type: Stigmastane steroids. C29H46O2 mp 171.5–173.0 °C, [α]D28 = +25° (c = 0.09, CHCl3). Source: Brown alga Turbinaria conoides (Taiwan waters). Pharm: Cytotoxic (P388, KB, A549, HT29, ED50 = 0.6 μg/mL, 5.9 μg/mL, 3.1 μg/mL, 0.4 μg/mL respectively). Ref: J. -H. Sheu, et al, JNP, 1999, 62, 224

H H

O OH

1054 7α-Hydroxytheonellasterol Type: Stigmastane steroids. C30H50O2 Oil, [α]D = +19.4° (c = 0.35, CHCl3). Source: Lithistid sponge Theonella swinhoei (South China Sea). Pharm: Cytotoxic

416

2 Steroids

(an undisclosed panel of eight cell lines, mean IC50 = 29.5 μmol/L). Ref: P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

H HO

OH

H

1055 Kiheisterone A Type: Stigmastane steroids. C29H40O5 Colorless glass, [α]D = +144° (c = 1.72, MeOH). Source: An unidentified sponge (order Poecilosclerida, Maui). Pharm: Cytotoxic (A549 and HT29, IC50 = 5.0 μg/mL; P388, IC50 = 2.5 μg/mL; nontumorous monkey kidney cells, IC50 = 0.2 μg/mL). Ref: J. R. Carney, et al, JOC, 1992, 57, 6637 O

H

HO

O

H

HO

O

H

H

1056 Kiheisterone B Type: Stigmastane steroids. C29H40O5 Fine white needles, mp 223–225 °C, [α]D = +19° (c = 0.70, CHCl3). Source: An unidentified sponge (order Poecilosclerida, Maui). Pharm: Cytotoxic (A549, IC50 = 5.0 μg/mL; HT29, IC50 = 5.0 μg/mL; P388, IC50 = 2.5 μg/mL; nontumorous monkey kidney cells, IC50 = 0.2 μg/mL). Ref: J. R. Carney, et al, JOC, 1992, 57, 6637 O H HO H H

O

HO H

O

2.11 Stigmastane Steroids (C29)

417

1057 Linckoside L7 (3β,6β,15α,16β,22E,24R)-Stigmasta-4,22-diene-3,6,8,15,16,29-hexol 3-O-(2-O-methyl-β-Dxylopyranoside) 29-O-β-D-xylopyranoside 15-sulfate Type: Stigmastane steroids. C40H66O17S Amorph. solid, [α]D20 = −20.4° (c = 0.25, MeOH). Source: Starfish Linckia laevigata (Vietnam). Pharm: Cytotoxic (fertilized egg cells of sea urchin Strongyocentrotus intermedius at eight blastomer stage, ED100 = 50 μg/mL). Ref: A. A. Kicha, et al, Chem. Nat. Compd. (Engl. Transl.), 2007, 43, 76

OO

24R

H

OH OH

OH

15

OH

O 3

O

O

S

O

OH

OH O

OH

OH OH O

1058 Linckoside N (3β,6β,15α,16β,22E,24R,25S)-Stigmasta-4,22-diene-3,6,8,15,16,26-hexol 3-O-(2-O-methylβ-D-xylopyranoside) 26-O-β-D-xylopyranoside Type: Stigmastane steroids. C40H66O14 Amorph. solid, [α]D23 = −36° (c = 0.11, MeOH). Source: Starfish Linckia laevigata (Okinawa). Pharm: Nervous system activity (neurite outgrowth inducer, IC50 (apparent) > 10 μmol/L, MMOA: dependent on xylose on side chain). Ref: C. Han, et al, J. Nat. Med. (Tokyo), 2007, 61, 138

25S

H OH

OH

3

O

15

26

24R

OH

OO OH OH OH

O OH

OH OH O

1059 Linckoside O (3β,6β,15α,16β,22E,24R)-Stigmasta-4,22-diene-3,6,8,15,16,29-hexol 3-O-(2-O-methyl-β-Dxylopyranoside) 29-O-β-D-xylopyranoside Type: Stigmastane steroids. C40H66O14

418

2 Steroids

Amorph. solid, [α]D18 = −33° (c = 0.12, MeOH). Source: Starfish Linckia laevigata (Okinawa). Pharm: Nervous system activity (neurite outgrowth inducer, IC50 (apparent) > 10 μmol/L, MMOA: dependent on xylose on side chain). Ref: C. Han, et al, J. Nat. Med. (Tokyo), 2007, 61, 138

OO

24R

H

OH OH

OH

15

OH

O

OH

OH

3

O OH

OH OH O

1060 Linckoside P (3β,6β,8β,15α,16β,24R)-Stigmast-4,25-diene-3,6,8,15,16,29-hexol 3-O-(2-O-methyl-βD-xylopyranoside) 29-O-β-D-xylopyranoside Type: Stigmastane steroids. C40H66O14 Amorph. solid, [α]D22 = −29° (c = 0.07, MeOH). Source: Starfish Linckia laevigata. Pharm: Nervous system activity (neurite outgrowth inducer, IC50 (apparent) > 10 μmol/L, MMOA: dependent on xylose on side chain). Ref: C. Han, et al, J. Nat. Med. (Tokyo), 2007, 61, 138

29

O 24R

H OH

15

O OH

OH OH

OH

3

O

OH

O OH

OH OH O

1061 Norselic acid A 24-Hydroxy-3-oxostigmasta-1,4,6,25-tetraen-18-oic acid Type: Stigmastane steroids. C29H40O4 Cryst. (CH2Cl2/hexane), mp 157–158 °C, [α]D20 = +53° (c = 0.2, CHCl3). Source: Sponge Crella sp. (Norsel Point, Palmer Station, Antarctica). Pharm: Antimicrobial (weak); antifeedant (mesograzers). Ref: W. S. Ma, et al, JNP, 2009, 72, 1842

2.11 Stigmastane Steroids (C29)

419

HO HOOC

H

H H

H

O

1062 Norselic acid B 24-Hydroxy-3-oxostigmasta-1,25-dien-18-oic acid Type: Stigmastane steroids. C29H44O4 Cryst., mp 201 °C, [α]D20 = +42° (c = 0.2, CHCl3). Source: Sponge Crella sp. (Norsel Point, Palmer Station, Antarctica). Pharm: Antimicrobial (weak); antifeedant (mesograzers). Ref: W. S. Ma, et al, JNP, 2009, 72, 1842 HO HOOC

H

H H O

H

H

1063 Norselic acid D 24-Hydroxy-3-oxostigmasta-4,25-dien-18-oic acid Type: Stigmastane steroids. C29H44O4 Glass, [α]D20 = +54° (c = 0.1, CHCl3). Source: Sponge Crella sp. (Norsel Point, Palmer Station, Antarctica). Pharm: Antimicrobial (weak); antifeedant (mesograzers). Ref: W. S. Ma, et al, JNP, 2009, 72, 1842 HO HOOC

H

H H

H

O

1064 Norselic acid E Type: Stigmastane steroids. C31H42O5 Glass, [α]D20 = +57° (c = 0.1, CHCl3). Source: Sponge Crella sp. (Norsel Point, Palmer Station, Antarctica). Pharm: Antimicrobial (weak); antifeedant (mesograzers). Ref: W. S. Ma, et al, JNP, 2009, 72, 1842

420

2 Steroids

O O HOOC

H

H H

H

O

1065 Pakisterol A Type: Stigmastane steroids. C35H58O6 Source: Soft coral Lobophytum sp. (Vietnam). Pharm: Cytotoxic (A549, IC50 = 29.3 μmol/L, control Mitoxantrone, IC50 = 6.1 μmol/L; HT29, IC50 = 23.8 μmol/L, Mitoxantrone, IC50 = 6.5 μmol/L). Ref: H. T. Nguyen, et al, Arch. Pharm. Res., 2010, 33, 503

H H OH

H

OO OH OH

OH

1066 Pandaroside A (3β,5α,14β,24R)-3,16-Dihydroxystigmast-16-ene-15,23-dione 3-O-[β-D-Glucopyranosyl -(1→2)-β-D-glucuronopyranoside] Type: Stigmastane steroids. C41H64O15 Amorph. solid, [α]D20 = +19.1° (c = 0.19, MeOH). Source: Sponge Pandaros acanthifolium. Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 9.1 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 52.2 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 19.7 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 17.6 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 48.9 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: N. Cachet, et al, Steroids, 2009, 74, 746

2.11 Stigmastane Steroids (C29)

421

O H OH O O HO

HO

O O

HO

H

O

H

O

O

HO

H

OH

OH

1067 Pandaroside A methyl ester Type: Stigmastane steroids. C42H66O15 Amorph. solid, [α]D20 = +7.8° (c = 0.27, MeOH). Source: Sponge Pandaros acanthifolium. Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 114 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 120 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 66.3 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 25 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 120 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: N. Cachet, et al, Steroids, 2009, 74, 746

O H O O O HO HO HO

HO

H O O

O

OH H

O

H

O

OH

1068 Pandaroside G 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyloxyuronic acid]-5α,14βporiferasta-7,16-diene-15,23-dione Type: Stigmastane steroids. C40H60O14 White amorph. solid, [α]D20 = +16.8° (c = 0.07, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 0.8 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 9.7 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L);

422

2 Steroids

Antileishmanial (Leishmania donovani, IC50 = 1.3 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 2.5 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 5.4 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O OH OH

HO

H

H

O

O HO OO

OO

O

H

OH

HO OH

1069 Pandaroside G methyl ester Type: Stigmastane steroids. C41H62O14 White amorph. solid, [α]D20 = +30.0° (c = 0.10, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 0.038 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 0.77 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 0.051 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 0.39 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 0.22 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O OH H

O

HO

O HO OO

OO

H

O

H

OH

HO OH

1070 Pandaroside H 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyloxyuronic acid]-5α,14βporiferast-16-ene-15,23-dione Type: Stigmastane steroids. C40H62O14 White amorph.

2.11 Stigmastane Steroids (C29)

423

solid, [α]D20 = +9.1° (c = 0.08, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 68.4 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 120 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 46.7 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 22.8 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 120 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O H H

OH

HO

O HO OO

OH H

O

H

OO OH

HO OH

1071 Pandaroside H methyl ester Type: Stigmastane steroids. C41H64O14 White amorph. solid, [α]D20 = +7.4° (c = 0.08, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 19.9 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 36.1 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 16.5 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 10.2 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 43.3 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O OH

H H

O

HO HO

O HO OO

OO OH

OH

H

H

O

424

2 Steroids

1072 Pandaroside I 16-Hydroxy-3β-O-[α-rhamnopyranosyl-(1→4)-β-D-glucopyranosyloxyuronic acid]5α,14β-poriferast-16-ene-15,23-dione Type: Stigmastane steroids. C41H64O14 White amorph. solid, [α]D24 = −13.0° (c = 0.10, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 19.2 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 70.8 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 36.0 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 25 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 120 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O OH

H HO HO

O

HO

H O

O HO

OH OO

H

O

H

OH

1073 Pandaroside I methyl ester Type: Stigmastane steroids. C42H66O14 White amorph. solid, [α]D20 = −11.7° (c = 0.18, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 27.2 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 21.7 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 28.7 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 13.0 μmol/L, control Chloroquine,IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 59.6 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O OH

H HO HO HO

H

O O O HO

O OO OH

H

H

O

2.11 Stigmastane Steroids (C29)

425

1074 Pandaroside J 3β-O-[β-D-Glucopyranosyl-(1→2)-β-D-glucopyranosyloxyuronic acid]-16-hydroxy-5α,14βporiferasta-16,24(241)-diene-15,23-dione Type: Stigmastane steroids. C41H62O15 White amorph. solid, [α]D20 = +4.0° (c = 0.10, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 14.5 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 83.4 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 36.1 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 24.3 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 78.0 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

O H OH O O HO HO HO

HO

H O O

O

OH H

O

H

O OH

1075 Pandaroside J methyl ester Type: Stigmastane steroids. C42H64O15 White amorph. solid, [α]D20 = +2.4° (c = 0.08, MeOH). Source: Sponge Pandaros acanthifolium (Martinique I., Caribbean Sea). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense, IC50 = 15.6 μmol/L, control Melarsoprol, IC50 = 0.010 μmol/L; Trypanosoma cruzi, IC50 = 70.5 μmol/L, control Benznidazole, IC50 = 2.64 μmol/L); Antileishmanial (Leishmania donovani, IC50 = 20.7 μmol/L, control Miltefosine, IC50 = 0.51 μmol/L); antimalarial (Plasmodium falciparum, IC50 = 12.4 μmol/L, control Chloroquine, IC50 = 0.2 μmol/L); cytotoxic (L-6, IC50 = 75.2 μmol/L, control Podophyllotoxin, IC50 = 0.012 μmol/L). Ref: E. L. Regalado, et al, JNP, 2010, 73, 1404

426

2 Steroids

O H O O O HO HO HO

HO

H O O

O

OH H

O

H

O OH

1076 (24R)-Stigmasta-4,25-diene-3,6-diol Type: Stigmastane steroids. C29H48O2 Needles, mp 242–243 °C. Source: Red alga Laurencia majuscula (South China Sea). Pharm: Cytotoxic. Ref: X. Xu, et al, Tianran Chanwu Yanjiu Yu Kaifa, 2001, 13, 5

H H

HO OH

1077 Stigmasta-4,24(28)-dien-3-one 24-Ethylidenecholest-4-en-3-one Type: Stigmastane steroids. C29H46O mp 83–84 °C, [α]D26 = +52° (c = 0.24, CHCl3). Source: Brown alga Turbinaria conoides (Taiwan waters). Pharm: Cytotoxic (P388, KB, A549, HT29, all ED50s > 50 μg/mL). Ref: J. -H. Sheu, et al, JNP, 1999, 62, 224

H H

O

2.11 Stigmastane Steroids (C29)

427

1078 Stigmast-25-ene-2,3,15,16,17,18-hexol 2-O-sulfate Type: Stigmastane steroids. C29H50O9S Solid (Phenethylammonium salt), [α]D = +0.3° (c = 0.15, MeOH). Source: Sponge Echinoclathria subhispida (South Australia). Pharm: Antifungal (Mortierella ranuznniun); cytotoxic (PC-9, IC50 = 600 μmol/L). Ref: H. Li, et al, Tet. Lett., 1993, 34, 5733

HO

OH O

S

OH O H

O

OH

OH HO H

1079 Theonellasterol B Type: Stigmastane steroids. C30H46O Pale yellow oil, [α]D25 = +1.6° (c = 0.08, MeOH). Source: Lithistid sponge Theonella swinhoei (Malaita I. and Vangunu I., Solomon Is.). Pharm: PXR (hmn nuclear pregnane receptor)-agonist/farnesoid-Xreceptor antagonist (Exposure of liver cells to this agent resulted in potent induction of PXR regulated genes and modulation of FXR-regulated genes, highlighting its pharmacological potential in treatment of liver disorders). Ref: S. De Marino, et al, JMC, 2011, 54, 3065

H

HO

H

1080 Theonellasterol C Type: Stigmastane steroids. C30H48O2 Pale yellow oil, [α]D25 = +5.7° (c = 0.16, MeOH). Source: Lithistid sponge Theonella swinhoei (Malaita I. and Vangunu I., Solomon Is.; South China Sea). Pharm: Affects nuclear receptors (using HepG2 cell transfected with FXR or PXR, partially activates FXR at 10 μmol/L; antagonist of FXR transactivation by chenodeoxycholic acid; agonist of PXR at 10 μmol/L). Ref: S. De Marino, et al, JMC, 2011, 54, 3065│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

428

2 Steroids

H

H HO

O

H

1081 Theonellasterol D Type: Stigmastane steroids. C31H52O3 White amorph. solid, [α]D25 = +3.3° (c = 0.17, MeOH). Source: Lithistid sponge Theonella swinhoei (Malaita I. and Vangunu I., Solomon Is.; South China Sea). Pharm: Affects nuclear receptors (using HepG2 cell transfected with PXR, agonist of PXR at 10 μmol/L). Ref: S. De Marino, et al, JMC, 2011, 54, 3065│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

O

OH

HO H

1082 Theonellasterol E Type: Stigmastane steroids. C30H50O3 White amorph. solid, [α]D25 = +34° (c = 0.1, MeOH). Source: Lithistid sponge Theonella swinhoei (Malaita I. and Vangunu I., Solomon Is.; South China Sea). Pharm: Affects nuclear receptors (using HepG2 cell transfected with FXR or PXR, antagonist of FXR transactivation by chenodeoxycholic acid; agonist of PXR at 10 μmol/L). Ref: S. De Marino, et al, JMC, 2011, 54, 3065│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

OH HO

H

OH

2.11 Stigmastane Steroids (C29)

429

1083 Theonellasterol F Type: Stigmastane steroids. C30H50O3 White amorph. solid, [α]D25 = +4.3° (c = 0.23, MeOH). Source: Lithistid sponge Theonella swinhoei (Malaita I. and Vangunu I., Solomon Is.; South China Sea). Pharm: Affects nuclear receptors (using HepG2 cell transfected with PXR, agonist of PXR at 10 μmol/L). Ref: S. De Marino, et al, JMC, 2011, 54, 3065│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

H

H HO

OH OH

H

1084 Theonellasterol G Type: Stigmastane steroids. C30H50O4 Pale yellow oil, [α]D25 = +68° (c = 1.0, MeOH). Source: Lithistid sponge Theonella swinhoei (South China Sea; Malaita I. and Vangunu I., Solomon Is.). Pharm: Affects nuclear receptors (using HepG2 cell transfected with FXR or PXR, antagonist of FXR transactivation by chenodeoxycholic acid; agonist of PXR at 10 μmol/L). Ref: S. De Marino, et al, JMC, 2011, 54, 3065│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

24

H

HO

OH

OH

HO H

1085 Theonellasterol H Type: Stigmastane steroids. C30H50O4 Pale yellow oil, [α]D25 = +16° (c = 0.1, MeOH). Source: Lithistid sponge Theonella swinhoei (South China Sea; Malaita I. and Vangunu I., Solomon Is.). Pharm: Affects nuclear receptors (using HepG2 cell transfected with FXR or PXR, antagonist of FXR transactivation by chenodeoxycholic acid; agonist of PXR at 10 μmol/L). Ref: S. De Marino, et al, JMC, 2011, 54, 3065│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

430

2 Steroids

24

H

HO

OH HO

OH

H

1086 Theonellasterol K Type: Stigmastane steroids. C30H50O3 Source: Lithistid sponge Theonella swinhoei (Pingtung county, Taiwan). Pharm: Cytotoxic (DLD-1, IC50 = 12.9 μg/mL; control Doxorubicin, IC50 = 0.42 μg/mL; T47D, IC50 = 12.0 μg/mL, Doxorubicin, IC50 = 0.28 μg/mL; HCT116, IC50 = 6.3 μg/mL, Doxorubicin, IC50 = 0.89 μg/mL; MCF7, IC50 = 11.5 μg/mL, Doxorubicin, IC50 = 2.2 μg/mL; MDA-MB-231, IC50 = 11.4 μg/mL, Doxorubicin, IC50 = 1.3 μg/mL; K562, IC50 = 4.3 μg/mL, Doxorubicin, IC50 = 0.14 μg/mL; Molt4, IC50 = 6.3 μg/mL, Doxorubicin, IC50 = 0.009 μg/mL). Ref: J. -K. Guo, et al, Mar. Drugs, 2012, 10, 1536

H

H

O

OH

HO H

1087 Topsentinol B (3β,7α,22Z)-24-Isopropylcholesta-5,22-diene-3,7-diol Type: Stigmastane steroids. C30H50O2 Needles, mp 216 °C, [α]D27 = −96° (c = 0.5, CHCl3). Source: Sponge Topsentia sp. (Okinawa). Pharm: Antifungal (Trichophyton mentagrophytes, MIC = 56 μg/mL). Ref: M, Ishibashi, et al, CPB, 1997, 45, 1435 22Z

H H

HO

OH

2.12 Gorgostane and Other Cyclopropacholestane Steroids

431

2.12 Gorgostane and Other Cyclopropacholestane Steroids 1088 Aragusteroketal A Type: Gorgostane and other cyclopropacholestane steroids. C31H52O5 Amorph. solid, [α]D25 = +25.3° (c = 0.12, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Cytotoxic (KB, IC50 = 0.004 μg/mL). Ref: M. Kobayashi, et al, CPB, 1996, 44, 1840 OH OH

O H

H O O

1089 Aragusteroketal C Type: Gorgostane and other cyclopropacholestane steroids. C31H53ClO5 Amorph. solid, [α]D25 = +8° (c = 1.5, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Cytotoxic (KB, IC50 = 0.004 μg/mL). Ref: M. Kobayashi, et al, CPB, 1996, 44, 1840 Cl

OH OH

OH H H O O

1090 Aragusterol A Aragusterol Type: Gorgostane and other cyclopropacholestane steroids. C29H46O4 Needles, mp 157–158 °C, [α]D = +37.6° (c = 1.06, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Antineoplastic (P388 in vivo, 6.25 mg/kg, T/C = 172%, L1210 in vivo, 1.6 mg/kg, T/C = 220%); cytotoxic (KB, IC50 = 0.042 μg/mL; HeLa-S3, IC50 = 0.16 μg/mL; P388, IC50 = 0.022 μg/mL; LoVo, IC50 = 0.0079 μg/mL; cell proliferation inhibitor). Ref: K. Iguchi, et al, Tet. Lett., 1993, 34, 6277

432

2 Steroids

OH OH O H H

O H

1091 Aragusterol B Type: Gorgostane and other cyclopropacholestane steroids. C29H48O3 Cryst., (EtOAc/ hexane), mp 194–195 °C, [α]D = +4.0° (c = 1.56, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Cytotoxic (KB, IC50 = 3.3 μg/mL). Ref: H. Shimura, et al, Experientia, 1994, 50, 134│K. Iguchi, et al, JOC, 1994, 59, 7499 OH OH H H

O

1092 Aragusterol C Type: Gorgostane and other cyclopropacholestane steroids. C29H47ClO4 Cryst., mp 204–205 °C, [α]D = +20.1° (c = 0.35, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Cytotoxic (KB, IC50 = 0.041 μg/mL); antineoplastic (in vivo, L1210, 1.6 mg/kg, T/C = 257%). Ref: H. Shimura, et al, Experientia, 1994, 50, 134│K. Iguchi, et al, JOC, 1994, 59, 7499 OH

Cl OH OH

H H

O

1093 Aragusterol E Type: Gorgostane and other cyclopropacholestane steroids. C29H46O3 Glassy solid, [α]D = +12.1° (c = 0.24, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm:

2.12 Gorgostane and Other Cyclopropacholestane Steroids

433

Cytotoxic (KB, IC50 = 8.05 μg/mL, cell proliferation inhibitor). Ref: H. Miyaoka, et al, Tetrahedron, 1997, 53, 5403 OH OH H H

O

H

1094 Aragusterol F Type: Gorgostane and other cyclopropacholestane steroids. C29H48O3 Plates, mp 168–170 °C, [α]D = +20.3° (c = 0.79, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Cytotoxic (KB, IC50 = 4.58 μg/mL, cell proliferation inhibitor). Ref: H. Miyaoka, et al, Tetrahedron, 1997, 53, 5403

OH H H

OH

O H

1095 Aragusterol G Type: Gorgostane and other cyclopropacholestane steroids. C29H50O3 Glassy solid, [α]D = +1.6° (c = 0.5, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Cytotoxic (KB, IC50 = 6.61 μg/mL, cell proliferation inhibitor). Ref: H. Miyaoka, et al, Tetrahedron, 1997, 53, 5403

OH H H

HO

H

OH

434

2 Steroids

1096 Aragusterol H Type: Gorgostane and other cyclopropacholestane steroids. C29H50O3 Rods, mp 189–190 °C, [α]D = −1.5° (c = 0.13, CHCl3). Source: Sponge Xestospongia sp. (Okinawa). Pharm: Cytotoxic (KB, IC50 = 6.48 μg/mL, cell proliferation inhibitor). Ref: H. Miyaoka, et al, Tetrahedron, 1997, 53, 5403

OH H H

OH

HO H

1097 Aragusterol I Type: Gorgostane and other cyclopropacholestane steroids. C29H50O3 Source: Sponge Xestospongia testudinaria (Truong Sa Archipelago, Khanh Hoa, Vietnam). Pharm: Antifoulant (growth inhibition of bacteria Pseudoalteromonas sp. and Polaribacter sp., potent). Ref: X. C. Nguyen, et al, JNP, 2013, 76, 1313 OH OH H H H

H

HO H

1098 (3β,5α,8α)-5,8-epi-Dioxy-33-norgorgost-6-en-3-ol (22R,23R,24R)-5α,8α-Epidioxy-22,23-methylene-24-methylcholest-6-en-3β-ol Type: Gorgostane and other cyclopropacholestane steroids. C29H46O3 Amorph. powder, mp 159–160 °C, [α]D26 = +35° (c = 0.1, CHCl3). Source: Sponge Ircinia campana, soft corals Sinularia aramensis, Sinularia flexibilis, Sinularia sp. (Taiwan waters) and Lobophytum sarcophytoides. Pharm: Cytotoxic (P388, ED50 = 0.4 μg/mL; KB, ED50 = 2.1 μg/mL; A549, ED50 = 2.7 μg/mL; HT29, ED50 = 1.4 μg/mL); clastogenic. Ref: C. Subrahmanyan, et al, Ind. J. Chem., Sect. B, 1995, 34, 1114│J.H. Sheu, et al, JNP, 2000, 63, 149│C. Gonzalez, et al, Acta Farm. Bonaerense, 2005, 25, 75│S. Yu, et al, Steroids, 2006, 71, 955│Y. Lu, et al, Tetrahedron, 2010, 66, 7129

2.12 Gorgostane and Other Cyclopropacholestane Steroids

435

H

H

HO

H

O

O

1099 5α,6α-Epoxy-petrosterol Type: Gorgostane and other cyclopropacholestane steroids. C29H48O2 Solid, [α]D20 = −1.9° (c = 0.07, CHCl3). Source: Sponge Ianthella sp. (Namyet I., Vietnam). Pharm: Cytotoxic (HL60, IC50 = 21.3 μmol/L, control Mitoxantrone, IC50 = 6.3 μmol/L, inhibits growth of HL60 cells by induction of apoptosis; A549, IC50 = 9.8 μmol/L, Mitoxantrone, IC50 = 8.0 μmol/L; HT29, IC50 = 69.9 μmol/L, Mitoxantrone, IC50 = 8.7 μmol/L; MCF7, IC50 = 19.4 μmol/L, Mitoxantrone, IC50 = 7.1 μmol/L; SK-OV-3, IC50 = 22.6 μmol/L, Mitoxantrone, IC50 = 9.8 μmol/L; U937, IC50 = 1 9.9 μmol/L, Mitoxantrone, IC50 = 6.2 μmol/L). Ref: N. H. Tung, et al, BoMCL, 2009, 19, 4584

H H H HO

H

O

1100 5,6-Epoxy-1,3,11-trihydroxy-9,11-secogorgostan-9-one Type: Gorgostane and other cyclopropacholestane steroids. C30H50O5 Gum. Source: Gorgonian Pseudoptero gorgiaamericana (Caribbean Sea). Pharm: Cytotoxic (MTT assay, LNCaP, IC50 = 15.49 μg/mL, lung carcinoma cell, IC50 = 11.0 μg/mL). Ref: S. Naz, et al, Tet. Lett., 2000, 41, 6035 H

HO

H OH

HO

O

O

H

436

2 Steroids

1101 Hirsutosterol C Type: Gorgostane and other cyclopropacholestane steroids. C31H50O5 White power, [α]D25 = +33° (c = 0.11, CHCl3). Source: Soft coral Cladiella hirsuta (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 = 30.1 μmol/L, control Doxorubicin, IC50 = 0.4 μmol/L; HepG3B, IC50 = 13.9 μmol/L, Doxorubicin, IC50 = 1.3 μmol/L; Ca9-22, IC50 = 11.6 μmol/L, Doxorubicin, IC50 = 0.2 μmol/L; A549, IC50 = 31.3 μmol/L, Doxorubicin, IC50 = 2.6 μmol/L; MCF7, IC50 = 39.4 μmol/L, Doxorubicin, IC50 = 2.9 μmol/L; MDA-MB-231, IC50 = 30.1 μmol/L, Doxorubicin, IC50 = 2.0 μmol/L). Ref: B. -W. Chen, et al, Org. Biomol. Chem., 2011, 9, 3272

HO H O O

H O

H OH

1102 7β-Hydroxypetrosterol Type: Gorgostane and other cyclopropacholestane steroids. C29H48O2 Source: Sponge Xestospongia testudinaria (Truong Sa Archipelago, Khanh Hoa, Vietnam). Pharm: Antifoulant (growth inhibition of bacteria Pseudoalteromonas sp. and Polaribacter sp., potent). Ref: X. C. Nguyen, et al, JNP, 2013, 76, 1313

H H H HO

H OH

1103 Ibisterol sulfate Ibisterol tri-O-sulfate Type: Gorgostane and other cyclopropacholestane steroids. C31H49O12S3 Source: Sponge Topsentia sp. (deep water). Pharm: Anti-HIV-1 (NCI primary screen, cytoprotective). Ref: T. C. McKee, et al, Tet. Lett., 1993, 34, 389

2.12 Gorgostane and Other Cyclopropacholestane Steroids

OH O

S

437

H O

H

O

O H O

S OH

O

O O

S

O

OH

1104 21-O-Octadecanoyl-xestokerol A Type: Gorgostane and other cyclopropacholestane steroids. C47H82O6 Source: Sponge Xestospongia testudinaria (Truong Sa Archipelago, Khanh Hoa, Vietnam). Pharm: Antifoulant (growth inhibition of bacteria Pseudoalteromonas sp. and Polaribacter sp., potent). Ref: X. C. Nguyen, et al, JNP, 2013, 76, 1313 O O

OH OH

OH H H H O

H

H

1105 Petrosterol Type: Gorgostane and other cyclopropacholestane steroids. C29H48O Cryst., mp 123–125 °C, mp 158–160 °C. Source: Sponges Ianthella sp. (Namyet I., Vietnam) and Petrosia ficiformis. Pharm: Cytotoxic (HL60, IC50 = 21.5 μmol/L, Mitoxantrone, IC50 = 6.3 μmol/L, inhibits growth of HL60 cells by induction of apoptosis; A549, IC50 = 11.5 μmol/L, control Mitoxantrone, IC50 = 8.0 μmol/L; HT29, IC50 = 46.5 μmol/L, Mitoxantrone, IC50 = 8.7 μmol/L; MCF7, IC50 = 16.4 μmol/L, Mitoxantrone, IC50 = 7.1 μmol/L; SK-OV-3, IC50 = 19.8 μmol/L, Mitoxantrone, IC50 = 9.8 μmol/L; U937, IC50 = 18.7 μmol/L, Mitoxantrone, IC50 = 6.2 μmol/L). Ref: C. A. Mattia, et al, Tet. Lett., 1978, 3953│D. Sica, et al, Tet. Lett., 1978, 19, 837│N. H. Tung, et al, BoMCL, 2009, 19, 4584

438

2 Steroids

H H H

H

HO

1106 Petrosterol-3,6-dione Type: Gorgostane and other cyclopropacholestane steroids. C29H44O2 Amorph. powder, [α]D20 = −2.8° (c = 0.06, CHCl3). Source: Sponge Ianthella sp. (Namyet I., Vietnam). Pharm: Cytotoxic (HL60, IC50 = 19.9 μmol/L, Mitoxantrone, IC50 = 6.3 μmol/L, inhibits growth of HL60 cells by induction of apoptosis; A549, IC50 = 8.4 μmol/L, control Mitoxantrone, IC50 = 8.0 μmol/L; HT29, IC50 = 48.2 μmol/L, Mitoxantrone, IC50 = 8.7 μmol/L; MCF7, IC50 = 17.8 μmol/L, Mitoxantrone, IC50 = 7.1 μmol/L; SK-OV-3, IC50 = 16.2 μmol/L, Mitoxantrone, IC50 = 9.8 μmol/L; U937, IC50 = 22.1 μmol/L, Mitoxantrone, IC50 = 6.2 μmol/L). Ref: N. H. Tung, et al, BoMCL, 2009, 19, 4584

H H H

H

O O

1107 Phrygiasterol (3β,5α,6α,8β,15α,16β,24R,25R)-24,26-Cyclocholestane-3,6,8,15,16,27-hexol Type: Gorgostane and other cyclopropacholestane steroids. C27H46O6 Amorph. solid, [α]D25 = +33.2° (c = 0.25, MeOH). Source: Starfish Hippasteria phrygiana (psychrophilic, cold water, Sea of Okhotsk). Pharm: Cytotoxic (Ehrlich carcinoma cells, IC50 = 50 μg/mL). Ref: E. V. Levina, et al, JNP, 2005, 68, 1541│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)

2.12 Gorgostane and Other Cyclopropacholestane Steroids

439

H H OH

OH

OH

OH HO OH

1108 Stoloniferone D 5,6-Epoxy-11-hydroxy-33-norgorgost-2-en-1-one Type: Gorgostane and other cyclopropacholestane steroids. C29H44O3 Cryst. (MeCN), mp 142 °C, [α]D = +31° (CHCl3). Source: Stolonifer Clavularia viridis (Okinawa). Pharm: Cytotoxic (P388); antiinflammatory. Ref: M. Kobayashi, et al, Tet. Lett., 1984, 25, 5925

H

HO O

H H

H

O

1109 3β,7β,11-Trihydroxy-5α,6α-epoxy-9,11-secogorgostan-9-one Type: Gorgostane and other cyclopropacholestane steroids. C30H50O5 Oil, [α]D = +33.3° (c = 0.1, CHCl3). Source: Gorgonian Lophogorgia sp. Pharm: Cytotoxic (A2780, IC50 = 6.3 μmol/L, K562, IC50 = 7.1 μmol/L). Ref: L. A. Morris, et al, JNP, 1998, 61, 538 HO H O

H H

HO

O

OH

1110 (3β,24ξ)-3,11,24-Trihydroxy-9,11-secogorgost-5-en-9-one Type: Gorgostane and other cyclopropacholestane steroids. C30H50O4 Powder, [α]D = +1.5° (c = 1.2, MeOH). Source: Gorgonian Pseudopterogorgia sp. Pharm: PKCs inhibitor (PKC α, βI, βII, γ, δ, ε, η and ξ, IC50 = 12–50 μmol/L); cytotoxic (3–13 μmol/L with tritiated thymidine (3H-T), MCF7 proliferation inhibitor). Ref: H. He, et al, Tetrahedron, 1995, 51, 51

440

2 Steroids

OH

HO H O

H H

HO

1111 Weinbersteroldisulfate A Type: Gorgostane and other cyclopropacholestane steroids. C30H52O10S2 Cryst. (MeOH aq/CHCl3), mp 182 °C, [α]D = +20° (c = 1.75, MeOH). Source: Sponge Petrosia weinbergi. Pharm: Antiviral. Ref: H. H. Sun, et al, Tetrahedron, 1991, 47, 1185│J. L. Giner, et al, Steroids, 1999, 64, 820

HO 18

O

S

O O O

S

20

H

OH H

O

OH

O OH

1112 Yonarasterol C 5,6,11-Trihydroxy-33-norgorgost-2-en-1-one Type: Gorgostane and other cyclopropacholestane steroids. C31H48O5 Amorph. solid, [α]D25 = +10.4° (c = 0.09, CHCl3). Source: Stolonifer Clavularia viridis (Okinawa). Pharm: Cytotoxic (DLDH, IC50 = 50 μg/mL; Molt4, IC50 = 10 μg/mL). Ref: M. Iwashima, et al, Steroids, 2000, 65, 130; 2001, 66, 25

22R

HO O

H H

OH O O

23R

2.13 Seco-steroids

441

2.13 Seco-steroids 1113 Astrogorgiadiol Type: 9,10-Secocholestane steroids. C27H44O2 Solid, [α]D = −16.4° (c = 0.058, CHCl3). Source: Gorgonians Astrogorgia sp. and Muricella sp. (Korea waters). Pharm: Cytotoxic (K562, IC50 = 10.7 μg/mL); PLA2 inhibitor; cell division inhibitor (fertilised eggs of sea star Asterina pectinifera). Ref: N. Fusetani, et al, Tet. Lett., 1989, 30, 7079│Y. Seo, et al, JNP, 1998, 61, 1441│G. Della Sala, et al, Tet. Lett., 1998, 39, 4741│D. F. Taber, et al, JOC, 2001, 66, 944 HO

22

H H

HO

1114 Calicoferol A Type: 9,10-Secocholestane steroids. C27H40O2 Solid, [α]D15 = +4.2° (c = 0.24, CHCl3). Source: Gorgonian Calicogorgia sp. Pharm: Toxic (brine shrimp). Ref: M. Ochi, et al, Chem. Lett., 1991, 427 O H H H

HO

1115 Calicoferol B Type: 9,10-Secocholestane steroids. C27H44O3 Oil, [α]D21 = −16.2° (c = 0.09, CHCl3). Source: Gorgonian Calicogorgia sp. Pharm: Toxic (brine shrimp). Ref: M. Ochi, et al, Chem. Lett., 1991, 427 HO H H HO

H OH

1116 Calicoferol G 9,10-Secocholesta-1,3,5(10),24-tetraene-3,9-diol Type: 9,10-Secocholestane steroids. C27H42O2 Oil, [α]D25 = −7.5° (c = 0.1, CHCl3). Source: Gorgonian Muricella sp. Pharm: Cytotoxic (K562, LD50 = 3.2 μg/mL). Ref: Y. Seo, et al, JNP, 1995, 58, 129; 1998, 61, 1441

442

2 Steroids

HO H H

H

HO

1117 Calicoferol H Type: 9,10-Secocholestane steroids. C26H40O2 Oil, [α]D25 = −6.6° (c = 0.1, CHCl3). Source: Gorgonian Muricella sp. Pharm: Cytotoxic (K562, LD50 = 2.1 μg/mL). Ref: Y. Seo, et al, JNP, 1998, 61, 1441 HO H H

HO

1118 Calicoferol I 3,16-Dihydroxy-9,10-secocholesta-1,3,5(10)-trien-9-one Type: 9,10-Secocholestane steroids. C27H42O3 Oil, [α]D25 = +18.4° (c = 0.1, CHCl3). Source: Gorgonian Muricella sp. Pharm: Cytotoxic (K562, LD50 = 10.7 μg/mL). Ref: Y. Seo, et al, JNP, 1995, 58, 129; 1998, 61, 1441 O H H H

HO

OH

1119 Calicoferol D Type: 9,10-Secoergostane steroids. C28H42O2 Cryst. (Me2CO/hexane), mp 76–79 °C, [α]D25 = +13.5° (c = 0.4, CHCl3). Source: Gorgonian Muricella sp. (Korea waters). Pharm: Antiviral (HSV-1, EC50 = 1.2 μg/mL; HSV-2, EC50 = 1.2 μg/mL; control Polioviral, EC50 = 0.4 μg/mL); lethality (brine shrimp). Ref: Y. Seo, et al, JNP, 1995, 58, 1291; 1998, 61, 1441 O H H HO

H

2.13 Seco-steroids

443

1120 Calicoferol F 9,10-Secoergosta-1,3,5(10),22-tetraene-3,9-diol Type: 9,10-Secoergostane steroids. C28H44O6 Oil, [α]D25 = +13.7° (c = 0.1, CHCl3). Source: Gorgonian Muricella sp. (Korea waters). Pharm: PLA2 inhibitor; cytotoxic (K562, IC50 = 12.1 μg/mL). Ref: Y. Seo, et al, JNP, 1995, 58, 1291; 1998, 61, 1441 HO H H H

HO

1121 (22E)-11-Acetoxy-3β,6α-dihydroxy-9,11-seco-5α-cholesta-7,22-dien-9-one 11-Acetyl-3,6,11-trihydroxy-9,11-secocholesta-7,22-dien-9-one Type: 9,11-Seco-steroids. C29H46O5 Oil. Source: Soft coral Gersemia fruticosa (Arctic Ocean), gorgonian Eunicella cavolini (Lichadonissia I., Greece). Pharm: Cytotoxic (K562, IC50 = 21 μmol/L, cell growth inhibitor). Ref: R. Koljak, et al, Tetrahedron, 1998, 54, 179│E. Ioannou, et al, BoMC, 2009, 17, 4537 O O

H O

H HO

H

OH

1122 (22E)-11-Acetoxy-3β,6α-dihydroxy-24-nor-9,11-seco-5α-cholesta7,22-dien-9-one Type: 9,11-Seco-steroids. C28H44O5 Oil, [α]D22 = +23° (c = 0.17, MeOH). Source: Soft coral Gersemia fruticosa (Arctic, cold water, Northern Russia), gorgonian Eunicella cavolini (Lichadonissia I., Greece). Pharm: Cytotoxic (MTT assay, 10 μmol/L: LNCaP cells in MEM+ 10% FBS, growth inhibition InRt = (76 ± 4)%, IC50 = (7.0 ± 0.6)μmol/ L; MCF7 cells in MEM+ 10% FBS, growth inhibition InRt = (34 ± 5)%, IC50 = (7.6 ± 0.4)μmol/L; MCF7 cells in MEM+ 5% DCC-FBS+ 1 nM 17β-Estradiol, growth inhibition InRt = (86 ± 9)%, IC50 = (7.4 ± 0.2)μmol/L); cytotoxic (K562, IC50 = 29 μmol/L, cell growth inhibitor); cytotoxic (K562, IC50 = 3 μg/mL; EAC, IC50 = 1 μg/mL). Ref: R. Koljak, et al, Tet. Lett., 1993, 34, 1985│A. Lopp, et al, Steroids, 1994, 59, 274│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev)│E. Ioannou, et al, BoMC, 2009, 17, 4537

444

2 Steroids

O O

H O

H HO

H

OH

1123 3-O-Deacetyl-22,23-dihydro-24,28-didehydro-luffasterol B Type: 9,11-Seco-steroids. C28H42O4 Amorph. solid, [α]D25 = −29.0° (c = 0.1, 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

O H O

H HO

O

1124 3-O-Deacetylluffasterol B Type: 9,11-Seco-steroids. C28H42O4 Amorph. solid, [α]D25 = −21.4° (c = 0.1, 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

O H O

H HO

O

1125 (3β,5α,6α)-3,6-Dihydroxy-11-acetoxy-9,11-secocholest-7-en-9-one Type: 9,11-Seco-steroids. C29H48O5 Oil, [α]D20 = +7.5° (c = 0.03, CHCl3). Source: Gorgonian Eunicella cavolini (Lichadonissia I., Greece). Pharm: Cytotoxic (hmn prostate and breast adenocarcinoma cell lines, moderate). Ref: E. Ioannou, et al, BoMC, 2009, 17, 4537

2.13 Seco-steroids

445

O O

H O

H HO

H

OH

1126 (3β,5α,6α,22Z,24ξ)-3,6-Dihydroxy-11-acetoxy-9,11-secoergosta-7,22-dien-9-one Type: 9,11-Seco-steroids. C30H48O5 [α]D20 = +18° (c = 0.13, CHCl3). Source: Gorgonian Eunicella cavolini (Lichadonissia I., Greece). Pharm: Cytotoxic (MTT assay, 10 μmol/L: LNCaP cells in MEM+ 10% FBS, growth inhibition InRt = (45 ± 12)%, IC50 = (6.7 ± 0.8) μmol/L; MCF7 cells in MEM+ 10% FBS, growth inhibition InRt = (27 ± 3)%; MCF7 cells in MEM+ 5% DCC-FBS+ 1 nM 17β-Estradiol, growth inhibition InRt = (62 ± 12)%, IC50 = (6.0 ± 0.4)μmol/L). Ref: E. Ioannou, et al, BoMC, 2009, 17, 4537

O H

O O

H HO H

OH

1127 (3β,5α,6α)-3,6-Dihydroxy-11-acetoxy-9,11-secoergosta-7,24(28)-dien-9-one Type: 9,11-Seco-steroids. C30H48O5 Oil, [α]D20 = +22° (c = 0.1, CHCl3). Source: Gorgonian Eunicella cavolini (Lichadonissia I., Greece). Pharm: Cytotoxic (MTT assay, 10 μmol/L: LNCaP cells in MEM+ 10% FBS, growth inhibition InRt > 10%; MCF7 cells in MEM+ 10% FBS, growth inhibition InRt ≤ 10%; MCF7 cells in MEM+ 5% DCC-FBS+ 1 nM 17β-Estradiol, growth inhibition InRt = (50 ± 5)%, IC50 = (3.8 ± 0.7)μmol/L). Ref: E. Ioannou, et al, BoMC, 2009, 17, 4537

O O

H O

H HO

H OH

446

2 Steroids

1128 (3β,4α,5α,22E,24R)-3,11-Dihydroxy-4,23-dimethyl-9,11-secoergost-22-en-9-one Type: 9,11-Seco-steroids. C30H52O3 Powder, [α]D = −11.5° (c = 1.7, MeOH). Source: Gorgonian Pseudopterogorgia sp. Pharm: PKCs inhibitor (PKC α, βI, βII, γ, δ, ε, η and ξ, IC50 = 12–50 μmol/L); cytotoxic (3–13 μmol/L with tritiated thymidine (3H-T), MCF7 proliferation inhibitor). Ref: H. He, et al, Tetrahedron, 1995, 51, 51

HO H O H H HO

H

1129 Hirsutosterol A Type: 9,11-Seco-steroids. C30H50O5 White power, [α]D25 = +26° (c = 5.78, CHCl3). Source: Soft coral Cladiella hirsuta (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 = 16.9 μmol/L, control Doxorubicin, IC50 = 0.4 μmol/L; HepG3B, IC50 = 9.4 μmol/L, Doxorubicin, IC50 = 1.3 μmol/L; Ca9-22, IC50 = 8.2 μmol/L, Doxorubicin, IC50 = 0.2 μmol/L; A549, IC50 = 18.4 μmol/L, Doxorubicin, IC50 = 2.6 μmol/L; MCF7, IC50 = 17.8 μmol/L, Doxorubicin, IC50 = 2.9 μmol/L; MDA-MB-231, IC50 = 16.1 μmol/L, Doxorubicin, IC50 = 2.0 μmol/L). Ref: B. -W. Chen, et al, Org. Biomol. Chem., 2011, 9, 3272

HO H O O

H O

H OH

1130 Hirsutosterol B Type: 9,11-Seco-steroids. C30H48O5 White power, [α]D25 = +32° (c = 1.56, CHCl3). Source: Soft coral Cladiella hirsuta (Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 > 50 μmol/L, control Doxorubicin, IC50 = 0.4 μmol/L; HepG3B, IC50 = 8.6 μmol/L, Doxorubicin, IC50 = 1.3 μmol/L; Ca9-22, IC50 = 16.0 μmol/L, Doxorubicin, IC50 = 0.2 μmol/L; A549, IC50 > 50 μmol/L, Doxorubicin, IC50 = 2.6 μmol/L; MCF7, IC50 > 50 μmol/L, Doxorubicin, IC50 = 2.9 μmol/L; MDA-MB-231, IC50 > 50 μmol/L, Doxorubicin, IC50 = 2.0 μmol/L). Ref: B. -W. Chen, et al, Org. Biomol. Chem., 2011, 9, 3272

2.14 Miscellaneous Steroids

447

HO H O O

H O

H

OH

1131 3β-Hydroxy-5α,6α-epoxy-9-oxo-9,11-secogorgostan-11-ol Type: 9,11-Seco-steroids. C30H50O4 Source: Gorgonian Pseudoptero gorgiaamericana (Caribbean Sea). Pharm: Cytotoxic (MTT assay, LNCaP, IC50 = 18.43 μg/mL, lung carcinoma cell, IC50 = 12.0 μg/mL). Ref: S. Naz, et al, Tet. Lett., 2000, 41, 6035 H HO H O H H HO O

2.14 Miscellaneous Steroids 1132 Cinanthrenol A Type: Miscellaneous steroids. C20H18O2 Source: Sponge Cinachyrella sp. (collected by dredging, depth of 160m, Oshima-Shinsone, Japan). Pharm: Cytotoxic (various HTCLs, moderate); estrogen-receptor binder (potent, displacing estradiol in competitive manner with IC50 = 10 nmol/L, altering estrogen responsive gene expression). Ref: K. Machida, et al, Org. Lett., 2014, 16, 1539

HO

OH

1133 Hipposterol G Type: Miscellaneous steroids. C35H56O9 White amorph. powder; [α]D25 = +5° (c = 0.1, CHCl3). Source: Gorgonian Isis hippuris (Orchid I., Taiwan). Pharm: Cytotoxic (P388 and HT29, inactive; HEL, IC50 > 50 μg/mL). Ref: W. -H. Chen, et al, Mar. Drugs, 2011, 9, 1829

448

2 Steroids

O O

O O

O H

OH

O

H

H HO

O

H

1134 Hipposterone M Type: Miscellaneous steroids. C33H52O8 White amorph. powder; [α]D25 = −8° (c = 0.1, CHCl3). Source: Gorgonian Isis hippuris (Orchid I., Taiwan). Pharm: Cytotoxic (P388 and HT29, inactive; HEL, IC50 > 50 μg/mL). Ref: W. -H. Chen, et al, Mar. Drugs, 2011, 9, 1829 O O HO O

O H H

OH

O

H

O H

1135 Hipposterone N Type: Miscellaneous steroids. C31H50O7 White amorph. powder; [α]D25 = −11° (c = 0.1, CHCl3). Source: Gorgonian Isis hippuris (Orchid I., Taiwan). Pharm: Antiviral (HCMV, EC50 = 6.0 μg/mL, mild); cytotoxic (P388 and HT29, inactive; HEL, IC50 > 50 μg/mL). Ref: W. -H. Chen, et al, Mar. Drugs, 2011, 9, 1829 O O HO OH

O H H O H

OH H

2.14 Miscellaneous Steroids

449

1136 Hipposterone O Type: Miscellaneous steroids. C35H54O10 White amorph. powder; [α]D25 = −5° (c = 0.1, CHCl3). Source: Gorgonian Isis hippuris (Orchid I., Taiwan). Pharm: Cytotoxic (P388 and HT29, inactive; HEL, IC50 > 50 μg/mL). Ref: W. -H. Chen, et al, Mar. Drugs, 2011, 9, 1829 O

O

O

O

O

O

OH

O

OH

H H

H

O H

1137 Hippuristeroketal A Type: Miscellaneous steroids. C35H58O9 White amorph. powder; [α]D25 = +21° (c = 0.1, CHCl3). Source: Gorgonian Isis hippuris (Orchid I., Taiwan). Pharm: Cytotoxic (P388 and HT29, inactive; HEL, IC50 > 50 μg/mL). Ref: W. -H. Chen, et al, Mar. Drugs, 2011, 9, 1829 O O

O O

OH

O H O O

H

OH H

H

1138 Ketosteroid New Type: Miscellaneous steroids. C30H48O2 Source: Green alga Tydemania expeditionis (Yellow Sea, China). Pharm: Cytotoxic (prostate cancer cells, modest). Ref: J. -L. Zhang, et al, Fitoterapia, 2012, 83, 973

450

2 Steroids

H H H O

H

H

O

1139 Lobophytosterol‡ Type: Miscellaneous steroids. C30H52O3 White amorph. powder, [α]D25 = +9.74° (c = 1.00, CHCl3). Source: Soft coral Lobophytum laevigatum (KhanhHoa province, Vietnam). Pharm: Cytotoxic (A549, IC50 = (4.5 ± 0.5)μmol/L, control Mitoxantrone, IC50 = (7.8 ± 0.4)μmol/L; HCT116, IC50 = (3.2 ± 0.9)μmol/L, Mitoxantrone, IC50 = (7.2 ± 0.3)μmol/L; HL60, IC50 = (5.6 ± 0.4)μmol/L, Mitoxantrone, IC50 = (8.2 ± 0.9)μmol/L); inducer of apoptosis (A549, HCT116 and HL60). Ref: T. H. Quang, et al, BoMCL, 2011, 21, 2845 OH

O H H

H

HO H

1140 Malaitasterol A Type: Miscellaneous steroids. C30H48O4 Source: Lithistid sponge Theonella swinhoei (depth of 22m, Malaita I., Solomon Is.). Pharm: Potent inducer of pregnane X receptor (PXR) transactivation (10 μmol/L with no effect on farnesoid X receptor (FXR), Its PXR activity was confirmed by an increase in gene expression of downstream PXR targets as well as in molecular docking studies). Ref: S. De Marino, et al, Org. Biomol. Chem., 2011, 9, 4856│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2643 (rev)

HO

H

O O

HO

H

2.14 Miscellaneous Steroids

451

1141 Shishicrellastatin A Type: Miscellaneous steroids. C56H86O16S3 Source: Sponge Crella spinulata (Shi-shi I., Kagoshima, Japan). Pharm: Cathepsin B inhibitor. Ref: S. Murayama, et al, BoMC, 2011, 19, 6594

O

O

H O

H

HO S O O O HO S O O

H O H HO

O H O S OH O

1142 Shishicrellastatin B Type: Miscellaneous steroids. C56H84O16S3 Source: Sponge Crella spinulata (Shi-shi I., Kagoshima, Japan). Pharm: Cathepsin B inhibitor. Ref: S. Murayama, et al, BoMC, 2011, 19, 6594

O

O

H O HO

S O

O HO

H

O

S

O

O

H

O HO

H

O O

S

OH O

1143 Swinhoeisterol A Type: Miscellaneous steroids. C29H46O2 Source: Lithistid sponge Theonella. swinhoei (Xisha Is., South China Sea, China). Pharm: Histone acetyltransferase (h)p300 inhibitor (IC50 = 2.9 μmol/L, indicating the steric importance of 9-OH). Ref: J. Gong, et al, Org. Lett., 2014, 16, 2224

452

2 Steroids

H HO H

H O

1144 Swinhoeisterol B Type: Miscellaneous steroids. C29H46O3 Source: Lithistid sponge Theonella. swinhoei (Xisha Is., South China Sea, China). Pharm: Histone acetyltransferase (h)p300 inhibitor (IC50 = 249 μmol/L, indicating the steric importance of 9-OH). Ref: J. Gong, et al, Org. Lett., 2014, 16, 2224

9

H

OH HO H O

Index 1 Compound Name and Synonym Index This index lists in alphabetical order all active compound’s 1,362 entry names including both 1,144 key names and 218 synonym names contained in the bodies of compound entries. A equal sign (=) and compound code number (from 1 to 1,144) follow the name immediately for locating the compound in the “Handbook of Active Marine Natural Products Volume 5” books. 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 (2α,5α,11β,20R,22S,24S)-4(3→2)-Abeo-22,25epoxy-11,20-dihydroxy-24-methylfurostan-3-oic acid = 835. Acalycigorgia inermis sterol A = 642. Acalycigorgia inermis sterol B = 643. Acalycigorgia inermis sterol C = 644. Acanthifolic acid = 213. Acanthifolicin = 213. Acanthifolioside A = 857. Acanthifolioside B = 858. Acanthifolioside C = 645. Acanthifolioside D = 1032. Acanthifolioside E = 1033. Acanthifolioside F = 1034. Acanthosterol sulfate I = 859. Acanthosterol sulfate J = 860. 12β-Acetoxycholest-4-ene-3,24-dione = 646. Acetoxycrenulide = 101. (22E)-11-Acetoxy-3β,6α-dihydroxy-9,11-seco-5αcholesta-7,22-dien-9-one = 1121. (22S)-3α-Acetoxy-11β,18α-dihydroxy-24-methyl18,20β:22,25-diepoxy-5α-furostane = 839. (22E)-11-Acetoxy-3β,6α-dihydroxy-24-nor-9,11seco-5α-cholesta-7,22-dien-9-one = 1122. 3α-Acetoxy-25-hydroxycholest-4-en6-one = 647. 3-(4-O-Acetyl-6-deoxy-β-galactopyranosyloxy)-19norpregna-1,3,5(10),20-tetraene = 635. 3-Acetyl-2-desacetyl-22S-epi-hippurin 1 = 840. 3-Acetyl-2-desacetyl-22R-epi-hippurin-1 = 841. 3-Acetyl-22-epi-hippuristanol = 842. 5-Acetyl-lituarine C = 190. 8-O-Acetylmalyngamide C = 64. 8-O-Acetyl-8-epi-malyngamide C = 65. 6-O-Acetylmalyngamide F = 66. 2-O-Acetylpinnasterol = 648.

https://doi.org/10.1515/9783110653922-003

Acetyltheonellasterol = 1035. 11-Acetyl-3,6,11-trihydroxy-9,11-secocholesta7,22-dien-9-one = 1121. Acodontasteroside D = 1036. Acodontasteroside E = 861. Acodontasteroside F = 1037. Acodontasteroside G = 862. Acodontasteroside H = 863. Acodontasteroside I = 1038. Acuminolide A = 480. Acyl-hemiacetal sterigmatocystin = 258. Adriatoxin = 145. Agosterol A = 649. Agosterol A4 = 864. Agosterol A5 = 865. Agosterol B = 650. Agosterol C = 651. Agosterol C6 = 1039. Agosterol D2 = 652. Aigialomycin A = 332. Aigialomycin D = 333. Aigialomycin E = 334. Akaeolide = 611. Altohyrtin A = 579. Altohyrtin B = 481. Altohyrtin C = 580. AM17 = 137. Amaranzole B = 653. Amaranzole C = 654. Amaranzole D = 655. Amaranzole E = 656. Amaranzole F = 657. Amphidinin A = 20. Amphidinol = 133. Amphidinol 1 = 133. Amphidinol 2 = 134. Amphidinol 5 = 135.

454

Index 1 Compound Name and Synonym Index

Amphidinol 6 = 136. Amphidinol 17 = 137. Amphidinolactone B = 389. Amphidinolide A = 390. Amphidinolide B = 391. Amphidinolide B1 = 391. Amphidinolide B2 = 392. Amphidinolide B3 = 393. Amphidinolide B4 = 394. Amphidinolide B5 = 395. Amphidinolide B6 = 396. Amphidinolide B7 = 397. Amphidinolide C = 398. Amphidinolide C2 = 399. Amphidinolide C3 = 400. Amphidinolide D = 401. Amphidinolide E = 402. Amphidinolide F = 403. Amphidinolide G1 = 404. Amphidinolide G2 = 405. Amphidinolide G3 = 406. Amphidinolide H = 394. Amphidinolide H = 407. Amphidinolide H1 = 407. Amphidinolide H2 = 408. Amphidinolide H3 = 409. Amphidinolide H4 = 410. Amphidinolide H5 = 411. Amphidinolide J = 412. Amphidinolide K = 413. Amphidinolide L = 414. Amphidinolide M = 415. Amphidinolide N = 416. Amphidinolide O = 417. Amphidinolide P = 418. Amphidinolide Q = 419. Amphidinolide R = 420. Amphidinolide S = 421. Amphidinolide T = 422. Amphidinolide T1 = 422. Amphidinolide T2 = 423. Amphidinolide T3 = 424. Amphidinolide T4 = 425. Amphidinolide T5 = 426. Amphidinolide U = 427. Amphidinolide V = 428. Amphidinolide W = 429. Amphidinolide X = 430. Amphidinolide Y = 431.

Amphilactam A = 482. Amphilactam B = 483. Amphilactam C = 484. Amphilactam D = 485. Amphirionin 4 = 21. Amurensoside A = 658. Anastomosacetal A = 659. Anhydrodebromoaplysiatoxin = 243. Anicequol = 866. Ankaraholide A = 468. Ankaraholide B = 469. Annasterol sulfate = 867. A-nor-22-epi-hippurin-2α-carboxylic acid = 835. Anthraquinone = 263. Antibiotic 3D5 = 309. Antibiotic A300 = 121. Antibiotic BK 223B = 486. Antibiotic IB 96212 = 49. Antibiotic JBIR 59 = 270. Antibiotic ML 449 = 116. Antibiotic MT 332 = 32. Antibiotic SS-228Y = 120. Antimycin A19 = 349. Antimycin A20 = 350. Antimycin B2 = 351. Aplasmomycin = 487. Aplasmomycin A = 487. Aplasmomycin B = 488. Aplasmomycin C = 489. Aplyronine A = 432. Aplyronine B = 433. Aplyronine C = 434. Aplyronine C O7-(2-dimethylamino3-methoxypropanoyl) = 432. Aplyronine C O9-(2-dimethylamino3-methoxypropanoyl) = 433. Aplyronine D = 435. Aplyronine E = 436. Aplyronine F = 437. Aplyronine G = 438. Aplyronine H = 439. Aplysiatoxin = 244. 3-[(3-O-β-D-Arabinofuranosylβ-D-glucopyranosyl)oxy]-7-hydroxycholest5-en-19-oic acid = 732. Aragusteroketal A = 1088. Aragusteroketal C = 1089. Aragusterol = 1090. Aragusterol A = 1090.

Index 1 Compound Name and Synonym Index

Aragusterol B = 1091. Aragusterol C = 1092. Aragusterol E = 1093. Aragusterol F = 1094. Aragusterol G = 1095. Aragusterol H = 1096. Aragusterol I = 1097. Archasteroside A = 1040. Archasteroside B = 660. Arenolide = 490. Ascochlorin = 595. Ascotoxin = 497. Aspericin A = 22. Aspericin C = 23. Aspermytin A = 596. asperversin A = 868. Asperxanthone = 259. Asteriidoside A = 661. Asteriidoside C = 662. Asteriidoside E = 663. Asteriidoside F = 664. Asteriidoside I = 665. Asteriidoside L = 869. Astrogorgiadiol = 1113. Astropectenol A = 666. Astropectenol B = 667. Astropectenol C = 668. Astropectenol D = 669. Astrosterioside A = 670. Astrosterioside C = 626. Astrosterioside D = 826. Aureoverticillactam = 2. Aversin = 260. Averufin = 261. Azalomycin F4a 2-ethylpentyl ester = 386. Azalomycin F5a 2-ethylpentyl ester = 387. B Bafilomycin D = 309. Bafilomycin F = 310. Bafilomycin G = 311. Bafilomycin I = 312. Bahamaolide A = 117. Balticolid = 1. Belizeanolic acid = 24. Belizeanolide = 491. Belizentrin = 492. Biemnasterol = 870. Biselyngbyaside = 493.

Biselyngbyaside B = 494. Biselyngbyolide A = 495. Bislongiquinolide = 271. Bisorbibutenolide = 271. Bisorbicillinol = 272. Bistheonellide A = 470. Bistheonellide B = 471. Bisvertinolone = 273. Bisvertinoquinol = 274. Blancasterol = 671. Borophycin = 496. Brefeldin A = 497. Brevetoxin A = 146. Brevetoxin B = 147. Brevetoxin B1 = 148. Brevetoxin B2 = 149. Brevetoxin B3a = 150. Brevetoxin B3b = 151. Brevetoxin B4b = 152. Brevetoxin C = 156. Brevetoxin PbTx5 = 153. Brevetoxin PbTx6 = 154. Brevetoxin PbTx7 = 155. Brevetoxin PbTx8 = 156. Brevisin = 157. Brevisulcenal F = 158. 19-Bromoaplysiatoxin = 245. 17-Bromooscillatoxin A = 246. Bryostatin 1 = 366. Bryostatin 2 = 367. 20-epi-Bryostatin 3 = 368. Bryostatin 3 = 369. Bryostatin 4 = 370. Bryostatin 5 = 371. Bryostatin 6 = 372. Bryostatin 7 = 373. Bryostatin 8 = 374. Bryostatin 9 = 375. Bryostatin 10 = 376. Bryostatin 11 = 377. Bryostatin 12 = 378. Bryostatin 13 = 379. Bryostatin 14 = 380. Bryostatin 15 = 381. Bryostatin 16 = 382. Bryostatin 17 = 383. Bryostatin 18 = 384. BTXB1 = 148. BTXB2 = 149.

455

456

Index 1 Compound Name and Synonym Index

BTXB3A = 150. BTXB3B = 151. C Calcaride A = 498. Calcaride B = 499. Calcaride C = 500. Calcaride E = 501. Calicoferol A = 1114. Calicoferol B = 1115. Calicoferol D = 1119. Calicoferol F = 1120. Calicoferol G = 1116. Calicoferol H = 1117. Calicoferol I = 1118. Callipeltoside A = 502. Callipeltoside B = 503. Callipeltoside C = 504. Candidaspongiolide A = 505. Candidaspongiolide B = 506. Caribbean ciguatoxin 1 = 159. Caribbean ciguatoxin 2 = 160. Caribenolide I = 507. Carijoside A = 672. Caylobolide A = 508. Caylobolide B = 509. C-CTX-1 = 159. C-CTX-2 = 160. Cerevisterol = 871. Chabrosterol = 872. Chalinasterol = 982. Chloctanspirone A = 275. Chloctanspirone B = 276. 2-Chloro-2-deoxyfusarielin B = 599. (65E)-chloro-KmTx1 = 138. (64E)-Chloro-KmTx3 = 139. N-[2-(Chloromethylene)-6-(2,5-dihydro4-methoxy-2-oxo-1H-pyrrol-1-yl)4-methoxy-6-oxo-4-hexenyl]-7-methoxyN-methyl-4-tetradecenamide = 76. Cholesta-5,23E-dien-3β,25-diol = 673. Cholesta-5,25-diene-3β,24ξ-diol = 674. Cholesta-5,24-diene-3-O-sulfate-19-carboxylic acid = 675. (3β,7β,22E)-Cholesta-5,22-diene-3,7,19triol = 676. Cholesta-7,22-diene-3β,5α,6β-triol = 677. (3β,5α,6α,20S)-Cholesta-9(11),24-diene-3,6,20triol 6-O-[β-D-galactopyranosyl-(1→3)-β-D-

arabinopyranosyl-(1→2)-β-Dfucopyranosyl- (1→4)-[6-deoxy-β-Dglucopyranosyl-(1→2)]-β-D-xylopyranosyl(1→3)-6-deoxy-β-D-glucopyranoside] 3-Osulfate = 663. Cholesta-5-ene-3-O-sulfate-19-carboxylic acid = 678. Cholestane-3α,6α-Diacetoxy-22S,25-diol = 679. Cholestane-3,6,8,15,16,25,26-heptol = 680. (3β,4β,5α,6β,8β,15β,24R)-Cholestane3,4,6,8,15,24,25-heptol = 681. (3β,4β,5α,6α,7α,8β,15β,24S)-Cholestane3,4,6,7,8,15,24-heptol 3-(2-O-methyl-β-Dxylopyranoside) 24-[2-O-methyl-β-Dxylopyranosyl-(1→5)-α-Larabinofuranoside] = 785. (3β,4β,5α,6α,7α,8β,15β,24S)-Cholestane3,4,6,7,8,15,24-heptol 3-O-(2,4-di-Omethyl-β-D-xylopyranoside) 24-O-[β-Dxylopyranosyl- (1→5)-α-Larabinofuranoside] = 784. (25S)-5α-Cholestane-3β,5,6β,15α,16β,26-hexaol 26-sulfate = 682. (25S)-5α-Cholestane-3β,5,6β,15α,16β,26-hexaol 16-sulfate = 683. (3β,4β,5α,6β,15α,24S)-Cholestane3,4,6,8,15,24-hexol = 684. (3β,4β,5α,6α,15β,24S)-Cholestane3,4,6,8,15,24-hexol = 685. (3β,5α,6β,7α,15α,16β)-Cholestane3,6,7,15,16,26-hexol = 686. Cholestane-3,6,8,15,16,26-hexol = 687. (3β,5α,6α,7α,15α,24S)-Cholestane3,6,7,8,15,24-hexol 24-O-[4-O-methyl-β-Dxylopyranosyl-(1→2)-3-O-methyl-β-Dxylopyranoside] = 719. (3β,4β,5α,6α,15β,24S)-Cholestane-3,4,6,8,15,24hexol 24-O-[2-O-methyl-β-D-xylopyranosyl(1→5)-α-L-arabinofuranoside] = 786. (25S)-5β-Cholestane-3β,6β,15α,16β, 26-pentol = 688. (25R)-5α-Cholestane-3β,6β,15α,16β, 26-pentol = 689. (24S)-5α-Cholestane-3β,5,6β,15α,24-pentol 15-sulfate = 690. (3β,5α,6β,15β,24S)-Cholestane-3,6,8,15,24pentol 24-O-[2,4-di-O-methyl-β-Dxylopyranosyl-(1→2)-α-Larabinofuranoside] = 759.

Index 1 Compound Name and Synonym Index

(3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24pentol 24-O-[2,4-di-O-methyl-β-Dxylopyranosyl-(1→5)-α-Larabinofuranoside] = 793. (3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24pentol 24-O-[2,3-di-O-methyl-β-Dxylopyranosyl-(1→2)-α-Larabinofuranoside] = 794. (3β,5α,6α,15α,24S)-Cholestane-3,6,8,15,24pentol 24-O-(3-O-Methyl-4-O-sulfo-β-Dxylopyranoside) = 808. (3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24pentol 24-O-[2-O-methyl-β-Dxylopyranosyl-(1→5)-α-Larabinofuranoside] = 791. (3β,5α,6α,15α,24S)-Cholestane-3,6,8,15,24pentol 24-O-[4-O-methyl-β-Dxylopyranosyl-(1→2)-3-O-methyl-β-Dxylopyranoside] = 720. 5α-Cholestane-3β,5,6β,15α,16β-pentol 16sulfate = 691. (3β,5α,6β,15α,24S)-Cholestane-3,5,6,15,24pentol 24-O-β-D-xylopyranoside = 813. (3β,5α,6α,15β,24S)-Cholestane-3,6,8,15,24pentol 24-O-[β-D-xylopyranosyl-(1→5)-α-Larabinofuranoside] = 792. 5β-Cholestane-3α,4α,11β,21-tetraol 3,21disulfate = 692. (3β,5α,6α,15β,24S)-Cholestane-3,6,15,24-tetrol 24-O-β-D-xylopyranoside = 812. (3β,5α,6α,15α,24S)-Cholestane-3,6,15,24-tetrol 24-O-β-D-xylopyranoside 15-Osulfate = 658. (3α,4β,5α)-Cholestane-3,4,21-triol 3,21-di-Osulfate = 693. Cholest-4-ene-3α,6β-diol = 694. 3α-Cholest-5-ene-3,21-diol 3,21-disulfate = 695. Cholest-4-ene-3,24-dione = 696. (3β,4β,5α,6α,7α,8β,15β,24R)-Cholest-22E-ene3,4,6,7,8,15,24-heptol 6-O-sulfate = 697. (3β,4β,5α,6α,8β,15β,22E,24R)-Cholest-22-ene3,4,6,8,15,24-hexol = 698. (3β,5α,6α,15β,16β,22E,25S)-Cholest-22-ene3,6,8,15,16,26-hexol 3,26-di-O-β-Dxylopyranoside = 664. (25R)-Cholest-22-ene-3,6,8,15,16,26hexol = 699. Cholest-22E-ene-3β,6β,8β,15α,24Rpentol = 700.

457

(3β,7β,9α)-Cholest-5-ene-3,7,9,19-tetrol = 701. (3β,5α,6α,16β,20S)-Cholest-9(11)-ene3,6,16,20-tetrol 6-O-[6-deoxy-β-Dgalactopyranosyl-(1→2)-6-deoxy-β-Dglucopyranosyl-(1→4)-[6-deoxy-β-Dglucopyranosyl-(1→2)]-6-deoxy-β-Dglucopyranosyl-(1→3)-6-deoxy-β-Dglucopyranoside] 3-Sulfate = 660. (20R)-Cholest-5-ene-2α,3α,4β,21-tetrol 3,21disulfate = 702. (3β,4β,5α,6α,11α,22R)-Cholest-7-ene-3,4,6triacetoxy-11,22-diol = 649. (3β,7β)-Cholest-5-ene-3,7,19-triol = 703. Cholest-24-ene-(3α,6β,7β)-triol = 704. Cholest-7-ene-3,5,6-triol = 705. (2β,3α)-Cholest-5-ene-2,3,21-triol 3, 21-disulfate = 706. Cholest-5-ene-1,3,21-triol-3,21-disulfate = 707. (3β,5α,6α,23S)-Cholest-9(11)-ene-3,6,23-triol 3,6-disulfate (disodium salt) = 708. (3β,5α)-Cholest-7-en-3-ol = 709. Cholesterol = 710. Chondropsin A = 510. Chondropsin B-32-O-(3-carboxy3-hydroxypropanoyl)-(1→67)-Lactone = 512. Chondropsin C = 511. Chondropsin D = 512. Ciguatoxin 2A1 = 163. Cinachyrolide A = 582. Cinanthrenol A = 1132. Clathsterol = 1041. Clonostachydiol = 60. Cochliomycin A = 321. Colletoketol = 61. Colopsinol A = 7. Colopsinol C = 8. Colopsinol E = 9. Conicasterol B = 873. Conicasterol C = 874. Conicasterol D = 875. Crassarosterol A = 876. Crassarosteroside A = 877. Crassarosteroside B = 878. Crassarosteroside C = 879. Craterellon C = 598. Crellastatin A = 711. Crellastatin B = 712. Crellastatin C = 713.

458

Index 1 Compound Name and Synonym Index

Crellastatin D = 714. Crellastatin E = 715. Crellastatin F = 716. Crellastatin G = 717. Crellastatin H = 718. Crossasteroside A = 719. Crossasteroside B = 720. Crustecdysone = 837. Curvulone A = 335. Curvulone B = 336. Cyanein = 497. Cyanolide A = 3. (3β,5α,6α,8β,15α,16β,24R,25R)-24,26Cyclocholestane-3,6,8,15,16,27hexol = 1107. Cylindrol B = 597. D Dactylolide = 513. Dankasterone A = 880. Dankasterone B = 881. Daporine = 612. Deacetoxystylocheilamide = 89. 5-De-O-acetylaltohyrtin A = 581. 3-O-Deacetyl-22,23-dihydro-24,28-didehydroluffasterol B = 1123. 3-O-Deacetylluffasterol B = 1124. Debromoaplysiatoxin = 247. Decumbenone C = 598. 3B-De-O-digitoxosylkijanimicin = 323. 7-Dehydrobrefeldin A = 514. 24-Dehydrocholesterol = 721. Dehydroconicasterol = 882. 10,11-Dehydrocurvularin = 337. 11ʹ,12ʹ-Dehydroelaiophylin = 313. 9(11)-Dehydroergosterol peroxide = 883. 10,11-Dehydro-13-hydroxycurvularin = 338. Dehydroxychlorofusarielin B = 599. 15-Dehydroxyconicasterol C = 884. 15-Dehydroxyconicasterol D = 885. 11-Dehydroxy-22-epi-hippuristanol = 843. 11-Dehydroxy-22-epi-hippuristanol3-one = 844. 29-Demethylgeodisterol-3-O-sulfate = 886. 15-De-O-methylonnamide = 67. 19-O-DemethylscytophycinC = 515. 13-Demethylspirolide C = 214. 16-Demethyl-swinholide A 7,7′-bis-O-(2,3-di-Omethyl-β-L-lyxopyranoside) = 469.

Dendronesterol B = 722. Dendronesterone A = 723. Denticulatin A = 25. Denticulatin B = 26. 73-Deoxychondropsin A = 516. 2-DeoxycrellastatinA = 712. 2ʹ-DeoxycrellastatinA = 713. 7-Deoxyokadaic acid = 215. 13-Deoxytedanolide = 517. 2-Desacetyl-22S-epi-hippurin 1 = 845. Desulfohaplosamate = 887. 24-Desulfo-24-ketone-26-[(2-amino-2carboxyethyl)lthio]-squalamine = 724. 1-Desulfoyessotoxin = 161. (22S)-2α,3α-Diacetoxy-11β,18α-dihydroxy-24methyl-18,20β:22,25-diepoxy-5αfurostane = 846. 3α,11α-Diacetoxy-25-hydroxycholest-4-en-6one = 725. 3β-O-(3‘,4‘-Di-O-acetyl-β-D-arabinopyranosyl) -25ξ-cholestane-3β,5α,6β,26-tetrol-26acetate = 672. 17,19-Dibromooscillatoxin A = 248. 19,21-Dibromooscillatoxin A = 248. Dictyostatin = 518. Dictyostatin-1 = 518. 13,19-Didemethylspirolide C = 216. 16,16′-Didemethyl-swinholide A 7,7′-bis-O-(2,3di-O-methyl-β-L-lyxopyranoside) = 468. 2,2′-DideoxycrellastatinA = 714. 4,5-Dideoxy-lituarine C = 189. Dideoxymalyngamide C = 86. 2-[3,5-Diethyl-5-(2-ethyl-3-hexen-1-yl)-2(5H)furanylidene]acetic acid methyl ester = 10. 2-[3,5-Diethyl-5-(2-ethylhexyl)-2(5H)furanylidene]acetic acid methyl ester = 11. 10,11-Dihydrobisvertinolone = 277. 2′′,3′′-Dihydrobisvertinolone = 277. Dihydrobrevetoxin B = 162. 9,10-Dihydrocolletodiol = 62. Dihydrodemethylsorbicillin = 278. 2,3-Dihydro-2,3-dihydroxyciguatoxin 3C = 163. 14,15-Dihydrodinophysistoxin 1 = 217. 6,7-Dihydroonnamide A = 68. 6,7-Dihydro-11-oxoonnamide A = 69. 10,11-Dihydro-oxosorbiquinol = 279. Dihydrooxosorbiquinol = 279. Dihydroprorocentrolide = 519. 2ʹ,3ʹ-Dihydrosorbicillin = 280.

Index 1 Compound Name and Synonym Index

Dihydrotrichodermolide = 281. Dihydrotrichodimerol = 282. (3β,5α,25ξ)-3,5-Dihydroxy-26-acetoxycholestan-6-one = 643. (3β,5α,6α)-3,6-Dihydroxy-11-acetoxy-9,11secocholest-7-en-9-one = 1125. (3β,5α,6α,22Z,24ξ)-3,6-Dihydroxy-11-acetoxy9,11-secoergosta-7,22-dien-9-one = 1126. (3β,5α,6α)-3,6-Dihydroxy-11-acetoxy-9,11secoergosta-7,24(28)-dien-9-one = 1127. (20S)-18,20-Dihydroxycholesta-1,4-diene-3,16dione = 726. (5α,22ξ,23ξ)-22,23-Dihydroxycholesta-1,24dien-3-one = 727. (3β,5α,6α)-3,6-Dihydroxycholesta-9(11),24dien-23-one 6-O-[β-D-fucopyranosyl-(1→2)β-D-fucopyranosyl-(1→4)-[β-Dquinovopyranosyl- (1→2)]-β-Dquinovopyranosyl-(1→3)-β-Dglucopyranoside] 3-sulfate = 790. (3β,5α,6α)-3,6-Dihydroxycholesta-9(11),24dien-23-one 3-sulfate = 728. (16S,20S)-16,20-Dihydroxycholestan-3one = 729. 6β,16β-Dihydroxycholest-4-en-3-one = 730. (3β,4α,5α,22E,24R)-3,11-Dihydroxy-4,23-dimethyl9,11-secoergost-22-en-9-one = 1128. 3β,15a-Dihydroxy-(22E,24R)-ergosta-5,8(14),22trien-7- one = 888. 3β,15β-Dihydroxy-(22E,24R)-ergosta-5,8(14),22trien-7-one = 889. 3,6-Dihydroxy-24-nor-9-oxo-9,11-secocholesta7,22-dien-11-al = 731. 3,4-Dihydroxypregna-5,15-diene-20-one-19,2carbolactone = 627. 3α,16β-Dihydroxy-5α-pregna-1,20-diene-3,16diacetate = 628. (3β,5α,6α)-3,6-Dihydroxypregn-9(11)-en-20-one 6-O-(6-deoxy-β-D-glucopyranoside) 3-Osulfate = 629. 3,16-Dihydroxy-9,10-secocholesta-1,3,5(10)trien-9-one = 1118. (3β,5α,14β,24R)-3,16-Dihydroxystigmast-16ene-15,23-dione 3-O-[β-D-Glucopyranosyl(1→2)-β-D-glucuronopyranoside] = 1066. (3β,5α,6α,22E,24ξ)-3,6-Diihydroxy-11-acetoxy-27nor-9,11-secoergosta-7,22-dien-9one = 890. 6,8-Di-O-methylaverufin = 262.

459

(3β,23ξ,25ξ)-23,26-Dimethylergosta-5,24(28)dien-3-ol = 994. 6,8-Di-O-methylnidurufin = 263. Dimorphoside A = 732. Dinophysistoxin 1 = 218. Dinophysistoxin 2 = 219. Dinophysistoxin 4 = 220. Dinophysistoxin 5a = 221. Dinophysistoxin 5b = 222. (3β,7α)-26,27-Dinorcholest-5-en-23-yne-3,7diol = 828. Dinorspiculoic acid = 600. Dinorspiculoic acid A = 600. 5,8-epi-Dioxycholesta-6-en-3-ol = 733. 5α,8α-epi-Dioxyergosta-6,22-dien3β-ol = 891. 5α,8α-epi-Dioxy-24(R)-methylcholesta-6,9 (11),22-trien-3β-ol = 883. (3β,5α,8α)-5,8-epi-Dioxy-33-norgorgost-6-en3-ol = 1098. Diplasterioside A = 734. Diplasterioside B = 892. Discalamide A = 112. Discalamide B = 113. Discodermide = 613. Dolabelide A = 520. Dolabelide B = 521. Dolabelide C = 522. Dolabelide D = 523. Downeyoside A = 893. Downeyoside B = 894. DTX1 = 218. DTX2 = 219. DTX4 = 220. DTX5a = 221. DTX5b = 222. Dysideasterol A = 735. Dysideasterol F = 736. Dysideasterol G = 737. Dysideasterol H = 895. E Ecdysterone = 837. 5α,8α-Epidioxy-23,24(R)-dimethylcholesta-6, 22-dien-3β-ol = 896. (3β,5α,8α,24R)-5,8-Epidioxy-24hydroperoxystigmasta-6,28-dien-3ol = 1042.

460

Index 1 Compound Name and Synonym Index

(3β,5α,8α,24S)-5,8-Epidioxy-24hydroperoxystigmasta-6,28-dien-3ol = 1043. (22R,23R,24R)-5α,8α-Epidioxy-22,23methylene-24-methylcholest-6-en- 3βol = 1098. 5,8-Epidioxy-23-methylergosta-6,9(11),22-trien3-ol = 897. 24ξ,25-Epoxy-12β-acetoxycholest-4-en-3one = 738. 24ξ,25-Epoxy-23ξ-acetoxycholest-4-en-3one = 739. 7α,8α-Epoxy-3β-acetoxy-,5α,6αdihydroxycholest-24-ene = 740. 18,22-Epoxycholesta-1,20(22)-dien3-one = 741. 7,8-Epoxycholestane-3,5,6-triol = 742. 5β,6β-Epoxycholest-24-ene-3β,7β-diol = 743. (17α,20R,21R,24R)-21,24-Epoxy-17,21dihydroxycholesta-1,4-dien-3-one = 659. 4,5-Epoxy-6,11-dihydroxyergost-2-en1-one = 1019. 7,8-Epoxy-26,27-dinorergost-23-ene-3,5, 6-triol = 827. (3β,6α,16β,20R,22S,23S,24R)-16,22Epoxyergost-9(11)-ene-3,6,20,23-tetrol 3-Oβ-D-glucuronopyranoside 6-sulfate = 893. (3β,6α,16β,20R,22S,23S,24S)-16,22Epoxyergost-9(11)-ene-3,6,20,23-tetrol 3-Oβ-D-glucuronopyranoside 6-sulfate = 894. 7,8-Epoxyergost-22-ene-3,5,6-triol = 898. (3β,5α,6α,20R,22R,23S,24S)-22,23Epoxyergost-9(11)-ene-3,6,20-triol 6-O-[βD-fucopyranosyl-(1→2)-6-deoxy-β-Dglucopyranosyl- (1→4)-[6-deoxy-β-Dglucopyranosyl-(1→2)]-6-deoxy-β-Dglucopyranosyl-(1→3)-β-Dglucopyranoside] 3-O-sulfate = 993. (3β,5α,6α,20R,22R,23S,24S)-22,23Epoxyergost-9(11)-ene-3,6,20-triol 6-O-[βD-galactopyranosyl-(1→4)-[β-Dfucopyranosyl-(1→2)]-β-D- glucopyranosyl(1→4)-[6-deoxy-β-D-glucopyranosyl-(1→2)]β-D-xylopyranosyl-(1→3)-6-deoxy-β-Dglucopyranoside] 3-O-sulfate = 990. 24,25(R/S)-Epoxy-6β-hydroxycholest-4-en-3one = 744. (22E,24R)-5α,6α-Epoxy-3β-hydroxyergosta-22ene-7-one = 899.

(20R,22R,23S,24S)-22,23-Epoxy-20-hydroxy-24methyl-6α-O-{β-D-xylopyranosyl-(1→3)-β-Dfucopyranosyl-(1→2)-β-D-quinovopyranosyl(1→4)-[β-D-quinovopyranosyl-(1→2)]-β-Dxylopyranosyl-(1→3)-β-D-quinovopyranosyl} }-5α-cholest-9(11)-en-3β-yl sulfate = 937. 5,6-Epoxy-11-hydroxy-33-norgorgost-2-en1-one = 1108. (20R,22R,23S)-22,23-Epoxy-20-hydroxy-6α-O{β-D-xylopyranosyl-(1→3)-β-Dfucopyranosyl-(1→2)-β-Dquinovopyranosyl-(1→4)-[β-Dquinovopyranosyl-(1→2)]-βdxylopyranosyl-(1→3)-β-Dquinovopyranosyl}}-5α-cholest-9(11)-en3β-yl 3-sulfate = 761. (20R,22R,23S)-22,23-Epoxy-20-hydroxy-6α-O-{βD-xylopyranosyl-(1→3)-β-D-fucopyranosyl(1→2)-β-D-quinovopyranosyl-(1→4)-[β-Dquinovopyranosyl-(1→2)]-β-dxylopyranosyl(1→3)-β-D-quinovopyranosyl}}-24-nor-5αcholest-9(11)-en-3β-yl sulfate = 833. 7,8-Epoxy-24-methylcholest-22-ene-3,5, 6-triol = 898. 22,25-Epoxy-24-methylfurostane-2-acetoxy,3,11,20-tirol = 847. 5α,6α-Epoxy-petrosterol = 1099. Epoxysorbicillinol = 283. (3β,5α,6α,22R,23S,24S)-22,23-Epoxystigmast-9 (11)-ene-3,6,20-triol 6-O-[β-Dfucopyranosyl-(1→2)-6-deoxy-β-Dglucopyranosyl-(1→4)- [6-deoxy-β-Dglucopyranosyl-(1→2)]-6-deoxy-β-Dglucopyranosyl-(1→3)-β-Dglucopyranoside] 3-O-sulfate = 1040. 4,5-Epoxy-2,3,12,22-tetrahydroxy-14methylcholesta-7,9(11)-diene-6, 24-dione = 745. 5,6-Epoxy-1,3,11-trihydroxy-9,11-secogorgostan9-one = 1100. (3β,7β)-Ergosta-5,24(28)-diene-7-acetoxy-3, 19-diol = 973. (3β,23S)-Ergosta-5,24(28)-diene-3, 23-diol = 900. (3β,23R)-Ergosta-5,24(28)-diene-3, 23-diol = 901. (3β,25)-Ergosta-5,24(28)-diene-3, 25-diol = 902. Ergosta-4,24(28)-diene-3β,6β-diol = 903.

Index 1 Compound Name and Synonym Index

3β-Ergosta-5,24(28)-diene-3,19-diol = 959. (22E)-Ergosta-7,22-diene-6α-hexadecanooxyl3β,5α-diol = 904. (22E)-Ergosta-7,22-diene-6β-hexadecanooxyl3β,5α-diol = 905. (22E)-Ergosta-7,22-diene-6α-9Z,12Zoctadecadienooxyl-3β,5α-diol = 906. (22E)-Ergosta-7,22-diene-6β-octadecanooxyl3β,5α-diol = 907. (22E)-Ergosta-7,22-diene-6α-octadecanooxyl3β,5α-diol = 908. (22E)-Ergosta-7,22-diene-6α-9Zoctadecenooxyl-3β,5α-diol = 909. Ergosta-8(14),22-diene-3β,5α,6β, 7α-tetraol = 910. (3β,6α,15β,22E,24R,25S)-Ergosta-8(14),22diene-3,6,15,26-tetrol = 911. (3β,6α,15β,22E,24R,25S)-Ergosta-8(14),22diene-3,6,15,26-tetrol 26-O-[2-O-Methyl-βD-xylopyranosyl-(1→2)-β-Dxylopyranoside] = 863. Ergosta-7,22-diene-3β,5α,6β-triol = 871. (3β,22S)-Ergosta-5,24(28)-diene-3,17, 22-triol = 912. (3β,7β)-Ergosta-5,24(28)-diene-3,7, 19-triol = 972. 24S-Ergostane-3β,5α,6β,7β-tetrol = 913. (3β,5α,6β,24ξ)-Ergostane-3,5,6,25-tetrol 25-acetate = 914. (22E,24R)-Ergosta-4,6,8(14),22-tetraen3-one = 915. Ergosta-7,22,25-triene-3,5,6-triol = 870. (24S)-Ergost-5-ene-3β,7α-diol = 916. (3β,4β,5α,6α,8β,15β,22E,24R,25S)-Ergost22-ene-3,4,6,8,15,26-hexol 26-O-[2-Omethyl-β-D-xylopyranosyl-(1→2)-β-Dxylopyranoside] = 861. (3β,4β,5α,6β,8β,15α,22E,24R,25S)-Ergost-22ene-3,4,6,8,15,26-hexol 3-O-(2,3,4-tri-Omethyl-β-D-xylopyranoside) = 995. (3β,5α,6β)-Ergost-24(28)-ene-3,5,6, 19-tetrol = 971. (1α,3β,5α,6β)-Ergost-24(28)-ene-1,3,5, 6-tetrol = 977. (3β,5α,24S)-Ergost-7-en-3-ol = 918. (3β,5α,24R)-Ergost-7-en-3-ol methoxymethyl ether = 917. γ-Ergostenol = 918. Ergosterol peroxide = 891.

Eryloside A = 746. 24-Ethylcholesta-4,24(28)-diene-3, 6-dione = 1044. (24R)-24-Ethyl-5α-cholestane-3β,5,6β,15α, 29-pentol 29-sulfate = 1045. (24S)-24-Ethyl-7α-hydroperoxycholesta-5, 25-dien-3β-ol = 1046. (24S)-24-Ethyl-5α-hydroperoxycholesta-6, 25-dien-3β-ol = 1047. 24-Ethylidenecholest-4-en-3-one = 1077. (24S)-24-Ethyl-3-oxocholesta-4,25-dien6β-ol = 1048. Euryspongiol A1 = 747. Euryspongiol A2 = 748. F Feigrisolide C = 46. Feigrisolide D = 47. Fibrosterol sulfate B = 749. Fibrosterol sulfate C = 750. Fijianolide A = 524. Fijianolide B = 541. Forbeside E3 = 629. Formosalide A = 4. Formosalide B = 5. Fragilioside A = 751. Fragilioside B = 752. Fucosterol = 1049. Fungisterol = 918. Fusarielin A = 601. Fusarielin B = 602. Fusarielin E = 603. G GA-A = 164. GA-B = 165. GA-C = 166. GA-D = 167. Gambieric acid A = 164. Gambieric acid B = 165. Gambieric acid C = 166. Gambieric acid D = 167. Gambierol = 168. GB-N = 181. Gelliusterol A = 828. Gelliusterol B = 829. Gelliusterol C = 753. Gibberoepoxysterol = 919. Gibberoketosterol = 920.

461

462

Index 1 Compound Name and Synonym Index

Glaciasterol A = 830. Glaciasterol B 3-acetate = 754. 3β-O-[β-D-Glucopyranosyl-(1→2)-β-Dglucopyranosyloxyuronic acid]-16-hydroxy5α,14β-poriferasta-16,24(241)-diene-15,23dione = 1074. Goniodomin A = 525. Goniopectenoside A = 755. Goniopectenoside B = 756. Goniopectenoside C = 757. Gracilioether B = 12. Gracilioether C = 13. Grahamimycin A = 61. Grahamimycin A1 = 63. Grincamycin A = 121. Grincamycin B = 122. Grincamycin C = 123. Grincamycin D = 124. Grincamycin E = 125. Grincamycin F = 126. Gymnasterone A = 921. Gymnasterone B = 922. Gymnasterone C = 923. Gymnasterone D = 924. Gymnocin A = 169. Gymnocin A2 = 170. Gymnocin B = 171. H Halichoblelide A = 314. Halichoblelide B = 315. Halichoblelide C = 316. Halichomycin = 27. Halichondrin B = 172. Halichondrin B-1020 = 173. Halichondrin B-1076 = 174. Halichondrin B-1092 = 175. Halichondrin B-1140 = 176. Halichondrin C = 177. Halicrasterol A = 925. Halicrasterol B = 926. Halicrasterol C = 927. Halicrasterol D = 928. Halistanol sulfate = 929. Halistanol sulfate A = 930. Halistanol sulfate B = 831. Halistanol sulfate C = 758. Halistanol sulfate D = 832. Halistanol sulfate E = 931.

Halistanol sulfate F = 932. Halistanol sulfate G = 933. Halistanol sulfate H = 934. Halistatin 1 = 178. Halistatin 2 = 179. Halistatin 3 = 180. Halityloside F = 759. Haplosamate A = 935. Haplosamate B = 936. Haterumalide B = 526. Haterumalide NA = 527. Haterumalide NB = 528. Haterumalide NC = 529. Haterumalide ND = 530. Haterumalide NE = 531. Hemiacetal sterigmatocystin = 264. Hemibrevetoxin B = 181. Herbarone = 614. Herbasterol = 760. (2β,3β,5β,20R,22R)-2,3,14,20,22,25Hexahydroxycholest-7-en-6-one = 837. Hippasterioside A = 937. Hippasterioside B = 761. Hippasterioside D = 833. Hipposterol G = 1133. Hipposterone M = 1134. Hipposterone N = 1135. Hipposterone O = 1136. Hippurin 1 = 847. 22-epi-Hippurin 1 = 848. Hippuristanol = 849. 22-epi-Hippuristanol = 850. Hippuristeroketal A = 1137. Hippuristerol A = 938. Hippuristerol B = 939. Hippuristerol D = 940. Hippuristerone A = 941. Hippuristerone B = 942. Hippuristerone D = 943. Hirsutosterol A = 1129. Hirsutosterol B = 1130. Hirsutosterol C = 1101. Hirsutosterol D = 762. Hirsutosterol E = 944. Hirsutosterol F = 945. Hirsutosterol G = 763. Homohalichondrin A = 182. Homohalichondrin B = 183. Homohalichondrin C = 184.

Index 1 Compound Name and Synonym Index

Homononactyl homononactoate = 47. 1a-Homoyessotoxin = 203. Hurghadolide A = 472. 25-Hydroperoxycholesta-4,23-diene-3,6-dione = 764. 24ξ-Hydroperoxycholesta-4,25-diene-3,6-dione = 765. 25-Hydroperoxycholesta-5,(23E)-dien-3β-ol = 766. 24ξ-Hydroperoxycholesta-5,25-dien-3β-ol = 767. 24ξ-Hydroperoxy-24-ethylcholesta-4,28(29)diene-3,6-dione = 1050. 24ξ-Hydroperoxy-6β-hydroxycholesta-4,25dien-3-one = 768. 25-Hydroperoxy-6β-hydroxycholesta-4,23-dien3-one = 769. 24ξ-Hydroperoxy-6β-hydroxy- 24-ethylcholesta4,28(29)-dien-3-one = 1051. 7β-Hydroperoxy-24-methylenecholersterol = 946. 24-Hydroperoxy-24-vinylcholesterol = 1052. 10-Hydroxy-18-O-methylbetaenone C = 604. (24R)-Hydroxycholesta-4,22E-dien-3-one = 770. 3β-Hydroxycholesta-5,24-dien-23-one = 771. (20S)-20-Hydroxycholestane-3,16-dione = 772. 16β-Hydroxy-5α-cholestane-3,6-dione = 773. (20S)-20-Hydroxycholest-1-ene-3,16-dione = 774. 3β-Hydroxycholest-5-en-7-one = 775. 3β-Hydroxycholest-5-en-23-yn-7-one = 753. 51-Hydroxyciguatoxin 3C = 185. 51-HydroxyCTX 3C = 185. 11α-Hydroxycurvularin = 339. 11β-Hydroxycurvularin = 340. 42-Hydroxy-3,26-didemethyl-19,44dideoxypalytoxin = 141. (22E)-3β-Hydroxy-5α,6α:14α,15αdiepoxyergosta-22-en-7-one = 947. 3β-Hydroxy-26,27-dinorcholest-5-en-23-yn-7one = 829. 24-Hydroxy-26,27-dinorergosta-4,22E-dien-3one = 834. 22(R)-Hydroxy-3,16-dioxocholest-4-en-18-al = 776. 3β-Hydroxy-5α,6α-epoxy-9-oxo-9,11secogorgostan-11-ol = 1131. 3β-Hydroxy-(22E,24R)-ergosta-5,8,14,22tetraen-7-one = 948.

463

15α-Hydroxy-(22E,24R)-ergosta-3,5,8(14),22tetraen-7-one = 949. 3β-Hydroxy-(22E,24R)-ergosta-5,8,22-trien-7,15dione = 950. 6β-Hydroxy-24-ethylcholesta-4,24(28)-dien-3one = 1053. 22ξ-Hydroxyfurosta-1,4-dien-3-one = 851. 22ξ-Hydroxyfurost-1-en-3-one = 852. 10-Hydroxyhalichondrin B = 178. 2α-Hydroxyhippuristanol = 853. N-[2-Hydroxy-2-(4-hydroxy-3,5,5-trimethyl-6oxo-1-cyclohexen-1-yl)-1-(methoxymethyl) ethyl]-7-methoxy-9-methyl-4hexadecenamide = 81. 3β-Hydroxyl-(22E,24R)-ergosta-5,8(14),22-trien7,15-dione = 951. 3β-Hydroxyl-(22E,24R)-ergosta-5,8,22-trien-7one = 952. 5-Hydroxymethyl-discodermolate = 28. 13-Hydroxy-15-O-methylenigmazole A = 532. 6-Hydroxy-7-O-methylscytophycin E = 533. 24-Hydroxy-3-oxostigmasta-1,25-dien-18-oic acid = 1062. 24-Hydroxy-3-oxostigmasta-4,25-dien-18-oic acid = 1063. 24-Hydroxy-3-oxostigmasta-1,4,6,25-tetraen-18oic acid = 1061. 7β-Hydroxypetrosterol = 1102. 16β-Hydroxy-5α-pregna-1,20-dien-3-one-16acetate = 630. 3β-Hydroxypregn-5-en-20-one = 631. 16-Hydroxy-3β-O-[α-rhamnopyranosyl-(1→4)-βD-glucopyranosyloxyuronic acid]-5α,14βporiferast-16-ene-15,23-dione = 1072. 6-Hydroxyscytophycin B = 534. 7α-Hydroxytheonellasterol = 1054. 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-Dglucopyranosyloxyuronic acid]-5α,14βergosta-8,16,24(241)-triene-15,23-dione = 983. 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-Dglucopyranosyloxyuronic acid]-5α,14βergost-8,16-diene-15,23-dione = 985. 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-Dglucopyranosyloxyuronic acid]-5α,14βporiferasta-7,16-diene-15,23-dione = 1068. 16-Hydroxy-3β-O-[β-D-xylopyranosyl-(1→3)-β-Dglucopyranosyloxyuronic acid]-5α,14βporiferast-16-ene-15,23-dione = 1070.

464

Index 1 Compound Name and Synonym Index

45-Hydroxyyessotoxin = 186. Hymenosulfate = 953. Hymenosulphate = 953. Hypothemycin = 341. I Ibisterol C = 954. Ibisterol sulfate = 1103. Ibisterol sulfate B = 955. Ibisterol tri-O-sulfate = 1103. Iejimalide A = 535. Iejimalide B = 536. Iejimalide C = 537. Iejimalide D = 538. Ilicicolin C = 605. Incrustasterol A = 777. Incrustasterol B = 778. Incrusterol A = 777. Incrusterol B = 778. Indoxamycin A = 615. Indoxamycin B = 616. Indoxamycin C = 617. Indoxamycin D = 618. Indoxamycin E = 619. Indoxamycin F = 620. Iriomoteolide 4a = 539. Iriomoteolide 5a = 540. Isocyathisterol = 956. Iso-9,10-deoxytridachione = 606. Isogosterone A = 779. Isogosterone B = 780. Isogosterone C = 781. Isogosterone D = 782. Isohalichondrin C = 178. Isohomohalichondrin B = 187. 38-epi-Isohomohalichondrin B = 188. Isolaulamide = 524. Isolaulimalide = 524. Isomalyngamide A = 70. Isomalyngamide A1 = 71. Isomalyngamide B = 72. (3β,7α,22Z)-24-Isopropylcholesta-5,22-diene3,7-diol = 1087. Isoswinholide A = 473. J JBIR-124 = 284. JBIR-59 = 270.

K Karatungiol A = 29. Karlotoxin 3 = 140. Ketosteroid New = 1138. Kiheisterone A = 1055. Kiheisterone B = 1056. KmTx3 = 140. Koshikalide = 6. Kurilensoside A = 783. Kurilensoside B = 784. Kurilensoside C = 785. Kurilensoside D = 786. L Lasonolide A = 440. Lasonolide C = 441. Lasonolide D = 442. Lasonolide E = 443. Lasonolide F = 444. Lasonolide G = 445. Lathosterol = 709. Laulamide = 541. Laulimalide = 541. Leiodermatolide = 317. Lethasterioside A = 787. Levantilide A = 542. Leviusculoside J = 1020. Linckoside L1 = 788. Linckoside L2 = 789. Linckoside L7 = 1057. Linckoside M = 957. Linckoside N = 1058. Linckoside O = 1059. Linckoside P = 1060. Linckoside Q = 958. Lingshuiol = 30. Litosterol = 959. Lituarine A = 189. Lituarine B = 190. Lituarine C = 191. LL-Z 1272 ε = 607. Lobophorin A = 322. Lobophorin B = 323. Lobophorin G = 324. Lobophorin H = 325. Lobophorin I = 326. Lobophytosterol‡ = 1139. Lustromycin = 543.

Index 1 Compound Name and Synonym Index

Luteophanol A = 31. Lyngbouilloside = 544. Lyngbyaloside = 545. M Maclafungin = 50. Maduralide = 546. Maitotoxin (MTX) = 192. Malaitasterol A = 1140. Malyngamide 2 = 73. Malyngamide 3 = 74. Malyngamide 4 = 75. Malyngamide A = 76. Malyngamide B = 77. Malyngamide C = 78. 8-epi-Malyngamide C = 79. Malyngamide D = 80. Malyngamide E = 81. Malyngamide F = 82. Malyngamide H = 83. Malyngamide I = 84. Malyngamide J = 85. Malyngamide K = 86. Malyngamide L = 87. Malyngamide M = 88. Malyngamide N = 89. Malyngamide O = 90. Malyngamide R = 91. Malyngamide X = 92. Manadosterol A = 854. Manadosterol B = 855. Manauealide A = 249. Manauealide B = 250. Manauealide C = 251. Mandelalide A = 547. Mandelalide B = 548. Mangromicin A = 549. Marinomycin A = 550. Marinomycin B = 551. Marinomycin C = 552. Marinomycin D = 553. Marmycin A = 127. Marmycin B = 128. Marthasteroside B = 790. Mayamycin = 129. Mediasteroside M1 = 791. Mediasteroside M2 = 792. Mediasteroside M3 = 793. Mediasteroside M4 = 794.

465

3-Methoxyaplysiatoxin = 252. 6-Methoxycholest-7-ene-3,5-diol = 795. 3-Methoxydebromoaplysiatoxin = 253. 5-Methoxydihydrosterigmatocystin = 265. (22E)-7α-Methoxy-5α,6α-epoxyergosta-8(14),22dien-3β-ol = 960. 53-Methoxy-neoisohomohalichondrin B = 193. 3-Methoxy-19-norpregna-1,3,5(10),20-tetraene = 636. 6-O-Methylaverufin = 266. (3β,4α,5α,23S)-4-Methylcholesta-8,14-diene3,23-diol 3-O-[β-D-galactopyranosyl-(1→2)β-D-galactopyranoside] = 746. 24-Methylcholesta-5,24(28)-diene-3β,15β,19triol = 961. 24-Methylcholesta-5,24(28)-diene-3β,19-triol-7one = 962. (24R)-24-Methyl-5α-cholestane3β,5,6β,15α,24,28-hexaol 28-sulfate = 963. (24R,25S)-24-Methyl-5α-cholestane3β,5,6β,15α,16β,26-hexaol 26-sulfate = 964. 24-Methylcholesta-7,22,25-triene-3,5,6-triol = 870. (24S)-24-Methylcholest-5-ene-3β,25-diol = 965. (22E,24R,25S)-24-Methyl-5α-cholest-22-ene3β,5,6β,15α,26-pentol-26-sulfate = 966. (22E,24S)-24-Methyl-5α-cholest-22-ene3β,5,6β,15α,28-pentol 28-sulfate = 967. (3β,4α,5α)-4-Methylcholest-8-en-3-ol = 796. Methyl 9,10-didehydro-3,6-epoxy-4,6,8-triethyl2,4-dodecadienoic acid ester = 10. Methyl(2Z,6R,8S)-4,6-diethyl-3,6-epoxy-8methyldodeca-2,4-dienoate = 14. 24-Methylenecholestane-3,5,6,19-tetrol = 971. 24-Methylenecholesterol-5-ene-3β,16β-diol-3O-α-L-fucopyranoside = 968. 4-Methyleneergosta-8(14),24(28)-dien-3-ol = 882. 15-O-Methylenigmazole A = 554. Methyl 3,6-epoxy-4R, 8R-diethyl-6S-methyl-2Z, 9E-dodecadienoate = 15. Methyl-3,6-epoxy-4,8-diethyl-6-methyl-2dodecenoate = 16. (22S,24S)-24-Methyl-22,25-epoxyfurost-5-ene3β,20β-diol = 856. Methyl(2Z,6R,8S)-3,6-epoxy-4,6,8triethyldodeca-2,4-dienoate = 11.

466

Index 1 Compound Name and Synonym Index

25-Methylergostane-2,3,6-triol tri-O-sulfate = 929. 17R-Methylincisterol = 836. 55-O-Methylisohomohalichondrin B = 194. 20-Methylspirolide G = 223. 3-O-(2-O-Methyl-β-D-xylopyranosinyl)(3β,4β,5α,6β,15α,24S)-Cholestane3,4,6,8,15,24-hexol 24-O-[ɑ-Larabinofuranosyl-(1→2)-3-O- sulfo-ɑ-Larabinofuranoside] = 783. Micromonospolide A = 318. Micromonospolide B = 319. Micromonospolide C = 320. Minabeolide 1 = 1021. Minabeolide 2 = 1022. Minabeolide 4 = 797. Minabeolide 5 = 798. Minabeolide 8 = 799. Mirabalin = 555. Mirabilin = 555. Misakinolide A = 470. Miyakolide = 385. Muristerone A = 838. Myriaporone 3 = 32. Myriaporone 4 = 33. N Nebrosteroid N = 800. Nebrosteroid O = 969. Nebrosteroid P = 970. Neohomohalichondrin B = 180. Neolaulimalide = 556. Neomaclafungin A = 51. Neomaclafungin B = 52. Neomaclafungin C = 53. Neomaclafungin D = 54. Neomaclafungin E = 55. Neomaclafungin F = 56. Neomaclafungin G = 57. Neomaclafungin H = 58. Neomaclafungin I = 59. Neonorhalichondrin B = 195. Nephalsterol A = 971. Nephalsterol B = 972. Nephalsterol C = 973. Neristatin I = 557. Nidurufin = 267. Nigerasterol A = 974. Nigerasterol B = 975.

Niuhinone A = 34. Niuhinone B = 35. Nocardiopsin B = 388. Nonactin = 48. Nonactyl homononactoate = 46. (3β,6β,8β,15α,16β,22E,24ξ)-27-Norergosta4,22-diene-3,6,8,15,16,26-hexol 3-O-(2,3di-O-methyl-β-D-xylopyranoside) = 1020. Norhalichondrin A = 196. Norhalichondrin B = 197. Norhalichondrin C = 198. 24-Norisospiculoic acid = 608. 31-Noroscillatoxin B = 254. 19-Norpregna-1,3,5(10),20-tetraen-3-O-αfucopyranoside = 637. Norselic acid A = 1061. Norselic acid B = 1062. Norselic acid C = 976. Norselic acid D = 1063. Norselic acid E = 1064. Norspiculoic acid A = 609. 23-Norspiculoic acid B = 621. NSC 726108 = 455. NSC 362617 = 372. Numersterol A = 977. O 21-O-Octadecanoyl-xestokerol A = 1104. Octalactin A = 558. Okadaic acid = 224. 19-epi-Okadaic acid = 225. Okadaic acid 7-hydroxy-2,4-dimethyl-2E,4Eheptadienyl ester = 226. Okadaic acid 7-hydroxy-4-methyl-2-methylene4E-heptenyl ester = 227. 4Z-Onnamide A = 93. Onnamide A = 94. Onnamide B = 95. Onnamide C = 96. Onnamide D = 97. Onnamide F = 98. Ophidianoside E = 819. Ophidianoside F = 802. Ophirapstanol trisulfate = 803. Orbuticin = 559. Orostanal = 978. Orthoesterol C disulfate = 1023. Orthohippurinsterol A = 979.

Index 1 Compound Name and Synonym Index

Orthohippurinsterol B = 980. Orthohippurinsterone A = 981. Oscillariolide = 560. Oscillatoxin A = 255. Oscillatoxin B1 = 256. Oscillatoxin B2 = 257. Ostreasterol = 982. Ostreocin D = 141. Ostreol A = 17. 7-Oxobrefeldin A = 514. (20S,22E)-3-Oxochola-1,4,22-trien-24-oic acid methyl ester = 638. 3-Oxochol-4-en-24-oic acid = 639. 3-Oxoergosta-1,4,24(28)-trien-18-oic acid = 976. 11-Oxoonnamide A = 99. 17-Oxoonnamide B = 100. Oxosorbiquinol = 285. 3-Oxowitha-1,4,24-trienolide = 1021. P Pacific Ciguatoxin 1 = 199. Pacific Ciguatoxin 2 = 200. Pacific Ciguatoxin 3C = 201. Pacific Ciguatoxin 4B = 202. Paciforgin = 561. Pakisterol A = 1065. Palmerolide A = 562. 17-O-Palmitoyl-20-methylspirolide G = 228. Palmyrolide A = 563. Palytoxin = 132. Pandaroside A = 1066. Pandaroside A methyl ester = 1067. Pandaroside C = 804. Pandaroside C methyl ester = 805. Pandaroside D = 806. Pandaroside D methyl ester = 807. Pandaroside E = 983. Pandaroside E methyl ester = 984. Pandaroside F = 985. Pandaroside F methyl ester = 986. Pandaroside G = 1068. Pandaroside G methyl ester = 1069. Pandaroside H = 1070. Pandaroside H methyl ester = 1071. Pandaroside I = 1072. Pandaroside I methyl ester = 1073. Pandaroside J = 1074. Pandaroside J methyl ester = 1075.

Paraminabeolide A = 1024. Paraminabeolide B = 1025. Paraminabeolide C = 1026. Paraminabeolide D = 1027. Paraminabeolide E = 1028. Parguesterol A = 987. Parguesterol B = 988. Patusterol A = 989. PbTx8 = 156. PbTx1 = 146. PbTx2 = 147. PbTx3 = 162. PbTx5 = 153. PbTx6 = 154. PbTx7 = 155. P-CTX 1 = 199. P-CTX 2 = 200. P-CTX 3C = 201. Pectenotoxin 1 = 446. Pectenotoxin 2 = 447. Pectenotoxin 3 = 448. Pectenotoxin 4 = 449. Pectenotoxin 6 = 450. Pectenotoxin 7 = 451. Pectenotoxin 11 = 452. (36R)-Pectenotoxin 12 = 453. (36S)-Pectenotoxin 12 = 454. PectiniosideB = 990. Peloruside A = 564. Peloruside B = 565. Penicisteroid A = 991. 2β,3α,6β,11,19-Pentahydroxy-9,11secocholestan-9-one = 760. 2β,3β,6β,11,19-Pentahydroxy-9,11secocholestan-9-one = 817. Petrosterol = 1105. Petrosterol-3,6-dione = 1106. Phorbaside A = 305. Phorbaside C = 306. Phorbaside D = 307. Phorbaside E = 308. Phormidolide = 566. Phrygiasterol = 1107. Phrygioside B = 808. Pinnasterol = 809. Pinnatoxin A = 229. Pinnatoxin B = 230. Pinnatoxin C = 231. Pinnatoxin D = 232.

467

468

Index 1 Compound Name and Synonym Index

Poecillastrin A = 455. Poecillastrin B = 456. Poecillastrin C = 457. Polycavernoside A = 567. Polycavernoside A2 = 568. Polycavernoside A3 = 569. Polycavernoside B = 570. Polycavernoside B2 = 571. Polymastiamide A = 992. Portimine = 625. Precandidaspongiolide A = 572. Precandidaspongiolide B = 573. Pregnenolone = 631. Prorocentrol = 18. Prorocentrolide = 574. Prorocentrolide B = 575. Protoceratin I = 203. Protoceratin II = 204. Protoceratin III = 205. Protoceratin IV = 206. Prymnesin 1 = 207. Prymnesin 2 = 208. Pteriatoxin A = 233. Pteriatoxin B = 234. Pteriatoxin C = 235. PTX = 132. PTX1 = 446. PTX11 = 452. 36-αOH-PTX12 = 453. 36-βOH-PTX12 = 454. PTX2 = 447. PTX3 = 448. PTX4 = 449. PTX6 = 450. PTX7 = 451. Punicinol A = 810. Punicinol B = 811. R Rathbunioside R1 = 812. Rathbunioside R2 = 813. Regularoside A = 993. Reidispongiolide A = 458. Reidispongiolide B = 459. Reidispongiolide C = 460. Remeisterol = 994. Rifamycin S = 114. Riisein A = 814. Riisein B = 815.

S Saiyacenol A = 36. Saiyacenol B = 37. Salarin A = 576. Salicylihalamide A = 342. Salicylihalamide B = 343. Saliniketal A = 38. Saliniketal B = 39. Salinisporamycin = 115. Sanguinoside C = 995. Sclerosteroid A = 632. Sclerosteroid B = 633. Sclerosteroid E = 634. Scytophycin E = 577. 9,10-Secocholesta-1,3,5(10),24-tetraene-3,9diol = 1116. 9,10-Secoergosta-1,3,5(10),22-tetraene-3,9-diol = 1120. 9,11-Seco-24-hydroxydinosterol = 996. Sepositoside A = 816. Seragakinone A = 119. Shimalactone A = 622. Shimalactone B = 623. Shishicrellastatin A = 1141. Shishicrellastatin B = 1142. Simplakidine A = 40. Sinubrasolide A = 1029. Sinubrasolide B = 1030. Sinubrasolide E = 1031. Sinulabasterol = 997. Sinularoside A = 998. Sinularoside B = 999. Siphonarienedione = 41. Z-Siphonarienfuranone = 42. Siphonarienfuranone = 43. Siphonarienolone = 44. Solomonsterol A = 640. Solomonsterol B = 641. (3R,5R)-Sonnerlactone = 344. (3R,5S)-Sonnerlactone = 345. Sorbicatechol A = 286. Sorbicatechol B = 287. Sorbicillactone A = 288. Sorbicillamine A = 289. (R)-Sorbicillamine B = 290. (S)-Sorbicillamine B = 291. Sorbicillamine C = 292. Sorbicillamine D = 293. Sorbicillamine E = 294.

Index 1 Compound Name and Synonym Index

Sorbicillin = 295. Sorbiterrin A = 296. Sphinxolide A = 461. Sphinxolide B = 462. Sphinxolide C = 463. Sphinxolide D = 464. Sphinxolide E = 465. Sphinxolide F = 466. Sphinxolide G = 467. Spiculoic acid A = 610. Spirolide A = 236. Spirolide B = 237. Spirolide C = 238. Spirolide D = 239. Spirolide E = 240. Spirolide F = 241. Spirolide G = 242. Spiroprorocentrimine = 578. Splenocin A = 352. Splenocin B = 353. Splenocin C = 354. Splenocin D = 355. Splenocin E = 356. Splenocin F = 357. Splenocin G = 358. Splenocin H = 359. Splenocin I = 360. Splenocin J = 361. Spongidepsin = 19. Spongistatin 1 = 579. Spongistatin 2 = 580. Spongistatin 3 = 581. Spongistatin 4 = 582. Spongistatin 5 = 583. Spongistatin 8 = 584. Spongistatin 9 = 585. SPX = 214. Stellettasterol = 817. Sterigmatocystin = 268. (24R)-Stigmasta-4,25-diene-3,6-diol = 1076. (3β,6β,15α,16β,22E,24R,25S)-Stigmasta-4,22diene-3,6,8,15,16,26-hexol 3-O-(2-Omethyl-β-D-xylopyranoside) 26-O-β-Dxylopyranoside = 1058. (3β,6β,15α,16β,22E,24R)-Stigmasta-4,22-diene3,6,8,15,16,29-hexol 3-O-(2-O-methyl-β-Dxylopyranoside) 29-O-β-D-xylopyranoside = 1059.

469

(3β,6β,15α,16β,22E,24R)-Stigmasta-4,22-diene3,6,8,15,16,29-hexol 3-O-(2-O-methyl-β-Dxylopyranoside) 29-O-β-D-xylopyranoside 15-sulfate = 1057. (3β,6α,15β,24(28)E)-Stigmasta-8(14),24(28)diene-3,6,15,29-tetrol 29-O-β-Dxylopyranoside = 1038. Stigmasta-4,24(28)-dien-3-one = 1077. (3β,4β,5α,6α,8β,15β,24R)-Stigmastane3,4,6,8,15,29-hexol 29-O-[2-O-methyl-β-Dxylopyranosyl-(1→2)-β-D-xylopyranoside] = 1037. (3β,4β,5α,6α,8β,15β,24R)-Stigmastane3,4,6,8,15,29-hexol 29-O-[β-Dxylopyranosyl-(1→2)-β-D-xylopyranoside] = 1036. (3β,6β,8β,15α,16β,24R)-Stigmast-4,25-diene3,6,8,15,16,29-hexol 3-O-(2-O-methyl-β-Dxylopyranoside) 29-O-β-D-xylopyranoside = 1060. Stigmast-25-ene-2,3,15,16,17,18-hexol 2-Osulfate = 1078. Stoloniferone A = 1000. Stoloniferone B = 1001. Stoloniferone C = 1002. Stoloniferone D = 1108. Stoloniferone E = 1003. Stoloniferone F = 1004. Stoloniferone G = 1005. Stoloniferone T = 1006. Stoloniolide I = 1007. Stoloniolide II = 1008. Streptobactin = 362. Streptoseolactone = 818. Stylocheilamide = 101. 10-O-Sulfo-KmTx1 = 143. 10-O-Sulfo-KmTx3 = 144. Sumalarin A = 346. Sumalarin B = 347. Sumalarin C = 348. Superstolide A = 586. Superstolide B = 587. Swinhoeisterol A = 1143. Swinhoeisterol B = 1144. Swinholide A = 474. Swinholide B = 475. Swinholide C = 476. Swinholide H = 477. Swinholide I = 478.

470

Index 1 Compound Name and Synonym Index

Swinholide K = 479. Symbiodinolide = 118. Symbiopolyol = 142. T Tamulamide A = 209. Tamulamide B = 210. Tartrolone D = 588. Tedanolide = 589. (3β,5α,6α,22R)-3,6,20,25Tetrahydroxycholesta-9(11),23-dien-22-one 6-O-[β-D-fucopyranosyl-(1→2)-6-deoxy-βD-glucopyranosyl-(1→4)- [6-deoxy-3-Omethyl-β-D-glucopyranosyl-(1→2)]-β-Dxylopyranosyl-(1→3)-6-deoxy-β-Dglucopyranoside] 3-O-sulfate = 755. 2,5,6,11-Tetrahydroxyergosta-3,24(28)-dien-1one = 1005. (2β,5β,6β,11α,24S)-2,5,6,11Tetrahydroxyergost-3-en-1-one = 1006. Tetromycin 1 = 327. Tetromycin 2 = 328. Tetromycin 3 = 329. Tetromycin 4 = 330. Tetromycin B = 331. Theonellasterol B = 1079. Theonellasterol C = 1080. Theonellasterol D = 1081. Theonellasterol E = 1082. Theonellasterol F = 1083. Theonellasterol G = 1084. Theonellasterol H = 1085. Theonellasterol K = 1086. Theopederin A = 102. Theopederin B = 103. Theopederin C = 104. Theopederin D = 105. Theopederin E = 106. Theopederin F = 107. Theopederin G = 108. Theopederin H = 109. Theopederin I = 110. Theopederin J = 111. Theopederin K = 112. Theopederin L = 113. Thornasteroside A = 819. Tolytoxin = 590. Topsentiasterol sulfate A = 1009.

Topsentiasterol sulfate B = 1010. Topsentiasterol sulfate C = 1011. Topsentiasterol sulfate D = 1012. Topsentiasterol sulfate E = 1013. Topsentinol B = 1087. Toxin GB1 = 146. Tribenarthin = 363. Trichodermaketone A = 624. Trichodermanone A = 297. Trichodermanone B = 298. Trichodermanone C = 299. Trichodimerol = 300. (3β,6α,22R)-3,6,20-Trihydroxy-9(11),24cholestadien-22-one 6-O-[β-Dfucopyranosyl-(1→2)-6-deoxy-β-Dglucopyranosyl-(1→4)-[6-deoxy- 3-Omethyl-β-D-glucopyranosyl-(1→2)]-β-Dxylopyranosyl-(1→3)-6-deoxy-β-Dglucopyranoside] 3-O-sulfate = 757. 3,6,24-Trihydroxycholestan-15-one = 820. (3β,5α,6α,20S)-3,6,20-Trihydroxycholest-9(11)en-23-one 6-O-[β-D-fucopyranosyl-(1→2)β-D-xylopyranosyl-(1→4)-[6-deoxy-β-Dgluco- pyranosyl-(1→2)]-β-D-xylopyranosyl(1→3)-6-deoxy-β-D-glucopyranoside] 3-Osulfate = 802. 3,11,24-Trihydroxy-4,23-dimethyl-9,11secoergost-22-en-9-one = 996. 3β,7β,11-Trihydroxy-5α,6α-epoxy-9,11secogorgostan-9-one = 1109. 3β,5α,9α-Trihydroxy-(22E,24R)-ergosta-7,22dien-6-one = 1014. 5,6,11-Trihydroxy-33-norgorgost-2-en-1-one = 1112. (3β,24ξ)-3,11,24-Trihydroxy-9,11-secogorgost-5en-9-one = 1110. 45,46,47-Trinoryessotoxin = 211. Trisorbicillinone A = 301. Trisorbicillinone B = 302. Trisorbicillinone C = 303. Trisorbicillinone D = 304. Tubaymycin = 309. Tulearin A = 591. U Urauchimycin A = 364. Urauchimycin B = 365. Urdamycin E = 130. Urdamycinone G = 131.

Index 1 Compound Name and Synonym Index

V Vatoxin-a = 45. Versicolorin C = 269. Volemolide = 836. W Weinbersteroldisulfate A = 1111. Werramycin = 48. Wondosterol A = 1015. Wondosterol B = 821. Wondosterol C = 822. X Xestobergsterol A = 823. Xestobergsterol B = 824. Xestobergsterol C = 825.

Y Yessotoxin = 212. Yonarasterol A = 1016. Yonarasterol B = 1017. 6-epi-Yonarasterol B = 1018. Yonarasterol C = 1112. Yonarasterol E = 1019. YTX = 212. Z Zampanolide = 592. Zooxanthellatoxin A = 593. Zooxanthellatoxin B = 594.

471

Index 2 Compound Molecular Formula Index The Molecular Formula Index of Volume 5 lists the molecular formulae of all 1,144 active isolated compounds from marine organisms given in the HAMNP Volume 5 in Hill convention order. Under a bold formula, all related compound names following code numbers are listed in the code number order too. C12 C12H16O4 – Balticolid, 1. C13 C13H16O3 – Dihydrodemethylsorbicillin, 278. C14 C14H16O3 – Sorbicillin, 295. C14H16O5 – Epoxysorbicillinol, 283. C14H18O3 – 2ʹ,3ʹ-Dihydrosorbicillin, 280. C14H18O5 – (3R,5R)-Sonnerlactone, 344. – (3R,5S)-Sonnerlactone, 345. C14H18O6 – Colletoketol, 61. – Grahamimycin A1, 63. C14H20O6 – Clonostachydiol, 60. C14H22O6 – 9,10-Dihydrocolletodiol, 62. C16 C16H16O6 – Curvulone A, 335. C16H18O5 – 10,11-Dehydrocurvularin, 337. C16H18O6 – 10,11-Dehydro-13-hydroxycurvularin, 338. C16H20O6 – 11α-Hydroxycurvularin, 339. – 11β-Hydroxycurvularin, 340. – Herbarone, 614. C16H22O4 – 7-Dehydrobrefeldin A, 514. C16H24O4 – Brefeldin A, 497.

C16H24O5 – Trichodermaketone A, 624. C16H26O3 – Aspermytin A, 596. C16H26O5 – Decumbenone C, 598. C17 C17H22O6 – Curvulone B, 336. C17H26O4 – Koshikalide, 6. C17H30O4 – Aspericin A, 22. – Aspericin C, 23. C18 C18H12O6 – Asperxanthone, 259. – Sterigmatocystin, 268. C18H12O7 – Versicolorin C, 269. C18H14O7 – Hemiacetal sterigmatocystin, 264. C18H22O6 – Aigialomycin D, 333. – Aigialomycin E, 334. C18H23NO4 – Sorbicillamine A, 289. C18H30O3 – Methyl(2Z,6R,8S)-4,6-diethyl-3,6-epoxy-8methyldodeca-2,4-dienoate, 14. – Methyl 3,6-epoxy-4R,8R-diethyl-6S-methyl2Z,9E-dodecadienoate, 15. C18H32O3 – Methyl-3,6-epoxy-4,8-diethyl-6-methyl-2dodecenoate, 16. C19 C19H14O6 – Antibiotic SS-228Y, 120.

Index 2 Compound Molecular Formula Index

C19H16O7 – 5-Methoxydihydrosterigmatocystin, 265. C19H22O8 – Aigialomycin A, 332. – Hypothemycin, 341. C19H24O8S – Sumalarin C, 348. C19H28O4 – Gracilioether B, 12. C19H30O3 – 2-[3,5-Diethyl-5-(2-ethyl-3-hexen-1-yl)-2(5H)furanylidene]acetic acid methyl ester, 10. C19H30O4 – Gracilioether C, 13. C19H32O3 – 2-[3,5-Diethyl-5-(2-ethylhexyl)-2(5H)-furanylidene]acetic acid methyl ester, 11. C19H32O6 – Octalactin A, 558. C19H32O7 – Myriaporone 3, 32. – Myriaporone 4, 33. C20 C20H16O7 – Aversin, 260. – Averufin, 261. – Nidurufin, 267. C20H16O8 – Acyl-hemiacetal sterigmatocystin, 258. C20H18O2 – Cinanthrenol A, 1132. C20H20O6 – Sorbiterrin A, 296. C20H26O8 – Trichodermanone C, 299. C20H26O8S – Sumalarin A, 346. C20H34O3 – Z-Siphonarienfuranone, 42. – Siphonarienfuranone, 43. C20H35NO3 – Palmyrolide A, 563. C20H38O2 – Siphonarienolone, 44. C21 C21H18O7 – 6-O-Methylaverufin, 266.

C21H23ClO7 – Chloctanspirone A, 275. – Chloctanspirone B, 276. C21H23NO8 – Sorbicillactone A, 288. C21H26O5 – 3,4-Dihydroxypregna-5,15-diene-20-one19,2- carbolactone, 627. C21H28O – 3-Methoxy-19-norpregna-1,3,5(10), 20-tetraene, 636. C21H28O6 – Amphidinolide O, 417. C21H28O8 – Trichodermanone A, 297. – Trichodermanone B, 298. C21H29O7Cl – Haterumalide NE, 531. C21H32O2 – Pregnenolone, 631. C21H34O4 – Amphidinolide Q, 419. C21H34O8 – Paciforgin, 561. C21H36O2 – Siphonarienedione, 41. C21H36O7 – Feigrisolide C, 46.

C22 C22H20O7 – 6,8-Di-O-methylaverufin, 262. C22H20O8 – 6,8-Di-O-methylnidurufin, 263. C22H28O7 – Cochliomycin A, 321. C22H30N2O8 – Urauchimycin A, 364. – Urauchimycin B, 365. C22H30O3 – Iso-9,10-deoxytridachione, 606. – Indoxamycin A, 615. C22H30O4 – Indoxamycin B, 616. – Indoxamycin C, 617. – Indoxamycin D, 618. – Indoxamycin E, 619. – Indoxamycin F, 620.

473

474

Index 2 Compound Molecular Formula Index

C22H30O5 – Amphidinolide P, 418. C22H32O6 – Akaeolide, 611. C22H34O3 – 17R-Methylincisterol, 836. C22H34O7 – Mangromicin A, 549. C22H35O4 – Sclerosteroid E, 634. C22H36O6 – 10-Hydroxy-18-O-methylbetaenone C, 604. C22H37NO5 – Saliniketal A, 38. C22H37NO6 – Saliniketal B, 39. C22H37NO9 – Theopederin E, 106. C22H38O4 – Amphidinin A, 20. C22H38O7 – Feigrisolide D, 47. C23 C23H26O6 – Sorbicatechol A, 286. – Sorbicatechol B, 287. C23H28O5 – Dactylolide, 513. C23H28O7 – Antibiotic JBIR 59, 270. C23H29ClO4 – Ascochlorin, 595. C23H30O4 – Cylindrol B, 597. C23H31ClO4 – Ilicicolin C, 605. C23H31NO5 – Portimine, 625. C23H31O8Cl – Haterumalide NA, 527. C23H31O9Cl – Haterumalide ND, 530. C23H32O3 – 16β-Hydroxy-5α-pregna-1,20-dien-3-one-16acetate, 630. C23H32O4 – LL-Z 1272 ε, 607.

C23H36O3 – Sclerosteroid A, 632. C23H38O4 – Sclerosteroid B, 633. C23H40O5 – Denticulatin A, 25. – Denticulatin B, 26. C23H40O12S3 – Solomonsterol B, 641. C24 C24H26N2O8 – Splenocin J, 361. C24H30O5 – Dihydrotrichodermolide, 281. C24H32N2O9 – Antimycin A20, 350. C24H36O3 – Niuhinone A, 34. – 3-Oxochol-4-en-24-oic acid, 639. C24H36O4 – Amphidinolide S, 421. C24H37NO6 – Simplakidine A, 40. C24H38ClNO3 – Malyngamide K, 86. C24H38ClNO4 – Malyngamide F, 82. C24H38ClNO5 – Malyngamide C, 78. – 8-epi-Malyngamide C, 79. C24H38O4 – Amphidinolide J, 412. – Amphidinolide W, 429. C24H42O12S3 – Solomonsterol A, 640. C25 C25H32O3 – Dinorspiculoic acid, 600. C25H32O4 – Amphidinolide V, 428. C25H32O6 – JBIR-124, 284. C25H32O11S – Sumalarin B, 347. C25H34O3 – (20S,22E)-3-Oxochola-1,4,22-trien-24-oic acid methyl ester, 638.

Index 2 Compound Molecular Formula Index

C25H36O2 – Gelliusterol B, 829. C25H36O4 – 3α,16β-Dihydroxy-5α-pregna-1,20-diene-3,16diacetate, 628. C25H38O2 – Gelliusterol A, 828. C25H38O3 – Niuhinone B, 35. C25H38O4 – Fusarielin A, 601. C25H39ClO4 – Dehydroxychlorofusarielin B, 599. – Fusarielin E, 603. C25H40O5 – Fusarielin B, 602. C25H42ClNO5 – Malyngamide O, 90. C25H42ClNO6 – Malyngamide 2, 73. C25H42O5 – Amphidinolide T1, 422. – Amphidinolide T3, 424. – Amphidinolide T4, 425. – Amphidinolide T5, 426. C25H42O6 – Arenolide, 490. C26 C26H22ClNO4 – Marmycin B, 128. C26H23NO4 – Marmycin A, 127. C26H25NO7 – Mayamycin, 129. C26H26O9S – Urdamycinone G, 131. C26H26O12 – Seragakinone A, 119. C26H28N2O9 – Splenocin A, 352. – Splenocin D, 355. C26H30N2O10 – Antimycin B2, 351. C26H33NO5 – Salicylihalamide A, 342. – Salicylihalamide B, 343. C26H34O3 – 24-Norisospiculoic acid, 608.

475

– Norspiculoic acid A, 609. C26H36O5 – 19-Norpregna-1,3,5(10),20-tetraen-3-O-αfucopyranoside, 637. C26H40ClNO3 – Malyngamide M, 88. C26H40ClNO4 – Malyngamide N, 89. C26H40ClNO5 – 6-O-Acetylmalyngamide F, 66. C26H40ClNO6 – 8-O-Acetylmalyngamide C, 64. – 8-O-Acetyl-8-epi-malyngamide C, 65. C26H40O2 – 24-Hydroxy-26,27-dinorergosta-4,22E-dien-3one, 834. – Calicoferol H, 1117. C26H40O3 – Amphirionin 4, 21. C26H40O4 – 3,6-Dihydroxy-24-nor-9-oxo-9,11secocholesta-7,22-dien-11-al, 731. – Glaciasterol A, 830. C26H40O6 – Amphidinolide X, 430. C26H41NO10 – Theopederin D, 105. C26H41NO4 – Malyngamide H, 83. C26H42ClNO4 – Malyngamide L, 87. C26H42ClNO5 – Malyngamide I, 84. C26H42O4 – 7,8-Epoxy-26,27-dinorergost-23-ene-3,5,6triol, 827. C26H42O6 – Amphidinolide Y, 431. C26H44O6 – Amphidinolide T2, 423. C26H44O12S3 – Halistanol sulfate B, 831. – Halistanol sulfate D, 832. C26H46O11 – Peloruside B, 565. C27 C27H34N2O6 – Discodermide, 613.

476

Index 2 Compound Molecular Formula Index

C27H36O3 – Spiculoic acid A, 610. C27H39ClO8 – Haterumalide NB, 528. C27H39ClO9 – Haterumalide NC, 529. C27H39NO3 – Spongidepsin, 19. C27H40O2 – 18,22-Epoxycholesta-1,20(22)-dien-3-one, 741. – Gelliusterol C, 753. – Calicoferol A, 1114. C27H40O3 – Minabeolide 4, 797. – 22ξ-Hydroxyfurosta-1,4-dien-3-one, 851. C27H40O4 – Anastomosacetal A, 659. – (20S)-18,20-Dihydroxycholesta-1,4-diene3,16-dione, 726. – 25-Hydroperoxycholesta-4,23-diene-3,6dione, 764. – 24ξ-Hydroperoxycholesta-4,25-diene-3,6dione, 765. – 22(R)-Hydroxy-3,16-dioxocholest-4-en-18-al, 776. C27H40O5 – Amphidinolide K, 413. C27H40O6S – 29-Demethylgeodisterol-3-O-sulfate, 886. C27H42O – Dendronesterone A, 723. C27H42O2 – Cholest-4-ene-3,24-dione, 696. – (24R)-Hydroxycholesta-4,22E-dien-3-one, 770. – 3β-Hydroxycholesta-5,24-dien-23-one, 771. – Chabrosterol, 872. – Calicoferol G, 1116. C27H42O3 – Astropectenol C, 668. – (5α,22ξ,23ξ)-22,23-Dihydroxycholesta-1,24dien-3-one, 727. – 24,25(R/S)-Epoxy-6β-hydroxycholest-4-en-3one, 744. – (20S)-20-Hydroxycholest-1-ene-3,16-dione, 774. – 22ξ-Hydroxyfurost-1-en-3-one, 852. – Calicoferol I, 1118.

C27H42O4 – 24ξ-Hydroperoxy-6β-hydroxycholesta-4,25dien-3-one, 768. – 25-Hydroperoxy-6β-hydroxycholesta-4,23dien-3-one, 769. C27H42O5 – Biselyngbyolide A, 495. – Incrustasterol B, 778. – Pinnasterol, 809. C27H42O6S – Cholesta-5,24-diene-3-O-sulfate-19-carboxylic acid, 675. – (3β,5α,6α)-3,6-Dihydroxycholesta-9(11),24dien-23-one 3-sulfate, 728. C27H42O10S – Forbeside E3, 629. C27H43NO10 – Theopederin C, 104. C27H44O – 24-Dehydrocholesterol, 721. C27H44O2 – Cholesta-5,23E-dien-3β,25-diol, 673. – Cholesta-5,25-diene-3β,24ξ-diol, 674. – 3β-Hydroxycholest-5-en-7-one, 775. – Astrogorgiadiol, 1113. C27H44O3 – (3β,7β,22E)-Cholesta-5,22-diene-3,7,19-triol, 676. – Cholesta-7,22-diene-3β,5α,6β-triol, 677. – 6β,16β-Dihydroxycholest-4-en-3-one, 730. – 5,8-epi-Dioxycholesta-6-en-3-ol, 733. – 5β,6β-Epoxycholest-24-ene-3β,7β-diol, 743. – 25-Hydroperoxycholesta-5,(23E)-dien-3β-ol, 766. – 24ξ-Hydroperoxycholesta-5,25-dien-3β-ol, 767. – (20S)-20-Hydroxycholestane-3,16-dione, 772. – 16β-Hydroxy-5α-cholestane-3,6-dione, 773. – Calicoferol B, 1115. C27H44O4 – Astropectenol B, 667. C27H44O5 – Incrustasterol A, 777. – Xestobergsterol A, 823. C27H44O6 – Xestobergsterol C, 825. C27H44O6S – Cholesta-5-ene-3-O-sulfate-19-carboxylic acid, 678.

Index 2 Compound Molecular Formula Index

C27H44O7 – Xestobergsterol B, 824. – Crustecdysone, 837. C27H44O8 – Muristerone A, 838. C27H44O9S22− – (3β,5α,6α,23S)-Cholest-9(11)-ene-3,6,23-triol 3,6-disulfate (disodium salt), 708. C27H45NO10 – Theopederin A, 102. C27H46O – (3β,5α)-Cholest-7-en-3-ol, 709. – Cholesterol, 710. C27H46O2 – Astropectenol D, 669. – Cholest-4-ene-3α,6β-diol, 694. C27H46O3 – Astropectenol A, 666. – (3β,7β)-Cholest-5-ene-3,7,19-triol, 703. – Cholest-24-ene-(3α,6β,7β)-triol, 704. – Cholest-7-ene-3,5,6-triol, 705. – (16S,20S)-16,20-Dihydroxycholestan-3-one, 729. – (3β,22S)-Ergosta-5,24(28)-diene-3,17,22-triol, 912. C27H46O4 – (3β,7β,9α)-Cholest-5-ene-3,7,9,19-tetrol, 701. – 7,8-Epoxycholestane-3,5,6-triol, 742. – 3,6,24-Trihydroxycholestan-15-one, 820. C27H46O5 – Cholest-22E-ene-3β,6β,8β,15α,24R-pentol, 700. C27H46O6 – (3β,4β,5α,6α,8β,15β,22E,24R)-Cholest-22ene-3,4,6,8, 15,24-hexol, 698. – (25R)-Cholest-22-ene-3,6,8,15,16,26-hexol, 699. – Phrygiasterol, 1107. C27H46O7 – Euryspongiol A1, 747. C27H46O8S2 – 3α-Cholest-5-ene-3,21-diol 3,21-disulfate, 695. C27H46O9S2 – (2β,3α)-Cholest-5-ene-2,3,21-triol 3,21disulfate, 706. – Cholest-5-ene-1,3,21-triol-3,21-disulfate, 707.

477

C27H46O10S – (3β,4β,5α,6α,7α,8β,15β,24R)-Cholest-22Eene-3,4,6,7,8,15,24-heptol 6-O-sulfate, 697. C27H46O10S2 – (20R)-Cholest-5-ene-2α,3α,4β,21-tetrol 3,21disulfate, 702. C27H47NO7 C27H47NO10 – Theopederin F, 107. C27H48O5 – (25S)-5β-Cholestane-3β,6β,15α,16β,26pentol, 688. – (25R)-5α-Cholestane-3β,6β,15α,16β,26pentol, 689. C27H48O6 – (3β,4β,5α,6β,15α,24S)-Cholestane3,4,6,8,15,24-hexol, 684. – (3β,4β,5α,6α,15β,24S)-Cholestane3,4,6,8,15,24-hexol, 685. – (3β,5α,6β,7α,15α,16β)-Cholestane3,6,7,15,16,26-hexol, 686. – Cholestane-3,6,8,15,16,26-hexol, 687. – Herbasterol, 760. – Stellettasterol, 817. C27H48O7 – Cholestane-3,6,8,15,16,25,26-heptol, 680. – (3β,4β,5α,6β,8β,15β,24R)-Cholestane3,4,6,8,15,24,25-heptol, 681. – Euryspongiol A2, 748. C27H48O8S – (24S)-5α-Cholestane-3β,5,6β,15α,24-pentol 15-sulfate, 690. – 5α-Cholestane-3β,5,6β,15α,16β-pentol 16sulfate, 691. C27H48O9S – (25S)-5α-Cholestane-3β,5,6β,15α,16β,26hexaol 26-sulfate, 682. – (25S)-5α-Cholestane-3β,5,6β,15α,16β,26hexaol 16-sulfate, 683. C27H48O9S2 – (3α,4β,5α)-Cholestane-3,4,21-triol 3,21-di-Osulfate, 693. C27H48O10S2 – 5β-Cholestane-3α,4α,11β,21-tetraol 3,21disulfate, 692. C27H48O11 – Peloruside A, 564.

478

Index 2 Compound Molecular Formula Index

C27H48O12S3 – Halistanol sulfate C, 758. C28 C28H32N2O9 – Splenocin B, 353. – Splenocin E, 356. C28H32O8 – Bisorbibutenolide, 271. – Bisorbicillinol, 272. – Trichodimerol, 300. C28H32O9 – Bisvertinolone, 273. – Oxosorbiquinol, 285. – Sorbicillamine E, 294. C28H33NO8 – Sorbicillamine C, 292. C28H34O8 – Bisvertinoquinol, 274. – Dihydrotrichodimerol, 282. C28H34O9 – 10,11-Dihydrobisvertinolone, 277. – 10,11-Dihydro-oxosorbiquinol, 279. C28H35NO8 – (R)-Sorbicillamine B, 290. – (S)-Sorbicillamine B, 291. C28H36O4 – Paraminabeolide A, 1024. C28H37ClO9 – Haterumalide B, 526. C28H38O2 – Gymnasterone D, 924. C28H38O3 – Minabeolide 1, 1021. C28H38O4 – Sinubrasolide A, 1029. – Sinubrasolide B, 1030. C28H38O5 – Sinubrasolide E, 1031. C28H38O6 – 3-(4-O-Acetyl-6-deoxy-β-galactopyranosyloxy)19-nor- pregna-1,3,5(10),20-tetraene, 635. C28H39NO4 – Aureoverticillactam, 2. C28H40N2O8 – Antimycin A19, 349. C28H40O – (22E,24R)-Ergosta-4,6,8(14),22-tetraen-3-one, 915.

C28H40O2 – Gymnasterone C, 923. – 3β-Hydroxy-( 22E,24R)-ergosta-5,8,14,22tetraen-7-one, 948. – 15α-Hydroxy-(22E,24R)-ergosta-3,5,8(14),22tetraen-7-one, 949. C28H40O3 – Dankasterone A, 880. – Gymnasterone B, 922. – 3β-Hydroxy-(22E,24R)-ergosta-5,8,22-trien7,15-dione, 950. – 3β-Hydroxyl-(22E,24R)-ergosta-5,8(14),22trien-7,15-dione, 951. – Norselic acid C, 976. C28H40O4 – Paraminabeolide D, 1027. – Paraminabeolide E, 1028. C28H40O7 – 4,5-Epoxy-2,3,12,22-tetrahydroxy-14methylcholesta- 7,9(11)-diene-6,24-dione, 745. C28H42O2 – 3β-Hydroxyl-(22E,24R)-ergosta-5,8,22-trien-7one, 952. – Isocyathisterol, 956. – Calicoferol D, 1119. C28H42O3 – Dankasterone B, 881. – 9(11)-Dehydroergosterol peroxide, 883. – 3β,15a-Dihydroxy-(22E,24R)-ergosta-5,8 (14),22-trien-7-one, 888. – 3β,15β-Dihydroxy-(22E,24R)-ergosta-5,8 (14),22-trien-7-one, 889. – Stoloniolide I, 1007. C28H42O4 – (22E)-3β-Hydroxy-5α,6α:14α,15αdiepoxyergosta-22-en-7-one, 947. – Nigerasterol A, 974. – Nigerasterol B, 975. – 3-O-Deacetyl-22,23-dihydro-24,28didehydroluffasterol B, 1123. – 3-O-Deacetylluffasterol B, 1124. C28H42O7 – Hemibrevetoxin B, 181. C28H43ClN2O4 – Isomalyngamide A1, 71. C28H43ClN2O5 – Malyngamide 4, 75.

Index 2 Compound Molecular Formula Index

C28H44ClNO6 – Stylocheilamide, 101. C28H44O2 – Parguesterol A, 987. C28H44O3 – Biemnasterol, 870. – 5α,8α-epi-Dioxyergosta-6,22-dien-3β-ol, 891. – (22E,24R)-5α,6α-Epoxy-3β-hydroxyergosta22-ene-7-one, 899. – 24-Methylcholesta-5,24(28)-diene-3β,19-triol7-one, 962. – Stoloniferone E, 1003. – Stoloniolide II, 1008. C28H44O4 – 11-Dehydroxy-22-epi-hippuristanol-3-one, 844. – (22S,24S)-24-Methyl-22,25-epoxyfurost-5ene-3β,20β-diol, 856. – 3β,5α,9α-Trihydroxy-(22E,24R)-ergosta-7,22dien-6-one, 1014. – Yonarasterol E, 1019. C28H44O5 – Stoloniferone G, 1005. – (22E)-11-Acetoxy-3β,6α-dihydroxy-24-nor-9,11seco -5α-cholesta-7,22-dien-9-one, 1122. C28H44O6 – (2α,5α,11β,20R,22S,24S)-4(3→2)-Abeo-22,25epoxy- 11,20-dihydroxy-24-methylfurostan3-oic acid, 835. – Calicoferol F, 1120. C28H45ClN2O6 – Isomalyngamide B, 72. – Malyngamide B, 77. C28H46O – Ostreasterol, 982. C28H46O2 – (3β,23S)-Ergosta-5,24(28)-diene-3,23-diol, 900. – (3β,23R)-Ergosta-5,24(28)-diene-3,23-diol, 901. – (3β,25)-Ergosta-5,24(28)-diene-3,25-diol, 902. – Ergosta-4,24(28)-diene-3β,6β-diol, 903. – Litosterol, 959. C28H46O3 – Cerevisterol, 871. – Crassarosterol A, 876. – Gibberoepoxysterol, 919.

479

– 7β-Hydroperoxy-24-methylenecholersterol, 946. – 24-Methylcholesta-5,24(28)-diene-3β,15β,19triol, 961. – Nephalsterol B, 972. – Parguesterol B, 988. – Patusterol A, 989. C28H46O4 – 11-Dehydroxy-22-epi-hippuristanol, 843. – 7,8-Epoxyergost-22-ene-3,5,6-triol, 898. – Ergosta-8(14),22-diene-3β,5α,6β,7α-tetraol, 910. – (3β,6α,15β,22E,24R,25S)-Ergosta-8(14),22diene-3,6, 15,26-tetrol, 911. – Gibberoketosterol, 920. C28H46O5 – Acalycigorgia inermis sterol C, 644. – Hippuristanol, 849. – 22-epi-Hippuristanol, 850. – Stoloniferone F, 1004. – Stoloniferone T, 1006. C28H46O6 – 2-Desacetyl-22S-epi-hippurin 1, 845. – 2α-Hydroxyhippuristanol, 853. C28H47NO11 – Theopederin B, 103. C28H48O – (3β,4α,5α)-4-Methylcholest-8-en-3-ol, 796. – Fungisterol, 918. C28H48O2 – (24S)-Ergost-5-ene-3β,7α-diol, 916. – (24S)-24-Methylcholest-5-ene-3β,25-diol, 965. C28H48O3 – 6-Methoxycholest-7-ene-3,5-diol, 795. C28H48O4 – Halicrasterol C, 927. – Nephalsterol A, 971. – Numersterol A, 977. C28H48O8S – (22E,24R,25S)-24-Methyl-5α-cholest-22-ene3β,5,6β, 15α,26-pentol-26-sulfate, 966. – (22E,24S)-24-Methyl-5α-cholest-22-ene3β,5,6β,15α,28-pentol 28-sulfate, 967. C28H48O12S3 – Halistanol sulfate A, 930. – Halistanol sulfate H, 934. C28H50O4 – 24S-Ergostane-3β,5α,6β,7β-tetrol, 913.

480

Index 2 Compound Molecular Formula Index

C28H50O9S – (24R)-24-Methyl-5α-cholestane3β,5,6β,15α,24,28-hexaol 28-sulfate, 963. – (24R,25S)-24-Methyl-5α-cholestane3β,5,6β,15α,16β, 26-hexaol 26-sulfate, 964. C28H50O12S3 – Halistanol sulfate G, 933. C29 C29H34N2O9 – Splenocin C, 354. – Splenocin F, 357. C29H37NO6 – Zampanolide, 592. C29H39NO3 – Antibiotic ML 449, 116. C29H40O4 – Shimalactone A, 622. – Shimalactone B, 623. – Norselic acid A, 1061. C29H40O5 – Kiheisterone A, 1055. – Kiheisterone B, 1056. C29H42O5 – Isogosterone A, 779. – Minabeolide 5, 798. – Streptoseolactone, 818. C29H42O7 – Isogosterone B, 780. C29H44O – Conicasterol B, 873. C29H44O2 – 24-Ethylcholesta-4,24(28)-diene-3,6-dione, 1044. – Petrosterol-3,6-dione, 1106. C29H44O3 – 5,8-Epidioxy-23-methylergosta-6,9(11),22trien-3-ol, 897. – Stoloniferone D, 1108. C29H44O4 – 12β-Acetoxycholest-4-ene-3,24-dione, 646. – 24ξ,25-Epoxy-12β-acetoxycholest-4-en-3-one, 738. – 24ξ,25-Epoxy-23ξ-acetoxycholest-4-en-3-one, 739. – 24ξ-Hydroperoxy-24-ethylcholesta-4,28(29)diene-3,6-dione, 1050. – Norselic acid B, 1062. – Norselic acid D, 1063.

C29H44O5 – Dysideasterol G, 737. – Minabeolide 8, 799. C29H44O6 – 2-O-Acetylpinnasterol, 648. C29H45ClN2O6 – Isomalyngamide A, 70. – Malyngamide A, 76. C29H46O – Dehydroconicasterol, 882. – Stigmasta-4,24(28)-dien-3-one, 1077. C29H46O2 – (24S)-24-Ethyl-3-oxocholesta-4,25-dien-6β-ol, 1048. – 6β-Hydroxy-24-ethylcholesta-4,24(28)-dien3-one, 1053. – Swinhoeisterol A, 1143. C29H46O3 – 5α,8α-Epidioxy-23,24(R)-dimethylcholesta6,22-dien-3β-ol, 896. – (22E)-7α-Methoxy-5α,6α-epoxyergosta-8 (14),22-dien-3β-ol, 960. – Stoloniferone A, 1000. – Stoloniferone B, 1001. – Aragusterol E, 1093. – (3β,5α,8α)-5,8-epi-Dioxy-33-norgorgost-6-en3-ol, 1098. – Swinhoeisterol B, 1144. C29H46O4 – 3α-Acetoxy-25-hydroxycholest-4-en-6-one, 647. – 24ξ-Hydroperoxy-6β-hydroxy-24ethylcholesta-4,28(29)- dien-3-one, 1051. – Aragusterol A, 1090. C29H46O5 – Acalycigorgia inermis sterol A, 642. – 7α,8α-Epoxy-3β-acetoxy-5α,6α-dihydroxycholest-24-ene, 740. – Glaciasterol B 3-acetate, 754. – Hirsutosterol G, 763. – (3β,5α,6α,22E,24ξ)-3,6-Diihydroxy-11acetoxy-27-nor- 9,11-secoergosta-7,22dien-9-one, 890. – (3β,5α,8α,24R)-5,8-Epidioxy-24hydroperoxystigmasta- 6,28-dien-3-ol, 1042. – (3β,5α,8α,24S)-5,8-Epidioxy-24hydroperoxystigmasta -6,28-dien-3-ol, 1043. – (22E)-11-Acetoxy-3β,6α-dihydroxy-9,11-seco -5α- cholesta-7,22-dien-9-one, 1121.

Index 2 Compound Molecular Formula Index

C29H46O6 – Dysideasterol A, 735. – Dysideasterol F, 736. C29H47ClO4 – Aragusterol C, 1092. C29H48ClNO7 – Malyngamide 3, 74. C29H48O – Fucosterol, 1049. – Petrosterol, 1105. C29H48O2 – 15-Dehydroxyconicasterol D, 885. – (24R)-Stigmasta-4,25-diene-3,6-diol, 1076. – 5α,6α-Epoxy-petrosterol, 1099. – 7β-Hydroxypetrosterol, 1102. C29H48O3 – Conicasterol D, 875. – Orostanal, 978. – Stoloniferone C, 1002. – (24S)-24-Ethyl-7α-hydroperoxycholesta-5,25dien-3β-ol, 1046. – (24S)-24-Ethyl-5α-hydroperoxycholesta-6,25dien-3β-ol, 1047. – 24-Hydroperoxy-24-vinylcholesterol, 1052. – Aragusterol B, 1091. – Aragusterol F, 1094. C29H48O4 – Nebrosteroid N, 800. C29H48O4S – Hymenosulfate, 953. C29H48O5 – Acalycigorgia inermis sterol B, 643. – Hirsutosterol D, 762. – (3β,5α,6α)-3,6-Dihydroxy-11-acetoxy-9,11secocholest- 7-en-9-one, 1125. C29H48O7 – Iriomoteolide 4a, 539. C29H48O12S3 – Ibisterol sulfate B, 955. C29H50O3 – Aragusterol G, 1095. – Aragusterol H, 1096. – Aragusterol I, 1097. C29H50O4 – Halicrasterol A, 925. – Nebrosteroid P, 970. C29H50O5 – Punicinol A, 810. – Punicinol B, 811.

481

C29H50O6 – Dendronesterol B, 722. C29H50O9S – Stigmast-25-ene-2,3,15,16,17,18-hexol 2-Osulfate, 1078. C29H51O12PS – Haplosamate A, 935. C29H52O8S – (24R)-24-Ethyl-5α-cholestane-3β,5,6β,15α,29pentol 29-sulfate, 1045. C29H52O12S3 – Halistanol sulfate, 929. C29H52O13S3 – Halistanol sulfate E, 931. C29H52O15P2S – Haplosamate B, 936. C30 C30H22O14 – Daporine, 612. C30H36N2O9 – Splenocin G, 358. C30H40O5 – Minabeolide 2, 1022. C30H42O5 – Paraminabeolide B, 1025. C30H42O6 – Paraminabeolide C, 1026. C30H42O7 – Fijianolide A, 524. – Laulimalide, 541. – Neolaulimalide, 556. C30H44O6 – Amphidinolide E, 402. C30H44O16S3 – Topsentiasterol sulfate B, 1010. C30H45NO11 – Theopederin H, 109. C30H46O – Theonellasterol B, 1079. C30H46O5 – Yonarasterol A, 1016. C30H46O6 – Sinulabasterol, 997. C30H46O7 – (22S)-3α-Acetoxy-11β,18α-dihydroxy-24-methyl18,20β:22,25-diepoxy-5α-furostane, 839. C30H46O15S3 – Topsentiasterol sulfate C, 1011.

482

Index 2 Compound Molecular Formula Index

C30H46O16S3 – Topsentiasterol sulfate A, 1009. C30H47ClN2O7 – Malyngamide R, 91. C30H47NO11 – Theopederin G, 108. C30H48NO10P – 13-Hydroxy-15-O-methylenigmazole A, 532. – 15-O-Methylenigmazole A, 554. C30H48O2 – Theonellasterol C, 1080. – Ketosteroid New, 1138. C30H48O4 – Nephalsterol C, 973. – Malaitasterol A, 1140. C30H48O5 – Hirsutosterol F, 945. – Nebrosteroid O, 969. – Yonarasterol B, 1017. – 6-epi-Yonarasterol B, 1018. – (3β,5α,6α,22Z,24ξ)-3,6-Dihydroxy11-acetoxy-9,11- secoergosta-7, 22-dien-9-one, 1126. – (3β,5α,6α)-3,6-Dihydroxy-11-acetoxy-9,11secoergosta- 7,24(28)-dien-9-one, 1127. – Hirsutosterol B, 1130. C30H48O6 – 3-Acetyl-22-epi-hippuristanol, 842. – Anicequol, 866. – Dysideasterol H, 895. C30H48O6S – Annasterol sulfate, 867. C30H48O7 – 3-Acetyl-2-desacetyl-22S-epi-hippurin 1, 840. – 3-Acetyl-2-desacetyl-22R-epi-hippurin 1, 841. – Hippurin 1, 847. – 22-epi-Hippurin 1, 848. C30H48O8S – Acanthosterol sulfate I, 859. – Acanthosterol sulfate J, 860. C30H48O14S3 – Topsentiasterol sulfate D, 1012. C30H50O – Remeisterol, 994. C30H50O2 – 15-Dehydroxyconicasterol C, 884. – 7α-Hydroxytheonellasterol, 1054. – Topsentinol B, 1087.

C30H50O3 – Conicasterol C, 874. – Theonellasterol E, 1082. – Theonellasterol F, 1083. – Theonellasterol K, 1086. C30H50O4 – Theonellasterol G, 1084. – Theonellasterol H, 1085. – (3β,24ξ)-3,11,24-Trihydroxy-9,11-secogorgost5-en-9-one, 1110. – 3β-Hydroxy-5α,6α-epoxy-9-oxo-9,11-secogorgostan-11-ol, 1131. C30H50O5 – Halicrasterol D, 928. – Hirsutosterol E, 944. – 5,6-Epoxy-1,3,11-trihydroxy-9,11-secogorgostan-9-one, 1100. – 3β,7β,11-Trihydroxy-5α,6α-epoxy-9,11-secogorgostan-9-one, 1109. – Hirsutosterol A, 1129. C30H50O6 – Penicisteroid A, 991. C30H50O12S3 – Ibisterol C, 954. C30H51BrO6 – Saiyacenol A, 36. – Saiyacenol B, 37. C30H52O2 – (3β,5α,24R)-Ergost-7-en-3-ol methoxymethyl ether, 917. C30H52O3 – (3β,4α,5α,22E,24R)-3,11-Dihydroxy-4,23dimethyl-9,11- secoergost-22-en-9-one, 1128. – Lobophytosterol‡, 1139. C30H52O4 – 9,11-Seco-24-hydroxydinosterol, 996. C30H52O5 – (3β,5α,6β,24ξ)-Ergostane-3,5,6,25-tetrol 25acetate, 914. C30H52O6 – Levantilide A, 542. C30H52O10S2 – Weinbersteroldisulfate A, 1111. C30H53O9P – Desulfohaplosamate, 887. C30H54O12S3 – Halistanol sulfate F, 932.

Index 2 Compound Molecular Formula Index

C31 C31H30N2O9 – Splenocin I, 360. C31H38N2O9 – Splenocin H, 359. C31H42O5 – Norselic acid E, 1064. C31H44Br2O10 – 17,19-Dibromooscillatoxin A, 248. C31H44O7 – Isogosterone D, 782. C31H44O10 – 31-Noroscillatoxin B, 254. C31H45BrO10 – 17-Bromooscillatoxin A, 246. C31H46O7 – Amphidinolide A, 390. C31H46O8 – Isogosterone C, 781. C31H46O10 – Oscillatoxin A, 255. C31H47NO11 – Theopederin L, 113. C31H48O5 – Yonarasterol C, 1112. C31H48O6 – 3α,11α-Diacetoxy-25-hydroxycholest-4-en- 6one, 725. C31H49BrO10 – Lyngbyaloside, 545. C31H49O12S3 – Ibisterol sulfate, 1103. C31H50O5 – Hirsutosterol C, 1101. C31H50O6 – Agosterol C, 651. C31H50O7 – Agosterol B, 650. – Hipposterone N, 1135. C31H50O8 – Blancasterol, 671. C31H51NO10 – Onnamide F, 98. C31H52O3 – Theonellasterol D, 1081. C31H52O5 – Aragusteroketal A, 1088. C31H52O6 – Cholestane-3α,6α-Diacetoxy-22S,25-diol, 679.

483

– Halicrasterol B, 926. C31H52O7 – Iriomoteolide 5a, 540. C31H52O10 – Lyngbouilloside, 544. C31H52O13S3 – Topsentiasterol sulfate E, 1013. C31H53ClO5 – Aragusteroketal C, 1089. C31H53NO6 – Tulearin A, 591. C31H55NO6 – Malyngamide E, 81. C31H56O12S3 – Ophirapstanol trisulfate, 803. C31H57NO7 – Malyngamide D, 80.

C32 C32H38O13 – Lustromycin, 543. C32H38O14 – Orbuticin, 559. C32H38O15 – Antibiotic BK 223B, 486. C32H46Br2O10 – 19-Bromoaplysiatoxin, 245. C32H46O7 – Lasonolide D, 442. C32H46O9 – Anhydrodebromoaplysiatoxin, 243. C32H46O10 – Oscillatoxin B1, 256. – Oscillatoxin B2, 257. C32H47BrO10 – Aplysiatoxin, 244. – Manauealide B, 250. C32H47ClO10 – Manauealide A, 249. C32H48O9 – (22S)-2α,3α-Diacetoxy-11β,18α-dihydroxy-24methyl- 18,20β:22,25-diepoxy-5αfurostane, 846. C32H48O10 – Debromoaplysiatoxin, 247. C32H49NO11 – Theopederin I, 110. – Theopederin K, 112.

484

Index 2 Compound Molecular Formula Index

C32H50O7 – Amphidinolide B4, 394. – Amphidinolide B5, 395. C32H50O8 – Amphidinolide B, 391. – Amphidinolide B2, 392. – Amphidinolide B3, 393. – Amphidinolide D, 401. – Amphidinolide G1, 404. – Amphidinolide G2, 405. – Amphidinolide H1, 407. – Amphidinolide H2, 408. – Amphidinolide H3, 409. – Amphidinolide L, 414. C32H50O9 – Formosalide A, 4. C32H50O10 – 13-Deoxytedanolide, 517. C32H50O11 – Tedanolide, 589. C32H50O13 – Precandidaspongiolide A, 572. – Precandidaspongiolide B, 573. C32H52O2 – Acetyltheonellasterol, 1035. C32H52O6 – Dictyostatin, 518. – Hippuristerone D, 943. C32H52O7 – Amphidinolide B7, 397. – Acanthifolioside C, 645. – Orthohippurinsterone A, 981. C32H52O8 – Amphidinolide G3, 406. – Amphidinolide H4, 410. – Amphidinolide H5, 411. C32H54O6 – Hippuristerol D, 940. C32H54O7 – Orthohippurinsterol A, 979. – Orthohippurinsterol B, 980. C32H54O8 – Amphidinolactone B, 389. – Amphidinolide B6, 396. C32H56O8 – Rathbunioside R1, 812. C32H56O9 – Rathbunioside R2, 813.

C32H56O11S – Amurensoside A, 658. C33 C33H40O14 – Calcaride A, 498. C33H40O15 – Calcaride B, 499. – Calcaride C, 500. C33H42O15 – Calcaride E, 501. C33H43NO9 – Salinisporamycin, 115. C33H46O9 – Lasonolide F, 444. C33H48N2O7 – Palmerolide A, 562. C33H49BrO10 – 3-Methoxyaplysiatoxin, 252. C33H49ClO10 – Phorbaside A, 305. C33H49NO5 – Halichomycin, 27. C33H50O10 – 3-Methoxydebromoaplysiatoxin, 253. – Pandaroside D, 806. C33H52O6 – Hippuristerone B, 942. C33H52O7 – Acanthifolioside A, 857. – Hippuristerone A, 941. C33H52O8 – Agosterol A, 649. – Agosterol D2, 652. – Agosterol C6, 1039. – Hipposterone M, 1134. C33H52O9 – Formosalide B, 5. C33H52O11 – Amphidinolide N, 416. – Caribenolide I, 507. C33H53NO7 – Nocardiopsin B, 388. C33H53NO9 – Malyngamide J, 85. C33H54O6 – Hippuristerol B, 939.

Index 2 Compound Molecular Formula Index

C33H54O7 – Acanthifolioside B, 858. – Hippuristerol A, 938. C33H56O10 – Linckoside Q, 958. C33H56O11S2 – Orthoesterol C disulfate, 1023. C33H56O12S – Asteriidoside L, 869. C33H57N3O7 – Malyngamide X, 92. C33H58O8 – Linckoside L2, 789. C33H58O10 – Linckoside L1, 788. C33H58O12S – Phrygioside B, 808. C34 C34H38O4 – Amphidinolide R, 420. C34H43NO9 – Tamulamide B, 210. C34H46O5 – Tetromycin B, 331. C34H48ClNO10 – Phorbaside D, 307. C34H49ClO10 – Callipeltoside C, 504. C34H50O7 – Amphidinolide U, 427. C34H50O11 – Manauealide C, 251. C34H51NO8 – Leiodermatolide, 317. C34H51NO11 – Theopederin J, 111. C34H52O8 – Agosterol A4, 864. C34H52O9 – Biselyngbyaside, 493. C34H52O10 – Pandaroside D methyl ester, 807. C34H52O14 – Candidaspongiolide A, 505. – Candidaspongiolide B, 506. C34H54O10 – Biselyngbyaside B, 494. – Mandelalide A, 547.

485

C34H54O14S – Downeyoside A, 893. – Downeyoside B, 894. C34H56O6 – 24-Methylenecholesterol-5-ene-3β,16β-diol3-O-α-L- fucopyranoside, 968. C34H56O7 – Sinularoside A, 998. C34H56O8 – Acodontasteroside I, 1038. C34H56O10 – Leviusculoside J, 1020. C34H59NO9 – 5-Hydroxymethyl-discodermolate, 28. C35 C35H32O2 – 23-Norspiculoic acid B, 621. C35H45NO9 – Tamulamide A, 209. C35H46N2O12 – Salarin A, 576. C35H48ClNO10 – Callipeltoside A, 502. C35H50ClNO10 – Callipeltoside B, 503. C35H50O9 – Lasonolide E, 443. C35H51NO7 – Amphilactam A, 482. – Amphilactam C, 484. C35H52O9 – Amphidinolide F, 403. C35H54O8 – Agosterol A5, 865. C35H54O10 – Hipposterone O, 1136. C35H56O8 – Bafilomycin D, 309. C35H56O9 – Hipposterol G, 1133. C35H58O6 – Pakisterol A, 1065. C35H58O9 – Hippuristeroketal A, 1137. C35H60O8 – Acanthifolioside E, 1033. C35H62O8 – Acanthifolioside D, 1032.

486

Index 2 Compound Molecular Formula Index

C36 C36H50N2O6 – Superstolide B, 587. C36H50N2O13S3 – Amaranzole C, 654. – Amaranzole D, 655. C36H52N2O7 – Superstolide A, 586. C36H53NO7 – Amphilactam B, 483. – Amphilactam D, 485. C36H54O12 – Miyakolide, 385. C36H56O7 – Bafilomycin I, 312. C36H58O8 – Crassarosteroside A, 877. – Crassarosteroside B, 878. – Crassarosteroside C, 879. – Sinularoside B, 999. C36H58O9 – Fragilioside A, 751. – Fragilioside B, 752. C36H60O9 – Bafilomycin G, 311. C36H60O10 – Riisein A, 814. – Riisein B, 815. C36H62O10 – Sanguinoside C, 995. C37 C37H44O14 – Grincamycin C, 123. C37H45NO12 – Rifamycin S, 114. C37H50N2O15S3 – Amaranzole E, 656. – Amaranzole F, 657. C37H52N2O15S3 – Amaranzole B, 653. C37H56O8 – Micromonospolide C, 320. C37H58O9 – Micromonospolide B, 319. C37H58O13 – Mandelalide B, 548. C37H59N5O12 – 17-Oxoonnamide B, 100.

C37H61N5O12 – Onnamide B, 95. C37H62O14 – Asteriidoside F, 664. C37H62O17S – Asteriidoside I, 665. C37H64O13 – Mediasteroside M2, 792. C37H68N4O4S – 24-Desulfo-24-ketone-26-[(2-amino-2carboxyethyl)lthio]- squalamine, 724. C37H72N4O5S – Nω-(3-Aminopropyl)-squalamine, 801. C38 C38H55NO11 – Lituarine C, 191. C38H55NO8S – Polymastiamide A, 992. C38H55NO9 – Lituarine A, 189. C38H61N5O12 – 15-De-O-methylonnamide, 67. C38H62O11 – Carijoside A, 672. C38H62O13 – Dimorphoside A, 732. – Wondosterol B, 821. – Wondosterol C, 822. C38H63N5O11 – Onnamide D, 97. C38H66O13 – Mediasteroside M1, 791. C38H66O14 – Kurilensoside D, 786. C39 C39H56O14 – Pandaroside E, 983. C39H58O14 – Pandaroside F, 985. C39H58O15 – Bryostatin 11, 377. C39H60O15 – Pandaroside C, 804. C39H61N5O12 – 11-Oxoonnamide A, 99. C39H61N5O14 – Onnamide C, 96.

Index 2 Compound Molecular Formula Index

C39H62O11 – Brevisin, 157. C39H63N5O12 – 6,7-Dihydro-11-oxoonnamide A, 69. – 4Z-Onnamide A, 93. – Onnamide A, 94. C39H64O11 – Bahamaolide A, 117. C39H64O12 – Acodontasteroside H, 863. C39H64O13 – Wondosterol A, 1015. C39H64O14 – Linckoside M, 957. C39H65N5O12 – 6,7-Dihydroonnamide A, 68. C39H66O14 – Acodontasteroside E, 861. – Acodontasteroside G, 862. C39H66O15S2 – Clathsterol, 1041. C39H68O11 – Dolabelide D, 523. C39H68O13 – Crossasteroside B, 720. – Halityloside F, 759. – Mediasteroside M3, 793. – Mediasteroside M4, 794. C39H68O14 – Crossasteroside A, 719. – Acodontasteroside D, 1036. C40 C40H57NO12 – Lituarine B, 190. C40H58N2O7 – Iejimalide A, 535. C40H58N2O10S – Iejimalide C, 537. C40H58O14 – Pandaroside E methyl ester, 984. C40H60BO141– Aplasmomycin A, 487. C40H60O14 – Pandaroside F methyl ester, 986. – Pandaroside G, 1068. C40H61ClO14 – Phorbaside C, 306. – Phorbaside E, 308.

C40H62O14 – Pandaroside H, 1070. C40H64O12 – Nonactin, 48. C40H66O12 – Eryloside A, 746. C40H66O14 – Linckoside N, 1058. – Linckoside O, 1059. – Linckoside P, 1060. C40H66O15 – Pandaroside C methyl ester, 805. C40H66O17S – Linckoside L7, 1057. C40H70O14 – Acodontasteroside F, 1037. C41 C41H59NO7 – 13,19-Didemethylspirolide C, 216. – Iejimalide B, 536. C41H60N2O10S – Iejimalide D, 538. C41H60O9 – Lasonolide A, 440. C41H60O10 – Amphidinolide C3, 400. – Lasonolide C, 441. C41H60O15 – Neristatin I, 557. C41H60O17 – Bryostatin 7, 373. C41H61NO9 – Pinnatoxin A, 229. C41H62O10 – Amphidinolide C, 398. C41H62O14 – Pandaroside G methyl ester, 1069. C41H62O15 – Bryostatin 13, 379. – Pandaroside J, 1074. C41H64O14 – Pandaroside H methyl ester, 1071. – Pandaroside I, 1072. C41H64O15 – Pandaroside A, 1066. C41H69BrO11 – Oscillariolide, 560.

487

488

Index 2 Compound Molecular Formula Index

C41H70O12 – Dolabelide B, 521. C42 C42H48O12 – Trisorbicillinone D, 304. C42H48O13 – Trisorbicillinone A, 301. – Trisorbicillinone B, 302. – Trisorbicillinone C, 303. C42H49NO12 – Sorbicillamine D, 293. C42H61NO7 – 13-Demethylspirolide C, 214. – Spirolide A, 236. – Spirolide G, 242. C42H62BO151– Aplasmomycin B, 488. C42H62O14 – Bryostatin 16, 382. – Bryostatin 17, 383. C42H63NO8 – Spirolide E, 240. C42H64NO71+ – Spirolide B, 237. C42H64N2O9 – Pinnatoxin B, 230. – Pinnatoxin C, 231. C42H64O15 – Bryostatin 10, 376. – Bryostatin 18, 384. – Pandaroside J methyl ester, 1075. C42H64O16 – Bryostatin 14, 380. C42H65NO8 – Spirolide F, 241. C42H65NO13S – Bafilomycin F, 310. C42H66O14 – Pandaroside I methyl ester, 1073. C42H66O15 – Polycavernoside A2, 568. – Pandaroside A methyl ester, 1067. C42H66O24S3 – Adriatoxin, 145. C42H68O13 – Maduralide, 546.

C42H69NO13S – Spiroprorocentrimine, 578. C42H72O16 – Cyanolide A, 3. C42H80O11 – Caylobolide B, 509. C42H82O11 – Caylobolide A, 508. C43 C43H50O16 – Grincamycin D, 124. C43H60O12 – Goniodomin A, 525. C43H63NO7 – 20-Methylspirolide G, 223. – Spirolide C, 238. C43H64O11 – Gambierol, 168. – Amphidinolide C2, 399. C43H64O17 – Bryostatin 6, 372. – Bryostatin 9, 375. C43H66NO71+ – Spirolide D, 239. C43H66O9 – Amphidinolide M, 415. C43H68O15 – Polycavernoside A, 567. – Polycavernoside B2, 571. C43H72O13 – Dolabelide A, 520. – Dolabelide C, 522. C43H74O10 – Neomaclafungin E, 55. C43H74O21S – Kurilensoside A, 783. C44 C44H58O17S – Urdamycin E, 130. C44H64BO151– Aplasmomycin C, 489. C44H66O17 – Bryostatin 5, 371. C44H68BO141– Borophycin, 496.

Index 2 Compound Molecular Formula Index

C44H68O12 – 7-Deoxyokadaic acid, 215. C44H68O13 – Dinophysistoxin 2, 219. – Okadaic acid, 224. – 19-epi-Okadaic acid, 225. C44H68O13S – Acanthifolicin, 213. C44H68O14 – Tartrolone D, 588. C44H70O15 – Polycavernoside A3, 569. C44H73NO11 – 19-O-DemethylscytophycinC, 515. C44H76O4 – (22E)-Ergosta-7,22-diene-6αhexadecanooxyl-3β,5α-diol, 904. – (22E)-Ergosta-7,22-diene-6βhexadecanooxyl-3β,5α-diol, 905. C44H76O10 – Neomaclafungin F, 56. C44H76O11 – Neomaclafungin A, 51. C44H76O19 – Kurilensoside B, 784. – Kurilensoside C, 785. C45 C45H66O16 – Bryostatin 2, 367. C45H67NO5 – Gymnasterone A, 921. C45H67NO10 – Pinnatoxin D, 232. C45H68O17 – Bryostatin 8, 374. C45H70N2O10S – Pteriatoxin A, 233. – Pteriatoxin B, 234. – Pteriatoxin C, 235. C45H70O13 – Dinophysistoxin 1, 218. C45H70O16 – Polycavernoside B, 570. C45H70O18 – Sepositoside A, 816.

489

C45H72O13 – 14,15-Dihydrodinophysistoxin 1, 217. C45H73NO13 – 6-Hydroxyscytophycin B, 534. C45H75NO12 – Scytophycin E, 577. C45H78O10 – Neomaclafungin G, 57. – Neomaclafungin H, 58. C45H78O11 – Neomaclafungin B, 52. – Neomaclafungin C, 53. C46 C46H64O17 – 20-epi-Bryostatin 3, 368. – Bryostatin 3, 369. C46H65NO13 – Micromonospolide A, 318. C46H70O17 – Bryostatin 4, 370. C46H75NO13 – Tolytoxin, 590. C46H76O4 – (22E)-Ergosta-7,22-diene-6α-9Z,12Zoctadecadienooxyl- 3β,5α-diol, 906. C46H77NO13 – 6-Hydroxy-7-O-methylscytophycin E, 533. C46H78O4 – (22E)-Ergosta-7,22-diene-6α-9Zoctadecenooxyl-3β,5α-diol, 909. C46H80O4 – (22E)-Ergosta-7,22-diene-6β-octadecanooxyl3β,5α-diol, 907. – (22E)-Ergosta-7,22-diene-6α-octadecanooxyl3β,5α-diol, 908. C46H80O10 – Neomaclafungin I, 59. C46H80O11 – Neomaclafungin D, 54. C46H80O12 – Maclafungin, 50.

C47 C47H58O10 – asperversin A, 868.

490

Index 2 Compound Molecular Formula Index

C47H68O14 – (36R)-Pectenotoxin 12, 453. – (36S)-Pectenotoxin 12, 454. C47H68O15 – Pectenotoxin 3, 448. C47H68O16 – Pectenotoxin 6, 450. – Pectenotoxin 7, 451. C47H68O17 – Bryostatin 1, 366. C47H68O18 – Bryostatin 15, 381. C47H70O14 – Pectenotoxin 2, 447. C47H70O15 – Pectenotoxin 1, 446. – Pectenotoxin 4, 449. – Pectenotoxin 11, 452. C47H80O19 – Acanthifolioside F, 1034. C47H82O6 – 21-O-Octadecanoyl-xestokerol A, 1104. C48 C48H64O19S – Acuminolide A, 480. C48H68N2O15 – Lobophorin I, 326. C49 C49H60O17 – Grincamycin E, 125. C49H62O14 – Tetromycin 3, 329. – Tetromycin 4, 330. C49H62O18 – Grincamycin A, 121. – Grincamycin B, 122. C49H69ClO14 – Brevetoxin PbTx8, 156. C49H70O13 – Brevetoxin A, 146. C49H72O13 – Brevetoxin PbTx7, 155. C49H72O17 – Bryostatin 12, 378. C49H75NO17 – Belizentrin, 492.

C50 C50H64O14 – Tetromycin 2, 328. C50H65NO13 – Tetromycin 1, 327. C50H70O14 – Brevetoxin B, 147. C50H70O15 – Brevetoxin PbTx6, 154. C50H72O14 – Dihydrobrevetoxin B, 162. C50H82O15 – Halichoblelide C, 316. C51 C51H69N15O18 – Streptobactin, 362. C51H71N15O19 – Tribenarthin, 363. C51H75NO17S – Brevetoxin B2, 149. C51H84O15 – Halichoblelide B, 315. C52 C52H72O15 – Brevetoxin PbTx5, 153. C52H75NO17S – Brevetoxin B1, 148. C52H78O21S2 – 45,46,47-Trinoryessotoxin, 211. C52H84O14 – Reidispongiolide C, 460. C52H84O15 – Sphinxolide G, 467. C52H84O16 – Sphinxolide F, 466. C53 C53H82O11 – Lasonolide G, 445. C53H82O14 – Okadaic acid 7-hydroxy-2,4-dimethyl-2E,4Eheptadienyl ester, 226. – Okadaic acid 7-hydroxy-4-methyl-2-methylene-4E-heptenyl ester, 227. C53H85NO13 – Reidispongiolide B, 459.

Index 2 Compound Molecular Formula Index

C53H85NO14 – Sphinxolide B, 462. C53H90N2O12 – Aplyronine C, 434. C54 C54H87NO13 – Reidispongiolide A, 458. C54H87NO14 – Sphinxolide D, 464. C54H87NO15 – Sphinxolide A, 461. C54H88O22S5 – Fibrosterol sulfate B, 749. C54H94O16 – Antibiotic IB 96212, 49. C55 C55H80O18 – Gymnocin A, 169. – Gymnocin A2, 170. C55H82O18S – 1-Desulfoyessotoxin, 161. C55H82O21S2 – Yessotoxin, 212. C55H82O22S2 – 45-Hydroxyyessotoxin, 186. C55H88O18 – Halichoblelide A, 314. C55H88O31S – Astrosterioside C, 626. C55H89NO15 – Sphinxolide C, 463. C55H89NO16 – Sphinxolide E, 465. C55H90O18S4 – Fibrosterol sulfate C, 750. C55H90O20S5 – Manadosterol A, 854. – Manadosterol B, 855. C55H90O27S – Ophidianoside F, 802. C56 C56H76O17 – Halichondrin B-1020, 173. C56H84O16S3 – Shishicrellastatin B, 1142. C56H84O21S2

– Protoceratin I, 203. C56H85NO13 – Prorocentrolide, 574. C56H85NO17S – Prorocentrolide B, 575. C56H86O16S3 – Shishicrellastatin A, 1141. C56H87NO13 – Dihydroprorocentrolide, 519. C56H90O15 – 11ʹ,12ʹ-Dehydroelaiophylin, 313. C56H90O29S – Astrosterioside D, 826. C56H92O27S – Lethasterioside A, 787. C56H92O28S – Thornasteroside A, 819. C57 C57H66O20 – Grincamycin F, 126. C57H82O16 – Pacific ciguatoxin 3C, 201. C57H82O17 – 51-Hydroxyciguatoxin 3C, 185. C57H84O18 – 2,3-Dihydro-2,3-dihydroxyciguatoxin 3C, 163. C57H92O27S – Goniopectenoside C, 757. – Marthasteroside B, 790. C57H92O28S – Goniopectenoside A, 755. C57H94O27S – Goniopectenoside B, 756. C57H96O27S – Archasteroside B, 660. C58 C58H76O14 – Marinomycin A, 550. – Marinomycin B, 551. – Marinomycin C, 552. C58H88O10S – Crellastatin D, 714. C58H88O11S – Crellastatin B, 712. – Crellastatin C, 713. – Crellastatin E, 715.

491

492

Index 2 Compound Molecular Formula Index

C58H88O12S – Crellastatin A, 711. C58H90O15S2 – Crellastatin G, 717. – Crellastatin H, 718. C58H90O16S2 – Crellastatin F, 716. C58H96O27S – Diplasterioside A, 734. C58H96O28S – Regularoside A, 993. C58H99N3O14 – Aplyronine D, 435. – Aplyronine F, 437. – Aplyronine G, 438. – Aplyronine H, 439. C59 C59H78O14 – Marinomycin D, 553. C59H80O18 – Halichondrin B-1076, 174. C59H82O19 – Norhalichondrin B, 197. C59H82O20 – Norhalichondrin C, 198. C59H82O21 – Norhalichondrin A, 196. C59H84O20 – Neonorhalichondrin B, 195. C59H89ClO19 – Spongistatin 5, 583. C59H92O16 – Gambieric acid A, 164. C59H93NO8 – 17-O-Palmitoyl-20-methylspirolide G, 228. C59H97BrO12 – Phormidolide, 566. C59H98O27S – Diplasterioside B, 892. C59H98O28S – Archasteroside A, 1040. C59H101N3O14 – Aplyronine A, 432. – Aplyronine B, 433. C60 C60H84O16 – Pacific ciguatoxin 4B, 202. C60H86O18

– Pacific ciguatoxin 2, 200. C60H86O19 – Halichondrin B, 172. – Pacific ciguatoxin 1, 199. C60H86O20 – Halichondrin C, 177. – Halistatin 1, 178. C60H94O16 – Gambieric acid B, 165. C60H98O30S – Hippasterioside D, 833. C60H100O23S – Symbiopolyol, 142. C60H102O25S – Luteophanol A, 31. C60H103N3O14 – Aplyronine E, 436. C61 C61H85ClO18 – Halichondrin B-1140, 176. C61H86O17 – Halichondrin B-1092, 175. C61H86O19 – Homohalichondrin B, 183. – Isohomohalichondrin B, 187. – 38-epi-Isohomohalichondrin B, 188. C61H86O20 – Halistatin 2, 179. – Homohalichondrin C, 184. C61H86O21 – Homohalichondrin A, 182. C61H87N2O20 – Lobophorin H, 325. C61H88O19 – Halistatin 3, 180. C61H90N2O21 – Lobophorin B, 323. C61H91ClO20 – Spongistatin 9, 585. C61H92N2O19 – Lobophorin A, 322. C61H92O20 – Spongistatin 8, 584. C61H92O25S2 – Protoceratin III, 205. C61H93ClO20 – Spongistatin 3, 581. – Spongistatin 4, 582.

Index 2 Compound Molecular Formula Index

C61H98O31S – Astrosterioside A, 670. C61H100O30S – Hippasterioside B, 761. C61H100O31S – Asteriidoside E, 663. C62 C62H88O19 – 53-Methoxy-neoisohomohalichondrin B, 193. – 55-O-Methylisohomohalichondrin B, 194. C62H92O19 – Caribbean ciguatoxin 1, 159. – Caribbean ciguatoxin 2, 160. C62H92O20 – Gymnocin B, 171. C62H102O31S – Asteriidoside C, 662. – Hippasterioside A, 937. C62H104O20S – Colopsinol C, 8. C63 C63H84N2O20 – Lobophorin G, 324. C63H95BrO21 – Altohyrtin B, 481. C63H95ClO21 – Spongistatin 1, 579. C63H96O21 – Spongistatin 2, 580. C63H104O33S – Asteriidoside A, 661. – PectiniosideB, 990. C63H109N3O17 – Azalomycin F4a 2-ethylpentyl ester, 386. C63H110O24S – Amphidinol 17, 137.

C65H101NO27S2 – Dinophysistoxin 5a, 221. C65H110O20S – Colopsinol E, 9. C66 C66H100O17 – Brevetoxin B3b, 151. C66H100O29S2 – Protoceratin II, 204. C66H102O19 – Gambieric acid D, 167. C66H103NO27S2 – Dinophysistoxin 5b, 222. C66H104O30S3 – Dinophysistoxin 4, 220. C67 C67H112N2O23 – Ostreol A, 17. C68 C68H114O34 – Prorocentrol, 18. C68H123ClO24 – (64E)-Chloro-KmTx3, 139. C68H124O24 – KmTx3, 140. C68H124O27S – 10-O-Sulfo-KmTx3, 144. C69 C69H109NO18S – Brevetoxin B4b, 152. C69H122O25 – Lingshuiol, 30. C69H125ClO24 – (65E)-chloro-KmTx1, 138. C69H126O27S – 10-O-Sulfo-KmTx1, 143.

C64 C64H96O17 – Brevetoxin B3a, 150. C64H111N3O17 – Azalomycin F5a 2-ethylpentyl ester, 387.

C70 C70H120O24 – Amphidinol 6, 136.

C65 C65H100O19 – Gambieric acid C, 166.

C71 C71H108O33S2 – Protoceratin IV, 206.

493

494

Index 2 Compound Molecular Formula Index

C72 C72H120O25S – Colopsinol A, 7. C72H122O24 – Amphidinol 5, 135. C73 C73H126O20 – Bistheonellide B, 471. C73H126O27S – Amphidinol 1, 133. C73H132O28 – Karatungiol A, 29. C74 C74H128O20 – Bistheonellide A, 470. C76 C76H123N3O22 – Mirabalin, 555. C76H130O20 – Hurghadolide A, 472. C77 C77H122O25 – Amphidinol 2, 134. C77H130O20 – Swinholide B, 475. – Swinholide C, 476. C78 C78H129N3O20 – Poecillastrin C, 457. C78H132O20 – Isoswinholide A, 473. – Swinholide A, 474. C78H132O21 – Swinholide I, 478. – Swinholide K, 479. C79 C79H131N3O20 – Poecillastrin A, 455. – Poecillastrin B, 456. C80 C80H136O20 – Swinholide H, 477.

C81 C81H131N3O23 – Chondropsin C, 511. C81H132O20 – Belizeanolide, 491. C81H134O21 – Belizeanolic acid, 24. C83 C83H133N3O25 – 73-Deoxychondropsin A, 516. C83H133N3O26 – Chondropsin A, 510. – Chondropsin D, 512. C90 C90H152O28 – Ankaraholide A, 468. C91 C91H154O28 – Ankaraholide B, 469. C96 C96H136Cl3NO44 – Prymnesin 2, 208. C107 C107H154Cl3NO44 – Prymnesin 1, 207. C107H160O38 – Brevisulcenal F, 158. C127 C127H219N3O53 – Ostreocin D, 141. C129 C129H223N3O54 – Palytoxin, 132. C132 C132H228N2O51 – Vatoxin-a, 45. C137 C137H233NO57S – Symbiodinolide, 118.

Index 2 Compound Molecular Formula Index

C138 C138H231NO56S – Zooxanthellatoxin B, 594. C140 C140H233NO57S – Zooxanthellatoxin A, 593.

C164 C164H258O68S2 – Maitotoxin (MTX), 192.

495

Index 3 Compound Organism Source Index This index lists in alphabetical order all 585 marine organism in Latin names in HAMNP Volume 5, 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 283 of this index, one will know that the Haliclona sp. is a sponge. A Acabaria undulata 740, 742, 827, 898. Acalycigorgia inermis 642, 643, 644. Acanthaster planci 819. Acanthodendrilla sp. 859, 860. Acanthophora spicifera 337, 338, 339, 340. Acanthus ebracteatus 949. Acantophora spicifera 694. Acarnus sp. 440. Acodontaster conspicuus 698, 861, 862, 863, 911, 1036, 1037, 1038. Acremonium sp. 595, 597, 605, 607. Acrostichum speciosum 904, 905, 906, 907, 908, 909, 947, 960. Actinoalloteichus sp. 51, 52, 53, 54, 55, 56, 57, 58, 59. Agelas dispar 297, 298, 299, 796. Agelas flabelliformis 796. Agelas gracilis 12, 13. Agelas oroides 796. Aigialus parvus BCC 5311 332, 333, 334, 341. Aka sp. 929. Alcyonium gracillimum 635, 636, 638, 727, 741, 851, 852. Alcyonium patagonicum 903. Aldisa sanguinea cooperi 639. Alexandrium hiranoi 525. Alexandrium ostenfeldii 214, 216, 223, 228, 236, 237, 238, 239, 240, 241, 242. Alpysilla glacialis 830. Amanthia convolute 372. Amathia convoluta 366, 367, 370, 371, 373, 374. Amphidinium carterae 137. Amphidinium klebsii 133, 134, 135, 136. Amphidinium sp. 20, 21, 29, 30, 142, 391, 392, 393, 394, 395, 396, 397, 398, 399, 401, 402, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 420, 421, 423, 424, 425, 426, 427, 428, 431, 539.

Amphidinium sp. S1-36-5 507. Amphidinium sp. Y-25 389. Amphidinium sp. Y-42 429, 430. Amphidinium sp. Y-5 7, 8, 9, 390, 419. Amphidinium sp. Y-52 31. Amphidinium sp. Y-56 400, 422. Amphidinium spp. Y-25 394. Amphimedon sp. 482, 483, 484, 485. Amphiscolops magniviridis 403. Amphiscolops sp. 390, 400, 401, 402, 404, 407, 412, 413, 414, 417, 422, 426, 427, 429, 593, 594. Analipus japonicus 362, 363. Annella sp. 497, 514. Antedon bifida 982. Anthelia glauca 913. Anthoplexaura dimorpha 732. Antipathes subpinnata 676, 701, 703, 726. Aphelasterias japonica 629, 708. Apis mellifer 696. Aplidium californicum 370, 371. Aplysia juliana 705, 795. Aplysia kurodai 432, 433, 434, 435, 436, 437, 438, 439. Aplysia vaccaria 101. Aplysina aerophoba 604. Archaster typicus 660, 993, 1040. Arthasterias glacialis 709. Ascidia nigra 891. Aspergillus aculeatus HTTM-Z07002 949. Aspergillus awamori 904, 905, 906, 907, 908, 909, 947, 960. Aspergillus niger 261, 267, 897, 974, 975. Aspergillus sp. 596, 599. Aspergillus sp. MF-93 259. Aspergillus sulphureus 598. Aspergillus sydowi YH11-2 836, 871. Aspergillus ustus cf-42 956. Aspergillus versicolor 260, 262, 263, 266, 868, 871, 891.

Index 3 Compound Organism Source Index

Aspergillus versicolor MF359 258, 260, 264, 265. Aspergillus versicolor ZBY-3 1014. Asterias amurensis 658. Asterias amurensis cf. versicolor 819. Asterias forbesi 629. Asterias pectinifera 709. Asterias rathbuni 658, 728, 812, 813. Asterias rubens 709. Asterina pectinifera 990. Astrogorgia sp. 1113. Astropecten monacanthus 626, 670, 826. Astropecten polyacanthus 666, 667, 668, 669. Austrovenus stutchburyi 148. Avicennia mariana 351. Avicennia marina 974, 975. Axinella cannabina 891, 918. Axinella carteri 178, 179, 183. Axinella polypoides 327, 328, 329, 330, 331. Axinella sp. 182. Axinella spp. 172. B Bathyplotes natans 709. Biemna sp. 870. Bifurcaria sp. 1049. Bugula neritina 366, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 379, 380, 381, 382, 383, 384, 557. Bugula sp. 22, 23, 883, 888, 889, 891, 896, 897, 948, 950, 951, 952. Bulla gouldiana 35. Bulla occidentalis 34, 35. Bursatella leachii 92. C Cacospongia mycofijiensis 592. Calcarisporium sp. 498, 499, 500, 501. Calicogorgia sp. 1114, 1115. Callipelta sp. 502, 503, 504. Candidaspongia sp. 505, 506, 572, 573, 589. Capnella thyrsoidea 628, 630. Capsosiphon fulvescens 982. Caranx latus 159, 160. Carijoa sp. 672. Ceratodictyon spongiosum 119. Chainia spp. 120. Chlorella ellipsoidea 918. Chondropsis sp. 510, 512.

497

Chromodoris lochi 524. Cinachyra sp. 582. Cinachyrella enigmatica 532, 554. Cinachyrella sp. 1132. Ciona intestinalis 1052. Cladiella hirsuta 762, 763, 944, 945, 1101, 1129, 1130. Clathria sp. 1041. Clavularia viridis 1000, 1001, 1002, 1003, 1004, 1005, 1006, 1007, 1008, 1016, 1017, 1019, 1108, 1112. Cliona copiosa 775. Cochliobolus lunatus 321. Codium arabicum 1046, 1047, 1048. Coscinasterias tenuispina 790. Cosmasterias lurida 802. Crassostrea gigas 229, 232. Crella sp. 711, 712, 713, 714, 715, 716, 717, 718, 976, 1061, 1062, 1063, 1064. Crella spinulata 1141, 1142. Cribrochalina sp. 935, 936. Crossaster papposus 719, 720. Ctenocella sp. 776. Cucumaria sp. 709. Culcita novaeguineae 759. Curvularia sp. 6540 335, 336, 337, 340. Curvularia sp. 768 337, 338, 339, 340. Cylindrospermum musicola 533, 534, 577. Cynthia sp. 733. Cystodytes sp. 535, 537. Cystoseira sp. 1049. D Dactylospongia sp. 513. Damiriana hawaiiana 775. Dasychalina sp. 887. Dasystenella acanthina 646, 647, 725, 738, 739, 770, 834. Deltocyathus magnificus 639. Dendronephthya gigantea 696, 722, 723. Dendronephthya sp. 638, 779, 780, 781, 782. Diaporthe sp. 612. Dichotella fragilis 751, 752. Dichotella gemmacea 321. Dictyonella incisa 836, 871. Dictyota crenulata 101. Dinophysis acuminata 447, 448, 449, 453, 454, 480. Dinophysis acuta 452.

498

Index 3 Compound Organism Source Index

Dinophysis fortii 218, 447, 448. Dinophysis norvegica 453, 454. Dinophysis sp. 450, 451. Dinophysis spp. 219. Diplasterias brucei 734, 892. Discodermia dissoluta 613. Discodermia sp. 28, 112, 113. Dolabella auricularia 520, 521, 522, 523. Dysidea arenaria 735. Dysidea herbacea 760, 915. Dysidea incrustans 777, 778. Dysidea sp. 490, 735, 736, 737, 895. E Echinaster sepositus 816. Echinocardium cordatum 982. Echinoclathria subhispida 1078. Echinomuricea sp. 1018. Echinus esculentus 982. Eleutherobia sp. 639. Elysia timida 606. Emericella variecolor GF10 622, 623. Epipolasis kushimotoensis 929. Epipolasis sp. 758, 831, 832, 929, 930, 931. Erylus lendenfeldi 746. Eudistoma cf. rigida 535, 536, 537, 538. Eunicea fusca 710, 1049. Eunicella cavolini 890, 1121, 1122, 1125, 1126, 1127. Eupentacta fraudatrix 709, 982. Euplexaura anastomosans 659. Euryspongia sp. 747, 748. F Fascaplysinopsis sp. 576, 591. Fasciospongia cavernosa 754. Fasciospongia rimosa 524, 556, 592. Forcepia sp. 440, 441, 442, 443, 444, 445. Fusarium sp. 603. Fusarium sp. 05JANF165 602. Fusarium sp. 95F858 601. Fusarium tricinctum MFB392-2 601. G Galaxaura marginata 673, 674, 721, 744, 764, 765, 766, 767, 768, 769. Gambierdiscus toxicus 163, 164, 165, 166, 167, 168, 185, 199, 201, 202. Gambierdiscus toxicus GII-1 192.

Geitlerinema sp. 468, 469. Gellius sp. 753, 828, 829. Gerardia savaglia 837. Gersemia fruticosa 679, 704, 731, 743, 771, 1121, 1122. Gliocladium sp. 60. Gomophia watsoni 685, 759. Goniopecten demonstrans 755, 756, 757. Gonyaulax spinifer 212. Gorgonocephalus caryi 706. Gorgonocephalus chilensis 693, 695, 706. Gracilaria coronopifolia 88, 89, 243. Gracilaria edulis [Syn. Polycavernosa tsudai] 567, 568, 569, 570, 571. Gracilaria sp. 335, 336, 337, 340. Gymnascella dankaliensis 880, 881, 921, 922, 923, 924. Gymnocrinus richeri 871, 891. Gymnodinium breve 181. Gymnodinium breve [Syn. Ptychodiscus brevis] 146, 147, 153, 154, 155, 156, 162. Gymnodinium mikimotoi [Syn. Karenia mikimotoi] 169, 170, 171. Gymnothorax javanicus 199. H Halichoeres bleekeri 27, 314, 315, 316. Halichondria cf. moorei 929. Halichondria japonica 880, 881, 921, 922, 923, 924. Halichondria melanodocia 224. Halichondria moorei 929. Halichondria okadai 172, 177, 182, 183, 184, 196, 197, 198, 224. Halichondria panicea 129. Haliclona crassiloba 925, 926, 927, 928. Haliclona permollis 1049. Haliclona rubens 631. Haliclona sp. 283, 342, 343, 929. Haliclona spp. 1049. Halityle regularis 759, 993. Halosaccion ramentaceum 721. Heliometra glacialis maxima 677. Hemitedania sp. 440. Henricia downeyae 893, 894. Henricia leviuscula 681, 1020. Henricia sanguinolenta 709, 820, 995. Heritiera globosa 386, 387.

Index 3 Compound Organism Source Index

Hippasteria kurilensis 684, 697, 761, 783, 784, 785, 786, 833, 937. Hippasteria phrygiana 808, 1107. Holothuria nobilis 709, 982. Holothuria scabra 709. Hyatella sp. 524, 541. Hymenomonas sp. 953. Hypoxylon aceanicum LL-15G256 486, 559. Hyrtios altum 481, 579, 580, 581. I Ianthella sp. 1099, 1105, 1106. Ircinia campana 1098. Ircinia fasciculata 288. Ircinia ramosa 510, 516. Ircinia sp. 511, 527, 528, 529, 530, 531, 823, 824, 825. Isis hippuris 835, 839, 840, 841, 842, 843, 844, 845, 846, 847, 848, 849, 850, 853, 938, 939, 940, 941, 942, 943, 979, 980, 981, 1133, 1134, 1135, 1136, 1137. J Jania adhaerens 730. Jania rubens 773. Jaspis serpentina 457. Jaspis sp. 447. Jaspis wondoensis 821, 822, 1015. Jasus lalandei 837. Junceella juncea 871. K Karenia brevis 157, 209, 210. Karenia brevisulcata 158. Karenia mikimotoi [Syn. Gymnodinium mikimotoi) 169, 170, 171. Karlodinium veneficum CCMP 2936 138, 139, 140, 143, 144. L Lamellomorpha strongylata 477. Laurencia majuscula 1076. Laurencia pinnata 648, 809. Laurencia sp. 866, 991. Laurencia viridis 36, 37. Lechevalieria aerocolonigenes 549. Leiodermatium sp. 317. Lendenfeldia chondrodes 1042, 1043. Leptasteriasfusca 787.

499

Leptogorgia punicea 810, 811. Leptogorgia sarmentosa 729, 772, 774. Leptolyngbya cf. 563. Linckia laevigata 788, 789, 802, 819, 957, 958, 1057, 1058, 1059, 1060. Lissoclinum sp. 526, 547, 548. Lissodendoryx fibrosa 749, 750, 854, 855. Lissodendoryx isodictyalis 370, 371, 372. Lissodendoryx noxiosa 1049. Lissodendoryx sp. 172, 172, 173, 174, 175, 176, 180, 183, 187, 188, 193, 194, 195, 197, 440. Litophyton arboreum 972. Litophyton viridis 959, 972. Lituaria australasiae 189, 190, 191. Lobophora convolute 322, 323. Lobophytum laevigatum 631, 710, 856, 916, 965, 1139. Lobophytum mirabile 914. Lobophytum patulum 989. Lobophytum sarcophytoides 1098. Lobophytum sp. 631, 914, 1065. Lophogorgia sp. 1109. Luidia clathrata 682, 683, 686, 688, 690, 691, 790, 802, 963, 964, 966, 967, 1045. Luidia maculata 686, 790, 819. Lumnitzera racemosa 346, 347, 348. Lycodontis javanicus 200. Lyngbya bouillonii 3, 545. Lyngbya gracilis 247. Lyngbya majuscula 64, 65, 66, 66, 70, 71, 72, 74, 76, 77, 78, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 90, 91, 244, 247, 249, 250, 251, 256, 257, 508. Lyngbya sordida 73. Lyngbya sp. 6, 77, 493, 494, 495, 544, 545. Lysastrosoma anthosticta 728. M Marinispora sp. CNQ-140 550, 551, 552, 553. Marthasterias glacialis 790. Mastigias papua 142. Mediaster murrayi 791, 792, 793, 794. Micromonospora sp. 49, 318, 319, 320. Micromonospora sp. M71-A77 542. Microsphaeropsis sp. 604. Minabea sp. 797, 798, 799, 1021, 1022. Monotria japonica 10. Moorea producens 75.

500

Index 3 Compound Organism Source Index

Muricella sp. 1113, 1116, 1117, 1118, 1119, 1120. Mycale adhaerens 517. Mycale hentscheli 564, 565. Mycale sp. 589. Myriapora truncata 32, 33, 677, 871. Mytilus edulis 161, 219, 596. Mytilus galloprovincialis 145, 186, 212. N Nardoa tuberculata 685, 759. Navanax inermis 35. Neosiphonia superstes 461, 462, 463, 464, 465, 466, 467, 586, 587. Nephthea albida 971, 972, 973. Nephthea chabroli 800, 872, 969, 970. Nephthea erecta 900, 901, 902, 912, 959, 961, 962, 971, 972. Nephthea simulata 973. Nephthea sp. 965. Nephthea tiexieral verseveldt 971. Nocardiopsis sp. CMB-M0232 388. Nostoc linckia 496. Nostoc spongiaeformia 496. Notarchus leachii 614. O Occurs in contaminated shellfish 216, 223, 228, 239, 240, 241, 242. Occurs in contaminated shellfishes, such as mussel Mytilus edulis, Placopecten magellanicus 237. Occurs in cyanobacteria 247. Occurs in fish and shellfish esp. coral reef spp., carnivorous fishes 199. Occurs in fungi 918. Occurs in fungi and lichens 891. Occurs in green algae 982. Occurs in higher animals, fish liver oils, egg yolk, bile and gallstones etc. 710. Occurs in marine organisms 710, 721, 982. Occurs in mussels 218. Occurs in plants and animals 631. Occurs in silkworm 837. Occurs in sponges 213, 918. Ophiarachna incrassata 692, 695, 707. Ophiarthrum elegans 692. Ophidiaster ophidianus 802, 819. Ophiocoma dentata 692. Ophiocoma echinata 692.

Ophiocoma scolopendrina 692. Ophiocoma wendti 692. Ophioderma longicaudum 692, 695, 702, 706. Ophiolepis superba 695. Ophionereis reticulata 692. Ophionotus victoriae 695, 706. Ophiopholis aculeata 695. Ophioplocus januarii 692. Ophiothrix fragilis 695, 706. Ophiozona impressa 692, 695. Ophiura leptoctenia 706. Ophiura sarsi 695. Ophiura texturata 695, 706. Oreaster reticulatus 802. Oscillatoria nigroviridis 245, 246, 248, 254, 255. Oscillatoria sp. 560. Oscillatoria spp. 563. Ostreopsis cf. ovata 17. Ostreopsis ovata 45. Ostreopsis siamensis 141. Ovary of queen honeybee 696. P Pacifigorgia sp. 561. Paecilomyces lilacinus ZBY-1 883, 891, 899. Pandaros acanthifolium 213, 645, 804, 805, 806, 807, 857, 858, 983, 984, 985, 986, 1032, 1033, 1034, 1066, 1067, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075. Paraminabea acronocephala 797, 798, 799, 1021, 1022, 1024, 1025, 1026, 1027, 1028. Patinopecten yessoensis 186, 211, 212, 218, 677, 705, 721, 1049. Penaeus orientalis 818. Penicillium chrysogenum 273, 288, 866, 991. Penicillium chrysogenum PJX-17 286, 287. Penicillium citrinum 284. Penicillium citrinum SpI080624G1f01 270. Penicillium commune SD-118 871, 891. Penicillium flavidorsum SHK1-27 262. Penicillium sp. 910. Penicillium sp. F00120 891. Penicillium sp. F23-2 289, 290, 291, 292, 293, 294. Penicillium sp. PSU-F44 497, 514. Penicillium stoloniferum QY2-10 896. Penicillium sumatrense 346, 347, 348. Penicillium terrestre 275, 276, 282, 296, 300.

Index 3 Compound Organism Source Index

Perinereis aibuhitensis 733. Perna canaliculus 149, 150, 151, 152. Petrosia ficiformis 1105. Petrosia weinbergi 1023, 1111. Phakellia carteri 172, 178, 183. Phakellia sp. 180, 217. Phallusia mamillata 1052. Phialocephala sp. 278, 281. Phialocephala sp. FL30r 279, 285, 301, 302, 303, 304. Philinopsis speciosa 34, 35. Phorbas amaranthus 653, 654, 655, 656, 657. Phorbas sp. 305, 306, 307, 308. Phormidium sp. 566. Phormidium spp. 509. Pinna atropurpurea 229, 232. Pinna attenuata 229, 232. Pinna muricata 229, 230, 231, 232. Plakortis aff. angulospiculatus 11, 14. Plakortis angulospiculatus 610, 621. Plakortis halichondrioides 10. Plakortis simplex 10, 11, 15, 16, 40. Plakortis zyggompha 600, 608, 609. Plazaster borealis 708. Pleraplysilla sp. 671. Poecillastra laminaris 867. Poecillastra sp. 447, 455, 456, 457. Poecillastra wondoensis 821, 822, 1015. Polycavernosa tsudai [Syn. Gracilaria edulis] 567, 568, 569, 570, 571. Polyfibrospongia sp. 385. Polymastia boletiformis 992. Polythoa sp. 132. Polythoa toxica 132. Polythoa tuberculosa 132. Porphyridium cruentum 796. Prorocentrum belizeanum 24, 225, 491, 492. Prorocentrum hoffmannianum CCMP683 18. Prorocentrum lima 215, 519, 574. Prorocentrum lima PL2 226, 227. Prorocentrum maculosum 575. Prorocentrum sp. 4, 5, 578. Protocentrum lima 220, 224. Protocentrum maculusum 221, 222. Protoceratium reticulatum 203, 204, 205, 206, 212. Prymnesium parvum (class Haptophyceae) 207, 208. Psammoclemma sp. 510.

501

Pseudaphanostoma luteocoloris 31. Pseudoaxinissa digitata 932, 933, 934. Pseudoptero gorgiaamericana 1100, 1131. Pseudopterogorgia americana 996. Pseudopterogorgia sp. 996, 1110, 1128. Psolus fabricii 709. Pteraster pulvillus 693. Pteraster tessellatus 706. Pteria penguin 233, 234, 235. Ptilocaulis spiculifer 838. Ptychodiscus brevis [Syn. Gymnodinium breve] 146, 147, 153, 154, 155, 156, 162. R Reidispongia coerulea 458, 459, 460, 464. Rhizopus sp. 883, 888, 889, 891, 896, 897, 897, 948, 950, 951, 952. Rhizopus sp. 2-PDA-61 22, 23. Rhodymenia palmate 721. S Salinispora arenicola CNH643 115. Salinispora arenicola YM23-082 38, 114. Sarcophyton crassocaule 631, 856. Sarcophyton glaucum 965. Sargassum horneri 599. Sargassum thunbergii 260, 262, 263, 266, 868, 871, 891. Sargassum tortile 1049. Schizothrix calcicola 245, 246, 248, 254, 255. Scleritoderma cf. paccardi 917. Scleronephthya gracillimum 632, 633, 634. Scleronephthya pallida 637. Scleronephthya sp. 727. Sclerophytum sp. 914, 916. Scytonema burmanicum 533. Scytonema mirabile 533. Scytonema musicola 533. Scytonema ocellatum 533. Scytonema pseudohofmanni 577. Scytonema spp. 515, 534, 590. Siliquariaspongia mirabilis 555. Sinularia abrupta 997. Sinularia aramensis 1098. Sinularia brassica 1029, 1030, 1031. Sinularia conferta 968. Sinularia crassa 876, 877, 878, 879. Sinularia flexibilis 1098. Sinularia gibberosa 919, 920, 982.

502

Index 3 Compound Organism Source Index

Sinularia hirta 968. Sinularia humilis 998, 999. Sinularia leptoclados 994. Sinularia microclavata 977. Sinularia numerosa 977. Sinularia ovispiculata 903. Sinularia remei 994. Sinularia sp. 946, 971, 977, 982, 1098. Siphonaria denticulata 25, 26. Siphonaria grisea 41, 42, 43, 44. Siphonaria pectinata 41, 42, 43, 44. Sonneratia apetala 344, 345. Spirastrella spinispirulifera 582, 583, 584, 585. Spongia agaricina 1123, 1124. Spongia mycofijiensis 524. Spongia sp. 19, 518, 579, 580, 581, 649, 650, 651, 652, 864, 865, 1039. Spongionella gracilis 677, 871. Squalus acanthias 724. Stegophiura brachiactis 695. Stelletta clarella 1049. Stelletta hiwasaensis 978. Stelletta sp. 595, 597, 605, 607, 817. Streptomyces antibioticus 349, 350. Streptomyces arenicola CNR-005 38. Streptomyces arenicola CNR-059 39. Streptomyces aureoverticillatus NPS001583 2. Streptomyces griseus 309, 487, 488, 489. Streptomyces hygroscopicus 27, 309, 315, 316. Streptomyces hygroscopicus OUPS-N92 314. Streptomyces lusitanus 351. Streptomyces lusitanus SCSIO LR32 121, 122, 123, 124, 125, 126. Streptomyces seoulensis 818. Streptomyces sp. 46, 47, 117, 127, 128, 130, 131, 313, 324, 325, 326, 362, 363, 386, 387, 558, 611. Streptomyces sp. B1751 365. Streptomyces sp. CNQ-431 352, 353, 354, 355, 356, 357, 358, 359, 360, 361. Streptomyces sp. HB202 129. Streptomyces sp. KORDI-3238 48. Streptomyces sp. MDG-014-17-069 588. Streptomyces sp. MP39-85 116. Streptomyces sp. Ni-80 364, 365. Streptomyces sp. NPS-643 615, 616, 617, 618, 619, 620. Streptomyces sp. RJA635 309, 310.

Streptomyces sp. RJA71 311, 312. Streptomyces sp. SK 1071 543. Strongylophora sp. 627. Stylocheilus longicauda 89, 101, 244, 247. Svenzea zeai 987, 988. Symbiodinium sp. 118. Symbiodinium sp. Y-6 593, 594. Symploca cf. sp. 474. Synapta maculata 982. Synoicum adareanum 562. T Tedania ignis 589. Tedania sp. 440. Telesto riisei 814, 815. Terrestrial fungus Craterellus odoratus 598. Terrestrial fungus Fusarium sp. K432 601, 602. Terrestrial fungus Penicillium aurantiogriseum 866. Terrestrial mushroom Grifola frondosa 910, 952. Terrestrial mushroom shii-take Lentinus edodes 896. Terrestrial plant Astraeus hygrometricus 904. Terrestrial plant Typha latifolia 883. Terrestrial plants 837. Terrestrial plants Polypodium vulgare 837. Terrestrial streptomycete Streptomyces sp. MK67-CF9 331. Tethya aurantia 1049. Thalysias juniperina 891. Theonella sp. 67, 68, 68, 69, 93, 94, 95, 96, 97, 99, 100, 102, 103, 104, 105, 106, 470, 471, 475, 476. Theonella swinhoei 94, 102, 103, 104, 106, 107, 108, 109, 110, 111, 472, 473, 474, 475, 476, 478, 479, 640, 641, 873, 874, 875, 882, 884, 885, 1035, 1054, 1079, 1080, 1081, 1082, 1083, 1084, 1085, 1086, 1140, 1143, 1144. Thromidia catalai 802. Tolypothrix conglutinata var. colorata 590. Topsentia ophiraphidites 803. Topsentia sp. 886, 929, 1009, 1010, 1011, 1012, 1013, 1087, 1103. Torula herbarum 614. Toxadocia zumi 675, 678.

Index 3 Compound Organism Source Index

Trachycladus laevispirulifer 98. Trachyopsis sp. 929. Trichoderma koningii MF349 624. Trichoderma longibrachiatum 283. Trichoderma sp. 297, 298, 299. Trichoderma sp. f-13 271, 272, 273, 274, 277, 280, 282, 295, 300. Trichoderma sp. GIBH-Mf082 677. Trichodesmium erythraeum 252, 253. Trochostoma orientale 709. Turbinaria conoides 1044, 1049, 1050, 1051, 1053, 1077. Tydemania expeditionis 1138. U Unidendified moss 910. Unidentified actinomycete Y-8521050 50. Unidentified ascomycetous fungus 1. Unidentified Chinese sea squirt 896. Unidentified contaminated scallops 236, 238. Unidentified dinoflagellate 540. Unidentified fungus 497. Unidentified fungus 0GOS1620 497. Unidentified fungus B00853 282. Unidentified gorgonian 558. Unidentified lithistid sponge (family Neopeltidae) 518. Unidentified mangrove 267, 269, 332, 333, 334. Unidentified mangrove-derived fungus 1850 268. Unidentified mangrove-derived fungus 2526 267, 269. Unidentified mangrove-derived fungus Zh6-B1 344, 345.

503

Unidentified marine bacterium (Actinomycetales and Maduromycetes) 546. Unidentified marine nudibranch 461. Unidentified marine-derived actinomycete CNB-837 322, 323. Unidentified marine-derived fungus K063 119. Unidentified mussels 203. Unidentified phytoplankton 214, 236, 238. Unidentified phytoplankton assemblages 214, 236, 238. Unidentified scallops 214. Unidentified shellfish 446. Unidentified sponge 284. Unidentified sponge (class Demospongiae) 270. Unidentified sponge (order Poecilosclerida) 1055, 1056. Unidentified sponges (order Haplosclerida) 935. Unidentified starfish (family Asteriidae) 661, 662, 663, 664, 665, 869. Unidentified starfish (family Echinasteridae) 680, 687, 689, 698, 699, 700. V Varicosporina ramulosa 61, 62, 63. Vulcanodinium rugosum 625. X Xestospongia bergquistia 823, 824. Xestospongia sp. 130, 131, 745, 954, 955, 1088, 1089, 1090, 1091, 1092, 1093, 1094, 1095, 1096. Xestospongia testudinaria 1097, 1102, 1104.

Index 4 Compound Sampling Geographic Locality Index In this index, all geographic locations in HAMNP Volume 5 have been devided as 16 large areas: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16

CHINA JAPAN RUSSIA KOREA WATERS R. O. KOREA ASIA AUSTRALIA OCEANIA EUROPE AFRICA USA NORTH AMERICA CARIBBEAN SEA SOUTH AMERICA PACIFIC OCEAN ANTARCTIC/ARCTIC

For all 168 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 5” and a number code sequence of the related compounds follows the detail information immediately. There are 730 related compounds with geographic information in HAMNP Volume 5. 1 CHINA China, Beibuwan Bay, Guangxi 614. China, China waters 22, 23, 259, 261, 267, 271, 272, 273, 274, 277, 280, 282, 295, 300, 883, 888, 889, 891, 896, 897, 948, 950, 951, 952. China, Dongshan I., Guangdong 925, 926, 927, 928. China, Fujian 351. China, Guangdong 349, 350. China, Hainan 904, 905, 906, 907, 908, 909, 947, 960, 974, 975. China, Heishijiao Bay, Dalian, Shandong 313. China, Jiaozhou Bay, Shandong 275, 276, 296. China, Meishan, Sanya 751, 752. China, Pingtan I., Fujian 260, 262, 263, 266, 868, 871, 891. China, Qingdao, Shandong 818. China, Weizhou Reef, South China Sea 321.

China, Wenchang, Hainan 346, 347, 348, 386, 387. China, Xisha Is., South China Sea 1143, 1144. China, Zhuhai, Guangdong 344, 345. South China Sea, Northern South China Sea 891. South China Sea, South China Sea 121, 122, 123, 124, 125, 126, 267, 269, 324, 325, 326, 624, 677, 873, 882, 884, 885, 903, 949, 998, 999, 1054, 1076, 1080, 1081, 1082, 1083, 1084, 1085. South China Sea, Yongxing I., South China Sea, China 10, 11. Taiwan, Green I. 632, 633, 634. Taiwan, Orchid I. 1133, 1134, 1135, 1136, 1137. Taiwan, Pingtung County 672, 797, 798, 799, 1021, 1022, 1024, 1025, 1026, 1027, 1028, 1035, 1086. Taiwan, Siaoliouciou I. 872.

Index 4 Compound Sampling Geographic Locality Index

Taiwan, South Bay, Southern Taiwan 4, 5. Taiwan, Taitung County 800, 876, 877, 878, 879, 969, 970. Taiwan, Taiwan waters 70, 71, 72, 578, 673, 674, 721, 744, 762, 763, 764, 765, 766, 767, 768, 769, 900, 901, 902, 912, 919, 920, 941, 944, 945, 946, 982, 1018, 1029, 1030, 1031, 1044, 1050, 1051, 1053, 1077, 1098, 1101, 1129, 1130. Yellow Sea 1138. 2 JAPAN Japan, Charatsunai beach, Muroran 362, 363. Japan, Japan waters 104, 105, 224, 385, 432, 522, 523, 582, 622, 623, 635, 636, 638, 649, 650, 651, 652, 708, 722, 727, 758, 817, 831, 832, 859, 860, 864, 865, 880, 881, 922, 923, 924, 929, 930, 931, 935, 936, 978, 1039. Japan, Kochi 142. Japan, Kochi Harbour 615, 616, 617, 618, 619, 620. Japan, Kushimoto Bay, Wakayama 170. Japan, Mie prefecture 435, 436, 437, 438, 439. Japan, Miyazaki Harbour, Japan 611. Japan, off Izu Peninsula 779, 780, 781, 782. Japan, off Kerama I., Ryukyu Archipelago 102, 103, 104, 106, 107, 108, 109, 110, 111. Japan, Oshima-Shinsone 12, 13, 1132. Japan, Shi-shi I., Kagoshima 1141, 1142. Japan, Tokunoshima I. 494, 495. Japan, Usa Bay, Kochi prefecture 51, 52, 53, 54, 55, 56, 57, 58, 59. Okinawa, Cape Zampa 592. Okinawa, Iriomote I. 539. Okinawa, Ishigaki I. 132, 270, 284, 736, 737, 895. Okinawa, Kerama I. 94. Okinawa, off Kerama I. 68, 69, 93, 99. Okinawa, Okinawa 68, 84, 119, 229, 230, 231, 233, 234, 235, 427, 481, 526, 527, 528, 529, 530, 531, 556, 579, 580, 581, 823, 824, 825, 870, 957, 958, 1000, 1001, 1002, 1009, 1010, 1011, 1012, 1013, 1016, 1017, 1019, 1058, 1059, 1087, 1088, 1089, 1090, 1091, 1092, 1093, 1094, 1095, 1096, 1108, 1112. Okinawa, Zanpa 400.

505

3 RUSSIA Kuril Is., Kuril Is. 693. Kuril Is., Kuril Is., Sea of Okhotsk 761, 833, 937. Sea of Okhotsk, Russia Sea of Okhotsk 681, 808, 1020, 1107. 4 KOREA WATERS Korea waters, 595, 597, 599, 605, 607, 642, 643, 644, 740, 741, 742, 827, 851, 852, 898, 1113, 1119, 1120. 5 R. O. KOREA Jeju I. Jeju I. 17. 6 ASIA Bering Sea 812, 813. India waters 903. Indian Ocean 871. Indian Ocean Andaman and Nicobar Is. 856. Indonesia 283, 840, 842, 843, 844, 849, 850, 938, 939, 940, 941, 942, 943, 979, 980, 981. Indonesia Bunaken Marine Park 882. Indonesia Bunaken Marine Park, Manado 479, 887. Indonesia North Sulawesi 854, 855. Indo-Pacific Sea Indo-Pacific Sea 819. Maldives 518, 579, 580, 581. Philippines Coron I. 749, 750. Philippines 511, 745, 954, 955. Red Sea Al-Shoaiba coast 730. Red Sea 473, 474, 475, 476. Saudi Arabia Jiddah 75. Sea of Japan Posyet Bay 787. Thailand 497, 514, 637. Thailand Sichang I., Chonburi 130, 131. Vietnam 788, 789, 914, 1057, 1065. Vietnam Cat Ba I., Haiphong 626, 666, 667, 668, 669, 670, 826. Vietnam Khanh Hoa province 631, 710, 856, 916, 965, 1139. Vietnam Namyet I. 1099, 1105, 1106. Vietnam Quang Ninh 660, 1040. Vietnam Truong Sa Archipelago, Khanh Hoa 1097, 1102, 1104.

506

Index 4 Compound Sampling Geographic Locality Index

7 AUSTRALIA Australia 510, 516. Australia along shore of Bass I., Wollongong 512. South Australia South Australian Pacific 229, 232. Southern Australia 98, 482, 483, 484, 485, 1078. Western Australia 342, 343. 8 OCEANIA Federated States of Micronesia Chuuk State 886. Federated States of Micronesia southeast of Chuuk Lagoon 555. Fiji 474. New Zealand 149, 152, 477. New Zealand benthic, Northland 625. New Zealand Kaikoura 173, 174, 175, 176. New Zealand Kapiti I. 565. New Zealand off Kaikoura coast 172, 180, 183, 187, 188, 193, 194, 195, 197. New Zealand Wellington 158. Palau, Oceania 11, 14, 490, 545, 1042, 1043. Papua New Guinea 505, 506, 544, 572, 573, 589. Papua New Guinea Dutchess I. 73. Papua New Guinea Pigeon I. 3. Polynesia (Fr.), Oceania 168, 199. Solomon Is. 640, 641. Solomon Is. Malaita I. and Vangunu I. 873, 874, 875, 1079, 1080, 1081, 1082, 1083, 1084, 1085. Solomon Is. Malaita I. 1140. Vanuatu 19, 711, 712, 713, 714, 715, 716, 717, 718. 9 EUROPE Adriatic Sea, Italy Adriatic coast 45. Adriatic Sea, Italy Adriatic coast 145. Baltic Sea 129. Baltic Sea, Germany Greifswalder Bodden, Germany 1. France Banyuls-sur-Mer 327, 328, 329, 330, 331. Greece Lichadonissia I. 890, 1121, 1122, 1125, 1126, 1127.

Italy Bay of Naples 676, 701, 703, 726. Italy Tyrrhenian Sea, Italy Tyrrhenian coast 45. Mediterranean Sea 604, 606, 754, 777, 778. Mediterranean Sea Levantine Sea, Eastern Mediterranean 542. Norway 161, 992. Spain 729, 772, 774. Spain Cádiz 41, 42, 43, 44, 1123, 1124. Spain Callao Salvaje, Tenerife, Canary Is. 36, 37. Spain Tenerife I., Canary Is. 61. 10 AFRICA Comoros Is. 172, 178, 183. Egypt Hurghada 472, 478. Kenya Shundo 989. Madagascar 91, 588. Madagascar Nosy Mitso-ankaraha I. 469. Madagascar Salary Bay, Tulear 591. South Africa 628, 630. South Africa Algoa Bay, southeast coast of South Africa 547, 548. South Africa southest coast of Africa 582, 583. Tunisia 773. 11 USA California, USA La Jolla 352, 353, 354, 355, 356, 357, 358, 359, 360, 361. Florida, USA 146, 147, 153, 154, 155, 162, 996. Florida, USA Bush Key, Dry Tortugas 79. Florida, USA Dry Reef Rocks, Key Largo 653, 654, 655, 656, 657. Florida, USA Fort Zachary Taylor State Park, Key West 509. Florida, USA Gulf of Mexico at John’s Pass, Madeira Beach 335, 336, 337, 340. Florida, USA Miami Terrace, Straits of Florida 317. Grenada, USA True Bay 65. Guam, USA 338, 339, 836, 871. Guam, USA Cocos Lagoon 74. Guam, USA Piti Bomb Holes 77. Hawaii, USA 89, 101, 244, 627. Maui, USA 1055, 1056. Maine, USA Coast of Maine 217. USA Delaware Bays 138, 139, 140, 143, 144. Virgin Is., USA St. Thomas 507. Belize 322, 323.

Index 4 Compound Sampling Geographic Locality Index

12 NORTH AMERICA Canada British Columbia 830. Canada Nova Scotia 214, 236, 238. Canada Vancouver 671. Gulf of Mexico 682, 683, 688, 690, 691, 893, 894, 963, 964, 966, 967, 1045. Honduras off north coast of Honduras 112, 113. Panama Caribbean coast of Panama 753, 828, 829. 13 CARIBBEAN SEA Bahamas Caribbean Sea 28, 508. Bahamas North Cat Cay 117. Caribbean Sea 15, 16, 224, 297, 298, 299, 440, 917, 987, 988, 1100, 1131. Curacao I., Caribbean Sea 87. Jamaica off north coast 518. Martinique I. (Fr.), Caribbean Sea 645, 857, 858, 983, 984, 985, 986, 1032, 1033, 1034, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075. Yucatan Yucatan coast, Gulf of Mexico 34, 35. 14 SOUTH AMERICA Brazil 814, 815. Chile 497. Colombia Santa Marta Bay, Caribbean Sea 710, 1049.

507

15 PACIFIC OCEAN East Pacific Ocean 278, 281. New Caledoinia (Fr.) 19, 189, 190, 191, 460, 466, 467, 503, 504, 587, 747, 748, 776. New Caledonia (Fr.) off New Caledonia 458, 459, 502, 586. Pacific Ocean 728, 867. Palmyra Atoll, Northern Pacific Ocean 563. 16 ANTARCTIC/ARCTIC Antarctic 646, 647, 665, 680, 687, 689, 698, 699, 700, 702, 706, 725, 738, 739, 770, 834, 861, 862, 863, 869, 911, 1036, 1037, 1038. Antarctic Antarctic, Ross Sea, Terra Nova Bay 734, 892. Antarctica near Anvers I. 562. Antarctica Norsel Point, Palmer Station 976, 1061, 1062, 1063, 1064. Arctic, Northern Russia 679, 704, 731, 743, 771, 1122. Arctic Ocean 1121. South Pole 910.

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. 5 5α-Reductase inhibitor 913, 968. A Acaricide 487. AChE inhibitor 296. Actin-binding activity 458. Actinomyosin ATP-ase modulator 525. Actomyosin ATPase stimulator 480. Adenosine receptor agonist 929. Affects nuclear receptors, HepG2 cell transfected with FXR or PXR 873. Affects nuclear receptors, using HepG2 cell transfected with FXR or PXR 884, 885, 1080, 1082, 1084, 1085. Affects nuclear receptors, using HepG2 cell transfected with PXR 1081, 1083. Algicide 134. Algicide, diatom Nitzschia sp. 18. Anthelmintic 60. Anti-AD, 3 clinical trials are going on (Russo, 2016) 366. Anti-AD, preclinical studies show that bryostatin 1 has nine effects, the summary in the book 366. Anti-AD, preclinical trial, Russo, 2016 214, 518. Antialgal 61. Antialgal, green alga Chlorella fusca 268, 335, 336, 337, 340. Antiallergic 823. Antiarrhythmic 837. Antiarrhythmix 994. Antibacterial 46, 47, 546, 733. Antibacterial inactive, Bacillus subtilis 31. Antibacterial inactive, Bacillus subtilis ATCC 6633 258, 264. Antibacterial inactive, Bacillus subtilis IFO 3134 38, 115. Antibacterial inactive, Cytophaga marinoflava IFO 14170 38, 115. Antibacterial inactive, Escherichia coli 724.

Antibacterial inactive, Escherichia coli IFO 3301 38, 114, 115. Antibacterial inactive, MDRSA 599, 601, 602. Antibacterial inactive, MRSA 599, 602. Antibacterial inactive, MRSA clinical isolate 309 258, 264, 265. Antibacterial inactive, Pseudomonas aeruginosa 724. Antibacterial inactive, Pseudomonas aeruginosa ATCC 15692 258, 264, 265. Antibacterial inactive, Pseudomonas aeruginosa IFO 3446 38, 114, 115. Antibacterial inactive, Staphylococcus aureus 599, 602, 992. Antibacterial inactive, Staphylococcus aureus ATCC 6538 258, 264. Antibacterial inactive, Staphylococcus epidermidis 498, 501. Antibacterial inactive, Xanthomonas campestris 500, 501. Antibacterial, antarctic marine bacteria McM13.3 698, 861, 911, 1036, 1037, 1038. Antibacterial, antarctic marine bacteria McM32.2 698, 861, 911, 1036, 1037, 1038. Antibacterial, antarctic marine bacterium McM11.5 863. Antibacterial, antarctic marine bacterium McM32.2 862. Antibacterial, Bacillus megaterium 335, 336, 337, 340. Antibacterial, Bacillus subtilis 81, 119, 129, 324, 325, 326, 682, 683, 688, 690, 691, 963, 964, 966, 967, 1045. Antibacterial, Bacillus subtilis ATCC 6633 260, 265. Antibacterial, Bacillus subtilis IFO 3134 114. Antibacterial, Brevibacterium epidermidis 129. Antibacterial, Corynebacterium xerosis IFM 2057 119. Antibacterial, Cytophaga marinoflava IFO 14170 114.

Index 5 Compound Pharmacological Activity Index

Antibacterial, Dermabacter hominis 129. Antibacterial, Enterococcus faecium 550, 551, 552, 553. Antibacterial, Escherichia coli 260, 262, 263, 266, 822, 868, 956, 1009, 1010, 1011, 1012, 1013, 1015. Antibacterial, gram-positive and -negative bacteria 63. Antibacterial, gram-positive bacteria 41, 42, 43, 44, 48, 120, 309, 487, 488, 489, 998, 999. Antibacterial, Klebsiella pneumonia 129. Antibacterial, Laribacter hongkongensis 351. Antibacterial, Micrococcus luteus IFM 2066 119. Antibacterial, MRSA 129, 313, 601. Antibacterial, MRSA clinical isolate 309 260. Antibacterial, MRSA SK1 497, 514. Antibacterial, Mycobacterium bovis 324. Antibacterial, Mycobacterium smegmatis 81. Antibacterial, Propionibacterium acnes 129. Antibacterial, Pseudomonas aeruginosa 129, 822, 1009, 1010, 1011, 1012, 1013, 1015. Antibacterial, Pseudomonas aeruginosa ATCC 15692 260. Antibacterial, Sarcina lutea 31. Antibacterial, Staphylococcus aureus 31, 129, 260, 262, 263, 266, 321, 325, 326, 351, 550, 551, 552, 553, 601, 682, 683, 688, 690, 691, 724, 868, 956, 963, 964, 966, 967, 1045. Antibacterial, Staphylococcus aureus 209P 119. Antibacterial, Staphylococcus aureus ATCC 6538 265, 260. Antibacterial, Staphylococcus aureus IFO 12732 38, 114, 115. Antibacterial, Staphylococcus epidermidis 129, 499, 500. Antibacterial, Staphylococcus lentus 129. Antibacterial, VRE 313. Antibacterial, Xanthomonas campestris 498, 129, 499. Antibarnacle 686, 802. Antibiotic 595. Anticancer-Cell-Effect 468, 563. Anticomplementary agent 918. Anticyanobacterial 63. Antifeedant 653, 654, 655, 656, 657. Antifeedant, dietary preference study using sea hare Stylocheilus longicauda, increases

509

feeding at low concentrations and inhibits feeding at higher concentrations 76, 77. Antifeedant, mesograzers 976, 1061, 1062, 1063, 1064. Antifeedant, steroidal feeding inhibitor 639. Antifertility agent 694. Antifoulant 751, 752, 893. Antifoulant, barnacle Balanus amphitrite cyprid larvae 635, 636, 638, 727. Antifoulant, barnacle Balanus amphitrite larvae 321. Antifoulant, blue mussel Mytilus edulis galloprovincialis 1042, 1043. Antifoulant, growth inhibition of bacteria Pseudoalteromonas sp. and Polaribacter sp. 1097, 1102, 1104. Antifoulant, inhibits larval settlement of barnacle Balanus amphitrite 779, 780, 781, 782. Antifoulant, inhibits settlement of barnacle larvae 682, 683, 688, 690, 691, 963, 964, 966, 967, 1045. Antifungal 29, 41, 44, 50, 98, 108, 109, 110, 111, 164, 165, 166, 167, 191, 309, 364, 474, 486, 525, 531, 559, 561, 590, 601, 602, 613, 733, 746, 998, 999. Antifungal inactive, Candida albicans 478, 724, 992. Antifungal inactive, Candida albicans ATCC 90028 119. Antifungal inactive, Candida albicans IFO 1060 114, 115. Antifungal inactive, MG SH-MU-4 497. Antifungal inactive, Saccharomyces cerevisiae GT160-45C 859, 860. Antifungal inactive, Saccharomyces cerevisiae RAY-3Aa 859, 860. Antifungal inactive, Trichophyton mentagrophytes 1087. Antifungal, against protozoa and plant pathogenic fungi 341. Antifungal, Alternaria brassicae 866, 991. Antifungal, Aspergillus niger 133, 134, 215, 866, 991. Antifungal, Aspergillus oryzae 515, 533. Antifungal, Candida albicans 116, 349, 350, 386, 387, 472, 515, 533, 1012, 1013. Antifungal, Candida albicans IFO 1060 38.

510

Index 5 Compound Pharmacological Activity Index

Antifungal, Candida albicans SC5314 624. Antifungal, Candida albicans, MMOA: - MDR1 efflux pump inhibition 886. Antifungal, Candida glabrata 116. Antifungal, Candida rugosa 215. Antifungal, erg6 mutant of Saccharomyces cerevisiae 107. Antifungal, Eurotium repens 62. Antifungal, fungi growth inhibitor 62. Antifungal, Microbotryum violaceum 337, 340, 335, 336. Antifungal, Micrococcus luteus 116. Antifungal, Mortierella ramanniana 817. Antifungal, Mortierella 1078. Antifungal, Mortierella remannianus 1012, 1013. Antifungal, Mycotypha microspore 268. Antifungal, Penicillium funiculosum 215. Antifungal, Penicillium notatum 515, 533. Antifungal, Pythium ultimum 992. Antifungal, Saccharomyces cerevisiae 515, 533. Antifungal, Saccharomyces cerevisiae 14028g 859, 860. Antifungal, Saccharomyces cerevisiae A364A 859, 860. Antifungal, Saccharomyces cerevisiae STX338-2C 859, 860. Antifungal, Saccharomyces cerevisiae, MMOA: - MDR1 efflux pump inhibition 886. Antifungal, Septoria tritici 335, 336, 337, 340. Antifungal, Trichophyton mentagrophytes 51, 52, 53, 54, 55, 56, 57, 58, 59. Antifungal, wild type Saccharomyces cerevisiae 107. Antigenotoxic, hmn peripheral blood cells 730. Antihistaminic 997. Antihistaminic, strongly inhibits release of histamine from rat mastocysts 747, 748. Anti-HIV 497, 934, 288. Anti-HIV, HIV inhibitor 932, 933. Anti-HIV-1, cytoprotective agent 706. Anti-HIV-1, NCI primary screen 1103. Anti-HSV-1 1. Antihypertensive 990. Anti-inflammatory 621, 837, 1000, 1001, 1002, 1108.

Anti-inflammatory antidromic action, immunoblot analysis, RAW264.7 cells, stimulates expression of COX-2 876, 877, 878. Anti-inflammatory, hmn neutrophils, superoxide anion generation inhibitor 672. Anti-inflammatory, immunoblot analysis, RAW264.7 cells, inhibits expression of iNOS 877, 879. Anti-inflammatory, Inhibits expression of iNOS and COX-2 in stimulated macrophages 632, 633, 634. Anti-inflammatory, LPS-stimulated RAW264.7 cell, up-regulation of iNOS and COX-2, reduced levels of iNOS and COX-2 1006. Anti-inflammatory, LPS-stimulated RAW264.7 cells, inhibits up-regulation of iNOS and COX-2 920. Anti-inflammatory, LPS-stimulated RAW264.7 cells, inhibits up-regulation of iNOS and COX-2, cell survival is not changed 900, 912. Anti-inflammatory, LPS-stimulated RAW264.7 cells, inhibits up-regulation of iNOS, doesn’t inhibit COX-2 expression, cell survival is not changed 901, 902. Anti-inflammatory, LPS-stimulated RAW264.7 cells, inhibits up-regulation of pro-inflammatory protein β-actin 920. Anti-inflammatory, mus ear assay, inhibits topical PMA-induced edema 322, 323. Anti-inflammatory, NO and TNF-R production inhibitor 595. Anti-inflammatory, NO production assay, LPS-induced RAW macrophage cells, with only modest cytotoxicity 73. Anti-inflammatory, pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine IL-5 and IL-13 352, 354, 355, 356, 357, 358, 359, 360, 361. Anti-inflammatory, pro-inflammatory cytokine production inhibitor, TH2 T lymphocyte cytokine IL-5 353. Anti-inflammatory, RAW264.7 cells, inhibition of LPS induced iNOS and COX-2 expression, reduced iNOS and COX-2 797, 798, 799, 1022.

Index 5 Compound Pharmacological Activity Index

Anti-inflammatory, RAW264.7 cells, inhibition of LPS induced iNOS expression, reduced iNOS 1026, 1027, 1028. Anti-inflammatory, reduced level of iNOS and COX-2 872. Anti-inflammatory, selective NO production inhibitor 605, 607. Anti-inflammatory, Western blot analysis, RAW264.7 cells, inhibition of LPS-induced expression of iNOS and COX-2 1021. Anti-inflammatory, Western blot analysis, RAW264.7 cells, inhibition of LPS-induced expression of iNOS 1024, 1025. Antileishmanial, Leishmania donovani 804, 805, 806, 807, 983, 984, 985, 986, 1066, 1067, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075. Antileishmanial, Leishmania major 327, 328, 329, 330, 331, 12. Antileishmanial, Leishmania mexicana promastigotes 11, 14. Antileukemic 590. Antimalarial 13. Antimalarial, inhibits growth of malarial protozoa Plasmodium falciparum 637. Antimalarial, Plasmodium falciparum 804, 805, 806, 807, 983, 984, 985, 986, 1066, 1067, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075. Antimalarial, Plasmodium falciparum K1 130, 131. Antimicroalgal 998, 999. Antimicrobial 121, 675, 678, 929, 976, 1061, 1062, 1063, 1064. Antimicrobial, various microbial pathogens 925, 926, 927, 928. Antimitotic 187. Antimitotic, caused accumulation of cells arrested in mitosis 172, 178, 183. Antimitotic, taxol-like microtubule stabilizing activity 564. Antimitotic, with a unique mode of action compared with other G2/M blocking agent 317. Antimutagenic, might be useful as chemopreventive agent 709. Antineoplastic, in vivo 191, 367, 368, 375, 433, 434, 461, 462, 463, 464, 746, 775, 853, 1007, 1008.

511

Antineoplastic, in vivo, B16 432. Antineoplastic, in vivo, C26 432. Antineoplastic, in vivo, Ehrlich carcinoma 432. Antineoplastic, in vivo, in both cellular and animal models 612. Antineoplastic, in vivo, L1210 1090, 1092. Antineoplastic, in vivo, Lewis lung carcinoma 432. Antineoplastic, in vivo, member of potentially important new class of antitumour agents 342, 343. Antineoplastic, in vivo, mus 105, 106. Antineoplastic, in vivo, NSCLC 712, 713, 714, 715, 716, 717, 718. Antineoplastic, in vivo, number of human cancer cell lines 390. Antineoplastic, in vivo, P388 102, 103, 369, 372, 374, 385, 432, 507, 517, 535, 536, 537, 538, 1090. Antineoplastic, in vivo, P388 lymphocytic leukemia PS cells 377, 378, 379. Antineoplastic, in vivo, promising results were obtained in phase II clinical trials 366. Antineoplastic, in vivo, useful as growth stimulant or in treatment of coccidiosis 213. Antioxidant 270. Antioxidant, DPPH radical scavenger 272, 273, 284, 295, 297, 298, 299, 300, 549. Antioxidant, superoxide anion ∙O2– scavenger 1018. antiparasitic worms and nematodes 311. Antiplasmodial, Plasmodium falciparum 333, 341. Antiplasmodial, Plasmodium falciparum ItG 12. Antiprotozoal, Leishmania donovani 1032, 1033, 1034, 645, 857, 858. Antiprotozoal, Plasmodium falciparum 1032, 1033, 1034, 645, 857, 858. Antiprotozoal, Trypanosoma brucei rhodesiense 1032, 1033, 1034, 645, 857, 858. Antiprotozoal, Trypanosoma cruzi 1032, 1033, 1034, 645, 857, 858. Antitrypanosomal 549. Antitrypanosomal, Trypanosoma brucei brucei 327, 328, 329, 330, 331. Antitrypanosomal, Trypanosoma brucei rhodesiense 804, 805, 806, 807, 983,

512

Index 5 Compound Pharmacological Activity Index

984, 985, 986, 1066, 1067, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075. Antitrypanosomal, Trypanosoma cruzi 804, 805, 806, 807, 983, 984, 985, 986, 1066, 1067, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075. Antituberculosis Mycobacterium tuberculosis 891. Antituberculosis, Mycobacterium tuberculosis 130, 131, 324, 600, 608, 609, 987, 988. Antituberculosis, Mycobacterium tuberculosis H37Rv 959, 972, 973. Antiulcer 837. Antiviral 94, 595, 851, 1023, 1111. Antiviral inactive, hmn embryonic lung HEL 800. Antiviral, Chikungunya virus inhibitor 252, 253. Antiviral, HCMV 1135. Antiviral, hmn cytogalovirus 741, 852. Antiviral, HSV-1 741, 852, 1119. Antiviral, HSV-1 and VSV 217. Antiviral, HSV-2 1119. Antiviral, influenza virus IFV virus 286, 287. Antiviral, inhibits TMV multiplication 259. Antiviral, Semliki forest virus 694. Antiviral, TMV virus 261, 267. Apoptosis inducer 461, 463, 464, 771, 978, 679, 704. Apoptosis inducer, K562 with a characteristic internucleosomal DNA degradation 743. Apoptosis-inducer, potent 495. Arrests cells in G2/M phase of cell cycle 518. ATPase activator 398. Autophagy inhibitor 310, 312. B Binds to actin covalently 394. Binds to actin subdomain 4 covalently 407. Binds to Protein Kinase C PKC 557. C Ca2+ channel activator 192, 229, 232. Calcium release agent 953. Cannabinoid CB2-receptor ligand, selective 887. Cannabinomimetics, decreasing forskolininduced cAMP accumulation 77. Cardiotoxic 147. Cardiotoxic and Haemolytic agent 132. Cardiotoxin 200, 202.

Cathepsin B inhibitor 1141, 1142. Cathepsin L-like proteases inhibitor, Cathepsin B 329, 331, 330. Cathepsin L-like proteases inhibitor, Cathepsin L 329, 331, 330. Cathepsin L-like proteases inhibitor, Falcipain-2 329, 331, 330. Cathepsin L-like proteases inhibitor, Rhodesain 329, 331, 330. Cathepsin L-like proteases inhibitor, SARS-CoV-PL 331, 330. Causative agent of an outbreak of hmn illness and death in Guan that resulted from eating Polycavernosa tsudai 567. Causes diarrhea, mus 243. CDK/cyclin D1 inhibitor 929. Cell division inhibitor 732. Cell division inhibitor, fertilized sea urchin eggs 791, 792, 793, 794. Cell division inhibitor, sea star Asterina pectinifera fertilised eggs 1113. Cell growth inhibitor 646, 647, 725, 738, 739, 770, 834, 1121, 1122. Cell growth inhibitor, A549 810, 811. Cell growth inhibitor, hmn cancer cell lines 880. Cell growth promoter, murine bone marrow stromal ST-2 cells, very potent and selective 21. Cell proliferation inhibitor 1090, 502, 503, 776, 1093, 1094, 1095, 1096. Cell-adhesion inhibitor 440. Clastogenic 1098. COMPARE analises 314, 315, 316. COMPARE analyses were negative 493. COMPARE analyses were negative, there are no standard anticancer drugs with a high correlation coefficient 535, 536, 537, 538. COMPARE analyses were positive 172, 183, 579, 582, 583. COMPARE analyses were positive, COMPARE Correlation Cocff. = 0.80 [Halichondrin B as “seed”] 187. COMPARE analyses, revealed no significant correlation to any mean-graph profiles contained in NCI’s standard agents database 510. Competes with Brevetoxin-3 binding site, rat brain synaptosomes, without

Index 5 Compound Pharmacological Activity Index

accompanying toxicity associated with brevetoxins 209, 210. Conidia growth inhibitor, Pyricularia oryzae, by swelling effect and induced curling deformation of mycelia 603. Cytoprotective 1103. Cytostatic, cell division inhibitor, fertilized sea urchin eggs 658, 728. Cytostatic, fertilized sea urchin eggs 820. Cytostatic, L5178Y 288. Cytotoxic 13, 36, 37, 49, 82, 92, 141, 177, 182, 215, 380, 381, 446, 458, 471, 524, 528, 529, 530, 531, 532, 534, 544, 554, 564, 565, 584, 585, 590, 613, 628, 630, 675, 678, 733, 760, 851, 1029, 1030, 1031, 1052, 1076. Cytotoxic inactive 622, 623. Cytotoxic inactive, A549 10, 11, 22, 23, 41, 275, 276, 279, 285, 301, 614, 631, 677, 721, 762, 763, 856, 876, 879, 883, 889, 891, 896, 897, 914, 940, 941, 942, 943, 945, 946, 948, 965, 977, 1077, 1130. Cytotoxic inactive, B16 126. Cytotoxic inactive, BC-1 332, 333, 334. Cytotoxic inactive, Bel7402 10, 11, 22, 23, 279, 301, 883, 889, 891, 896, 897, 948, 952. Cytotoxic inactive, BGC823 899. Cytotoxic inactive, BXF-T24 338. Cytotoxic inactive, C6 882. Cytotoxic inactive, Ca9-22 944. Cytotoxic inactive, CXF-HCT116 338. Cytotoxic inactive, CXF-HT29 338. Cytotoxic inactive, DLD-1 827, 898, 1035. Cytotoxic inactive, E39 778. Cytotoxic inactive, EAC 1107. Cytotoxic inactive, GXF-251L 338, 542. Cytotoxic inactive, H9c2 882. Cytotoxic inactive, HCT116 66, 85, 86, 307, 1035. Cytotoxic inactive, HEL 800, 1133, 1134, 1135, 1136, 1137. Cytotoxic inactive, HeLa 126, 882, 991, 993, 1040. Cytotoxic inactive, HeLa-S3 6. Cytotoxic inactive, HepG2 123, 126, 762, 763, 839, 846, 944, 945, 1130. Cytotoxic inactive, HepG3 876. Cytotoxic inactive, HepG3B 944. Cytotoxic inactive, HL60 22, 271, 272, 274, 276, 277, 280, 282, 856, 899, 965.

513

Cytotoxic inactive, hmn breast tumour cells 830. Cytotoxic inactive, hmn melanoma cell lines 778. Cytotoxic inactive, hmn non-small cell lung carcinoma 778, 893, 894. Cytotoxic inactive, HT29 41, 74, 721, 723, 940, 941, 942, 943, 946, 1077, 1099, 1105, 1106, 1133, 1134, 1135, 1136, 1137. Cytotoxic inactive, JB6 P+ CI41 993, 1040. Cytotoxic inactive, K562 279, 285, 301, 302, 303, 304, 576, 731, 743, 743, 899, 1014. Cytotoxic inactive, KB 80, 332, 334, 402, 419, 422, 423, 424, 425, 426, 427, 429, 631, 721, 946, 962, 1077. Cytotoxic inactive, L1210 422, 423, 425, 426, 427. Cytotoxic inactive, L-6 645, 858, 1034. Cytotoxic inactive, LoVo 614. Cytotoxic inactive, LXF-289L 338. Cytotoxic inactive, LXF-526L 338. Cytotoxic inactive, LXF-529L 338, 542. Cytotoxic inactive, LXF-629L 338. Cytotoxic inactive, LXF-H460 338. Cytotoxic inactive, MAXF-MCF7 338. Cytotoxic inactive, MCF7 762, 839, 876, 879, 944, 945, 1035, 1101, 1130. Cytotoxic inactive, MDA-MB-231 762, 763, 839, 846, 879, 944, 1035, 1130. Cytotoxic inactive, MEL28 41, 940, 941, 942, 943, 980. Cytotoxic inactive, MEXF-462NL 338, 542. Cytotoxic inactive, MEXF-514L 338. Cytotoxic inactive, MG63 614. Cytotoxic inactive, mus neuroblastoma cells 88. Cytotoxic inactive, NCI-H460 122, 124, 126, 991. Cytotoxic inactive, NSCLC-L16 661, 664, 665, 869. Cytotoxic inactive, NSCLC-N6 504, 687, 689, 699, 700. Cytotoxic inactive, or mild 666, 667, 668, 669. Cytotoxic inactive, OVXF-1619L 338. Cytotoxic inactive, OVXF-899L 338. Cytotoxic inactive, OVXF-OVCAR3 338. Cytotoxic inactive, P388 22, 41, 279, 302, 303, 304, 659, 721, 821, 822, 827, 852, 898, 921, 940, 941, 942, 943, 980, 1015, 1049, 1077, 1133, 1134, 1135, 1136, 1137.

514

Index 5 Compound Pharmacological Activity Index

Cytotoxic inactive, PAXF-1657L 338. Cytotoxic inactive, PAXF-PANC1 338. Cytotoxic inactive, PC-9 1078. Cytotoxic inactive, PLA2 740, 827. Cytotoxic inactive, PRXF-22RV1 338. Cytotoxic inactive, PRXF-DU145 338. Cytotoxic inactive, PRXF-LNCAP 338. Cytotoxic inactive, PRXF-PC3M 338. Cytotoxic inactive, RXF-1781L 338. Cytotoxic inactive, RXF-393NL 338. Cytotoxic inactive, RXF-486L 338, 542. Cytotoxic inactive, RXF-944L 338. Cytotoxic inactive, SW1990 123, 126, 991. Cytotoxic inactive, T47D 1035. Cytotoxic inactive, UXF-1138L 338. Cytotoxic inactive, Vero 334. Cytotoxic, 293T 327, 328, 329, 330, 331. Cytotoxic, 3Y1 611. Cytotoxic, 6-MP 19, 19. Cytotoxic, A2780 24, 490, 491, 502, 1109. Cytotoxic, A498 180. Cytotoxic, A549 28, 30, 42, 43, 44, 90, 112, 113, 115, 314, 315, 316, 317, 440, 441, 442, 443, 444, 445, 518, 556, 588, 592, 631, 646, 647, 673, 674, 725, 729, 738, 744, 764, 765, 766, 767, 768, 769, 772, 800, 810, 811, 828, 829, 840, 842, 843, 844, 849, 850, 888, 919, 920, 938, 939, 944, 947, 950, 951, 952, 959, 960, 961, 962, 969, 970, 971, 972, 974, 975, 979, 980, 981, 1003, 1004, 1005, 1021, 1024, 1044, 1046, 1047, 1048, 1050, 1051, 1053, 1055, 1056, 1065, 1098, 1099, 1101, 1105, 1106, 1123, 1124, 1129, 1139. Cytotoxic, A549, using a fraction contained the compound 774. Cytotoxic, ACHN 314, 315, 316. Cytotoxic, anchorage-independent tumour growth inhibitor 866. Cytotoxic, antiproliferative 19, 542, 771. Cytotoxic, B16 121, 122, 124, 125, 904, 905, 906, 907, 908, 909. Cytotoxic, B16-F-10 2, 558. Cytotoxic, BC-1 341. Cytotoxic, BCA-1 637. Cytotoxic, Bel7402 285, 289, 290, 291, 292, 293, 294, 888, 950. Cytotoxic, BGC823 883, 891. Cytotoxic, breast adenocarcinoma cell line 1125.

Cytotoxic, BSC 1055, 1056. Cytotoxic, BSY1 314, 315, 316. Cytotoxic, BXF-1218L 337, 338, 339, 340. Cytotoxic, BXF-T24 337, 339, 340. Cytotoxic, BXPC3 497. Cytotoxic, Ca9-22 762, 763, 945, 1101, 1129, 1130. Cytotoxic, candidaspongiolide A/B 1.7:1.0 mixture 505, 506. Cytotoxic, causes complete loss of filamentous actin with disruption of actin cytoskeleton 469. Cytotoxic, CCRF-CEM 4, 5, 672. Cytotoxic, cell division inhibitor 812, 813. Cytotoxic, CNXF-498NL 337, 338, 339, 340. Cytotoxic, CNXF-SF268 337, 338, 339, 340. Cytotoxic, cultured mouse neuroblastoma cells, causes characteristic rounding 181. Cytotoxic, cultured tumour cell lines 391, 394, 407. Cytotoxic, CXF-HCT116 337, 339, 340. Cytotoxic, CXF-HT29 337, 339, 340. Cytotoxic, DG-75 396, 397, 539, 540. Cytotoxic, disk diffusion soft agar colony formation assay, C38 and L1210, different ZU < 250 64, 65, 66, 85, 86. Cytotoxic, disruption of actin cytoskeleton 472, 478. Cytotoxic, DLD-1 4, 5, 317, 672, 740, 742, 1086. Cytotoxic, DLDH 1016, 1017, 1019, 1112. Cytotoxic, DMS114 314, 315, 316. Cytotoxic, DMS273 314, 315, 316. Cytotoxic, drug sensitive MCF7 671. Cytotoxic, DU145 314, 315, 316, 497, 646, 647, 725, 738, 828, 829. Cytotoxic, E39 777. Cytotoxic, EAC 1122. Cytotoxic, fertilized egg cells of sea urchin Strongyocentrotus intermedius at eight blastomer stage 1057. Cytotoxic, fertilized sea urchin eggs 812, 813, 995. Cytotoxic, GXF-251L 129, 337, 339, 340. Cytotoxic, H460 73. Cytotoxic, HBC4 314, 315, 316. Cytotoxic, HBC5 314, 315, 316. Cytotoxic, HBL100 24, 491. Cytotoxic, HCC2998 314, 315, 316.

Index 5 Compound Pharmacological Activity Index

Cytotoxic, HCT15 314, 315, 316. Cytotoxic, HCT116 64, 78, 127, 128, 289, 290, 291, 292, 293, 294, 305, 306, 308, 314, 315, 316, 386, 387, 391, 392, 393, 490, 507, 508, 555, 558, 814, 815, 856, 965, 1086, 1139. Cytotoxic, HCT116, very potent 472, 478. Cytotoxic, HCT116/VM46 507. Cytotoxic, HEK-293 19, 289, 290, 291, 292, 293, 294. Cytotoxic, HEL 969, 970. Cytotoxic, HeLa 10, 11, 121, 122, 124, 125, 289, 290, 291, 292, 293, 294, 509, 646, 647, 660, 725, 738, 739, 770. Cytotoxic, HeLa-S3 432, 433, 434, 435, 436, 437, 438, 439, 493, 494, 495, 520, 521, 522, 523, 705, 795, 1090. Cytotoxic, Hep3B 850, 841, 845, 848, 835, 840, 847, 1021, 1024. Cytotoxic, HepG 910. Cytotoxic, HepG2 121, 122, 124, 125, 129, 835, 840, 841, 845, 847, 848, 850, 876, 879, 920, 1021, 1024, 1101, 1129. Cytotoxic, HepG2, selective 1021, 1024. Cytotoxic, HepG2, significant potency 479. Cytotoxic, HepG3 879. Cytotoxic, HepG3B 762, 1130, 763, 945, 1129, 1101. Cytotoxic, high active 702. Cytotoxic, HL60 23, 30, 273, 275, 279, 285, 295, 300, 301, 494, 495, 679, 704, 743, 771, 883, 883, 888, 889, 891, 891, 896, 897, 948, 949, 950, 952, 974, 975, 978, 1099, 1105, 1106, 1139. Cytotoxic, HL60, ED50 = 12.0 μg/mL 672. Cytotoxic, hmn epidermoid carcinoma cells 224, 736, 737. Cytotoxic, hmn melanoma cell lines 734, 777, 892. Cytotoxic, hmn non-small cell lung carcinoma 777. Cytotoxic, hmn prostate adenocarcinoma cell line 1125. Cytotoxic, hmn tumour cell lines, demonstrated some cell-line selectivity 203, 204, 205, 206. Cytotoxic, HNXF-536L 337, 338, 339, 340. Cytotoxic, HT29 2, 42, 43, 44, 78, 79, 90, 129, 314, 315, 316, 458, 459, 509, 556, 586,

515

588, 592, 615, 616, 617, 618, 619, 620, 631, 646, 647, 673, 674, 696, 725, 729, 738, 739, 744, 753, 761, 764, 765, 766, 767, 768, 769, 770, 772, 800, 828, 829, 833, 834, 840, 842, 843, 844, 849, 850, 914, 937, 938, 939, 959, 961, 962, 969, 970, 971, 972, 977, 979, 980, 981, 1003, 1004, 1005, 1044, 1046, 1047, 1048, 1050, 1051, 1053, 1055, 1056, 1065, 1098, 1123, 1124. Cytotoxic, HT29, using a fraction contained the compound 774. Cytotoxic, HTCLs cells 974, 975. Cytotoxic, IGROV 646, 647, 725, 738, 739. Cytotoxic, induction of modest apoptosis and arrest in G1 phase of cell cycle 127. Cytotoxic, inhibits cell division in fertilized sea urchin eggs 526. Cytotoxic, inhibits development of fertilised echinoderm eggs 560. Cytotoxic, inhibits hmn epidermoid carcinoma cells 895. Cytotoxic, inhibits MCF7 proliferation 996, 1110, 1128. Cytotoxic, J774.1 327, 328, 329, 330, 331. Cytotoxic, J774.A1 19. Cytotoxic, JB6 P+CI41 660. Cytotoxic, JurKat 2. Cytotoxic, K562 10, 11, 278, 281, 591, 642, 643, 644, 646, 647, 679, 704, 725, 738, 739, 770, 771, 834, 883, 891, 1035, 1086, 1109, 1113, 1116, 1117, 1118, 1120, 1121, 1122, 1122. Cytotoxic, KB 20, 68, 69, 93, 94, 99, 189, 190, 191, 213, 333, 341, 389, 390, 394, 395, 398, 399, 400, 401, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 420, 421, 428, 430, 431, 447, 458, 459, 473, 474, 475, 476, 481, 515, 533, 541, 545, 577, 580, 581, 586, 586, 587, 627, 673, 674, 744, 764, 765, 766, 767, 768, 769, 773, 776, 870, 959, 961, 971, 972, 977, 1044, 1046, 1047, 1048, 1050, 1051, 1053, 1088, 1089, 1090, 1091, 1092, 1093, 1094, 1095, 1096, 1098. Cytotoxic, KB, very potent 474. Cytotoxic, KM12 314, 315, 316. Cytotoxic, KM20L2 497.

516

Index 5 Compound Pharmacological Activity Index

Cytotoxic, KV/MDR 344, 345. Cytotoxic, L1210 8, 9, 20, 68, 69, 93, 94, 99, 213, 217, 389, 390, 391, 394, 395, 398, 399, 400, 401, 402, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 424, 428, 429, 430, 431, 474, 513, 580, 582, 671, 722, 823, 824, 825, 830, 870. Cytotoxic, L1210, inseparable equilibrium mixture of myriaporone 3 and myriaporone 4 32, 33. Cytotoxic, L-6 804, 805, 806, 807, 857, 983, 984, 985, 986, 1032, 1033, 1066, 1067, 1068, 1069, 1070, 1071, 1072, 1073, 1074, 1075. Cytotoxic, LNCaP 646, 647, 725, 738, 739, 770, 834, 1100, 1131. Cytotoxic, LNCaP cells in MEM+10% FBS 890, 1122, 1126, 1127. Cytotoxic, LoVo 515, 533, 545, 577, 627, 646, 647, 725, 738, 739, 770, 834, 1090. Cytotoxic, LoVo-DOX 646, 647, 725, 738, 739, 770, 834. Cytotoxic, LOX 511, 512, 516. Cytotoxic, LOX, mixture with Poecillastrin B 457. Cytotoxic, LOX, mixture with Poecillastrin C 456. Cytotoxic, LOX-IMVI 314, 315, 316, 572, 573, 589. Cytotoxic, LOX-IMVI, candidaspongiolide A/B 1.7:1.0 mixture 505, 506. Cytotoxic, lung carcinoma cell 1100, 1131. Cytotoxic, LXF-1121L 337, 338, 339, 340. Cytotoxic, LXF-289L 337, 339, 340. Cytotoxic, LXF-526L 337, 339, 340. Cytotoxic, LXF-529L 129, 337, 339, 340. Cytotoxic, LXF-629L 337, 339, 340. Cytotoxic, LXF-H460 337, 339, 340. Cytotoxic, M14 572, 573, 589. Cytotoxic, M14, candidaspongiolide A/B 1.7:1.0 mixture 505, 506. Cytotoxic, MAXF-401NL 129, 337, 338, 339, 340, 542. Cytotoxic, MAXF-MCF7 337, 339, 340. Cytotoxic, MCF7 74, 121, 122, 123, 124, 125, 126, 314, 315, 316, 497, 518, 572, 573, 589, 610, 763, 839, 840, 841, 845, 846, 847, 848, 850, 883, 891, 920, 1021, 1024, 1025, 1086, 1099, 1105, 1106, 1129.

Cytotoxic, MCF7 Adr 671. Cytotoxic, MCF7 cells in MEM+10% FBS 890, 1122, 1126, 1127. Cytotoxic, MCF7 cells in MEM+5% DCC-FBS+ 1nM 17β-Estradiol 890, 1122, 1126, 1127. Cytotoxic, MCF7, anti-proliferation 70, 71. Cytotoxic, MCF7, candidaspongiolide A/B 1.7:1.0 mixture 505, 506. Cytotoxic, MCF7, selective 1021. Cytotoxic, MDA-MB-231 314, 315, 316, 588, 840, 841, 845, 847, 848, 850, 919, 920, 945, 1021, 1024, 1025, 1086, 1101, 1129. Cytotoxic, MDA-MB-231, anti-proliferation and inhibition of migration 70, 71. Cytotoxic, MDA-MB-435 468. Cytotoxic, MEL28 42, 43, 44, 556, 592, 729, 772, 828, 829, 840, 842, 843, 844, 849, 850, 938, 939, 979, 981. Cytotoxic, MEL28, using a fraction contained the compound 774. Cytotoxic, melanoma, e.g. UACC62 562. Cytotoxic, MES-SA 518. Cytotoxic, MES-SA/DX5 518. Cytotoxic, MEXF-276L 337, 338, 339, 340. Cytotoxic, MEXF-394NL 337, 338, 339, 340. Cytotoxic, MEXF-462NL 129, 337, 339, 340. Cytotoxic, MEXF-514L 337, 339, 340. Cytotoxic, MEXF-520L 337, 338, 339, 340. Cytotoxic, MKN1 314, 315, 316. Cytotoxic, MKN7 314, 315, 316. Cytotoxic, MKN28 314, 315, 316. Cytotoxic, MKN45 314, 315, 316. Cytotoxic, MKN74 314, 315, 316. Cytotoxic, MMOA: - microtubule depolymerizer 172, 177, 182, 183, 184, 196, 197, 198. Cytotoxic, Molt4 511, 512, 516, 1016, 1017, 1019, 1035, 1086, 1112. Cytotoxic, multidrug-resistant NCI-ADR 518. Cytotoxic, mus neuroblastoma cells 89, 101. Cytotoxic, NCI-ADR-Res 317, 440, 441, 442, 443, 444, 445. Cytotoxic, NCI-H23 314, 315, 316. Cytotoxic, NCI-H226 314, 315, 316. Cytotoxic, NCI-H460 64, 65, 66, 78, 79, 85, 86, 121, 314, 315, 316, 468, 497, 547, 548, 572, 573, 589. Cytotoxic, NCI-H460, candidaspongiolide A/B 1.7:1.0 mixture 505, 506. Cytotoxic, NCI-H522 314, 315, 316, 493.

Index 5 Compound Pharmacological Activity Index

Cytotoxic, neuro-2a 64, 65, 66, 78, 79, 85, 86, 468, 547, 548. Cytotoxic, neuroblastoma cells through Nachannel activating potency was one third that of PbTx-3 MLD ddy mus ip 149. Cytotoxic, NSCLC-L16 662, 663. Cytotoxic, NSCLC-N6 458, 459, 502, 503, 680, 711, 776. Cytotoxic, NSCLC-N6-L16 586, 586, 587. Cytotoxic, OVCAR-3 180, 314, 315, 316, 497. Cytotoxic, OVCAR-4 314, 315, 316. Cytotoxic, OVCAR-5 314, 315, 316. Cytotoxic, OVCAR-8 314, 315, 316. Cytotoxic, OVXF-899L 337, 339, 340. Cytotoxic, OVXF-1619L 337, 339, 340. Cytotoxic, OVXF-OVCAR3 337, 339, 340. Cytotoxic, P388 18, 23, 27, 28, 42, 43, 44, 67, 68, 90, 94, 95, 96, 97, 100, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 158, 169, 170, 171, 172, 173, 174, 175, 176, 178, 180, 180, 183, 187, 188, 193, 194, 195, 213, 232, 278, 281, 285, 289, 290, 291, 292, 293, 294, 301, 317, 370, 371, 373, 374, 382, 383, 384, 400, 458, 459, 497, 502, 517, 527, 556, 557, 586, 586, 587, 592, 625, 631, 673, 674, 679, 696, 704, 723, 729, 740, 741, 742, 743, 744, 764, 765, 766, 767, 768, 769, 772, 800, 828, 829, 836, 840, 842, 843, 844, 849, 850, 871, 880, 881, 883, 888, 889, 891, 896, 896, 897, 903, 912, 917, 922, 923, 924, 938, 939, 946, 948, 949, 950, 951, 952, 959, 961, 962, 969, 970, 971, 972, 977, 979, 981, 1000, 1001, 1002, 1003, 1004, 1005, 1044, 1046, 1047, 1048, 1050, 1051, 1053, 1055, 1056, 1090, 1098, 1108, 1123, 1124, 376. Cytotoxic, P388, using a fraction contained the compound 774. Cytotoxic, P388/Dox 458, 459, 586. Cytotoxic, P388D1 771. Cytotoxic, P388D1, ED50 = 10.4 μg/mL 672. Cytotoxic, PANC1 317, 440, 441, 442, 443, 444, 445, 646, 647, 725, 738, 739, 770, 834. Cytotoxic, panel of 4 hmn tumour cell lines and 2 murine mast cell lines 455. Cytotoxic, panel of 8 tumour cell lines 1054. Cytotoxic, panel of 12 hmn tumour cell line, mean IC50 = 0.022 μmol/L, range IC50 = 0.007~0.058 μmol/L 127.

517

Cytotoxic, panel of 12 hmn tumour cell lines, mean IC50 = 3.5 μmol/L, range IC50 = 1.0~4.4 μmol/L 128. Cytotoxic, panel of 36 hmn tumour cell lines 337, 340. Cytotoxic, panel of 36 hmn tumour cell lines, mean IC50 =30.06 μmol/L 338. Cytotoxic, panel of 36 hmn tumour cell lines, mean IC50 =6.09 μmol/L 339. Cytotoxic, panel of 39 hmn tumour cell lines, HCC panel, mean GI50 = 0.60 μmol/L 493. Cytotoxic, panel of 39 hmn tumour cell lines, mean Log10 GI50 mol/L = –5.75 314. Cytotoxic, panel of 39 hmn tumour cell lines, mean Log10 GI50 mol/L = –5.72 315. Cytotoxic, panel of 39 hmn tumour cell lines, mean Log10 GI50 mol/L = –5.93 316. Cytotoxic, panel of 39 hmn tumour cell lines, mean Log10 GI50 mol/L = –6.31 535. Cytotoxic, panel of 39 hmn tumour cell lines, mean Log10 GI50 mol/L = –6.67 536. Cytotoxic, panel of 39 hmn tumour cell lines, mean Log10 GI50 mol/L = –6.11 537. Cytotoxic, panel of 39 hmn tumour cell lines, mean Log10 GI50 mol/L = –6.28 538. Cytotoxic, panel of NCI’s 60 cell lines 562. Cytotoxic, panel of NCI’s 60 hmn tumour cell lines, mean GI50 = 1.17×10-10 mol/L, against a subset of highly chemoresistant tumour types, e.g. HL60, SR, NCI-H226, NCI-H23, NCI-H460, NCI-H522, DMS114, and DMS273, HCT116, HT29, KM12, KM20L2 and SW620, SF539, U251, SK-MEL -5, OVCAR-3, and RXF-393 579. Cytotoxic, panel of NCI’s 60 hmn tumour cell lines, mean GI50 = 1.02×10-10 mol/L 582. Cytotoxic, panel of NCI’s 60 hmn tumour cell lines, mean GI50 = 1.23×10-10 mol/L 583. Cytotoxic, panel of NCI’s 60 hmn tumour cell lines, mean GI50 = 2.4×10-8 mol/L 510. Cytotoxic, panel of NCI’s 60 hmn tumour cell lines, mean Log10 GI50 mol/L = –8.00 477. Cytotoxic, panel of NCI’s 60 tumour cell lines, mean GI50 = 7×10-10 mol/L 178. Cytotoxic, panel of NCI’s tumour cell lines, mean Log10 IC50 mol/L = –6.5 460. Cytotoxic, panel of NCI’s tumour cell lines, mean Log10 IC50 mol/L = –8.1 465.

518

Index 5 Compound Pharmacological Activity Index

Cytotoxic, panel of NCI’s tumour cell lines, mean Log10 IC50 mol/L = –7.2 466. Cytotoxic, panel of NCI’s tumour cell lines, mean Log10 IC50 mol/L = –6.2 467. Cytotoxic, panel of NCl’s hmn tumour cell lines, mean GI50 = 1.15×10–10 mol/L 187. Cytotoxic, panel of NCl’s hmn tumour cell lines, mean GI50 = 1.38×10–10 mol/L 172. Cytotoxic, panel of NCl’s hmn tumour cell lines, mean GI50 = 1.58×10–10 mol/L 183. Cytotoxic, PAXF-1657L 129, 337, 339, 340, 542. Cytotoxic, PAXF-PANC1 337, 339, 340. Cytotoxic, PC3 314, 315, 316, 949. Cytotoxic, PLA2 742. Cytotoxic, potent 496. Cytotoxic, prostate tumour cells 1138. Cytotoxic, PRXF-22RV1 337, 339, 340. Cytotoxic, PRXF-DU145 337, 339, 340. Cytotoxic, PRXF-LNCAP 337, 339, 340. Cytotoxic, PRXF-PC3M 337, 339, 340. Cytotoxic, PS (= P388) 376, 377, 378, 379, 735. Cytotoxic, PXF-1752L 337, 338, 339, 340. Cytotoxic, RXF-1781L 337, 339, 340. Cytotoxic, RXF-393NL 337, 339, 340. Cytotoxic, RXF-486L 129, 337, 339, 340. Cytotoxic, RXF-631L 314, 315, 316. Cytotoxic, RXF-944L 337, 339, 340. Cytotoxic, several HTCLs 75, 346, 347, 348. Cytotoxic, SF268 314, 315, 316, 497. Cytotoxic, SF295 180, 314, 315, 316, 497. Cytotoxic, SF539 314, 315, 316. Cytotoxic, SKBR3 646, 647, 725, 738, 739, 770, 834. Cytotoxic, SK-MEL-5 180. Cytotoxic, SK-MEL-5, potent 598. Cytotoxic, SK-MEL-28 646, 647, 725, 738, 739, 770, 834. Cytotoxic, SK-OV-3 314, 315, 316, 513, 1099, 1105, 1106. Cytotoxic, SMMC-7721 904, 905, 906, 907, 908, 909. Cytotoxic, SNB75 314, 315, 316. Cytotoxic, SNB78 314, 315, 316, 493. Cytotoxic, St4 314, 315, 316. Cytotoxic, SW1573 24, 491. Cytotoxic, SW1990 121, 122, 124, 125. Cytotoxic, T47D 24, 491, 1086.

Cytotoxic, ten fold greater cytotoxicity than diskodermolide for majority of tumour cell lines, and has virtually no drop in potency in multi-drug resistant tumour cell lines 518. Cytotoxic, tumour cell lines, nanomolar 470. Cytotoxic, U251 314, 315, 316. Cytotoxic, U937 1099, 1105, 1106. Cytotoxic, UACC-257 572, 573, 589. Cytotoxic, UACC-257, candidaspongiolide A/B 1.7:1.0 mixture 505, 506. Cytotoxic, UT7 576, 591. Cytotoxic, UXF-1138L 337, 339, 340. Cytotoxic, various HTCLs 1132. Cytotoxic, Vero 332, 333, 341. Cytotoxic, weak 40, 385, 787. Cytotoxic, WEHI-164 15, 16, 19. Cytotoxic, WiDr 24, 491. Cytotoxic, works through polymerization of tubulin and stabilization of microtubules 518. D Different mechanism of tumour growth inhibition from that of conventional antitumour agents 510. Disrubts cholesterol-containing lipid membranes 135, 136. Disrupts actin cytoskeleton 458, 461, 462, 463, 464, 459, 465. Disrupts actin cytoskeleton to rapidly sever F-actin 474. Disrupts actin cytoskeleton, inhibits polymerization of G-actin and depolymerizes F-actin in concentrationdependent fashion 470. DNA polymerase α inhibitor 7. DNA polymerase β inhibitor 7. Dopamine β-hydroxylase inhibitor 120. E Ecdysone, may act to protect the alga from crustacean predators 809. Elastase release inhibitor 672. Elastase release inhibitor, stimulated hmn neutrophils, response to fMLP/CB 1018. Emollient 710. Endo-β-1, 3-glucanases L0 inhibitor 867. Endo-β-1, 3-glucanases LIV4 inhibitor 867. Enzyme inhibitor 226, 227.

Index 5 Compound Pharmacological Activity Index

Estrogen-receptor binder, displacing estradiol in competitive manner, altering estrogen responsive gene expression 1132. F Farnesyl-protein transferase inhibitor 597. Feeding deterrent 893. G Glutamate toxicity inhibitor, neuronal hybridoma N18-RE-105 cells 270. Glutamate-induced tubulin polymerization inhibitor, potent 584, 585. H Haemolytic 138, 139, 140, 143, 144, 929. Hemolytic 141, 207, 208, 629. Hemolytic, hmn erythrocytes, several hundred times more efficacious than positive control saponin 134. Hemolytic, hmn red blood cells 137. Hemolytic, mouse blood cells 133. Hemolytic, mouse-erythrocytes 681, 693, 1020. Hepatotoxin 447. Herbicide 309. Highlighting its pharmacological potential in treatment of liver disorders 1079. Highly toxin 201. Histone acetyltransferase [h]p300 inhibitor, indicating the steric importance of 9-OH 1143, 1144. HIV-1 induced cytopathic effect inactive, MT-2 cells 677. HIV-1 integrase inhibitor 745, 954, 955. HIV-1 protease inhibitor 677. HIV-1 reverse transcriptase inhibitor 1041. Hypnotic 990. Hypoglycemic, aldose reductase inhibitor, RLAR 982. Hypotensive 819. Hypotensor 994. I Ichthyotoxic 83, 208, 675, 678, 929. Ichthyotoxic, fish 87, 85, 86. Ichthyotoxin 25, 26, 146, 147, 153, 154, 155, 162, 202, 207, 213, 447, 448, 449, 606, 639, 760.

519

Ichthyotoxin, component toxin of shellfish poisoning 446. IL-6 production inhibitor, stimulated bone marrow-derived dendritic cells 626, 670. Immunohaemolysis inhibitor 918. Immunophilin FKBP12-binding agent 388. Immunopotentiator 918. Immunosuppressive 796. Important biochemical probe to study actin dynamics 470, 474. Increases in cells percentage in sub-G1 fraction 271, 272, 273, 274, 277, 280, 282, 295, 300. Inducer of apoptosis, A549, HCT116 and HL60 1139. Inducer of PXR transactivation, with no effect on FXR 1140. Induces activation of p38 kinase and JNK 94, 103. Induces apoptosis with increased cytosolic Ca2+ concentration in HeLa-S3 Cells 494. Induces apoptosis, Ehrlich cell 808. Induces avoidance reaction, sea urchin Strongylocentrotus nudus 708. Induces conversion of tumour associated macrophages from M2 to M1 phenotype 612. Induction of apoptosis 965. Inhibited binding of radiolabeled vinblastine and GTP to tubulin 172, 178, 183. Inhibited tubulin polymerization 178. Inhibiting colony formation, reduced colony number 761, 833, 937. Inhibitior of IL-6 production 826. Inhibitior of IL-12 production 826. Inhibitior of p40 production 826. Inhibitior of TNF-a production 826. Inhibitor of ubiquitin Ubc13-Uev1a complex potential as anticancer agent 854, 855. Inhibitor of vacuolar ATPase 562. Inhibits anti-IgE-induced release of histamine rat peritoneal mast cells 823, 824. Inhibits bacterial quorum sensing, reporter gene assay 78, 79. Inhibits binding of Brevetoxin-3 to voltagesensitive sodium channels rat brain synaptosomes 157.

520

Index 5 Compound Pharmacological Activity Index

Inhibits Ca2+ influx into mouse splenocytes 808. Inhibits cancer cell proliferation with a novel mechanism 493. Inhibits cell growth 555, 679, 704, 731. Inhibits cell growth, KV/MDR 344. Inhibits colony formation of tumour cells 787. Inhibits expression in HUVEC models 142. Inhibits gastrulation of starfish Asterina pectinifer embryos 318, 319, 320. Inhibits growth 881, 923, 924. Inhibits growth of HL60 cells by Induction of apoptosis 1099, 1105, 1106. Inhibits guanosine diphosphate/G-protein RAS exchange 803. Inhibits KV/MDR growth 345. Inhibits phorbol ester-stimulated adherence of EL-4 and IL-2, mouse thymoma cells 440. Inhibits sea urchin egg fertilization, compoundpreincubated sperm of sea urchin Strongylocentrotus nudus 684, 697, 783, 784, 785, 786. Inhibits settlement of biofouling alga Hincksia irregulatus 755, 756, 757. Insecticide 309, 311, 487. Interaction with actin, inhibited polymerization of G-actin to polymer fibrous F-actin 432. Interaction with actin, severed depolymerized F-actin to G-actin 432. Interaction with actin, to form 1:1 complex with monomer G-actin 432. Ionophoric agent 213. Iron chelating activity 362. Irritant 247. Isocitrate lyase inhibitor, Candida albicans 117. K Kinases inhibitor, CDK4/cyclin D1 604. Kinases inhibitor, EGFR 604. Kinases inhibitor, PKC-ε 604. L Larvicide 675, 678. LD mus 185. LD mus ip 451. LD50 brine shrimp 84, 91. LD50 brine shrimp Artemia salina 836. LD50 crab 132. LD50 cytotoxicity 352, 353, 354, 355, 356, 357, 358, 359, 360, 361.

LD50 goldfish 84. LD50 Leishmania mexicana promastigotes 11, 14. LD50 microalgal toxin 236. LD50 mus 220. LD50 mus ip 141, 192, 224, 230, 231. LD50 mus ip, acute toxicity 229, 232. LD50 mus ipr 120, 132, 186, 201, 211, 212, 247, 497, 519, 567, 590, 816. LD50 mus iv 132. LD50 mus ivn 120, 213. LD100 barnacle Balanus amphitrite cyprid larvae 635, 636, 638, 727. LD100 mus ip 244. Less toxic to mammals than other pinnatoxins 232. Lethal toxic, crayfish Procambarus clarkia 70, 72. Lethality, brine shrimp 1119. Lethality, mouse 158. Low toxic, much less toxic than other known cyclic imine toxins 578. M May be a new structural class for cancer therapeutics research 510. May play ecological role in preventing microbial fouling in body wall surfaces of starfish Acodontaster conspicuus 698, 861, 863, 911, 1036, 1037, 1038, 862. MEK kinase inhibitor 341. Microalgal toxin 214, 216, 223, 228, 236, 238, 240, 241, 242. Microtubule stabilizer 524. Might possess beneficial therapeutic potential against drug-resistant tumours 344, 345. MLD mus ip 148. Modulator of PKC 366. Molluscacidal 790. Molluscacidal, snail vector Biomphalaria glabrata 3. Molluscacidals play a critical role in control of schistosomiasis transmission 3. Morphological differentiation inhibitor 365. Moulting hormone 648. Moulting hormone, crustacean 837. Moulting hormone, insects, very high 838. MT1-MMP inhibitor 935, 936. Muscle contraction inhibitor 719, 720. Mycotoxin 260, 268, 269.

Index 5 Compound Pharmacological Activity Index

N Na/K-ATPase inhibitor 132. Na1+ channel activator 147. Na1+ channel activator, binding quasiirreversibly to site 5 on VSSC 159. Nematocidal 98. Nematocide 482, 483, 484, 485. Nephrotoxin 447. Nervous system activity, neurite outgrowth inducer 788, 789. Nervous system activity, neurite outgrowth inducer, MMOA: - dependent on xylose on side chain 957, 958, 1058, 1059, 1060. Neuraminidase inhibitor 818. Neurite outgrowth enhancer, rat pheochromocytoma PC12 cells 596. Neuritogenesis inducer, neuroblastoma neuro2a cells 622, 623. Neurotoxin 146, 154, 155, 162, 202. Neurotoxin 192. O Oocyte-lytic activity, non-selectively lyses immature starfish oocytes Asterina pectinifera, lysed both oocyte’s plasma membrane and nuclear envelope 10. Ornithine decarboxylase induction inhibitor 38, 39. P Paralytic phycotoxin 519. Pharmaceutical aid emulsifying agent 710. Pharmacology, bryostatin 1 is emblematic of marine drugs potential, since it is exploited in non-correlated different diseases including cancer, HIV and neurodegenerative diseases 366. Phosphatase PP1 inhibitor 221, 222. Phosphatase PP2A inhibitor 220, 221, 222. Phosphatases PP1 inhibitor 220. Phycotoxin 31, 192, 213, 237, 450, 451, 574. Phytotoxic 364. Phytotoxin 514, 915. Pigment 283. PK activator 192. PKC binding agent 370. PKC inhibitor 440.

521

PKC ξ inhibitor 749, 750. PKCs inhibitor, PKCα, βI, βII, γ, δ, ε, η and ξ 996, 1110, 1128. PLA2 inhibitor 1113, 1120. Polyether marine toxin 148, 150, 151. Polymorphonuclear leucocyte activator 370. Potassium ion membrane transporter 48. PP inhibitor, serine/threonine-specific 215. PP2A inhibitor 225. Promotor of tubulin assembly, similar to paclitaxel and diskodermolide 518. Protein phosphatase 1 and 2A inhibitors, MMOA: - okadaic acid binding to proteins OABP1 and OABP2 224. Protein phosphatase inhibitor 213. Protein phosphorylation stimulator 370. Protein tyrosine kinase inhibitor 707. PTK inhibitor 692, 695. PXR agonist 874, 875. PXR agonist and FXR antagonist 873. PXR agonists 640, 641. PXR agonist/farnesoid-xreceptor antagonist 1079. R Reversal of MDR, KB-3-1 649, 650, 651, 652, 864, 865, 1039. Reversal of MDR, KB-C2 649, 650, 651, 652, 864, 865, 1039. Reversal of MDR, KB-CV60 649, 650, 651, 652, 864, 865, 1039. Reverses fluconazole resistance, multidrugefflux resistant fungi 735. RNA biosynthisis inhibitor 378. S Sedative 990. Shellfish toxin 447, 448, 449, 450, 452, 453, 454. Siderophore 362, 363. Signal transduction agent 440. Smooth muscle contractant, showing tetrodotoxin-like effect 229. Smooth muscle contractor 213. Sodium channel activation, neuro-2a 73. Sodium channel activator, binding quasiirreversibly to site 5 on the voltage sensitive Sodium channel VSSC 160.

522

Index 5 Compound Pharmacological Activity Index

Sodium channel blocker neuro-2a cells without appreciable cytotoxicity 563. Sperm motility inhibitor 132. Spore germination inhibitor 63. Starfish fertilisation inhibitor 929. Stimulates superoxide production, rbt neutrophils 628, 630. Stimulator steroidogenesis, fluorometrically steroidogenesis assay, primary cultured bovine adrenocortical cells 376. Synergistic cytotoxicity, for paclitaxel 810, 811. T Taq DNA polymerase inhibitor 677. Thallium and Potassium ions used in ammonium-specific electrodes, selectively complexes with ammonium 48. Thrombin inhibitor 758, 831, 832, 929, 930, 931. Toxic 211, 226, 227, 232, 237. Toxic, brine shrimp 3, 17, 34, 35, 85, 86, 87, 91, 376, 566, 685, 754, 759, 989, 1114, 1115. Toxic, brine shrimp Artemia salina 260, 262, 263, 266, 868. Toxic, causes ciguatera food poisoning, Gambierdiskus toxicus is the primary cause 199. Toxic, causes hmn intoxication when eating tropical reef fishes such as moray eels 199. Toxic, constituent of scallops 212. Toxic, diarrhetic shellfish poisoning 218, 219. Toxic, fast-acting 575. Toxic, fertilized sea urchin egg assay 376. Toxic, hmn intoxication 570. Toxic, in vivo, mice, lethal over a very short time period and also caused limb paralysis 45. Toxic, lagest 3422Da and most lethal Toxin, one of most potent non-proteinaceous toxins 192. Toxic, lethal to brine shrimp 676, 701, 703, 726. Toxic, major toxic metabolite 255. Toxic, mice from bivalve Pteria penguin 233, 234, 235.

(The End of HAMNP Volume 5)

Toxic, most active member of pinnatoxin family 230. Toxic, most lethal non-proteinous toxin 132. Toxic, potent effects on neuronal network integrity in cerebellar cells, ultimately resulting in cell death 492. Toxic, primary rat hepatocytes 134, 30. Toxic, shellfish poisoning, highly 229. Toxin 145, 152, 156, 161, 163, 168, 181, 239, 243, 244, 245, 246, 247, 248, 249, 250, 251, 254, 256, 257, 567, 568, 569, 571. Toxin, causes ciguatera food poisoning 159, 160. Toxin, fish 497. Toxin, most active member of pinnatoxin family 231. Tubulin polymerisation inhibitor 179, 187. Tumour promoter 247, 243. Tumour promotor 226, 227. Type L-Ca2+ channel activator 237, 239. U Undergoing preclinical trials at U.S. Natl. Cancer Inst. 1994 172. Upregulats PPARs transcription HepG2, dose-dependent 856. Upregulats PPARs transcription, HepG2 631, 916. V Vasoconstrictor 593, 594. Vasoconstrictor, coronary 132. VGSC activation activity 64, 66, 78. VGSC activation activity inactive 64, 66, 78. VGSC blocking activity 65, 66, 83, 85. VGSC blocking activity inactive 65, 66, 83, 85. Voltage-dependent N-type Ca2+ channel activator, MMOA: - cyclooxygenase 1 inhibitor 118. α α-2,3-Sialyltransferase inhibitor, rat liver 70, 71.