Handbook of Active Marine Natural Products: Volume 7 O-Heterocycles and Aromatics 9783110655810, 9783110654011

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

Volume : Aliphatic Metabolites 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 7: O-Heterocycles and Aromatics

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

ISBN 978-3-11-065401-1 e-ISBN (PDF) 978-3-11-065581-0 e-ISBN (EPUB) 978-3-11-065416-5 Library of Congress Control Number: 2019941348 Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.dnb.de. © 2019 Walter de Gruyter GmbH, Berlin/Boston Typesetting: Integra Software Services Pvt. Ltd. Printing and binding: CPI books GmbH, Leck Cover image: Science Photo Library/Douwma, Georgette www.degruyter.com

Preface The English edition Handbook of Active Marine Natural Products (HAMNP) with 8 Volumes is a selective version of the Marine Natural Products Dataset. The whole dataset was collected and developed by the Molecular Design Group, Institute of Process Engineering, Chinese Academy of Sciences during 1998–2016. Totally, it covers 19,722 entries of secondary metabolites from marine living things, where 8,350 compound entries have pharmacological activity data. The 8,350 compound entries were arranged into eight volumes to form the set of handbooks as follows: Volume 1: Terpenoids, Part 1 Volume 2: Terpenoids, Part 2 Volume 3: Alkaloids, Part 1 Volume 4: Alkaloids, Part 2 Volume 5: Polyketides and Steroids Volume 6: Aliphatic Metabolites Volume 7: O-Heterocycles and Aromatics Volume 8: Peptides and Others This set of eight HAMNP books gathers the structure, origin, and bioactivity, as well as other relevant information, of 8,350 active marine natural products from 3,025 marine organisms. The HAMNP 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 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 https://doi.org/10.1515/9783110655810-201

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information 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 XIX List of Abbreviations and Acronyms XXIII List of Cancer Cell Codes XXXIII 1

2

Oxygen Heterocycles 1 1.1 β-Lactones 1 1.2 Furans 2 1.3 Butanolides 6 1.4 Pyrans 25 1.5 2-Pyrones (Pyranones; Pentanolides) 1.6 Nonadrides 52 1.7 4-Pyrones (γ-Pyrones) 52 1.8 Spiroketals 66 Aromatic Metabolites 81 2.1 Simple Benzene Derivatives 81 2.2 Diaryl Derivatives 117 2.3 Tropolone Derivatives 207 2.4 Benzofuranoids 208 2.5 Benzopyranoids 215 2.6 Flavonoids 258 2.7 Tannin Glucose 259 2.8 Neolignans 260 2.9 Naphthalene Derivatives 261 2.10 Anthracene Derivatives 292 2.11 Extended Quinones 315 2.12 Phenalenes 316 2.13 Acenaphthalenes 318 2.14 Miscellaneous Polycyclic Aromatics

27

319

Index 1 Compound Name and Synonym Index 329 Index 2 Compound Molecular Formula Index 343 Index 3 Compound Organism Source Index 362 Index 4 Compound Sampling Geographic Locality Index 370 Index 5 Compound Pharmacological Activity Index 373

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/10.1515/9783110655810-202

Introduction The Handbook of Active Marine Natural Products covers eight volumes. This book is Volume 7: O-Heterocycles and Aromatic, which includes 951 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 951 for volume 7) 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 951 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 331 (+)-Aeroplysinin 1 is O Br

Br

HO HO

N

https://doi.org/10.1515/9783110655810-203

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

Source Terms The source data of compound 331 (+)-Aeroplysinin 1 is Source: Sponge Aplysina aerophoba [Syn. Verongia aerophoba], Sponge Aplysina archeri, Sponge Aiolochroia crassa, Sponge Verongula rigida, Sponge Psammaplysilla purpurea, Sponge Ianthella sp. The format is as follows (banding the English-type name and the Latin name together): Source: English-type name + Latin name of source 1, English-type name + Latin name of source 2, English-type name + Latin name of source 3, English-type name + Latin name of source 4, English-type name + Latin name of source 5, English-type name + Latin name of source 6.

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 331 (+)-Aeroplysinin 1, a set of multiple biodata is presented as follows: Pharm: Antibacterial (Photobacterium phosphoreum, IC50 = 3.5 μmol/L);

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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)

antimicroalgal (marine microalgae Coscinodiscus wailesii, IC50 = 5.6 μmol/L, Prorocentrum minimum, IC50 = 7.0 μmol/L); antiviral (HIV-1, IC50 = 14.6 μmol/L); anti-angiogenic (EVLC-2 cell line, 2.5 μmol/L, target MMP-2, effect decrease; HUVEC cell line, 2.5 μmol/L, target MMP-2, effect decrease; RF-24 cell line, 2.5 μmol/L, target MMP-2, effect decrease; BAEC cell line, 3 μmol/L, target MMP-2, effect decrease; BAEC cell line, 3 μmol/L, target PA, effect decrease; BAEC cell line, 3 μmol/L, target PAI, effect increase); anti-inflammatory (HUVEC cell line, 10 μmol/L, target MCP-1, effect decrease; HUVEC cell line, 10 μmol/L, target TSP-1, effect decrease; HUVEC cell line, 10 μmol/L, target COX-2, effect decrease; HUVEC cell line, 20 μmol/L, target Il-1α, effect decrease; HUVEC cell line, 20 μmol/L, target MMP-1, effect decrease);

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apoptogenic (BAEC cell line, 10 μmol/L, target Cleaved lamin-A, effect increase; BAEC cell line, 10 μmol/L, target Caspase-2, -3, -8, -9, effect increase; BAEC cell line, 10 μmol/L, target Cytochrome C, effect increase in cytoplasm; HUVEC cell line, 10 μmol/L, target p-Bad, effect increase); anti-angiogenic (HUVEC (hmn umbilical vein endothelial cells), IC50 = 4.7 μmol/L; EVLC-2 (SV40 large T-antigen immortalized hmn umbilical vein cells), IC50 = 3.0 μmol/L; RF-24 (papillomavirus 16 E6/E7 immortalized hmn umbilical vein cells), IC50 = 2.8 μmol/L; HMEC (hmn microvascular endothelial cells), IC50 = 2.6 μmol/L; BAEC (bovine aortic endothelial cells,), IC50 = 2.1 μmol/L); cytotoxic (HT1080, IC50 = 2.3 μmol/L, HTC116, IC50 = 4.7 μmol/L, HeLa, IC50 = 3.0 μmol/L, THP-1, IC50 = 10.0 μmol/L, NOMO-1, IC50 = 17.0 μmol/L, HL60, IC50 = 5.0 μmol/L); antibiotic (Gram-positive bacteria and several dinoflagellate microalgae causing toxic blooms); EGFR inhibitor (IC100 = 0.5 μmol/L); antitumor (strong effect on EGFR tumor cell lines, blocking proliferation of EGFR-dependent hmn breast cancer cell lines MCF7 and ZR-75-1); molluscacidal; Note: (+)-Aeroplysinin 1 has a wide spectrum of bioactivities. In preclinical studies, it has been shown to have promising anti-inflammatory, antiangiogenic and antitumor effects. It might have a pharmaceutical interest for the treatment of different pathologies. The format is as follows: Pharm: Term name 1 (formatted detail information) Term name 2 (formatted detail information) Term name 3 (formatted detail information) Term name 4 (formatted detail information) Term name 5 (formatted detail information) Term name 6 (formatted detail information) Term name 7 (formatted detail information) Term name 8 (formatted detail information) Term name 9 (formatted detail information) Term name 10 (formatted detail information) Term name 11 (formatted detail information) Term name 12 (formatted detail information) (Note: if any) Under the term name Cytotoxic, a set of multiple cytotoxic biodata is presented as follows:

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cytotoxic ( HT1080, IC50 = 2.3 μmol/L, HTC116, IC50 = 4.7 μmol/L, HeLa, IC50 = 3.0 μmol/L, THP-1, IC50 = 10.0 μmol/L, NOMO-1, IC50 = 17.0 μmol/L, HL60, IC50 = 5.0 μmol/L); EGFR inhibitor, IC100 = 0.5 μmol/L; MCF7 and ZR-75-1 (blocking proliferation) The format is as follows: Term name (in vitro/in vivo, target cancer cell 1, quantitative data, target cancer cell 2, quantitative data, target cancer cell 3, quantitative data, target cancer cell 4, quantitative data, target cancer cell 5, quantitative data, target cancer cell 6, quantitative data, 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 explanation of these codes, please see “List of Cancer Cell Codes.” By means of the formatted and structuralized methods, we normalized expressions of almost all the pharmacological data presented in the books. For complete information in volume 7, of all 959 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

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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 close friends. They gave my MNP project continual concerns and supports for years: Dr. Jun Xu, Professor and Director, Research Center for Drug Discovery, Sun Yet-Sen University, 132 East Circle, University City, Guangzhou, 510006, China, and Dr. Leming Shi, Professor and Director, Center for Pharmacogenomics, School of Life Sciences and Shanghai Cancer Center, Fudan University, Shanghai 200438, China ([email protected]). Third, I like to give my honest thanks to my following group members. For many years, all of them gave various devices to me: 1 Dr. Jing Lei, Associate Professor, Educational Equipment Research and Development Centre, Ministry of Education of the People’s Republic of China, Beijing 100080, China (early research in her doctor thesis) 2 Dr. Bing Liu, Lead Dev Prophix Software Inc. 350 Burnhamthorpe Road West, Suite 1000 Mississauga, Ontario L5B 3J1, Canada (data collection in the early stage) 3 Master Yingxin Qiao, Software Engineer, National Library of China, Beijing 100081, China (data source searching and original paper collection) 4 Dr. Haibo Liu, Associate Professor, The Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Beijing 100193, China (special software development for automatic edition) 5 Dr. Tao Peng, Associate Professor, College of Robotics, Beijing Union University, Beijing 1001011, China (special software development for index generation) 6 Dr. Aihua Xie, Associate Professor, School of Pharmacy, Hebei Chinese Medical University, Shijiazhuang, Hebei 050200, China (part of data collection) 7 Dr. Chenzhong Liao, Professor, Dean of Department of Pharmacy, School of Biological and Medical Engineering, Hefei University of Technology, Hefei 230009, China (original paper collection) 8 Dr. Jianfeng Pei, Associate Professor, Center for Quantitative Biology, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871, China (data collection in the early stage) 9 Dr. Xianfeng He, Associate Professor, Scientific Researcher, EMMS Group, State Key Laboratory of Multiphase Complex Systems, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China (data collection in the early stage) 10 Madam Guirong Xie, Associate Professor, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China (part of data compilation) 11 Mr. Wucheng Tang, Engineer, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China (part of original paper collection)

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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

R02

R03 R04 R05

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 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 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 CRC Press, Dictionary of Natural Products on DVD, version 20.2, 2012 Jean-Michel Kornprobst, Encyclopedia of Marine Natural Products, Vol. 1–Vol. 3, 2nd Edition, WILEY BLACKWELL, Germany, 2014

(Dictionaries 17) R06 R07 R08 R09 R10 R11 R12 R13 R14 R15 R16 R17

P.M. Kirk, P.F. Cannon, D.W. Minter and J.A. Stalpers, Dictionary of the Fungi, 10th Edition, CABI Europe-UK, 2011 Miaoying Cai, et al., Names of Bacteria, 2nd Edition, Science Press, Beijing, 1996 Rui-Fu Yang et al, Dictionary of Bacterial Names with English Explanation and Chinese Translation, Chemical Industry Press, Beijing, 2011 Zongxun Wang et al. (Institute of Botany, Chinese Academy of Sciences), New Edited Plant Names in Latin-Chinese-English, Aerial Industry Press, Beijing, 1996 Zhong-Yan Qi and Xi-Xing Liu, New Names of Invertebrate Animals in Latin-Chinese, Science Press, Beijing, 1999 Ling-Ti Lu and Jia-Ran Zhu, Dictionarium Lantino-Sinicum de Scientia et technologia, The Commercial Press, Beijing, 2017 Ji-Sheng Chen, et al., English-Chinese Dictionary of Life Science, Scientific and technological Literature Press, Beijing, 1992 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 Scientific Terms Laboratory of Science Press, English-Chinese Dictionary of Chemistry and Chemical Engineering, 4th Edition, Science Press, Beijing, 2000 Scientific Terms Laboratory of Science Press, English-Chinese Dictionary of Chemistry and Chemical Engineering, 5th Edition, Science Press, Beijing, 2016 Jian Zhuge and Zheng-Xiang Wang, Modern English-Chinese Dictionary of Biotechnology, Science Press, Beijing, 2003 Jing-Ying Tan, English-Chinese Biological Dictionary of Biochemistry and Molecular Biology, 2nd Edition, Science Press, Beijing, 2007

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R18 R19 R20 R21 R22

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Scientific Terms Laboratory of Science Press, English-Chinese Biological Dictionary, 2nd Edition, Science Press, Beijing, 1997 Scientific Terms Laboratory of Science Press, Chinese-English Biological Dictionary, 2nd Edition, Science Press, Beijing, 1998 Yu Hui, A New Century Chinese-English Dictionary, Foreign Language Teaching and Research Press, Beijing, 2003 Zong-Guo Huang and Mei-Ling Jin, Dictionary of Marine Biology, Ocean Press, Beijing, 1994 (in Chinese) Wenbao Chang, et al., Dictionary of Chemistry, Science Press, Beijing, 2008 (in Chinese)

(Book References 11) R23

R24

R25 R26 R27 R28 R29 R30 R31 R32

R33

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) 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 Janet S. Dodd, The ACS Style Guide, A Manual for Authors and Editors, 2nd Edition, American Chemical Society, Washington, DC, 1997 Shu-Xian Ren, Invertebrates, 2 volumes, Peking University Press, Beijing, 1990 (in Chinese) R. Mcneill Alexander, (translated by Lan-zhi Du), The invertebrates, Chemical Industry Press, Beijing, 2013 (in Chinese) Yanghua Yi and Binghua Jiao, Modern Marine pharmacology, Science Press, Beijing, 2006 (in Chinese) Chang-Yun Wang and Chang-Lun Shao, Marine pharmacology, Science Press, Beijing, 2011 (in Chinese) Rensheng Xu, et al., Chemistry of Natural Products, 2nd Edition, Science Press, Beijing, 2004 (in Chinese) Yue-Zeng Chen, General Biology, Higher Education Press, Beijing, 1997 (in Chinese) 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 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 exchange 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 O-heterocycles (1–259) and aromatic compounds (260–951) are isolated from ascidian of genus Synoicum? From index 3 of volume 7, one will get the following related data in detail: Synoicum blochmanni 591, 592, 593, 595, 599, 600, 601, 602. https://doi.org/10.1515/9783110655810-204

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Synoicum globosum 595, 596. Synoicum prunum 248, 249, 250, 591. Synoicum sp. 585, 586, 587, 588, 603. The answer of the current question must be that 3 O-heterocycle compounds (248, 249, and 250) and 14 aromatic compounds (585–588, 591–593, 595, 596, 599, and 600–603) are isolated from ascidian of genus Synoicum. Then, readers can enjoy to studying these 17 compounds by reading the book, including their pharm-activity (question of types 3 and 5). For example, with entry 248, a reader will know that the compound 248 Prunolide A had already been isolated from ascidian Synoicum prunum (Australia) and it has cytotoxic activity (inhibits growth of HeLa at 25μmol/L, weak). OH Br

OH

Br Br

Br

O O

O O

O Br

Br HO

Br Br

OH

(2) An Illustration of Type 4 (and Type 2, Type 6) Question “What are isolated aromatic compounds (260–951) with antioxidant activity? And what are their marine sources?” To browse Index 5 of volume 7, searching “Antioxidant” and “Antioxidant inactive,” the following results were obtained (The “Antioxidant inactive ” means that antioxidant pharmacological assay has been done, but the result is not active or activity being very low): Antioxidant 278, 280, 401, 559, 767, 768, 782, 889, 921, 941, 942. Antioxidant, DPPH radical scavenger 267, 282, 284, 289, 290, 292, 293, 294, 295, 296, 297, 301, 303, 305, 306, 343, 361, 362, 381, 382, 383, 384, 460, 462, 546, 550, 639, 691, 698, 699, 701, 770, 771, 807, 812, 814, 819, 864, 865, 913. Antioxidant, free radical scavenger 325. Antioxidant, free radicals scavenger, DPPH radical 288, 292. Antioxidant, free radicals scavenger, NO• radical 288, 292. Antioxidant, free radicals scavenger, O2•− radical 292. Antioxidant, free radicals scavenger, ONOO− radical 288, 292. Antioxidant, hydroxyl radical scavenger 657. Antioxidant, increased antioxidative glutathione peroxidase, catalase, and superoxide dismutase activities 553.

How to Use the HAMNP Books

XXI

Antioxidant, O2•− radical scavenger 288. Antioxidant, radical scavenger 333, 334. Antioxidant, reduction of ROS overproduction 547, 553. Antioxidant, significant 656. Antioxidant, thiobarbituric acid reactive substance TBARS assay 271, 272. Antioxydant, DPPH scavenger 529. Antioxidant inactive, DPPH radical scavenger 388, 433, 434, 435, 436. Antioxidant inactive, superoxide anion radical scavenger 388, 433, 434, 435, 436. Further, from the entry bodies of the 62 active aliphatic compounds (267, 271, 272, 278, 280, 282, 284, 288–290, 292–297, 301, 303, 305, 306, 325, 333, 334, 343, 361, 362, 381–384, 401, 460, 462, 529, 546, 547, 550, 553, 559, 639, 656, 657, 691, 698, 699, 701, 767, 768, 770, 771, 782, 807, 812, 814, 819, 864, 865, 889, 913, 921, 941, and 942), 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



 Citrinin H

m-Benzenediol derivatives

Marine-derived fungus Penicillium sp. MFA from green alga Ulva pertusa (Korea waters)



 Acremonin A

p-Benzenediol derivatives

Marine-derived fungus Acremonium sp.



 Acremonin A -βglucopyranoside

p-Benzenediol derivatives

Marine-derived fungus Acremonium sp.

. . .. . . . . .. . . . . .. . .

. . .. . .

. . .. . .



 δ-Indomycinone

Pyrano[b] anthraquinones

Marine-derived streptomycete Streptomyces sp. B (Lagoon, Gulf of Mexico), marine-derived streptomycete Streptomyces sp. (psychrophilic, cold water, depth of  m sediment core, culture broth)



 ,-Dihydroxy-Miscellaneous (hydroxymethyl)-H-anthra polycyclic [,-bc]thiophen--one aromatics

Bryozoan Dakaria subovoidea (Japan waters)



 ,-Dihydroxy--oxo-Hanthra[,-bc]thiophene-carboxylic acid, methyl ester

Bryozoan Dakaria subovoidea (Japan waters)

Miscellaneous polycyclic aromatics

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How to Use the HAMNP Books

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

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

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

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XXIV

List of Abbreviations and Acronyms

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

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

XXV

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

XXVI

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

List of Abbreviations and Acronyms

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

List of Abbreviations and Acronyms

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

XXVII

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

XXVIII

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

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

List of Abbreviations and Acronyms

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

List of Abbreviations and Acronyms

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

XXIX

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

XXX

List of Abbreviations and Acronyms

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

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

Polio virus pregnane X receptor NAD(P)H: quinone reductase difference in log10 GI50 (mol/L) value of the most sensitive cell line and the least sensitive cell white rat rabbit rat lens aldose reductase ribonucleic acid reactive oxygen species (involved in genesis of various cancers, arteriosclerosis, rheumatism, and aging) code of a yeast respiratory syncytial virus reverse transcriptase response unit of binding capacity to HIV-1 targets, 1 RU = 1 pg/mm2 RyR1-FKBP12 Ca2+ channel, a tetrameric heterodimeric channel protein (~2000 kDa) associated with smaller 12 kDa immunophilin FKBP12 ribosomal protein a protein kinase severe acute respiratory syndrome scavenging rate macrophage-tropic viral strain IC50 of testing cells/IC50 of HUVECs selective index = cytotoxic CC50/target EC50 selective index = cytotoxic IC50/target IC50 selective index = cytotoxic IC50/target MIC selective index = cytotoxic TC50/target IC50 hmn sirtuin type 2 (a NAD+-dependent cytoplasmic protein that is 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

XXXI

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

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

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

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XXXIV

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

List of Cancer Cell Codes

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

List of Cancer Cell Codes

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

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

XXXV

XXXVI

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

List of Cancer Cell Codes

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

List of Cancer Cell Codes

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

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

XXXVII

XXXVIII

List of Cancer Cell Codes

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

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

List of Cancer Cell Codes

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

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

XXXIX

XL

List of Cancer Cell Codes

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

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

XLI

XLII

WMF XF498 XRS-6 XVS ZR-75-1

List of Cancer Cell Codes

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

1 Oxygen Heterocycles 1.1 β-Lactones 1 Salinosporamide A Antibiotic NPI 0052 Type: β-Lactones. C15H20ClNO4 Needles (EtOAc/2,3,3trimethylpentane), mp 169–171 °C, [α]D25 = −72.9° (c = 0.55, MeOH). Source: Marinederived actinomycete Salinispora tropica CNB-392. Pharm: Cytotoxic (NCI-H226, IC50 < 0.011 μmol/L; NCI-H522, IC50 = 0.043 μmol/L; HCC2998, IC50 = 0.018 μmol/L; CNS cancer SNB75, IC50 < 0.011 μmol/L; SK-MEL-28, IC50 < 0.011 μmol/L; melanoma SNB75, IC50 = 0.032 μmol/L; A498, IC50 = 0.011 μmol/L; RXF-393, IC50 = 0.023 μmol/L; MDA-MB-435, IC50 < 0.011 μmol/L; CCRF-CEM, IC50 > 100 μmol/L; DU145, IC50 > 100 μmol/L); cytotoxic (NCI’s 60-cell-line assay mean GI50 < 0.011 μmol/L; HCT116, GI50 = 0.035 μmol/L, LOX-IMVI, GI50 < 0.011 μmol/L; HOP-92, GI50 < 0.011 μmol/L; OVCAR-3, GI50 < 0.011 μmol/L; PC3, GI50 < 0.011 μmol/L); proteasome inhibitor. Ref: P. G. Williams, et al, JOC, 2005, 70, 6196

H O

H N

5

OH O

2

O Cl

2 Salinosporamide B Antibiotic NPI 0047 Type: β-Lactones. C15H21NO4 Cryst. (EtOAc), mp 143–145 °C, [α]D25 = −54.5° (c = 0.29, MeOH). Source: Marine-derived actinomycete Salinispora tropica CNB-392. Pharm: Cytotoxic (HCT116, GI50 = 20 μmol/L). Ref: P. G. Williams, et al, JOC, 2005, 70, 6196

H O

H N OH O O

3 Salinosporamide K Type: β-Lactones. C13H17NO4 Source: Marine-derived actinomycete Salinispora pacifica (Fiji). Pharm: 20S-Proteasome inhibitor (Chymotrypsin-like). Ref: A. S. Eust´aquio, et al, Chem. Bio. Chem., 2011, 12, 61

https://doi.org/10.1515/9783110655810-001

2

1 Oxygen Heterocycles

O

H N

H OH O

O

1.2 Furans 4 Acetylsumiki’s acid Type: Furans. C8H8O5 Source: Marine-derived fungus Cladosporium herbarum from sponge Callyspongia aerizusa, Epicoccum sp. Pharm: Antibacterial (Bacillus subtilis and Staphylococcus aureus, 5 μg/disc). Ref: R. Jadulco, et al, JNP, 2001, 64, 527

OH

O O O

O

5 4,5-Dihydro-2,4-dimethyl-3-furancarboxaldehyde Type: Furans. C7H10O2 Oil, [α]D20 = +38.9° (c = 0.61, CHCl3). Source: Marine-derived fungus Ulocladium botrytisfrom from sponge Callyspongia vaginalis. Pharm: Antifungal. Ref: U. Höller, et al, EurJOC, 1999, 2949 O H

O

6 2,3-Dihydro-2-hydroxy-2,4-dimethyl-5-trans-propenylfuran-3-one Type: Furans. C9H12O3 Prisms (petrol), mp 99 °C, [α]D20 = +1.8° (c = 0.29, EtOH). Source: Marine-derived fungus Ascochyta salicorniae from green alga Ulva sp. (North Sea coast, Germany), Stemphylium radicinum and Ascochyta salicorniae. Pharm: Tyrosine kinase inhibitor (TKp56lck, 40 μg/mL, InRt = 44%, 200 μg/mL, InRt = 91%); antiplasmodial (Plasmodium falciparum K1, IC50 = 1.763 μg/mL; Plasmodium falciparum NF 54, IC50 = 1.760 μg/mL); antifungal (50 μg/disk, Microbotryum violacea, IZD = 1 mm; Eurotium repens, IZD = 2 mm). Ref: C. Osterhage, et al, JOC, 2000, 65, 6412

1.2 Furans

3

O

O

OH

7 Echinofuran‡ 8,12-Epoxy-1 (10),4 (15),7,11-guaiatetraene Type: Furans. C15H18O Oil, [α]D20 = −91° (c = 0.138, CHCl3). Source: Gorgonian Echinogorgia praelonga (Okinawa). Pharm: Cell division inhibitor (fertilized sea urchin egg assay). Ref: J. Tanaka, et al, JNP, 1992, 55, 1522

O H

8 (2S,3S,5R)-5-[(1R)-1-Hydroxydec-9-enyl]-2-pentyltetrahydrofuran-3-ol Type: Furans. C19H36O3 Plates (hexane), mp 54.5–55.0 °C, [α]D21 = +15.0° (c = 1, CHCl3). Source: Brown alga Notheia anomala. Pharm: Nematocide (potent and selective inhibitor of larval development of parasitic nematodes). Ref: R. G. Warren, et al, Aust. J. Chem., 1980, 33, 891│S. Hatakeyamu, et al, Tet. Lett., 1985, 26, 1333│R. A. Barrow, et al, Aust. J. Chem., 1990, 43, 895│L. M. Murray, et al, Aust. J. Chem., 1991, 44, 843│H. Chikashita, et al, Chem. Lett., 1993, 477│Z.M. Wang, et al, JOC, 1998, 63, 1414│Y. Mori, et al, Tet. Lett., 1999, 40, 731│C. G. García, et al, Tet. Lett., 2000, 41, 4127 HO H O OH

9 (2S,3S,5S)-5-[(1S)-1-Hydroxydec-9-enyl]-2-pentyltetrahydrofuran-3-ol Type: Furans. C19H36O3 Source: Brown alga Notheia anomala (Southern Australia). Pharm: Nematocide (potent and selective inhibitor of larval development of parasitic nematodes). Ref: R. G. Warren,et al, Aust. J. Chem., 1980, 33, 891│R. A. Barrow, et al, Aust. J. Chem., 1990, 43, 895│L. M. Murray, et al, Aust. J. Chem., 1991, 44, 843│R. J. Capon, et al, Tetrahedron, 1998, 54, 2227│C. G. García, et al, Tet. Lett., 2000, 41, 4127

4

1 Oxygen Heterocycles

HO H O OH

10 Laurencione (cyclic hemiacetal form) Dihydro-3 (2H)-furanone Type: Furans. C5H8O3 Light green oil. Source: Red alga Laurencia spectabilis (Oregon). Pharm: Toxic (brine shrimp). Ref: M. W. Bernart, et al, Phytochemistry, 1992, 31, 1273│N. De Kimpe, et al, JOC, 1995, 60, 5162│N. De Kimpe, et al, Synthesis, 1996, 1131 O

O

OH

11 Mutafuran H Type: Furans. C16H26Br2O4 Source: Sponge Xestospongia testudinaria (Sanya, Hainan, China). Pharm: AChE inhibitor (potent). Ref: X. Zhou, et al, Chem. Phys. Lipids, 2011, 164, 703

Br

O O

Br

12 Plakorfuran A Type: Furans. C19H30O4 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Antifungal (weak). Ref: X. -F. Liu, et al, Tetrahedron, 2012, 68, 4635

OH

O O

O

13 Plakorsin B Type: Furans. C22H38O3 Amorph. solid. Source: Sponge Plakortis simplex (Taiwan waters). Pharm: Cytotoxic (KB16, IC50 = 3.43 μg/mL; Colon250, IC50 = 0.28 μg/mL). Ref: Y. C. Shen, et al, JNP, 2001, 64, 324

1.2 Furans

5

O HO

O

10

14 Sargafuran Type: Furans. C27H36O4 Oil, [α]D = −1.3° (c = 0.9, CHCl3). Source: Brown alga Sargassum macrocarpum (Japan waters). Pharm: Antibacterial; anti-acne (prevent or improve propionibacterium acne). Ref: Y. Kamei, et al, J. Antibiot., 2009, 62, 259

HO

O

O

OH

15 Testufuran A Type: Furans. C18H25BrO3 Yellow oil, [α]D23 = −18° (c = 0.04, MeOH). Source: Sponge Xestospongia testudinaria. Pharm: Stimulator of adipogenesis (preadipocyte differentiation-inducing activity (30 μmol/L, 2+, 130 μmol/L, 3+)). Ref: T. Akiyama, et al, Tetrahedron, 2013, 69, 6560 Br H

H O

HO O

16 (all-Z)-5-(2,5,8,11-Tetradecatetraenyl)-2-furanacetic acid Type: Furans. C20H26O3 Yellow oil. Source: Sponges Dictyonella incisa (Mediterranean Sea) and Hymeniacidon hauraki (New Zealand). Pharm: Cytotoxic (P388, IC50 = 13.4 μg/mL). Ref: P. Ciminiello, et al, Experientia, 1991, 47, 739│M. R. Prinsep, et al, JNP, 1994, 57, 1557 O O

OH

17 Varitriol Type: Furans. C15H20O5 Oil, [α]D25 = +18.5° (c = 2.3, MeOH). Source: Marine-derived fungus Emericella variecolor M75-2. Pharm: Cytotoxic (In NCI’s 60-cell panel, for selected renal, CNS and breast cancer cell lines, varitriol displayed increased potency). Ref: J. Malmstrøm, et al, JNP, 2002, 65, 364│M. Saleem, et al, NPR, 2007, 24, 1142 (rev)

6

1 Oxygen Heterocycles

O

OH

O

HO

OH

1.3 Butanolides 18 Acetoxyfimbrolide A Type: Butanolides. C11H12Br2O4 [α]D25 = −4.1° (c = 1.3, CHCl3). Source: Red alga Delisea fimbriata. Pharm: Antibiotic; antifungal. Ref: R. Kazlauskas, et al, Tet. Lett., 1977, 37│J. A. Pettus, et al, Tet. Lett., 1977, 41 O O Br

O

Br

O H

19 Acetoxyfimbrolide B Type: Butanolides. C11H12Br2O4 [α]D25 = +29° (c = 5.8, CHCl3). Source: Red alga Delisea fimbriata. Pharm: Antibiotic; antifungal. Ref: R. Kazlauskas, et al, Tet. Lett., 1977, 37│J. A. Pettus, et al, Tet. Lett., 1977, 41 O O Br

O

O

H Br

20 Acetoxyfimbrolide D Type: Butanolides. C11H12BrIO4 [α]D25 = +26° (c = 1.4, CHCl3). Source: Red alga Delisea fimbriata. Pharm: Antibiotic; antifungal. Ref: R. Kazlauskas, et al, Tet. Lett., 1977, 37│J. A. Pettus, et al, Tet. Lett., 1977, 41

1.3 Butanolides

7

O O Br

O

I

O H

21 Antibiotic MKN 003C Type: Butanolides. C13H22O3 [α]D25 = +20.3° (c = 0.16, CH3OH). Source: Marinederived streptomycete Streptomyces sp. M02750 (Korea watersn waters). Pharm: Antifoulant. Ref: K. W. Cho, et al, JNP, 2001, 64, 664 OH

O O

22 Asperlactone Type: Butanolides. C9H12O4 Yellow oil. Source: Marine-derived fungus Exophiala sp. Pharm: Antifungal; antibacterial. Ref: M. J. Garson, et al, JCS Perkin I, 1984, 1021 O H H

HO

H

O

O

23 Aspernolide A Type: Butanolides. C24H24O7 Gummy solid, [α]D28 = +88.7° (c = 0.58, CHCl3). Source: Marine-derived fungus Aspergillus terreus PT06-2 (grown in high salt medium 10% salinity), marine-derived fungus Aspergillus terreus SCSGAF0162. Pharm: Cytotoxic (several cancer cell lines, mild); antiviral (HSV virus, IC50 = 68.16 μmol/L). Ref: R. R. Parvatkar, et al, Phytochemistry, 2009, 70, 128│Y. Wang, et al, Mar. Drugs, 2011, 9, 1368│X. -H. Nong, et al, Mar. Drugs, 2014, 12, 6113 O

O

O

O O

HO

OH

8

1 Oxygen Heterocycles

24 Aspernolide B Terrelactone Type: Butanolides. C24H26O8 Light brown syrup, [α]D28 = +48.3° (c = 0.29, MeOH); pale yellow oil, [α]D25 = +71° (c = 0.5, CHCl3). Source: Marinederived fungi Aspergillus terreus from soft coral Sinularia kavarattiensis (India waters) and Aspergillus terreus PT06-2 (Grown in high salt medium 10% salinity). Pharm: Antibacterial (Enterobacter aerogenes, Staphylococcus aureus and Pseudomonas aeruginosa, all MICs > 100 μmol/L); antifungal (Candida albicans, MIC > 100 μmol/L, control Ketoconazole, MIC = 5 μmol/L). Ref: R. R. Parvatkar, et al, Phytochemistry, 2009, 70, 128│Y. Wang, et al, Mar. Drugs, 2011, 9, 1368 OH O O

O

O OH

HO

OH

25 Aspiketolactonol Type: Butanolides. C9H12O4 Colorless oil (MeOH), [α]D25 = +10.5° (c = 0.12, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, 100 μg/mL: HL60, InRt = 11.7%, control Docetaxol, InRt = 49.9%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116

S

H

O

R

HO

H

O O

26 Aspilactonol A Type: Butanolides. C9H14O3 Colorless oil (MeOH), [α]D25 = +24.6° (c = 0.23, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, 100 μg/mL: HL60, InRt = 17.7%, control Docetaxol, InRt = 49.9%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116 OH S

H

S

O O

1.3 Butanolides

9

27 Aspilactonol B Type: Butanolides. C9H14O5 Colorless oil (MeOH), [α]D25 = +34.5° (c = 0.41, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, 100 μg/mL: HL60, InRt = 22.2%, control Docetaxol, InRt = 49.9%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116 OH H HO

S R

H

OH

8S

O

9R

O

28 Aspilactonol C Type: Butanolides. C9H14O5 Colorless oil (MeOH), [α]D25 = +27.2° (c = 0.32, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, 100 μg/mL: HL60, InRt = 16.7%, control Docetaxol, InRt = 49.9%; K562, InRt = 20.0%, Docetaxol, InRt = 55.6%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116 OH H HO

S R

H

OH

8R

O

9S

O

29 Aspilactonol D Type: Butanolides. C10H16O5 Colorless oil (MeOH), [α]D25 = −1.7° (c = 0.38, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, 100 μg/mL: HL60, InRt = 20.0%, control Docetaxol, InRt = 49.9%; BGC823, InRt = 13.2%, Docetaxol, InRt = 61.5%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116 O H HO

S R

H

8S

O

OH 9R

O

30 Aspilactonol E Type: Butanolides. C9H14O4 Mixture with Aspilactonol F, Colorless oil (MeOH), [α]D25 = +78.1° (c = 1.00, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1

10

1 Oxygen Heterocycles

from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Mixture with Aspilactonol F, Cytotoxic (MTT method, 100 μg/mL: HeLa, InRt = 13.4%, control Docetaxol, InRt = 45.1%; K562, InRt = 14.1%, Docetaxol, InRt = 55.6%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116

H HO

S

OH

R

H

O

9R*

O

31 Aspilactonol F Type: Butanolides. C9H14O4 Mixture with Aspilactonol E, Colorless oil (MeOH), [α]D25 = +78.1° (c = 1.00, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Mixture with Aspilactonol E, Cytotoxic (MTT method, 100 μg/mL: HeLa, InRt = 13.4%, control Docetaxol, InRt = 45.1%; K562, InRt = 14.1%, Docetaxol, InRt = 55.6%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116

H HO

S

OH

R

H

9S*

O O

32 4-Bromobeckerelide Type: Butanolides. C9H13BrO4 Source: Red alga Beckerella subcostatum. Pharm: Antimicrobial. Ref: K. Ohta, Agrc. Biol. Chem., 1977, 41, 2105 OH Br

O

O

OH

33 (+)-Butyrolactone I Type: Butanolides. C24H24O7 Cryst. (CH2Cl2), mp 95 °C (dec), [α]D17 = +86° (c = 0.5, EtOH). Source: Marine-derived fungus Aspergillus terreus PT06-2 (grown in high salt medium 10% salinity), terrestrial and marine-derived Aspergillus terreus (strains IFO 8835, DRCC 152 and HKI0499). Pharm: Antiviral (influenza virus H1N1, lower cytotoxicity, IC50 = 143.1 μmol/L, CC50 = 976.4 μmol/L, control Ribavirin, IC50 = 100.8 μmol/L); cytotoxic (HL60, IC50 = 57.5 μmol/L, control VP-16 (Etoposide), IC50 = 0.042 μmol/L); kinase inhibitor (high selectivity towards CDK1 and CDK2). Ref: M. Kitagawa, et al, Oncogene, 1994, 9, 2549│K. V. Rao, et al, CPB, 2000, 48, 559│Y. Wang, et al, Mar. Drugs, 2011, 9, 1368

1.3 Butanolides

11

OH

O

O

O O

HO

OH

34 (+)-Butyrolactone II Type: Butanolides. C19H16O7 Plates (CH2Cl2), mp 94–96 °C, [α]D25 = +85° (c = 1.0, EtOH). Source: Marine-derived fungus Aspergillus terreus PT06-2 (grown in high salt medium 10% salinity). Pharm: Cytotoxic. Ref: Y. Wang, et al, Mar. Drugs, 2011, 9, 1368 OH

O

O

O O

HO

OH

35 (+)-Butyrolactone III Type: Butanolides. C24H24O8 Yellowish mass (CH2Cl2), mp 70 °C, [α]D25 = +80° (c = 0.7, EtOH). Source: Marine-derived fungus Aspergillus terreus PT06-2 (grown in high salt medium 10% salinity). Pharm: Cytotoxic. Ref: Y. Wang, et al, Mar. Drugs, 2011, 9, 1368 OH O O

O

O O

HO

OH

36 9-Chloro-8-hydroxy-8,9-deoxyasperlactone Type: Butanolides. C9H13ClO4 [α]D26 = +76° (c = 0.01, CHCl3). Source: Marine-derived fungus Aspergillus ostianus TUF 01F313 from an unidentified sponge (Pohnpei I., Federated States of Micronesia). Pharm: Antibacterial (25 μg/disk, inhibits growth of Ruegeria atlantica, IZD = 10.1 mm). Ref: M. Namikoshi, et al, J. Antibiot., 2003, 56, 755│M. Saleem, et al, NPR, 2007, 24, 1142 (rev)

12

1 Oxygen Heterocycles

HO

Cl

HO H

O

O

37 8-Chloro-9-hydroxy-8,9-deoxyasperlactone Type: Butanolides. C9H13ClO4 [α]D24 = +22.5° (c = 0.17, CHCl3). Source: Marinederived fungus Aspergillus ostianus TUF 01F313 from an unidentified sponge (Pohnpei I., Federated States of Micronesia). Pharm: Antibacterial (5 μg/disk, inhibits growth of Ruegeria atlantica, IZD = 12.7 mm). Ref: M. Namikoshi, et al, J. Antibiot., 2003, 56, 755│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) Cl

OH

HO H

O

O

38 Cillifuranone Type: Butanolides. C10H12O4 Pale yellow needles. Source: Marine-derived fungus Penicillium chrysogenum from sponge Tethya aurantium (Limski Channel, Adriatic Sea, Croatia). Pharm: Antifungal (Septoria tritici, 100 μmol/L, 20% growth inhibition); antibacterial (Xanthomonas campestris, 100 μmol/L, 24% growth inhibition). Ref: J. Wiese, et al, Mar. Drugs, 2011, 9, 561 O

O

HO O

39 Eutypoid B Type: Butanolides. C17H14O4 Source: Marine-derived fungus Penicillium sp. (sea water sample, North Sea). Pharm: Glycogen synthase kinase-3β inhibitor. Ref: D. Schulz, et al, JNP, 2011, 74, 99 O

O OH

HO

1.3 Butanolides

13

40 Eutypoid C Type: Butanolides. C17H14O5 Source: Marine-derived fungus Penicillium sp. (sea water sample, North Sea). Pharm: Glycogen synthase kinase-3β inhibitor. Ref: D. Schulz, et al, JNP, 2011, 74, 99 O

O

OH OH HO

41 Eutypoid D Type: Butanolides. C17H14O5 Source: Marine-derived fungus Penicillium sp. (water sample, North Sea). Pharm: Glycogen synthase kinase-3β inhibitor. Ref: D. Schulz, et al, JNP, 2011, 74, 99 O

O OH

HO

OH

42 Eutypoid E Type: Butanolides. C17H14O6 Source: Marine-derived fungus Penicillium sp. (water sample, North Sea). Pharm: Glycogen synthase kinase-3β inhibitor. Ref: D. Schulz, et al, JNP, 2011, 74, 99 O

O

OH HO OH OH

43 Flavalactone 1 Type: Butanolides. C21H38O3 Needles (MeOH), mp 67 °C. Source: Gorgonian Euplexaura flava. Pharm: Anti-inflammatory. Ref: H. Kikuchi, et al, Chem. Lett., 1982, 233; H. Kikuchi, et al, CPB, 1983, 31, 1172 HO

O

O

14

1 Oxygen Heterocycles

44 Flavalactone 2 Type: Butanolides. C25H42O3 Oil. Source: Gorgonian Euplexaura flava. Pharm: Antiinflammatory. Ref: H. Kikuchi, et al, Chem. Lett., 1982, 233; H. Kikuchi, et al, CPB, 1983, 31, 1172 HO

O

O

45 Flavalactone 3 Type: Butanolides. C27H44O3 Oil. Source: Gorgonian Euplexaura flava. Pharm: Antiinflammatory. Ref: H. Kikuchi, et al, Chem. Lett., 1982, 233; H. Kikuchi, et al, CPB, 1983, 31, 1172 HO

O

O

46 Flavipesin A Type: Butanolides. C22H22O5 Source: mangrove-derived fungus Aspergillus flavipes AIL8 (endophytic) from mangrove Acanthus ilicifolius. Pharm: Antibacterial (Staphylococcus aureus, MIC = 8.0 μg/mL, Bacillus subtilis, MIC = 0.25 μg/mL). Ref: Z. Q. Bai, et al, Fitoterapia, 2014, 95, 194

O O O O OH

47 Harzialactone A Type: Butanolides. C11H12O3 Colorless oil, mp 82–84 °C, [α]D32 = +33.3° (c = 0.3, CHCl3). Source: Marine-derived fungus Trichoderma harzianum OUPS-N115 from sponge Halichondria okadai. Pharm: Cytotoxic (cultured P388, ED50 > 100 μg/mL). Ref: T. Amagata, et al, J. Antibiot., 1998, 51, 33 OH

O

O

1.3 Butanolides

15

48 Honaucin A Type: Butanolides. C8H9NO4 Source: Cyanobacterium Leptolyngbya crossbyana (Hōnaunau reef, Hawaii). Pharm: Inhibits NO production and expression of several pro-infiammatory cytokines (RAW264.7 cells); inhibits bioluminescence (Vibrio harveyi). Ref: H. Choi, et al, Chem. Biol., 2012, 19,589 O O O

Cl

O

49 (S)-2-(2′-Hydroxyethyl)-4-methyl-γ-butyrolactone Type: Butanolides. C7H10O3 Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, 100 μg/mL: HL60, InRt = 14.2%, control Docetaxol, InRt = 49.9%; HeLa, InRt = 15.7%, Docetaxol, InRt = 45.1%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116 S

OH H

O O

50 Isoaspulvinone E Type: Butanolides. C17H12O5 Source: Mangrove-derived fungus Aspergillus terreus GWQ-48. Pharm: Antiviral (influenza a viral H1N1, IC50 = 101.23 μmol/L). Ref: H. Gao, et al, Bioorg. Med. Chem. Lett. 2013, 23, 1776 O

E

O

OH OH HO

51 Isobutyrolactone II Type: Butanolides. C18H16O6 Source: Marine-derived fungus Aspergillus terreus SCSGAF0162. Pharm: Antiviral (HSV virus, IC50 = 62.08 μmol/L). Ref: X. -H. Nong, et al, Mar. Drugs, 2014, 12, 6113 O HO

OH O O

HO

16

1 Oxygen Heterocycles

52 Isocladospolide B NG 261 Type: Butanolides. C12H20O4 Amorph. solid, [α]D = −90° (c = 0.23, MeOH). Source: An unidentified marine-derived fungus I96S215 from both unidentified sponge and fungus Cladosporium cladosporioides sp. TF-0380. Pharm: Nerve growth factor agonist. Ref: C. J. Smith, et al, JNP, 2000, 63, 142│S. Gesner, et al, JNP, 2005, 68, 135 H O

O

OH

OH

53 Lissoclinolide Tetrenolin Type: Butanolides. C11H12O4 Yellow cryst. (CHCl3), mp 126–128 °C. Source: Ascidian Lissoclinum patella. Pharm: Antibacterial (gram-negative bacterium Escherichia coli). Ref: B. S. Davidson, et al, JNP, 1990, 53, 1036│R. Rossi, et al, Tet. Lett., 1998, 39, 7799│C. Xu, et al, Tet. Lett., 1999, 40, 431 OH

HO O O

54 Nodulisporacid A Type: Butanolides. C16H20O6 Equilib. mixt. of E- and Z-isomers (1:1), amorph. yellow solid, [α]D27 = −20.6° (c = 1.1, MeOH). Source: Marine-derived fungus Nodulisporium sp. CRIF 1. Pharm: Antiplasmodial (Plasmodium falciparum 94 strain, IC50 = 1–10 μmol/L). Ref: C. Kasettrathat, et al, Phytochemistry, 2008, 69, 2621│T. Sumiya, et al, Tet. Lett., 2010, 51, 2765

O O O

E

HO O

O

55 Nodulisporacid A benzyl ester Type: Butanolides. C22H24O6 Source: Marine-derived fungus Nodulisporium sp. CRIF 1. Pharm: Cytotoxic (HuCCA-1, IC50 = 2.10 μg/mL; KB, IC50 = 3.20 μg/mL; HeLa, IC50 = 2.60 μg/mL; MDA-MB-231, IC50 = 0.38 μg/mL; T47D, IC50 = 0.14 μg/mL; HepG2, IC50 = 2.00 μg/mL; A549, IC50 = 2.20 μg/mL; HCC-S102, IC50 = 4.80 μg/mL; HL60, IC50 = 1.18 μg/mL; P388, IC50 = 0.70 μg/mL; control Etoposide: HuCCA-1,

1.3 Butanolides

17

IC50 = 5.30 μg/mL; KB, IC50 = 0.46 μg/mL; HeLa, IC50 = 0.40 μg/mL; MDA-MB-231, IC50 = 0.40 μg/mL; T47D, IC50 = 0.04 μg/mL; HL60, IC50 = 0.77 μg/mL; P388, IC50 = 0.10 μg/mL; control Doxorubicind: HepG2, IC50 = 0.19 μg/mL; A549, IC50 = 0.48 μg/mL; HCC-S102, IC50 = 1.20 μg/mL). Ref: C. Kasettrathat, et al, Phytochemistry, 2008, 69, 2621

O O

O E

O

O

O

56 Nodulisporacid A methyl ester Type: Butanolides. C17H22O6 Source: Marine-derived fungus Nodulisporium sp. CRIF 1. Pharm: Cytotoxic (HuCCA-1, IC50 = 2.30 μg/mL; KB, IC50 = 2.20 μg/mL; HeLa, IC50 = 2.70 μg/mL; MDA-MB-231, IC50 = 2.50 μg/mL; T47D, IC50 = 1.70 μg/mL; HepG2, IC50 = 2.30 μg/mL; A549, IC50 = 7.50 μg/mL; HCC-S102, IC50 = 6.00 μg/mL; HL60, IC50 = 1.01 μg/mL; P388, IC50 = 0.77 μg/mL; control Etoposide: HuCCA-1, IC50 = 5.30 μg/mL; KB, IC50 = 0.46 μg/mL; HeLa, IC50 = 0.40 μg/mL; MDA-MB-231, IC50 = 0.40 μg/mL; T47D, IC50 = 0.04 μg/mL; HL60, IC50 = 0.77 μg/mL; P388, IC50 = 0.10 μg/mL; control Doxorubicind: HepG2, IC50 = 0.19 μg/mL; A549, IC50 = 0.48 μg/mL; HCC-S102, IC50 = 1.20 μg/mL). Ref: C. Kasettrathat, et al, Phytochemistry, 2008, 69, 2621

O O

O E

O O

O

57 Penicilactone Type: Butanolides. C7H10O4 Gum, [α]D25 = +23° (c = 0.12, MeOH). Source: Marinederived fungus Penicillium sp. PSU-F44 from gorgonian sea fan Annella sp. (Thailand). Pharm: Antibacterial (MRSA SK1). Ref: K. Trisuwan, et al, CPB, 2009, 57, 1100 O

O

OH O

18

1 Oxygen Heterocycles

58 Pestalolide Type: Butanolides. C12H20O2 Colorless gum. Source: Mangrove-derived fungus Pestalotiopsis sp. from mangrove Rhizophora apiculata (branch, Satun, Thailand). Pharm: Antifungal (Candida albicans NCPF3153 and Cryptococcus neoformans ATCC 90112, MIC = 128 μg/mL). Ref: S. Klaiklay, et al, Tetrahedron, 2012, 68, 2299 O O

59 Plakilactone C Type: Butanolides. C16H24O3 Source: Sponge Plakinastrella mamillaris (Fiji). Pharm: Antidiabetic and anti-arthrosclerosis (due to itscovalent binding to peroxisome proliferator-activated receptor γ (PPARγ), inhibiting adipocyte gene transcription). Ref: C. Festa, et al, JMC, 2012, 55, 8303 O

O

O

60 Plakorsin D Type: Butanolides. C15H24O3 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 > 100 μmol/L; K562, IC50 > 100 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). Ref: J. Zhang, et al, JNP, 2013, 76, 600

O

O OH

61 Plakortone G Type: Butanolides. C18H30O2 Oil, [α]D = −25.9° (c = 0.008, CHCl3). Source: Sponge Plakortis sp. (subclass Homoscleromorpha, order Homosclerophorida, famiily Plakinidae, Jamaica). Pharm: Antiplasmodial (Plasmodium falciparum D6 clone, in vitro, IC50 = 4200 ng/mL, control Artemlsinin, IC50 = 12 ng/mL; CRPF W2 clone, in vitro, IC50 > 4760 ng/mL, control Artemlsinin, IC50 = 7 ng/mL); cytotoxic (HT29, IC50 > 1 μg/mL, control Tamoxifen, IC50 = 1.86 μg/mL; A549, IC50 > 1 μg/mL, control

1.3 Butanolides

19

Tamoxifen, IC50 = 1.86 μg/mL; MEL28, IC50 > 10 μg/mL, control Tamoxifen, IC50 = 1.86 μg/mL; hmn primary tumor cells, IC50 = 4.7 μg/mL, control Doxorubicin, IC50 = 25 nmol/L); anti-hepatitis-B (EC50 > 100 μg/mL, control 3TC, EC50 = 0.062– 0.065 μg/mL); antituberculosis (Mycobacterium tuberculosis, InRt = 4% at 6.25 μg/mL, control Rifampin, MIC = 0.25 μg/mL). Ref: D. J. Gochfeld, et al, JNP, 2001, 64, 1477│ S. Kowashi, et al, Tet. Lett., 2004, 45, 4393

O

O

62 Plakortoxide A Type: Butanolides. C17H28O3 Colorless oil. Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 = (31.5 ± 2.9)μmol/L; K562, IC50 > 50 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). Ref: J. Zhang, et al, JNP, 2013, 76, 600 O

O O

63 Plakortoxide B Type: Butanolides. C18H30O3 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 > 50 μmol/L; K562, IC50 > 100 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). Ref: J. Zhang, et al, JNP, 2013, 76, 600 O

O O

64 Rubrolide R Type: Butanolides. C22H20O4 Colorless triclinic crystal. Source: Marine-derived fungus Aspergillus terreus OUCMDZ-1925. Pharm: Antioxidant (ABTS∙+ radicals, IC50 = 1.33 mmol/L); cytotoxic (K562, IC50 = 12.8 mmol/L). Ref: T. Zhu, et al, J. Antibiot., 2014, 67, 315

20

1 Oxygen Heterocycles

OH O O

OH

65 Rubrolide S Type: Butanolides. C22H20O4 Source: Marine-derived fungus Aspergillus terreus OUCMDZ-1925. Pharm: Antiviral (influenza virus (IFV) virus, IC50 = 87.1 μmol/L); cytotoxic (K562, IC50 = 12.8 mmol/L). Ref: T. Zhu, et al, J. Antibiot., 2014, 67, 315 O O O

OH

66 (5E)-Simplexolide Type: Butanolides. C18H32O3 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Antifungal (weak). Ref: X. -F. Liu, et al, Tetrahedron, 2012, 68, 4635

O

O 5E

OH

67 (5E)-Simplexolide A Type: Butanolides. C17H30O3 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Antifungal (weak). Ref: X. -F. Liu, et al, Tetrahedron, 2012, 68, 4635

O

O 5E

OH

1.3 Butanolides

21

68 (5Z)-Simplexolide A Type: Butanolides. C17H30O3 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Antifungal (weak). Ref: X. -F. Liu, et al, Tetrahedron, 2012, 68, 4635

O

O 5Z

OH

69 (5Z)-Simplexolide B Type: Butanolides. C17H30O3 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 = (4.7 ± 0.5)μmol/L; K562, IC50 = (2.2 ± 0.2)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). Ref: J. Zhang, et al, JNP, 2013, 76, 600

O

O

OH

70 (5E)-Simplexolide E Type: Butanolides. C17H30O3 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 = (31.2 ± 2.4)μmol/L; K562, IC50 = (49.2 ± 4.2)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). Ref: J. Zhang, et al, JNP, 2013, 76, 600

O

O

OH

71 Simplextone A Type: Butanolides. C18H32O4 Colorless cryst., [α]D23 = +28° (c = 0.085, CH3OH). Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (MTT assay, HCT116, IC50 = 26.3 μmol/L; SGC7901, IC50 = 57.4 μmol/L; HeLa, IC50 = 64.7 μmol/L; SW480, IC50 = 60.6 μmol/L). Ref: X. -F. Liu, et al, Org. Lett., 2011, 13, 3154

22

O

1 Oxygen Heterocycles

H

O

OH

HO

72 Simplextone B Type: Butanolides. C17H30O4 Colorless oil, [α]D23 = +21° (c = 0.085, CH3OH). Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (MTT assay, HCT116, IC50 = 23.7 μmol/L; SGC7901, IC50 = 45.8 μmol/L; HeLa, IC50 = 66.2 μmol/L; SW480, IC50 = 61.1 μmol/L). Ref: X. -F. Liu, et al, Org. Lett., 2011, 13, 3154

O

H

O

HO

OH

73 Simplextone C Type: Butanolides. C18H30O4 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 = (29.0 ± 2.0)μmol/L; K562, IC50 = (19.4 ± 1.0)μmol/L; A549, IC50 = (40.4 ± 3.5)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). Ref: J. Zhang, et al, JNP, 2013, 76, 600 O

O H H OH

OH

74 Simplextone D 4 Type: Butanolides. C17H30O4 Source: Sponge Plakortis simplex (Yongxing I., South China Sea, China). Pharm: Cytotoxic (HeLa, IC50 > 50 μmol/L; K562, IC50 > 100 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). Ref: J. Zhang, et al, JNP, 2013, 76, 600

1.3 Butanolides

O

23

O

H OH

OH

75 Spiculisporic acid B Type: Butanolides. C17H26O6 Source: Marine-derived fungus Aspergillus sp. HDf2 from urchin Anthocidaris crassispina (Qionghai, Hainan, China). Pharm: Antibacterial (Staphylococcus aureus, weak). Ref: R. Wang, et al, Molecules, 2012, 17, 13175 O O O OH

O

OH

76 Spiculisporic acid D Type: Butanolides. C18H30O6 Source: Marine-derived fungus Aspergillus sp. HDf2 from urchin Anthocidaris crassispina (Qionghai, Hainan, China). Pharm: Antibacterial (Staphylococcus aureus, weak). Ref: R. Wang, et al, Molecules, 2012, 17, 13175 O O O OH

O

OH

77 Tetracyclic salimabromide Type: Butanolides. C20H20Br2O3 Source: Marine myxobacterium Enhygromxya salina (sediment, Prerow I., Germany). Pharm: Antibacterial (bacterium Arthrobacter cristallopoietes, moderate). Ref: S. Felder, et al, Chem. Eur. J., 2013, 19, 9319

Br H O

H Br

O O

24

1 Oxygen Heterocycles

78 Tuberatolide A Type: Butanolides. C18H26O3 Source: Ascidian Botryllus tuberatus (Tong-Yeong City, R. O. Korea waters). Pharm: Farnesoid X receptor antagonist (potent). Ref: H. Choi, et al, JNP, 2011, 74, 90

O O

O

79 Tuberatolide B Type: Butanolides. C27H34O4 Source: Ascidian Botryllus tuberatus (Tong-Yeong City, R. O. Korea waters). Pharm: Farnesoid X receptor antagonist (potent). Ref: H. Choi, et al, JNP, 2011, 74, 90

O O

O

HO

80 2ʹ-epi-Tuberatolide B Type: Butanolides. C27H34O4 Source: Ascidian Botryllus tuberatus (Tong-Yeong City, R. O. Korea waters). Pharm: Farnesoid X receptor antagonist (potent). Ref: H. Choi, et al, JNP, 2011, 74, 90

O

O

2

O

HO

81 Tubingenoic anhydride A Type: Butanolides. C11H16O3 Source: Marine-derived fungus Aspergillus tubingensis OY907. Pharm: Antifungal (inhibits Neurospora crassa growth, MIC = 330 μmol/L, affected hyphal morphology). Ref: L. Koch, et al, Mar. Drugs, 2014, 12, 4713

1.4 Pyrans

25

O O H O

82 Zooxanthellactone Type: Butanolides. C22H30O2 Oil, [α]D27 = +64.6° (c = 0.24, CHCl3). Source: Dinoflagellates Symbiodinium spp. Pharm: Cytotoxic. Ref: K. Onodera, et al, Biosci., Biotechnol., Biochem., 2004, 68, 848-

O

O

1.4 Pyrans 83 Mycalamide C Type: Pyrans. C20H35NO8 Source: Sponge Stylinos sp. Pharm: Cytotoxic (P388, IC50 = 95 ng/mL). Ref: J. S. Simpson, et al, JNP, 2000, 63, 704 HO

O

O

OH

O

H N

OH

O

OH

84 NSC 646282 Type: Pyrans. C30H50N2O8 Oil, [α]D = −3.1° (c = 0.005, MeOH). Source: Marinederived bacterium Alteromonas sp. from sponge Darwinella rosacea. Pharm: Antimicrobial. Ref: D. B. Stierle, et al, Experientia, 1992, 48, 1165

HO

OH H

O O 7

O OH

O

H N

O NH

26

1 Oxygen Heterocycles

85 8-[(2-Oxo-3-piperidinyl)amino]-8-oxooctyl-5,9-anhydro-2,3,8-trideoxy8-(5-hydroxy-4-methyl-2-hexenyl)-3-methyl-DL-gly- cero-LD-allo-non-2-enoate Type: Pyrans. C30H50N2O9 Oil, [α]D = −1.8° (c = 0.003, MeOH). Source: Marinederived bacterium Alteromonas sp. from sponge Darwinella rosacea. Pharm: Antimicrobial. Ref: D. B. Stierle, et al, Experientia, 1992, 48, 1165 OH OH H

HO

O O 7

O

O

H N

O NH

OH

86 (+)-Pederin Type: Pyrans. C25H45NO9 mp 113 °C. Source: Insect Paederus fuscipes (toxic principle). Pharm: Dermatoxic; vesicant (hmn and animal skin). Ref: J. Piel, et al, JNP, 2005, 68, 472 (rev)│S. J. Robinson, et al, JNP, 2007, 70, 1002

O

O

O

O

OH

N H

OH O

O O

87 Vermelhotin 3-[6- (1-Propenyl)-2H-pyran-2-ylidene]-2,4-pyrrolidinedione Type: Pyrans. C12H11NO3 Equilib. 1:1 mixture of E– and Z–isomers, red needles (CH2Cl2/MeOH), mp 212–214 °C, mixt. of E– and Z–isomers (1:2) from CRI247–01. Source: Marine-derived fungus Nodulisporium sp. CRI247-01, an unidentified fungus IFM 52672. Pharm: Antiplasmodial (hmn erythrocytes type O infected by CRPF 94, IC50 = 1–10 μmol/L, control Chloroquine hydrochloride, IC50 = 0.29 μmol/L); cytotoxic (HuCCA-1, IC50 = 2.90 μg/mL; control Etoposide, IC50 = 5.30 μg/mL; KB, IC50 = 0.50 μg/mL, Etoposide, IC50 = 0.46 μg/mL; HeLa, IC50 = 0.33 μg/mL, Etoposide, IC50 = 0.40 μg/mL; MDA-MB-231, IC50 = 0.31 μg/mL, Etoposide, IC50 = 0.40 μg/mL; T47D, IC50 = 1.25 μg/mL, Etoposide, IC50 = 0.04 μg/mL; H69AR, IC50 = 2.50 μg/mL, Etoposide, IC50 = 36.0 μg/mL; HepG2, IC50 = 2.50 μg/mL, control Doxorubicin, IC50 = 0.19 μg/mL; A549, IC50 = 8.20 μg/mL, Doxorubicin, IC50 = 0.48 μg/mL; HCC-H102, IC50 = 13.5 μg/mL, Doxorubicin, IC50 = 1.20 μg/mL; HL60, IC50 = 1.60 μg/mL, Etoposide, IC50 = 0.77 μg/mL; P388, IC50 = 1.23 μg/mL Etoposide, IC50 = 0.10 μg/mL). Ref: T. Hosoe, et al, Heterocycles, 2006, 68, 1949│C. Kasettrathat, et al, Phytochemistry, 2008, 69, 2621

1.5 2-Pyrones (Pyranones; Pentanolides)

O

27

E

O H

N

O

88 Xestin A Type: Pyrans. C27H46O4 Cryst. (MeOH), mp 55–56 °C, [α]D20 = +26.5° (c = 0.37, CH2Cl2). Source: Sponge Xestospongia sp. Pharm: Cytotoxic (P388, IC50 = 0.3 μg/mL); cytotoxic (5 μg/mL, strong activity for A549, HCT8 and MDA-MB). Ref: E. Quinoa, et al, JOC, 1986, 51, 4260 O O

9

O O

89 Xestin B Type: Pyrans. C27H46O4 [α]D20 = +19.6° (c = 0.11, CH2Cl2). Source: Sponge Xestospongia sp. Pharm: Cytotoxic (P388, IC50 = 3 μg/mL). Ref: E. Quinoa, et al, JOC, 1986, 51, 4260 5

O O

11

O O

1.5 2-Pyrones (Pyranones; Pentanolides) 90 Albidopyrone Type: 2-Pyrones. C14H13NO4 Powder. Source: Marine-derived streptomycete Streptomyces sp. NTK 227. Pharm: Protein tyrosine phosphatase B inhibitor (moderate activity). Ref: C. Hohmann, et al, J. Antibiot., 2009, 62, 75 OH

O

O

O

N H

91 Asnipyrone A Type: 2-Pyrones. C21H22O3 Yellow cryst. (EtOH), mp 161–163 °C. Source: Mangrovederived fungus Alternaria niger from mangrove Avicennia marina (Dongzhai Harbour, Hainan, China). Pharm: Cytotoxic (A549, IC50 = 62 μmol/L, control Fluorouracil,

28

1 Oxygen Heterocycles

IC50 = 52 μmol/L). Ref: Guang-yi, L., et al, Heterocycles, 1989, 28, 899│D. Liu, et al, JNP, 2011, 74, 1787 O O O

92 Asnipyrone B Type: 2-Pyrones. C20H20O3 Yellow cryst. (MeOH/CH2Cl2), mp 158–160 °C. Source: Mangrove-derived fungus Alternaria niger from mangrove Avicennia marina (Dongzhai Harbour, Hainan, China). Pharm: Mycotoxin. Ref: Guang-yi, L., et al, Heterocycles, 1989, 28, 899│D. Liu, et al, JNP, 2011, 74, 1787 O O O

93 Aspyrone Type: 2-Pyrones. C9H12O4 Cryst. (C6H6 or Me2CO/petrol), mp 112–112.5 °C, [α]D = −14° (c = 1, EtOH). Source: Marine-derived fungus Exophiala sp., terrestrial fungi (Aspergillus spp.). Pharm: Antibiotic (broad-spectrum, weak). Ref: CRC Press, DNP on DVD, 2012, version 20.2 O

H

HO

O

O

94 Aspyronol Type: 2-Pyrones. C10H16O5 Colorless oil (MeOH), [α]D25 = −41.6° (c = 0.22, MeOH). Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, HL60, IC50 = 52.1 μg/mL (241.2 μmol/L); 100 μg/mL: HL60, InRt = 67.2%, control Docetaxol, InRt = 49.9%; HeLa, InRt = 14.0%, Docetaxol, InRt = 45.1%; K562, InRt = 27.9%, Docetaxol, InRt = 55.6%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116

1.5 2-Pyrones (Pyranones; Pentanolides)

29

O 9R

HO 8S

OH

95 Bitungolide A Type: 2-Pyrones. C25H33ClO5 Needles (MeOH aq), mp 179–182 °C, [α]D27 = +30° (c = 0.38, MeOH). Source: Lithistid sponge Theonella cf. swinhoei (along Lembeh Strait off Bitung, Sulawesi Island, Indonesia). Pharm: Dual-specificity protein phosphatase inhibitor (vaccinia H1-related (VHR), weak). Ref: S. Sirirath, et al, JNP, 2002, 65, 1820│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

OH

Cl

OH

12

HO 14

H

O

O

96 Bitungolide B Type: 2-Pyrones. C25H33ClO5 Amorph. solid, [α]D27 = +42° (c = 4.2, CHCl3). Source: Lithistid sponge Theonella cf. swinhoei (along Lembeh Strait off Bitung, Sulawesi Island, Indonesia). Pharm: Dual-specificity protein phosphatase inhibitor (vaccinia H1-related (VHR), weak). Ref: S. Sirirath, et al, JNP, 2002, 65, 1820│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

OH

Cl

OH

HO 14

H

12

O

O

97 Bitungolide C Type: 2-Pyrones. C25H33ClO5 Amorph. solid, [α]D27 = +89° (c = 0.11, CHCl3). Source: Lithistid sponge Theonella cf. swinhoei (along Lembeh Strait off Bitung, Sulawesi Island, Indonesia). Pharm: Dual-specificity protein phosphatase inhibitor (vaccinia H1-related (VHR), weak). Ref: S. Sirirath, et al, JNP, 2002, 65, 1820│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) Cl HO

OH

OH

12 14

H

O

O

30

1 Oxygen Heterocycles

98 Bitungolide D Type: 2-Pyrones. C25H33ClO5 Amorph. solid, [α]D27 = +66° (c = 0.58, CHCl3). Source: Lithistid sponge Theonella cf. swinhoei (along Lembeh Strait off Bitung, Sulawesi Island, Indonesia). Pharm: Dual-specificity protein phosphatase inhibitor (vaccinia H1-related (VHR), weak). Ref: S. Sirirath, et al, JNP, 2002, 65, 1820│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

OH

Cl

OH

12

HO 14

H

O

O

99 Bitungolide E Type: 2-Pyrones. C25H34O4 Pale yellow glass, [α]D27 = +107° (c = 1.3, CHCl3). Source: Lithistid sponge Theonella cf. swinhoei (along Lembeh Strait off Bitung, Sulawesi Island, Indonesia). Pharm: Dual-specificity protein phosphatase inhibitor (vaccinia H1-related (VHR), weak). Ref: S. Sirirath, et al, JNP, 2002, 65, 1820│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

OH

OH

H

O

O

100 Bitungolide F Type: 2-Pyrones. C24H32O4 Pale yellow glass, [α]D27 = +43° (c = 0.85, CHCl3). Source: Lithistid sponge Theonella cf. swinhoei (along Lembeh Strait off Bitung, Sulawesi Island, Indonesia). Pharm: Dual-specificity protein phosphatase inhibitor (vaccinia H1-related (VHR), weak). Ref: S. Sirirath, et al, JNP, 2002, 65, 1820│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

OH

OH H

O

O

101 Bromomethylchlamydosporol A Type: 2-Pyrones. C12H15BrO5 Source: Marine-derived fungus Fusarium tricinctum (adding calcium bromide to cultures) from brown alga Sargassum ringgoldianum (GeoMun

1.5 2-Pyrones (Pyranones; Pentanolides)

31

I., Yeosu, R. O. Korea). Pharm: Antibacterial (three strains of Staphylococcus aureus, MIC = 15.6 μg/mL). Ref: V. Nenkep, et al, JNP, 2010, 73, 2061 O O O

O

O

Br

102 Bromomethylchlamydosporol B Type: 2-Pyrones. C12H14Br2O5 Source: Marine-derived fungus Fusarium tricinctum (adding calcium bromide to cultures) from brown alga Sargassum ringgoldianum (GeoMun I., Yeosu, R. O. Korea). Pharm: Antibacterial (three strains of Staphylococcus aureus, MIC = 15.6 μg/mL). Ref: V. Nenkep, et al, JNP, 2010, 73, 2061 O Br

O O

O

O

Br

103 Callystatin A Type: 2-Pyrones. C29H44O4 Oil, [α]D = −107° (c = 0.1, MeOH). Source: Sponge Callyspongia truncata. (Japan waters). Pharm: Cytotoxic (KB, IC50 = 0.01 ng/mL). Ref: M. Kobayashi, et al, Tet. Lett., 1997, 38, 2859│N. Murakami, et al, Tet. Lett., 1997, 38, 5533 O O

OH

O

104 Chaetoquadrin F Type: 2-Pyrones. C9H12O4 Source: Deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C). Pharm: Cytotoxic (MTT method, 100 μg/mL: HeLa, InRt = 13.5%, control Docetaxol, InRt = 45.1%). Ref: X. Chen, et al, Mar. Drugs, 2014, 12, 3116 OH OH O

O

32

1 Oxygen Heterocycles

105 Chlamydosporol Type: 2-Pyrones. C11H14O5 Prisms (EtOAc), mp 172–174 °C. Source: Marine-derived fungus Fusarium tricinctum (adding calcium bromide to cultures) from brown alga Sargassum ringgoldianum (GeoMun I., Yeosu, R. O. Korea), terrestrial fungi (Fusarium acuminatum and Fusarium chlamydosporum). Pharm: Antibacterial (moderate). Ref: M. E. Savard, et al, Mycopathologia, 1990, 110, 177│J. F. Grove, et al, JCS Perkin I, 1991, 997│V. Nenkep, et al, JNP, 2010, 73, 2061 O O HO

O

O

106 Chlorohydroaspyrone A Type: 2-Pyrones. C9H13ClO4 Oil, [α]D20 = −110° (c = 0.1, MeOH). Source: Marinederived fungus Exophiala sp. from sponge Halichondria panicea (surface, Korea waters). Pharm: Antibacterial (mild: Staphylococcus aureus, MRSA, MDRSA). Ref: D. Zhang, et al, JNP, 2008, 71, 1458 Cl 2'S

HO 1'R

O

O

OH

107 Chlorohydroaspyrone B Type: 2-Pyrones. C9H13ClO4 Oil, [α]D20 = +70° (c = 0.1, MeOH). Source: Marinederived fungus Exophiala sp. from sponge Halichondria panicea (surface, Korea waters). Pharm: Antibacterial (mild: Staphylococcus aureus, MRSA, MDRSA). Ref: D. Zhang, et al, JNP, 2008, 71, 1458 OH 2'S

HO 1'S

Cl O

O

108 9-Chloro-8-hydroxy-8,9-deoxyaspyrone Type: 2-Pyrones. C10H15ClO3 [α]D26 = +17.2° (c = 0.17, CHCl3). Source: Marine-derived fungus Aspergillus ostianus TUF 01F313 from an unidentified sponge (Pohnpei I., Federated States of Micronesia). Pharm: Antibacterial (25 μg/disk, inhibits growth of Ruegeria atlantica, inhibition zone = 10.5 mm). Ref: M. Namikoshi, et al, J. Antibiot., 2003, 56, 755│M. Saleem, et al, NPR, 2007, 24, 1142 (rev)

1.5 2-Pyrones (Pyranones; Pentanolides)

33

OH HO

O

Cl O

109 Coibacin A Type: 2-Pyrones. C19H24O2 Source: Cyanobacterium Oscillatoria sp. (Coiba National Park, Panama). Pharm: Antileishmanial (selective); anti-inflammatory (potent). Ref: M. J. Balunas, et al, Org. Lett., 2012, 14, 3878

O O

110 Coibacin B Type: 2-Pyrones. C17H22O2 Source: Cyanobacterium Oscillatoria sp. (Coiba National Park, Panama). Pharm: Antileishmanial (selective); anti-inflammatory (potent). Ref: M. J. Balunas, et al, Org. Lett., 2012, 14, 3878

O O

111 Coibacin C Type: 2-Pyrones. C15H19ClO2 Source: Cyanobacterium Oscillatoria sp. (Coiba National Park, Panama). Pharm: Antileishmanial (selective); anti-inflammatory (potent). Ref: M. J. Balunas, et al, Org. Lett., 2012, 14, 3878 Cl O O

112 Coibacin D Type: 2-Pyrones. C15H21ClO2 Source: Cyanobacterium Oscillatoria sp. (Coiba National Park, Panama). Pharm: Antileishmanial (selective); anti-inflammatory (potent). Ref: M. J. Balunas, et al, Org. Lett., 2012, 14, 3878 Cl O O

34

1 Oxygen Heterocycles

113 9(13)-Cyclodiscodermolide Type: 2-Pyrones. C33H53NO7 Solid, [α]D21 = +24° (c = 0.01, MeOH). Source: Lithistid sponge Discodermia sp. (numerous places, Bahamas, using Johnson-Sea-Link submersible). Pharm: Cytotoxic (P388, IC50 = 5043 nmol/L; A549, IC50 = 4487 nmol/L). Ref: S. P. Gunasekera, et al, JNP, 2002, 65, 1643│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev) O OH

O

O

NH2

O

OH OH

114 Cyercene 1 4-Methoxy-3-methyl-6- (3-methyl-1,3-pentadienyl)-2H-pyran-2-one Type: 2-Pyrones. C13H16O3 Source: Sacoglossan Cyerce cristallina. Pharm: Ichthyotoxic. Ref: R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569 O

O

O

115 Cyercene 2 4-Methoxy-3-methyl-6-(3-methyl-1,3-hexadienyl)-2H-pyran-2-one Type: 2-Pyrones. C14H18O3 Source: Sacoglossan Cyerce cristallina. Pharm: Ichthyotoxic. Ref: R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569 O

O

O

116 Cyercene 3 6- (3,5-Dimethyl-1,3-hexadienyl)-4-methoxy-3-methyl-2H-pyran-2-one Type: 2-Pyrones. C15H20O3 Source: Sacoglossan Cyerce cristallina. Pharm: Ichthyotoxic. Ref: R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569

1.5 2-Pyrones (Pyranones; Pentanolides)

35

O

O

O

117 Cyercene 4 6-(1,3-Dimethyl-1,3-pentadienyl)-4-methoxy-5-methyl-2H-pyran-2-one Type: 2-Pyrones. C14H18O3 Source: Sacoglossan Cyerce cristallina. Pharm: Ichthyotoxic. Ref: R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569 O

O

O

118 Cyercene 5 6-(1,3-Dimethyl-1,3-hexadienyl)-4-methoxy-5-methyl-2H-pyran-2-one Type: 2-Pyrones. C15H20O3 Source: Sacoglossan Cyerce cristallina. Pharm: Ichthyotoxic. Ref: V. Roussis, et al, Experientia, 1990, 46, 327│R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569 O

O

O

119 19-Deaminocarbonyldiscodermolide Type: 2-Pyrones. C32H54O7 Solid, [α]D21 = +18° (c = 0.1, MeOH). Source: Lithistid sponge Discodermia sp. (numerous places, Bahamas, using Johnson-Sea-Link submersible). Pharm: Cytotoxic (P388, IC50 = 128 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)

O

O 2

OH OH

OH OH

OH

36

1 Oxygen Heterocycles

120 8,9-Dehydroxylarone Type: 2-Pyrones. C13H16O3 Source: Sacoglossan Aplysiopsis formosa (herbivorous, Azores Is.). Pharm: Cytotoxic (Colo320, IC50 = 25 μg/mL; L1210, C50 = 25 μg/mL; HL60, IC50 = 50 μg/mL); antibacterial (Micrococcus luteus, 100 μg/mL). Ref: A. Schuffler, et al, Z. Naturforsch. C., 2007, 62c, 169 O

O

O

121 2-Demethyldiscodermolide Type: 2-Pyrones. C32H53NO8 Solid, [α]D21 = +10.2° (c = 0.1, MeOH). Source: Lithistid sponge Discodermia sp. (numerous places, Bahamas, using Johnson-Sea-Link submersible). Pharm: Cytotoxic (P388, IC50 = 172 nmol/L; A549, IC50 = 120 nmol/L). Ref: S. P. Gunasekera, et al, JNP, 2002, 65, 1643│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

O

O 2

OH OH

OH

O

NH2 O

OH

122 Diemenensin A 4-Hydroxy-3,5-dimethyl-6-(1,3,5,7-tetramethyl-1,3-decadienyl)-2H-pyran-2-one Type: 2-Pyrones. C21H32O3 Oil, [α]D = +77.3° (c = 4.7, MeOH). Source: Pulmonate limpet Siphonaria diemenensis (Australia). Pharm: Antibacterial (Staphylococcus aureus and Bacillus subtilis). Ref: J. E. Hochlowski, et al, Tet. Lett., 1983, 24, 1917

1'

O

O

OH

123 Diemenensin B Type: 2-Pyrones. C21H32O3 Oil, [α]D = +32.4° (c = 1.15, MeOH). Source: Pulmonate limpet Siphonaria diemenensis (Australia). Pharm: Antibacterial. Ref: J. E. Hochlowski, et al, Tet. Lett., 1983, 24, 1917

1.5 2-Pyrones (Pyranones; Pentanolides)

O

37

1'

O

OH

124 Dihydroaspyrone Type: 2-Pyrones. C9H14O4 [α]D20 = +17.8° (c = 0.7, MeOH). Source: Marine-derived fungus Aspergillus ostianus 01F313 from an unidentified sponge (Pohnpei I., Federated States of Micronesia), deep-sea fungus Aspergillus sp. 16-02-1 from sediment (Lau Basin hydrothermal vent, depth of 2255 m, temperature 114 °C), terrestrial fungus (Aspergillus ochraceus). Pharm: Cytotoxic (MTT method, 100 μg/mL: HL60, InRt = 19.9%, control Docetaxol, InRt = 49.9%, HeLa, InRt = 10.1%, Docetaxol, InRt = 45.1%). Ref: J. Fuchser, et al, Liebigs Ann./Recl., 1997, 87│K. Kito, et al, JNP, 2007, 70, 2022│X. Chen, et al, Mar. Drugs, 2014, 12, 3116 9S

HO 8

OH O

O

125 3′,4′-Dihydroinfectopyrone Type: 2-Pyrones. C14H18O5 Source: Marine-derived fungus Petriella sp. TUBS 7961 from sponge Suberites domuncula (Mediterranean Sea). Pharm: Cytotoxic (L5178Y, pronounced activity). Ref: P. Proksch, et al, Bot. Mar., 2008, 51, 209 O

O

OH

O O

126 5,7-Dihydroxy-2-[[1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]amino]1,4-naphthoquinone Type: 2-Pyrones. C24H19NO7 Amorph. red powder, mp 118–120 °C, [α]D25 = +54.9° (c = 0.19, CHCl3). Source: Marine-derived fungus Aspergillus niger EN-13 from brown alga Colpomenia sinuosa (China waters). Pharm: Antifungal (Candida albicans, moderate). Ref: Y. Zhang, et al, Chin. Chem. Lett., 2007, 18, 951

38

1 Oxygen Heterocycles

O O

H N

HO

OH

O

O

O

127 Discodermolide Disermolide Type: 2-Pyrones. C33H55NO8 Cryst., mp 115–116 °C, [α]D22 = +7.2° (c = 0.72, MeOH). Source: Lithistid sponge Discodermia dissoluta (depth of 33 m, off Grand Bahama I., Caribbean Sea). Pharm: Arrests cells in G2/M phase of cell cycle; cytotoxic (breast cancer MDA-MB-231, GI50 = 0.029 μmol/L; non-small-cell lung cancer A549, GI50 = 0.020 μmol/L; colon cancer HT29, GI50 = 0.015 μmol/L); cytotoxic (P388 cell line, IC50 = 35 nmol/L; A549 cell line, IC50 = 13.5 nmol/L); cytotoxic (inhibits cell proliferation by polymerizing and hyperstabilizing tubulin, similar to paclitaxel but shows activity against paclitaxel resistant tumors); potent promotor of tubulin assembly (similar to paclitaxel); immunosuppressant. Ref: S. P. Gunasekera, et al, JOC, 1990, 55, 4912; 1991, 56, 1346│R. E. Longley, et al, Ann. N.Y. Acad. Sci., 1993, 696, 94│L. E. Broker, et al, Cancer Res., 2002, 62, 4081│G. J. Florence, et al, Nat. Prod. Rep., 2008, 25, 342│A. B. Smith, et al, Tetrahedron, 2008, 64, 261│ P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

O

O 2

OH OH

OH OH

O

O NH2

128 2-epi-Discodermolide Type: 2-Pyrones. C33H55NO8 Solid, [α]D21 = +10.7° (c = 0.1, MeOH). Source: Lithistid sponge Discodermia sp. (numerous places, Bahamas, using Johnson-Sea-Link submersible). Pharm: Cytotoxic (P388, IC50 = 134 nmol/L; A549, IC50 = 67 nmol/L). Ref: S. P. Gunasekera, et al, JNP, 2002, 65, 1643│P. L. Winder, et al, Mar. Drugs, 2011, 9, 2644 (rev)

O

O 2

OH OH

OH OH

O

NH2 O

1.5 2-Pyrones (Pyranones; Pentanolides)

39

129 Harzialactone B Type: 2-Pyrones. C7H10O3 Oil, [α]D32 = −23.5° (c = 1.76, CHCl3). Source: Marinederived fungus Trichoderma harzianum OUPS-N115 from sponge Halichondria okadai. Pharm: Cytotoxic (cultured P388, ED50 = 60.0 μg/mL). Ref: T. Amagata, et al, J. Antibiot., 1998, 51, 33 OH

O

O

130 Helicascolide C Type: 2-Pyrones. C12H18O3 Source: Marine-derived fungi Curvularia eschscholzii from red alga Gracilaria sp. (South Sulawesi coast, Indonesia) and Daldinia eschscholzii KT32 (algicolous, Indonesia). Pharm: Antifungal (phytopathogenic fungus Cladosporium cucumerinum, 200 μg/disk, IZ = 5 mm). Ref: K. Tarman, et al, Phytochem. Lett., 2012, 5, 83 O O

H

O

131 (E)-6-(1-Heptenyl)-2H-pyran-2-one Type: 2-Pyrones. C12H16O2 Oil. Source: Marine-derived fungus Botrytis sp. from red alga Hyalosiphonia caespitosa (Korea waters). Pharm: Tyrosinase inhibitor (IC50 = 4.5 μmol/L, more active than control kojic acid). Ref: D. Zhang, et al, Bull. Korea waters watersn Chem. Soc., 2007, 28, 887

O

O

132 5-Hydroxy-4-(hydroxymethyl)-2H-pyran-2-one Type: 2-Pyrones. C6H6O4 Cryst. (MeOH), mp 138–140 °C. Source: Marine-derived fungus Aspergillus flavus C-F-3 from green alga Enteromorpha tubulosa (China waters). Pharm: Induces production of cAMP (GPR12 transfected CHO and HEK-293, in a dose-dependent manner, it might be possible ligand for GPR12, which can be significant molecular target for treating a variety of neurological disorders). Ref: A. Lin, et al, J. Antibiot., 2008, 61, 245

40

1 Oxygen Heterocycles

O O HO OH

133 Hydroxypestalopyrone Type: 2-Pyrones. C10H12O4 Powder. Source: Marine-derived fungus Nigrospora sp. PSU-F5. Pharm: Antifungal. Ref: K. Trisuwan, et al, JNP, 2008, 71, 1323 O

HO

O

O

134 Isopectinatone Type: 2-Pyrones. C21H34O3 Oil, [α]D25 = +35° (c = 0.1, CHCl3). Source: Pulmonate limpet Siphonaria pectinata (Cádiz, Spain, W6°18´ N36°32´). Pharm: Cytotoxic (P388, A549, HT29 and MEL28, ED50 = 2.5 μg/mL). Ref: M. C. Paul, et al, Tetrahedron, 1997, 53, 2303

O

O

OH

135 Lagunapyrone B Type: 2-Pyrones. C34H52O5 [α]D20 = +10.9° (c = 4, MeOH). Source: Marine-derived actinomycete Actinomyces sp. CNB-984 (shallow water marine sediment, Southern California). Pharm: Cytotoxic (HCT116, ED50 = 3.5 μg/mL). Ref: T. Lindel, et al, Tet. Lett., 1996, 37, 1327 OH

OH

OH O

O

136 Lehualide E Type: 2-Pyrones. C24H34O4 Source: Sponge Plakortis sp. (‘Eua I., Tonga). Pharm: The lehualides were moderately toxic to sensitised yeast cells but not to wild type and are therefore susceptible to efflux pump action. Ref: J. M. Barber,et al, JNP, 2011, 74, 809

1.5 2-Pyrones (Pyranones; Pentanolides)

O

41

O

6

O O

137 (–)-Malyngolide Type: 2-Pyrones. C16H30O3 Crystal, mp 36–38 °C, [α]D20 = −13.0° (c = 0.9, CHCl3); mp 36–37 °C, [α]D = −13° (c = 2, CHCl3). Source: Cyanobacterium Lyngbya majuscula. Pharm: Antibacterial (Mycobacterium smegmatis, Streptococcus pyogenes). Ref: J. H. Cardellina II, et al, JOC, 1979, 44, 4039│S. Ohira, et al, J. Chem. Soc., Chem. Commun., 1993, 1299│D. Enders, et al, Tetrahedron, 1996, 52, 5805│H. Flörke, et al, Liebigs Ann. Chem., 1996, 147│S. Sankaranarayanan, et al, Tetrahedron: Asymmetry, 1996, 7, 2639│S. Ohira, et al, JCS Perkin I, 1998, 293│E. Winter, et al, Tetrahedron, 1998, 54, 10329│N. Maezaki, et al, Tetrahedron, 1998, 54, 13087│ K. Matsuo,, Heterocycles, 1998, 48, 1213 O O

OH

138 Malyngolide dimer Type: 2-Pyrones. C32H60O6 Source: Cyanobacterium Lyngbya majuscula (Coiba National Park, Panama). Pharm: Antiplasmodial (in vitro, CRPF W2, moderate); cytotoxic (H460). Ref: M. Guti-errez, et al, JNP, 2010, 73, 709 O OH O 7 7

O

HO O

139 7-Methylcyercene 1 Type: 2-Pyrones. C14H18O3 Solid. Source: Sacoglossan Ercolania funerea (Mediterranean Sea). Pharm: Phytotoxin. Ref: R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569; 1992, 48, 9561

42

1 Oxygen Heterocycles

O

O

O

140 Nectriapyrone A Type: 2-Pyrones. C11H14O3 Cryst., mp 111–112 °C. Source: Marine-derived fungus from sponge Stylotella sp. Pharm: Melanin biosynthesis inhibitor. Ref: L. M. Abrell, et al, Tet. Lett., 1994, 35, 9159 O O O

141 Neofusapyrone Type: 2-Pyrones. C34H54O9 Oil, [α]D20 = −23.6° (c = 1, MeOH). Source: Marine-derived fungus Fusarium sp. FH-146 (driftwood, Japan waters). Pharm: Antifungal (Aspergillus clavatus F318a, MIC = 6.26 μg/mL; control Amphotericin B, MIC = 0.15 μg/mL Candida albicans ATCC 2019, MIC > 100 μg/mL; Amphotericin B, MIC = 0.62 μg/mL); antibacterial (Pseudomonas aeruginosa ATCC 15442, MIC > 100 μg/mL; control Chloramphenicol, MIC = 1.25 μg/mL; Staphylococcus aureus NBRC 13276, MIC > 100 μg/mL; Chloramphenicol, MIC = 5 μg/mL). Ref: F. Hiramatsu, et al, J. Antibiot., 2006, 59, 704 OH O O

H

OH

O OH

OH

OH

26

OH

142 Neurymenolide A Type: 2-Pyrones. C24H32O3 Oil, [α]D24 = −150° (c = 0.02, MeOH). Source: Red alga Neurymenia fraxinifolia (Taveuni I., Fiji). Pharm: Antibacterial (MRSA, IC50 = 2.1 μmol/L; VREF, IC50 = 4.5 μmol/L; tuberculosis, IC50 > 100 μmol/L); cytotoxic (mean of 12 cell lines, IC50 = 8.8 μmol/L; DU4475, IC50 = 3.9 μmol/L); antimalarial (IC50 = 68 μmol/L); antifungal (ABRCA, IC50 > 600 μmol/L). Ref: E. P. Stout, et al, Org. Lett., 2009, 11, 225; 1865

1.5 2-Pyrones (Pyranones; Pentanolides)

43

OH

O

O

143 Neurymenolide B Type: 2-Pyrones. C26H36O3 Oil, [α]D24 = −240° (c = 0.02, MeOH). Source: Red alga Neurymenia fraxinifolia (Taveuni I., Fiji). Pharm: Antibacterial (MRSA, IC50 = 7.8 μmol/L; VREF, IC50 = 31 μmol/L; tuberculosis, IC50 > 100 μmol/L); cytotoxic (mean of 12 cell lines, IC50 = 39 μmol/L; DU4475, IC50 = 19 μmol/L); antimalarial (IC50 > 100 μmol/L); antifungal (ABRCA, IC50 > 600 μmol/L). Ref: E. P. Stout, et al, Org. Lett., 2009, 11, 225; 1865

OH

O

O

144 Nigerapyrone B Type: 2-Pyrones. C21H20O3 Yellowish amorph. powder. Source: Mangrove-derived fungus Alternaria niger from mangrove Avicennia marina, (Dongzhai Harbour, Hainan, China). Pharm: Cytotoxic (HepG2, IC50 = 62 μmol/L, control Fluorouracil, IC50 = 109 μmol/L). Ref: D. Liu, et al, JNP, 2011, 74, 1787 O O O

145 Nigerapyrone D Type: 2-Pyrones. C14H16O4 Yellowish amorph. powder. Source: Mangrove-derived fungus Alternaria niger from mangrove Avicennia marina, (Dongzhai Harbour, Hainan, China). Pharm: Cytotoxic (MCF7, IC50 = 121 μmol/L, control Fluorouracil, IC50 = 31 μmol/L; HepG2, IC50 = 81 μmol/L, Fluorouracil, IC50 = 109 μmol/L; A549, IC50 = 81 μmol/L, Fluorouracil, IC50 = 52 μmol/L). Ref: D. Liu, et al, JNP, 2011, 74, 1787

44

1 Oxygen Heterocycles

O O O O

146 Nigerapyrone E Type: 2-Pyrones. C11H12O4 Yellowish amorph. powder. Source: Mangrove-derived fungus Alternaria niger from mangrove Avicennia marina, (Dongzhai Harbour, Hainan, China). Pharm: Cytotoxic (A549, IC50 = 43 μmol/L control Fluorouracil, IC50 = 52 μmol/L; MDA-MB-231, IC50 = 48 μmol/L, Fluorouracil, IC50 = 59 μmol/L; SW1990, IC50 = 38 μmol/L, Fluorouracil, IC50 = 121 μmol/L; MCF7, IC50 = 105 μmol/L, Fluorouracil, IC50 = 31 μmol/L; HepG2, IC50 = 86 μmol/L, Fluorouracil, IC50 = 109 μmol/L; DU145, IC50 = 86 μmol/L, Fluorouracil, IC50 = 3.3 μmol/L; NCI-H460, IC50 = 43 μmol/L, Fluorouracil, IC50 = 8.5 μmol/L; MDA-MB-231, IC50 = 48 μmol/L, Fluorouracil, IC50 = 59 μmol/L). Ref: D. Liu, et al, JNP, 2011, 74, 1787 O O O O

147 Nigrosporapyrone A Type: 2-Pyrones. C18H22O5 Gum, [α]D29 = −254° (c = 0.1, CHCl3). Source: Marinederived fungus Nigrospora sp. PSU-F18 from gorgonian sea fan Annella sp. (Similan Is., Thailand). Pharm: Antibacterial (Staphylococcus aureus ATCC 25923, MIC = 128 μg/mL, MRSA, MIC = 128 μg/mL). Ref: K. Trisuwan, et al, Phytochemistry, 2009, 70, 554 O 1''

O

O 4'

O H 2 5

H OH

148 Pectinatone 4-Hydroxy-3,5-dimethyl-6-(1,3,5,7-tetramethyl-1-decenyl)-2H-pyran-2-one Type: 2-Pyrones. C21H34O3 Cryst. (CH2Cl2), mp 127–129 °C, [α]D20 = +62° (c = 0.184, CHCl3).

1.5 2-Pyrones (Pyranones; Pentanolides)

45

Source: Pulmonate limpets Siphonaria pectinata (Cádiz, Spain, W6°18´ N36°32´) and Siphonaria grisea. Pharm: Cytotoxic (P388, A549, HT29 and MEL28, all ED50 = 5 μg/mL); antibacterial (gram-positive bacteria, Bacillus subtilis); antifungal (Candida albicans, yeast Saccharomyces cerevisiae). Ref: J. E. Biskupiak, et al, Tet. Lett., 1983, 24, 3055│M. J. Garson, et al, JCS Perkin I, 1990, 805│M. Norte, et al, Tetrahedron, 1990, 46, 1669│M. C. Paul, et al, Tetrahedron, 1997, 53, 2303│ A. A. Birkbeck, et al, Tet. Lett., 1998, 39, 7823

O

O

OH

149 Penicitide A Type: 2-Pyrones. C18H34O4 Colorless oil, [α]D20 = +42.9° (c = 0.14, MeOH). Source: Marine-derived fungus Penicillium chrysogenum QEN-24S [Syn. Penicillium chrysogenum] from red alga Laurencia sp. (Weizhou I., Guangxi, China). Pharm: Antifungal (20 μg/disk, Aspergillus brassicae, IZD = 6 mm, control Amphotericin B, IZD = 18 mm; Aspergillus niger, slight inhibition, Amphotericin B, IZD = 24 mm); Cytotoxic (HepG2, moderate). Ref: S. -S. Gao, et al, Mar. Drugs, 2011, 9, 59 O OH

O OH

3

150 Peniphenone B Type: 2-Pyrones. C21H18O8 Source: Marine fungus Penicillium dipodomyicola. Pharm: Antituberculosis (Mycobacterium tuberculosis, strongly inhibits mycobacterial Protein tyrosine phosphatase B, MptpB). Ref: H. Li, et al, JNP 2014, 77, 800 OH OH HO O

HO O

O OH

46

1 Oxygen Heterocycles

151 Phomalactone Antibiotic LL-Z 1276 Type: 2-Pyrones. C8H10O3 mp 50–53 °C, [α]D22 = +179° (CHCl3). Source: Marine-derived fungus Nigrospora sp. PSU-F18. Pharm: Antibacterial (Pseudomonas spp., Trichophyton spp.); phytotoxin; herbicide. Ref: K. Trisuwan, et al, Phytochemistry, 2009, 70, 554 HO H O

O

152 Phomapyrone C Type: 2-Pyrones. C10H14O3 Film, [α]D = −16.1° (c = 0.28, CHCl3). Source: Marinederived fungus Paecilomyces lilacinus. Pharm: Phytotoxin. Ref: M. S. C. Pedras, et al, Phytochemistry, 1994, 36, 1315│M. Elbandy, et al, Bull. Korea waters watersn Chem. Soc., 2009, 30, 188 OH

O

O

153 Phomopsis H76C Type: 2-Pyrones. C30H16N2O12 Yellow powder, mp 317–320 °C. Source: Mangrovederived fungus Phomopsis sp. ZSU-H76 from mangrove Excoecaria agallocha (China waters). Pharm: Blood vessel growth inhibitor. Ref: J. -X. Yang, et al, EurJOC, 2010, 3692 OH O

O N

O

O O

O O

O

N O

O

OH

154 Pseudopyronine A Type: 2-Pyrones. C16H26O3 Powder. Source: Marine bacterium Pseudomonas sp. F92S91. Pharm: Antibacterial (including MRSA). Ref: M. P. Singh, et al, J. Antibiot., 2003, 56, 1033

1.5 2-Pyrones (Pyranones; Pentanolides)

47

OH

O

O

155 Pterocidin Type: 2-Pyrones. C23H34O6 Pale yellow oil, [α]D20 = −27.7° (c = 0.46, CHCl3). Source: Marine-derived streptomycetes Streptomyces hygroscopicus TP-A0451 and Streptomyces sp. (sediment, Otsuchi Bay, Japan waters). Pharm: Cytotoxic. Ref: Y. Igarashi, et al, J. Antibiot., 2006, 59, 193│Y. Igarashi, et al, Tet. Lett., 2012, 53, 654 O

O

O

OH

O O

156 Pyrenocine A Citreopyrone Type: 2-Pyrones. C11H12O4 Cryst. (MeOH), mp 110.9–111.6 °C. Source: Marine-derived fungus Penicillium waksmanii. Pharm: Cytotoxic; plant growth inhibitor. Ref: T. Amagata, et al, J. Antibiot., 1998, 51, 432 O

O

O

O

157 Pyrenocine B Type: 2-Pyrones. C11H14O5 Cryst. (Et2O/hexane), mp 103–103.5 °C, [α]D20 = +0.03° (c = 0.56, CHCl3). Source: Marine-derived fungus Penicillium waksmanii. Pharm: Cytotoxic; phytotoxin. Ref: T. Amagata, et al, J. Antibiot., 1998, 51, 432 OH

O

O

O

O

158 Pyrenocine E Type: 2-Pyrones. C12H16O5 Powder, mp 82–84 °C. Source: Marine-derived fungus Penicillium waksmanii OUPS-N133 from brown alga Sargassum ringgoldianum.

48

1 Oxygen Heterocycles

Pharm: Cytotoxic (P388, ED50 = 1.30 μg/mL). Ref: T. Amagata, et al, J. Antibiot., 1998, 51, 432 O

O

O O

O

159 Salinipyrone A Type: 2-Pyrones. C17H24O4 Yellow oil, [α]D = −87° (c = 0.33, MeOH). Source: Marinederived actinomycete Salinispora pacifica CNS-237. Pharm: Anti-inflammatory (mouse splenocyte IL-5 inhibitor, IC50 = 10 μg/mL). Ref: D. -C. Oh, et al, JNP, 2008, 71, 570 OH OH 3'

O

O

160 Simplactone A Type: 2-Pyrones. C7H12O3 Amorph. solid, [α]D25 = −3° (c = 0.002, CHCl3). Source: Sponge Plakortis simplex (Caribbean Sea). Pharm: Cytotoxic (WEHI-164, IC50 = 20 μg/mL). Ref: F. Cafieri, et al, Tetrahedron, 1999, 55, 13831 O

HO O

161 Simplactone B Type: 2-Pyrones. C7H12O3 Amorph. solid, [α]D25 = −6° (c = 0.001, CHCl3). Source: Sponge Plakortis simplex (Caribbean Sea). Pharm: Cytotoxic (WEHI-164, IC50 = 20 μg/mL). Ref: F. Cafieri, et al, Tetrahedron, 1999, 55, 13831 HO

O O

162 Solanapyrone A Type: 2-Pyrones. C18H22O4 Oil, [α]D = −67.3° (c = 2.26, CHCl3). Source: Marinederived fungus Nigrospora sp. PSU-F18. Pharm: Phytotoxin. Ref: A. Ichihara, et al, Tet. Lett., 1983, 24, 5373; 1985, 26, 2453; 1987, 28, 1175

1.5 2-Pyrones (Pyranones; Pentanolides)

1''

49

O

O

O 4'

O H 2 5

H

163 Solanapyrone C Type: 2-Pyrones. C19H25NO4 Oil, [α]D = −5° (c = 0.88, CHCl3). Source: An unidentified marine-derived fungus from green alga Halimeda monile (surface). Pharm: Antialgal (green alga Dunaliella sp., EC = 100 μg/mL); phytotoxin. Ref: A. Ichihara, et al, Tet. Lett., 1983, 24, 5373; 1985, 26, 2453; 1987, 28, 1175│K. M. Jenkins, et al, Phytochemistry, 1998, 49, 2299

1''

O H N

O 4'

OH

O H 2 5

H

164 Solanapyrone E Type: 2-Pyrones. C18H24O4 Oil, [α]D22 = −76.4° (c = 1, CHCl3). Source: An unidentified marine fungus. Pharm: Antialgal (green alga Dunaliella sp., EC = 100 μg/mL). Ref: K. M. Jenkins, et al, Phytochemistry, 1998, 49, 2299 OH 1''

O

O 4'

O H 2 5

H

165 7β-Solanapyrone F Type: 2-Pyrones. C17H21NO4 Solid, [α]D25 = −16.4° (c = 0.28, MeOH). Source: An unidentified marine-derived fungus CNC-159 cultured from green alga Halimeda

50

1 Oxygen Heterocycles

monile (surface). Pharm: Algicide (green alga Dunaliella sp., EC = 100 μg/mL). Ref: K. M. Jenkins, et al, Phytochemistry, 1998, 49, 2299

1''

O

O

NH2 4'

O H 2 5

OH

H

166 Solanapyrone F Type: 2-Pyrones. C17H21NO4 Solid, [α]D25 = −53.2° (c = 0.3, MeOH). Source: An unidentified marine-derived fungus CNC-159 cultured from green alga Halimeda monile (surface). Pharm: Antialgal (green alga Dunaliella sp., EC = 100 μg/mL). Ref: K. M. Jenkins, et al, Phytochemistry, 1998, 49, 2299

1''

O

O

NH2 4'

O H 2 5

OH

H

167 Solanapyrone G Type: 2-Pyrones. C17H21NO3 Solid. Source: An unidentified marine-derived fungus from green alga Halimeda monile (surface). Pharm: Antialgal (green alga Dunaliella sp., EC = 100 μg/mL). Ref: K. M. Jenkins, et al, Phytochemistry, 1998, 49, 2299 1''

O

O

NH2 4'

O H 2 5

H

1.5 2-Pyrones (Pyranones; Pentanolides)

51

168 (+)-Tanikolide Type: 2-Pyrones. C17H32O3 Oil, [α]D25 = +2.3° (c = 0.65, CHCl3). Source: Cyanobacterium Lyngbya majuscula (Madagascar). Pharm: Antifungal (paper diskagar plate assay, Candida albicans, 100 μg/disk, IZD = 13 mm); molluscacidal (snail vector Biomphalaria glabrata, LD50 = 31.6 μmol/L); LD50 (brine shrimp) = 3.6 μg/ mL, (snail) = 9.0 μg/mL. Ref: I. P. Singh, et al, JNP, 1999, 62, 1333│R. M. Kanada, et al, Synlett, 2000, 1019│A. R. Pereira, et al, JNP, 2010, 73, 217 O O

OH

169 Verrucosidin Type: 2-Pyrones. C24H32O6 Plates (Et2O), mp 90–91 °C, [α]D26 = +92.4° (c = 0.25, MeOH). Source: Marine-derived fungus Penicillium aurantiogriseum (mud, Bohai Sea, China), terrestrial fungi (Penicillium verrucosum var. cyclopium and Penicillium variabile). Pharm: Neurotoxin (potent). Ref: M. Ganguli, et al, JOC, 1984, 49, 3762│S. Nishiyama, et al, Tet. Lett., 1986, 27, 723│A. A. El-Banna, et al, Microbiol., Aliments, Nutr., 1987, 5, 191; 1989, 7, 161│J. K. Cha, et al, Tet. Lett., 1987, 28, 5473│K. Yu, et al, Mar. Drugs, 2010, 8, 2744 O 3

O O

H

O

O O

170 Xylarone Aplysiopsene C Type: 2-Pyrones. C13H18O3 Oil. Source: Sacoglossan Aplysiopsis formosa (herbivorous, Azores Is.). Pharm: Cytotoxic (Colo320, IC50 = 40–50 μg/mL; L1210, C50 = 50 μg/mL). Ref: A. Schüffler, et al, Z. Naturforsch., C, 2007, 62, 169│M. L. Ciavatta, et al, Tet. Lett., 2009, 50, 527 O

O

O

52

1 Oxygen Heterocycles

1.6 Nonadrides 171 (–)-Byssochlamic acid Type: Nonadrides. C18H20O6 Cryst. (EtOAc/petrol or CHCl3), mp 164–165 °C, [α]D23 = −104° (c = 0.1, CHCl3). Source: An unidentified mangrove-derived fungus k38 (South China Sea). Pharm: Cytotoxic (Hep2, IC50 = 37 μg/mL, HepG2, IC50 = 35 μg/mL). Ref: C. Y. Li, et al, Chem. Nat. Compd., 2006, 42, 290│C. -Y. Li, et al, J. Asian Nat. Prod. Res., 2007, 9, 285

O

O

O

O O

O

1.7 4-Pyrones (γ-Pyrones) 172 Auripyrone A Type: 4-Pyrones. C33H50O7 Cryst. (pentane), mp 172–176 °C, [α]D26 = +28° (c = 0.08, CHCl3). Source: Sea hare Dolabella auricularia. Pharm: Cytotoxic. Ref: K. Suenaga, et al, Tet. Lett., 1996, 37, 5151│I. Hayakawa, et al, Angew. Chem., Int. Ed., 2010, 49, 2401

O O

O O

O

H

O O

173 Auripyrone B Type: 4-Pyrones. C33H50O7 Cryst. (pentane), mp 126–128 °C, [α]D26 = +39° (c = 0.14, CHCl3). Source: Sea hare Dolabella auricularia. Pharm: Cytotoxic. Ref: K. Suenaga, et al, Tet. Lett., 1996, 37, 5151│I. Hayakawa, et al, Angew. Chem., Int. Ed., 2010, 49, 2401

1.7 4-Pyrones (γ-Pyrones)

53

O O

O O

O 11

O

S

O

H

174 Bissetone Type: 4-Pyrones. C9H14O5 Oil, [α]D = −43.6° (c = 4.25, EtOH). Source: Gorgonian Briareum polyanthes. Pharm: Antimicrobial; insecticide; plant growth regulator. Ref: J. H. Cardellina, et al, Tet. Lett., 1987, 28, 727 O OH

O

OH

O

175 Carbonarone A 6-Benzyl-4-oxo-4H-pyran-3-carboxamide Type: 4-Pyrones. C13H11NO3 Amorph. yellow powder. Source: Marine-derived fungus Aspergillus carbonarius WZ-4-11. Pharm: Cytotoxic (K562, IC50 = 56.0 μg/mL). Ref: Y. P. Zhang, et al, J. Antibiot., 2007, 60, 153 O

O NH2

O

176 Carbonarone B Type: 4-Pyrones. C13H11NO3 Needles, mp 209–209.5 °C. Source: Marine-derived fungus Aspergillus carbonarius WZ-4-11. Pharm: Cytotoxic (K562, IC50 = 50.6 μg/mL, with antiproliferative activity). Ref: Y. Zhang, et al, J. Antibiot., 2007, 60, 153 OH O N H

O

177 Chromanone Type: 4-Pyrones. C18H18O6 Source: Marine-derived streptomycete Streptomyces sundarbansensis (endophytic) from brown alga Fucus sp. (Bejaia, Algeria). Pharm: Antibacterial (MRSA, modest but selective). Ref: I. Djinni, et al, Mar. Drugs, 2013, 11, 124

54

1 Oxygen Heterocycles

O

HO

O

O

O

OH

178 Crispatene Type: 4-Pyrones. C25H34O4 Oil, [α]D = −92.8° (c = 0.12, CHCl3). Source: Sacoglossan Elysia crispata [Syn. Tridachia crispata]. Pharm: Cytotoxic (PS, ED50 = 7.2 μg/mL). Ref: M. B. Ksebati, et al, JOC, 1985, 50, 5637

O

O

H O H

O

179 Crispatone Type: 4-Pyrones. C25H34O5 Cryst. (hexane), mp 164.5–166.5 °C, [α]D = −84.7° (c = 0.03, CHCl3). Source: Sacoglossan Elysia crispata [Syn. Tridachia crispata]. Pharm: Cytotoxic (PS, ED50 = 3.7 μg/mL). Ref: M. B. Ksebati, et al, JOC, 1985, 50, 5637 O O

O

H

O H O

180 Cyercene A Type: 4-Pyrones. C16H22O3 Source: Sacoglossan Cyerce cristallina. Pharm: Ichthyotoxic, tissue regeneration stimulant. Ref: R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569 O

O

O

1.7 4-Pyrones (γ-Pyrones)

55

181 Cyercene B Type: 4-Pyrones. C14H18O3 Source: Sacoglossans Cyerce cristallina and Ercolania funerea. Pharm: Ichthyotoxic. Ref: R. R. Vardaro, et al, Tetrahedron, 1991, 47, 5569; 1992, 48, 9561 O

O

O

182 Deoxyfusapyrone Type: 4-Pyrones. C34H54O8 Oil, [α]D20 = −23.3° (c = 0.23, MeOH). Source: Marinederived fungus Fusarium sp. FH-146 (driftwood, Japan waters). Pharm: Antifungal (Aspergillus clavatus F318a, MIC = 3.12 μg/mL; control Amphotericin B, MIC = 0.15 μg/mL Candida albicans ATCC 2019, MIC > 100 μg/mL; Amphotericin B, MIC = 0.62 μg/mL); antibacterial (Pseudomonas aeruginosa ATCC 15442, MIC = 12.5 μg/mL; control Chloramphenicol, MIC = 1.25 μg/mL; Staphylococcus aureus NBRC 13276, MIC > 100 μg/mL; Chloramphenicol, MIC = 5 μg/mL). Ref: F. Hiramatsu, et al, J. Antibiot., 2006, 59, 704 O

HO

OH

O OH HO

O 26

OH

183 Fusapyrone Type: 4-Pyrones. C34H54O9 Oil, [α]D20 = −22.9° (c = 0.31, MeOH). Source: Marinederived fungus Fusarium sp. FH-146 (driftwood, Japan waters). Pharm: Antifungal (Aspergillus clavatus F318a, MIC = 25 μg/mL; control Amphotericin B, MIC = 0.15 μg/mL Candida albicans ATCC 2019, MIC > 100 μg/mL; Amphotericin B, MIC = 0.62 μg/mL); antibacterial (Pseudomonas aeruginosa ATCC 15442, MIC = 50 μg/mL; control Chloramphenicol, MIC = 1.25 μg/mL; Staphylococcus aureus NBRC 13276, MIC > 100 μg/mL; Chloramphenicol, MIC = 5 μg/mL). Ref: F. Hiramatsu, et al, J. Antibiot., 2006, 59, 704 HO OH

O OH HO OH

O 26

OH

56

1 Oxygen Heterocycles

184 Himeic acid A Type: 4-Pyrones. C22H29NO8 [α]D26 = −15° (c = 0.14, MeOH). Source: Marine-derived fungus Aspergillus sp. Pharm: Ubiquitin-activating enzyme inhibitor. Ref: S. Tsukamoto, et al, BoMCL, 2005, 15, 191 O O

O

O

N H

OH

OH

O O

185 Hyalopyrone 6- (2-Hydroxypropyl)-3-methyl-2- (1-methylpropyl)-4H-pyran-4-one Type: 4-Pyrones. C13H20O3 Pale yellow syrup, [α]D27 = −16.6° (c = 1, MeOH). Source: Marine-derived fungus Ascochyta salicorniae from green alga Ulva sp. (North Sea coast, Germany). Pharm: Protein phosphatase inhibitor (MPtpB, IC50 = 87.8 μmol/L; Cdc25a, PTP1B, VHR, MPtpA and VE-PTP, all five inactive); phytotoxin. Ref: P. Venkatasubbaiah, et al, JNP, 1992, 55, 461│S. F. Seibert, et al, Org. Biomol. Chem., 2006, 4, 2233 O OH O

186 Ilikonapyrone Type: 4-Pyrones. C32H48O7 Cryst., mp 96–98 °C, [α]D = −16° (c = 1.5, CH2Cl2). Source: Pulmonate Onchidium verraculatum. Pharm: Defence allomone of pulmonate Onchidium verruculatum. Ref: C. M. Ireland, et al, JOC, 1984, 49, 559│H. Arimoto, et al, Tet. Lett., 1993, 34, 5781

O OH

O OH

O

OH O

187 Isoplacidene A Type: 4-Pyrones. C16H22O3 Source: Sacoglossan Placida dendritica. Pharm: Ichthyotoxin. Ref: R. R, Vardaro, et al, Tet. Lett., 1992, 33, 2875

1.7 4-Pyrones (γ-Pyrones)

57

O

O

O

188 Isoplacidene B Type: 4-Pyrones. C15H20O3 Source: Sacoglossan Placida dendritica. Pharm: Ichthyotoxin. Ref: R. R, Vardaro, et al, Tet. Lett., 1992, 33, 2875 O

O

O

189 Kalkipyrone Type: 4-Pyrones. C20H28O4 Oil, [α]D20 = +8.2° (c = 0.22, CHCl3). Source: Cyanobacteria Lyngbya majuscula and Tolypothrix sp. (Curacao). Pharm: LD50 (brine shrimp) = 1 μg/mL, (goldfish) = 2 μg/mL. Ref: M. A. Graber, et al, JNP, 1998, 61, 677 O

O

O OH

190 Lehualide B Type: 4-Pyrones. C28H36O4 Oil. Source: Sponge Plakortis sp. Pharm: Cytotoxic. Ref: N. Sata, et al, JNP, 2005, 68, 1400 O O O

O

191 Lehualide D Type: 4-Pyrones. C21H34O4S Oil. Source: Sponge Plakortis sp. Pharm: Cytotoxic. Ref: N. Sata, et al, JNP, 2005, 68, 1400

58

1 Oxygen Heterocycles

O O

O

SH O

192 Marinactinone B Type: 4-Pyrones. C16H26O3 Source: Marine-derived bacterium Marinactinospora thermotolerans (sediment, South China Sea). Pharm: Cytotoxic (HTCLs, moderate); topoisomerase II inhibitor (weak). Ref: F. Wang, et al, J. Antibiot., 2011, 64, 189

O

O

O

193 Marinactinone C Type: 4-Pyrones. C16H26O3 Source: Marine-derived bacterium Marinactinospora thermotolerans (sediment, South China Sea). Pharm: Cytotoxic (HTCLs, moderate). Ref: F. Wang, et al, J. Antibiot., 2011, 64, 189 O

O

O

194 Maurapyrone A Type: 4-Pyrones. C26H36O5 Cryst., mp 110–112 °C. Source: Pulmonate limpet Siphonaria maura. Pharm: Antibacterial (Vibrio anguillarum). Ref: D. C. Manker, et al, JOC, 1986, 51, 814 O

O O 8

O

O

195 Maurapyrone C Type: 4-Pyrones. C25H34O5 Wax. Source: Pulmonate limpet Siphonaria maura. Pharm: Antibacterial (Vibrio anguillarum). Ref: D. C. Manker, et al, JOC, 1986, 51, 814

1.7 4-Pyrones (γ-Pyrones)

59

O

O O 8

O

O

196 Maurapyrone D Type: 4-Pyrones. C25H34O5 Oil. Source: Pulmonate limpet Siphonaria maura. Pharm: Antibacterial (Vibrio anguillarum). Ref: D. C. Manker, et al, JOC, 1986, 51, 814 O

O O 8

O

O

197 5ʹ-Methoxyvermistatin Type: 4-Pyrones. C19H18O7 Cryst., mp 198–199 °C, [α]D20 = −30° (c = 0.1, Me2CO). Source: Mangrove-derived fungus Guignardia sp. 4382 from Mangrove Kandelia candel (South China Sea). Pharm: Cytotoxic (KB, IC50 = 20.0 μg/mL, control Cisplatin, IC50 = 0.56 μg/mL; KBV200, IC50 = 15.1 μg/mL, Cisplatin, IC50 = 0.78 μg/mL). Ref: X. K. Xia, et al, Helv. Chim. Acta, 2007, 90, 1925 O

O

O

O

O O

O

198 Onchitriol I Type: 4-Pyrones. C32H48O7 [α]D = −20.0° (c = 0.01, CH2Cl2). Source: Pulmonate Ohchidium sp. Pharm: Cytotoxic (P388, IC50 ≈ 10 μg/mL; A549, IC50 ≈ 10 μg/mL; HT29, IC50 ≈ 10 μg/mL); antiviral (Herpes simplex virus HSV-1, IC50 = 10 μg/mL; Vesicular stomatitis virus VSV, IC50 = 20 μg/mL); cytotoxic (KB, 1–10 μg/mL, InRt = 90%–98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodríguez, et al, JOC, 1992, 57, 4624│H. Arimoto, et al, Tet. Lett., 1995, 36, 5357

3

O

OH O

13

15

OH

OH

O

O

60

1 Oxygen Heterocycles

199 Onchitriol IA Type: 4-Pyrones. C36H52O9 [α]D = –11.5° (c = 0.02, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%–98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodriguez, et al, JOC, 1992, 57, 4624

O

O O

OH O

O

O O

O

200 Onchitriol IB Type: 4-Pyrones. C37H54O9 [α]D = −19.5° (c = 0.01, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%– 98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodriguez, et al, JOC, 1992, 57, 4624

O

O O

OH O

O

O O

O

201 Onchitriol IC Type: 4-Pyrones. C37H54O9 [α]D = −18.0° (c = 0.1, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%– 98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodriguez, et al, JOC, 1992, 57, 4624

O

O O

OH O

O

O O

O

202 Onchitriol ID Type: 4-Pyrones. C40H58O10 [α]D = −25.2° (c = 0.01, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%– 98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodriguez, et al, JOC, 1992, 57, 4624

1.7 4-Pyrones (γ-Pyrones)

O

O O

O O

O

61

O

O O

O

203 Onchitriol II Type: 4-Pyrones. C32H48O7 [α]D = −33° (c = 0.01, CHCl3). Source: Pulmonate Onchidium sp. Pharm: Cytotoxic (P388, IC50 ≈ 20 μg/mL; A549, IC50 ≈ 20 μg/mL; HT29, IC50 ≈ 20 μg/mL); antiviral (Herpes simplex virus HSV-1, IC50 = 10 μg/mL; Vesicular stomatitis virus VSV, IC50 = 20 μg/mL); cytotoxic (KB, 1–10 μg/mL, InRt = 90%–98%). Ref: J. Rodríguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodríguez, et al, JOC, 1992, 57, 4624│H. Arimoto, et al, Tet. Lett., 1994, 35, 9581 O

O OH

OH

OH

O

O

204 Onchitriol IIA Type: 4-Pyrones. C34H50O8 [α]D = −26.0° (c = 0.1, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%– 98%). Ref: J. Rodriguez, et al, JOC, 1992, 57, 4624│J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089

O

O OH

OH O

O O

O

205 Onchitriol IIB Type: 4-Pyrones. C35H52O8 [α]D = −25.2° (c = 0.01, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%– 98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodriguez, et al, JOC, 1992, 57, 4624

O

O OH

OH O

O O

O

62

1 Oxygen Heterocycles

206 Onchitriol IIC Type: 4-Pyrones. C38H54O10 [α]D = −26.0° (c = 0.01, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%– 98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodriguez, et al, JOC, 1992, 57, 4624

O

O O

O O

O

O

O O

O

207 Onchitriol IID Type: 4-Pyrones. C36H52O9 [α]D = −20.0° (c = 0.1, CH2Cl2). Source: Pulmonate Onchidium sp. (New Caledonia). Pharm: Cytotoxic (KB, 1–10 μg/mL, InRt = 90%– 98%). Ref: J. Rodriguez, et al, Tet. Lett., 1992, 33, 1089│J. Rodriguez, et al, JOC, 1992, 57, 4624

O OH

O O

O

O O O

O

208 Peroniatriol I Type: 4-Pyrones. C32H48O7 [α]D = −12.4° (c = 1.2, CH2Cl2). Source: Pulmonate Peronia peronia. Pharm: Cytotoxic. Ref: J. E. Biskupiak, et al, Tet. Lett., 1985, 26, 4307│ H. Arimoto, et al, Tet. Lett., 1993, 34, 5781

O OH

O OH

O

OH O

209 Peroniatriol II Type: 4-Pyrones. C32H48O7 [α]D = +224.8° (c = 1, CH2Cl2). Source: Pulmonate Peronia peronia. Pharm: Cytotoxic. Ref: J. E. Biskupiak, et al, Tet. Lett., 1985, 26, 4307│ H. Arimoto, et al, Tet. Lett., 1993, 34, 5781

1.7 4-Pyrones (γ-Pyrones)

O

63

O

OH

OH O

OH O

210 Photodeoxytridachione Type: 4-Pyrones. C22H30O3 [α]D25 = +14.4° (c = 0.6, CHCl3). Source: Sacoglossans Elysia timida (Mediterranean Sea) and Placobranchus ocellatus. Pharm: Ichthyotoxin. Ref: C. M. Ireland, et al, Science, 1979, 205, 922│C. M. Ireland, et al, Tetrahedron, 1981, 37, 233 O O

O

211 Pinnamine Type: 4-Pyrones. C13H19NO2 Oil. Source: Bivalve Pinna muricata (Okinawa). Pharm: Toxin; LD50 (mus, acute toxic) = 0.5 μg/mL; highly toxic; LD99 = 0.5 mg/kg (mus). Ref: N. Takada, et al, Tet. Lett., 2000, 41, 6425│H. Kigoshi, et al, Tet. Lett., 2001, 42, 7469│M. Kuramoto, et al, Mar. Drugs, 2004, 2, 39 O

H H N H

O

H

H

212 Placidene A Type: 4-Pyrones. C16H22O3 Source: Sacoglossan Placida dendritica. Pharm: Ichthyotoxin. Ref: R. R, Vardaro, et al, Tet. Lett., 1992, 33, 2875 O

O

O

213 Placidene B Type: 4-Pyrones. C15H20O3 Source: Sacoglossan Placida dendritica. Pharm: Ichthyotoxin. Ref: R. R, Vardaro, et al, Tet. Lett., 1992, 33, 2875

64

1 Oxygen Heterocycles

O

O

O

214 Polyporapyranone A Type: 4-Pyrones. C13H12O4 Source: Two marine-derived fungi Polyporales sp. from green alga Thalassia hemprichii (location unspecified, presumably Thailand). Pharm: Cytotoxic (Vero, moderate and weak). Ref: V. Rukachaisirikul, et al, Tetrahedron, 2013, 69, 6981 O

O

O O

215 Polyporapyranone D Type: 4-Pyrones. C11H7ClO3 Source: Two marine-derived fungi Polyporales sp. from green alga Thalassia hemprichii (location unspecified, presumably Thailand). Pharm: Cytotoxic (Vero, moderate and weak). Ref: V. Rukachaisirikul, et al, Tetrahedron, 2013, 69, 6981 O

HO

O

Cl

216 Tridachiapyrone A Type: 4-Pyrones. C25H34O4 Oil. Source: Sacoglossan Elysia crispata [Syn. Tridachia crispata]. Pharm: Cytotoxic (PS, ED50 = 7.2 μg/mL). Ref: M. B. Ksebati, et al, JOC, 1985, 50, 5637

1.7 4-Pyrones (γ-Pyrones)

65

9 10

14

O

O

O

O

217 Tridachiapyrone B Type: 4-Pyrones. C25H32O5 Oil. Source: Sacoglossan Elysia crispata [Syn. Tridachia crispata]. Pharm: Cytotoxic (PS, ED50 = 6 μg/mL). Ref: M. B. Ksebati, et al, JOC, 1985, 50, 5637 O O 14

O

O

O

218 Tridachiapyrone D Type: 4-Pyrones. C25H34O6 Oil. Source: Sacoglossan Elysia crispata [Syn. Tridachia crispata]. Pharm: Cytotoxic (PS, ED50 = 3.1 μg/mL). Ref: M. B. Ksebati, et al, JOC, 1985, 50, 5637

O

O

O

HO O

O

219 Vermistatin Fijiensin Type: 4-Pyrones. C18H16O6 Cryst., mp 213–214 °C, [α]D20 = −8.5° (c = 0.2, CHCl3). Source: Mangrove-derived fungus Guignardia sp. 4382 from Mangrove Kandelia candel (South China Sea). Pharm: Cytotoxic (EAC and P388, RNA synthesis inhibitors as an elastase inhibitor); Cytotoxic (KB, IC50 = 90.2 μg/mL, control Cisplatin, IC50 = 0.56 μg/mL); phytotoxin (various banana cultivars). Ref: J. Fuska, et al, J. Antibiot., 1986, 39, 1605│X. K. Xia, et al, Helv. Chim. Acta, 2007, 90, 1925

66

1 Oxygen Heterocycles

O

O O

O O

O

220 Yoshinone A Type: 4-Pyrones. C21H32O5 Source: Cyanobacterium Leptolyngbya sp. Pharm: Antiobesity (inhibits differentiation of 3T3-L1 cells into adipocytes without accompanying cytotoxicity, suggesting potential as an anti-obesity lead). Ref: T. Inuzuka, et al, Tet. Lett., 2014, 55, 6711 O O O

O OH

1.8 Spiroketals 221 Antibiotic H 668 Type: Spiroketals. C36H64O12 Amorph. solid, [α]D24 = +48.2° (c = 0.17, MeOH). Source: Marine-derived streptomycete Streptomyces sp. H668. Pharm: Antimalarial (Plasmodium falciparum D6 and W2, IC50 = 0.1–0.2 μg/mL). Ref: M. K. Na, et al, Tet. Lett., 2008, 49, 6282 OH

O O

H

O O

H

H O

OH

O

O

H O

H

OH

H

O

222 Ascochytatin Type: Spiroketals. C20H14O7 Needles (MeOH), mp 227–229 °C (dec), [α]D25 = −153° (c = 0.2, MeOH). Source: Marine-derived fungus Ascochyta sp. NGB4. Pharm: Antibacterial (temperature-sensitive mutant Bacillus subtilis CNM2000, MID = 0.3 μg, stronger than wild-type strain 168, suggesting ascochytatin inhibited function of YycG/YycF-TCS in bacterium); antibacterial (gram-positive bacteria, strongly); antifungal (Candida albicans, strongly); cytotoxic (two mammalian cancer cell lines, IC50 values in lower μmol/L range). Ref: K. Kanoh, et al, J. Antibiot., 2008,

1.8 Spiroketals

67

61, 142│A. M. S. Mayer et al, Comparative Biochemistry and Physiology, Part C 153, 2011, 191 (rev)

OH

HO O

OH O

HO

O

223 Attenol A Type: Spiroketals. C22H38O5 Source: Bivalve Pinna attenuata (China waters). Pharm: Cytotoxic (P388, IC50 = 24 μg/mL). Ref: N. Takada, et al, Chem. Lett., 1999, 1025│K. Suenaga, et al, Org. Lett., 2001, 3, 527

OH O OH

O

OH

224 Azaspirofuran A Type: Spiroketals. C22H21NO7 Pale yellow oil, [α]D20 = −19.7° (c = 0.295, CHCl3). Source: Marine-derived fungi Aspergillus sydowi (sediment, Jiaozhou Bay, China) and Aspergillus fumigatus from fish Mugil cephalus (Katsuura Bay, Japan waters). Pharm: Cytotoxic (MTT assay, A549, IC50 = 10 μmol/L). Ref: K. Mizoue, et al, Eur. Pat. Appl., 1987, EP 216607│T. Yamada, et al, JOC, 2010, 75, 4146│H. Ren, et al, Arch. Pharmacal Res., 2010, 33, 499

O OH O

OO

O N H

O

225 Bistramide A Bistratene A; BST-A Type: Spiroketals. C40H68N2O8 Amorph. solid, [α]D20 = +10° (c = 0.05, CH2Cl2). Source: Ascidians Lissoclinum bistratum and Trididemnum cyclops. Pharm: Cytotoxic (fibroblast cell MRC5CVl and bladder carcinoma cell T-24, IC50 = 0.07 μg/mL); cytotoxic (KB, IC50 = 0.53 μg/mL; P388, IC50 = 0.20 μg/mL; P388/ dox, IC50 = 0.05 μg/mL; B16, IC50 = 0.10 μg/mL; HT29, IC50 = 0.32 μg/mL; NSCLCN6, IC50 = 0.03 μg/mL; control 6-Mercaptopurine: KB, IC50 = 0.55 μg/mL; P388,

68

1 Oxygen Heterocycles

IC50 = 0.70 μg/mL; P388/dox, IC50 = 0.26 μg/mL; B16, IC50 = 0.80 μg/mL; HT29, IC50 = 0.87 μg/mL; NSCLC-N6, IC50 = 0.79 μg/mL); inhibits cell cycle (significant decreases S phase with partial blocks in the G phase). Ref: D. Gouiffes, et al, Tetrahedron 1988, 44, 451│B. M. Degnan, et al, JMC, 1989, 32, 1354│M. P. Foster, et al, JACS, 1992, 114, 1110 (structure revised)│R. Dunkel, et al, Anal. Chem., 1992, 64, 3150│J. -F. Biard, et al, JNP, 1994, 57, 1336 O

O O

H N

N H

OH

O

O

O 39

OH

226 Bistramide B BST-B Type: Spiroketals. C40H70N2O8 [α]D20 = +10° (c = 0.01, CH2Cl2). Source: Ascidian Lissoclinum bistratum (New Caledonia and Fiji). Pharm: Cytotoxic (KB, IC50 = 2.10 μg/mL; P388, IC50 = 0.20 μg/mL; P388/Dox, IC50 = 1.16 μg/mL; B16, IC50 = 1.20 μg/mL; HT29, IC50 = 0.71 μg/mL; NSCLC-N6, IC50 = 0.32 μg/mL; control 6-Mercaptopurine: KB, IC50 = 0.55 μg/mL; P388, IC50 = 0.70 μg/mL; P388/Dox, IC50 = 0.26 μg/mL; B16, IC50 = 0.80 μg/mL; HT29, IC50 = 0.87 μg/mL; NSCLC-N6, IC50 = 0.79 μg/mL); inhibits cell cycle (significant decreases S phase with partial blocks in the G phase); antiparasitic. Ref: J. -F. Biard, et al, JNP, 1994, 57, 1336 OH 4

H N

O

2

O

O

OH

O

O

34 39

HN

O

227 Bistramide C BST-C Type: Spiroketals. C40H66N2O8 Amorph. solid, [α]D20 = +10° (c = 0.05, CH2Cl2). Source: Ascidian Lissoclinum bistratum (New Caledonia and Fiji). Pharm: Cytotoxic (KB, IC50 = 0.65 μg/mL; P388, IC50 = 0.02 μg/mL; P388/Dox, IC50 = 0.05 μg/mL; B16, IC50 = 0.06 μg/mL; HT29, IC50 = 0.50 μg/mL; NSCLC-N6, IC50 = 0.05 μg/mL; control

1.8 Spiroketals

69

6-Mercaptopurine: KB, IC50 = 0.55 μg/mL; P388, IC50 = 0.70 μg/mL; P388/Dox, IC50 = 0.26 μg/mL; B16, IC50 = 0.80 μg/mL; HT29, IC50 = 0.87 μg/mL; NSCLC-N6, IC50 = 0.79 μg/mL); inhibits cell cycle (significant decreases S phase with partial blocks in the G phase); antiparasitic; antiproliferative. Ref: J. -F. Biard, et al, JNP, 1994, 57, 1336│G. Zuber, et al, Org. Lett., 2005, 7, 5269 OH 4

H N

O

2

O

O

O

HN

O

O

34

O

39

228 Bistramide D BST-D Type: Spiroketals. C40H77N2O8 Amorph. solid, [α]D20 = +8° (c = 0.04, CH2Cl2). Source: Ascidians Lissoclinum bistratum (New Caledonia and Fiji) and Trididemnum cyclops. Pharm: Cytotoxic (KB, IC50 = 10.0 μg/mL; P388, IC50 = 0.36 μg/mL; P388/ Dox, IC50 = 5.82 μg/mL; B16, IC50 = 0.10 μg/mL; HT29, IC50 = 2.76 μg/mL; NSCLC-N6, IC50 = 3.43 μg/mL; control 6-Mercaptopurine: KB, IC50 = 0.55 μg/mL; P388, IC50 = 0.70 μg/mL; P388/dox, IC50 = 0.26 μg/mL; B16, IC50 = 0.80 μg/mL; HT29, IC50 = 0.87 μg/mL; NSCLC-N6, IC50 = 0.79 μg/mL); inhibits cell cycle (significant decreases S phase with partial blocks in the G phase); antiparasitic. Ref: J. -F. Biard, et al, JNP, 1994, 57, 1336│C. Bauder, et al, Org. Biomol. Chem., 2006, 4, 1860 OH 4

H N

O

2

OH

O

OH

O

O

34 39

HN

O

229 Bistramide K Type: Spiroketals. C40H70N2O8 Amorph. solid, [α]D20 = +20° (c = 0.02, CH2Cl2). Source: Ascidian Lissoclinum bistratum (New Caledonia and Fiji). Pharm: Cytotoxic (KB, IC50 > 10.0 μg/mL; P388, IC50 = 0.57 μg/mL; P388/Dox, IC50 > 10.0 μg/mL; B16, IC50 = 1.90 μg/mL; HT29, IC50 = 5.60 μg/mL; NSCLC-N6, IC50 = 3.23 μg/mL; control 6-Mercaptopurine: KB, IC50 = 0.55 μg/mL; P388, IC50 = 0.70 μg/mL; P388/Dox, IC50 = 0.26 μg/mL; B16, IC50 = 0.80 μg/mL; HT29, IC50 = 0.87 μg/mL; NSCLC-N6,

70

1 Oxygen Heterocycles

IC50 = 0.79 μg/mL); inhibits cell cycle (completely blocks NSCLC-N6 cells in G phase after 48 h of growth); antiparasitic. Ref: J. -F. Biard, et al, JNP, 1994, 57, 1336 OH

H N OH

OH

OH

O

O

HN

O O

39

230 Bistratene B Type: Spiroketals. C42H70N2O9 Source: Ascidian Lissoclinum bistratum Pharm: Cytotoxic (MRC5CVl and T-24, IC50 = 0.09 μg/mL). Ref: B. M. Degnan, et al, JMC, 1989, 32, 1354│M. P. Foster, et al, JACS, 1992, 114, 1110 (struc. revised)│R. Dunkel, et al, Anal. Chem., 1992, 64, 3150

4

OH

H N

O

2

O

O

O

O

HN

O O

34

O

39

231 Didemnaketal A Type: Spiroketals. C44H72O14 Oil, [α]D = −11.0° (c = 0.8, CHCl3). Source: Ascidian Didemnum sp. (Palau, Oceania). Pharm: HIV-1 protease inhibitor (IC50 = 2 μg/mL). Ref: B. C. M. Potts, et al, JACS, 1991, 113, 6321│C. E. Salomon,et al, Org. Lett., 2002, 4, 1699

O

O O

O

O

O

O O

O H

O

O O

H

HO O

1.8 Spiroketals

71

232 Didemnaketal B Type: Spiroketals. C52H86O15 Oil. Source: Ascidian Didemnum sp. (Palau, Oceania). Pharm: HIV-1 protease inhibitor (IC50 = 10 μg/mL). Ref: B. C. M. Potts, et al, JACS, 1991, 113, 6321│C. E. Salomon,et al, Org. Lett., 2002, 4, 1699

O

O O

O

O

O

O O

O

O

O

H

O

O O

H HO

233 Gymnastatin A Type: Spiroketals. C23H31Cl2NO4 Powder, mp 74.2–76.0 °C, [α]D = −3.8° (c = 0.73, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica. Pharm: Cytotoxic (P388, ED50 = 18 ng/mL). Ref: Numata, et al, Tet. Lett., 1997, 38, 5675│T. Amagata, et al, JCS Perkin I, 1998, 3585│M. K. Gurjar, et al, Heterocycles, 2000, 53, 143 O Cl

Cl

O

O N H

OH

234 Gymnastatin B Type: Spiroketals. C24H35Cl2NO5 Powder, mp 73.5–77.5 °C, [α]D = −122.1° (c = 0.3, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica. Pharm: Cytotoxic (P388, ED50 = 108 ng/mL). Ref: T. Amagata, et al, JCS Perkin I, 1998, 3585 Cl O

O 9 10

O

7 6

Cl

2

OH

H N O

72

1 Oxygen Heterocycles

235 Gymnastatin C Type: Spiroketals. C24H37Cl2NO6 Powder, mp 104.7–107.5 °C, [α]D = −101.2° (c = 0.1, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica. Pharm: Cytotoxic (P388, ED50 = 106 ng/mL). Ref: T. Amagata, et al, JCS Perkin I, 1998, 3585 Cl

OH O

O 9 10

O Cl

7 6

2

H N

OH

O

236 Gymnastatin D Type: Spiroketals. C23H34ClNO5 Amorph. powder, mp 86.4–88.2 °C, [α]D = −8.9° (c = 0.45, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica. Pharm: Cytotoxic (P388, ED50 = 10.5 μg/mL). Ref: T. Amagata, et al, JCS Perkin I, 1998, 3585 O OH

O 2

HO

H N

Cl

O

237 Gymnastatin E Type: Spiroketals. C23H34ClNO5 Amorph. powder, mp 87.3–88 °C, [α]D = −8.5° (c = 0.52, CHCl3). Source: Marine-derived fungus Gymnascella dankaliensis from sponge Halichondria japonica. Pharm: Cytotoxic (P388, ED50 = 10.8 μg/mL). Ref: T. Amagata, et al, JCS Perkin I, 1998, 3585 Cl OH

O 2

HO O

H N O

238 Gymnastatin I Type: Spiroketals. C23H31Br2NO4 Source: Marine-derived fungus Gymnascella dankaliensis. Pharm: Cytotoxic (panel of 39 hmn cancer cell lines); cytotoxic (P388, potent). Ref: T. Amagata, et al, Heterocycles, 2010, 81, 897

1.8 Spiroketals

73

O

Br

Br O O N H OH

239 Gymnastatin J Type: Spiroketals. C24H35Br2NO6 Source: Marine-derived fungus Gymnascella dankaliensis. Pharm: Cytotoxic (panel of 39 hmn cancer cell lines); cytotoxic (P388, potent). Ref: T. Amagata, et al, Heterocycles, 2010, 81, 897 O

Br

Br

HO O OH

O N H O

240 Gymnastatin K Type: Spiroketals. C24H37Br2NO6 Source: Marine-derived fungus Gymnascella dankaliensis. Pharm: Cytotoxic (P388, potent). Ref: T. Amagata, et al, Heterocycles, 2010, 81, 897 O

Br

Br

HO O O N H

OH

O

241 Marinisporolide A Type: Spiroketals. C38H58O10 Amorph. yellow powder. Source: Marine-derived actinomycete Marinispora sp. CNQ-140 (sediment, culture, La Jolla, California). Pharm: Antifungal (yeast Candida albicans, modest). Ref: H. C. Kwon, et al, JOC, 2009, 74, 675 H

O 8

4

OH

10

O

O OH

OH

OH

OH

O

H

OH

74

1 Oxygen Heterocycles

242 30-Methyloscillatoxin D Type: Spiroketals. C32H44O8 Cryst. (MeOH), mp 166 °C. Source: Cyanobacterium Lyngbya majuscula (deepwater); a mixed collection of Schizothrix calcicola and Oscillatoria nigroviridis. Pharm: Antileukemia; toxin. Ref: M. Entzeroth, et al, JOC, 1985, 50, 1255│H, -J, Knölker, et al, Tet. Lett., 1995, 36, 5339│H. Toshima, et al, Tet. Lett., 1995, 36, 3373

O O O

O

O

O

O OH

243 Oscillatoxin D Type: Spiroketals. C31H42O8 Gum. Source: Cyanobacteria Schizothrix calcicola and Oscillatoria nigroviridis (mixture). Pharm: Antileukemia; toxin. Ref: M. Entzeroth, et al, JOC, 1985, 50, 1255│H, -J, Knölker, et al, Tet. Lett., 1995, 36, 5339│ H. Toshima, et al, Tet. Lett., 1995, 36, 3373

O O O O

O

O OH

O

244 39-Oxobistramide K Type: Spiroketals. C40H68N2O8 Amorph. powder, [α]D25 = −72° (c = 0.05, MeOH). Source: Ascidian Trididemnum cyclops (Madagascar). Pharm: Cytotoxic (A2780, IC50 = 0.34 μmol/L). Ref: B. T. Murphy, et al, JNP, 2009, 72, 1338 OH H N

39

O

OH

OH O

O O

HN

O

1.8 Spiroketals

75

245 Paecilospirone Type: Spiroketals. C32H44O5 [α]D25 = +202.5° (c = 0.37, MeOH). Source: Marinederived fungus Paecilomyces sp. (from a coral reef, Yap, Federated States of Micronesia). Pharm: Microtubule assemblage inhibitor. Ref: M. Namikoshi, et al, Chem. Lett., 2000, 308│M. Namikoshi, et al, CPB, 2000, 48, 1452

OH

HO

O

O

O

246 Penisporolide A Type: Spiroketals. C18H30O5 Pale yellow oil, [α]D20 = +37° (c = 0.5, MeOH). Source: Mangrove-derived fungus Penicillium sp. HKI GT20022605 from mangrove Kandelia candel (China waters). Pharm: Xanthine oxidase inhibitor (mild); 3α-Hydroxysteroid dehydrogenase inhibitor (mild). Ref: X. Li, et al, J. Antibiot., 2007, 60, 191 H O O O

O

H OH

247 Penisporolide B Type: Spiroketals. C17H26O5 Pale yellow oil, [α]D20 = +81° (c = 1, MeOH). Source: Mangrove-derived fungus Penicillium sp. HKI GT20022605 from mangrove Kandelia candel (China waters). Pharm: Xanthine oxidase inhibitor (mild); 3α-Hydroxysteroid dehydrogenase inhibitor (mild). Ref: X. Li, et al, J. Antibiot., 2007, 60, 191 H O O O

O

H O

248 Prunolide A Type: Spiroketals. C34H14Br8O9 Yellow plates (DMSO), mp 212–214 °C, [α]D25 = 0° (c = 0.5, MeOH). Source: Ascidian Synoicum prunum (Australia). Pharm: Cytotoxic (inhibits growth of HeLa at 25 μmol/L, weak). Ref: A. R. Carroll, et al, JOC, 1999, 64, 2680

76

1 Oxygen Heterocycles

OH Br

OH

Br Br

Br

O O

O O

O Br

Br Br Br

HO

OH

249 Prunolide B Type: Spiroketals. C34H16Br6O9 Yellow gum, [α]D25 = 0° (c = 0.1, MeOH). Source: Ascidian Synoicum prunum (Australia). Pharm: Cytotoxic (weak). Ref: A. R. Carroll, et al, JOC, 1999, 64, 2680 OH

OH Br Br

Br

Br

O O

O O

O

HO

Br Br

OH

250 Prunolide C Type: Spiroketals. C34H22O9 Yellow gum, [α]D25 = 0° (c = 0.4, MeOH). Source: Ascidian Synoicum prunum (Australia). Pharm: Cytotoxic (inhibits growth of HeLa at 15 μmol/L, weak). Ref: A. R. Carroll, et al, JOC, 1999, 64, 2680 OH

OH

O O

O

O

O

HO

OH

1.8 Spiroketals

77

251 Spirastrellolide A Type: Spiroketals. C52H81ClO17 Oil (Me ester), [α]D25 = +27° (c = 0.16, CH2Cl2) (Me ester). Source: Sponge Spirastrella coccinea, sponge Epipolasis sp. (Nagannu I., Japan, East China Sea). Pharm: Antimitotic; protein phosphatase inhibitor (selective); cytotoxic (free acids are more active than their methyl esters). Ref: D. E. Williams, et al, JACS, 2003, 125, 5296│D. E. Williams, et al, Org. Lett., 2004, 6, 2607│M. Suzuki, et al, JNP, 2012, 75, 1192 OH O

O

46

O

O O

O

O Cl

O 4

O

HO OH

8

H O O

HO

OH O

15

16

252 Spirastrellolide B Spirostrellolide E Type: Spiroketals. C52H84O17 Oil (Me ester), [α]D25 = +44.7° (c = 0.5, MeOH) (Me ester). Source: Sponge Spirastrella coccinea, sponge Epipolasis sp. (Nagannu I., Japan, East China Sea). Pharm: Cytotoxic (free acids are more active than their methyl esters). Ref: K. Warabi, et al, JACS, 2007, 129, 508│ M. Suzuki, et al, JNP, 2012, 75, 1192 OH O

O

46

O

O O

O

O

O 4

O

HO OH

8

H O O

HO

OH O

15

16

78

1 Oxygen Heterocycles

253 Spirastrellolide D Type: Spiroketals. C52H80Cl2O17 Oil (Me ester), [α]D25 = +45.9° (c = 0.5, MeOH) (Me ester). Source: Sponge Spirastrella coccinea. Pharm: Inhibits premature mitosis (IC50 = 0.4–0.7 μmol/L, MMOA: protein phosphatase 2A inhibition). Ref: D. E. Williams, et al, JOC, 2007, 72, 9842 OH O

O

46

O

O O

O Cl

O Cl

O 4

O

HO OH

8

H O O

HO

OH O

15

16

254 Spirastrellolide E Type: Spiroketals. C52H82O17 Oil (Me ester), [α]D25 = +47.4° (c = 0.5, MeOH) (Me ester). Source: Sponge Spirastrella coccinea. Pharm: Inhibits premature mitosis (IC50 = 0.4–0.7 μmol/L, MMOA: protein phosphatase 2A inhibition). Ref: D. E. Williams, et al, JOC, 2007, 72, 9842 OH O

O

46

O

O O

O

O

O 4

O

HO OH

H

H O O

OH O

OH 15

16

255 Spiroxin A Type: Spiroketals. C20H9ClO8 [α]D25 = −644° (c = 0.18, MeOH). Source: An unidentified marine-derived fungus LL-37H248 from an unidentified soft coral. Pharm: Cytotoxic (25 diverse cell lines, IC50 = 0.09 μg/mL); antineoplastic (in vivo ovarian carcinoma in nude mice, after 21 days, 59% growth inhibition).

1.8 Spiroketals

79

Ref: L. A. McDonald, et al, Tet. Lett., 1999, 40, 2489│T. Wang, et al, Can. J. Chem., 2001, 79, 1786│K. Krohn, Prog. Chem. Org. Nat. Prod., 2003, 85, 1-49 (rev)

O OH

O

1

Cl 7

O

O O

1'

7' 8'

OH

O

256 Spiroxin B Antibiotic F 12517 Type: Spiroketals. C20H8Cl2O8 [α]D25 = −475° (c = 0.21, MeOH). Source: An unidentified marine-derived fungus LL-37H248 from an unidentified soft coral (orange, Vancouver Island). Pharm: DNA cleaving agent (antineoplastic, antibiotics); cytotoxic (mus xenograft model, hmn ovarian carcinoma). Ref: L. A. McDonald, et al, Tet. Lett., 1999, 40. 2489│K. Krohn, Prog. Chem. Org. Nat. Prod., 2003, 85, 1-49 (rev)

O OH

O

1

Cl 7

O

O

7'

Cl

1'

O

8'

OH

O

257 Spiroxin C Type: Spiroketals. C20H10O7 [α]D25 = −706° (c = 0.26, MeOH). Source: An unidentified marine-derived fungus LL-37H248 from an unidentified soft coral (orange, Vancouver Island). Pharm: DNA cleaving agent (antineoplastic, antibiotics); cytotoxic (mus xenograft model, hmn ovarian carcinoma). Ref: L. A. McDonald, et al, Tet. Lett., 1999, 40, 2489│K. Krohn, Prog. Chem. Org. Nat. Prod., 2003, 85, 1-49 (rev)

80

1 Oxygen Heterocycles

O OH

O

1 7

O

O O 1'

7' 8'

O

258 Spiroxin D Type: Spiroketals. C20H12O7 Source: An unidentified marine-derived fungus LL-37H248 from an unidentified soft coral (orange, Vancouver Island). Pharm: DNA cleaving agent (antineoplastic, antibiotics); cytotoxic (mus xenograft model, hmn ovarian carcinoma). Ref: L. A. McDonald, et al, Tet. Lett., 1999, 40, 2489│K. Krohn, Prog. Chem. Org. Nat. Prod., 2003, 85, 1-49 (rev) OH OH

O

1 7

O

O O

1'

7' 8'

O

259 Spiroxin E Type: Spiroketals. C20H10Cl2O8 Source: An unidentified marine-derived fungus LL-37H248 from an unidentified soft coral (orange, Vancouver Island). Pharm: DNA cleaving agent (antineoplastic, antibiotics); cytotoxic (mus xenograft model, hmn ovarian carcinoma). Ref: L. A. McDonald, et al, Tet. Lett., 1999, 40, 2489│K. Krohn, Prog. Chem. Org. Nat. Prod., 2003, 85, 1-49 (rev) O OH

O

1

Cl 7

O

O

7'

Cl

1' 8'

OH

OH

O

2 Aromatic Metabolites 2.1 Simple Benzene Derivatives 260 2,4-Dibromo-6-chlorophenol Type: Phenol derivatives. C6H3Br2ClO mp 78–79 °C. Source: Marine-derived bacterium Pseudoalteromonas luteoviolacea from brown alga Padina australis (surface, Hawaii). Pharm: Antibacterial (MRSA and Burkholderia cepacia). Ref: Z. Jiang, et al, Nat. Prod. Lett., 2000, 14, 435 OH Br

Cl

Br

261 2,6-Dibromophenol Type: Phenol derivatives. C6H4Br2O Needles (H2O), mp 56–57 °C, bp21mmHg 162 °C, pKa = 6.67 (25 °C), sublime. Source: Hemichordate acorn worm Balanoglossus biminiensis, phoronid tubeworm Phoronopsis viridis, occurs widespread in marine algae, fishes, molluscs and crustaceans, such as green alga Ulva lactuca. Pharm: Odour; flavour component (marine fish, molluscs and crustaceans). Ref: R. B. Ashworth, et al, Science, 1967, 155, 1588│Y. M. Sheikh, et al, Experientia, 1975, 31, 265│ J. Buckingham (executive editor), Dictionary of Natural Products, Vol 2, pp1416, Chapman & Hall, 1994│F. B. Whitfield, et al, J. Agric. Food Chem., 1997, 45, 4398; 1999, 47, 2367; 4756 OH Br

Br

262 2,4-Dibromophenol Type: Phenol derivatives. C6H4Br2O mp 40 °C, bp11mmHg 154 °C. Source: Hemichordate acorn worms Balanoglossus cornosus and Ptychodera sp., marine algae, e.g. Grateloupia elliptica, and occurs in molluscs and crustaceans. Pharm: LD50 (mus, orl) = 282 mg/kg. Ref: T. Higa, et al, Comp. Biochem. Physiol., B, 1980, 65, 525│F. B. Whitfield, et al, J. Agric. Food Chem., 1997, 45, 4398; 1999, 47, 2367 OH Br

Br

https://doi.org/10.1515/9783110655810-002

82

2 Aromatic Metabolites

263 2,4-Dibromophenol Type: Phenol derivatives. C6H4Br2O Source: Red alga Grateloupia elliptica. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Bacillus stearothermophilus, IC50 = 230.3 μmol/L; Saccharomyces cerevisiae, IC50 = 110.4 μmol/L; rat intestinal maltase, IC50 = 4.8 mmol/L; rat instestinal sucrase, IC50 = 3.6 mmol/L). Ref: K. Y. Kim, et al, Phytochemistry, 2008, 69, 2820 Br HO

Br

264 4-(1,1-Dimethyl-2-propenyl)-2-(3-methyl-2-butenyl)phenol Type: Phenol derivatives. C16H22O Oil. Source: Brown algae Sporochnus comosus (Shaw I., Queensland, Australia), Perithalia caudata, Perithalia capillaris and Sporochnus pedunculatus. Pharm: Cytotoxic (SF268, GI50 = 39 μmol/L; MCF7, GI50 = 27 μmol/L; H460, GI50 = 37 μmol/L; HT29, GI50 = 57 μmol/L; CHO-K1, GI50 = 17 μmol/L); antibacterial; antifungal. Ref: A. Blackman,et al, Aust. J. Chem., 1979, 32,2783│ L. S. Gunasekera, et al, J. Int. J. Pharmacogn., 1995, 33, 253│C.E.Sansom, et al, JNP, 2007, 70, 2042│S. P. B. Ovenden, et al, JNP, 2011, 74, 739 OH

265 2,4-Diprenylphenol Type: Phenol derivatives. C16H22O Oil. Source: Brown alga Encyothalia cliftonii (Australia). Pharm: Antifeedant. Ref: V. Roussis, et al, Phytochemistry, 1993, 34, 107 OH

266 2,4,6-Tribromophenol Bromol; Velcide Type: Phenol derivatives. C6H3Br3O Needles (EtOH), prisms (C6H6), mp 87–89 °C, subl. 95–96 °C Source: Phoronid tubeworm Phoronopsis viridis, hemichordate acorn worm Ptychodera flava laysanica, green alga Ulva lactate, red alga Grateloupia elliptica. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Bacillus stearothermophilus, IC50 = 103.3 μmol/L, Saccharomyces cerevisiae, IC50 = 60.3 μmol/L, rat intestinal maltase, IC50 = 5.0 mmol/L, rat instestinal sucrase,

2.1 Simple Benzene Derivatives

83

IC50 = 4.2 mmol/L) (Kim, 2008); antiseptic (strong); irritant; LD50 (rat, orl) = 2000 mg/kg. Ref: Y. M. Sheikh, et al, Experientia, 1975, 31, 265│C. Flodin, et al, Phytochemistry, 1999, 51, 249; 2000, 53, 77│K. Y. Kim, et al, Phytochemistry, 2008, 69, 2820 OH Br

Br

Br

267 Citrinin H2 Type: m-Benzenediol derivatives. C12H16O4 Needles (CHCl3), mp 139.5–140 °C, mp 131–133 °C. Source: Marine-derived fungus Penicillium sp. MFA446 from green alga Ulva pertusa (Korea waters). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: M. Hirota, et al, Biosci. Biotechnol. Biochem., 2002, 66, 206│D. Zhang, et al, J. Microbiol. Biotechnol., 2007, 17, 865 HO O OH

O

268 5,6-Dibromocatechol 4,5-Dibromo-1,3-benzenediol Type: m-Benzenediol derivatives. C6H4Br2O2 Source: Sponge Dysidea sp. (Indo-Pacific). Pharm: Inosine monophosphate dehydrogenase (IMPDH) inhibitor; guanosine monophosphate synthetase inhibitor; 15-lipoxygenase inhibitor. Ref: X. Fu, et al, JNP, 1995, 58, 1384 OH Br

Br

OH

269 2,4-Dihydroxy-3,5,6-trimethylbenzaldehyde Type: m-Benzenediol derivatives. C10H12O3 Source: Deep-sea fungus Aspergillus sydowi YH11-2 (Guam, depth of 1000 m, E144°43′ N13°26′). Pharm: Cytotoxic (P388, IC50 = 0.59 μmol/L, control CDDP, IC50 = 0.039 μmol/L). Ref: L. Tian, et al, Arch. Pharm. Res,. 2007, 30, 1051 H O HO

OH

84

2 Aromatic Metabolites

270 Phenol A acid Type: m-Benzenediol derivatives. C12H16O5 Source: Deep-sea fungus Aspergillus sp. SCSIOW3. Pharm: Anti-Aβ peptide aggregation inhibition (Aβ42 assembling activity, 100 μmol/L, 40.3%–72.3%). Ref: H. Liu, et al, Chin. J. Mar. Drugs, 2014, 33, 71 (in Chinese) OH

HO

OH HO

O

271 Acremonin A 7-Isopropenylbicyclo[4.2.0]octa-1,3,5-triene-2,5-diol Type: p-Benzenediol derivatives. C11H12O2 Yellow-brown viscous oil, [α]D23 = +93° (c = 1.4, Me2CO). Source: Marinederived fungus Acremonium sp. Pharm: Antioxidant (thiobarbituric acid reactive substance (TBARS) assay, 25.0 μg/mL, InRt = 85.5%). Ref: A. Abdel-Lateff, et al, JNP, 2002, 65, 1605│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) OH

OH

272 Acremonin A 5-β-glucopyranoside 7-Isopropenylbicyclo[4.2.0]octa-1,3,5-triene-2,5-diol-5-β-glucopyranoside Type: p-Benzenediol derivatives. C17H22O7 Amorph. powder, [α]D23 = +4.3° (c = 2, Me2CO). Source: Marine-derived fungus Acremonium sp. Pharm: Antioxidant (thiobarbituric acid reactive substance (TBARS) assay, 25.0 μg/mL, InRt = 85.5%). Ref: A. Abdel-Lateff, et al, JNP, 2002, 65, 1605│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) OH

OO

HO OH OH

OH

2.1 Simple Benzene Derivatives

85

273 Comosone A Type: p-Benzenediol derivatives. C16H24O2 Source: Brown alga Sporochnus comosus (Shaw I., Queensland, Australia). Pharm: Cytotoxic (SF268, GI50 = 13 μmol/L; MCF7, GI50 = 14 μmol/L; H460, GI50 = 19 μmol/L; HT29, GI50 = 19 μmol/L; CHO-K1, GI50 = 17 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 739 O

OH

274 Comosusol A Type: p-Benzenediol derivatives. C16H22O3 Source: Brown alga Sporochnus comosus (Shaw I., Queensland, Australia). Pharm: Cytotoxic (SF268, GI50 = 55 μmol/L; MCF7, GI50 = 52 μmol/L; H460, GI50 = 55 μmol/L; HT29, GI50 = 53 μmol/L; CHO-K1, GI50 = 57 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 739 OH

OH OH

275 Comosusol B Type: p-Benzenediol derivatives. C16H22O3 Source: Brown alga Sporochnus comosus (Shaw I., Queensland, Australia). Pharm: Cytotoxic (SF268, GI50 = 5 μmol/L; MCF7, GI50 = 6 μmol/L; H460, GI50 = 6 μmol/L; HT29, GI50 = 6 μmol/L; CHO-K1, GI50 = 6 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 739 OH

OH

OH

276 Comosusol C Type: p-Benzenediol derivatives. C16H22O2 Source: Brown alga Sporochnus comosus (Shaw I., Queensland, Australia). Pharm: Cytotoxic (SF268, GI50 = 35 μmol/L; MCF7, GI50 = 25 μmol/L; H460, GI50 = 29 μmol/L; HT29, GI50 = 43 μmol/L; CHO-K1, GI50 = 27 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 739

86

2 Aromatic Metabolites

OH

OH

277 Comosusol D Type: p-Benzenediol derivatives. C16H24O5 Source: Brown alga Sporochnus comosus (Shaw I., Queensland, Australia). Pharm: Cytotoxic (SF268, GI50 = 59 μmol/L; MCF7, GI50 = 46 μmol/L; H460, GI50 = 54 μmol/L; HT29, GI50 = 51 μmol/L; CHO-K1, GI50 = 63 μmol/L). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 739 OH

OH OH

OH

OH

278 Geroquinol Type: p-Benzenediol derivatives. C16H22O2 Oil. Source: Ascidians Aplidium sp. (Spain) and Aplidium savignyi. Pharm: Cytotoxic (P388, IC50 = 0.2 μg/mL; A549, IC50 = 1 μg/mL; HT29, IC50 = 1 μg/mL; MEL28, IC50 = 1 μg/mL); radioprotectant; antioxidant; contact allergen. Ref: A. Rueda, et al, Nat. Prod. Lett., 1998, 11, 127│ M. Aknin, et al, J. Agric. Food Chem., 1999, 47, 4175 OH

OH

279 2-(7-Hydroxy-3,7-dimethyl-2-octenyl)-1,4-benzenediol Type: p-Benzenediol derivatives. C16H24O3 Oil. Source: Ascidian Aplidium sp. (Spain). Pharm: Cytotoxic (P388, IC50 = 1.2 μg/mL; A549, IC50 = 5 μg/mL; HT29, IC50 = 2 μg/mL; MEL28, IC50 = 2 μg/mL). Ref: A. Rueda, et al, Nat. Prod. Lett., 1998, 11, 127 OH

OH

OH

2.1 Simple Benzene Derivatives

87

280 2-(3-Hydroxy-3,7-dimethyl-6-octenyl)-1,4-benzenediol Type: p-Benzenediol derivatives. C16H24O3 Oil. Source: Protochordate Amaroucium multiplicatum (marine-derived) from ascidian Aplidium savignyi. Pharm: Cytotoxic (significant); antioxidant. Ref: A. Sato, et al, JNP, 1989, 52, 975│M. Aknin, et al, J. Agric. Food Chem., 1999, 47, 4175 OH

OH

OH

281 Mediterraneol A Type: p-Benzenediol derivatives. C27H36O5 Source: Brown alga Cystoseira mediterranea. Pharm: Cytotoxic (fertilized sea urchin eggs, mitotic cell division inhibitor). Ref: C. Francisco, et al, Tet. Lett., 1985, 26, 2629│C. Francisco, et al, JOC, 1986, 51, 1115 O

OH

OH 7

H

OH

OH

282 2-(Methoxymethyl)-1,4-benzenediol Type: p-Benzenediol derivatives. C8H10O3 Amorph. powder. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 58.9 μmol/L; Molt4, IC50 = 86.2 μmol/L; A549, IC50 > 100 μmol/L; Bel7402, IC50 > 100 μmol/L); antioxidant (DPPH scavenger, IC50 = 9.8 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH O

OH

283 2-Pentaprenyl-1,4-benzenediol Type: p-Benzenediol derivatives. C31H46O2 Source: Sponges Ircinia sp. (New Caledonia) and Spongia sp. (Australia). Pharm: Tyrosine protein kinase (TPK) inhibitor; HIVintegrase inhibitor; binds to neuropeptide Y receptor Ref: D. Lumsdon, et al, Aust. J. Chem., 1992, 45, 1321│G. Bifulco, et al, JNP, 1995, 58, 1444

88

2 Aromatic Metabolites

HO

OH

284 Phloroglucinol 1,3,5-Benzenetriol Type: m-Benzenetriol derivatives. C6H6O3 Source: Brown algae Ecklonia stolonifera, Eisenia bicyclis and Ecklonia maxima. Pharm: Hypoglycemic (aldose reductase inhibitor) (rat lens aldose reductase in vitro assay, IC50 = 72.54 μmol/L) (Jung, 2008); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 141.18 μmol/L) (Moon, 2011); hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 55.48 μmol/L) (Moon, 2011);hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 1991 μmol/L, control Acarbose, IC50 = 1013 μmol/L) (Rengasamy, 2013); antioxidant (DPPH scavenger, EC50 = 0.128 μmol/L, AAI (antioxidant activity index = final DPPH concentration/EC50) = 390, control Ascorbic acid, EC50 = 0.011 μmol/L, AAI = 4356) (Rengasamy, 2013). Ref: H. A. Jung, et al, Fish. Sci., 2008, 74, 1363│H. E. Moon, et al, Biosci. Biotechnol. Biochem., 2011, 75, 1472│K. R. Rengasamy, et al, Food Chem., 2013, 141, 1412 OH

HO

OH

285 BDDE Bis (2,3-dibromo-4,5-dihydroxybenzyl) ether Type: Benzyl alcohols. C14H10Br4O5 Pale yellow solid. Source: Red algae Odonthalia corymbifera, Polyopes lancifolia, Rhodomela spp. and Symphyocladia latiuscula. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Saccharomyces cerevisiae, IC50 = 0.098 μmol/L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Bacillus stearothermophilus, IC50 = 0.12 μmol/L; Saccharomyces cerevisiae, IC50 = 0.098 μmol/L; rat intestinal maltase, IC50 = 1.20 mmol/L; rat intestinal sucrase, IC50 = 1.00 mmol/L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 0.03 μmol/L); hypoglycemic

2.1 Simple Benzene Derivatives

89

(sucrase inhibitor) (in vitro assay, IC50 = 2.4 mmol/L); hypoglycemic (maltase inhibitor) (in vitro assay, IC50 = 3.2 mmol/L); α-glucosidase inhibitor (IC50 = 25 μmol/L). Ref: H. Kurihara, et al, JNP, 1999, 62, 882│H. Kurihara, et al, Fish. Sci. 1999, 65, 300│K. Y. Kim, et al, J. Food Sci. 2010, 75, H145│Y. Sharifuddin, et al, Mar. Drugs, 2015, 13, 5447 (rev) HO

OH

O

HO

OH

Br

Br Br

Br

286 Bis(2,3-dibromo-4,5-dihydroxybenzyl)ether Type: Benzyl alcohols. C14H10Br4O5 Source: Red alga Rhodomela confervoides. Pharm: Hypoglycemic (PTP1B inhibitor) (PTP1B and hypoglycaemic effect in streptozotocininduced diabetic Wistar rats, IC50 = 1.5 μmol/L). Ref: D. Shi, et al, Chin. Sci. Bull., 2008, 53, 2476 Br

Br Br

Br

O HO

OH OH

OH

287 Bis(2,3,6-tribromo-4,5-dihydroxybenzyl)ether 4,4ʹ-[Oxybis(methylene)]bis[3,5,6-tribromo-1,2-benzenediol] Type: Benzyl alcohols. C14H8Br6O5 Fine needles (C6H6/Me2CO), mp 177–178 °C. Source: Red alga Symphyocladia latiuscula. Pharm: Hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 4.3 μmol/L); antifungal. Ref: K. Kurata, et al, Phytochemistry, 1980, 19, 141│X. Liu, et al, Chin. J. Oceanol. Limnol.,2011, 29, 686 Br

Br Br

Br

O

HO

Br OH

Br

OH OH

288 3-Chloro-4,5-dihydroxybenzyl alcohol Type: Benzyl alcohols. C7H7ClO3 Source: Marine-derived fungus Aspergillus parasiticus Pharm: Antioxidant (free radicals scavenger: DPPH radical, IC50 = 1.4 μmol/L, ONOO-radical, IC50 = 2.2 μmol/L, O2•− radical, IC50 = 50 μmol/L inactive, NO• radical, IC50 = 0.4 μmol/L). Ref: B. W. Son, et al, JNP, 2002, 65, 794

90

2 Aromatic Metabolites

OH

Cl

OH OH

289 Chlorogentisyl alcohol 2-Chloro-6-(hydroxymethyl)-1,4-benzenediol Type: Benzyl alcohols. C7H7ClO3 Needles (EtOAc/petrol), mp 147–148 °C, mp 140–141.5 °C. Source: Marine-derived fungus Phoma herbarum from red alga Gloiopeitis tenax (addition of halide salts to fermentation medium, Cheokpo, Tongnyeong, R. O. Korea), Aspergillus varians and Ampelomyces sp. Pharm: Antioxidant (DPPH scavenger, IC50 = 1.0 μmol/L, control L-Ascorbic acid, IC50 = 20 μmol/L); antibacterial. Ref: O. F. Smetanina, et al, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 243│V. N. Nenkep, et al, J. Antibiot., 2010, 63, 199 OH Cl

OH

OH

290 2-Chloro-6-(methoxymethyl)-1,4-benzenediol Type: Benzyl alcohols. C8H9ClO3 Amorph. powder. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 6.7 μmol/L; Molt4, IC50 = 64.7 μmol/L; A549, IC50 = 56.5 μmol/L; Bel7402, IC50 = 58.1 μmol/L); antioxidant (DPPH scavenger, IC50 = 8.5 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH Cl O

OH

291 2,3-Dibromo-4,5-dihydroxybenzyl alcohol Type: Benzyl alcohols. C7H6Br2O3 Cryst. (C6H6), mp 129–130 °C. Source: Red algae Odonthalia corymbifera and Lenormandia prolifera, red algae Polysiphonia spp., Odonthalia spp., and Rhodomela spp. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Saccharomyces cerevisiae, IC50 = 89.0 μmol/L). Ref: H. Kurihara, et al, Fish. Sci. 1999, 65, 300│CRC Press, DNP on DVD, 2012, version 20.2│ Y. Sharifuddin, et al, Mar. Drugs, 2015, 13, 5447 (rev)

2.1 Simple Benzene Derivatives

HO

91

OH

HO

Br Br

292 Gentisyl alcohol 2,5-Dihydroxybenzyl alcohol Type: Benzyl alcohols. C7H8O3 Red-brown cryst. (Et2O/petrol), mp 104–105 °C. Source: Marine-derived fungi Phoma herbarum from red alga Gloiopeitis tenax (addition of halide salts to fermentation medium, Cheokpo, Tongnyeong, R. O. Korea), Aspergillus parasiticus and Aspergillus varians. Pharm: Antioxidant (free radicals scavenger: DPPH radical, IC50 = 0.6 μmol/L, ONOO− radical, IC50 = 3.1 μmol/L, O2•−radical, IC50 = 11.0 μmol/L, NO• radical, IC50 = 0.5 μmol/L, control carboxy-PTIO, IC50 = 137.7 μmol/L); antioxidant (DPPH scavenger, IC50 = 7.0 μmol/L). Ref: B. W. Son, et al, JNP, 2002, 65, 794│O. F. Smetanina, et al, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 243│V. N. Nenkep, et al, J. Antibiot., 2010, 63, 199 OH HO OH

293 Terrestrol B Type: Benzyl alcohols. C14H13ClO5 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 6.1 μmol/L; Molt4, IC50 = 5.8 μmol/L; A549, IC50 = 18.3 μmol/L; Bel7402, IC50 = 62.3 μmol/L); antioxidant (DPPH scavenger, IC50 = 4.3 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH

OH Cl O

OH

OH

294 Terrestrol C Type: Benzyl alcohols. C14H14O5 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 5.5 μmol/L; Molt4, IC50 = 5.6 μmol/L; A549, IC50 = 18.2 μmol/L; Bel7402, IC50 = 57.3 μmol/L); antioxidant (DPPH scavenger, IC50 = 4.6 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66

92

2 Aromatic Metabolites

OH

OH O

OH

OH

295 Terrestrol D Type: Benzyl alcohols. C14H13ClO5 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 5.3 μmol/L; Molt4, IC50 = 5.5 μmol/L; A549, IC50 = 14.3 μmol/L; Bel7402, IC50 = 38.5 μmol/L); antioxidant (DPPH scavenger, IC50 = 4.4 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 Cl OH

OH O

OH

OH

296 Terrestrol E Type: Benzyl alcohols. C14H14O5 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 54.7 μmol/L; Molt4, IC50 = 6.4 μmol/L; A549, IC50 = 9.6 μmol/L; Bel7402, IC50 = 59.0 μmol/L); antioxidant (DPPH scavenger, IC50 = 6.2 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH

OH O

OH

OH

297 2,3,6-Tribromo-4,5-dihydroxybenzyl alcohol Type: Benzyl alcohols. C7H5Br3O3 mp 128–130 °C. Source: Red algae Symphyocladia latiuscula, Polysiphonia lanosa, Polysiphonia elongata and Rhodomela subfusca. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 11.0 μmol/L); hypoglycemic (sucrase inhibitor) (in vitro assay, IC50 = 4.2 mmol/L); hypoglycemic (maltase inhibitor) (in vitro assay, IC50 > 5.0 mmol/L); antibiotic; Antioxidant (DPPH radical scavenger). Ref: H. Kurihara, et al, Fish. Sci. 1999, 65, 300│CRC Press, DNP on DVD, 2012, version 20.2

2.1 Simple Benzene Derivatives

93

Br HO

OH

HO

Br Br

298 2,3,6-Tribromo-4,5-dihydroxybenzyl methyl ether Type: Benzyl alcohols. C8H7Br3O3 Source: Red alga Symphyocladia latiuscula. Pharm: Hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 3.9 μmol/L). Ref: X. Liu, et al, Chin. J. Oceanol. Limnol., 2011, 29, 686 O Br

Br

Br

OH OH

299 2,2′,3-Tribromo-3′,4,4′,5-tetrahydroxy-6′-ethyloxymethyldiphenylmethane Type: Benzyl alcohols. C16H15Br3O5 Source: Red alga Rhodomela confervoides. Pharm: Hypoglycemic (PTP1B inhibitor) (PTP1B and hypoglycaemic effect in streptozotocin-induced diabetic Wistar rats, IC50 = 0.84 μmol/L). Ref: D. Shi, et al, Chin. Sci. Bull., 2008, 53, 2476 Br

Br

HO

Br

HO

OH O

OH

300 3-(2-Acetoxy-4,8-dimethyl-3,7-nonadienyl)benzaldehyde Type: Benzaldehydes. C20H26O3 Oil, [α]D25 = +2.4° (c = 0.5, CHCl3). Source: Green algae Halimeda spp. Pharm: Antimicrobial; cytotoxic. Ref: V. J. Paul, et al, Tetrahedron, 1984, 40, 3053 O O O H

94

2 Aromatic Metabolites

301 Chaetopyranin 5-Formyl-6-hydroxy-2-(3-hydroxy-1-butenyl)-7-prenylchroman Type: Benzaldehydes. C19H24O4 Yellowish powder (Me2CO), mp 136–138 °C, [α]D22 = +8° (c = 0.5, MeOH). Source: Marine-derived fungus Chaetomium globosum from red alga Polysiphonia urceolata (China waters). Pharm: Antioxidant (DPPH scavenger, moderate); cytotoxic (SMMC-7721, A549, and HMEC, moderate to weak). Ref: S. Wang, et al, JNP, 2006, 69, 1622 H

O

HO

O

302 Cylindrocarpol Type: Benzaldehydes. C23H34O5 Gum, [α]D23 = −11.7° (c = 0.3, 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│S. B. Singh, et al, JOC, 1996, 61, 7727 O

OH

OH

H OH OH

303 Flavoglaucin Type: Benzaldehydes. C19H28O3 Pale yellow cryst., mp 109–110 °C, mp 103 °C. Source: Marine-derived fungus Microsporum sp. from red alga Lomentaria catenata (Korea, surface). Pharm: Antioxidant (DPPH scavenger, IC50 = 11.3 μmol/L, control, Ascorbic acid, IC50 = 20 μmol/L); mycotoxin; antineoplastic. Ref: Y. Li, et al, CPB, 2006, 54, 882 OH

O OH

H

304 p-Hydroxybenzaldehyde p-Formylphenol Type: Benzaldehydes. C7H6O2 Needles (H2O), mp 115–116 °C, pKa = 7.62 (25 °C, H2O). Source: Mangrove-derived fungus Pestalotiopsis sp. from Rhizophora

2.1 Simple Benzene Derivatives

95

mucronata (China waters), green alga Boodlea composita. Pharm: Immunosuppressive; phytotoxic. Ref: S. F. Hinkley, et al, J. Antibiot., 1999, 52, 988 O H

HO

305 Isodihydroauroglaucin Type: Benzaldehydes. C19H24O3 Yellow needles (hexane), mp 114–115 °C. Source: Marine-derived fungus Microsporum sp. from red alga Lomentaria catenata (Korea, surface). Pharm: Antioxidant (DPPH scavenger, IC50 = 11.5 μmol/L, control, Ascorbic acid, IC50 = 20 μmol/L). Ref: Y. Li, et al, CPB, 2006, 54, 882 OH

O OH

H

306 Redoxcitrinin Type: Benzaldehydes. C13H16O4 Source: Marine fungus Penicillium sp. MFA446 from green alga Ulva pertusa (Korea waters). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: D. Zhang, et al, J. Microbiol. Biotechnol., 2007, 17, 865

HO O OH

O

307 2,3,6-Tribromo-4,5-dihydroxybenzaldehyde Type: Benzaldehydes. C7H3Br3O3 Amorph. yellowish solid, mp 134–135 °C. Source: Red alga Symphyocladia latiuscula. Pharm: Hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 19.40 μmol/L). Ref: W. Wang, et al, JNP, 2005, 68, 620│X. Liu, et al, Chin. J. Oceanol. Limnol.,2011, 29, 686 H

O

Br

Br

Br

HO OH

96

2 Aromatic Metabolites

308 Acetylbenzoyl Methyl phenyl diketone Type: Aryl ketones. C9H8O2 Yellow oil with a pungent odour, bp 222 °C, bp12mmHg 102 °C. Source: Marine-derived bacterium (family Rhodobacteraceae) Oceanibulbus indolifex HEL-4. Pharm: Flavouring ingredient. Ref: V. Thiel, et al, Org. Biomol. Chem., 2010, 234 O

O

309 Communol A Type: Aryl ketones. C16H16O6 Source: Marine-derived fungus Penicillium commune 518 from gorgonian Muricella abnormalis (Danzhou, Hainan, China). Pharm: Antibacterial (Escherichia coli, MIC = 4.1 μmol/L; Enterobacter aerogenes, MIC = 16.4 μmol/L). Ref: J. Wang, et al, Chin. J. Chem., 2012, 30, 1236; 2880 OH

O

OH

O

O HO

310 Communol F Type: Aryl ketones. C10H10O4 Source: Marine-derived fungus Penicillium commune 518 from a gorgonian, two marine fungi (Strains E33 and K38, co-culture broth). Pharm: Antibacterial (Enterobacter coli, MIC = 6.4 μmol/L, Enterobacter aerogenes, MIC = 25.8 μmol/L). Ref: J. Wang, et al, Chin. J. Chem., 2012, 30, 1236; 2880 O

OH

O

H HO

311 Communol G Type: Aryl ketones. C11H14O4 Source: Marine-derived fungus Penicillium commune 518 from a gorgonian, two marine fungi (Strains E33 and K38, co-culture broth). Pharm: Antibacterial (Enterobacter coli, MIC = 23.8 μmol/L, Enterobacter aerogenes, MIC = 23.8 μmol/L). Ref: J. Wang, et al, Chin. J. Chem., 2012, 30, 1236; 2880 OH HO O

O

2.1 Simple Benzene Derivatives

97

312 Cytosporone B Type: Aryl ketones. C18H26O5 Source: Mangrove-derived fungus Leucostoma persoonii from mangrove Rhizophora mangle (branch, Everglades, Florida), Cytospora sp. Pharm: Antibacterial (MRSA, MIC = 78 μmol/L, MBC90 = 93 μmol/L, MBEC90, = 110 μmol/L; A549 IC50 = 170 μmol/L, IC90 = 190 μmol/L). Ref: M. P. Singh, et al, Mar. Drugs, 2007, 5, 71│J. Beau, et al, Mar. Drugs, 2012, 10, 762 OH

O 6

HO O

O

313 6-Demethylsorbicillin 1-(2,4-Dihydroxy-5-methylphenyl)-2,4-hexadien-1-one Type: Aryl ketones. C13H14O3 Yellow solid (MeOH). Source: Marine-derived fungus Trichoderma sp. f-13 (sediment, Fujian province, China). Pharm: Cytotoxic (HL60 cell line, IC50 = 23.9 μmol/L, control VP-16, IC50 = 2.1 μmol/L; increases in cells percentage in sub-G1 fraction, sub-G1 = 66.4%, negative control MeOH, sub-G1 = 2.3%). Ref: L. Du, et al, CPB, 2009, 57, 220 OH

O

HO

314 Ethyl 5-ethoxy-2-formyl-3-hydroxy-4-methylbenzoate Type: Aryl ketones. C13H16O5 Colorless needles. Source: Two marine fungi (Strains E33 and K38, co-culture broth). Pharm: Antifungal (0.25 mmol/L: Blumeria graminearum, IZD = 12.1 mm, Gloeosporium musae, IZD = 11.6 mm, Rhizoctonia solani, IZD = 10.2 mm, Phytophthora sojae, IZD = 8.5 mm). Ref: J. H. Wang, et al, Chem. Nat. Compd. 2013, 49, 799 O O

O H OH

O

315 Isosorbicillin (2E,4E)-1-(2,6-Dihydroxy-3,5-dimethyl-phenyl)hexa-2,4-dien-1-one Type: Aryl ketones. C14H16O3 Yellow needles. Source: Marine-derived fungus Penicillium sp. M207142.

98

2 Aromatic Metabolites

Pharm: Cytotoxic (HeLa and SW620, strong). Ref: S. Liu, et al, Chem. Nat. Compd., 2010, 46, 116 OH

O

OH

316 5-O-Methyldothiorelone A Ethyl 2-(3-hydroxy-2-(7-hydroxyoctanoyl)-5-methoxyphenyl) acetate Type: Aryl ketones. C19H28O6 Oil. Source: Mangrove-derived fungus Phomopsis sp. ZSU-H76 from mangrove Excoecaria agallocha (China waters). Pharm: Cytotoxic (MTT assay, Hep2, IC50 = 25 μg/mL; HepG2, IC50 = 30 μg/mL). Ref: Z. J. Huang, et al, Chem. Nat. Compd., 2009, 45, 625 O O

O

O

OH

OH

317 14,15-Secocurvularin Type: Aryl ketones. C16H22O5 Source: An unidentified marine-derived fungus 951014 from sponge Spirastrella vagabunda (Indo-Pacific). Pharm: Antibacterial (Bacillus subtilis, mild than tetracycline). Ref: L. M. Abrell, et al, Tet. Lett., 1996, 37, 8983 O O

HO

O

OH

318 Sohirnone A 1-(2,4-Dihydroxy-5-methylphenyl)-4-hexen-1-one Type: Aryl ketones. C13H16O3 Pale yellow solid. Source: Marine-derived fungus Trichoderma sp. f-13 (Chinese sediment sample, China waters). 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 = 5.4%, negative control MeOH, sub-G1 = 2.3%). Ref: L. Du, et al, CPB, 2009, 57, 220│R. P. Maskey, et al, JNP, 2005, 68, 865

2.1 Simple Benzene Derivatives

OH

99

O

HO

319 (4ʹZ)-Sorbicillin Type: Aryl ketones. C14H16O7 Source: Marine-derived fungus Trichoderma sp. from starfish Acanthaster planci (Hainan Sanya National Coral Reef Reserve, China). Pharm: Cytotoxic (several HTCLs cells, moderate). Ref: W. -J. Lan, et al, Nat. Prod. Commun., 2012, 7, 1337 OH

O

HO

320 Ascochital 4-(1,3-Dimethyl-2-oxopentyl)-3-formyl-2,6-dihydroxybenzoic acid Type: Benzoic acids and esters. C15H18O6 mp 122–124 °C. Source: Marine-derived fungus Ascochyta salicorniae from green alga Ulva sp. (North Sea coast, Germany), marine-derived fungus Kirschsteiniothelia maritima. Pharm: PPs inhibitors (MPtpB (mycobacterial protein tyrosine phosphatase B), IC50 = 61.2 μmol/L; Cdc25a, PTP1B, VHR, MPtpA and VE-PTP, all inactive); antibacterial (Bacillus subtilis, MIC = 500 ng/mL). Ref: C. Kusnick, et al, Pharmazie, 2002, 57, 510│S. F. Siebert, et al, Org. Biomol. Chem., 2006, 4, 2233

HO O

HO O

OH

O

321 1,2-Benzenedicarboxylic acid2,12-diethyl-11-methylhexadecyl 2-ethyl11-methylhexadecyl ester Type: Benzoic acids and esters. C48H86O4 Source: Fish (seahorse) Hippocampus Kuda. Pharm: Cathepsin B inhibitor (IC50 = 0.18–0.29 mmol/L). Ref: Y. Li, et al, BoMCL, 2008, 18, 6130

100

2 Aromatic Metabolites

O O O O

322 1,2-Benzenedicarboxylic acid2-Ethyldecyl 2-ethylundecyl ester Type: Benzoic acids and esters. C33H56O4 Source: Fish (seahorse) Hippocampus Kuda. Pharm: Cathepsin B inhibitor (IC50 = 0.18–0.29 mmol/L). Ref: Y. Li, et al, BoMCL, 2008, 18, 6130 O O O O

323 Bis(2-ethyldodecyl) phthalate Type: Benzoic acids and esters. C36H62O4 Source: Fish (seahorse) Hippocampus Kuda. Pharm: Cathepsin B inhibitor (IC50 = 0.18–0.29 mmol/L). Ref: Y. Li, et al, BoMCL, 2008, 18, 6130 O O O O

324 Butyl-isobutylphthalate Type: Benzoic acids and esters. C16H22O4 Source: Brown alga Laminaria japonica (rhizoids). Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 38.00 μmol/L); hypoglycaemic (in vivo, streptozotocin-induced diabetic mice). Ref: T. Bu, et al, Phytother. Res., 2010, 24, 1588

O

O

O O

2.1 Simple Benzene Derivatives

101

325 3,4-Dihydroxybenzoic acid Hypogallicacid Type: Benzoic acids and esters. C7H6O4 Source: Marine-derive fungus Neosartorya fischeri 1008F1, various higher plants. Pharm: Antiviral (TMV virus, IC50 = 630 μmol/L); antioxidant; free radical scavenger; dietary chemopreventive agent (inhibits development of neoplasms in animal models); inhibits LDL oxidation; platelet aggregation inhibitor. Ref: Q. -W. Tan, et al, Nat. Prod. Res., 2012, 26, 1402│CRC press, DNP in DVD, 2012, version20.2 O HO

OH

HO

326 4-Hydroxybenzoic acid Type: Benzoic acids and esters. C7H6O3 Prisms (xylene/EtOH), cryst. + 1H2O (EtOH aq or Me2CO/EtOH), mp 213–214 °C. Source: Marine-derived fungus Nigrospora sp. PSU-F12 from gorgonian sea fan Annella sp. (Thailand). Pharm: Antifungal; eye irritant (eye, skin); LD50 (mus, orl) = 2200 mg/kg. Ref: V. Rukachaisirikul, et al, Arch. Pharmacal Res., 2010, 33, 375 O OH HO

327 5-Hydroxy-2-methoxy benzoic acid Type: Benzoic acids and esters. C8H8O4 Source: Deep-sea fungus Aspergillus sp. CXCTD-06-6a. Pharm: Cytotoxic (1.68 μg/mL, HeLa, InRt = 7.29%). Ref: C. Ji, et al, Chin. J. Mar. Drugs, 2011, 30, 1 OH

O O

OH

328 (2′S)-4-Methoxy-3-(2′-methyl-3′-hydroxy) propionyl-methyl benzoate Type: Benzoic acids and esters. C13H16O6 Source: Deep-sea fungus Aspergillus sp. 16-02-1 (sediment). Pharm: Cytotoxic (100 μg/mL: K562, InRt = 34.5%; HL60, InRt = 25.2%; HeLa, InRt = 3.2%; BGC823, InRt = 15.5%). Ref: X. Chen, et al, Chin. J. Mar. Drugs, 2013, 32, 1 (in Chinese)

102

2 Aromatic Metabolites

O OH

O O

O

O

329 Methyl 4-hydroxy-3-(3-methylbut-2-enyloxy)benzoate Type: Benzoic acids and esters. C13H16O4 mp 49–50 °C. Source: Mangrove-derived unidentified fungus (from Chinese mangrove habitat). Pharm: Antibacterial (grampositive bacterium Staphylococcus aureus ATCC27154, MIC = 6.25 μg/mL; gramnegative bacterium Escherichia coli ATCC 25922; MIC = 25 μg/mL, moderate); antifungal (Fusarium oxysporum, MIC = 12.5 μg/mL, Candida albicans ATCC 10231, inactive); cytotoxic (MTT assay, HepG2, IC50 = 10.0 μg/mL, moderate). Ref: C. L. Shao, et al, Chem. Nat. Compd., 2007, 43, 377 OH O

O O

330 Tenellic acid C Type: Benzoic acids and esters. C23H26O8 Amorph. solid, mp 108–110 °C, [α]D = −7.4° (c = 0.13, MeOH). Source: Mangrove-derived fungus Talaromyces sp. SBE-14 from mangrove Kandelia candel (Hong Kong). Pharm: Antibacterial (standard disk assays, 200 μg/disk: gram-positive bacterium Bacillus subtilis ATCC 6051, IZD = 12 mm; Staphylococcus aureus ATCC 29213, IZD = 14 mm; Candida albicans ATCC 14053, inactive). Ref: H. Oh, et al, JNP, 1999, 62, 580│F. Liu, et al, Magn. Reson. Chem., 2009, 47, 453 O

H

O

OH O

O

OH O O

331 (+)-Aeroplysinin 1 3,5-Dibromo-1-cyanomethyl-4-methoxy-3,5-cyclohexadiene-1,2-diol Type: Phenylethanoids. C9H9Br2NO3 mp 120–121 °C, mp 112–113 °C, [α]D = +193° (c = 0.63, Me2CO), [α]D20 = +185° (c = 0.17, MeOH). Source: Sponges Aplysina aerophoba [Syn. Verongia aerophoba], Aplysina archeri, Aiolochroia crassa, Verongula rigida, Psammaplysilla

2.1 Simple Benzene Derivatives

103

purpurea and Ianthella sp. Pharm: Antibacterial (Photobacterium phosphoreum, IC50 = 3.5 μmol/L) (García-Vilas, 2016); antimicroalgal (marine microalgae Coscinodiscus wailesii, IC50 = 5.6 μmol/L, Prorocentrum minimum, IC50 = 7.0 μmol/L) (García-Vilas, 2016); antiviral (HIV-1, IC50 = 14.6 μmol/L) (García-Vilas, 2016); antiangiogenic (EVLC-2 Cell Line, 2.5 μmol/L, target MMP-2, effect decrease; HUVEC Cell Line, 2.5 μmol/L, target MMP-2, effect decrease; RF-24 Cell Line, 2.5 μmol/L, target MMP-2, effect decrease; BAEC Cell Line, 3 μmol/L, target MMP-2, effect decrease; BAEC Cell Line, 3 μmol/L, target PA, effect decrease; BAEC Cell Line, 3 μmol/L, target PAI, effect increase) (García-Vilas, 2016); anti-inflammatory (HUVEC Cell Line, 10 μmol/L, target MCP-1, effect decrease; HUVEC Cell Line, 10 μmol/L, target TSP-1, effect decrease; HUVEC Cell Line, 10 μmol/L, target COX-2, effect decrease; HUVEC Cell Line, 20 μmol/L, target Il-1α, effect decrease; HUVEC Cell Line, 20 μmol/L, target MMP-1, effect decrease) (García-Vilas, 2016); apoptogenic (BAEC Cell Line, 10 μmol/L, target Cleaved lamin-A, effect increase; BAEC Cell Line, 10 μmol/L, target Caspase-2, -3, -8, -9, effect increase; BAEC Cell Line, 10 μmol/L, target Cytochrome C, effect increase in cytoplasm; HUVEC Cell Line, 10 μmol/L, target p-Bad, effect increase) (García-Vilas, 2016); anti-angiogenic (HUVEC (hmn umbilical vein endothelial cells), IC50 = 4.7 μmol/L; EVLC-2 (SV40 large T-antigen immortalized hmn umbilical vein cells), IC50 = 3.0 μmol/L; RF-24 (papillomavirus 16 E6/E7 immortalized hmn umbilical vein cells), IC50 = 2.8 μmol/L; HMEC (hmn microvascular endothelial cells), IC50 = 2.6 μmol/L; BAEC (bovine aortic endothelial cells,), IC50 = 2.1 μmol/L) (García-Vilas, 2016); cytotoxic (HT1080, IC50 = 2.3 μmol/L, HTC116, IC50 = 4.7 μmol/L, HeLa, IC50 = 3.0 μmol/L, THP-1, IC50 = 10.0 μmol/L, NOMO-1, IC50 = 17.0 μmol/L, HL60, IC50 = 5.0 μmol/L) (García-Vilas, 2016); antibiotic (Gram-positive bacteria and several dinoflagellate microalgae causing toxic blooms) (García-Vilas, 2016); EGFR inhibitor (IC100 = 0.5 μmol/L); antitumor (strong effect on EGFR tumor cell lines, blocking proliferation of EGFR-dependent hmn breast cancer cell lines MCF7 and ZR-75-1); molluscacidal. Note: (+)-Aeroplysinin 1 has a wide spectrum of bio-activities. In preclinical studies, it has been shown to have promising anti-inflammatory, anti-angiogenic and anti-tumor effects. It might have a pharmaceutical interest for the treatment of different pathologies. Ref: T. N. Makarieva, et al, Comp. Biochem. Physiol., B, 1981, 68, 481│M. -H. Kreuter, et al, Comp. Biochem. Physiol. B Biochem. Mol. Biol. 1990, 97, 151│A. Koulman, et al, JNP, 1996, 59, 591│M. Kita, et al, Tet. Lett., 2008, 49, 5383│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev)│J. A. García-Vilas, et al, Mar. Drugs, 2016, 14, 1 (rev) O Br

Br

HO HO

N

104

2 Aromatic Metabolites

332 4-Hydroxy-3-methoxyphenylglyoxylic acid methyl ester Vanilloylformic acid Type: Phenylethanoids. C10H10O5 Yellow amorph. powder. Source: Ascidian Polyandrocarpa zorritensis (Bay of Taranto, Mediterranean Sea). Pharm: Cytotoxic (C6, IC50 > 1000 μmol/L; HeLa and H9c2, inactive). Ref: A. Aiello, et al, Mar. Drugs, 2011, 9, 1157 O O

O O

HO

333 4-Hydroxyphenethyl 2-(4-hydroxyphenyl) acetate Type: Phenylethanoids. C16H16O4 Source: Mangrove-derived fungus Penicillium griseofulvum Y19-07 from mangrove Lumnitzera racemosa. Pharm: Antioxidant (radical scavenger, moderate); cytotoxic (weak). Ref: Y. N. Wang,et al, J. Asian Nat. Prod. Res., 2009, 11, 912 O O

HO

OH

334 4-Hydroxyphenethyl methyl succinate Type: Phenylethanoids. C13H16O5 Oil. Source: Mangrove-derived fungus Penicillium griseofulvum Y19-07 from mangrove Lumnitzera racemosa. Pharm: Antioxidant (radical scavenger, moderate). Ref: Y. N. Wang,et al, J. Asian Nat. Prod. Res., 2009, 11, 912 O O O O HO

335 Isojaspisin Type: Phenylethanoids. C8H8O6S Viscous oil (Na salt). Source: Sponge Jaspis sp. (Japan waters). Pharm: Inhibits hatching of sea urchin embryos. Ref: C. M. Cerda-Garcia-Rojas, et al, JNP, 1994, 57, 1758 HO

HO

O O

S

O

O

H

2.1 Simple Benzene Derivatives

105

336 Jaspisin 3,4-Dihydroxystyryl sulfate Type: Phenylethanoids. C8H8O6S Viscous oil (Na salt). Source: Sponges Poecillastra wondoensis and Jaspis sp. (Japan waters). Pharm: Sea urchin gamete inhibitor; endoproteinase inhibitor; fertilisation inhibitor (Asterina pectinifera). Ref: C. M. Cerda-Garcia-Rojas, et al, JNP, 1994, 57, 1758│S. Ohta, et al, Biosci. Biotechnol. Biochem., 1994, 58, 1752│S. Ikegami, et al, J. Biol. Chem., 1994, 269, 23262│Y. H. Chang, et al, JNP, 2008, 71, 779 H HO

O H

HO

S O

O OH

337 Methyl 4-hydroxyphenylacetate Type: Phenylethanoids. C9H10O3 Source: Marine fungus Penicillium oxalicum 0312f1. Pharm: Antiviral (TMV virus, EC50 = 829.15 μmol/L). Ref: S. Shen, et al, Acta Microbiol. Sinic., 2009, 49, 1240│S. Shen, et al, Nat. Prod. Res., 2013, 27, 2286 O O

HO

338 Subereaphenol B 4,6-Dibromo-homogentisic acid methyl ester Type: Phenylethanoids. C9H8Br2O4 Source: Sponges Pseudoceratina sp. (Vanuatu), Suberea sp. (Hurghada, Red Sea, Egypt) and Suberea mollis. Pharm: Pfnek-1 (a NIMA-related protein kinase of Plasmodium falciparum) inhibitor (IC50 = 1.8 μmol/L). Ref: M. I. Abou-Shoer, et al, JNP, 2008, 71, 1464│N. Lebouvier,et al, Mar. Drugs, 2009, 7, 640│K. H. Shaker, et al, Chem. Biodiversity, 2010, 7, 2880│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH Br

Br

O O OH

339 (3S)-(3,5-Dihydroxyphenyl)butan-2-one Type: Phenylpropanoids. C10H12O3 Oil, [α]D20 = +124.0° (c = 0.12, CHCl3). Source: Marine-derived fungus Coniothyrium sp. from sponge Ectyoplasia ferox. Pharm: Antifungal (Ustilago violacea). Ref: U. Höller, et al, JNP, 1999, 62, 114

106

2 Aromatic Metabolites

HO

O 3

OH

340 Ethyl 3,5-dibromo-4(3ʹN,N-dimethylaminopropyloxy)-cinnamate Type: Phenylpropanoids. C16H21Br2NO3 Flakes, mp 67 °C. Source: Sponge Pseudoceratina crassa. Pharm: Antibacterial. Ref: K. E. Kassühlke, et al, Tetrahedron, 1991, 47, 1809 Br O N

O Br O

341 Fijiolide A Type: Phenylpropanoids. C34H38Cl2N2O10 Pale yellow oil, [α]D21 = −440° (c = 0.5, MeOH). Source: Marine-derived actinomycete Nocardiopsis sp. CNS-653. Pharm: TNF-α-induced NF-κB activation inhibitor. Ref: S. -J. Nam, et al, JNP, 2010, 73, 1080 Cl

OH

O O N

O H

HO

O

Cl

O

O NH

OH OH

342 Hibiscusamide N-trans-Feruloyl-3,5-dimethoxytyramine Type: Phenylpropanoids. C20H23NO6 Needles (EtOH) or yellow solid, mp 126–128 °C, [α]D25 = −18° (c = 0.68, MeOH). Source: Semimangrove Hibiscus tiliaceus (stem wood). Pharm: Cytotoxic. Ref: J. -J. Chen, et al, Planta Med., 2006, 72, 932 O HO

O

O N H

O

OH

2.1 Simple Benzene Derivatives

107

343 Phenol A 5-[(2S,3R)-3-Hydroxybutan-2-yl]-4-methylbenzene-1,3-diol Type: Phenylpropanoids. C11H16O3 Source: Marine-derived fungus Penicillium sp. MFA446 from green alga Ulva pertusa (Korea waters), deep-sea fungus Aspergillus sydowi YH11-2 (Guam, depth of 1000 m, E144°43′ N13°26′). Pharm: Antioxidant (DPPH scavenger, moderate); cytotoxic (P388, IC50 = 10.41 μmol/L, control CDDP, IC50 = 0.039 μmol/L). Ref: R. F. Curtis, et al, JCS Perkin I, 1968, 1, 85│Zhang, D. et al, J. Microbiol. Biotechnol., 2007, 17, 865│L. Tian, et al, Arch. Pharm. Res,. 2007, 30, 1051

HO OH OH

344 Sulfated cinnamic acid Type: Phenylpropanoids. C9H8O6S Source: Marine monocotyledon Zostera marina. Pharm: Antifoulant. Ref: J. S. Todd, et al, Phytochemistry, 1993, 34, 401 O O

OH

HO S O O

345 Aspergillusene A Type: Other phenylalkanoids (C4–C8). C15H22O2 Source: Marine-derived fungus Aspergillus sydowii ZSDS1-F6. Pharm: Antibacterial (Klebsiella pneumonia, MIC = 21.4 μmol/L). Ref: J. -F. Wang, et al, J. Antibiot., 2014, 67, 581 OH

OH

346 Caulerprenylol A Type: Other phenylalkanoids (C4–C8). C18H26O2 Source: Green alga Caulerpa racemosa (Zhanjiang coastline, China). Pharm: Antifungal (weak). Ref: A. -H. Liu, et al, Bioorg. Med. Chem. Lett., 2013, 23, 2491

108

2 Aromatic Metabolites

OH

OH

347 Caulerprenylol B Type: Other phenylalkanoids (C4–C8). C18H26O2 Source: Green alga Caulerpa racemosa (Zhanjiang coastline, China). Pharm: Antifungal (weak). Ref: A. -H. Liu, et al, Bioorg. Med. Chem. Lett., 2013, 23, 2491

H OH H OH

348 1,11-Dihydroxy-1,3,5,7E-bisabolatetren-15-oic acid Engyodontiumone I Type: Other phenylalkanoids (C4–C8). C15H20O4 Yellow gum. Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Antibacterial (Bacillus subtilis, 25 μg/disc, IZ = 10.0 mm, control PG, 10 μg/disc, IZ = 43.3 mm, MIC = 256.0 μg/mL, PG, MIC = 2.0 μg/mL). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902 O OH

HO

OH E

349 (Z)-5-(Hydroxymenthyl)-2-(6′-methylhept-2′-en-2′-yl)-phenol Type: Other phenylalkanoids (C4–C8). C15H22O2 Source: Marine-derived fungus Aspergillus sydowii ZSDS1-F6. Pharm: Antiviral (H3N2 virus, IC50 = 57.4 μmol/L); antibacterial (Klebsiella pneumonia, MIC = 10.7 μmol/L). Ref: J. -F. Wang, et al, J. Antibiot., 2014, 67, 581 OH

OH

2.1 Simple Benzene Derivatives

109

350 Lorneic acid A 4-[2-(1-Hexenyl)-4-methylphenyl]-3-butenoic acid Type: Other phenylalkanoids (C4–C8). C17H22O2 Oil. Source: Marine-derived streptomycete Streptomyces sp. NPS554 (sediment, Miyazaki Harbor, Japan waters). Pharm: Hmn platelet phosphodiesterase 5 inhibitor (PDE5) (strong). Ref: F. Iwata, et al, JNP, 2009, 72, 2046 O OH

351 Lorneic acid B Type: Other phenylalkanoids (C4–C8). C17H24O3 Oil, [α]D = −22° (c = 0.2, MeOH). Source: Marine-derived streptomycete Streptomyces sp. NPS-554 (sediment, Miyazaki Harbor, Japan waters). Pharm: Hmn platelet phosphodiesterase 5 inhibitor (PDE5). Ref: F. Iwata, et al, JNP, 2009, 72, 2046 COOH

OH

352 Nakitriol Type: Other phenylalkanoids (C4–C8). C11H12O3 Source: Cyanobacterium Synechocystis sp. growth on stony coral Acropora sp. (Okinawa). Pharm: Cytotoxic (DNA repair defective cell lines: EM9 (topoisomerase I sensitive Chinese hamster ovary line), XRS-6 (topoisomerase II sensitive Chinese hamster ovary line), UV20 (DNA cross-linking agent sensitive Chinese hamster ovary line), and BR1 (DNA repair competent Chinese hamster ovary line), all LD50 ≈ 20 μg/mL). Ref: D. G. Nagle, et al, Tet. Lett., 1995, 36, 849 OH OH HO

110

2 Aromatic Metabolites

353 Rubrenoic acid A Type: Other phenylalkanoids (C4–C8). C16H22O2 Source: Marine bacterium Alteromonas rubra. Pharm: Bronchodilator. Ref: G. S. Holl, et al, Chem. Ind. (London), 1984, 850 OH O

354 Rubrenoic acid B Type: Other phenylalkanoids (C4–C8). C16H20O2 Source: Marine bacterium Alteromonas rubra. Pharm: Bronchodilator. Ref: G. S. Holl, et al, Chem. Ind. (London), 1984, 850 OH O

355 Rubrenoic acid C Type: Other phenylalkanoids (C4–C8). C16H20O2 Source: Marine bacterium Alteromonas rubra. Pharm: Bronchodilator. Ref: G. S. Holl, et al, Chem. Ind. (London), 1984, 850 OH O

356 Strepchloritide A Type: Other phenylalkanoids (C4–C8). C10H8Cl2O4 Source: Marine-derived streptomycete Streptomyces sp. from an unidentified soft coral (Weizhou I., Guangxi, China). Pharm: Cytotoxic (MCF7, modest). Ref: P. Fu, et al, Chin. J. Chem., 2013, 31, 100 Cl O

Cl

OH

HO

OH

357 Strepchloritide B Type: Other phenylalkanoids (C4–C8). C10H7Cl3O4 Source: Marine-derived streptomycete Streptomyces sp. from an unidentified soft coral (Weizhou I., Guangxi, China). Pharm: Cytotoxic (MCF7, modest). Ref: P. Fu, et al, Chin. J. Chem., 2013, 31, 100

2.1 Simple Benzene Derivatives

111

Cl

Cl

O

Cl

OH

HO

OH

358 (ξ)-Sydonic acid 1,7-Dihydroxy-1,3,5-bisabolatrien-15-oic acid Type: Other phenylalkanoids (C4–C8). C15H22O4 Needles (C6H6), mp 158–159 °C. Source: Deep-sea fungus Engyodontium album DFFSCS021, terrestrial and marine-derived Aspergillus sydowi, order Pleosporales sp. (fresh water). Pharm: Antibacterial (Escherichia coli, 25 μg/disc, IZ = 11.4 mm, control PG, 10 μg/disc, IZ = 31.8 mm, MIC = 64.0 μg/mL, PG, MIC = 2.0 μg/mL; Bacillus subtilis, 25 μg/disc, IZ = 13.6 mm, control PG, 10 μg/disc, IZ = 43.3 mm, MIC = 128.0 μg/mL, PG, MIC = 2.0 μg/mL). Ref: N. Ein-Gil, et al, ISME J., 2009, 3, 752│T. Hosoe, et al, Heterocycles, 2010, 81, 2123│Q. Yao, et al, Mar. Drugs, 2014, 12, 5902 O 1

HO

OH

15 11

7

OH

359 Varioxirane Type: Other phenylalkanoids (C4–C8). C15H20O5 Oil (tri-Ac), [α]D25 = −28° (c = 0.31, CHCl3) (tri-Ac). Source: Marine-derived fungus Emericella variecolor. Pharm: Antimicrobial. Ref: J. Malmstrøm, et al, JNP, 2002, 65, 364│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) O

OH

OH

O

H

OH

360 Ayamycin Type: Nitrobenzene derivatives. C14H17Cl2NO3 Cryst., mp 115–117 °C. Source: Marine-derived bacterium Nocardia sp. ALAA 2000. Pharm: Antibacterial (grampositive and -negative bacteria, MIC = 0.1 μg/mL). Ref: M. M. A. El-Gendy, et al,

112

2 Aromatic Metabolites

J. Antibiot. (Tokyo) 2008, 61, 149│M. M. A. El-Gendy, et al, J. Antibiot., 2008, 61, 379│A. M. S. Mayer, et al, Comparative Biochemistry and Physiology, Part C 153, 2011, 191 (rev) Cl Cl O

O N O

361 Bromochlorogentisylquinone A Type: Benzoquinone derivatives. C7H4BrClO3 Yellow solid. Source: Marine-derived fungus Phoma herbarum from red alga Gloiopeitis tenax (addition of halide salts to fermentation medium, Cheokpo, Tongnyeong, R. O. Korea). Pharm: Antioxidant (DPPH scavenger, IC50 = 3.8 μmol/L, control L-Ascorbic acid, IC50 = 20 μmol/L). Ref: V. N. Nenkep, et al, J. Antibiot., 2010, 63, 199 O Cl

OH Br O

362 Bromochlorogentisylquinone B Type: Benzoquinone derivatives. C7H4BrClO3 Yellow solid. Source: Marine-derived fungus Phoma herbarum from red alga Gloiopeitis tenax (addition of halide salts to fermentation medium, Cheokpo, Tongnyeong, R. O. Korea). Pharm: Antioxidant (DPPH scavenger, IC50 = 3.9 μmol/L, control L-Ascorbic acid, IC50 = 20 μmol/L). Ref: V. N. Nenkep, et al, J. Antibiot., 2010, 63, 199 O Cl

OH

Br O

363 Chlorogentisylquinone Type: Benzoquinone derivatives. C7H5ClO3 Brown needles. Source: An unidentified marine-derived fungus. Pharm: Sphingomyelinase inhibitor (rat brain membrane). Ref: R. Uchida, et al, J. Antibiot., 2001, 54, 882

2.1 Simple Benzene Derivatives

OH

113

O Cl

O

364 Coenzyme Q9 Ubiquinone 45 Type: Benzoquinone derivatives. C54H82O4 Orange cryst. (EtOH), mp 45.2 °C. Source: Marine-derived actinomycete Nocardia sp. KMM 3749 (psychrophilic, cold water, expedition in Kuril and Simushir Is., Sea of Okhotsk). Pharm: Cytotoxic (mouse erythrocytes, MIC = 30–50 μg/mL; fertilized eggs of sea urchin Strongylocentrotus intermedius, MIC = 40 μg/mL). Ref: T. A. Kuznetsova, et al, Russ. Chem. Bull., 2002, 51, 1951│M.D. Lebar, et al, NPR, 2007, 24, 774 (rev)│CRC Press, DNP on DVD, 2012, version 20.2 O O O O

365 2,6-Dimethoxy-1,4-benzoquinone Type: Benzoquinone derivatives. C8H8O4 Yellow cryst. (AcOH), mp 256 °C, bp 311.1 °C Source: Marine-derived bacterium Salegentibacter sp. T436; marine-derived fungus Dendryphiella salina (grown on waste sulfite liquor), mangrove Bruguiera sexangula var. rhynchopetala. Pharm: Antibacterial; causes dermatitis; mutagenic. Ref: S. Bao, et al, Helv. Chim. Acta, 2005, 88, 2757│I. Schuhmann, et al, J. Antibiot., 2009, 62, 453 O O

O

O

366 2-(1,1-Dimethyl-2-propenyl)-5-(3-methyl-2-butenyl)-1,4-benzoquinone Type: Benzoquinone derivatives. C16H20O2 Yellow cryst. (petrol), mp 27.5–29 °C. Source: Brown algae Sporochnus comosus (Shaw I., Queensland, Australia) and Perithalia capillaris. Pharm: Cytotoxic (SF268, GI50 = 17 μmol/L; MCF7, GI50 = 26 μmol/L; H460, GI50 = 41 μmol/L; HT29, GI50 = 37 μmol/L; CHO-K1, GI50 = 29 μmol/L); anti-inflammatory (hmn neutrophil free radical release inhibition in vitro,

114

2 Aromatic Metabolites

IC50 = 2.1 μmol/L, MMOA: superoxide anion inhibition). Ref: S. P. B. Ovenden, et al, JNP, 2011, 74, 739│C. E. Sansom, et al, JNP 2007, 70, 2042 O

O

367 Glabruquinone A Desmethylubiquinone Q2 Type: Benzoquinone derivatives. C18H24O4 Yellow oil. Source: Ascidian Aplidium glabrum (psychrophilic, cold water). Pharm: Cancer-preventive activity (anchorage-independent transformation assay, mouse JB6 P+ CI41 cells that had been transformed with an epidermal growth factor); cytotoxic (HCT116, IC50 = 12.7 μmol/L; MEL28, IC50 = 17.5 μmol/L; HT460, IC50 = 50.5 μmol/L); contact allergen. Ref: L. K. Shubina, et al, Tet. Lett., 2005, 46, 559│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) O

1'

O

O O

368 2-Hydroxy-3,6-dimethyl-5-(1-oxo-4-hexenyl)-1,4-benzoquinone Type: Benzoquinone derivatives. C14H16O4 Orange needles, mp 127–129 °C. Source: Marine-derived fungus Penicillium terrestre. Pharm: Cytotoxic (MTT method, P388 and A549). Ref: W. Liu, et al, J. Antibiot., 2005, 58, 441│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) O

O

HO O

369 2-Hydroxy-3,5-dimethyl-6-(2-oxopropyl)-1,4-benzoquinone Type: Benzoquinone derivatives. C11H12O4 Orange needles, mp 118 °C (dec). Source: Marine-derived fungus Penicillium terrestre. Pharm: Cytotoxic (MTT method, P388 and A549). Ref: W. Liu, et al, J. Antibiot., 2005, 58, 441│M. Saleem, et al, NPR, 2007, 24, 1142 (rev)

2.1 Simple Benzene Derivatives

115

O O HO O

370 Ilimaquinone Type: Benzoquinone derivatives. C22H30O4 Cryst. (hexane), mp 113–114 °C, [α]D23 = −23.2° (c = 1.12, CHCl3). Source: Sponges Hippospongia sp. (Palau, Oceania), Spongia sp. (Australia), Hippospongia metachromia, Smenospongia spp., Polyfibrospongia australis, Hyat spp., Dactylospongia elegans and Petrosaspongia metachromia. Pharm: Cytotoxic (differentiation-inducing activity to K562 cells into erythroblast, lowest effective concentration = 15 μmol/L); cytotoxic (NCI-H460, HepG2, SF268, MCF7, HeLa, and HL60 hmn tumor cell lines, inhibitory effects on maturation of starfish oocytes, and cell cycle arrest in HepG2 cell line were evaluated); cytotoxic (SF268, GI50 = 2.7 μmol/L; MCF7, GI50 = 3.9 μmol/L; H460, GI50 = 1.8 μmol/L; HT29, GI50 = 5.4 μmol/L; CHO-K1, GI50 = 2.0 μmol/L); antistaphylococcal; HIV reverse transcriptase inhibitor; anti-HIV; induces vesiculation of Golgi membranes. Ref: R. T. Luibrand, et al, Tetrahedron, 1979, 35, 609│R. J. Capon, et al, JOC, 1987, 52, 5059│S. Loya, Antimicrob. Agents Chemother., 1990, 34, 2009│P. A. Takizawa, et al, Cell (Cambridge, Mass.), 1993, 73, 1079│U. Acharya, et al, J. Cell Biol., 1995, 129, 577 │N. K. Utkina, et al, Tetrahedron Lett. 2003, 44, 101│S. Aoki, et al, CPB, 2004, 52, 935│H. Liu, et al, Pharm. Biol. 2006, 44, 522│M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev)│S. P. B. Ovenden, et al, JNP, 2011, 74, 65 O HO

O H

O 5

371 5-epi-Ilimaquinone Type: Benzoquinone derivatives. C22H30O4 [α]D = +29.8° (c = 0.4, CHCl3). Source: Sponges Hippospongia sp. (Palau, Oceania), Fenestraspongia sp., Dactylospongia elegans and Hyrtios sp. Pharm: Cytotoxic (P388, IC50 = 2.2 μg/mL; A549, IC50 = 0.9 μg/mL; HT29, IC50 = 3.4 μg/mL; B16-F-10, IC50 = 1.1 μg/mL); cytotoxic (NCI-H460, HepG2, SF268, MCF7, HeLa, and HL60 hmn tumor cell lines, inhibitory effects on maturation of starfish oocytes, and cell cycle arrest in HepG2 cell line were evaluated); cytotoxic (differentiation-inducing activity to K562 cells into erythroblast, lowest effective

116

2 Aromatic Metabolites

concentration = 15 μmol/L); toxic (brine shrimp Artemia larvae). Ref: B. Carté, et al, JOC, 1985, 50, 2785│J. Rodriguez, et al, Tetrahedron 1992, 48, 6667│S. Aoki, et al, CPB, 2004, 52, 935│H. Liu, et al, Pharm. Biol. 2006, 44, 522│M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O HO

O H

O 5

372 Longithorone A Type: Benzoquinone derivatives. C42H46O5 Cryst. (MeOH/CH2Cl2), mp 195–196 °C, [α]D = −87.5° (c = 2.7, CHCl3). Source: Ascidian Aplidium longithorax. Pharm: Cytotoxic (P388, ED50 = 10 μg/mL, weak). Ref: X. Fu, et al, JACS, 1994, 116, 12125 (erratum: 1995, 117, 9381) O

O

H O

H

O O

373 Sarcophytonone Type: Benzoquinone derivatives. C20H30O5 Yellow oil, [α]D25 = +5.8° (c = 0.4, CHCl3). Source: Soft coral Sarcophyton crassocaule (Lingshui Bay, Hainan), Pharm: Toxic (brine shrimp Artemia salina, mild). Ref: L. Li, et al, J. Asian Nat. Prod. Res., 2009, 11, 851 O

OH O O

O

374 Sargaquinoic acid Type: Benzoquinone derivatives. C27H36O4 Yellow oil. Source: Brown alga Sargassum serratifolium. Pharm: Nervous system activity (butyrylcholinesterase inhibitor,

2.2 Diaryl Derivatives

117

IC50 = 26 nmol/L); anticholinesterase activity of plastoquinones (lead compounds for Alzheimer’s disease therapy). Ref: T. Kusumi, et al, Chem. Lett., 1979, 277│B. W. Choi, et al, Phytother. Res. 2007, 21, 423 O

O

10'

OH 11'

O

375 Smenoquinone Type: Benzoquinone derivatives. C21H28O4 Cryst., mp 350 °C. Source: Sponge Smenospongia sp. Pharm: Cytotoxic (L1210 cell line, IC50 = 2.5 μg/mL). Ref: M. L. Kondracki, et al, Tetrahedron, 1989, 45, 1995│M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O HO

OH H

O 5

2.2 Diaryl Derivatives 376 Avrainvilleol Type: Diphenylmethanoids. C14H14Br2O4 Viscous oil. Source: Green alga Avrainvillea longicaulis. Pharm: Ichthyotoxin; IMP dehydrogenase inhibitor; antifeedant (reef fish); toxin. Ref: H. H. Sun, et al, Phytochemistry, 1983, 22, 743 OH Br

Br

OH

OH

OH

377 3-Bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)pyrocatechol Type: Diphenylmethanoids. C20H13Br5O6 Source: Red alga Rhodomela confervoides. Pharm: Hypoglycemic (PTP1B inhibitor) (PTP1B and hypoglycaemic effect in

118

2 Aromatic Metabolites

streptozotocin-induced diabetic Wistar rats, IC50 = 1.7 μmol/L). Ref: D. Shi, et al, Chin. Sci. Bull., 2008, 53, 2476 Br OH

Br

OH

Br Br

Br

HO

OH OH

OH

378 Isorawsonol Type: Diphenylmethanoids. C28H22Br4O7 Source: Green alga Avrainvillea rawsonii. Pharm: Mosine 5ʹ-monophosphate dehydrogenase inhibitor. Ref: J. L. Chen, et al, JNP, 1994, 57, 947 OH HO Br OH

HO

HO Br

Br OH

OH Br

379 Peniphenone C Type: Diphenylmethanoids. C18H18O6 Source: Marine fungus Penicillium dipodomyicola. Pharm: Antituberculosis (Mycobacterium tuberculosis, strongly inhibits mycobacterial Protein tyrosine phosphatase B, MptpB). Ref: H. Li, et al, JNP 2014, 77, 800 O OH

HO

O OH

O

380 Rawsonol Type: Diphenylmethanoids. C29H24Br4O7 Source: Green alga Avrainvillea rawsonii. Pharm: HMG-CoA reductase inhibitor (IC50 = 5 μmol/L, control fungal metabolite Mevinolin, (IC50 = 2 nmol/L)). Ref: B. K. Corte, et al, Phytochemistry, 1989, 28, 2917

2.2 Diaryl Derivatives

119

Br OH O OH Br

OH OH

OH Br

OH Br

381 Terrestrol A Type: Diphenylmethanoids. C22H22O7 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 33.3 μmol/L; Molt4, IC50 = 5.5 μmol/L; A549, IC50 = 23.5 μmol/L; Bel7402, IC50 = 57.0 μmol/L); antioxidant (DPPH scavenger, IC50 = 2.6 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH

OH

OH

O OH

OH

OH

382 Terrestrol F Type: Diphenylmethanoids. C14H13ClO5 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 55.0 μmol/L; Molt4, IC50 = 58.1 μmol/L; A549, IC50 = 13.8 μmol/L; Bel7402, IC50 = 63.2 μmol/L); antioxidant (DPPH scavenger, IC50 = 5.2 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH

OH

Cl OH

OH

OH

383 Terrestrol G Type: Diphenylmethanoids. C14H13ClO5 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 5.1 μmol/L; Molt4, IC50 = 6.5 μmol/L; A549, IC50 = 5.7 μmol/L; Bel7402, IC50 = 6.0 μmol/L); antioxidant (DPPH scavenger, IC50 = 4.1 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L); PTK (protein tyrosine kinases) inhibitor (Src, 10 μmol/L, InRt = 35.9%, control PP2, 1 μmol/L, InRt = 89.4%; KDR, 10 μmol/L,

120

2 Aromatic Metabolites

InRt = 31.8%, control SU11248, 10 μmol/L, InRt = 82.1%). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH

OH

OH Cl OH

OH

384 Terrestrol H Type: Diphenylmethanoids. C15H16O5 Brown gum. Source: Marine-derived fungus Penicillium terrestre (from sediment sample, China). Pharm: Cytotoxic (HL60, IC50 = 6.3 μmol/L; Molt4, IC50 = 5.8 μmol/L; A549, IC50 = 33.8 μmol/L; Bel7402, IC50 = 61.9 μmol/L); antioxidant (DPPH scavenger, IC50 = 6.3 μmol/L; control Ascorbis acid, IC50 = 17.4 μmol/L). Ref: L. Chen, et al, JNP, 2008, 71, 66 OH

OH

O OH

OH

385 2,2ʹ,3,3ʹ-Tetrabromo-4,4ʹ,5,5ʹ-tetrahydroxydiphenylmethane Type: Diphenylmethanoids. C13H8Br4O4 Cryst. (C6H6/MeOH), mp 200–201 °C. Source: Red algae Rhodomela larix and Rhodomela confervoides. Pharm: Hypoglycemic (PTP1B inhibitor) (PTP1B and hypoglycaemic effect in streptozotocin-induced diabetic Wistar rats, IC50 = 2.4 μmol/L). Ref: K. Kurata, et al, Chem. Lett., 1977, 1435│D. Shi, et al, Chin. Sci. Bull., 2008, 53, 2476 Br

Br

Br

Br

HO

OH OH

OH

386 Arugosin H Type: Benzophenonoids. C22H20O6 Bright orange solid. Source: Marine-derived fungus Emericella nidulans var. acristata from an unidentified green alga (Mediterranean Sea). Pharm: Antifungal (Mycotypha microspore, 50 μg/disk, IZD = 3 mm); antialgal (Chlorella fusca, 50 μg/disk, IZD = 2 mm). Ref: A. Kralj, et al, JNP, 2006, 69, 995

2.2 Diaryl Derivatives

121

O HO

O

OH

HO

HO

387 Isomonodictyphenone Type: Benzophenonoids. C15H12O6 Source: Mangrove-derived fungus Penicillium sp. MA-37 (rhizospheric soil). Pharm: Antibacterial (Aeromonas hydrophilia, MIC = 8 μg/mL, potent). Ref: H. Luo, et al, Phytochem. Lett., 2014, 9, 22│Y. Zhang, et al, JNP, 2012, 75, 1888 O

OH

O

OH

HO HO

388 Monodictyphenone Type: Benzophenonoids. C15H12O6 Yellow solid. Source: Marine-derived fungus Monodictys putredinis 187/195 15 I. Pharm: Cytochrome P450 1A inhibitor (50 μmol/L, InRt = 28%); inducer of NAD(P)H quinone reductase (Hepa1c1c7, CD > 50 μmol/L, IC50 > 50 μmol/L); aromatase Cyp1A inhibitor (50 μmol/L, InRt = 25%). Ref: A. Krick, et al, JNP, 2007, 70, 353 O

OH

OH

O

OH HO

389 2′,5′,6′,5,6-Pentabromo-3′,4′,3,4-tetramethoxybenzo-phenone Type: Benzophenonoids. C17H13Br5O5 Yellowish amorphous solid. Source: Red alga Laurencia similis. Pharm: Hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 2.66 μg/mL, control HD, IC50 = 0.80 μg/mL). Ref: J. Qin, et al, Bioorganic Med. Chem. Lett., 2010, 20, 7152 O

Br

O

O

O

O Br

Br Br

Br

122

2 Aromatic Metabolites

390 Pestalone Type: Benzophenonoids. C21H20Cl2O6 Yellow cryst., mp 153–155 °C. Source: Marinederived fungus Pestalotia sp. (cultured in presence of a bacterial antagonist) from brown alga Rosenvingea sp. (Bahamas). Pharm: Antibacterial (MRSA, MIC = 37 ng/mL; VREF, MIC = 78 ng/mL); cytotoxic. Ref: M. Cueto, et al, JNP, 2001, 64, 1444 O

H

O

OH Cl

HO

O OH

Cl

391 1,7-Dihydroxy-9-methyldibenzo[b,d] furan-3-carboxylic acid Type: Dibenzofurans. C14H10O5 Source: Sponge Acanthella cavernosa (Fiji). Pharm: Kinase EGFR inhibitor (100 μmol/L, InRt = 58.8%, control Genistein, InRt = 80%). Ref: M. E. Rateb, Bot. Mar. 2010, 53, 499│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH HO

OH O

O

392 3,9-Dimethyldibenzo[b,d]furan-1,7-diol Type: Dibenzofurans. C14H12O3 Source: Sponge Acanthella cavernosa (Fiji). Pharm: Kinase EGFR inhibitor (100 μmol/L, InRt = 32.5%, control Genistein, InRt = 80%). Ref: M. E. Rateb, Bot. Mar. 2010, 53, 499│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev) OH

OH O

393 3-(Hydroxymethyl)-9-methyldibenzo[b,d]furan-1,7-diol Type: Dibenzofurans. C14H12O4 Source: Sponge Acanthella cavernosa (Fiji). Pharm: Kinase EGFR inhibitor (100 μmol/L, InRt = 42.5%, control Genistein, InRt = 80%). Ref: M. E. Rateb, Bot. Mar. 2010, 53, 499│D. Skropeta, et al, Mar. Drugs, 2011, 9, 2131 (rev)

2.2 Diaryl Derivatives

123

OH HO OH O

394 Isopopopolohuanone E Type: Dibenzofurans. C42H54O6 Deep purple solid. Source: Sponge Dysidea sp. (New Zealand). Pharm: Cytotoxic (P388, IC50 = 25 μg/mL); antibacterial (Bacillus subtilis); antifungal (Trichophyton mentagrophytes). Ref: M. Stewart, et al, Aust. J. Chem., 1997, 50, 341 O HO

OH OH

O H

O H

395 5,5ʹ-diepi-Δ3,Δ3ʹ-Popolohuanone E Type: Dibenzofurans. C42H54O6 Deep purple amorph. solid. Source: Sponge Dysidea sp. (New Zealand). Pharm: Cytotoxic (P388, IC50 = 50 μg/mL); antibacterial (Bacillus subtilis); antifungal (Trichophyton mentagrophytes). Ref: M. Stewart, et al, Aust. J. Chem., 1997, 50, 341

4

3

5 H O O

HO

OH

OH H

3'

4'

O

5'

396 Popolohuanone E Type: Dibenzofurans. C42H54O6 Dark purple solid. Source: Sponge Dysidea sp. (Pohnpei I., Federated States of Micronesia). Pharm: Topoisomerase II inhibitor (with selective cytotoxicity against A549 non-small cell hmn lung cancer cell line).

124

2 Aromatic Metabolites

Ref: J. R. Carney, et al, Tet. Lett., 1993, 34, 3727│M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O

H

HO

HO

O

OH

H

O

397 Porric acid D Type: Dibenzofurans. C15H12O6 Source: Marine-derived fungus Alternaria sp. (Bohai Sea, Tianjin, China). Pharm: Antibacterial (Staphylococcus aureus, weak). Ref: X. Xu, et al, Chem. Nat. Compd., 2012, 47, 893 O

HO O HO

OH O

398 Cymobarbatol Type: Dibenzo[b,e]pyrans. C16H20Br2O2 Cryst., mp 166 °C, [α]D23 = −15.4°. Source: Green alga Cymopolia barbata. Pharm: Antimutagenic. Ref: M. E. Wall, et al, JNP, 1989, 52, 1092 Br

6

HO

7

O 9a

9

H

2

Br

399 Debromoisocymobarbatol Type: Dibenzo[b,e]pyrans. C16H21BrO2 Viscous oil. Source: Green alga Cymopolia barbata (Florida Keys, USA). Pharm: Antifeedant (fish). Ref: M. Park, et al, Phytochemistry, 1992, 31, 4115 Br

HO

O

H

2.2 Diaryl Derivatives

125

400 Isocymobarbatol Type: Dibenzo[b,e]pyrans. C16H20Br2O2 Cryst., mp 147 °C, [α]D23 = −51.4°. Source: Green alga Cymopolia barbata. Pharm: Antimutagenic. Ref: M. E. Wall, et al, JNP, 1989, 52, 1092 Br

O

HO

H

Br

401 Anomalin A 2,3,6,8-Tetrahydroxy-1-methylxanthone Type: Xanthone derivatives. C14H10O6 Yellowbrown powder. Source: Marine-derived fungus Arthrinium sp. from sponge Geodia cydonium (Adriatic Sea, Italy), marine fungi Apiospora montagnei and Wardomyces anomalus. Pharm: Protein kinases inhibitors (16 different protein kinases: AKT1, IC50 > 100 μmol/L; ALK, IC50 = 1.1 μmol/L; ARK5, IC50 = 15.6 μmol/L; Aurora-B, IC50 = 0.5 μmol/L; AXL, IC50 = 6.6 μmol/L; FAK, IC50 = 15.2 μmol/L; IGF1-R, IC50 = 8.6 μmol/L; MEK1 wt, IC50 > 100 μmol/L; MET wt, IC50 = 4.4 μmol/L; NEK2, IC50 = 83.9 μmol/L; NEK6, IC50 = 67.8 μmol/L; PIM1, IC50 = 0.3 μmol/L; PLK1, IC50 = 8.8 μmol/L; PRK1, IC50 = 45.3 μmol/L; SRC, IC50 = 12.9 μmol/L; VEGF-R2, IC50 = 0.8 μmol/L); cytotoxic (L5178Y, IC50 = 0.40 μmol/L, control Kahalalide F, IC50 = 4.30 μmol/L; K562, IC50 > 365 μmol/L, control Cisplatin (CDDP), IC50 = 7.80 μmol/L; A2780, IC50 = 4.34 μmol/L, Cisplatin (CDDP), IC50 = 0.80 μmol/L; A2780CisR, IC50 = 26.0 μmol/L, Cisplatin (CDDP), IC50 = 8.40 μmol/L); inhibits VEGF-A dependent endothelial cell sprouting (cellularangiogenesis assay, IC50 = 1.80 μmol/L, control Sunitinib, IC50 = 0.12 μmol/L); antioxidant (25.0 μg/mL, 94.7%). Ref: A. Abdel-Lateff, et al, JNP, 2003, 66, 706│M. Saleem, et al, NPR, 2007, 24, 1142 (rev)│S. S. Ebada, et al, BoMC, 2011, 19, 4644 OH

O OH

HO

O

OH

402 Antibiotic AGI-B4 Type: Xanthone derivatives. C16H14O7 Yellow powder, mp 166–168 °C, [α]D25 = −1.6° (c = 0.4, MeOH). Source: Marine-derive fungus Neosartorya fischeri 1008F1, terrestrial Aspergillus sp. Y80118. Pharm: Antiviral (TMV virus, IC50 = 260 μmol/L); inhibitor of VEGF-induced endothelial cell growth. Ref: H. S. Kim, et al, J. Antibiot., 2002, 55, 669│Q. -W. Tan, et al, Nat. Prod. Res., 2012, 26, 1402

126

2 Aromatic Metabolites

OH

O

O

O OH

HO

O

403 Aspergillusone B 1,2,8-Trihydroxy-6-(hydroxymethyl)-9-oxo-9H-xanthene-1-carboxylic acid methyl ester Type: Xanthone derivatives. C16H14O8 Source: Marine-derived fungus Aspergillus sydowii from gorgonian sea fan Annella sp. (Surat Thani Province, Thailand), deepsea fungus Engyodontium album DFFSCS021. Pharm: Antibacterial (Escherichia coli, 25 μg/disc, IZ = 11.0 mm, control PG, 10 μg/disc, IZ = 31.8 mm, MIC = 64.0 μg/mL, PG, MIC = 2.0 μg/mL; Bacillus subtilis, 25 μg/disc, IZ = 14.4 mm, control PG, 10 μg/disc, IZ = 43.3 mm, MIC = 64.0 μg/mL, PG, MIC = 2.0 μg/mL). Ref: K. Trisuwan, et al, JNP, 2011, 74, 1663│Q. Yao, et al, Mar. Drugs, 2014, 12, 5902 O

O

HO

O

OH

HO OH

O

404 Chaetoxanthone A Type: Xanthone derivatives. C20H18O7 Yellow solid, [α]D24 = −118° (c = 0.19, CHCl3). Source: Marine-derived fungus Chaetomium sp. from an unidentified alga (Greece waters). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense strain STIB 900, IC50 = 4.7 μg/mL, control Melarsoprol, IC50 = 0.004 μg/mL; Trypanosoma cruzi strain Tulahuen C4 IC50 > 10 μg/mL, control Benznidazole, IC50 = 0.317 μg/mL); antileishmanial (Leishmania donovani strain MHOM-ET-67/L82, IC50 = 5.3 μg/mL, control Miltefosine, IC50 = 0.125 μg/mL); antimalarial (Plasmodium falciparum strain K1, IC50 = 3.5 μg/mL, control Chloroquine, IC50 = 0.079 μg/mL); cytotoxic (L-6, IC50 = 59.1 μg/mL, control Podophyllotoxin, IC50 = 0.006 μg/mL). Ref: A. Pontius, et al, JNP, 2008, 71, 1579 O

O

OH

H OH O

O

O

405 Chaetoxanthone B Type: Xanthone derivatives. C20H18O6 Yellow solid, [α]D24 = +1.7° (c = 0.15, CHCl3). Source: Marine-derived fungus Chaetomium sp. from an unidentified alga (Greece waters). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense strain STIB 900, IC50 = 9.3 μg/mL, control Melarsoprol, IC50 = 0.004 μg/mL; Trypanosoma cruzi

2.2 Diaryl Derivatives

127

strain Tulahuen C4 IC50 = 7.1 μg/mL, control Benznidazole, IC50 = 0.317 μg/mL); antileishmanial (Leishmania donovani strain MHOM-ET-67/L82, IC50 = 3.4 μg/mL, control Miltefosine, IC50 = 0.125 μg/mL); antimalarial (Plasmodium falciparum strain K1, IC50 = 0.5 μg/mL, control Chloroquine, IC50 = 0.079 μg/mL); cytotoxic (L-6, IC50 > 90 μg/mL, control Podophyllotoxin, IC50 = 0.006 μg/mL). Ref: A. Pontius, et al, JNP, 2008, 71, 1579 O

O

H

OH

O O

O

406 Chaetoxanthone C Type: Xanthone derivatives. C20H19ClO6 Yellow solid, [α]D24 = +88° (c = 0.2, CHCl3). Source: Marine-derived fungus Chaetomium sp. from an unidentified alga (Greece waters). Pharm: Antitrypanosomal (Trypanosoma brucei rhodesiense strain STIB 900, IC50 = 42.6 μg/mL, control Melarsoprol, IC50 = 0.004 μg/mL; Trypanosoma cruzi strain Tulahuen C4 IC50 = 1.5 μg/mL, control Benznidazole, IC50 = 0.317 μg/mL); antileishmanial (Leishmania donovani strain MHOM-ET-67/L82, IC50 = 3.1 μg/mL, control Miltefosine, IC50 = 0.125 μg/mL); antimalarial (Plasmodium falciparum strain K1, IC50 = 4.0 μg/mL, control Chloroquine, IC50 = 0.079 μg/mL); cytotoxic (L-6, IC50 = 46.7 μg/mL, control Podophyllotoxin, IC50 = 0.006 μg/mL). Ref: A. Pontius, et al, JNP, 2008, 71, 1579 OH

O

O

O HO

O Cl

407 12-O-Deacetyl-phomoxanthone A Type: Xanthone derivatives. C36H36O15 Source: Mangrove-derived fungus Phomopsis sp. from mangrove Rhizophora mucronata (Muara Angke, Jakarta, Indonesia). Pharm: Antibacterial (several gram-positive bacteria, moderate). Ref: Y. Shiono, et al, Nat. Prod. Commun., 2013, 8, 1735 OH

O

OH

O

O O

O

O

O

HO

O O

OH

O

OH

128

2 Aromatic Metabolites

408 Deacetylphomoxanthone B Type: Xanthone derivatives. C34H34O14 Gum, [α]D26 = +106.8° (c = 0.01, CHCl3). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China, first time isolated as MNP), terrestrial fungus Phomopsis sp. PSU-D15. Pharm: Cytotoxic (MDA-MB-435, IC50 = (14.40 ± 1.18)μmol/L, control Epirubicin, IC50 = (0.56 ± 0.06)μmol/L; HCT116, IC50 = (7.12 ± 0.70)μmol/L, Epirubicin, IC50 = (0.48 ± 0.03)μmol/L; Calu3, IC50 = (4.14 ± 0.02)μmol/L, Epirubicin, IC50 = (1.03 ± 0.10)μmol/L; Huh7, IC50 = (29.20 ± 0.19)μmol/L, Epirubicin, IC50 = (0.96 ± 0.01)μmol/L; MCF-10A, IC50 > 50 μmol/L, Epirubicin, IC50 = (0.48 ± 0.08)μmol/L). Ref: V. Rukachaisirikul, et al, Phytochemistry, 2008, 69, 783│B. Ding, et al, Mar. Drugs, 2013, 11, 4961 OH

O O

O

OH O

O HO

OH

OH

O

O O

OH

409 Deacetyl-phomoxanthone C Type: Xanthone derivatives. C34H34O14 Yellow powder, mp 145.5–146.7 °C, [α]D25 = +101.6° (c = 0.44, MeOH). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China). Pharm: Cytotoxic (MDA-MB435, IC50 > 50 μmol/L; HCT116, IC50 = (44.06 ± 3.29)μmol/L, control Epirubicin, IC50 = (0.48 ± 0.03)μmol/L; Calu3, IC50 = (43.35 ± 2.09)μmol/L, Epirubicin, IC50 = (1.03 ± 0.10)μmol/L; Huh7, IC50 > 50 μmol/L; MCF-10A, IC50 > 50 μmol/L). Ref: B. Ding, et al, Mar. Drugs, 2013, 11, 4961 OH

O

OH

O O

OH

O

O

HO

O O

OH

O

OH

410 Dicerandrol A Type: Xanthone derivatives. C34H34O14 Amorph. yellow powder, [α]D25 = −50.9° (c = 0.1, CHCl3). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China, first time isolated as MNP), terrestrial fungus Phomopsis longicolla from Dicerandra frutescens (endangered). Pharm: Cytotoxic

2.2 Diaryl Derivatives

129

(MDA-MB-435, IC50 (3.03 ± 0.12)μmol/L, control Epirubicin, IC50 = (0.56 ± 0.06)μmol/L; HCT116, IC50 = (2.64 ± 0.03)μmol/L, Epirubicin, IC50 = (0.48 ± 0.03)μmol/L; Calu3, IC50 = (1.76 ± 0.02)μmol/L, Epirubicin, IC50 = (1.03 ± 0.10)μmol/L; Huh7, IC50 = (4.19 ± 0.08)μmol/L, Epirubicin, IC50 = (0.96 ± 0.01)μmol/L; MCF-10A, IC50 = (28.32 ± 3.57)μmol/L, Epirubicin, IC50 = (0.48 ± 0.08)μmol/L); antibacterial. Ref: M. M. Wagenaar et al, JNP, 2001, 64, 1006│B. Ding, et al, Mar. Drugs, 2013, 11, 4961 O O

OH O

OH

O

OH

OH

O

OH

O HO

O O

411 Dicerandrol B Type: Xanthone derivatives. C36H36O15 [α]D25 = −6.5° (c = 0.1, CHCl3). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China first time isolated as MNP), terrestrial fungus Phomopsis longicolla from Dicerandra frutescens (endangered). Pharm: Cytotoxic (MDA-MB435, IC50 = (8.65 ± 0.06)μmol/L, control Epirubicin, IC50 = (0.56 ± 0.06)μmol/L; HCT116, IC50 = (3.94 ± 0.39)μmol/L, Epirubicin, IC50 = (0.48 ± 0.03)μmol/L; Calu3, IC50 = (4.10 ± 0.08)μmol/L, Epirubicin, IC50 = (1.03 ± 0.10)μmol/L; Huh7, IC50 = (30.37 ± 1.10)μmol/L, Epirubicin, IC50 = (0.96 ± 0.01)μmol/L; MCF-10A, IC50 = (8.14 ± 1.27)μmol/L, Epirubicin, IC50 = (0.48 ± 0.08)μmol/L). Ref: M. M. Wagenaar et al, JNP, 2001, 64, 1006│B. Ding, et al, Mar. Drugs, 2013, 11, 4961 O O

OH O

OH

O

OH

OH

O

OH

O O

O O

O

130

2 Aromatic Metabolites

412 Dicerandrol C Type: Xanthone derivatives. C38H38O16 [α]D = +44.3° (c = 0.003, CHCl3). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China first time isolated as MNP), terrestrial fungus Phomopsis longicolla from Dicerandra frutescens (endangered). Pharm: Cytotoxic (MDA-MB435, IC50 = (44.10 ± 2.45)μmol/L, control Epirubicin, IC50 = (0.56 ± 0.06)μmol/L; HCT116, IC50 = (42.63 ± 2.90)μmol/L, Epirubicin, IC50 = (0.48 ± 0.03)μmol/L; Calu3, IC50 = (36.52 ± 0.32)μmol/L, Epirubicin, IC50 = (1.03 ± 0.10)μmol/L; Huh7, IC50 > 50 μmol/L, Epirubicin, IC50 = (0.96 ± 0.01)μmol/L; MCF-10A, IC50 = (33.05 ± 2.74)μmol/L, Epirubicin, IC50 = (0.48 ± 0.08)μmol/L). Ref: M. M. Wagenaar et al, JNP, 2001, 64, 1006│B. Ding, et al, Mar. Drugs, 2013, 11, 4961 O

O O

O

O

OH

O

OH

OH

O

OH

O O

O O

O

413 1,7-Dihydroxy-2-methoxy-3-(3-methylbut-2-enyl)-9H-xanthen- 9-one Type: Xanthone derivatives. C20H18O5 Yellow amorph. solid; mp 142–143 °C. Source: Mangrove-derived fungus Phomopsis sp. from mangrove Avicennia marina (Dong Zai, Hannan, China). Pharm: Cytotoxic (KB cell lines, IC50 = 20 μmol/L; KBV200 cell lines, IC50 = 30 μmol/L). Ref: Z. J. Huang, et al, Magn. Reson. Chem., 2010, 48, 80 O

OH

O OH

O

414 Dimethyl 8-methoxy-9-oxo-9H-xanthene-1,6-dicarboxylate Type: Xanthone derivatives. C18H14O7 Cryst., mp 188–189 °C. Source: Mangrovederived fungus Penicillium sp. F 32 (culture broth) from mangrove Acanthus ilicifolius (bark, China). Pharm: Antifungal (Fusarium oxysporum f. cubense, MIC = 12.5 μg/mL). Ref: C. Shao, et al, Magn. Reson. Chem., 2008, 46, 1066

2.2 Diaryl Derivatives

O

O

O

131

O

O

O O

415 Emerixanthone A Type: Xanthone derivatives. C25H27ClO6 Yellow needle crystals, [α] = −78.1° (c = 0.0031, CHCl3). Source: Deep-sea fungus Emericella sp. SCSIO 05240 (sediment sample, E120°0.975′ N19°0.664′, depth of 3258 m, open voyage to South China Sea, in August 2007). Pharm: Antibacterial (Escherichia coli ATCC 29922, Klebsiella pneumonia ATCC 13883, Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212, Acinetobacter baumannii ATCC 19606, and Aeromonas hydrophila ATCC 7966, all IZD = 4–6 mm, weak, control Ciprofloxacin, IZD = 35–40 mm). Ref: M. Fredimoses, et al, Mar. Drugs 2014, 12, 3190

OH

O

HO O

O

Cl

OH

416 Emerixanthone C Type: Xanthone derivatives. C27H32O7 Yellow needle crystals, [α] = −95.5° (c = 0.0018, CHCl3). Source: Deep-sea fungus Emericella sp. SCSIO 05240 (sediment sample, E120°0.975′ N19°0.664′, depth of 3258 m, open voyage to South China Sea, in August 2007). Pharm: Antibacterial (Escherichia coli ATCC 29922, Klebsiella pneumonia ATCC 13883, Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212, Acinetobacter baumannii ATCC 19606, and Aeromonas hydrophila ATCC 7966, all IZD = 4–6 mm, weak, control Ciprofloxacin, IZD = 35–40 mm). Ref: M. Fredimoses, et al, Mar. Drugs 2014, 12, 3190

132

2 Aromatic Metabolites

OH

O

HO O

O

O

O

417 Emerixanthone D Type: Xanthone derivatives. C27H30O8 Yellow needle crystals, [α] = −93.3° (c = 0.009, CHCl3). Source: Deep-sea fungus Emericella sp. SCSIO 05240 (sediment sample, E120°0.975′ N19°0.664′, depth of 3258 m, open voyage to South China Sea, in August 2007). Pharm: Antifungal (agricultural pathogens Fusarium sp., Penicillium sp., Aspergillus niger, Rhizoctonia solani, Fusariumoxy sporium f. sp. niveum, Fusariumoxy sporium f. sp. cucumeris, all IZD = 3–4 mm, mild, control Carbendazim, IZD = 40–45 mm). Ref: M. Fredimoses, et al, Mar. Drugs 2014, 12, 3190

OH

HO O O

O

OH

O O

418 Engyodontiumone B Type: Xanthone derivatives. C16H11ClO6 Yellow needles. Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 55.5 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 = 96.1 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 = 172.3 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 = 73.8 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O Cl

HO

O

2.2 Diaryl Derivatives

133

419 Engyodontiumone C Type: Xanthone derivatives. C16H14O7 Brown needles, [α]D25 = +5° (c = 0.5, MeOH). Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 218.4 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 > 300 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 > 300 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 > 300 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O OH

HO

O

420 Engyodontiumone D Type: Xanthone derivatives. C16H16O7 Brown needles [α]D25 = +14° (c = 0.3, MeOH). Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 208.6 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 > 300 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 > 300 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 > 300 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O OH

O

OH

421 (±)-Engyodontiumone E Type: Xanthone derivatives. C16H16O7 Brown needles [α]D25 = 0° (c = 0.4, MeOH). Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 15.9 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 = 205.2 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 > 300 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 > 300 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O OH

HO

O 1alpha,2beta 1beta,2alpha

134

2 Aromatic Metabolites

422 (±)-Engyodontiumone F Type: Xanthone derivatives. C16H16O8 Brown needles [α]D25 = 0° (c = 0.3, MeOH). Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 192.7 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 > 300 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 > 300 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 > 300 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O OH

HO

O

OH

1beta,2beta,3beta 1alpha,2alpha,3alpha

423 (±)-Engyodontiumone G Type: Xanthone derivatives. C16H16O8 Brown needles [α]D25 = 0° (c = 0.2, MeOH). Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 287.2 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 > 300 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 > 300 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 > 300 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O OH

HO

O

OH

1beta,2beta,3alpha 1alpha,2alpha,3beta

424 Engyodontiumone H Type: Xanthone derivatives. C16H14O7 Brown needles, [α]D25 = −56° (c = 1, MeOH). Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 4.9 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 = 24.8 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 = 38.5 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 = 60.5 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 = 53.3 μmol/L, DOX, IC50 = 1.2 μmol/L); antibacterial (Escherichia coli, 25 μg/disc, IZ = 13.8 mm, control PG, 10 μg/disc, IZ = 31.8 mm, MIC = 64.0 μg/mL, PG, MIC = 2.0 μg/mL; Bacillus subtilis, 25 μg/disc, IZ = 16.5 mm, control PG, 10 μg/disc, IZ = 43.3 mm, MIC = 32.0 μg/mL, PG, MIC = 2.0 μg/mL). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

2.2 Diaryl Derivatives

OH

O

O

135

O OH

HO

O

425 (2β)-Engyodontiumone H AGI-B4 Type: Xanthone derivatives. C16H14O7 Source: Deep-sea fungus Engyodontium album DFFSCS021. Pharm: Cytotoxic (U937, IC50 = 8.8 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 = 60.0 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 = 102.2 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 = 52.7 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 = 133.3 μmol/L, DOX, IC50 = 1.2 μmol/L); antibacterial (Escherichia coli, 25 μg/disc, IZ = 15.8 mm, control PG, 10 μg/disc, IZ = 31.8 mm, MIC = 64 μg/mL, PG, MIC = 2.0 μg/mL; Bacillus subtilis, 25 μg/disc, IZ = 17.5 mm, control PG, 10 μg/disc, IZ = 43.3 mm, MIC = 64 μg/mL, PG, MIC = 2.0 μg/mL). Ref: Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O OH

HO

O

426 globosuxanthone A Type: Xanthone derivatives. C15H12O7 Yellow cryst., mp 152 °C, [α]D25 = −50° (c = 1.2, MeOH/CHCl3), [α]D25 = −29° (c = 0.2, DMSO). Source: Marine-derived fungus Beauveria bassiana from an unidentified sponge (Iriomote I., Okinawa, Japan), an unidentified terrestrial plant. Pharm: Antineoplastic. Ref: H. Yamazaki, et al, Mar. Drugs, 2012, 10, 2691│E. M. K. Wijeratne, et al, BoMC, 2006, 14, 7917

OH

O O HO

O OH

O

427 Grisephenone A Type: Xanthone derivatives. C17H17ClO6 Source: Sponge-derived fungus Stachybotrys sp. HH1 ZSDS1F1-2. Pharm: Antiviral (Enterovirus-71, IC50 = 50.0 μmol/L). Ref: C. Qin, et al, J. Antibiot., 2014, 68, 121

136

2 Aromatic Metabolites

O

O

O

O

OH

OH Cl

428 1-Hydroxy-4,7-dimethoxy-6-(3-oxobutyl)-9H-xanthen-9-one Type: Xanthone derivatives. C20H18O6 Yellow semisolid. Source: Mangrove-derived fungus Phomopsis sp. from mangrove Avicennia marina (Dong Sai of South China Sea coast). Pharm: Cytotoxic (KB cell lines, IC50 = 35 μmol/L; KBV200 cell lines, IC50 = 41 μmol/L). Ref: Z. J. Huang, et al, Magn. Reson. Chem., 2010, 48, 80 O

O

OH

O O

O

429 8-Hydroxy-3-methyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether Type: Xanthone derivatives. C16H12O5 Yellow needles. Source: Two unidentified marine fungi (co-culture broth, E33 and K38). Pharm: Antifungal (five flimantous fungal strains, 100 μg/mL: Gloeasporium musae, InRt = 53%, Blumeria graminearum, InRt = 4.6%, Fusarium oxysporum, InRt = 9.5%, Perononphthora cichoralearum, InRt = 48%, Colletotrichum glocosporioides, InRt = 28%). Ref: C. Y. Li, et al, Chem. Nat. Compd., 2011, 47, 382│L. Xu, et al, Mar. Drugs, 2015, 13, 3479 (rev)

OH

O

O

O

O

430 JBIR 97 Type: Xanthone derivatives. C33H28O12 Yellow amorph. solid, [α]D25 = +316° (c = 0.1, MeOH). Source: Marine-derived fungus Tritirachium sp. from sponge Pseudoceratina purpurea (Sakuraguchi, Ishigaki I., Okinawa). Pharm: Cytotoxic (WST-8colorimetric assay, hmn cervical carcinomaHeLa, IC50 = 11 μmol/L; ACC-MESO-1, IC50 = 31 μmol/L). Ref: J. Ueda, et al, J. Antibiot., 2010, 63, 615

2.2 Diaryl Derivatives

OH

O

137

OH OH

O

OH

O

O

O

OH

O

O

431 JBIR 98 Type: Xanthone derivatives. C33H28O12 Yellow amorph. solid, [α]D25 = +229° (c = 0.1, MeOH). Source: Marine-derived fungus Tritirachium sp. from sponge Pseudoceratina purpurea (Sakuraguchi, Ishigaki I., Okinawa). Pharm: Cytotoxic (WST-8colorimetric assay, hmn cervical carcinoma HeLa, IC50 = 17 μmol/L; ACC-MESO-1, IC50 = 63 μmol/L). Ref: J. Ueda, et al, J. Antibiot., 2010, 63, 615 OH

O

OH OH

OH

O

O

O

isomer of JBIR 97

O

O

O

OH

432 JBIR 99 Type: Xanthone derivatives. C33H28O12 Yellow amorph. solid, [α]D25 = +333° (c = 0.1, MeOH). Source: Marine-derived fungus Tritirachium sp. from sponge Pseudoceratina purpurea (Sakuraguchi, Ishigaki I., Okinawa). Pharm: Cytotoxic (WST-8colorimetric assay, hmn cervical carcinomaHeLa, IC50 = 17 μmol/L; ACC-MESO-1, IC50 = 59 μmol/L). Ref: J. Ueda, et al, J. Antibiot., 2010, 63, 615 OH O O

OH

OH

O

O

OH O

O

OH

O

433 Monodictysin A 1,2,3,4,4a,9a-Hexahydro-1,3,4,8-tetrahydroxy-4a,6-dimethyl-9H-xanthen-9-one Type: Xanthone derivatives. C15H18O6 Yellow cryst., [α]D24 = +53° (c = 0.43, CHCl3). Source: Marine-derived fungus Monodictys putredinis 187/195 15 I. Pharm: Cytochrome P450 1A (CYP1A) inhibitor (IC50 ≥ 50 μmol/L, control α-Naphthoflavone,

138

2 Aromatic Metabolites

IC50 = 0.0035 μmol/L; 400 μmol/L without cytotoxicity); inducer of NAD(P)H quinone reductase (Hepa1c1c7, CD = 191.1 μmol/L, IC50 > 400 μmol/L); aromatase Cyp1A inhibitor (50 μmol/L, InRt = 32%). Ref: A. Krick, et al, JNP, 2007, 70, 353 OH

O

OH H 9a

1

6

O

OH OH

434 Monodictysin B 1,2,3,4,4a,9a-Hexahydro-1,4,8-trihydroxy-3,4a-dimethyl-9H-xanthen-9-one Type: Xanthone derivatives. C15H18O5 Amorph. solid, [α]D24 = +80.5° (c = 0.2, CHCl3). Source: Marine-derived fungus Monodictys putredinis 187/195 15 I. Pharm: Cytochrome P450 1A inhibitor (IC50 = 23.3 μmol/L, control α-Naphthoflavone, IC50 = 0.0035 μmol/L); inducer of NAD(P)H quinone reductase (Hepa1c1c7, CD = 12.0 μmol/L, IC50 > 50 μmol/L); aromatase Cyp1A inhibitor (50 μmol/L, InRt = 9%). Ref: A. Krick, et al, JNP, 2007, 70, 353 OH

O

OH H 9a

1

6

O OH

435 Monodictysin C Type: Xanthone derivatives. C16H20O6 Amorph. solid, [α]D24 = +102° (c = 0.5, CHCl3). Source: Marine-derived fungus Monodictys putredinis. Pharm: Cytochrome P450 1A inhibitor (IC50 = 3.0 μmol/L, control α-Naphthoflavone, IC50 = 0.0035 μmol/L); inducer of NAD(P)H quinone reductase (Hepa1c1c7, CD = 12.8 μmol/L, IC50 > 50 μmol/L); aromatase inhibitor (hmn recombinant aromatase (hmn Cyp 19 +P450 reductase supersomes) IC50 = 27 μmol/L, weak, control Ketokonazole, IC50 = 0.9 μmol/L); aromatase Cyp1A inhibitor (IC50 = 28.3 μmol/L, dose-dependent manner). Ref: A. Krick, et al, JNP, 2007, 70, 353 OH

O

OH H 9a

1

6

O

O OH

2.2 Diaryl Derivatives

139

436 Monodictyxanthone Type: Xanthone derivatives. C15H10O5 Yellow solid. Source: Marine-derived fungus Monodictys putredinis 187/195 15 I. Pharm: Cytochrome P450 1A inhibitor (IC50 = 34.8 μmol/L); inducer of NAD(P)H quinone reductase (Hepa1c1c7, CD > 50 μmol/L, IC50 > 50 μmol/L); aromatase Cyp1A inhibitor (50 μmol/L, InRt = 37%). Ref: A. Krick, et al, JNP, 2007, 70, 353

OH

O

OH

O

O

437 Norlichexanthone 3,6,8-Trihydroxy-1-methylxanthone Type: Xanthone derivatives. C14H10O5 Yellow prisms (EtOH aq or Et2O), mp 285–290 °C, mp 274–275 °C. Source: Marine-derived fungus Arthrinium sp. from sponge Geodia cydonium (Adriatic Sea, Italy), marinederived fungus Wardomyces anomalus, sponge-derived fungus Stachybotrys sp. HH1 ZSDS1F1-2 (Qin, 2014). Pharm: Protein kinases inhibitors (16 different protein kinases: AKT1, IC50 > 100 μmol/L; ALK, IC50 = 41.3 μmol/L; ARK5, IC50 = 33.0 μmol/L; Aurora-B, IC50 = 3.0 μmol/L; AXL, IC50 > 100 μmol/L; FAK, IC50 > 100 μmol/L; IGF1-R, IC50 = 33.3 μmol/L; MEK1 wt, IC50 > 100 μmol/L; MET wt, IC50 > 100 μmol/L; NEK2, IC50 > 100 μmol/L; NEK6, IC50 > 100 μmol/L; PIM1, IC50 = 0.3 μmol/L; PLK1, IC50 = 75.7 μmol/L; PRK1, IC50 = 54.9 μmol/L; SRC, IC50 = 35.0 μmol/L; VEGF-R2, IC50 = 11.7 μmol/L); cytotoxic (L5178Y, IC50 = 1.16 μmol/L, control Kahalalide F, IC50 = 4.30 μmol/L; K562, IC50 = 253.50 μmol/L, control Cisplatin (CDDP), IC50 = 7.80 μmol/L; A2780, IC50 = 68.2 μmol/L, Cisplatin (CDDP), IC50 = 0.80 μmol/L; A2780CisR, IC50 = 74.0 μmol/L, Cisplatin (CDDP), IC50 = 8.40 μmol/L); active against Clostridium welchii; mycotoxin; antiviral (Enterovirus-71, IC50 = 40.3 μmol/L) (Qin, 2014). Ref: A. Abdel-Lateff, et al, JNP, 2003, 66, 706│S. S. Ebada, et al, BoMC, 2011, 19, 4644│C. Qin, et al, J. Antibiot., 2014, 68, 121 O

HO

O

OH

OH

438 Oxisterigmatocystin A Type: Xanthone derivatives. C20H18O8 Source: Deep-sea fungus Aspergillus versicolor. Pharm: Cytotoxic (A549 and HL60). Ref: S. Cai, et al, J. Antibiot. 2011, 64, 193

140

2 Aromatic Metabolites

O O H

O

H O

O

OH

O

O

439 Oxisterigmatocystin B Type: Xanthone derivatives. C20H18O8 Source: Deep-sea fungus Aspergillus versicolor. Pharm: Cytotoxic (A549 and HL60). Ref: S. Cai, et al, J. Antibiot. 2011, 64, 193 O O H

O

H O

O

OH

O

O

440 Oxisterigmatocystin C Type: Xanthone derivatives. C19H16O7 Source: Deep-sea fungus Aspergillus versicolor. Pharm: Cytotoxic (A549 and HL60). Ref: S. Cai, et al, J. Antibiot. 2011, 64, 193 O O H H O

O

OH

O

O

441 Paeciloxanthone Type: Xanthone derivatives. C20H20O4 Amorph. yellow solid, mp 137 °C. Source: Mangrove-derived fungus Paecilomyces sp. Tree1-7 from an unidentified mangrove (bark, Taiwan waters). Pharm: Cytotoxic (HepG2, IC50 = 1.08 μg/mL; antifungal (Curvularia lunata and Candida albicans); AChE inhibitor (IC50 = 2.25 μg/mL); antibacterial (standard disk assay, 40 μg/mL, Escherichia coli, IZD = 12 mm); antifungal (standard disk assay, 40 μg/mL, Curvularia lunata, IZD = 6 mm; Candida albicans, IZD = 10 mm). Ref: L. Wen, et al, J. Asian Nat. Prod. Res., 2008, 10, 133

2.2 Diaryl Derivatives

OH

141

OH

O

O

442 Penexanthone A Type: Xanthone derivatives. C36H36O15 Yellow powder, [α]D23 = −36° (c = 0.1, MeOH). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China, first time isolated as MNP), terrestrial fungus Penicillium sp. (Costa Rican rainforest). Pharm: Cytotoxic (Myeloma: Dox40, no stromal cell IC50 = 15 μmol/L, with stromal cell IC50 = 21.6 μmol/L; H929, no stromal IC50 = 54.5 μmol/L, with stromal cell IC50 = 35.2 μmol/L; KMS34, no stromal IC50 = 22.6 μmol/L, with stromal cell IC50 = 55.6 μmol/L; L363, no stromal IC50 = 66.0 μmol/L, with stromal cell IC50 = 79.4 μmol/L; MM1S, no stromal IC50 = 37.1 μmol/L, with stromal cell IC50 = 47.1 μmol/L; OCIMY5, no stromal IC50 = 18.8 μmol/L, with stromal cell IC50 = 47.7 μmol/L; OPM2, no stromal IC50 = 12.7 μmol/L, with stromal cell IC50 = 10.5 μmol/L; RPMI8226, no stromal IC50 = 12.9 μmol/L, with stromal cell IC50 = 8.9 μmol/L; Lymphoma: Farage, no stromal IC50 = 12.4 μmol/L, with stromal cell IC50 = 10.5 μmol/L; HT, no stromal IC50 = 10.8 μmol/L, with stromal cell IC50 = 9.9 μmol/L; OCILY17R, no stromal IC50 = 31.1 μmol/L, with stromal cell IC50 = 47.4 μmol/L; Leukemia: KU812F, no stromal IC50 = 14.6 μmol/L, with stromal cell IC50 = 24.2 μmol/L; Breast: MDA-MB-231, no stromal IC50 = 43.4 μmol/L, with stromal cell IC50 = 34.2 μmol/L; Prostate: PC3, no stromal IC50 = 122.3 μmol/L, with stromal cell IC50 = 66.3 μmol/L) (Cao, 2012); cytotoxic (MDA-MB-435, IC50 = (7.90 ± 0.58)μmol/L, control Epirubicin, IC50 = (0.56 ± 0.06)μmol/L; HCT116, IC50 = (6.92 ± 0.38)μmol/L, Epirubicin, IC50 = (0.48 ± 0.03)μmol/L; Calu3, IC50 = (6.44 ± 0.86)μmol/L, Epirubicin, IC50 = (1.03 ± 0.10)μmol/L; Huh7, IC50 = (42.84 ± 3.58)μmol/L, Epirubicin, IC50 = (0.96 ± 0.01)μmol/L; MCF-10A, IC50 = (16.13 ± 1.57)μmol/L, Epirubicin, IC50 = (0.48 ± 0.08)μmol/L); (Ding, 2013). Ref: S. Cao, et al, JNP, 2012, 75, 793│B. Ding, et al, Mar. Drugs, 2013, 11, 4961 O

O O

O

OH O

O O

O

OH O

OH

O

OH OH

142

2 Aromatic Metabolites

443 Phomolactonexanthone A Type: Xanthone derivatives. C34H34O14 Yellow powder, mp 102.1–103.2 °C, [α]D25 = −75° (c = 0.2, MeOH). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China). Pharm: Cytotoxic (MDA-MB-435, IC50 > 50 μmol/L; HCT116, IC50 > 50 μmol/L; Calu3, IC50 = (43.45 ± 2.51)μmol/L, control Epirubicin, IC50 = (1.03 ± 0.10)μmol/L; Huh7, IC50 > 50 μmol/L; MCF-10A, IC50 > 50 μmol/L). Ref: B. Ding, et al, Mar. Drugs, 2013, 11, 4961 HO

OH

O

OH

O O

O O

HO

O

O O

O O

444 Phomolactonexanthone B Type: Xanthone derivatives. C34H34O14 Yellow powder, mp 101.6–102.4 °C, [α]D25 = −21.7° (c = 0.6, MeOH). Source: Mangrove-derived fungus Phomopsis sp. from mangrove Acanthus ilicifolius (branch, Hainan, China). Pharm: Cytotoxic (MDA-MB-435, HCT116, Calu3, Huh7, and MCF-10A, all IC50 > 50 μmol/L). Ref: B. Ding, et al, Mar. Drugs, 2013, 11, 4961 O O O

O

O

O

OH

OH

O

OH

O HO

O O

445 Stachybogrisephenone B Type: Xanthone derivatives. C16H15ClO6 Source: Sponge-derived fungus Stachybotrys sp. HH1 ZSDS1F1-2. Pharm: Antiviral (Enterovirus-71, IC50 = 30.1 μmol/L). Ref: C. Qin, et al, J. Antibiot., 2014, 68, 121 OH

O

O

OH Cl

OH

O

2.2 Diaryl Derivatives

143

446 Sydowinin A Type: Xanthone derivatives. C16H12O6 Yellow needles (Me2CO), mp 218–220 °C. Source: Deep-sea fungus Engyodontium album DFFSCS021, fungus Aspergillus sydowi. Pharm: Cytotoxic (U937, IC50 = 75.6 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 > 300 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 > 300 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 > 300 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: T. Hamasaki, et al, Agric. Biol. Chem., 1975, 39, 2337; 2341│Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

HO

O

O

O

447 Sydowinin B Antibiotic MS 347B Type: Xanthone derivatives. C16H12O7 Yellow needles (Me2CO), mp 220 °C (dec). Source: Deep-sea fungus Engyodontium album DFFSCS021, fungi Aspergillus sydowi and Aspergillus sp. KY52178. Pharm: Cytotoxic (U937, IC50 = 127.0 μmol/L, control DOX, IC50 = 0.06 μmol/L; HeLa, IC50 > 300 μmol/L, DOX, IC50 = 0.8 μmol/L; MCF7, IC50 > 300 μmol/L, DOX, IC50 = 23.1 μmol/L; HepG2, IC50 > 300 μmol/L, DOX, IC50 = 3.3 μmol/L; Huh7, IC50 > 300 μmol/L, DOX, IC50 = 1.2 μmol/L). Ref: T. Hamasaki, et al, Agric. Biol. Chem., 1975, 39, 2337; 1973, 2341│S. Nakanishi, et al, J. Antibiot., 1993, 46, 1775│Q. Yao, et al, Mar. Drugs, 2014, 12, 5902

OH

O

O

O OH

HO

O

448 TAN-931 Type: Xanthone derivatives. C15H10O7 Source: Acid-tolerant fungus Penicillium purpurogenum JS03-21 (region of red soil by Lujiang River, Yunnan, China). Pharm: Antiviral (IFV virus, IC50 = 58.6 μmol/L). Ref: H. Wang, et al, JNP, 2011, 74, 2014 O

HO

H

O

OH HO O

OH

144

2 Aromatic Metabolites

449 Varixanthone Type: Xanthone derivatives. C26H28O8 Yellow needles, mp 125–127 °C, [α]D25 = +62.1° (c = 1.13, CHCl3). Source: Marine-derived fungus Emericella variecolor M75-2. Pharm: Antibacterial (Escherichia coli, Bacillus subtilis, and Staphylococcus aureus, MIC = 12.5 μg/mL; Enterococcus faecalis, MIC = 50 μg/mL). Ref: J. Malmstrom, et al, JNP, 2002, 65, 364│T. S. Bugni, et al, NPR, 2004, 21, 143 (rev)│M. Saleem, et al, NPR, 2007, 24, 1142 (rev)

O H

O

OH

O

O O OH

OH

450 Vinaxanthone Type: Xanthone derivatives. C28H16O14 Pale yellow cryst. +1/2H2O (EtOAc), mp 280 ° C. Source: Marine-derived fungus Penicillium glabrum. Pharm: Phospholipase C inhibitor; semaphorin inhibitor; CD-4-binding activity. Ref: K. Kumagai, et al, J. Antibiot., 2003, 56, 610

OH OH O O

OH

OH

O

O

O

O

HO

HO

O

O

451 Yicathin B Type: Xanthone derivatives. C16H12O6 Source: Marine-derived fungus Aspergillus wentii (endophytic) from red alga Gymnogongrus flabelliformis (Pingtan I., Fujian, China). Pharm: Antimicrobial. Ref: R. -R. Sun, et al, Magn. Reson. Chem., 2013, 51, 65

2.2 Diaryl Derivatives

O

O

O

145

OH

O O

452 Yicathin C Type: Xanthone derivatives. C15H10O6 Source: Marine-derived fungus Aspergillus wentii (endophytic) from red alga Gymnogongrus flabelliformis (Pingtan I., Fujian, China). Pharm: Antimicrobial. Ref: R. -R. Sun, et al, Magn. Reson. Chem., 2013, 51, 65 O

O

HO

OH

O O

453 Aquastatin A Type: Depsidones. C36H52O12 Powder. Source: Marine-derived fungus Cosmospora sp. SF-5060. Pharm: Mammalian adenosine triphosphatases inhibitor; protein tyrosine phosphatase 1B inhibitor; enoyl-ACP reductases inhibitor; antibacterial. Ref: K. Hamano, et al, J. Antibiot., 1993, 46, 1648│C. Seo, et al, BoMCL, 2009, 19, 6095│Y. -J. Kwon, et al, Biol. Pharm. Bull., 2009, 32, 2061 OH O HO HO

O

OH

OH

O

OH OH

O O

454 Arugosin A Type: Depsidones. C25H28O6 Yellow oil. Source: Marine-derived fungus Emericella nidulans var. acristata from an unidentified green alga (Mediterranean Sea). Pharm: Cytotoxic (in vitro survival and proliferation assay, panel of 36 hmn tumor cell lines, 10 μg/mL, 19% active in 7 out of 36 cell lines); antibacterial (Bacillus megaterium, mixture with Arugosin B, 50 μg/disk, IZD = 4 mm). Ref: N. Kawahara, et al, JCS Perkin I, 1988, 907│Kralj, et al, JNP, 2006, 69, 995

146

2 Aromatic Metabolites

OH O HO

O OH

O

455 Arugosin B Type: Depsidones. C25H28O6 Yellow oil. Source: Marine-derived fungus Emericella nidulans var. acristata from an unidentified green alga (Mediterranean Sea). Pharm: Cytotoxic (in vitro survival and proliferation assay, panel of 36 hmn tumor cell lines, 10 μg/mL, 19% active in 7 out of 36 cell lines); antibacterial (Bacillus megaterium, mixture with Arugosin A, 50 μg/disk, IZD = 4 mm). Ref: N. Kawahara, et al, JCS Perkin I, 1988, 907│Kralj, et al, JNP, 2006, 69, 995 OH

O

HO

O OH

O

456 Corynesidone A Type: Depsidones. C15H12O5 Solid, mp 235–237 °C. Source: Marine-derived fungus Corynespora cassiicola L36. Pharm: Aromatase inhibitor. Ref: P. Chomcheon, et al, Phytochemistry, 2009, 70, 407 O O OH O HO

457 9-Dehydroxyeurotinone 2,4,7-Trihydroxy-9-methyldibenz[b,e]oxepin-6(11H)-one Type: Depsidones. C15H12O5 White amorphous powder, [α]D25 = −30.8° (c = 0.13, MeOH). Source: Mangrovederived fungus Eurotium rubrum from semimangrove Hibiscus tiliaceus (Hainan, China). Pharm: Cytotoxic (SW1990, IC50 = 25 μg/mL). Ref: H. -J. Yan, et al, Helv. Chim. Acta, 2012, 95, 163

2.2 Diaryl Derivatives

147

HO

O

HO

OH

O

458 9-Dehydroxyeurotinone 2,4,7-Trihydroxy-9-methyldibenz[b,e]oxepin-6(11H)-one Type: Depsidones. C15H12O5 White amorphous powder. [α]D25 = −30.8° (c = 0.13, MeOH). Source: Marine-derived fungus Eurotium rubrum (endophytic). Pharm: Antibacterial (100 mg/ disk, Enterobacter coli, IZ = 7 mm). Ref: H. J. Yan, et al, Helv. Chim. Acta, 2012, 95, 163

HO

OH

O O

OH

459 Guisinol Type: Depsidones. C23H25ClO5 Yellowish oil. Source: Marine-derived fungus Emericella unguis (teleomorph of fungus Aspergillus unguis) from an unidentified mollusc and an unidentified jellyfish (Venezuela). Pharm: Antibacterial (Staphylococcus aureus, 5 mg/mL DMSO, 15 μl added to a 4 mm well, mild). Ref: J. Nielsen, et al, Phytochemistry, 1999, 50, 263│T. S. Bugni, et al, NPR, 2004, 21, 143 (rev)

OH OH

O O

HO Cl

460 2-O-Methyl-4-O-(a-D-ribofuranosyl)-9-deoxyeurotinone Type: Depsidones. C21H22O9 Source: Mangrove-derived fungus Eurotium rubrum from semimangrove Hibiscus tiliaceus (China waters). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: D. -L. Li, et al, J. Microbiol. Biotechnol., 2009, 19, 675

148

HO

2 Aromatic Metabolites

O

O

O

O O HO

OH OH

461 3ʹ-O-Methyldehydroisopenicillide Antibiotic MC 142 Type: Depsidones. C22H24O6 Pawder, [α]D = −25° (CHCl3), [α]D = +11.6° (c = 0.17, CHCl3). Source: Mangrove-derived fungus Penicillium sp. from mangrove Bruguiera gymnorrhiza (rhizospheric soil, shaken culture, Hainan, China). fungi Penicillium purpurogenum and Penicillium sp. Pharm: Antihyperlipidaemic. Ref: H. Kawamura, et al, Nat. Prod. Lett., 2000, 14, 477│Y. Zhang, et al, JNP, 2012, 75, 1888 O

O

O

O 1'

O HO

462 2-O-Methyl-9-deoxyeurotinone Type: Depsidones. C16H14O5 Amorph. powder. Source: Mangrove-derived fungus Eurotium rubrum from semimangrove Hibiscus tiliaceus (China waters). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: D. -L. Li, et al, J. Microbiol. Biotechnol., 2009, 19, 675 HO

O O

O

OH

463 Penicillide Type: Depsidones. C21H24O6 Amorph. powder, [α]D24 = +4.9° (c = 0.82, MeOH), [α]D = +21° (c = 1, MeOH). Source: Mangrove-derived fungus Penicillium sp. from mangrove Bruguiera gymnorrhiza (rhizospheric soil, shaken culture, Hainan, China). Pharm: Plant growth inhibitor. Ref: T. Sassa, et al, Tet. Lett., 1974, 3941│Y. Zhang, et al, JNP, 2012, 75, 1888

2.2 Diaryl Derivatives

O

149

O

O

HO

O HO

464 Spiromastixone A Type: Depsidones. C19H20O5 White powder, [α]D25 = +36° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 4 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 4 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 8 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O

H O OH

H O HO

H

H Type A

465 Spiromastixone B Type: Depsidones. C19H19ClO5 White powder, [α]D25 = +18° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 8 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 4 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 8 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021 O

H O OH

Cl O HO H Type A

H

150

2 Aromatic Metabolites

466 Spiromastixone C Type: Depsidones. C19H19ClO5 White powder, [α]D25 = +22° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 8 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 8 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 16 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL); antibacterial (MSSA ATCC 29213, IC50 = 32 μmol/L, control Levofloxacin, IC50 = 0.25 μmol/L; MRSA ATCC 33591, IC50 = 64 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSA 15, IC50 = 64 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; MSSA 12-28, IC50 = 64 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSA 12-33, IC50 = 64 μmol/L, Levofloxacin, IC50 = 64 μmol/L; MSSE ATCC 12228, IC50 = 64 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSE12-6, IC50 = 64 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSE12-8, IC50 = 32 μmol/L, Levofloxacin, IC50 = 4 μmol/L; VSE ATCC 29212, IC50 = 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE ATCC 51299, IC50 > 256 μmol/ L, Levofloxacin, IC50 = 1 μmol/L; VSE 12-5, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE 09-9, IC50 = 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; VRE ATCC 700221, IC50 > 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-1, IC50 = 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-3, IC50 > 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; ESBLs(−) ATCC 25922, IC50 > 256 μmol/L, Levofloxacin, IC50 ≤ 0.03 μmol/L; ESBLs(−) 1515, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(−) 12-14, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(+) 12-15, IC50 > 256 μmol/L, Levofloxacin, IC50 = 32 μmol/L; ESBLs(+) ATCC 700603, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(−) 7, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; NDM-1(+) ATCC BAA-2146, IC50 > 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; ESBLs(−) 12-4, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(+) 12-8, IC50 > 256 μmol/L, Levofloxacin, IC50 = 16 μmol/L). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O

H O OH

H O

H

HO Cl Type A

467 Spiromastixone D Type: Depsidones. C19H18Cl2O5 White powder, [α]D25 = +45° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus

2.2 Diaryl Derivatives

151

aureus ATCC 29213, MIC = 2 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O

H O OH

H O HO

Cl

Cl Type A

468 Spiromastixone E Type: Depsidones. C19H18Cl2O5 White powder, [α]D25 = +18° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 4 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 4 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL); antibacterial (MSSA ATCC 29213, IC50 = 64 μmol/L, control Levofloxacin, IC50 = 0.25 μmol/L; MRSA ATCC 33591, IC50 = 32 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSA 15, IC50 = 64 μmol/ L, Levofloxacin, IC50 = 0.125 μmol/L; MSSA 12-28, IC50 = 128 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSA 12-33, IC50 = 128 μmol/L, Levofloxacin, IC50 = 64 μmol/L; MSSE ATCC 12228, IC50 = 32 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSE12-6, IC50 = 32 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSE12-8, IC50 = 64 μmol/L, Levofloxacin, IC50 = 4 μmol/L; VSE ATCC 29212, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE ATCC 51299, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VSE 12-5, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE 09-9, IC50 > 256 μmol/ L, Levofloxacin, IC50 > 128 μmol/L; VRE ATCC 700221, IC50 > 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-1, IC50 > 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-3, IC50 > 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; ESBLs (−) ATCC 25922, IC50 > 256 μmol/L, Levofloxacin, IC50 ≤ 0.03 μmol/L; ESBLs(−) 1515, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(−) 12-14, IC50 > 256 μmol/ L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(+) 12-15, IC50 > 256 μmol/L, Levofloxacin, IC50 = 32 μmol/L; ESBLs(+) ATCC 700603, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(−) 7, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; NDM-1(+) ATCC BAA-2146, IC50 > 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; ESBLs (−) 12-4, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(+) 12-8,

152

2 Aromatic Metabolites

IC50 > 256 μmol/L, Levofloxacin, IC50 = 16 μmol/L). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O

H O OH

Cl O HO

H

Cl Type A

469 Spiromastixone F Type: Depsidones. C19H17Cl3O5 White powder, [α]D25 = +31° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 2 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 1 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 0.5 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL); antibacterial (MSSA ATCC 29213, IC50 = 4 μmol/L, control Levofloxacin, IC50 = 0.25 μmol/L; MRSA ATCC 33591, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSA 15, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; MSSA 12-28, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/ L; MRSA 12-33, IC50 = 4 μmol/L, Levofloxacin, IC50 = 64 μmol/L; MSSE ATCC 12228, IC50 = 2 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSE12-6, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSE12-8, IC50 = 4 μmol/L, Levofloxacin, IC50 = 4 μmol/L; VSE ATCC 29212, IC50 = 32 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE ATCC 51299, IC50 = 32 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VSE 12-5, IC50 = 32 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE 09-9, IC50 = 32 μmol/L, Levofloxacin, IC50 > 128 μmol/L; VRE ATCC 700221, IC50 = 32 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-1, IC50 = 16 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-3, IC50 = 32 μmol/L, Levofloxacin, IC50 = 64 μmol/L; ESBLs(−) ATCC 25922, IC50 > 256 μmol/L, Levofloxacin, IC50 ≤ 0.03 μmol/L; ESBLs (−) 1515, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(−) 12-14, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(+) 12-15, IC50 > 256 μmol/ L, Levofloxacin, IC50 = 32 μmol/L; ESBLs(+) ATCC 700603, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(−) 7, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; NDM-1(+) ATCC BAA-2146, IC50 > 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; ESBLs(−) 12-4, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(+) 12-8, IC50 > 256 μmol/L, Levofloxacin, IC50 = 16 μmol/L). Ref: S. Niu, et al, JNP, 2014, 77, 1021

2.2 Diaryl Derivatives

O

153

H O OH

Cl O HO

Cl

Cl Type A

470 Spiromastixone G Type: Depsidones. C20H19Cl3O5 White powder, [α]D25 = +46° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 0.5 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 0.5 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 0.25 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL); antibacterial (MSSA ATCC 29213, IC50 = 8 μmol/L, control Levofloxacin, IC50 = 0.25 μmol/L; MRSA ATCC 33591, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSA 15, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; MSSA 12-28, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/ L; MRSA 12-33, IC50 = 8 μmol/L, Levofloxacin, IC50 = 64 μmol/L; MSSE ATCC 12228, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSE12-6, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSE12-8, IC50 = 2 μmol/L, Levofloxacin, IC50 = 4 μmol/L; VSE ATCC 29212, IC50 = 128 μmol/L, Levofloxacin, IC50 = 1 μmol/ L; VRE ATCC 51299, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VSE 12-5, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE 09-9, IC50 = 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; VRE ATCC 700221, IC50 = 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-1, IC50 = 16 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-3, IC50 = 256 μmol/L, Levofloxacin, IC50 = 64 μmol/L; ESBLs(−) ATCC 25922, IC50 > 256 μmol/L, Levofloxacin, IC50 ≤ 0.03 μmol/L; ESBLs(−) 1515, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(−) 12-14, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(+) 12-15, IC50 > 256 μmol/L, Levofloxacin, IC50 = 32 μmol/L; ESBLs(+) ATCC 700603, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(−) 7, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; NDM-1(+) ATCC BAA-2146, IC50 > 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; ESBLs(−) 12-4, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/ L; ESBLs(+) 12-8, IC50 > 256 μmol/L, Levofloxacin, IC50 = 16 μmol/L). Ref: S. Niu, et al, JNP, 2014, 77, 1021

154

2 Aromatic Metabolites

O

H O O

Cl O HO

Cl

Cl Type A

471 Spiromastixone H Type: Depsidones. C19H17Cl3O5 White powder, [α]D25 = +43° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 4 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 1 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 1 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL); antibacterial (MSSA ATCC 29213, IC50 = 4 μmol/L, control Levofloxacin, IC50 = 0.25 μmol/L; MRSA ATCC 33591, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSA 15, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; MSSA 12-28, IC50 = 8 μmol/L, Levofloxacin, IC50 = 0.25 μmol/ L; MRSA 12-33, IC50 = 8 μmol/L, Levofloxacin, IC50 = 64 μmol/L; MSSE ATCC 12228, IC50 = 16 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSE12-6, IC50 = 16 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSE12-8, IC50 = 4 μmol/L, Levofloxacin, IC50 = 4 μmol/L; VSE ATCC 29212, IC50 = 16 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE ATCC 51299, IC50 = 16 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VSE 12-5, IC50 = 16 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE 09-9, IC50 = 16 μmol/L, Levofloxacin, IC50 > 128 μmol/L; VRE ATCC 700221, IC50 = 16 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-1, IC50 = 16 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-3, IC50 = 32 μmol/L, Levofloxacin, IC50 = 64 μmol/L; ESBLs(−) ATCC 25922, IC50 = 64 μmol/L, Levofloxacin, IC50 ≤ 0.03 μmol/L; ESBLs(−) 1515, IC50 = 64 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(−) 12-14, IC50 = 64 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(+) 12-15, IC50 = 64 μmol/L, Levofloxacin, IC50 = 32 μmol/L; ESBLs(+) ATCC 700603, IC50 = 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(−) 7, IC50 = 256 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; NDM-1(+) ATCC BAA-2146, IC50 = 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; ESBLs(−) 12-4, IC50 = 128 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(+) 12-8, IC50 = 128 μmol/L, Levofloxacin, IC50 = 16 μmol/L). Ref: S. Niu, et al, JNP, 2014, 77, 1021

2.2 Diaryl Derivatives

O

155

Cl O OH

Cl O HO

H

Cl Type A

472 Spiromastixone I Type: Depsidones. C19H16Cl4O5 White powder, [α]D25 = +23° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 4 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL); antibacterial (MSSA ATCC 29213, IC50 = 16 μmol/L, control Levofloxacin, IC50 = 0.25 μmol/L; MRSA ATCC 33591, IC50 = 16 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSA 15, IC50 = 16 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; MSSA 12-28, IC50 = 16 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSA 12-33, IC50 = 32 μmol/L, Levofloxacin, IC50 = 64 μmol/L; MSSE ATCC 12228, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSE12-6, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSE12-8, IC50 = 8 μmol/L, Levofloxacin, IC50 = 4 μmol/L; VSE ATCC 29212, IC50 = 64 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE ATCC 51299, IC50 = 64 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VSE 12-5, IC50 = 64 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE 09-9, IC50 = 64 μmol/L, Levofloxacin, IC50 > 128 μmol/L; VRE ATCC 700221, IC50 = 64 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-1, IC50 = 64 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-3, IC50 = 64 μmol/L, Levofloxacin, IC50 = 64 μmol/L; ESBLs(−) ATCC 25922, IC50 > 256 μmol/L, Levofloxacin, IC50 ≤ 0.03 μmol/L; ESBLs(−) 1515, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(−) 12-14, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(+) 12-15, IC50 > 256 μmol/L, Levofloxacin, IC50 = 32 μmol/L; ESBLs(+) ATCC 700603, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(−) 7, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; NDM-1(+) ATCC BAA-2146, IC50 > 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; ESBLs(−) 12-4, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/ L; ESBLs(+) 12-8, IC50 > 256 μmol/L, Levofloxacin, IC50 = 16 μmol/L). Ref: S. Niu, et al, JNP, 2014, 77, 1021

156

2 Aromatic Metabolites

O

Cl O OH

Cl O HO

Cl

Cl Type A

473 Spiromastixone J Type: Depsidones. C20H18Cl4O5 White powder, [α]D25 = +33° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 0.125 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 0.25 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 0.125 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL); antibacterial (MSSA ATCC 29213, IC50 = 4 μmol/L, control Levofloxacin, IC50 = 0.25 μmol/L; MRSA ATCC 33591, IC50 = 2 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSA 15, IC50 = 2 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; MSSA 12-28, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSA 12-33, IC50 = 4 μmol/L, Levofloxacin, IC50 = 64 μmol/L; MSSE ATCC 12228, IC50 = 4 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MSSE12-6, IC50 = 2 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; MRSE12-8, IC50 = 1 μmol/L, Levofloxacin, IC50 = 4 μmol/L; VSE ATCC 29212, IC50 = 4 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE ATCC 51299, IC50 = 4 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VSE 12-5, IC50 = 4 μmol/L, Levofloxacin, IC50 = 1 μmol/L; VRE 09-9, IC50 = 4 μmol/L, Levofloxacin, IC50 > 128 μmol/L; VRE ATCC 700221, IC50 = 4 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-1, IC50 = 4 μmol/L, Levofloxacin, IC50 = 64 μmol/L; VRE 12-3, IC50 = 4 μmol/L, Levofloxacin, IC50 = 64 μmol/L; ESBLs(−) ATCC 25922, IC50 > 256 μmol/L, Levofloxacin, IC50 ≤ 0.03 μmol/L; ESBLs(−) 1515, IC50 > 256 μmol/ L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(−) 12-14, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(+) 12-15, IC50 > 256 μmol/L, Levofloxacin, IC50 = 32 μmol/L; ESBLs(+) ATCC 700603, IC50 > 256 μmol/L, Levofloxacin, IC50 = 1 μmol/L; ESBLs(−) 7, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.25 μmol/L; NDM-1(+) ATCC BAA-2146, IC50 > 256 μmol/L, Levofloxacin, IC50 > 128 μmol/L; ESBLs(−) 12-4, IC50 > 256 μmol/L, Levofloxacin, IC50 = 0.125 μmol/L; ESBLs(+) 128, IC50 > 256 μmol/L, Levofloxacin, IC50 = 16 μmol/L). Ref: S. Niu, et al, JNP, 2014, 77, 1021

2.2 Diaryl Derivatives

O

157

Cl O O

Cl O

Cl

HO Cl Type A

474 Spiromastixone K Type: Depsidones. C20H19Cl3O5 White powder, [α]D25 = +34° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 0.5 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 0.5 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 0.5 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O O Cl

Cl O

O

HO H

Cl Type B

475 Spiromastixone L Type: Depsidones. C20H18Cl4O5 White powder, [α]D25 = +36° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 0.25 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 0.5 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 0.25 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O O Cl

Cl O HO

Cl Type B

O Cl

158

2 Aromatic Metabolites

476 Spiromastixone M Type: Depsidones. C19H18Cl2O5 White powder, [α]D25 = +43° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 4 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O O H

Cl O HO

OH H

Cl Type B

477 Spiromastixone N Type: Depsidones. C19H17Cl3O5 White powder, [α]D25 = +48° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 1 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 1 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 0.5 μg/mL, Penicillin G, MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O O Cl

Cl O HO

Cl

OH H

Type B

478 Spiromastixone O Type: Depsidones. C19H16Cl4O5 White powder, [α]D25 = +36° (c = 0.05, MeOH). Source: Deep-sea fungus Spiromastix sp. (MCCC 3A00308, sediment, depth of 2869 m, South Atlantic Ocean GPS 13.7501W, 15.1668S). Pharm: Antibacterial (Staphylococcus aureus ATCC 29213, MIC = 4 μg/mL, control Penicillin G, MIC = 0.125 μg/mL; Bacillus thuringiensis SCSIO BT01, MIC = 2 μg/mL, Penicillin G, MIC = 128 μg/mL; Bacillus subtilis SCSIO BT01, MIC = 2 μg/mL, Penicillin G,

2.2 Diaryl Derivatives

159

MIC = 0.125 μg/mL; Escherichia coli ATCC 25922, MIC > 128 μg/mL, Penicillin G, MIC > 128 μg/mL). Ref: S. Niu, et al, JNP, 2014, 77, 1021

O O Cl

Cl O HO

OH Cl

Cl Type B

479 Stromemycin Type: Depsidones. C38H48O12 Amorph. red powder, mp 139 °C, [α]D20 = +29° (c = 0.1, EtOH). Source: Marine-derived fungus Emericella variecolor from sponge Haliclona valliculata. Pharm: Metalloproteinase inhibitor. Ref: Pat. Coop. Treaty (WIPO), 2001, 01 44 264; CA, 135, 60263d│G. Bringmann, et al, Phytochemistry, 2003, 63, 437

O OH

HO

O O

HO

HO O OH

HO OH

OH

480 7-O-Acetylsecopeni-cillide C Type: Simple biphenyl ethers. C22H24O7 Source: Mangrove-derived fungus Penicillium sp. MA-37 from mangrove rhizospheric soil. Pharm: Antibacterial (Micrococcus luteus, MIC = 64 μg/mL; Enterobacter coli, MIC = 16 μg/mL). Ref: Y. Zhang, et al, JNP, 2012, 75, 1888

O HO

O OH O HO

O

160

2 Aromatic Metabolites

481 Ambigol A 3′,4,5′,6-Tetrachloro-3-(2,4-dichlorophenoxy)-2,2′-biphenyldiol. Type: Simple biphenyl ethers. C18H8Cl6O3 Powder, mp 181.5–183.5 °C, [α]D = 0°. Source: Cyanobacterium Fischerella ambigua. Pharm: Molluscacidal (Biomphalaria glabrata); antibacterial (Micrococcus luteus ATCC 9341, Bacillus subtilis ATCC 6633, and Escherichia coli ATCC 25922.18); antifungal (P. oralicum CBS 219.30); cytotoxic (KB cells); toxic (brine shrimp Artemia salina). Ref: B. S. Falch, et al, JOC, 1993, 58, 6570│B. S. Falch, et al, Planta Med., 1995, 61, 321 Cl HO OH

Cl O

Cl

Cl

Cl

Cl

482 Ambigol B Type: Simple biphenyl ethers. C18H8Cl6O3 Pale yellow powder. Source: Cyanobacterium Fischerella ambigua. Pharm: Molluscacidal (Biomphalaria glabrata); antibacterial (Micrococcus luteus ATCC 9341, Bacillus subtilis ATCC 6633, and Escherichia coli ATCC 25922.18); antifungal (P. oralicum CBS 219.30); cytotoxic (KB cells); toxic (brine shrimp Artemia salina). Ref: B. S. Falch, et al, JOC, 1993, 58, 6570│B. S. Falch, et al, Planta Med., 1995, 61, 321 Cl

OH O

Cl

Cl O

Cl

Cl

Cl

483 Ambigol C Type: Simple biphenyl ethers. C18H8Cl6O3 Amorph. powder, mp 197 °C. Source: Cyanobacterium Fischerella ambigua. Pharm: Antiplasmodial (Plasmodium falciparum); antitrypanosomal (Trypanosoma brucei rhodesiense). Ref: G. M. König, et al, JNP, 2005, 68, 459 Cl

Cl O

O Cl

Cl

Cl

Cl

OH

484 Awajanoran Type: Simple biphenyl ethers. C19H22O4 Oil, [α]D25 = −21° (c = 0.1, MeOH). Source: Marine-derived fungus Acremonium sp. AWA16-1 (from sea mud sample, Japan

2.2 Diaryl Derivatives

161

waters). Pharm: Cytotoxic (A549, moderate); antibacterial (five different bacterial strains); antifungal (yeast Candida albicans). Ref: J. -H. Jang, et al, J. Antibiot., 2006, 59, 428 OH

OH O

O

485 2-(5-Bromo-2-methoxy-phenoxy)-3,5-dibromophenol Type: Simple biphenyl ethers. C13H9Br3O3 Source: Sponge Phyllospongia dendyi (Palau, Oceania). Pharm: Toxic (variety of micro- and macro-algae). Ref: T. Hattori, et al, Fish. Sci., 2001, 67, 899 OH

O O

Br

Br

Br

486 Chrysophaentin A Type: Simple biphenyl ethers. C32H24Cl4O8 Amorph. powder. Source: Brown alga Chrysophaeum taylorii. Pharm: Antibacterial (MRSA, MIC = 1.5 μg/mL, VREF, MIC = 2.9 μg/mL MMOA: inhibits GTPase activity of bacterial cell division protein FtsZ, FtsZ is a structural homolog of eukaryotic tubulin and, similar to tubulin, is a GTPase that polymerizes in a GTP-regulated manner). Ref: A. Plaza, et al, JACS, 2010, 132, 9069 HO

OH

O

Cl 2'

OH

Cl

Cl HO

HO 2

O Cl

OH

487 Chrysophaentin E Type: Simple biphenyl ethers. C32H26Cl4O6 Amorph. powder. Source: Brown alga Chrysophaeum taylorii. Pharm: Antibacterial. Ref: A. Plaza, et al, JACS, 2010, 132, 9069

162

2 Aromatic Metabolites

HO

OH

Cl

Cl

OH Cl

HO HO

O Cl

488 Chrysophaentin F Type: Simple biphenyl ethers. C32H24Cl4O8 Amorph. powder. Source: Brown alga Chrysophaeum taylorii. Pharm: Antibacterial. Ref: A. Plaza, et al, JACS, 2010, 132, 9069 Cl OH

2'

O

OH

OH Cl Cl HO

HO

2

Cl

12'

O OH

489 Cordyol C Type: Simple biphenyl ethers. C12H10O4 Source: Marine-derived fungus Aspergillus sydowii ZSDS1-F6. Pharm: Antiviral (H3N2 virus, IC50 = 78.5 μmol/L). Ref: J. -F. Wang, et al, J. Antibiot., 2014, 67, 581 OH HO

O

OH

490 Cordyol Cʹ 2,3,3′-Trihydroxy-5,5′-dimethyldiphenyl ether Type: Simple biphenyl ethers. C14H14O4 Amorph. powder. Source: Sponge-derived fungus Aspergillus sydowii ZSDS1-F6, deep-sea fungus Engyodontium album DFFSCS021, fungus Cordyceps sp. BCC1861. Pharm: Antiviral (IFV virus, IC50 = 78.5 μmol/L); antiviral (HSV-1 virus);

2.2 Diaryl Derivatives

163

antibacterial. Ref: T. Bunyapaiboonsri, et al, CPB, 2007, 55, 304│J. -F. Wang, et al, J. Antibiot., 2014, 67, 581│Q. Yao, et al, Mar. Drugs, 2014, 12, 5902 OH HO

OH

O

491 Cordyol E 3-O-Methyldiorcinol Type: Simple biphenyl ethers. C15H16O3 Source: Mangrovederived fungi Penicillium expansum from mangrove Excoecaria agallocha and Aspergillus sp. XS-20090066. Pharm: Antibacterial (Staphylococcus epidermidis, Staphylococcus aureus, Vibrio anguillarum, Vibrio parahemolyticus and Pseudomonas putida, MIC = 25.6–51.2 μmol/L). Ref: J. F. Wang, et al, Planta Med., 2012, 78, 1861│M. Chen, et al,. JNP, 2013, 76, 547

O

O

OH

492 2,3-Dibromo-5-chloro-6-(2,4-dibromophenoxy)phenol Type: Simple biphenyl ethers. C12H5Br4ClO2 Powder. Source: Sponge Dysidea granulosa (Milne Bay, Papua New Guinea). Pharm: Bcl-2 protein inhibitor (mild). Ref: L. Calcul, et al, JNP, 2009, 72, 443 Br

OH O

Br

Br

Cl

Br

493 3,5-Dibromo-2-(2,4-dibromophenoxy)-4-methoxyphenol Type: Simple biphenyl ethers. C13H8Br4O3 Green gum. Source: Sponge Dysidea granulosa (Milne Bay, Papua New Guinea). Pharm: Bcl-2 protein inhibitor (mild). Ref: L. Calcul, et al, JNP, 2009, 72, 443 Br

OH O

Br

Br

Br O

164

2 Aromatic Metabolites

494 4,6-Dibromo-2-(2ʹ-methoxy-4ʹ,6ʹ-dibromophenoxy)phenol Type: Simple biphenyl ethers. C13H8Br4O3 Source: Sponge Dysidea sp. (four sponge specimans, Indo-Pacific). Pharm: Inosine monophosphate dehydrogenase (IMPDH) inhibitor; guanosine monophosphate synthetase inhibitor; 15-lipoxygenase inhibitor. Ref: X. Fu, et al, JNP, 1995, 58, 1384 O

OH Br

O

Br

Br

Br

495 2-(3,5-Dibromo-2-methoxy-phenoxy)-3-bromophenol Type: Simple biphenyl ethers. C13H9Br3O3 Source: Sponge Phyllospongia dendyi (Palau, Oceania). Pharm: Toxic (variety of micro- and macro-algae). Ref: T. Hattori, et al, Fish. Sci., 2001, 67, 899 O

OH

Br

O

Br

Br

496 2-(4,6-Dibromo-2-methoxy-phenoxy)-3,5-dibromophenol Type: Simple biphenyl ethers. C13H8Br4O3 Source: Sponge Phyllospongia dendyi (Palau, Oceania). Pharm: Toxic (variety of micro- and macro-algae). Ref: T. Hattori, et al, Fish. Sci., 2001, 67, 899 O

OH O Br

Br Br

Br

497 2-(3,5-Dibromo-2-methoxy-phenoxy)-3,4,5-tribromoanisole Type: Simple biphenyl ethers. C14H9Br5O2 Cryst. (CHCl3), mp 142–144 °C. Source: Sponge Dysidea herbacea (Australia). Pharm: Antimicrobial (in vitro). Ref: R. S. Norton, et al, Tetrahedron, 1981, 37, 2341 O Br

O O

Br Br

Br Br

2.2 Diaryl Derivatives

165

498 2-(2,4-Dibromo-phenoxy)-3,4,5-tribromophenol Type: Simple biphenyl ethers. C12H5Br5O2 Cryst. (hexane), mp 195–196 °C, mp 185–186 °C. Source: Sponge Dysidea herbacea (Palau, Oceania). Pharm: Antimicrobial (in vitro). Ref: G. M. Sharma, et al, Tet. Lett., 1969, 1715│B. Carté, et al, Tetrahedron, 1981, 37, 2335 Br

OH O

Br

Br

Br Br

499 3,5-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹ-hydroxyphenoxy) phenol Type: Simple biphenyl ethers. C12H5Br5O3 Fine needles (MeOH), mp 132–133 °C. Source: Sponge Dysidea sp. (four sponge specimans, Indo-Pacific). Pharm: Inosine monophosphate dehydrogenase (IMPDH) inhibitor; guanosine monophosphate synthetase inhibitor; 15-lipoxygenase inhibitor. Ref: X. Fu, et al, JNP, 1995, 58, 1384 HO

Br

OH O Br Br

Br Br

500 4,6-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹ-hydroxyphenoxy) phenol Type: Simple biphenyl ethers. C12H5Br5O3 mp 132–133 °C. Source: Sponge Dysidea sp. (four sponge specimans, Indo-Pacific). Pharm: Inosine monophosphate dehydrogenase (IMPDH) inhibitor; guanosine monophosphate synthetase inhibitor; 15-lipoxygenase inhibitor. Ref: X. Fu, et al, JNP, 1995, 58, 1384 OH

OH Br

O

Br

Br Br

Br

501 4,6-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹ-hydroxyphenoxy) phenol-1-methylether Type: Simple biphenyl ethers. C13H7Br5O3 Viscous oil. Source: Sponge Dysidea sp. (four sponge specimans, Indo-Pacific). Pharm: Inosine monophosphate dehydrogenase (IMPDH) inhibitor; guanosine monophosphate synthetase inhibitor; 15-lipoxygenase inhibitor. Ref: X. Fu, et al, JNP, 1995, 58, 1384

166

2 Aromatic Metabolites

O

OH

Br

O

Br

Br Br

Br

502 Dimethyl-2,3ʹ-dimethylosoate Type: Simple biphenyl ethers. C19H20O8 Needles, mp 159–161 °C. Source: Marinederived fungus Aspergillus sp. B-F-2 (from sediment sample, China). Pharm: Cytotoxic (K562, IC50 = 76.5 μmol/L, might due to arresting cell cycle in S phase). Ref: R. Liu, et al, J. Antibiot., 2006, 59, 362 O

O

O O

HO

O O

O

503 Diorcinol Type: Simple biphenyl ethers. C12H10O3 Source: Marine-derived fungus Aspergillus sydowii ZSDS1-F6. Pharm: Antiviral (H3N2 virus, IC50 = 66.5 μmol/L); antibacterial (Klebsiella pneumonia, MIC = 21.7 μmol/L). Ref: J. -F. Wang, et al, J. Antibiot., 2014, 67, 581 HO

O

OH

504 Diorcinol Type: Simple biphenyl ethers. C14H14O3 Viscous oil. Source: Marine-derived fungus Aspergillus versicolor (sediment, Sakhalin Bay, Sea of Okhotsk, Russia). Pharm: Antibacterial (gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, MIC = 4.35 mmol/L); antifungal (yeast Candida albicans, MIC = 3.45 mmol/L); hemolytic (EC = 1.96 mmol/L); inhibits sperm fertilizing ability (IC50 = 0.078 mmol/L, at 10.87 mmol/L, has pronounced cytostatic effect and increases number of fertilized but undivided cells by 74%); cytotoxic (mouse splenic cells, MIC = 0.11 mmol/L). Ref: A. N. Yurchenko, et al, Russ. Chem. Bull., 2010, 59, 852 HO

O

OH

2.2 Diaryl Derivatives

167

505 Diorcinol 3,3′-Dihydroxy-5,5′-dimethyldiphenyl ether Type: Simple biphenyl ethers. C14H14O3 Viscous oil. Source: Sponge-derived fungus Aspergillus sydowii ZSDS1-F6, marinederived Aspergillus versicolor, deep-sea fungus Engyodontium album DFFSCS021. Pharm: Anti-HIV (IC50 = 66.5 μmol/L); antibacterial. Ref: L. J. Fremlin, et al, JNP, 2009, 72, 666│J. -F. Wang, et al, J. Antibiot., 2014, 67, 581│Q. Yao, et al, Mar. Drugs, 2014, 12, 5902 HO

O

OH

506 Diorcinol D Type: Simple biphenyl ethers. C19H22O3 Source: Marine-derived fungus Aspergillus versicolor (mud, Yellow Sea). Pharm: Cytotoxic (HTCLs). Ref: L. -N. Zhou, et al, Helv. Chim. Acta, 2011, 94, 1065│H. Gao, et al, J. Antibiot., 2013, 66, 539

O

OH

OH

507 Diorcinol E Type: Simple biphenyl ethers. C19H22O4 Source: Marine-derived fungus Aspergillus versicolor (mud, Yellow Sea). Pharm: Cytotoxic (HTCLs). Ref: L. -N. Zhou, et al, Helv. Chim. Acta, 2011, 94, 1065│H. Gao, et al, J. Antibiot., 2013, 66, 539

O O

OH

OH

508 2,3,3′,4,5,5′-Hexabromo-2′,6-dihydroxydiphenyl ether Type: Simple biphenyl ethers. C12H4Br6O3 Source: Sponges Carteriospongia foliascens [Syn. Phyllospongia foliascens] (Palau, Oceania) and Dysidea herbacea (Australia).

168

2 Aromatic Metabolites

Pharm: Antimicrobial (in vitro). Ref: B. Carté, et al, Tetrahedron, 1981, 37, 2335│ R. S. Norton, et al, Tetrahedron, 1981, 37, 2341 OH Br

OH O

Br

Br

Br

Br

Br

509 Lithothamnin A Type: Simple biphenyl ethers. C34H27Br5N4O10 Light yellow solid. Source: Red alga Lithothamnion fragilissimum (Lighthouse Reef, Palau Is.). Pharm: Cytotoxic (LOX, IC50 = 9.5 μmol/L; SNB19, IC50 = 7.6 μmol/L; OVCAR-3, IC50 = 7.6 μmol/L; Colon205, IC50 = 19.0 μmol/L; Molt4, IC50 = 19.0 μmol/L). Ref: A. W. W. Van Wyk, et al, JNP, 2011, 74, 1275 Br N

H N

Br

HO

OH

O Br

O

Br

OH

O

Br

O N H

OH N

OH

OH

510 O-Methylspongiadioxin A Type: Simple biphenyl ethers. C13H6Br4O3 Source: Sponge Dysidea dendyi. Pharm: Cell division inhibitor (fertilized eggs of sea urchin Strongylocentrotus intermedius, IC50 = 141 μmol/L). Ref: N. K. Utkina, et al, JNP, 2001, 64, 151; 2002, 65, 1213 O O

Br

O Br

Br Br

511 O-Methylspongiadioxin B Type: Simple biphenyl ethers. C13H6Br4O3 Needles (CHCl3) (semisynthetic), mp 204–206 °C (semisynthetic). Source: Sponge Dysidea dendyi. Pharm: Cell division inhibitor (fertilized eggs of sea urchin Strongylocentrotus intermedius, IC50 = 94 μmol/L). Ref: N. K. Utkina, et al, JNP, 2001, 64, 151; 2002, 65, 1213

2.2 Diaryl Derivatives

169

O Br

O

Br

O

Br

Br

512 O-Methylspongiadioxin C Type: Simple biphenyl ethers. C13H7Br3O3 Needles (CHCl3), mp 205–207 °C. Source: Sponge Dysidea dendyi. Pharm: Cell division inhibitor (fertilized eggs of sea urchin Strongylocentrotus intermedius, IC50 = 166 μmol/L). Ref: N. K. Utkina, et al, JNP, 2001, 64, 151; 2002, 65, 1213 O Br

O

O

Br

Br

513 Microsphaerol Type: Simple biphenyl ethers. C23H21Cl3O5 Source: Marine-derived fungus Microsphaeropsis sp. 7820 (endophytic). Pharm: Antibacterial (50 μg/disk: Enterobacter coli, IZ = 8 mm, Bacillus megaterium, IZ = 9 mm, Microbotryum violaceum IZ = 9 mm). Ref: H. Hussain, et al, Chem. Biodivers., 2015, 12, 289 Cl

Cl O

O

OH

O OH

Cl

514 2,3′,4,5,5′-Pentabromo-2′,6-dihydroxydiphenyl ether Type: Simple biphenyl ethers. C12H5Br5O3 Cryst. (CHCl3), mp 183–184 °C. Source: Sponges Carteriospongia [Syn. Phyllospongia] foliascens (Palau, Oceania) and Dysidea herbacea (Australia). Pharm: Antimicrobial (in vitro). Ref: B. Carté, et al, Tetrahedron, 1981, 37, 2335│R. S. Norton, et al, Tetrahedron, 1981, 37, 2341 OH Br

Br

OH O

Br

Br

Br

170

2 Aromatic Metabolites

515 2,3′,4,4′,5′-Pentabromo-2′-hydroxydiphenyl ether Type: Simple biphenyl ethers. C12H5Br5O2 mp 138–140 °C. Source: Sponge Dysidea herbacea (Palau, Oceania). Pharm: Antimicrobial (in vitro). Ref: G. M. Sharma, et al, Tet. Lett., 1969, 1715│B. Carté, et al, Tetrahedron, 1981, 37, 2335 OH

Br O

Br

Br

Br Br

516 2,3′,4,5,5′-Pentabromo-2′-hydroxy-6-methoxydiphenyl ether Type: Simple biphenyl ethers. C13H7Br5O3 Cryst. (CHCl3), mp 202–204 °C. Source: Sponge Dysidea sp. (four sponge specimans, Indo-Pacific). Pharm: Inosine monophosphate dehydrogenase (IMPDH) inhibitor; guanosine monophosphate synthetase inhibitor; 15-lipoxygenase inhibitor. Ref: X. Fu, et al, JNP, 1995, 58, 1384 O

OH

Br

O

Br

Br

Br

Br

517 Pestalotether A Type: Simple biphenyl ethers. C18H17ClO8 Colorless gum. Source: Mangrove-derived fungus Pestalotiopsis sp. from mangrove Rhizophora apiculata (branch, Satun, Thailand). Pharm: Antifungal (Cryptococcus neoformans ATCC 90112, MIC = 200 μg/mL, Candida albicans NCPF3153, inactive). Ref: S. Klaiklay, et al, Tetrahedron, 2012, 68, 2299 O

O

O O

O

O OH

OH Cl

518 Pestalotether B Type: Simple biphenyl ethers. C16H15ClO6 Colorless gum. Source: Mangrove-derived fungus Pestalotiopsis sp. from mangrove Rhizophora apiculata (branch, Satun, Thailand). Pharm: Antifungal (Cryptococcus neoformans ATCC 90112, MIC = 200 μg/mL, Candida albicans NCPF3153, inactive). Ref: S. Klaiklay, et al, Tetrahedron, 2012, 68, 2299

2.2 Diaryl Derivatives

O

171

O O

O

OH

OH Cl

519 Spongiadioxin A Type: Simple biphenyl ethers. C12H4Br4O3 Needles (CHCl3), mp 241–242 °C. Source: Sponge Dysidea dendyi (North West coast of Australia). Pharm: Cell division inhibitor (fertilized eggs of sea urchin Strongylocentrotus intermedius, IC50 = 4.8 μmol/L); cytotoxic (EAC, ED50 = 29 μg/mL); LD50 (mouse) > 150 mg/kg. Ref: N. K. Utkina, et al, JNP, 2001, 64, 151; 2002, 65, 1213 OH Br

O

O Br

Br Br

520 Spongiadioxin B Type: Simple biphenyl ethers. C12H4Br4O3 Needles (CHCl3), mp 245–247 °C. Source: Sponge Dysidea dendyi. Pharm: Cell division inhibitor (fertilized eggs of sea urchin Strongylocentrotus intermedius, IC50 = 1.1 μmol/L); cytotoxic (EAC, ED50 = 15.5 μg/mL); LD50 (mouse) > 150 mg/kg. Ref: N. K. Utkina, et al, JNP, 2001, 64, 151; 2002, 65, 1213 OH Br

O

Br

O

Br

Br

521 Spongiadioxin C Type: Simple biphenyl ethers. C12H5Br3O3 Needles (CHCl3), mp 203–205 °C. Source: Sponge Dysidea dendyi. Pharm: Cell division inhibitor (fertilized eggs of sea urchin Strongylocentrotus intermedius, IC50 = 5.7 μmol/L). Ref: N. K. Utkina, et al, JNP, 2001, 64, 151; 2002, 65, 1213 OH O

Br

O Br

Br

172

2 Aromatic Metabolites

522 Tedarene A Type: Simple biphenyl ethers. C19H18O2 Source: Sponge Tedania ignis (Sweetings Cay, Bahamas). Pharm: Atropisomeric; NO production inhibitor (LPS-induced macrophages). Ref: V. Costantino, et al, JOC, 2012, 77, 6377 OH O

523 2,3′,4,5′-Tetrabromo-2′,6-dimethoxydiphenyl ether Type: Simple biphenyl ethers. C14H10Br4O3 mp 86–88 °C. Source: Sponges Dysidea herbacea (Fiji, Australia) and Carteriospongia [Syn. Phyllospongia] foliascens (Palau, Oceania). Pharm: Antimicrobial (in vitro). Ref: R. S. Norton, et al, Tet. Lett., 1980, 21, 3801│B. Carté, et al, Tetrahedron, 1981, 37, 2335│115 R. S. Norton, et al, Tetrahedron, 1981, 37, 2341 O

O

Br

O

Br

Br

Br

524 3′,5′,6′,6-Tetrabromo-2,4-dimethyldiphenyl ether Type: Simple biphenyl ethers. C14H10Br4O Colorless oil. Source: Red alga Laurencia similis. Pharm: Hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 2.97 μg/mL, control HD, IC50 = 0.80 μg/mL). Ref: J. Qin, et al, Bioorganic Med. Chem. Lett., 2010, 20, 7152

Br

O

Br Br

Br

525 3,3′,5,5′-Tetrabromo-2-hydroxy-2′,6-dimethoxydiphenyl ether Type: Simple biphenyl ethers. C14H10Br4O4 Source: Sponge Phyllospongia dendyi (Palau, Oceania). Pharm: Toxic (variety of micro- and macro-algae). Ref: T. Hattori, et al, Fish. Sci., 2001, 67, 899

2.2 Diaryl Derivatives

Br

Br

O

O

173

O Br

Br

OH

526 2,2′,4,4′-Tetrabromo-6-hydroxydiphenyl ether Type: Simple biphenyl ethers. C12H6Br4O2 mp 172.5–173 °C. Source: Sponge Dysidea herbacea (Palau, Oceania). Pharm: Antimicrobial. Ref: B. Carté, et al, Tetrahedron, 1981, 37, 2335 OH

Br O

Br

Br

Br

527 2,3′,4,5′-Tetrabromo-2′-hydroxydiphenyl ether Type: Simple biphenyl ethers. C12H6Br4O2 Cryst. (hexane/petrol), mp 89–91 °C. Source: Sponges Dysidea herbacea and Dysidea chlorea (Palau, Oceania), cyanobacterium Oscillatoria spongeliae. Pharm: Antimicrobial. Ref: G. M. Sharma, et al, Tet. Lett., 1969, 1715│B. Carté, et al, Tetrahedron, 1981, 37, 2335│M. D. Unson, et al, Mar. Biol. 1994, 119, 1 Br

OH O

Br

Br Br

528 2,3′,4,5′-Tetrabromo-6-hydroxy-2′-methoxydiphenyl ether Type: Simple biphenyl ethers. C13H8Br4O3 Pale green wax, mp 32–33 °C. Source: Sponges Dysidea herbacea (Australia) and Dysidea spp. Pharm: Antimicrobial. Ref: R. S. Norton, et al, Tetrhedron, 1981, 37, 2341│N. K. Utkina, et al, Chem. Nat. Comp. 1994, 29, 291 O Br

OH O

Br Br

Br

174

2 Aromatic Metabolites

529 Tetraorcinol A Type: Simple biphenyl ethers. C28H26O5 Source: Marine-derived fungus Aspergillus versicolor from soft coral Cladiella sp. (Lingao, Hainan Province, China). Pharm: Antioxidant (DPPH scavenger, weak). Ref: Y. Zhuang, et al, Tetrahedron, 2011, 67, 7085 HO

O

O

O

OH

530 3,5,6-Tribromo-1-(2ʹ-bromophenoxy)-2-benzene methyl ether Type: Simple biphenyl ethers. C13H8Br4O2 Viscous oil. Source: Sponge Dysidea her bacea (West Sumatra, Indonesia). Pharm: Toxic (brine shrimp lethality test, IC50 = (26.25 ± 0.42)μg/mL)). Ref: D. Handayani, et al, JNP, 1997, 60, 1313 Br

O Br

O

Br Br

531 3,5,6-Tribromo-2-(2ʹ-bromophenoxy) phenol Type: Simple biphenyl ethers. C12H6Br4O2 Viscous oil. Source: Sponge Dysidea herbacea (West Sumatra, Indonesia). Pharm: Toxic (brine shrimp lethality test, IC50 = (3.20 ± 0.35)μg/mL)). Ref: D. Handayani, et al, JNP, 1997, 60, 1313 Br

OH O

Br

Br

Br

532 3,4,6-Tribromo-2-(2ʹ-bromophenoxy) phenol Type: Simple biphenyl ethers. C12H6Br4O2 Viscous oil. Source: Sponge Dysidea herbacea (West Sumatra, Indonesia). Pharm: Toxic (brine shrimp lethality test, IC50 = (3.20 ± 0.35)μg/mL). Ref: D. Handayani, et al, JNP, 1997, 60, 1313 Br

OH Br

O

Br Br

2.2 Diaryl Derivatives

175

533 3,4,5-Tribromo-2-(2ʹ-bromophenoxy)phenol Type: Simple biphenyl ethers. C12H6Br4O2 Viscous oil. Source: Sponge Dysidea herbacea (West Sumatra, Indonesia). Pharm: Toxic (brine shrimp lethality test, IC50 = (3.30 ± 0.51)μg/mL). Ref: D. Handayani, et al, JNP, 1997, 60, 1313 Br

OH O

Br

Br Br

534 2,3,4-Tribromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol Type: Simple biphenyl ethers. C12H5Br5O3 Needles (CHCl3/DMSO). Source: Sponge Lamellodysidea herbacea (Vim Levu, Fiji). Pharm: Bcl-2 protein inhibitor (mild). Ref: L. Calcul, et al, JNP, 2009, 72, 443 OH

OH

Br

O

Br

Br Br

Br

535 3,4,6-Tribromo-2-(3,5-dibromo-2-hydroxyphenoxy)phenol Type: Simple biphenyl ethers. C12H5Br5O3 Needles (MeCN). Source: Sponge Lamellodysidea herbacea (Vim Levu, Fiji). Pharm: Bcl-2 protein inhibitor (mild). Ref: L. Calcul, et al, JNP, 2009, 72, 443 OH Br

OH O

Br

Br Br

Br

536 2,4ʹ,5-Tribromo-2ʹ,3ʹ,6-trihydroxy-3,6ʹ-bis(hydroxymethyl)diphenyl ether Type: Simple biphenyl ethers. C14H11Br3O6 Pale yellow solid. Source: Red alga Odonthalia corymbifera. Pharm: α-Glucosidase inhibitor (IC50 = 25 μmol/L). Ref: H. Kurihara, et al, JNP, 1999, 62, 882 OH Br

OH

O

Br HO

OH

HO

Br

176

2 Aromatic Metabolites

537 2,4,4ʹ-Trichloro-2ʹ-hydroxydiphenyl ether Type: Simple biphenyl ethers. C12H7Cl3O2 Off-white cryst. powder or soft agglomerates, mp 54–57 °C, Insol. H2O, sol. org. solvs. Source: Marine-derived bacterium Micrococcus luteus from sponge Xestospongia sp. (surface, Indo-Pacific). Pharm: Bacteriostatic; low acute toxicity; Fab I inhibitor. Ref: R. Zinkernagle, et al, Seifenoele-fette wachse, 1967, 93, 670│CRC Press, DNP on DVD, 2012, Version 20.2 OH

Cl O

Cl

Cl

538 Altenusin Type: Simple biphenyls. C15H14O6 Source: Mangrove-derived fungus Alternaria sp. JCM9.2. Pharm: Antibacterial (MRSA, MIC = 31.25 μg/mL; Enterococcus faecalis, MIC = 62.5 μg/mL; Enterobacter cloacae, MIC = 125 μg/mL; Candida albicans, MIC = 125 μg/mL). Ref: J. Kjer, et al, JNP, 2009, 72, 2053 OH OH

O

HO HO

O

539 (2E,2ʹZ)-3,3ʹ-(6,6ʹ-Dihydroxybiphenyl-3,3ʹ-diyl)diacrylic acid Type: Simple biphenyls. C18H14O6 White amorphous powder. Source: Marine-derived fungus Spicaria elegans KLA-03. Pharm: Antibacterial (Enterobacter aerogenes, MIC = 0.15 μmol/L, Enterobacter coli, MIC = 0.04 μmol/L, Pseudomonas aeruginosa, MIC = 1.53 μmol/L, Staphylococcus aureus, MIC = 0.77 μmol/L); antifungal (yeast Candida albicans, MIC = 0.38 μmol/L). Ref: Y. Wang, et al, Mar. Drugs, 2011, 9, 535 OH

OH

O OH O

OH

540 4-(3-Hydroxypropyl)-5,6-dimethoxybiphenyl-3,4ʹ-diol Type: Simple biphenyls. C17H20O5 Needles, mp 205–207 °C. Source: Mangrovederived fungus Penicillium thomi from mangrove Bruguiera gymnorrhiza (root, China).

2.2 Diaryl Derivatives

177

Pharm: Cytotoxic (A549, HepG2 and HT29, moderate). Ref: G. Chen, et al, J. Asian Nat. Prod. Res., 2007, 9, 159 OH

OH

HO O

O

541 Tedarene B Type: Simple biphenyls. C19H17O5S1– Source: Sponge Tedania ignis (Sweetings Cay, Bahamas). Pharm: Atropisomeric. Ref: V. Costantino, et al, JOC, 2012, 77, 6377 –

O O

O S

O

OH

H

542 3′,4,4′′-Trihydroxy-2′,6′-dimethoxy-p-terphenyl Type: Simple biphenyls. C20H18O5 Source: Deep-sea fungus Aspergillus candidus. Pharm: Antifungal (Candida albicans, great growth inhibition). Ref: F. Liu, et al, J. Xiamen Univ. 2013, 52, 670 (in Chinese) OH O

O HO

OH

543 Ulocladol Type: Simple biphenyls. C16H14O7 Powder, mp 110–111 °C. Source: Marine-derived fungus Ulocladium botrytis (culture) from sponge Myxilla incrustans, marine-derived fungus Microsphaeropsis olivacea. Pharm: Tyrosine kinase p56lck inhibitor (ELISAbased assay, 0.02 μg/mL, reduced enzyme activity to 7%, since p56lck is necessary for T-cell activation, inhibitors of kinase could be useful for treating autoimmune diseases). Ref: U. Holler, et al, EurJOC, 1999, 2949│D. R. Goldberg, et al, JMC, 2003, 46, 1337│E. Hormazabal, et al, Z. Naturforsch., C, 2005, 60, 11

178

2 Aromatic Metabolites

O OH

4

OH

HO

O O

O

544 6,6ʹ-Bieckol 8,8’-Bieckol Type: Phlorotannins. C36H22O18 Prisms (H2O), mp 300 °C. Source: Brown algae Ecklonia kurome, Ecklonia cava. and Eisenia arborea. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 22.2 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 > 500 μmol/L); antiplasmin inhibitor; α2-macroglobulin inhibitor; antiviral (inhibits HIV-1 infection IC50 = 1.07–1.72 μmol/L, MMOA: Viralp24 antigen production and reverse transcriptase inhibition). Ref: Y. Fukuyama, et al, CPB, 1989, 37, 2438│M. Artan, et al, BoMC, 2008, 16, 7921│S. H. Lee, et al, J. Sci. Food Agric. 2009, 89, 1552

OH

OH

O

O

OH HO

OH

O

HO HO

OH

O

OH

OH

O O

OH

OH

545 Crossbyanol B Type: Phlorotannins. C30H15Br7O12S2 Pale yellow solid. Source: Cyanobacterium Leptolyngbya crossbyana (Honaunau Reef, Hawaii). Pharm: Antibacterial (MRSA); toxic (brine shrimp, relatively potent). Ref: H. Choi, et al, JNP, 2010, 73, 517

2.2 Diaryl Derivatives

Br

179

Br Br

Br

O O

Br

O

Br

O

4'

O S HO O

O Br

4''

O

S O

O OH

546 Dibenzo [1,4]dioxine-2,4,7,9-tetraol Type: Phlorotannins. C12H8O6 Source: Brown alga Ecklonia maxima. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 33.69 μmol/L, control Acarbose, IC50 = 1013 μmol/L); antioxidant (DPPH scavenger, EC50 = 0.012 μmol/L, AAI (antioxidant activity index = final DPPH concentration/EC50) = 4037, control Ascorbic acid, EC50 = 0.011 μmol/L, AAI = 4356). Ref: K. R. Rengasamy, et al, Food Chem., 2013, 141, 1412 OH HO

O

O

OH

OH

547 Dieckol 4ʹʹʹ-O-7-Bieckol Type: Phlorotannins. C36H22O18 Cryst., mp 300 °C. Source: Brown algae Ecklonia kurome, Ecklonia stolonifera Eisenia bicyclis and Ecklonia cava. Pharm: Hypoglycemic (α-amylase inhibitor) (in vitro assay, 1 mmol/L, InRt = 97.5%); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 1.61 μmol/L); hypoglycemic (α-glucosidase inhibitor) (IC50 = 10.8 μmol/L); hypoglycemic (α-amylase inhibitor) (IC50 = 124.9 μmol/L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 0.24 mmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 = 0.66 mmol/L); hypoglycemic (AGE formation inhibition, in vitro assay, 1 mmol/L, InRt = 86.7%); Hypoglycemic (aldose reductase inhibitor) (rat lens aldose reductase in vitro assay, IC50 = 42.39 μmol/L); hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 1.18 μmol/L); hypoglycemic (C57BL/KsJ-db/db diabetic mice in vivo, reduction of blood glucose, glycosylated hemoglobin levels; reduction of hepatic lipids concentration and improvement of impaired glucose tolerance; reduction of glucose-6-phosphatase and phosphoenolpyruvate carboxykinase enzymes activities; and increased glucokinase activity); hypoglycemic (Streptozotocin-induced diabetic mice in vivo, reduction of post-prandial blood glucose level and delayed absorption of dietary carbohydrates); hypoglycemic (Pancreatic lipase inhibitor) (in vitro assay, IC50 = 0.26mg/mL); hypoglycemic (Pancreatic lipase inhibitor)

180

2 Aromatic Metabolites

(in vitro assay, IC50 = 99.3 μmol/L); antioxidant (10 μg/mL or 100 μg/mL); reduction of ROS over-production; anti-inflammatory (reduction of pro-inflammatory NF-κB, COX-2 and iNOS expressions); attenuates type II diabetes (db/db mouse model); reduction of oxidative stress (in vivo, increasing activities of hepatic antioxidant enzymes including glutathione peroxidase and superoxide dismutase); inihibits actions of plasma α2-macroglobulin and α2-plasmin inhibitor; histamine release inhibitor (hmn basophilic granulocyte KU-812, IC50 = 27.8 μmol/L). Ref: K. -W. Glombitza, et al, Phytochemistry, 1985, 24, 543│Y. Okada, et al, JNP, 2004, 67, 103│H. A. Jung, et al, Fish. Sci., 2008, 74, 1363│S. H. Lee, et al, J. Sci. Food Agric., 2009, 89, 1552│Q. T. Le, et al, Process Biochem, 2009, 44, 168│S. H. Lee, et al, Food Chem. Toxicol. 2010, 48, 2633│S. H. Lee, et al, Toxicol. Vitro, 2010, 24, 375│H. E. Moon, et al, Biosci. Biotechnol. Biochem., 2011, 75, 1472│S. H. Lee, et al, Food Chem. Toxicol., 2012, 50, 575│K. B. W. R. Kim, et al, Biotechnol. Bioprocess Eng., 2012, 17, 739│S. H. Eom, et al, Phytother. Res., 2013, 27, 148│M. C. Kang, et al, Food Chem. Toxicol., 2013, 53, 294 OH

OH

OH

O

O OH

HO

OH

OH

O O

HO

OH

O O

OH

O OH

548 Dioxinodehydroeckol Type: Phlorotannins. C18H10O9 Powder. Source: Brown algae Ecklonia stolonifera, Eisenia arborea, Ecklonia maxima and Eisenia bicyclis. Pharm: Hypoglycemic (aldose reductase inhibitor) (rat lens aldose reductase in vitro assay, IC50 = 21.95 μmol/ L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 34.60 μmol/L) (Moon, 2011); hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 29.97 μmol/L) (Moon, 2011); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 97.33 nmol/L) (Eom, 2012); Hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 = 472.70 μmol/L) (Eom, 2012). Ref: K. -W. Glombitza, et al, Phytochemistry, 1985, 24, 543│K. -W. Glombitza, et al, Planta Med., 1985, 51, 308│H. S. Kang, et al, CPB,

2.2 Diaryl Derivatives

181

2003, 51, 1012 H. A. Jung, et al, Fish. Sci., 2008, 74, 1363│H. E. Moon, et al, Biosci. Biotechnol. Biochem., 2011, 75, 1472│S. H. Eom, et al, J. Sci. Food Agric., 2012, 92, 2084 HO

OH

O HO

O

O

O

OH

OH

549 Diphlorethohydroxycarmalol DPHC Type: Phlorotannins. C24H16O13 Source: Brown algae Carpophyllum maschalocarpum and Ishige okamurae. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 0.16 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 = 0.53 μmol/L); hypoglycemic (Streptozotocin-induced diabetic mice in vivo, reduction of post-prandial blood glucose level and delayed absorption of dietary carbohydrates). Ref: S. -M. Li, et al, Phytochemistry, 1991, 30, 3417│S. J. Heo, et al, J. Microbiol. Biotechnol., 2008, 18, 676│S. J. Heo, et al, Eur. J. Pharmacol., 2009, 615, 252. OH

OH

HO

HO

O

O

O OH

OH OH

OH

O OH

550 Eckol Hexahydroxyphenoxydibenzo[1,4]dioxine Type: Phlorotannins. C18H12O9 Cryst., mp 243–244 °C. Source: Brown algae Ecklonia stolonifera, Ecklonia kurome, Ecklonia maxima, Eisenia arborea and Eisenia bicyclis. Pharm: Hypoglycemic (α-amylase inhibitor) (in vitro assay, 1 mmol/L, InRt = 87.5%); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 22.78 μmol/L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 11.16 μmol/L, control Acarbose, IC50 = 1013 μmol/L); hypoglycemic (AGE formation inhibition, in vitro assay, 1 mmol/L, InRt = 96.2%); hypoglycemic (aldose reductase inhibitor) (rat lens aldose reductase in vitro assay, IC50 = 54.68 μmol/L); hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 2.64 μmol/L); hypoglycemic (pancreatic lipase inhibitor) (in vitro assay, IC50 = 76.6 μmol/L); antioxidant (DPPH scavenger, EC50 = 0.008 μmol/L, AAI (antioxidant activity index = final DPPH concentration/EC50) = 6096, control Ascorbic acid, EC50 = 0.011 μmol/L, AAI = 4356); α2-macroglobulin inhibitor; glycation inhibitor. Ref: K. -W. Glombitza, et al, Phytochemistry, 1985, 24, 543│Y. Fukuyama, et al,

182

2 Aromatic Metabolites

CPB, 1989, 37, 349│Y. Okada, et al, JNP, 2004, 67, 103│H. A. Jung, et al, Fish. Sci., 2008, 74, 1363│H. E. Moon, et al, Biosci. Biotechnol. Biochem., 2011, 75, 1472│K. R. Rengasamy, et al, Food Chem., 2013, 141, 1412│S. H. Eom, et al, Phytother. Res. 2013, 27, 148

OH

OH

O

OH O

HO

OH

O OH

551 Fucodiphlorethol G Type: Phlorotannins. C24H18O12 Source: Brown alga Ecklonia cava. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 19.5 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 > 500 μmol/L). Ref: S. H. Lee, et al, J. Sci. Food Agric. 2009, 89, 1552

OH

HO

HO

O OH

OH

HO

OH

O

OH

OH

OH

552 Fucofuroeckol A Type: Phlorotannins. C24H14O11 Source: Brown alga Eisenia bicyclis. Pharm: Hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 = 42.91 μmol/L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 131.34 nmol/L); hypoglycemic (Pancreatic lipase inhibitor) (in vitro assay, IC50 = 37.2 μmol/L). Ref: S. H. Eom, et al, et al, J. Sci. Food Agric. 2012, 92, 2084│S. H. Eom, et al, Phytother. Res., 2013, 27, 148

2.2 Diaryl Derivatives

183

OH

OH

O

OH

O

OH

O

O

OH OH

HO

553 Octaphlorethol A Type: Phlorotannins. C48H34O24 Source: Brown alga Ishige foliacea (Jeju I., R. O. Korea). Pharm: Hypoglycemic (increased glucose uptake by GLUT4 via PI3-K/Akt and AMPK signalling pathways, L-6 rat myoblast cells in vitro); antioxidant (increased anti-oxidative glutathione peroxidase (GSH-px), catalase (CAT) and superoxide dismutase (SOD) activities); antioxidant (reduction of ROS over-production); cytoprotection of pancreatic β-cells (protects pancreatic β-cells damage caused by hyperglycaemia due to streptozotocin treatment); antidiabetic. Ref: S. H. Lee, et al, Biochem. Biophys. Res. Commun. 2012, 420, 576│S. H. Lee, et al, Food Chem. Toxicol., 2013, 59, 643 HO OH O

O HO OH

HO O

HO

HO

HO

O

OH

OH

OH

OH

HO

O

HO

HO

O

OH O

OH

554 2-Phloro-6,6ʹ-bieckol 2-O-(2,4,6-Trihydroxyphenyl)-6,6ʹ-bieckol Type: Phlorotannins. C42H26O21 Amorph. solid. Source: Brown alga Ecklonia kurome. Pharm: Antiplasmin inhibitor; α2-macroglobulin inhibitor. Ref: Y. Fukuyama, et al, CPB, 1989, 37, 2438

184

2 Aromatic Metabolites

OH HO O

O

OH

OH

OH

O

HO O

OH HO

OH

O

O

HO HO

OH

OH

O

OH

555 2-Phloroeckol Type: Phlorotannins. C24H16O12 Source: Brown alga Ecklonia kurome. Pharm: Inihibits action of plasma α2-macroglobulin; α2-plasmin inhibitor. Ref: K. -W. Glombitza, et al, Phytochemistry, 1985, 24, 543 HO

OH

O

OH O

HO

O

O

OH

HO

OH

OH

556 7-Phloroeckol 1-(3′,5′-Dihydroxyphenoxy)-7-(2″,4″,6″-trihydroxyphenoxy)-2,4,9-trihydroxydibenzo1,4-dioxin Type: Phlorotannins. C24H16O12 Source: Brown algae Ecklonia stolonifera, Eisenia bicyclis, and Ecklonia cava. Pharm: Hypoglycemic (AGE formation inhibition, in vitro assay, 1 mmol/L, InRt = 91.1%) (Okada, 2004); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 6.13 μmol/L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 49.5 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 = 250 μmol/L); hypoglycemic (aldose reductase inhibitor) (rat lens aldose reductase in vitro assay, IC50 = 27.54 μmol/L); hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 2.09 μmol/L); hypoglycemic (Pancreatic lipase inhibitor) (in vitro assay, IC50 = 12.7 μmol/L). Ref: Y. Okada, et al, JNP, 2004, 67, 103│H. A. Jung, et al, Fish. Sci., 2008, 74, 1363│S. H. Lee, et al, J. Sci. Food Agric. 2009, 89, 1552│H. E. Moon, et al, Biosci. Biotechnol. Biochem., 2011, 75, 1472│S. H. Eom, et al, Phytother. Res., 2013, 27, 148

2.2 Diaryl Derivatives

185

OH

O

OH HO

OH

O

O

O

OH OH

OH

OH

557 Phlorofucofuroeckol A Type: Phlorotannins. C30H18O14 Amorph. solid. Source: Brown algae (edible) Ecklonia stolonifera, Eisenia bicyclis, Ecklonia kurome and Ecklonia cava. Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 1.37 μmol/L); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, IC50 = 19.7 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 > 500 μmol/L); hypoglycemic (aldose reductase inhibitor) (rat lens aldose reductase in vitro assay, IC50 = 125.45 μmol/L) (Jung, 2008); hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 0.56 μmol/L) (Moon, 2011); antiplasmin inhibitor. Ref: Y. Fukuyama, et al, CPB, 1990, 38, 133│H. A. Jung, et al, Fish. Sci., 2008, 74, 1363│Y. Li, et al, BoMC, 2009, 17, 1963│S. H. Lee, et al, J. Sci. Food Agric., 2009, 89, 1552│H. E. Moon, et al, Biosci. Biotechnol. Biochem., 2011, 75, 1472 HO OH

OH

O O

HO

O OH

HO OH

O

O

HO

OH

558 Phlorofucofuroeckol B Type: Phlorotannins. C30H18O14 Yellow-brown oil. Source: Brown alga Eisenia arborea (edible). Pharm: Anti-inflammatory (rat basophilic leukemia cell histamine release inhibition, IC50 = 7.8 μmol/L, MMOA: inhibition of β-hexosaminidase release); antiallergic phlorotannins. Ref: Y. Sugiura, et al, Food Sci. Technol. Res. 2007, 13, 54 OH

OH OH HO

HO O

HO

O

OH

O O

OH

O OH

186

2 Aromatic Metabolites

559 2,7ʹʹ-Phloroglucinol-6,6ʹ-bieckol Type: Phlorotannins. C48H30O23 Source: Brown alga Ecklonia cava (Jeju I., R. O. Korea). Pharm: Antioxidant. Ref: S. -M. Kang, et al, J. Funct. Foods, 2012, 4, 158 HO

OH

OH

OH HO

O

O

O

HO

OH

O O

O

HO OH

OH

OH

O O

OH

OH

OH

HO

560 Phlorotannin DDBT 2-(4-(3,5-Dihydroxyphenoxy)-3,5-dihydroxyphenoxy) benzene-1,3,5-triol Type: Phlorotannins. C18H16O9 Source: Brown alga Sargassum patens. Pharm: Hypoglycemic (α-amylase inhibitor) (in vitro assay, IC50 = 3.2 μg/mL); hypoglycemic (α-glucosidase inhibitor) (in vitro assay, rat intestinal maltase, IC50 = 114.0 μg/mL; rat instestinal sucrase, IC50 = 25.4 μg/mL). Ref: Y. Kawamura-Konishi, et al, J. Agric. Food Chem. 2012, 60, 5565 OH

OH HO

HO

O

O

HO

OH

OH

561 Phlorotannin representative trimer B Type: Phlorotannins. C18H16O9 Source: Brown alga Fucus distichus (subfraction FD-E-22, Alaska). Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Fucus distichus’ ethyl acetate subfraction 22 (FD-E-22), IC50 = 0.89 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, Fucus distichus’ ethyl acetate subfraction 22 (FD-E-22), IC50 = 13.9 μmol/L). Ref: J. Kellogg, et al, Mar. Drugs, 2014, 12, 5277

2.2 Diaryl Derivatives

HO OH

OH OH

OH OH HO

HO

187

OH

with aryl-aryl bonds

562 Phlorotannin representative trimer C Type: Phlorotannins. C18H16O9 Source: Brown alga Fucus distichus (subfraction FD-E-22, Alaska). Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Fucus distichus’ ethyl acetate subfraction 22 (FD-E-22), IC50 = 0.89 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, Fucus distichus’ ethyl acetate subfraction 22 (FD-E-22), IC50 = 13.9 μmol/L). Ref: J. Kellogg, et al, Mar. Drugs, 2014, 12, 5277 OH with ether bridges

OH

O

OH

O HO

OH

OH OH

563 Phlorotannin representative trimer D Type: Phlorotannins. C18H16O8 Source: Brown alga Fucus distichus (subfraction FD-E-22, Alaska). Pharm: Hypoglycemic (α-glucosidase inhibitor) (in vitro assay, Fucus distichus’ ethyl acetate subfraction 22 (FD-E-22), IC50 = 0.89 μmol/L); hypoglycemic (α-amylase inhibitor) (in vitro assay, Fucus distichus’ ethyl acetate subfraction 22 (FD-E-22), IC50 = 13.9 μmol/L). Ref: J. Kellogg, et al, Mar. Drugs, 2014, 12, 5277 HO

OH OH H OH HO with mixed linkages

OH

O OH

564 Aplysillin A 3-Bromo-5-[4-(3-bromo-4-hydroxyphenyl)-2,3-bis(sulfoxy)-1,3-butadienyl]-1,2-benzenediol Type: Diarylalkyls. C16H12Br2O11S2 Source: Sponge Aplysina fistularis fulva. Pharm: Thrombin receptor antagonist (inhibits binding of [125I]-thrombin to platelet membranes, IC50 = 20 μmol/L, weak). Ref: N. K. Gulavita, et al, JNP, 1995, 58, 954

188

2 Aromatic Metabolites

O H

O

S

O

OH OH

O

Br O

HO Br

O

S

O

H

O

565 1,2-Bis(2,3,6-tribromo-4,5-dihydroxyphenyl)ethane Type: Diarylalkyls. C14H8Br6O4 Amorph. solid, mp 230–232 °C. Source: Red alga Symphyocladia latiuscula. Pharm: Hypoglycemic (PTP1B inhibitor) (in vitro assay, IC50 = 3.5 μmol/L). Ref: X. -J. Duan, et al, JNP, 2007, 70, 1210│X. Liu, et al, Chin. J. Oceanol. Limnol., 2011, 29, 686 OH OH

Br

Br Br

Br

HO

Br

Br OH

566 8-Carboxy-isoiantheran A Type: Diarylalkyls. C33H18Br4O14S2 Brownish amorphous solid. Source: Sponge Ianthella quadrangulata (Australia, polar extract). Pharm: Immune system activity (activation of Ca2+-mobilization, IC50 = 0.48–1.3 μmol/L, MMOA: ionotropic P2Y11 receptor activation); P2Y11 receptor agonist (EC50 = 0.48 μmol/L, showed some selectivity for P2Y11 over P2Y1 and P2Y2 receptors). Ref: H. Greve, et al, JMC, 2007, 50, 5600 O

Br

Br O

O

HO

S

OH O

OH

1'

O OH

O HO

S O

O

O Br

Br

567 Colpol 2-Bromo-5-[4-(4-bromo-2-hydroxy-5-methoxyphenyl)-2-butenyl]-1,3-benzenediole Type: Diarylalkyls. C17H16Br2O4 Source: Brown alga Colpomenia sinuosa (Red Sea). Pharm: Cytotoxic (P388, A549, HT29 and CV-1, IC50 = 10 μg/mL). Ref: D. Green, et al, JNP, 1993, 56, 1201

2.2 Diaryl Derivatives

189

OH OH

Br

Br OH

O

568 Iantheran A Type: Diarylalkyls. C32H18Br4O12S2 Pale yellow cryst. (di-Na salt), mp 172–173 °C (dec, di-Na salt). Source: Sponge Ianthella sp. (Australia). Pharm: Na/K-ATPase inhibitor (IC50 = 10 μmol/L). Ref: Y. Okamoto, et al, Tet. Lett., 1999, 40, 507│Y. Okamoto, et al, BoMC, 2001, 9, 179 OH

Br O

Br O

S

O

OH O

1'

O HO

O

S

O Br

O

Br

HO

569 Iantheran B 8-Carboxy-isoiantheran A Type: Diarylalkyls. C32H22Br4O12S2 mp 155–156 °C (dec) (di-Na salt). Source: Sponge Ianthella sp. (Great Barrier Reef, Australia). Pharm: Na/K-ATPase inhibitor. Ref: Y. Okamoto, et al, BoMC, 2001, 9, 179 Br O HO

Br H

Br O

O S O

O O

O Br

S O

O

H

O

HO

570 Isoiantheran A Type: Diarylalkyls. C32H18Br4O12S2 Brownish amorphous solid, [α]D23 = −0.7° (c = 0.39, MeOH). Source: Sponge Ianthella quadrangulata (Australia, polar extract). Pharm: Immune system activity (activation of Ca2+-mobilization, IC50 = 0.48–1.3 μmol/L,

190

2 Aromatic Metabolites

MMOA: ionotropic P2Y11 receptor activation); P2Y11 receptor agonist (EC50 = 1.29 μmol/L). Ref: H. Greve, et al, JMC, 2007, 50, 5600 Br

Br

O

O

O

HO

S

OH O OH

1'

O HO

S

O

O Br

O

Br

571 Panicein A2 Type: Diarylalkyls. C22H26O3 Oil. Source: Sponge Reniera mucosa. Pharm: Cytotoxic (P388, A549, HT29 and MEL28, ED50 = 5 μg/mL). Ref: E. Zubía, et al, Tetrahedron, 1994, 50, 8153│M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) O

OH

O

572 Panicein F1 Type: Diarylalkyls. C22H28O4 Orange oil. Source: Sponge Reniera mucosa. Pharm: Cytotoxic (P388, A549 and MEL28, ED50 = 5 μg/mL); DHFR inhibitor (ED50 = 3 μg/mL). Ref: E. Zubia, et al, Tetrahedron, 1994, 50, 8153│M. Gordaliza, et al, Mar. Drugs, 2010, 8, 2849 (rev) OH

OH O HO

573 3ʹʹ-Deoxy-6ʹ-O-desmethylcandidusin B Type: Terphenyls. C19H14O6 Source: Mangrove-derived fungus Penicillium chermesinum from mangrove Kandelia candel (South China Sea, Guangdong, China). Pharm: Acetylcholinesterase inhibitor. Ref: H. Huang, et al, JNP, 2011, 74, 997

2.2 Diaryl Derivatives

191

O

O

OH

HO HO

HO

574 4ʹʹ-Deoxyisoterprenin Type: Terphenyls. C25H26O5 Powder. Source: Marine-derived fungus Aspergillus candidus IF10 (from sediment sample, Japan waters). Pharm: Cytotoxic (KB-3-1, moderate). Ref: H. Wei, et al, J. Antibiot., 2007, 60, 586

O

OH

O OH

O

575 4ʹʹ-Deoxyprenylterphenyllin Type: Terphenyls. C25H26O4 Powder. Source: Marine-derived fungus Aspergillus candidus IF10 (from sediment sample, Japan waters). Pharm: Cytotoxic (KB-3-1, moderate). Ref: H. Wei, et al, J. Antibiot., 2007, 60, 586

O

OH OH O

576 4ʹʹ-Deoxyterprenin Type: Terphenyls. C25H26O5 Cryst. Source: Marine-derived fungus Aspergillus candidus (from sediment sample, Japan waters). Pharm: Cytotoxic (KB-3-1, moderate); Immunosuppressant; antimetabolite effect. Ref: H. Wei, et al, J. Antibiot., 2007, 60, 586

O

OH

OH O

O

192

2 Aromatic Metabolites

577 6ʹ-O-Desmethylterphenyllin Type: Terphenyls. C19H16O5 Source: Mangrove-derived fungus Penicillium chermesinum from mangrove Kandelia candel (South China Sea, Guangdong, China). Pharm: α-Glucosidase inhibitor (strong). Ref: H. Huang, et al, JNP, 2011, 74, 997 HO

O OH

HO HO

578 3-Hydroxy-6ʹ-O-desmethylterphenyllin Type: Terphenyls. C19H16O6 Source: Mangrove-derived fungus Penicillium chermesinum from mangrove Kandelia candel (South China Sea, Guangdong, China). Pharm: α-Glucosidase inhibitor (strong). Ref: H. Huang, et al, JNP, 2011, 74, 997 HO

O OH

HO HO

HO

579 Prenylterphenyllin Type: Terphenyls. C25H26O5 Powder. Source: Marine-derived fungus Aspergillus candidus IF10 (from sediment sample, Japan waters). Pharm: Cytotoxic (KB-3-1, moderate). Ref: H. Wei, et al, J. Antibiot., 2007, 60, 586

O

OH OH

HO O

580 Terprenin Type: Terphenyls. C20H26O6 Prisms, mp 155.5–156 °C. Source: Terrestrial fungus Aspergillus candidus. Pharm: Immunosuppressant. Ref: T. Kamigauchi, et al, J. Antibiot., 1998, 51, 445

HO

HO

O OH

O O

2.2 Diaryl Derivatives

193

581 3′,4,4′′-Trihydroxy-2′,5′-dimethoxy-p-terphenyl Terphenyllin Type: Terphenyls. C20H18O5 mp 239 °C (dec). Source: Deep-sea fungus Aspergillus candidus, terrestrial fungus Aspergillus candidus. Pharm: Plant growth inhibitor. Ref: R. Marchelli, et al, J. Antibiot., 1975, 28, 328│F. Liu, et al, J. Xiamen Univ., 2013, 52, 670 (in Chinese)

4

O

OH

2'

3'

4''

OH

HO 5'

O

582 Aspulvinone E Type: Pulvinone group. C17H12O5 Yellow needles (MeOH), mp 282–284 °C, 275 °C. Source: Mangrove-derived fungus Aspergillus terreus GWQ-48 from unidentified mangrove (rhizospehere soil, Fujian Province, China), terrestrial fungus Aspergillus terreus. Pharm: Antiviral (IFV H1N1 virus inhibitor, IC50 = 192.05 μmol/L, significant); glucose-6-phosphatase inhibitor. Ref: N. Ojima, et al, Phytochemistry, 1973, 12, 2527│Vertesy, L. et al, J. Antibiot., 2000, 53, 677│H. Gao, et al, Bioorg. Med. Chem. Lett., 2013, 23, 1776│S. Z. Moghadamtousi, et al, Mar. Drugs, 2015, 13, 4520 (rev) O

O

OH HO OH

583 Cadiolide B Type: Pulvinone group. C24H10Br6O6 Orange amorph. solid. Source: Ascidians Pseudodistoma antinboja (Tong-Yeong City, R. O. Korea) and Botryllus sp. Pharm: Antibacterial (MSSA and MRSA). Ref: C. J. Smith, et al, JOC, 1998, 63, 4147│W. Wang, et al, JNP, 2012, 75, 2049 OH Br

Br

O O O Br

Br H

HO Br

5Z

OH Br

194

2 Aromatic Metabolites

584 Cadiolide E Type: Pulvinone group. C24H11Br5O6 Source: Ascidian Pseudodistoma antinboja (Tong-Yeong City, R. O. Korea). Pharm: Antibacterial (gram-positive and -negative bacteria). Ref: W. Wang, et al, JNP, 2012, 75, 2049 OH Br

Br

O O O Br

Br H

HO

5Z

OH Br

585 Cadiolide G Type: Pulvinone group. C24H14Br4O6 Source: Ascidian Synoicum sp. (Chuja-do, R. O. Korea). Pharm: Antibacterial (gram-positive and -negative bacteria). Ref: T. H. Won, et al, JNP, 2012, 75, 2055 OH Br

Br

O HO O Br

HO

H

5Z

OH Br

586 (5E)-Cadiolide H Type: Pulvinone group. C25H16Br4O6 Source: Ascidian Synoicum sp. (Chuja-do, R. O. Korea). Pharm: Antibacterial (gram-positive and -negative bacteria). Ref: T. H. Won, et al, JNP, 2012, 75, 2055

2.2 Diaryl Derivatives

195

OH Br

Br

O HO O Br 5E

HO

H

Br O

587 (5Z)-Cadiolide H Type: Pulvinone group. C25H16Br4O6 Source: Ascidian Synoicum sp. (Chuja-do, R. O. Korea). Pharm: Antibacterial (gram-positive and -negative bacteria). Ref: T. H. Won, et al, JNP, 2012, 75, 2055 OH Br

Br

O HO O Br H

HO

5Z

O

Br

588 Cadiolide I Type: Pulvinone group. C25H12Br6O7 Source: Ascidian Synoicum sp. (Chuja-do, R. O. Korea). Pharm: Antibacterial (gram-positive and -negative bacteria). Ref: T. H. Won, et al, JNP, 2012, 75, 2055 Br HO O Br O

O

Br O OH

Br Br HO

Br

196

2 Aromatic Metabolites

589 Isoaspulvinone E Type: Pulvinone group. C17H12O5 Source: Mangrove-derived fungus Aspergillus terreus from unidentified mangrove (rhizospehere soil, Fujian Province, China). Pharm: Antiviral (H1N1 virus inhibitor, significant, inhibits H1N1 viral neuraminidase). Ref: H. Gao, et al, Bioorg. Med. Chem. Lett., 2013, 23, 1776 O

O

OH HO OH

590 Pulvic acid Pulvinic acid Type: Pulvinone group. C12H8O4 Orange powder (Et2O or CHCl3), orange prisms (C6H6), mp 216–217 °C. Source: Mangrove-derived fungus Aspergillus terreus GWQ-48 from unidentified mangrove (rhizospehere soil, Fujian Province, China, first time MNP), various terrestrial lichen spp. Pharm: Antiviral (IFV H1N1 virus inhibitor, IC50 = 94.42 μmol/L, significant). Ref: P. Karrer,et al, Helv. Chim. Acta, 1926, 9, 446│H. Gao, et al, Bioorg. Med. Chem. Lett., 2013, 23, 1776│S. Z. Moghadamtousi, et al, Mar. Drugs, 2015, 13, 4520 (rev) O O

OH O

591 Rubrolide A Type: Pulvinone group. C17H8Br4O4 Red amorph. solid (Me2CO). Source: Ascidians Ritterella rubra, Synoicum blochmanni and Synoicum prunum (Australia). Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275│A. R. Carroll, et al, JOC, 1999, 64, 2680 O O

Br

Br HO Br

OH Br

2.2 Diaryl Derivatives

197

592 Rubrolide B Type: Pulvinone group. C17H7Br4ClO4 Red amorph. solid (Me2CO). Source: Ascidians Ritterella rubra and Synoicum blochmanni. Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275 O Cl O

Br

Br HO Br

OH Br

593 Rubrolide C Type: Pulvinone group. C17H10Br2O4 Red amorph. solid (Me2CO). Source: Ascidians Ritterella rubra and Synoicum blochmanni. Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275│J. Boukouvalas, et al, Tet. Lett., 1998, 39, 7665 O O

Br OH

HO Br

594 Rubrolide D Type: Pulvinone group. C17H10Br2O4 Source: Ascidian Ritterella rubra. Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275 O

Br

HO

O

3'

5'

Br

OH

595 Rubrolide E Type: Pulvinone group. C17H12O4 Yellow solid, mp 278–281 °C. Source: Ascidian Synoicum globosum (Algoa Bay, South Africa), Ritterella rubra and Synoicum

198

2 Aromatic Metabolites

blochmanni. Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275│J. Boukouvalas, et al, Tet. Lett., 1998, 39, 7665│J. Sikorska, et al, JNP, 2012, 75, 1824 O

2

O

HO

4' 4''

OH

596 Rubrolide F Type: Pulvinone group. C18H14O4 Yellow solid. Source: Ascidians Synoicum globosum (Algoa Bay, South Africa) and Ritterella rubra. Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275│J. Sikorska, et al, JNP, 2012, 75, 1824 O O

HO O

597 Rubrolide G Type: Pulvinone group. C17H10Br4O5 Source: Ascidian Ritterella rubra. Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275 O 2

O

Br

Br OH

HO HO Br

Br

598 Rubrolide H Type: Pulvinone group. C17H9Br4ClO5 Source: Ascidian Ritterella rubra. Pharm: PP1 inhibitor (moderate but selective); PP2A inhibitor (moderate but selective). Ref: S. Miao, et al, JOC, 1991, 56, 6275

2.2 Diaryl Derivatives

199

O Cl

2

Br

O

Br

OH

HO HO Br

Br

599 Rubrolide I Type: Pulvinone group. C17H8Br3ClO4 Orange-yellow powder. Source: Ascidian Synoicum blochmanni (Spain). Pharm: Cytotoxic (HT29, ED50 = 5.0 μg/mL). Ref: M. J. Ortega, et al, Tetrahedron, 2000, 56, 3963 Cl

O O Br

HO Br

OH Br

600 Rubrolide K Type: Pulvinone group. C17H9Br2ClO4 Orange amorph. solid. Source: Ascidian Synoicum blochmanni (Spain). Pharm: Cytotoxic (P388, ED50 = 2.5 μg/mL, A549, ED50 = 2.5 μg/mL, HT29, ED50 = 1.2 μg/mL). Ref: M. J. Ortega, et al, Tetrahedron, 2000, 56, 3963 Cl

O O

HO Br

OH Br

601 Rubrolide L Type: Pulvinone group. C17H9Br2ClO4 Reddish-orange amorph. solid. Source: Ascidian Synoicum blochmanni (Spain). Pharm: Cytotoxic (P388, ED50 = 5 μg/mL, A549, ED50 = 5 μg/mL, HT29, ED50 = 2.5 μg/mL, MEL28, ED50 = 5 μg/mL). Ref: M. J. Ortega, et al, Tetrahedron, 2000, 56, 3963

200

2 Aromatic Metabolites

O

Cl

O Br

HO

OH Br

602 Rubrolide M Type: Pulvinone group. C17H10BrClO4 Orange amorph. solid. Source: Ascidian Synoicum blochmanni (Spain). Pharm: Cytotoxic (P388, ED50 = 1.2 μg/mL, A549, ED50 = 1.2 μg/mL, HT29, ED50 = 1.2 μg/mL, MEL28, ED50 = 1.2 μg/mL). Ref: M. J. Ortega, et al, Tetrahedron, 2000, 56, 3963 O

Cl

O

HO OH Br

603 Rubrolide O Type: Pulvinone group. C17H9Br2ClO4 Amorph. yellow solid. Source: Ascidian Synoicum sp. Pharm: Anti-inflammatory (9:1 ratio of Z/E isomers, inhibits superoxide production by hmn neutrophils in vitro, IC50 = 35 μmol/L, no short-term toxicity); anti-inflammatory (inhibits PMA-induced adhesion of neutrophils to microtitre plate); antiproliferative (48 h exposure MTT-detected assay, IC50 = 33 μmol/L). Ref: A. N. Pearce, et al, JNP, 2007, 70, 111 Cl Br HO

O 2

O

3'

5'

Br

OH

604 Carbamidocyclophane A Type: Cylindrocyclophane derivatives. C38H54Cl4N2O8 [α]D22 = −1.2° (c = 0.4, MeOH). Source: Cyanobacterium Nostoc sp. CAVN 10. Pharm: Antibacterial (Staphylococcus aureus ATCC 6538, MIC = 0.1 mmol/L); cytotoxic (MCF7, IC50 = 0.86 μmol/L, hmn amniotic epithelial cell line Fl, IC50 = 3.3 μmol/L). Ref: H. T. N. Bui, et al, JNP, 2007, 70, 499

2.2 Diaryl Derivatives

Cl

30

201

NH2

O 1

Cl

OH

HO

O

O

OH

HO

Cl

14

H 2N

O

34

Cl

605 Carbamidocyclophane B Type: Cylindrocyclophane derivatives. C38H55Cl3N2O8 [α]D22 = −0.3° (c = 0.34, MeOH). Source: Cyanobacterium Nostoc sp. CAVN 10. Pharm: Antibacterial (Staphylococcus aureus ATCC 6538, MIC = 0.04 mmol/L); cytotoxic (MCF7, IC50 = 1.8 μmol/L, hmn amniotic epithelial cell line Fl, IC50 = 4.2 μmol/L). Ref: H. T. N. Bui, et al, JNP, 2007, 70, 499 Cl

30

NH2

O 1

Cl

OH

HO

O

O

OH

HO

Cl

14

H 2N

34

O

606 Carbamidocyclophane C Type: Cylindrocyclophane derivatives. C38H56Cl2N2O8 [α]D22 = +8.5° (c = 0.56, MeOH). Source: Cyanobacterium Nostoc sp. CAVN 10. Pharm: Antibacterial (Staphylococcus aureus ATCC 6538, MIC = 0.06 mmol/L); cytotoxic (MCF7, IC50 = 2.2 μmol/L, hmn amniotic epithelial cell line Fl, IC50 = 5.1 μmol/L). Ref: H. T. N. Bui, et al, JNP, 2007, 70, 499 Cl

O 30

Cl

OH

HO

O

O

HO 14

H 2N

NH2

1

OH 34

O

607 Carbamidocyclophane D Type: Cylindrocyclophane derivatives. C38H57ClN2O8 [α]D22 = +5.6° (c = 0.26, MeOH). Source: Cyanobacterium Nostoc sp. CAVN 10. Pharm: Antibacterial (Staphylococcus aureus); cytotoxic (MCF7 and hmn amniotic epithelial cell line Fl). Ref: H. T. N. Bui, et al, JNP, 2007, 70, 499

202

2 Aromatic Metabolites

O 30

NH2

1

OH

HO

Cl

O

O

OH

HO

34

14

H 2N

O

608 Carbamidocyclophane E Type: Cylindrocyclophane derivatives. C38H58N2O8 [α]D22 = +5.7° (c = 0.12, MeOH). Source: Cyanobacterium Nostoc sp. CAVN 10. Pharm: Antibacterial (Staphylococcus aureus); cytotoxic (MCF7 and han amniotic epithelial cell line Fl). Ref: H. T. N. Bui, et al, JNP, 2007, 70, 499 O 30

NH2

1

OH

HO

O

O

OH

HO

34

14

H 2N

O

609 Cylindrocyclophane A Type: Cylindrocyclophane derivatives. C36H56O6 Cryst., mp 276–278 °C, [α]D = −20° (c = 0.5, MeOH). Source: Cyanobacteria Cylindrospermum licheniforme ATCC 29204 and Nostoc sp. UIC 10022A. Pharm: 20S-proteasome inhibitor (IC50 = 33.9 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L). Ref: B. S. Moore, et al, Tetrahedron, 1992, 48, 3001│G. E. Chlipala, et al, JNP, 2010, 73, 1529 OH 30

1

OH

HO

HO 14

OH 34

HO

610 Cylindrocyclophane A1 Type: Cylindrocyclophane derivatives. C36H55ClO6 Amorph. powder. Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm: 20S-proteasome inhibitor (IC50 = 27.6 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529

2.2 Diaryl Derivatives

203

OH 30

Cl

1

OH

HO

OH

HO

34

14

HO

611 Cylindrocyclophane A2 Type: Cylindrocyclophane derivatives. C36H54Cl2O6 Amorph. powder, [α]D = −26° (c = 0.07, MeOH). Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm: 20Sproteasome inhibitor (IC50 = 2.55 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L); cytotoxic (HT29, EC50 = 1.7 μmol/L, Positive control Camptothecin, EC50 = 60 nmol/ L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529 Cl

OH 30

Cl

1

OH

HO

OH

HO

34

14

HO

612 Cylindrocyclophane A3 Type: Cylindrocyclophane derivatives. C36H53Cl3O6 Amorph. powder, [α]D = −27° (c = 0.06, MeOH). Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm: 20S-proteasome inhibitor (IC50 = 2.75 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L); cytotoxic (HT29, EC50 = 0.5 μmol/L, Positive control Camptothecin, EC50 = 60 nmol/L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529 Cl

30

OH 1

Cl

OH

HO

HO

OH

Cl

14

HO

34

613 Cylindrocyclophane A4 Type: Cylindrocyclophane derivatives. C36H52Cl4O6 Amorph. powder, [α]D = −26° (c = 0.2, MeOH). Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm: 20S-proteasome inhibitor (IC50 = 3.93 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L); cytotoxic

204

2 Aromatic Metabolites

(HT29, EC50 = 2.0 μmol/L, Positive control Camptothecin, EC50 = 60 nmol/L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529 Cl

30

OH 1

Cl

OH

HO

OH

HO

Cl

14

HO

34

Cl

614 Cylindrocyclophane AB4 Type: Cylindrocyclophane derivatives. C36H52Br4O6 Amorph. powder, [α]D = −45° (c = 0.04, MeOH). Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm: 20Sproteasome inhibitor (IC50 = 2.23 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L); cytotoxic (HT29, EC50 = 0.5 μmol/L, Positive control Camptothecin, EC50 = 60 nmol/L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529 Br

30

OH 1

Br

OH

HO

OH

HO

Br

14

HO

34

Br

615 Cylindrocyclophane C Type: Cylindrocyclophane derivatives. C36H56O5 [α]D = −40° (c = 0.1, MeOH). Source: Cyanobacteria Cylindrospermum licheniforme ATCC 29204 and Nostoc sp. UIC 10022A. Pharm: 20S-proteasome inhibitor (IC50 = 59.3 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L). Ref: B. S. Moore, et al, Tetrahedron, 1992, 48, 3001│G. E. Chlipala, et al, JNP, 2010, 73, 1529 OH 30

1

OH

HO

HO

OH 34

14

616 Cylindrocyclophane C2 Type: Cylindrocyclophane derivatives. C36H54Cl2O5 Amorph. powder, [α]D = −37° (c = 0.15, MeOH). Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm:

2.2 Diaryl Derivatives

205

20S-proteasome inhibitor (IC50 = 22.8 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L); cytotoxic (HT29, EC50 = 0.9 μmol/L, Positive control Camptothecin, EC50 = 60 nmol/ L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529

1 30

OH

HO

OH

HO

Cl

14

HO

34

Cl

617 Cylindrocyclophane C4 Type: Cylindrocyclophane derivatives. C36H52Cl4O5 Amorph. powder, [α]D = −40° (c = 0.03, MeOH). Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm: 20Sproteasome inhibitor (IC50 = 11.2 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L); cytotoxic (HT29, EC50 = 2.8 μmol/L, Positive control Camptothecin, EC50 = 60 nmol/ L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529

Cl

30 1

Cl

OH

HO

OH

HO

Cl

14

HO

34

Cl

618 Cylindrocyclophane F Type: Cylindrocyclophane derivatives. C36H56O4 [α]D = −72° (c = 0.9, MeOH). Source: Cyanobacteria Cylindrospermum licheniforme ATCC 29412 and Nostoc sp. UIC 10022A. Pharm: 20S-proteasome inhibitor (IC50 > 100 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L). Ref: B. S. Moore, et al, Tetrahedron, 1992, 48, 3001│G. E. Chlipala, et al, JNP, 2010, 73, 1529

1 30

OH

HO

HO 14

OH 34

206

2 Aromatic Metabolites

619 Cylindrocyclophane F4 Type: Cylindrocyclophane derivatives. C36H52Cl4O4 Amorph. powder. Source: Cyanobacterium Nostoc sp. UIC 10022A. Pharm: 20S-proteasome inhibitor (IC50 = 44.8 μmol/L, control Bortezomib, IC50 = 2.5 nmol/L). Ref: G. E. Chlipala, et al, JNP, 2010, 73, 1529 Cl

30 1

Cl

OH

HO

OH

HO

Cl

14 34

Cl

620 Nostocyclophane A Type: Cylindrocyclophane derivatives. C48H74Cl2O16 Oil, [α]D25 = −12° (c = 0.1, MeOH). Source: Cyanobacterium Nostoc linckia UTEX B1932. Pharm: Cytotoxic (KB, LoVo, IC50 = 1–2 μg/mL). Ref: B. S. Moore, et al, JACS, 1990, 112, 4061│J. L. Chen, et al, JOC, 1991, 56, 4360 O 1

HO

Cl

O

HO

OH

O

HO

Cl

O OH

OH OH

O

13

26

O

OH

OH

OH

621 Nostocyclophane B Type: Cylindrocyclophane derivatives. C42H64Cl2O11 Oil, [α]D25 = −3.7° (c = 0.25, MeOH). Source: Cyanobacterium Nostoc linckia UTEX B1932. Pharm: Cytotoxic (KB, LoVo, IC50 = 1–2 μg/mL). Ref: B. S. Moore, et al, JACS, 1990, 112, 4061│J. L. Chen, et al, JOC, 1991, 56, 4360 O 1

Cl

HO 13

22

HO

OH

Cl HO O

O

O

OH OH

OH

2.3 Tropolone Derivatives

207

622 Nostocyclophane C Type: Cylindrocyclophane derivatives. C35H52Cl2O6 Oil, [α]D25 = −5.53° (c = 0.27, MeOH). Source: Cyanobacterium Nostoc linckia UTEX B1932. Pharm: Cytotoxic (KB, LoVo, IC50 = 1–2 μg/mL). Ref: B. S. Moore, et al, JACS, 1990, 112, 4061│J. L. Chen, et al, JOC, 1991, 56, 4360 HO 1

Cl

OH

HO 13

22

HO

OH

Cl O

623 Nostocyclophane D Type: Cylindrocyclophane derivatives. C36H54Cl2O6 Cryst. (EtOH aq), mp 242–243 °C, [α]D25 = +10.8° (c = 0.4, MeOH). Source: Cyanobacterium Nostoc linckia UTEX B1932. Pharm: Cytotoxic (KB, LoVo, IC50 = 0.5 μg/mL). Ref: B. S. Moore, et al, JACS, 1990, 112, 4061│J. L. Chen, et al, JOC, 1991, 56, 4360 O 1

Cl

OH

HO 13

22

OH

HO

Cl O

2.3 Tropolone Derivatives 624 Thiotropocin 4-Hydroxy-8-thioxocyclohept[c][1,2]oxathiol-3(8H)-one; Antibiotic CB 104 Type: Tropolone derivatives. C8H4O3S2 Fine orange needles, mp 222–225 °C (dec), mp 300 °C, Source: Marine-derived bacterium Caulobacter sp. PK654. Pharm: Antibacterial (gram-positive and -negative bacteria), antifungal; antimycoplasmas, LD50 (mus, orl) = 50–100 mg/kg. Ref: Y. Kawano, et al, J. Mar. Biotechnol., 1997, 5, 225; 1998, 6, 49 S S O O OH

208

2 Aromatic Metabolites

625 Tropolone 2-Hydroxy-2,4,6-cycloheptatrien-1-one Type: Tropolone derivatives. C7H6O2 Needles (hexane or petrol), mp 49–50 °C. Source: Marine-derived bacterium Phaeobacter gallaciensis DSM17395. Pharm: LD50 (rat, ipr) = 190 mg/kg. Ref: V. Thiel, et al, Org. Biomol. Chem., 2010, 8, 234 O OH

2.4 Benzofuranoids 626 6,7-Dihydro-3-(hydroxymethyl)-6-methyl-4(5H)-benzofuranone Type: Benzofurans. C10H12O3 Source: Marine-derived fungus Phomopsis sp. hzla01-1 (from unidentified marine origin). Pharm: Antibacterial (Escherichia coli, Candida albicans, Saccharomyces cerevisiae, Bacillus subtilis). Ref: X. P. Du, et al, J. Antibiot., 2008, 61, 250 O

OH

O

627 Felinone B Type: Benzofurans. C12H14O3 Source: Marine-derived fungus Beauveria felina EN-135 (entomopathogenic). Pharm: Antibacterial (Pseudomonas aeruginosa, MIC = 32 μg/mL). Ref: F. Y. Du, et al, Mar. Drugs, 2014, 12, 2816 HO

OH O

628 Isoacremine D Type: Benzofurans. C12H14O3 Source: Marine-derived fungus Myceliophthora lutea. Pharm: Antibacterial (Staphylococcus aureus, MIC = 200 μg/mL). Ref: O. F. Smetanina, et al, Chem. Nat. Compd., 2011, 47, 385 HO OH O

2.4 Benzofuranoids

209

629 Phialofurone Type: Benzofurans. C14H16O4 Yellow powder, [α]D20 = −4.9° (c = 0.16, MeOH). Source: Marine-derived fungus Phialocephala sp. (deep sea sediment, East Pacific Ocean). Pharm: Cytotoxic (P388, IC50 = (0.2 ± 0.01)μmol/L, control cis-Diaminedichloroplatinum (CDDP), IC50 = (0.04 ± 0.03)μmol/L; K562, IC50 = (22.4 ± 0.9)μmol/L, cisDiaminedichloroplatinum (CDDP), IC50 = (0.08 ± 0.05)μmol/L). Ref: D. -H. Li, et al, Chem. Biodiversity, 2011, 8, 895

O

O O

HO

630 Thelepin Type: Benzofurans. C14H9Br3O3 Pale yellow cryst. (MeOH), mp 202–203 °C. Source: Annelid worm Thelepus setosus. Pharm: Antifungal. Ref: T. Higa, et al, Tetrahedron, 1975, 31, 2379│O. Tsuge, et al, Chem. Lett., 1984, 1415 Br HO O O Br

Br

631 Ustusorane E Type: Benzofurans. C15H22O4 Amorph. solid, [α]D20 = −11° (c = 0.1, MeOH). Source: Mangrove-derived fungus Aspergillus ustus 094102 from mangrove Bruguiera gymnorrhiza (rhizosphere soil, Wenchang, Hainan, China). Pharm: Cytotoxic (A549, IC50 > 100 μmol/L, control VP-16, IC50 = 0.63 μmol/L; HL60, IC50 = 0.13 μmol/L, VP-16, IC50 = 0.042 μmol/L). Ref: Z. Lu, et al, JNP, 2009, 72, 1761 OH

OH O OH

632 (±)-Acetophthalidin 3-Acetyl-5,7-dihydroxy-1(3H)-isobenzofuranone Type: Isobenzofurans. C10H8O5 Powder, mp 213–2215 °C (dec), mp 195–205 °C Source: Marine-derived fungus Aspergillus sp. (from sediment). Pharm: Cytotoxic; mammalian cell cycle inhibitor (tsFT210, 6.25 μg/mL, caused complete arrest in G2/M phase). Ref: C. -B. Cui, et al, J. Antibiot.,

210

2 Aromatic Metabolites

1996, 49, 216│S. Nomoto, et al, Liebigs Ann., 1997, 721│T. S. Bugni, et al, NPR, 2004, 21, 143 (rev) OH

O O

HO O

633 3-Acetyl-7-hydroxy-5-methoxy-3,4-dimethyl-1(3H)-isobenzofuranone Type: Isobenzofurans. C13H14O5 Needles, [α]D29 = +200° (c = 0.05, EtOH). Source: Marine-derived fungi Halorosellinia oceanica BCC5149 and Leptosphaeria sp. KTC 727. Pharm: Antituberculosis (Mycobacterium tuberculosis, MIC = 200 μg/mL, weak). Ref: M. Chinworrungsee, et al, JCS Perkin I, 2002, 2473│W. C. Tayone, et al, JNP, 2011, 74, 425 O O O

OH

O

634 Ascolactone B Type: Isobenzofurans. C15H16O7 Amorph. solid, [α]D25 = −169.2° (c = 0.5, MeOH). Source: Marine-derived fungus Ascochyta salicorniae from green alga Ulva sp. (North Sea coast, Germany). Pharm: PPs inhibitors (MPtpB (mycobacterial protein tyrosine phosphatase B), IC50 = 95.0 μmol/L; Cdc25a, PTP1B, VHR, MPtpA and VEPTP, all inactive). Ref: S. F. Seibert, et al, Org. Biomol. Chem., 2006, 4, 2233 O HO 3

O

O OH

OH

O

635 3-Butyl-7-methoxyphthalide Type: Isobenzofurans. C13H16O3 Viscous liquid, [α]D27 = −49.1° (c = 1.8, CHCl3). Source: An unidentified marine-derived fungus CRIF2 (order Pleosporales) from an unidentified sponge (Thailand). Pharm: Cytotoxic (several cell lines). Ref: V. Prachyawarakorn, et al, Planta Med., 2008, 74, 69

2.4 Benzofuranoids

O

211

O O

636 Corollosporin 3-Hexyl-3,7-dihydroxy-1(3H)-isobenzofuranone Type: Isobenzofurans. C14H18O4 Cryst. (hexane/EtOAc), mp 79.5–81.5 °C. Source: Marine-derived fungus Corollospora maritima. Pharm: Antibacterial. Ref: K. Liberra, et al, Pharmazie, 1998, 53, 578 OH O

OH

O

637 Cytosporone E Type: Isobenzofurans. C15H22O5 Source: Mangrove-derived fungus Leucostoma persoonii from mangrove Rhizophora mangle (branch, Everglades, Florida), Cytospora sp. Pharm: Antiplasmodial (Plasmodium falciparum, IC90 = 13 μmol/L, to A549 cytotoxic IC90 = 437 μmol/L, 90% inhibition therapeutic index TI90 = 33); antibacterial (MRSA, MIC = 72 μmol/L, minimum bactericidal concentration MBC90 = 45 μmol/L, minimum biofilm eradication counts MBEC90 = 39 μmol/L; A549 IC50 = 280 μmol/L, IC90 = 440 μmol/L). Ref: M. P. Singh, et al, Mar. Drugs, 2007, 5, 71│ J. Beau, et al, Mar. Drugs, 2012, 10, 762 O HO O HO OH

638 Diaporthelactone Type: Isobenzofurans. C11H10O4 Cryst. (EtOAc). Source: Marine-derived fungus Diaporthe sp. HLY2. Pharm: Cytotoxic (KB, IC50 = 6.25 μg/mL; Raji cell lines, IC50 = 5.51 μg/mL). Ref: X. Lin, et al, FEMS Microbiol. Lett., 2005, 251, 53 O O

O O

212

2 Aromatic Metabolites

639 Epicoccone Type: Isobenzofurans. C9H8O5 Cryst., mp 249–250 °C. Source: Marine-derived fungus Epicoccum sp. from brown alga Fucus vesiculosus, terrestrial fungus (Epicoccum purpurascens MYC 1097). Pharm: Antioxidant (DPPH scavenger, 25 μg/mL, ScRt = 95%; inhibits peroxidation of linolenic acid, TBARS assay, 37 μg/mL, InRt = 62%). Ref: A. Abdel-Lateff, et al, Planta Med., 2003, 69, 831│N. H. Lee, et al, Bull. Korean Chem. Soc., 2007, 28, 877│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) OH HO O HO O

640 Marilone A Type: Isobenzofurans. C21H28O4 Transparent oil. Source: Marine-derived fungus Stachylidium sp. from sponge Callyspongia flammea (Bear I., Sydney, Australia). Pharm: Antiplasmodial (Plasmodium berghei, liver stages, IC50 = 12.1 μmol/L); cytotoxic (NCI-H460, MCF7 and SF268, average GI50 = 36.7 μmol/L, weak antiproliferative). Ref: C. Almeida, et al, Beilstein J. Org. Chem., 2011, 7, 1636

O O O

O

641 Marilone B Type: Isobenzofurans. C11H12O4 White amorph. solid. Source: Marine-derived fungus Stachylidium sp. from sponge Callyspongia flammea (Bear I., Sydney, Australia). Pharm: Selective antagonist of serotonin receptor 5-HT2B (Ki = 7.7 μmol/L). Ref: C. Almeida, et al, Beilstein J. Org. Chem., 2011, 7, 1636

OH O O

O

642 Marilone C Type: Isobenzofurans. C20H26O4 Transparent oil. Source: Marine-derived fungus Stachylidium sp. from sponge Callyspongia flammea (Bear I., Sydney, Australia).

2.4 Benzofuranoids

213

Pharm: Cytotoxic (NCI-H460, MCF7 and SF268, average GI50 = 26.6 μmol/L, weak, antiproliferative). Ref: C. Almeida, et al, Beilstein J. Org. Chem., 2011, 7, 1636 O O O

O

643 Mycophenolic acid Type: Isobenzofurans. C17H20O6 Needles (H2O), mp 141 °C. Source: Terrestrial fungi Penicillium spp. Pharm: Antineoplastic; antiviral; immunosuppressant; used in treating psoriasis and leishmaniasis; used in prophylaxis of acute kidney rejection. Ref: CRC Press, DNP on DVD, 2012, version20.2 OH

COOH

O O

O

644 Paecilocin A Type: Isobenzofurans. C16H22O3 White amorph. powder, [α]D25 = −8.6° (c = 0.25,CHCl3). Source: Marine-derived fungus Paecilomyces variotii from scyphomedusa Neopilema nomurai (Southern coast of R. O. Korea). Pharm: Antibacterial (Staphylococcus aureus SG 511, MIC > 40 μg/mL, control Tetracycline, MIC = 1.25 μg/mL; MRSA 3089, MIC > 40 μg/mL, control Vancomycin, MIC = 0.625 μg/mL; MDR Vibrio parahemolyticus 7001, MIC > 40 μg/mL, control Levofloxacin, MIC = 0.156 μg/mL). Ref: J. Liu, et al, JNP, 2011,74, 1826 H O

OH

O

645 Paecilocin B Type: Isobenzofurans. C18H28O4 Yellow oil, [α]D25 = −4.1° (c = 0.10, MeOH). Source: Marine-derived fungus Paecilomyces variotii from scyphomedusa Neopilema nomurai (Southern coast of R. O. Korea). Pharm: Antibacterial (Staphylococcus aureus SG 511, MIC = 5 μg/mL, control Tetracycline, MIC = 1.25 μg/mL; MRSA 3089, MIC = 20 μg/mL, control Vancomycin, MIC = 0.625 μg/mL; MDR Vibrio parahemolyticus

214

2 Aromatic Metabolites

7001, MIC > 40 μg/mL, control Levofloxacin, MIC = 0.156 μg/mL). Ref: J. Liu, et al, JNP, 2011,74, 1826 O O 1S*

O

OH

646 Paecilocin C Type: Isobenzofurans. C18H28O4 Yellow oil, [α]D25 = −12.6° (c = 0.10, MeOH). Source: Marine-derived fungus Paecilomyces variotii from scyphomedusa Neopilema nomurai (Southern coast of R. O. Korea). Pharm: Antibacterial (Staphylococcus aureus SG 511, MIC = 20 μg/mL, control Tetracycline, MIC = 1.25 μg/mL; MRSA 3089, MIC = 40 μg/mL, control Vancomycin, MIC = 0.625 μg/mL; MDR Vibrio parahemolyticus 7001, MIC > 40 μg/mL, control Levofloxacin, MIC = 0.156 μg/mL). Ref: J. Liu, et al, JNP, 2011,74, 1826 O O 1R*

O

OH

647 Pestaliopen A Type: Isobenzofurans. C27H33ClO10 Source: Mangrove-derived fungus Pestalotiopsis sp. (endophytic) from mangrove Rhizophora mucronata (leaves, Hainan, China). Pharm: Antibacterial (Enterococcus faecalis, modest). Ref: Y. Hemberger, et al, Chem. -Eur. J., 2013, 19, 15556 O O

O

Cl

O

O OH

O

OH

O O

H

648 Purpurester A Type: Isobenzofurans. C13H16O5 Source: Acid-tolerant fungus Penicillium purpurogenum JS03-21 (region of red soil by Lujiang River, Yunnan, China). Pharm: Antiviral (IFV virus, IC50 = 85.3 μmol/L). Ref: H. Wang, et al, JNP, 2011, 74, 2014

2.5 Benzopyranoids

215

O HO O O

HO

649 Talaroflavone Type: Isobenzofurans. C14H12O6 Flakes, mp 230 °C (dec), [α]D = +181° (c = 0.74, MeOH). Source: Marine-derived unidentified fungus from unidentified algae (Japan waters), terrestrial fungus (Talaromyces flavus). Pharm: Eukaryotic DNA polymerases selective inhibitor (X and Y families); inhibitor inactive (other eukaryotic or prokaryotic polymerases, or other DNA metabolic enzymes). Ref: W. A. Ayer, et al, Can. J. Chem., 1990, 68, 2085│M. Naganuma, et al, BoMC, 2008, 16, 2939 O HO O O O

OH

2.5 Benzopyranoids 650 Aflatoxin B2b Type: 1-Benzopyrans. C22H20O10 Source: Mangrove-derived fungus Aspergillus flavus 092008 from semimangrove Hibiscus tiliaceus (root, Wenchang, Hainan, China). Pharm: Antibacterial (Enterobacter coli, MIC = 22.5 μmol/L, Bacillus subtilis, MIC = 1.7 μmol/L, Enterobacter aerogenes, MIC = 1.1 μmol/L). Ref: H. Wang, et al, Arch. Pharmacal Res., 2012, 35, 1387 O

O

O

O O O

H

O

O H

O

O

651 Ammonificin C Type: 1-Benzopyrans. C23H20BrNO6 [α]D24 = −45° (c = 0.8, MeOH). Source: Marinederived bacterium Thermovibrio ammonificans (hydrothermal vent, East Pacific Rise). Pharm: Apoptosis inducer (2 μmol/L, control Staurosporine, 0.1 μmol/L). Ref: E. H. Andrianasolo, et al, Mar. Drugs, 2012, 10, 2300

216

2 Aromatic Metabolites

HO

NH2

OH

O

O OH

Br OH

652 Ammonificin D Type: 1-Benzopyrans. C23H19Br2NO5 [α]D24 = −45° (c = 0.8, MeOH). Source: Marinederived bacterium Thermovibrio ammonificans (hydrothermal vent, East Pacific Rise). Pharm: Apoptosis inducer (3 μmol/L, control Staurosporine, 0.1 μmol/L). Ref: E. H. Andrianasolo, et al, Mar. Drugs, 2012, 10, 2300 HO

NH2

OH

O

O OH

Br Br

653 Antibiotic SB236049 Type: 1-Benzopyrans. C14H9NO6 Yellow solid. Source: Fungus Chaetomium funicola TCF 6040. Pharm: Metallo-β-lactamase inhibitor (metallo-β-lactamase of Bacteroides fragilis CfiA, Ki = 15 μmol/L); metallo-β-lactamase inhibitor (metalloβ-lactamase of Bacillus cereus II, Zn2+ 1 μmol/L, IC50 = 0.3 μmol/L; Zn2+ 100 μmol/ L, IC50 = 0.7 μmol/L; metallo-β-lactamase of Bacteroides fragilis CfiA, Zn2+ 100 μmol/L, IC50 = 2 μmol/L; metallo-β-lactamase of Pseudomonas aeruginosa IMP-1, Zn2+ 100 μmol/L, IC50 = 151 μmol/L; metallo-β-lactamase of L-1, Zn2+ 100 μmol/L, IC50 > 1000 μmol/L; angiotensin-converting enzyme ACE, Zn2+ 1 μmol/L, IC50 > 333 μmol/L). Ref: D. J. Payne, et al, Antimicrob. Agents Chemother., 2002, 46, 1880 O

OH

O

HO

HO

N O

2.5 Benzopyranoids

217

654 Apralactone A Type: 1-Benzopyrans. C18H20O6 Amorph. solid, [α]D20 = +10° (c = 0.3, 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 = 9.87 μmol/L BXF-1218L, IC50 = 12.3 μmol/L; BXF-T24, IC50 = 6.36 μmol/L; CNXFSF268, IC50 = 6.85 μmol/L; CXF-HCT116, IC50 = 9.59 μmol/L; CXF-HT29, IC50 = 10.26 μmol/L; GXF-251L, IC50 = 9.35 μmol/L; LXF-1121L, IC50 = 11.43 μmol/L; LXF289L, IC50 = 15.77 μmol/L; LXF-526L, IC50 = 4.61 μmol/L; LXF-629L, IC50 = 9.71 μmol/L; LXF-H460, IC50 = 6.74 μmol/L; MAXF-401NL, IC50 = 9.17 μmol/L; MAXF-MCF7, IC50 = 10.11 μmol/L; MEXF-276L, IC50 = 9.03 μmol/L; MEXF-462NL, IC50 = 12.2 μmol/L; MEXF-520L, IC50 = 7.66 μmol/L; OVXF-899L, IC50 = 9.56 μmol/L; OVXF-OVCAR3, IC50 = 10.97 μmol/L; PAXF-1657L, IC50 = 13.25 μmol/L; PAXF-PANC1, IC50 = 11.43 μmol/L; PRXF-22RV1, IC50 = 7.66 μmol/L; PRXF-DU145, IC50 = 7.94 μmol/L; PRXF-LNCAP, IC50 = 9.52 μmol/L; PRXF-PC3M, IC50 = 10.05 μmol/L; PXF-1752L, IC50 = 16.78 μmol/L; RXF-1781L, IC50 = 16.57 μmol/L; RXF-486L, IC50 = 12.64 μmol/L; UXF-1138L, IC50 = 10.11 μmol/L). Ref: H. Greve, et al, EurJOC, 2008, 5085 O O O

O

HO

OH

655 Aspergillitine Type: 1-Benzopyrans. C15H13NO2 Yellow powder (MeOH). Source: Marine-derived fungus Aspergillus versicolor from sponge Xestospongia exigua (Mengangan I., Bali, Indonesia, Sep 1997). Pharm: Antibacterial (Bacillus subtilis, moderate). Ref: W. Lin, et al, JNP, 2003, 66, 57 O

O N

656 Caffeoylate ester Type: 1-Benzopyrans. C24H18O8 Source: Mangrove Laguncularia racemosa. Pharm: Antioxidant (significant); hmn kinases inhibitor (FLT3 and SAK, moderate). Ref: C. Shi, et al, Phytochemistry, 2010, 71, 435

218

2 Aromatic Metabolites

HO

O

O OH

O

O

HO

HO

657 Chromanone A Type: 1-Benzopyrans. C12H12O4 Source: Marine-derived fungus Penicillium sp. from green alga Ulva sp. (Suez Canal, Egypt). Pharm: Antioxidant (hydroxyl radical scavenger, potent); inhibits cytochrome P450 1A (CYP1A); glutathione S-transferases (GST) inhibitor; enzymes inducer (epoxide hydrolase, glutathione S-transferase, enzymes involved in carcinogen metabolism). Ref: A. M. Gamal-Eldeen, et al, Environ. Toxicol. Pharmacol., 2009, 28, 317 O

OH

O O

658 Chromenol 2-Methyl-2-(prenylmethyl)-2H-1-benzopyran-6-ol Type: 1-Benzopyrans. C16H20O2 Light yellow oil. Source: Ascidian Aplidium constellatum. Pharm: Anti-inflammatory. Ref: N. M. Targett, et al, JNP, 1984, 47, 556 O

HO

659 (±)-Dictyochromenol Type: 1-Benzopyrans. C21H28O2 Oil. Source: Brown alga Dictyopteris undulata. Pharm: Ichthyotoxin (27 ppm). Ref: M. -N, Dave, et al, Heterocycles, 1984, 22, 2301 O

HO

2.5 Benzopyranoids

219

660 (2R)-2,3-Dihydro-7-hydroxy-6,8-dimethyl-2-[(E)-prop-l-enyl]chromen-4-one Type: 1-Benzopyrans. C14H16O3 Yellow meedles, [α]D20 = +44.5° (c = 0.10, MeOH). Source: Deep-sea fungus Aspergillus sydowi YH11-2 (Guam, depth of 1000 m, E144°43′ N13°26′). Pharm: Cytotoxic (P388, IC50 = 0.14 μmol/L, control CDDP, IC50 = 0.039 μmol/L). Ref: L. Tian, et al, Arch. Pharm. Res,. 2007, 30, 1051 O

HO

O

661 2,3-Dihydro-7-hydroxy-6-methyl-2-(1-propenyl)-4H-1-benzopyran-4-one Type: 1-Benzopyrans. C13H14O3 Source: Marine-derived fungus Trichoderma sp. from starfish Acanthaster planci (Hainan Sanya National Coral Reef Reserve, China). Pharm: Cytotoxic (several HTCLs cells, moderate). Ref: W. -J. Lan, et al, Nat. Prod. Commun., 2012, 7, 1337 O

HO

O

662 2,2-Dimethyl-2H-1-benzopyran-6-ol Type: 1-Benzopyrans. C11H12O2 Cryst. (Et2O/pentane), mp 86–87 °C. Source: Ascidian Aplidium californicum. Pharm: Antimutagenic. Ref: B. M. Howard, et al, Tet. Lett., 1979, 4449 HO

O

663 Monodictyochrome A Type: 1-Benzopyrans. C30H30O11 Yellow solid, [α]D24 = −67° (c = 0.42, CHCl3). Source: Marine-derived fungus Monodictys putredinis. Pharm: Cytochrome P450 1A inhibitor (IC50 = 5.3 μmol/L); inducer of NAD(P)H quinone reductase (cultured mouse Hepa1c1c7 cells, CD (concentration required to double the specific activity of quinone reductase) = 22.1 μmol/L, IC50 > 50 μmol/L); aromatase inhibitor (IC50 = 24.4 μmol/L, weak). Ref: A. Pontius, et al, JNP, 2008, 71, 1793

220

2 Aromatic Metabolites

OH

O HO O H

HO

O

O

O O H O O

664 Monodictyochrome B Type: 1-Benzopyrans. C30H30O11 Yellow solid, [α]D24 = +74° (c = 0.6, CHCl3). Source: Marine-derived fungus Monodictys putredinis. Pharm: Cytochrome P450 1A inhibitor (IC50 = 7.5 μmol/L); inducer of NAD(P)H quinone reductase (cultured mouse Hepa1c1c7 cells, CD (concentration required to double the specific activity of QR) = 24.8 μmol/L, IC50 > 50 μmol/L); aromatase inhibitor (IC50 = 16.5 μmol/L, weak). Ref: A. Pontius, et al, JNP, 2008, 71, 1793 O H

O

O OH

O

OH

O HO O H

O

O

665 Oxirapentyne E Type: 1-Benzopyrans. C16H20O5 Source: Marine-derived fungus Isaria felina (sediment, Vietnam). Pharm: Growth stimulant (corn and barley rootlets). Ref: A. N. Yurchenko, et al, Chem. Nat. Compd., 2013, 49, 857 O

O

HO

O

OH

2.5 Benzopyranoids

221

666 Penilactone A Type: 1-Benzopyrans. C25H26O9 Source: Deep-sea fungus Penicillium crustosum PRB-2 (Antarctic Ocean). Pharm: Antineoplastic (weak); cytotoxic (10 mmol/L, NF-κB, InRt = 40%). Ref: G. Wu, et al, Tetrahedron, 2012, 68, 9745

O HO O

OH

OH

O O O

OH

667 Penilactone B Type: 1-Benzopyrans. C26H26O11 Source: Deep-sea fungus Penicillium crustosum PRB-2 (Antarctic Ocean). Pharm: Antineoplastic (weak). Ref: G. Wu, et al, Tetrahedron, 2012, 68, 9745

O

O

HO OH

OH O O O

OH

OH O

668 Penostatin A Type: 1-Benzopyrans. C22H32O3 Needles, mp 73–75 °C, [α]D = +133° (c = 0.2, CHCl3). Source: Marine-derived fungus Penicillium sp. OUPS-79 from green alga Enteromorpha intestinalis. Pharm: Cytotoxic (P388, ED50 = 0.8 μg/mL). Ref: C. Takahashi, et al, Tet. Lett., 1996, 37, 655│C. Iwamoto, et al, Tetrahedron, 1999, 55, 14353 HO 6

H

7

H 9a

9

H O

O

2

222

2 Aromatic Metabolites

669 Penostatin B Type: 1-Benzopyrans. C22H32O3 Powder, mp 63–66 °C, [α]D = −103° (c = 0.5, CHCl3). Source: Marine-derived fungus Penicillium sp. OUPS-79 from green alga Enteromorpha intestinalis. Pharm: Cytotoxic (P388, ED50 = 1.2 μg/mL). Ref: C. Takahashi, et al, Tet. Lett., 1996, 37, 655│C. Iwamoto, et al, Tetrahedron, 1999, 55, 14353 HO H

6

H

7

9a

9

2

O H

O

670 Penostatin C Type: 1-Benzopyrans. C22H30O2 Powder, mp 63–65 °C, [α]D = +120° (c = 1, CHCl3). Source: Marine-derived fungus Penicillium sp. OUPS-79 from green alga Enteromorpha intestinalis. Pharm: Cytotoxic (P388, ED50 = 1.0 μg/mL (1.1 μg/mL); BSY1, ED50 = 2.0 μg/mL; MCF7, ED50 = 1.6 μg/mL; HCC2998, ED50 = 2.0 μg/mL; NCI-H522, ED50 = 2.5 μg/mL; DMS114, ED50 = 1.9 μg/mL; OVCAR-3, ED50 = 2.4 μg/mL; MKN1, ED50 = 1.7 μg/mL). Ref: C. Takahashi, et al, Tet. Lett., 1996, 37, 655│C. Iwamoto, et al, Tetrahedron, 1999, 55, 14353 6

H

H

7

9a

9

2

O

H O

671 Penostatin D Type: 1-Benzopyrans. C22H34O3 Powder, mp 106–110 °C, [α]D = −26.7° (c = 0.1, CHCl3). Source: Marine-derived fungus Penicillium sp. OUPS-79 from green alga Enteromorpha intestinalis. Pharm: Cytotoxic (P388, ED50 = 11.0 μg/mL (11.5 μg/mL)). Ref: C. Takahashi, et al, Tet. Lett., 1996, 37, 655│C. Iwamoto, et al, Tetrahedron, 1999, 55, 14353 HO H

6 7

H 9a

9

OH

H

O

2

2.5 Benzopyranoids

223

672 Pestalotiopsone F Type: 1-Benzopyrans. C17H20O5 Amorph. solid (MeOH). Source: Mangrove-derived fungus Pestalotiopsis sp. JCM2A4 from mangrove Rhizophora mucronata (leaves, Hainan, China). Pharm: Cytotoxic (murine cancer cell line L5178Y, EC50 = 8.93 μg/mL). Ref: J. Xu, et al, JNP, 2009, 72, 662 O O

O

HO

O

673 Sacrochromenol A sulfate Type: 1-Benzopyrans. C36H52O5S Source: Sponges Sarcotragus spinulosus (deepwater) and Ircinia spinosula. Pharm: Na/K-ATPase inhibitor. Ref: V. A. Stonik, et al, JNP, 1992, 55, 1256│L. A. Tziveleka, et al, Chem. Biodiversity, 2005, 2, 901 H O

O 5

O S

H

O

O

674 Sacrochromenol B sulfate Type: 1-Benzopyrans. C41H60O5S Source: Sponge Sarcotragus spinulosus (deepwater). Pharm: Na/K-ATPase inhibitor. Ref: V. A. Stonik, et al, JNP, 1992, 55, 1256

O O

S

H

O 6

H

O

O

675 Sacrochromenol C sulfate Type: 1-Benzopyrans. C46H68O5S Source: Sponge Sarcotragus spinulosus (deepwater). Pharm: Na/K-ATPase inhibitor. Ref: V. A. Stonik, et al, JNP, 1992, 55, 1256

O O

S

H

O 7

H

O

O

676 Trichodermatide B Type: 1-Benzopyrans. C16H24O4 Needles (MeOH), mp 65–68 °C, [α]D20 = +64° (c = 0.05, MeOH). Source: Marine-derived fungus Trichoderma reesei (sediment

224

2 Aromatic Metabolites

sample, China waters). Pharm: Cytotoxic (MTT assay, hmn melanoma A375-S2 cell line, IC50 = 187.3 μg/mL). Ref: Y. Sun, et al, Org. Lett., 2008, 10, 393 O HO H O O

677 Trichodermatide C 2-(1-Heptenyl)-2,3,4,6,7,8-hexahydro-6-hydroxy-5H-1-benzopyran-5-one Type: 1Benzopyrans. C16H24O3 Oil, [α]D20 = +80° (c = 0.02, MeOH). Source: Marinederived fungus Trichoderma reesei (sediment sample, China waters). Pharm: Cytotoxic (MTT assay, hmn melanoma A375-S2 cell line, IC50 = 38.8 μg/mL). Ref: Y. Sun, et al, Org. Lett., 2008, 10, 393 O HO

O

678 Trichodermatide D Type: 1-Benzopyrans. C16H24O4 Oil, [α]D20 = +22.5° (c = 0.01, MeOH). Source: Marinederived fungus Trichoderma reesei (sediment sample, China waters). Pharm: Cytotoxic (MTT assay, hmn melanoma A375-S2 cell line, IC50 = 222.2 μg/mL). Ref: Y. Sun, et al, Org. Lett., 2008, 10, 393 O

H HO

O O

679 Xiamenmycin C Type: 1-Benzopyrans. C17H23NO3 Source: Marine-derived streptomycete Streptomyces xiamenensis (double mutant strain, sediment, East Pacific Ocean). Pharm: Cytotoxic (WI26, cell proliferation inhibitor). Ref: Z. -Y. You, et al, Mar. Drugs, 2013, 11, 4035

2.5 Benzopyranoids

225

OH

O H 2N O

680 Xiamenmycin D Type: 1-Benzopyrans. C22H31NO6 Source: Marine-derived streptomycete Streptomyces xiamenensis (double mutant strain, sediment, East Pacific Ocean). Pharm: Cytotoxic (WI26, cell proliferation inhibitor). Ref: Z. -Y. You, et al, Mar. Drugs, 2013, 11, 4035

OH

O

O

H N

O

O

HO

681 Anhydrofulvic acid Type: Pyrano-1-benzopyrans. C14H10O7 Yellow prisms (DMF aq), mp 237–242 °C. Source: Marine-derived fungus Penicillium afacidum. Pharm: Antifungal; collagenase inhibitor. Ref: K. -I. Fujita, et al, J. Antibiot., 1999, 52, 628 O

OH

O

HO

HO

O O

682 Antibiotic SB236050 Type: Pyrano-1-benzopyrans. C15H14O8 Lignt yellow solid ( > 95% pure). Source: Fungus Chaetomium funicola TCF 6040. Pharm: Metallo-β-lactamase inhibitor (bacterium Bacillus cereus II, Ki = 88 μmol/L; bacterium Bacteroides fragilis CfiA, Ki = 10 μmol/L; bacterium Pseudomonas aeruginosa IMP-1, Ki = 32 μmol/L); metallo-β-lactamase inhibitor (metallo-β-lactamase of Bacillus cereus II, Zn2+ 1 μmol/L, IC50 = 389 μmol/L; Zn2+ 100 μmol/L, IC50 = 256 μmol/L; metallo-β-lactamase of Bacteroides fragilis CfiA, Zn2+ 100 μmol/L, IC50 = 29 μmol/L; metallo-βlactamase of Pseudomonas aeruginosa IMP-1, Zn2+ 100 μmol/L, IC50 = 113 μmol/L;

226

2 Aromatic Metabolites

metallo-β-lactamase of L-1, Zn2+ 100 μmol/L, IC50 > 1000 μmol/L; angiotensinconverting enzyme ACE, Zn2+ 1 μmol/L, IC50 > 1000 μmol/L); synergist of Meropenem antibacterial (Bacteroides fragilis 262 and Bacteroides fragilis 460, meropenem with no synergist, MIC = 16 μg/mL; meropenem with 8 μg/mL synergist, MIC = 2 μg/mL; meropenem with 32 μg/mL synergist, MIC = 0.5 μg/mL; Bacteroides fragilis 288, meropenem with no synergist, MIC = 256 μg/mL; meropenem with 8 μg/ mL synergist, MIC = 32 μg/mL; meropenem with 32 μg/mL synergist, MIC = 8 μg/mL; Stenotrophomonas maltophilia 511, meropenem with no synergist, MIC = 128 μg/mL; meropenem with 32 μg/mL synergist, MIC = 128 μg/mL; Pseudomonas aeruginosa 101, meropenem with no synergist, MIC = 512 μg/mL; meropenem with 32 μg/mL synergist, MIC = 512 μg/mL). Ref: D. J. Payne, et al, Antimicrob. Agents Chemother., 2002, 46, 1880 O

OH

O

HO

HO

O O

O

683 Antibiotic SB238569 Type: Pyrano-1-benzopyrans. C15H12O8 Yellow solid (> 90% pure). Source: Fungus Chaetomium funicola TCF 6040. Pharm: Metallo-β-lactamase inhibitor (bacterium Bacillus cereus II, Ki = 79 μmol/L; bacterium Bacteroides fragilis CfiA, Ki = 3.4 μmol/L; bacterium Pseudomonas aeruginosa IMP-1, Ki = 17 μmol/L); metallo-β-lactamase inhibitor (metallo-β-lactamase of Bacillus cereusII, Zn2+ 1 μmol/L, IC50 = 13 μmol/L, Zn2+ 100 μmol/L, IC50 = 19 μmol/L; metallo-β-lactamase of Bacteroides fragilis CfiA, Zn2+ 100 μmol/L, IC50 = 7 μmol/L; metallo-β-lactamase of Pseudomonas aeruginosa IMP-1, Zn2+ 100 μmol/L, IC50 = 26 μmol/L; metallo-β-lactamase of L-1, Zn2+ 100 μmol/L, IC50 > 1000 μmol/L; angiotensin-converting enzyme ACE, Zn2+ 1 μmol/L, IC50 > 1000 μmol/L); synergist of Meropenem antibacterial (Bacteroides fragilis 262 and Bacteroides fragilis 460, meropenem with no synergist, MIC = 16 μg/mL; meropenem with 8 μg/mL synergist, MIC = 4 μg/mL; meropenem with 32 μg/mL synergist, MIC = 1 μg/mL; Bacteroides fragilis 288, meropenem with no synergist, MIC = 256 μg/mL; meropenem with 8 μg/mL synergist, MIC = 64 μg/mL; meropenem with 32 μg/mL synergist, MIC = 16 μg/mL; Stenotrophomonas maltophilia 511, meropenem with no synergist, MIC = 128 μg/mL; meropenem with 32 μg/mL synergist, MIC = 128 μg/mL; Pseudomonas aeruginosa 101, meropenem with no synergist, MIC = 512 μg/mL; meropenem with 32 μg/mL synergist, MIC = 512 μg/mL). Ref: D. J. Payne, et al, Antimicrob. Agents Chemother., 2002, 46, 1880

2.5 Benzopyranoids

O

OH

O

227

O

HO

O

HO

O

684 Chaetocyclinone A Type: Pyrano-1-benzopyrans. C17H16O8 Yellow solid. Source: Marine-derived fungus Chaetomium sp. Gö 100/2 from an unidentified marine alga. Pharm: Antifungal (inhibits phytopathogenic fungi Phytophthora infestans selectly, 31 ppm, growth InRt = 90%). Ref: S. Lösgen, et al, EurJOC, 2007, 2191 O

O

O

O 4

O

O

O OH

685 Bicoumanigrin Type: Comarinoids. C22H18O8 Amorph. powder. Source: Marine-derived fungus Aspergillus niger from sponge Axinella damicornis. Pharm: Cytotoxic (moderate). Ref: J. Hiort, et al, JNP, 2004, 67, 1532 O

O

O

OH

O HO

O

O

686 Esculetin-4-carboxylic acid ethyl ester Type: Comarinoids. C12H10O6 Amorph. green solid. Source: Sponge Axinella cf. corrugata. Pharm: Antiviral (SARS-Corona virus viral protease 3CL, IC50 = 46 μmol/L); SARS-coronovirus 3CL protease inhibitor. Ref: S. P. de Lira, et al, J. Braz. Chem. Soc., 007,18, 440 O

O

HO

HO

O

O

687 Ascochitin Type: 2-Benzopyrans. C15H16O5 Yellow cryst., mp 196–198 °C, [α]D25 = −86° (CHCl3). Source: Marine-derived fungus Ascochyta salicorniae from green alga Ulva sp. (North Sea coast, Germany), terrestrial fungi (Ascochyta spp.). Pharm: PPs inhibitors

228

2 Aromatic Metabolites

(MPtpB (mycobacterial protein tyrosine phosphatase B), IC50 = 11.5 μmol/L; Cdc25a, IC50 = 69 μmol/L; PTP1B, IC50 = 38.5 μmol/L; VHR, MPtpA and VE-PTP, all inactive); antibacterial (gram-positive and -negative bacteria). Ref: L. Colombo, et al, JCS Perkin I, 1980, 675│S. F. Seibert, et al, Org. Biomol. Chem., 2006, 4, 2233 O

OH O

HO O

688 Asperbiphenyl Type: 2-Benzopyrans. C24H30O6 Amorph. brown powder, [α]D21 = +0.1° (c = 0.26, MeOH). Source: Marine-derived fungus Aspergillus sp. MF-93 (seawater, QuangZhou Gulf, China). Pharm: Antiviral (inhibits multiplication of tobacco mosaic virus (TMV), 0.2mg/mL, InRt = 35.5%). Ref: Z. -J. Wu, et al, Pest Manag. Sci., 2009, 65, 60

HO OH O

O OH OH

689 Aspergilone A Type: 2-Benzopyrans. C26H26O3 Colorless solid. Source: Marine-derived fungus Aspergillus sp. from gorgonian Dichotella gemmacea (South China Sea). Pharm: Cytotoxic (HL60, IC50 = 3.2 μg/mL; MCF7, IC50 = 25.0 μg/mL; A549, IC50 = 37.0 μg/mL); Antifoulant (barnacle Balanus amphitrite, at nontoxic concentration, EC50 = 7.68 μg/mL, settlement inhibitor, potent). Ref: C. -L. Shao, et al, BoMCL, 2011, 21, 690

O

O O

690 7-epi-Austdiol Type: 2-Benzopyrans. C12H12O5 Cryst. (EtOAc/MeOH), mp 174–176 °C, [α]D20 = +116.1° (c = 0.1, MeOH). Source: Mangrove-derived fungus Talaromyces sp. from mangrove

2.5 Benzopyranoids

229

Kandelia candel (stem bark, Qi’ao I., Zhuhai, China). Pharm: Cytotoxic (KB and KBV200, moderate). Ref: F. Liu, et al, Planta Med., 2010, 76, 185 O

H

O O

HO OH

691 Citrinin Monascidin A Type: 2-Benzopyrans. C13H14O5 Lemon-yellow needles (EtOH or MeOH), mp 178–179 °C, [α]D18 = −37.4° (EtOH). Source: Marine-derived fungus Microsporum sp. from red alga Lomentaria catenata (Korea, surface). Pharm: Antioxidant (DPPH scavenger, moderate); phytotoxic; cytotoxin; severe skin irritant; LD50 (mus, orl) = 112 mg/kg. Ref: Y. Li, et al, CPB, 2006, 54, 882 OH

O HO

O O

692 Cytosporone C 1-Heptyl-1,4-dihydro-6,8-dihydroxy-3H-2-benzopyran-3-one Type: 2-Benzopyrans. C16H22O4 Cryst. (Me2CO), [α]D20 = +11° (c = 0.1, MeOH). Source: Mangrove-derived fungus Leucostoma persoonii from mangrove Rhizophora mangle (branch, Everglades, Florida). Pharm: Antibacterial (MRSA, MIC > 358 μmol/L; A549 IC50 = 690 μmol/L, IC90 = 840 μmol/L). Ref: S. F. Brady, et al, Org. Lett., 2000, 2, 4043│M. P. Singh, et al, Mar. Drugs, 2007, 5, 71│J. Xu, et al, BoMC, 2009, 17, 7362│J. Beau, et al, Mar. Drugs, 2012, 10, 762 HO

O 7

O OH

693 6-Desmethoxyhormothamnione Type: 2-Benzopyrans. C20H18O7 Light yellow solid. Source: Brown alga Chrysophaeum taylorii. Pharm: Cytotoxic (9KB, ID50 = 1 μg/mL). Ref: W. H. Gerwick, et al, Tet. Lett., 1986, 27, 1979│W. H. Gerwick, JNP, 1989, 52, 252

230

2 Aromatic Metabolites

OH

O

6

O

OH

O O OH

694 Dothiorelone D Type: 2-Benzopyrans. C15H20O5 Source: Mangrove-derived fungus Dothiorella sp. Pharm: Cytotoxic. Ref: Q. Yu, et al, CA, 2004, 142, 388784y

HO

O O

OH

OH

695 Hormothamnione Type: 2-Benzopyrans. C21H20O8 Yellow solid, mp 270 °C (dec). Source: Brown algae Chrysophaeum taylorii and Hormothamnion enteromorphoides (Puerto Rico). Pharm: Cytotoxic; RNA synthesis inhibitor. Ref: W. H. Gerwick, et al, Tet. Lett., 1986, 27, 1979│W. H. Gerwick, JNP, 1989, 52, 252

OH O

O

6

O

OH

O O OH

696 Isochromophilone XI Type: 2-Benzopyrans. C25H29ClO8 Source: Sponge Tethya aurantium, marine fungus Bartalinia robillardoides strain LF550. Pharm: Antibacterial (Bacillus subtilis, MIC = 55.6 μmol/L, Staphylococcus lentus, MIC = 78.4 μmol/L); antifungal (Trichophyton rubrum, MIC = 41.5 μmol/L). Ref: J. Wiese, et al, Mar. Drugs, 2011, 9, 561│N. Jansen, et al, Mar. Drugs, 2013, 11, 800

2.5 Benzopyranoids

231

Cl O O

O

OH

O

O

O

OH

697 8-O-Methyl-epi-austdiol Type: 2-Benzopyrans. C13H14O5 Yellow powder, mp 160–161 °C, [α]D20 = +115.5° (c = 0.1, MeOH). Source: Mangrove-derived fungus Talaromyces sp. ZH-154 from mangrove Kandelia candel (stem bark, Qi’ao I., Zhuhai, China). Pharm: Cytotoxic (KB and KBV200, moderate). Ref: F. Liu, et al, Planta Med., 2010, 76, 185 O

H

O O

HO O

698 Peneciraistin A Type: 2-Benzopyrans. C15H20O5 Source: Marine-derived fungus Penicillium raistrickii (saline soil, Bohai Bay, Shandong, China). Pharm: Antioxidant (DPPH scavenger). Ref: L. -Y. Ma, et al, Tetrahedron, 2012, 68, 2276 HO HO

1R

O

O

OH

699 Peneciraistin B Type: 2-Benzopyrans. C15H20O5 Source: Marine-derived fungus Penicillium raistrickii (saline soil, Bohai Bay, Shandong, China). Pharm: Antioxidant (DPPH scavenger). Ref: L. -Y. Ma, et al, Tetrahedron, 2012, 68, 2276 HO HO

1S

O OH

O

232

2 Aromatic Metabolites

700 Peneciraistin C Type: 2-Benzopyrans. C19H26O9 Source: Marine-derived fungus Penicillium raistrickii (saline soil, Bohai Bay, Shandong, China). Pharm: Cytotoxic (A549 and MCF7, moderate). Ref: L. -Y. Ma, et al, Tetrahedron, 2012, 68, 2276 O

O O

O

HO O

HO

O

O

701 Peneciraistin D Type: 2-Benzopyrans. C15H16O6 Source: Marine-derived fungus Penicillium raistrickii (saline soil, Bohai Bay, Shandong, China). Pharm: Antioxidant (DPPH scavenger). Ref: L. -Y. Ma, et al, Tetrahedron, 2012, 68, 2276 HO O OH

O

OH

O

702 Penicillanthranin A Type: 2-Benzopyrans. C28H24O10 Source: Marine-derived fungus Penicillium citrinum from gorgonian sea fan Annella sp. (Similan Is., Phangnga, Thailand). Pharm: Antibacterial (Staphylococcus aureus and MRSA). Ref: N. Khamthong, et al, Tetrahedron, 2012, 68, 8245 OH COOH

OH OH

O

OH

O

HO O

703 Penicitrinol C Type: 2-Benzopyrans. C14H18O4 Source: Marine-derived fungus Penicillium citrinum (sediment, Lanqi I., Fujian, China). Pharm: Cytotoxic (HL60, weak). Ref: L. Chen, et al, CPB, 2011, 59, 515

2.5 Benzopyranoids

233

OH

HO O O

704 Pestalachloride C Type: 2-Benzopyrans. C21H20Cl2O5 Source: Marine-derived fungus Pestalotiopsis sp. ZJ-2009-7-6 from a soft coral. Pharm: Antibacterial (Enterobacter coli, MIC = 5.0 μmol/L, Vibrio anguillarum, MIC = 10.0 μmol/L, Vibrio parahaemolyticus, MIC = 20.0 μmol/L). Ref: M. Y. Wei, et al, Mar. Drugs, 2013, 11, 1050 Cl

O

H

O

OH

H Cl O

OH H

705 Pestalachloride D Type: 2-Benzopyrans. C21H20Cl2O5 Source: Marine-derived fungus Pestalotiopsis sp. ZJ-2009-7-6 from a soft coral. Pharm: Antibacterial (Enterobacter coli, MIC = 5.0 μmol/L, Vibrio anguillarum, MIC = 10.0 μmol/L, Vibrio parahaemolyticus, MIC = 20.0 μmol/L). Ref: M. Y. Wei, et al, Mar. Drugs, 2013, 11, 1050 Cl

O O

H

OH

H Cl O

OH H

706 Pinophilin A Type: 2-Benzopyrans. C21H22O7 Source: Marine-derived fungus Penicillium pinophilum from green alga Ulva fasciata (Kasai, Tokyo, Japan). Pharm: Mammalian DNA polymerases inhibitor (A (pol γ), B (pols α, δ, and ε), and Y (pols η, ι, and κ) families, selective); cytotoxic (HTCLs cells, growth and proliferation inhibitor). Ref: Y. Myobatake, et al, JNP, 2012, 75, 135

234

2 Aromatic Metabolites

OH

HO O

O

OH

H O

O

707 Pinophilin B Type: 2-Benzopyrans. C21H22O8 Source: Marine-derived fungus Penicillium pinophilum from green alga Ulva fasciata (Kasai, Tokyo, Japan). Pharm: Mammalian DNA polymerases inhibitor (A (pol γ), B (pols α, δ, and ε), and Y (pols η, ι, and κ) families, selective); cytotoxic (HTCLs cells, growth and proliferation inhibitor). Ref: Y. Myobatake, et al, JNP, 2012, 75, 135 OH

HO O

O OH

H O OH

O

708 (3R,4S)-3,4,5-Trimethyisochroman-6,8-diol Type: 2-Benzopyrans. C12H16O3 Source: Deep-sea fungus Aspergillus sydowi YH11-2 (Guam, depth of 1000 m, E144°43′ N13°26′). Pharm: Cytotoxic (P388, IC50 = 1.95 μmol/L, control CDDP, IC50 = 0.039 μmol/L). Ref: L. Tian, et al, Arch. Pharm. Res,. 2007, 30, 1051

HO O OH

709 Chaetomugilin A Type: Azaphilone 2-benzopyrans. C23H27ClO7 Yellow powder (CHCl3/MeOH), mp 149–151 °C, [α]D = −50.1° (c = 0.16, EtOH). Source: Marine-derived fungus Chaetomium globosum OUPS-T106B-6 from fish Mugil cephalus (Katsuura Bay, Japan), terrestrial fungus (Chaetomium globosum). Pharm: Cytotoxic (P388, IC50 = 8.7 μmol/L, control 5-FU, IC50 = 1.7 μmol/L; HL60, IC50 = 7.3 μmol/L, 5-FU, IC50 = 2.7 μmol/L);

2.5 Benzopyranoids

235

cytotoxic (panel of 39 hmn cancer cell lines: HBC4, Log10 GI50 (mol/L) = −4.00; BSY1, Log10 GI50 (mol/L) = −4.00; HBC5, Log10 GI50 (mol/L) = −4.00; MCF7, Log10 GI50 (mol/L) = −4.43; MDA-MB-231, Log10 GI50 (mol/L) = −4.00; U251, Log10 GI50 (mol/L) = −4.00; SF268, Log10 GI50 (mol/L) = −4.00; SF295, Log10 GI50 (mol/L) = −4.00; SF539, Log10 GI50 (mol/L) = −4.00; SNB75, Log10 GI50 (mol/L) = −4.36; SNB78, Log10 GI50 (mol/L) = −4.00; HCC2998, Log10 GI50 (mol/L) = −4.00; KM12, Log10 GI50 (mol/L) = −4.00; HT29, Log10 GI50 (mol/L) = −4.00; HCT15, Log10 GI50 (mol/L) = −4.00; HCT116, Log10 GI50 (mol/L) = −4.00; NCI-H23, Log10 GI50 (mol/L) = −4.00; NCIH226, Log10 GI50 (mol/L) = −4.18; NCI-H522, Log10 GI50 (mol/L) = −4.36; NCI-H460, Log10 GI50 (mol/L) = −4.00; A549, Log10 GI50 (mol/L) = −4.00; DMS273, Log10 GI50 (mol/L) = −4.00; DMS114, Log10 GI50 (mol/L) = −4.06; LOX-IMVI, Log10 GI50 (mol/L) = −4.15; OVCAR-3, Log10 GI50 (mol/L) = −4.00; OVCAR-4, Log10 GI50 (mol/L) = −4.00; OVCAR-5, Log10 GI50 (mol/L) = −4.00; OVCAR-8, Log10 GI50 (mol/L) = −4.00; SK-OV-3, Log10 GI50 (mol/L) = −4.00; RXF-631L, Log10 GI50 (mol/L) = −4.63; ACHN, Log10 GI50 (mol/L) = −5.51; St4, Log10 GI50 (mol/L) = −4.00; MKN1, Log10 GI50 (mol/L) = −4.00; MKN7, Log10 GI50 (mol/L) = −4.00; MKN28, Log10 GI50 (mol/L) = −4.73; MKN45, Log10 GI50 (mol/L) = −4.51; MKN74, Log10 GI50 (mol/L) = −5.24; DU145, Log10 GI50 (mol/L) = −4.00; PC3, Log10 GI50 (mol/L) = −4.00; MG-MID (mean value of Log10 GI50 (mol/L) for all cell lines tested) = −4.10; Δ (difference in Log10 GI50 (mol/L) value of most sensitive cell and MG-MID value) = 1.13; Range (difference in Log10 GI50 (mol/L) value of most sensitive cell and least sensitive cell) = 1.24 (effective value of selective cytotoxic activity: MG-MID 100 μmol/L, 5-FU, IC50 = 1.1 μmol/L; KB, IC50 > 100 μmol/L, 5-FU, IC50 = 7.7 μmol/L). Ref: Y. Muroga, et al, Helv. Chim. Acta, 2010, 93, 542 Cl 12

O 11

OH

O H H

O

2'

O

OH

3'

O

4'

712 Chaetomugilin B Type: Azaphilone 2-benzopyrans. C24H29ClO7 Yellow prisms (CHCl3/MeOH), mp 215–217 °C, [α]D = −40.2° (c = 0.03, EtOH). Source: Marine-derived fungus Chaetomium globosum OUPS-T106B-6 from fish Mugil cephalus (Katsuura Bay, Japan). Pharm: Cytotoxic (P388, IC50 = 18.7 μmol/L, control 5-FU, IC50 = 1.7 μmol/L; HL60, IC50 = 16.5 μmol/L, 5-FU, IC50 = 2.7 μmol/L); cytotoxic selective (panel of 39 hmn cancer cell lines: HBC4, Log10 GI50 (mol/L) = −4.22; BSY1, Log10 GI50 (mol/L) = −4.64; HBC5, Log10 GI50 (mol/L) = −4.56; MCF7, Log10 GI50 (mol/L) = −4.16; MDA-MB-231, Log10 GI50 (mol/L) = −4.51; U251, Log10 GI50 (mol/L) = −4.00; SF268, Log10 GI50 (mol/L) = −4.05; SF295, Log10 GI50 (mol/L) = −4.00; SF539, Log10 GI50 (mol/L) = −4.25; SNB75, Log10 GI50 (mol/L) = −4.21; SNB78, Log10 GI50 (mol/L) = −4.15; HCC2998, Log10 GI50 (mol/L) = −4.00; KM12, Log10 GI50 (mol/L) = −4.08; HT29, Log10 GI50 (mol/L) = −4.01; HCT15, Log10 GI50 (mol/L) = −4.14; HCT116, Log10 GI50 (mol/L) = −4.31; NCI-H23, Log10 GI50 (mol/L) = −4.00; NCI-H226, Log10 GI50 (mol/L) = −4.00; NCI-H522, Log10 GI50 (mol/L) = −4.81; NCI-H460, Log10 GI50 (mol/L) = −4.00; A549, Log10 GI50 (mol/L) = −4.00; DMS273, Log10 GI50 (mol/L) = −4.00;

2.5 Benzopyranoids

237

DMS114, Log10 GI50 (mol/L) = −4.11; LOX-IMVI, Log10 GI50 (mol/L) = −4.24; OVCAR-3, Log10 GI50 (mol/L) = −4.61; OVCAR-4, Log10 GI50 (mol/L) = −4.18; OVCAR-5, Log10 GI50 (mol/L) = −4.13; OVCAR-8, Log10 GI50 (mol/L) = −4.00; SKOV-3, Log10 GI50 (mol/L) = −4.00; RXF-631L, Log10 GI50 (mol/L) = −4.00; ACHN, Log10 GI50 (mol/L) = −4.19; St4, Log10 GI50 (mol/L) = −4.00; MKN1, Log10 GI50 (mol/L) = −4.52; MKN7, Log10 GI50 (mol/L) = −4.35; MKN28, Log10 GI50 (mol/L) = −4.22; MKN45, Log10 GI50 (mol/L) = −4.00; MKN74, Log10 GI50 (mol/L) = −4.34; DU145, Log10 GI50 (mol/L) = −4.00; PC3, Log10 GI50 (mol/L) = −4.41; MG-MID (mean value of Log10 GI50 (mol/L) for all cell lines tested) = −4.19; Δ (difference in Log10 GI50 (mol/L) value of most sensitive cell and MG-MID value) = 0.62; Range (difference in Log10 GI50 (mol/L) value of most sensitive cell and least sensitive cell) = 0.81 (effective value of selective cytotoxic activity: MG-MID 280 °C, [α]D27 = +490° (c = 0.2, MeOH). Source: Mangrove-derived fungus Penicillium sp. JP-1 from mangrove Aegiceras corniculatum (China waters), mangrove-derived fungus Talaromyces bacillisporus SBE-14. Pharm: Mycotoxin; antibacterial. Ref: M. Yamazaki, et al, CPB, 1980, 28, 3649│T. Dethoup, et al, PM, 2006, 72, 957│Z. Guo, et al, Magn. Reson. Chem., 2007, 45, 439│Z. J. Lin, et al, Phytochemistry, 2008, 69, 1273 OH

O OH

O

O O

OH

O

O OH

825 Bacillosporin D‡ Type: Duclauxin group. C26H16O11 Pale yellow cryst., mp > 280 °C, [α]D27 = +700° (c = 0.2, MeOH). Source: Mangrove-derived fungus Talaromyces bacillisporus SBE-14. Pharm: Mycotoxin; antibacterial. Ref: M. Yamazaki, et al, CPB, 1980, 28, 3649│T. Dethoup, et al, PM, 2006, 72, 957│Z. Guo, et al, Magn. Reson. Chem., 2007, 45, 439 O

OH

O 11

O HO O O

O OH 16

O HO

826 Annulin A Type: Naphthoquinone derivatives. C19H20O7 Orange cryst. (EtOH), mp 174–176 °C. Source: Hydroid Garveia annulata (order Anthoathecata, Northeastern Pacific). Pharm: Inhibits indoleamine 2,3-dioxygenase (IDO) (in vitro, Ki = 0.12–0.69 μmol/L); antibacterial. Ref: E. Fahy, et al, JOC, 1986, 51, 5145│A. Pereira, et al, JNP, 2006, 69, 1496

2.9 Naphthalene Derivatives

281

O

1

O O

OH

O

OH

O

827 Annulin B Type: Naphthoquinone derivatives. C21H22O7 Orange oil, [α]D = +8° (c = 0.2, CHCl3). Source: Hydroid Garveia annulata (order Anthoathecata, Northeastern Pacific). Pharm: Inhibits indoleamine 2,3-dioxygenase (IDO) (in vitro, Ki = 0.12–0.69 μmol/L). Ref: E. Fahy, et al, JOC, 1986, 51, 5145│A. Pereira, et al, JNP, 2006, 69, 1496 O O O O OH

O

O

828 Annulin C Type: Naphthoquinone derivatives. C20H22O7 Yellow oil. Source: Hydroid Garveia annulata (order Anthoathecata, Northeastern Pacific). Pharm: Inhibits indoleamine 2,3-dioxygenase (IDO) (in vitro, Ki = 0.12–0.69 μmol/L). Ref: A. Pereira, et al, JNP, 2006, 69, 1496 O

1

O O

OH

O

O

829 Debromomarinone Type: Naphthoquinone derivatives. C25H28O5 Source: An unidentified marinederived actinomycete CNB-632 (shallow water sediment). Pharm: Antibacterial (in vitro, gram-positive bacteria MIC = 1–2 μg/mL; Staphylococcus aureus, Staphylococcus epidermis, Staphylococcus pneumoniae and Staphylococcus pyrogenes). Ref: Pathirana, et al, Tet. Lett., 1992, 33, 7663│J. A. Kalaitzis, et al, Org. Lett., 2003, 5, 4449 (structure revised)

282

2 Aromatic Metabolites

OH

O O H

H

HO O

830 Debromomethoxymarinone Methoxydebromomarinone Type: Naphthoquinone derivatives. C26H30O6 [α]D25 = +140° (c = 0.1, EtOH). Source: An unidentified marine-derived actinomycete CNH-099 (Batiquitos Lagoon, North of San Diego, CA). Pharm: Cytotoxic (colon carcinoma HCT116 cell lines, IC50 ≈ 8 μg/mL). Ref: I. H. Hardt,et al, Tet. Lett., 2000, 41, 2073

OH

O O H

HO O

13

O

831 Deoxylapachol 2-Prenyl-1,4-naphthoquinone Type: Naphthoquinone derivatives. C15H14O2 Brightyellow prisms (petrol), mp 60–61 °C. Source: Brown alga Landsburgia quercifolia. Pharm: Cytotoxic; skin irritant. Ref: N. B. Perry, et al, JNP, 1991, 54, 978

O

O

832 Fusarnaphthoquinone A Type: Naphthoquinone derivatives. C15H18O7 Source: Marine-derived fungi Fusarium sp. from gorgonian sea fan Annella sp. (Koh Hin Ran Pet, Surat Thani Province, Thailand). Pharm: Cytotoxic (KB, IC50 = 130 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 22 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, inactive, control Ellipticine, IC50 = 4.47 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507

2.9 Naphthalene Derivatives

OH

283

OH

O O OH

O

OH

833 Fusarnaphthoquinone B Type: Naphthoquinone derivatives. C15H16O5 Source: Marine-derived fungi Fusarium sp. from gorgonian sea fan Annella sp. (Koh Hin Ran Pet, Surat Thani Province, Thailand). Pharm: Antifungal (Cryptococcus neoformans and Microsporum gypseum, MIC = 200 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507 OH

O

O

O

OH

834 Griseusin C Type: Naphthoquinone derivatives. C20H16O9 Orange powder. Source: Mangrovederived fungus Penicillium sp. GT200261505 from mangrove Kandelia candel (China waters). Pharm: 3α-Hydroxysteroid dehydrogenase inhibitor (mild). Ref: X. Li, et al, Arch. Pharmacal Res., 2006, 29, 942 O OH

O

O O

O

H

OH H

O O

835 Hydroxydebromomarinone Type: Naphthoquinone derivatives. C25H28O6 [α]D25 = +280° (c = 0.2, EtOH). Source: An unidentified marine-derived actinomycete CNH-099 (Batiquitos Lagoon, North of San Diego, CA). Pharm: Cytotoxic (colon carcinoma HCT116 cell lines, IC50 ≈ 8 μg/mL). Ref: I. H. Hardt, et al, Tet. Lett., 2000, 41, 2073 OH

O O H

HO O

13

OH

284

2 Aromatic Metabolites

836 Isomarinone Type: Naphthoquinone derivatives. C25H27BrO5 [α]D25 = −120° (c = 0.2, MeOH). Source: An unidentified marine-derived actinomycete CNH-099 (Batiquitos Lagoon, North of San Diego, CA). Pharm: Cytotoxic (colon carcinoma HCT116 cell lines, IC50 ≈ 8 μg/mL). Ref: I. H. Hardt, et al, Tet. Lett., 2000, 41, 2073 OH

O

Br

O 5

H

HO H

O

837 Javanicin tautomeric with 5,8-quinone structure Type: Naphthoquinone derivatives. C15H14O6 Source: Marine-derived fungus Fusarium sp. PSU-F135 Pharm: Antiplasmodial (in vitro Plasmodium falciparum K1, IC50 = 12 μmol/L, control Dihydroartemisinin, IC50 = 0.004 μmol/L); cytotoxic (KB, IC50 = 5.7 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 13 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, IC50 = 170 μmol/L, control Ellipticine, IC50 = 4.47 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507 O

OH

O 8

O

5

O

OH

838 Marinone Type: Naphthoquinone derivatives. C25H27BrO5 [α]D25 = −170° (c = 0.15, MeOH). Source: An unidentified marine-derived actinomycete CNB-632 (shallow water sediment), an unidentified marine-derived actinomycete CNH-099 (Batiquitos Lagoon, North of San Diego, CA). Pharm: Antibacterial (in vitro, gram-positive bacteria MIC = 1.0 μg/mL; Bacillus subtilis). Ref: C. Pathirana, et al, Tet. Lett., 1992, 33, 7663│I. H. Hardt, et al, Tet. Lett., 2000, 41, 2073 OH

O O H

HO H Br

O

2.9 Naphthalene Derivatives

285

839 Neomarinone Type: Naphthoquinone derivatives. C26H32O5 [α]D25 = +86° (c = 0.5, MeOH). Source: An unidentified marine-derived actinomycete CNH-099 (Batiquitos Lagoon, North of San Diego, CA). Pharm: Cytotoxic (colon carcinoma HCT116 cell lines, IC50 ≈ 8 μg/mL); cytotoxic (NCI’s 60 cancer cell line panel, mean IC50 = 10 μg/mL). Ref: I. H. Hardt, et al, Tet. Lett., 2000, 41, 2073│J. A. Kalaitzis, et al, Org. Lett., 2003, 5, 4449│M. Peña-López, et al, Chem. Eur. J., 2009, 15, 910

O

O

HO

OH O

840 Seriniquinone Type: Naphthoquinone derivatives. C20H8O4S Source: Marine bacterium Serinicoccus sp. Pharm: Cytotoxic (selective). Ref: L. Trzoss, et al, Proc. Natl. Acad. Sci. USA, 2014, 111, 14687

O

O

O

S O

841 Antibiotic A 80915A Type: Benzochromanquinones. C26H31Cl3O5 Pale yellow powder, [α]D25 = −89.7° (c = 1, MeOH). Source: An unidentified marine-derived actinomycete CNQ-525. Pharm: Antibacterial (including MRSA); cytotoxic. Ref: D. S. Fukuda, et al, J. Antibiot., 1990, 43, 623│I. E. Soria-Mercado, et al, JNP, 2005, 68, 904│N. M. Haste, et al, Mar. Drugs, 2011, 9, 680 OH

O

Cl

4a

HO

Cl 4

O O

Cl

286

2 Aromatic Metabolites

842 Antibiotic A 80915C Type: Benzochromanquinones. C26H33Cl3O6 Yellow prisms, [α]D25 = −190° (c = 0.03, CHCl3), [α]D25 = −115.4° (c = 0.56, MeOH). Source: An unidentified marine-derived actinomycete CNQ-525. Pharm: Antibacterial; cytotoxic. Ref: D. S. Fukuda, et al, J. Antibiot., 1990, 43, 623│Soria-Mercado, et al, JNP, 2005, 68, 904 OH

O

Cl

Cl 4

4a

HO

O

OH

O

Cl

843 4a-Dechloroantibiotic A 80915C Type: Benzochromanquinones. C26H34Cl2O6 Pale yellow cryst., mp 197–198 °C, [α]D25 = −24.3° (c = 0.14, MeOH). Source: An unidentified marine-derived actinomycete CNQ-525. Pharm: Cytotoxic. Ref: I. E. Soria-Mercado, et al, JNP, 2005, 68, 904 OH

O

H

4a

HO

Cl 4

O

OH

O

Cl

844 4a-Dechloro-4,4a-didehydro-antibiotic A 80915A Type: Benzochromanquinones. C26H30Cl2O5 Pale yellow cryst., mp 179–181 °C, [α]D25 = −7.7° (c = 0.4, MeOH). Source: An unidentified marine-derived actinomycete CNQ-525. Pharm: Cytotoxic. Ref: N. M. Haste, et al, Mar. Drugs, 2011, 9, 680 OH

O Cl 4a

HO

4

O O

Cl

2.9 Naphthalene Derivatives

287

845 Napyradiomycin A Type: Benzochromanquinones. C25H27ClO6 Source: Marine-derived streptomycete Streptomyces sp. CNQ-329 (sediment, San Diego, California, USA). Pharm: Cytotoxic (HCT116, moderate); antibacterial (MRSA, moderate). Ref: J. W. Blunt, et al, NPR, 2015, 32, 116 (rev)

O

OH

Cl OH

O

OH

O

846 Napyradiomycin B Type: Benzochromanquinones. C25H28O7 Source: Marine-derived streptomycete Streptomyces sp. CNQ-329 (sediment, San Diego, California, USA). Pharm: Antibacterial (MRSA, moderate). Ref: J. W. Blunt, et al, NPR, 2015, 32, 116 (rev)

O

OH

HO OH

O

OH

O

847 Napyradiomycin D Type: Benzochromanquinones. C25H26Cl2O5 Source: Marine-derived streptomycete Streptomyces sp. CNQ-329 (sediment, San Diego, California, USA). Pharm: Cytotoxic (HCT116, moderate). Ref: J. W. Blunt, et al, NPR, 2015, 32, 116 (rev)

O

Cl

OH

Cl O

O O

288

2 Aromatic Metabolites

848 Napyradiomycin E Type: Benzochromanquinones. C25H28BrClO5 Source: Marine-derived streptomycete Streptomyces sp. CNQ-329 (sediment, San Diego, California, USA). Pharm: Cytotoxic (HCT116, moderate). Ref: J. W. Blunt, et al, NPR, 2015, 32, 116 (rev) O

OH

Cl

O H

OH O

Br

849 Napyradiomycin F Type: Benzochromanquinones. C25H32Cl2O6 Source: Marine-derived streptomycete Streptomyces sp. CNH-070 (sediment, San Elijo Lagoon, Encinitas, California, USA). Pharm: Cytotoxic (HCT116, moderate). Ref: J. W. Blunt, et al, NPR, 2015, 32, 116 (rev)

H

Cl

O H

Cl

O

OH

OH O OH

850 Anhydroexfoliamycin Type: Benzoisochromanquinones. C22H24O8 Dark red solid, mp 167 °C, [α]D20 = +633° (c = 0.14, MeOH). Source: Marine-derived streptomycete Streptomyces exfoliatus from marine soil. Pharm: Antibacterial (gram-positive bacteria); anti-AD preclinical trial (Target: GSK3β mediated by the JNK pathway. Animal Model: 3xTg-AD mice. Effect: GSK3β inhibition τ, phosphorylation reduction) (Russo, 2016). Ref: O. Potterat, et al, J. Antibiot., 1993, 46, 346│C. Volkmann, et al, J. Antibiot., 1995, 48, 431│P. Russo, et al, Mar. Drugs, 2016, 14, 5 (review) OH

HO OH

O O

O

O

OH

2.9 Naphthalene Derivatives

289

851 Anhydrofusarubin Type: Benzoisochromanquinones. C15H12O6 Violet-black needles (MeOH), mp 193–201 °C. Source: Marine-derived fungi Fusarium sp. from gorgonian sea fan Annella sp. (Koh Hin Ran Pet, Surat Thani Province, Thailand), marine-derived fungus Fusarium sp. PSU-F135. Pharm: Antiplasmodial (in vitro Plasmodium falciparum K1, IC50 = 14 μmol/L, control Dihydroartemisinin, IC50 = 0.004 μmol/L); antituberculosis (Mycobacterium tuberculosis, MIC = 87 μmol/L, control Isoniazid, MIC = 0.17–0.34 μmol/L); cytotoxic (KB, IC50 = 2.0 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 0.9 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, IC50 = 58 μmol/L, control Ellipticine, IC50 = 4.47 μmol/L); antibacterial (Staphylococcus aureus and MRSA, MIC = 350 μmol/L). Ref: B. E. Cross, et al, JCS(C), 1970, 930│N. Claydon, et al, J. Invertebr. Pathol., 1977, 30, 216│K. Trisuwan, et al, JNP, 2010, 73, 1507 OH

O

O 6

4a 10a

9

O

1

OH

O

852 Fusarubin Oxyjavanicin; Hydroxyjavanicin Type: Benzoisochromanquinones. C15H14O7 Red prisms (C6H6), mp 218 °C. Source: Marine-derived fungi Fusarium sp. PSU-F135. Pharm: Cytotoxic (KB, IC50 = 14 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 9.8 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, IC50 = 79 μmol/L, control Ellipticine, IC50 = 4.47 μmol/L); antibacterial (Staphylococcus aureus and MRSA, MIC = 350 μmol/L); antifungal (Cryptococcus neoformans and Microsporum gypseum, MIC = 200 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507 O

OH

O

OH O O

OH

853 Halawanone A Type: Benzoisochromanquinones. C23H22O9 Source: Marine-derived streptomycete Streptomyces sp. BD-18T (shallow water sediment on Oahu). Pharm: Antibacterial (Bacillus subtilis, Staphylococcus aureus, gram-positive bacteria). Ref: P. W. Ford, et al, JNP, 1998, 61, 1232

290

O

2 Aromatic Metabolites

O

O

OH O

HO H

O

O

O

854 Halawanone B Type: Benzoisochromanquinones. C22H20O9 Source: Marine-derived streptomycete Streptomyces sp. BD-18T (shallow water sediment on Oahu). Pharm: Antibacterial (Bacillus subtilis, Staphylococcus aureus, gram-positive bacteria). Ref: P. W. Ford, et al, JNP, 1998, 61, 1232

O

O

O

OH

HO

O H

O

O

855 3-O-Methylfusarubin Type: Benzoisochromanquinones. C16H16O7 Reddish–orange needles (CHCl3/EtOH), mp 157–158 °C, mp 188–189 °C. Source: Marine-derived fungi Fusarium sp. PSUF135. Pharm: Antibacterial (gram-positive bacteria), antifungal; cytotoxic (mouse leukaemia). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507 O

OH

O

O O O

OH

856 Obionin A Type: Benzoisochromanquinones. C21H24O5 Brown-red solid, mp 168–169 °C, [α]D = +28.5° (c = 0.01, CHCl3). Source: Marine-derived fungus Leptosphaeria obiones. Pharm: Inhibits binding of dopamine D-1 selective ligand to bovine corpus striatum membrane (IC50 = 2.5 μg/mL). Ref: G. K. Poch, et al, Tet. Lett., 1989, 30, 3483│T. S. Bugni, et al, NPR, 2004, 21, 143 (rev)

2.9 Naphthalene Derivatives

291

O 1' 1

O O

O

OH

857 Obioninene Leptosphaerodione Type: Benzoisochromanquinones. C21H22O5 Deep red solid, [α]D20 = −53.3° (c = 0.02, MeOH). Source: Marine-derived fungus Leptosphaeria oraemaris, Stagonospora spp. Pharm: Phytotoxin. Ref: A. Guerriero, et al, Helv. Chim. Acta, 1991, 74, 1445

O 1' 1

O O

O

OH

858 5-Bromo-4,7-dihydroxy-1-indanone Type: Indenes and indanes. C9H7BrO3 Source: An unidentified sponge. Pharm: Antineoplastic. Ref: Japan. Pat., 1996, 96 198 798; CA, 125, 217489a OH

O

Br OH

859 2,3-Dihydro-1-methoxy-6-methyl-3-oxo-1H-indene-4-carboxaldehyde 7-Formyl-3-methoxy-5-methyl-1-indanone Type: Indenes and indanes. C12H12O3 Clear oil, [α]D = +1.3° (c = 1.1, MeOH). Source: Cyanobacterium Lyngbya majuscula (Guam). Pharm: Inhibits hypoxia-induced activation of VEGF gene promotor (Hep3B). Ref: D. G. Nagle, et al, JNP, 2000, 63, 1431 O O

O

860 Penostatin E Type: Indenes and indanes. C22H32O3 Oil, [α]D = +48.5° (c = 0.16, CHCl3). Source: Marine-derived fungus Penicillium sp. OUPS-79 from green alga Enteromorpha

292

2 Aromatic Metabolites

intestinalis. Pharm: Cytotoxic (P388, ED50 = 0.9 μg/mL). Ref: C. Takahashi, et al, Tet. Lett., 1996, 37, 655│C. Iwamoto, et al, Tetrahedron, 1999, 55, 14353

OH

HO

H

O

2.10 Anthracene Derivatives 861 Abietinarin A Type: Anthracenes. C19H22O4 Yellow amorph. solid. Source: Hydroid Abietinaria sp. Pharm: Cytotoxic (L1210, ED50 < 10 μg/mL). Ref: C.Pathirana, et al, Can. J. Chem., 1990, 68, 394 OH

O

HO

O

862 Abietinarin B Type: Anthracenes. C19H22O4 Yellow amorph. solid. Source: Hydroid Abietinaria sp. Pharm: Cytotoxic. Ref: C. Pathirana, et al, Can. J. Chem., 1990, 68, 394 OH

O

HO

O

863 Anthracene derivative 100 Type: Anthracenes. C20H18O3 Source: Marine-derived streptomycete Streptomyces sp. (sediment, Kiaochow Bay, Qingdao, China). Pharm: Cytotoxic (A549 cell line). Ref: H. Zhang, et al, Mar. Drugs, 2011, 9, 1502 O OH

O

2.10 Anthracene Derivatives

293

864 Asperflavin 6-O-α-D-Ribofuranoside Type: Anthracenes. C21H24O9 Yellow oil, [α]D20 = +23.8° (c = 0.2, MeOH). Source: Marine-derived fungus Microsporum sp. from red alga Lomentaria catenata (surface, Korea waters). Pharm: Antioxidant (DPPH scavenger, IC50 = 14.2 μmol/L, control Ascorbic acid, IC50 = 20 μmol/L); antibacterial (MRSA and MDRSA, MIC = 50 μg/mL). Ref: Y. Li, et al, CPB, 2006, 54, 882 O

OH

O

O

OH

O HO

OH OH

865 Eurorubrin 5,5ʹ-Methylenebisasperflavin Type: Anthracenes. C33H32O10 Amorph. brown powder, [α]D25 = +21.1° (c = 0.3, MeOH). Source: Mangrove-derived fungus Eurotium rubrum, from semimangrove Hibiscus tiliaceus (stem, Hainan, I., China). Pharm: Antioxidant (DPPH scavenger, strong exceeding control BHT). Ref: D. -L. Li, et al, J. Microbiol. Biotechnol., 2009, 19, 675 O

OH

O

OH HO CH2 HO OH

O

OH

O

866 Fusaquinone B Tetrahydrobostrycin Type: Anthracenes. C16H20O8 Needles, [α]D20 = −93.2° (c = 0.07, DMSO) (Fusarium sp.), [α]D18 = −116.6° (c = 0.8, MeOH) (Aspergillus sp.). Source: Mangrove-derived fungus Fusarium sp. ZH-210 from an unidentified mangrove (sediment), marine-derived fungus Aspergillus sp. 05F16. Pharm: Antibacterial (100 μg/disc, Staphylococcus aureus, IZD = 15 mm; Escherichia coli, IZD = 9.2 mm). Ref: J. Xu, et al, J. Antibiot., 2009, 61, 415 (Aspergillus)│Y. Chen, et al, Magn. Reson. Chem., 2009, 47, 362│K. Trisuwan, et al, JNP, 2010, 73, 1507

294

2 Aromatic Metabolites

OH

O

H

OH OH OH

O OH

OH

H

867 Fusaquinone C 1-Deoxytetrahydrobostrycin Type: Anthracenes. C16H20O7 Red cryst., mp 234–235 °C, [α]D20 = −87.8° (c = 0.11, DMSO) (Fusarium sp.), [α]D18 = −69.3° (c = 0.4, MeOH) (Aspergillus sp.). Source: Marine-derived fungus Aspergillus sp. from an unidentified alga (Indonesia), mangrove-derived fungus Fusarium sp. ZH-210 from an unidentified mangrove (sediment). Pharm: Antibacterial (100 μg/disc, Staphylococcus aureus, IZD = 12 mm). Ref: J. Z. Xu, et al, J. Antibiot., 2008, 61, 415│Y. Chen, et al, Magn. Reson. Chem., 2009, 47, 362│K. Trisuwan, et al, JNP, 2010, 73, 1507 OH

O

H

OH OH

O OH

OH

H

868 Fusaranthraquinone Type: Anthracenes. C16H20O7 Source: Marine-derived fungi Fusarium sp. PSU-F14. Pharm: antifungal (Cryptococcus neoformans and Microsporum gypseum, MIC = 200 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507 OH

OH

O

H OH OH

OH

O

H

869 9α-Hydroxydihydrodesoxybostrycin Type: Anthracenes. C16H20O7 Source: Marine-derived fungi Fusarium sp. PSU-F14. Pharm: Cytotoxic (KB, IC50 = 19 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 15 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, IC50 = 57 μmol/L, control Ellipticine, IC50 = 4.47 μmol/L); antibacterial (Staphylococcus aureus and MRSA, MIC = 350 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507

2.10 Anthracene Derivatives

OH

OH O

295

H OH

OH

O

OH

H

870 9α-Hydroxyhalorosellinia A Type: Anthracenes. C16H20O8 Source: Marine-derived fungi Fusarium sp. PSU-F14. Pharm: Antiplasmodial (in vitro Plasmodium falciparum K1, IC50 = 25 μmol/L, control Dihydroartemisinin, IC50 = 0.004 μmol/L); antituberculosis (Mycobacterium tuberculosis, MIC = 39 μmol/L, control Isoniazid, MIC = 0.17–0.34 μmol/L); cytotoxic (KB, IC50 = 49 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 62 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, IC50 = 54 μmol/L, control Ellipticine, IC50 = 4.47 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507 OH

OH

O

H OH

OH

O

H

OH OH

871 Physcion-10,10′-cis–bianthrone Type: Anthracenes. C32H26O8 Source: Marine-derived fungus Aspergillus glaucus. Pharm: Cytotoxic (MTT assay, HL60, IC50 = 44.0 μmol/L; SRB method, A549, IC50 = 14.2 μmol/L). Ref: L. Du, et al, JNP, 2008, 71, 1837 OH

O

OH

10

O H

H

O 10'

OH

O

OH

H-10, H-10' cis

872 Physcion-10,10′-trans–bianthrone Type: Anthracenes. C32H26O8 Source: Marine-derived fungus Aspergillus glaucus. Pharm: Cytotoxic (MTT assay, HL60, IC50 = 7.8 μmol/L; SRB method, A549, IC50 = 9.2 μmol/L). Ref: L. Du, et al, JNP, 2008, 71, 1837

296

2 Aromatic Metabolites

OH

O

OH

10

O H

H

O 10'

OH

O

OH

H-10, H10' trans

873 Trioxacarcin A Antibiotic DC 45A Type: Anthracenes. C42H52O20 Yellow powder +2H2O, mp 177–183 °C (dec), [α]D25 = −15.3° (c = 1, EtOH). Source: Marine-derived streptomycete Streptomyces sp. B8652, terrestrial streptomycetes (Streptomyces ochraceus and Streptomyces bottropensis). Pharm: Antibacterial (gram-positive and -negative bacteria); LD50 (mus, ipr) = 1 mg/kg. Ref: F. J. Tomita, J. Antibiot., 1981, 34, 1519; 1525│R. P. Maskey, et al, J. Antibiot., 2004, 57, 771 O 4'

O

OH

O O O H O

O 15 11

OH H

O

O

O

OH

O

13

O

14 17

O

O

O OH OH

874 Trioxacarcin B Antibiotic DC 45B1 Type: Anthracenes. C42H54O21 Yellow powder +2H2O, mp 193–194 °C (dec), [α]D25 = −122.7° (c = 1, CHCl3). Source: Marine-derived streptomycete Streptomyces sp. B8652, terrestrial streptomycetes (Streptomyces ochraceus and Streptomyces bottropensis). Pharm: Antibacterial (Bacillus subtilis, Streptomyces viridochromogenes, Staphylococcus aureus and Escherichia coli, MIC = 0.15–2.5 μg/mL); cytotoxic; LD50 (mus, ipr) = 100 mg/kg. Ref: F. J. Tomita, J. Antibiot., 1981, 34, 1519; 1525│R. P. Maskey, et al, J. Antibiot., 2004, 57, 771

2.10 Anthracene Derivatives

O 4'

297

O

OH

O O O H O

O 15 11

OH H

O

O

O

OH

O

13

HO

14 17

O

O

O

HO

OH OH

875 Trioxacarcin C Antibiotic DC 45B2 Type: Anthracenes. C42H54O20 Yellow powder +2H2O, mp 181– 182 °C (dec), [α]D25 = −10° (c = 0.2, EtOH). Source: Marine-derived streptomycete Streptomyces sp. B8652, terrestrial streptomycetes (Streptomyces ochraceus and Streptomyces bottropensis). Pharm: Antibacterial (gram-positive and -negative bacteria); cytotoxic; LD50 (mus, ipr) = 2 mg/kg, LD50 (mus, ivn) = 1 mg/kg. Ref: F. J. Tomita, J. Antibiot., 1981, 34, 1519; 1525│R. P. Maskey, et al, J. Antibiot., 2004, 57, 771 O

O

OH

4'

O O O H O

O 15 11

OH H

O

O

O

OH

O

13

O

14

O

HO

17

O OH OH

876 Austrocortirubin Type: 1,4-Anthraquinones. C16H16O7 Dark red needles (C6H6/petrol), mp 193–195 °C, [α]D20 = +34° (c = 0.543, CHCl3), [α]D20 = +109° (c = 0.824, EtOH). Source: Marinederived fungus Fusarium sp. from gorgonian sea fan Annella sp. (Koh Hin Ran Pet, Surat Thani Province, Thailand), marine-derived fungus Fusarium sp. PSU-F14, terrestrial fungi (toadstools Cortinarius toadstools and Dermocybe splendid). Pharm: Cytotoxic (KB, inactive, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 6.3 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, inactive, control

298

2 Aromatic Metabolites

Ellipticine, IC50 = 4.47 μmol/L); antibacterial (Staphylococcus aureus and MRSA, MIC = 350 μmol/L). Ref: M. A. Archard, et al, Phytochemistry, 1985, 24,2755│M. Gill, et al, Tet. Lett., 1985, 26, 2593│K. Trisuwan, et al, JNP, 2010, 73, 1507 O

OH

O OH

O

OH

OH

877 Bostrycin Rhodosporin Type: 1,4-Anthraquinones. C16H16O8 Red cryst. (Py aq), mp 222–224 °C. Source: Marine-derived fungi Aspergillus sp. from an unidentified alga (Indonesia) and Fusarium sp. PSU-F14 and O5F13. Pharm: Antiplasmodial (in vitro Plasmodium falciparum K1, IC50 = 98 μmol/L, control Dihydroartemisinin, IC50 = 0.004 μmol/L); cytotoxic (KB, IC50 = 0.9 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 2.7 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, IC50 = 4.2 μmol/L, control Ellipticine, IC50 = 4.47 μmol/L); inducer of mitochondria-mediated apoptosis (yeast Saccharomyces cerevisiae); LD50 (mus, ipr) = 200 mg/kg. Ref: B. Beagley, et al, Chem. Comm., 1989, 17│J. Xu, et al, Yakugaku Zasshi, 2006, 126, 234│J. Z. Xu, et al, J. Antibiot., 2008, 61, 415│K. Trisuwan, et al, JNP, 2010, 73, 1507 O

OH OH

O 10

9

5

6

OH

OH

OH O

878 5,7-Dideoxybostrycin Type: 1,4-Anthraquinones. C16H16O6 Source: Marine-derived fungus Nigrospora sp. 1403 from an unidentified sea anemone. Pharm: Antibacterial (Bacillus subtilis, MIC = 0.625 μmol/L, Bacillus cereus, MIC = 10.0 μmol/L, Micrococcus luteus, MIC = 20.0 μmol/L, Staphylococcus albus, MIC = 5.00 μmol/L, Staphylococcus aureus, MIC = 2.50 μmol/L, Micrococcus tetragenus, MIC = 1.25 μmol/L, Escherichia coli, MIC = 2.50 μmol/L, Vibrio anguillarum, MIC = 2.50 μmol/L, Vibrio parahaemolyticus, MIC = 1.25 μmol/L). Ref: K. L. Yang, et al, JNP, 2012, 75, 935 O

OH

O OH

O

OH

2.10 Anthracene Derivatives

299

879 5-Deoxybostrycin Type: 1,4-Anthraquinones. C16H16O7 Source: Marine-derived fungus Nigrospora sp. from an unidentified sea anemone (Weizhou I., Guangxi, China). Pharm: Antibacterial (Bacillus cereus, strong); cytotoxic (A549, strong). Ref: K. -L. Yang, et al, JNP, 2012, 75, 935 O

OH

O OH OH O

OH

880 Nigrosporin B Type: 1,4-Anthraquinones. C16H16O6 Yellow oil, [α]D28 = −16.7° (c = 0.02, CHCl3). Source: Marine-derived fungi Fusarium sp. PSU-F14. Pharm: Antiplasmodial (in vitro Plasmodium falciparum K1, IC50 = 13 μmol/L, control Dihydroartemisinin, IC50 = 0.004 μmol/L); antituberculosis (Mycobacterium tuberculosis, MIC = 41 μmol/L, control Isoniazid, MIC = 0.17–0.34 μmol/L); cytotoxic (KB, IC50 = 88 μmol/L, control doxorubicin, IC50 = 0.33 μmol/L; MCF7, IC50 = 5.4 μmol/L, control doxorubicin, IC50 = 2.18 μmol/L; Vero, IC50 = 29 μmol/L, control Ellipticine, IC50 = 4.47 μmol/L). Ref: K. Trisuwan, et al, JNP, 2010, 73, 1507 O OH

O

OH O

OH

881 Albopunctatone Type: 9,10-Anthraquinones. C28H16O8 Source: Ascidian Didemnum albopunctatum (Swain Reefs, Great Barrier Reef). Pharm: Antiplasmodial (CSPF and CRPF). Ref: A. R. Carroll, et al, JNP, 2012, 75, 1206 OH

OH

O

O

OH

OH OH

O

300

2 Aromatic Metabolites

882 Alterporriol K Type: 9,10-Anthraquinones. C32H26O11 Red powder, [α]D25 = +690° (c = 1.0, MeOH). Source: Mangrove-derived fungus Alternaria sp. from mangrove Aegiceras corniculatum (Guangdong, China). Pharm: Cytotoxic (MTT assay, MDA-MB-435, IC50 = 26.97 μmol/L; MCF7, IC50 = 29.11 μmol/L). Ref: C. -H. Huang, et al, Mar. Drugs, 2011, 9, 832 O

OH O

O

OH

O

OH

HO O

O OH

883 Alterporriol L Type: 9,10-Anthraquinones. C32H26O12 Red powder, [α]D25 = +30° (c = 1.0, MeOH). Source: Mangrove-derived fungus Alternaria sp. from mangrove Aegiceras corniculatum (Guangdong, China). Pharm: Cytotoxic (MTT assay, MDA-MB-435, IC50 = 13.11 μmol/L; MCF7, IC50 = 20.04 μmol/L). Ref: C. -H. Huang, et al, Mar. Drugs, 2011, 9, 832 O

OH O

O

H

OH OH

HO O

O OH OH

O

884 Alterporriol P Type: 9,10-Anthraquinones. C32H26O12 Source: Marine-derived fungus Alternaria sp. from soft coral Sarcophyton sp. (Weizhou coral reef, Giuangxi, China). Pharm: Cytotoxic (HTCLs cells). Ref: C. -J. Zheng, et al, JNP, 2012, 75, 189 O O

OH OH

O O

OH O

O HO

OH OH

2.10 Anthracene Derivatives

301

885 Alterporriol Q Type: 9,10-Anthraquinones. C32H22O10 Source: Marine-derived fungus Alternaria sp. from soft coral Sarcophyton sp. ZJ-2008003 (Weizhou coral reef, Giuangxi, China). Pharm: Antiviral (porcine reproductive and respiratory syndrome (PRRS) virus, IC50 = 39 μmol/L). Ref: C. -J. Zheng, et al, JNP, 2012, 75, 189│S. Z. Moghadamtousi, et al, Mar. Drugs, 2015, 13, 4520 (rev) O O

OH O HO

OH

O

O

O HO

886 Antibiotic BE 43472A Type: 9,10-Anthraquinones. C32H24O10 Amorph. yellow solid, [α]D23 = +538° (c = 0.23, CHCl3). Source: Marine-derived streptomycete Streptomyces sp. N1-78-1. Pharm: Antibacterial; cytotoxic. Ref: A. M. Socha, et al, BoMC, 2006, 14, 8446│A. M. Socha, et al, JNP, 2006, 69, 1070│K. C. Nicolaou, et al, JACS, 2009, 131, 14812 OH

O

OH

HO 4

HO

O O O OH 8'

O

887 7,7ʹ-Bihelminthosporin 2,2ʹ-Bihelminthosporin; Antibiotic 2240A Type: 9,10-Anthraquinones. C30H18O10 Orange-red solid, mp 300 °C, [α]D20 = +62.5° (c = 0.08, dioxin). Source: An unidentified mangrove-derived fungus No. 2240 (endophytic). Pharm: hTopo l isomerase inhibitor. Ref: N. Tan, et al, J. Asian Nat. Prod. Res., 2008, 10, 607│N. Tan, et al, Yingyong Huaxue, 2009, 26, 277

302

2 Aromatic Metabolites

OH

OH

O

OH

O

OH

O

OH

OH

O

888 Chrysophanol 1,8-Dihydroxy-3-methylanthraquinone Type: 9,10-Anthraquinones. C15H10O4 Goldenyellow plates (C6H6), mp 200–201 °C, mp 196 °C. Source: Marine-derived fungus Monodictys sp. from urchin Anthocidaris crassispina (Japan waters), annelid (spoon worm) Urechis unicinctus, mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382, widely distributed in plants. Pharm: Antimicrobial; cathartic; cytotoxic (drug-sensitive parental KB, IC50 = 174.87 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 331.97 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: A. A. El-Beih, et al, CPB, 2007, 55, 1097│J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469 OH

O

OH

O

889 1,8-Dihydroxyanthraquinone Dantron Type: 9,10-Anthraquinones. C14H8O4 Square orange plates (Me2CO), mp 193 °C. Source: Marine-derived fungus Beauveria bassiana from an unidentified sponge (Iriomote I., Okinawa, Japan), bryozoans Dakaria subovoidea (Japan waters) and Watersipora subtorquata, mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382, terrestrial plants (Rheum palmatum, Xyris semifuscata, Cinchona ledgeriana and Pyrrhalta luteola). Pharm: Antioxidant; cathartic; cytotoxic (drug-sensitive parental KB, IC50 = 56.56 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 109.15 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: M. P. Kuntsmann, et al, JOC, 1966, 31, 2920│T. Shindo, et al, Experientia, 1993, 49, 177│J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469│H. Yamazaki, et al, Mar. Drugs, 2012, 10, 2691│CRC Press, DNP on DVD, 2012, version 20.2 OH

O

O

OH

2.10 Anthracene Derivatives

303

890 1,7-Dihydroxy-2,4-dimethoxy-6-methylanthraquinone Type: 9,10-Anthraquinones. C17H14O6 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 > 500 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 301.47 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469 O

OH O

HO

O

O

891 1,4-Dihydroxy-2-methoxy-7-methylanthraquinone Austrocortinin Type: 9,10-Anthraquinones. C16H12O5 Red cryst. (CHCl3/petrol), mp 237–240 °C, mp 208–209 °C. Source: Marine-derived fungus Halorosellinia sp. 1403 (decayed wood in Hong Kong and a salt lake in Bahamas), mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382, terrestrial fungi (Cortinarius spp.). Pharm: Cytotoxic (drug-sensitive parental KB, IC50 = 305.14 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 > 500 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: M. Archard, et al, Phytochemistry, 1985, 24, 2755│Z. -G. She, et al, Acta Cryst. E, 2006, 62, 3737│X. -K. Xia, et al, Magn. Reson. Chem., 2007, 45, 1006│J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469 OH

O

OH

O

O

892 1,3-Dihydroxy-6-methoxy-8-methylanthraquinone Type: 9,10-Anthraquinones. C16H12O5 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 = 38.05 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 34.64 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469 O

O

OH

OH O

304

2 Aromatic Metabolites

893 1,4-Dihydroxy-6-methylanthraquinone 6-Methylquinizarin Type: 9,10-Anthraquinones. C15H10O4 Orange cryst. (AcOH), red needles (EtOH), mp 175–177 °C, mp 167–168 °C. Source: Marine-derived fungus Halorosellinia sp. 1403 (decayed wood in Hong Kong and a salt lake in Bahamas), terrestrial plant (Rubia cordifolia, root), mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 = 114.09 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 86.45 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: A. M. Tessier, et al, PM, 1981, 41, 337│X. -K. Xia, et al, Magn. Reson. Chem., 2007, 45, 1006│ J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469 OH

O

OH

O

894 1,3-Dihydroxy-6-methyl-8-methoxyanthraquinone Type: 9,10-Anthraquinones. C16H12O5 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 > 500 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 109.81 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469 O

O

OH

OH O

895 1,3-Dimethoxy-6-methylanthraquinone Type: 9,10-Anthraquinones. C17H14O4 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 = 57.32 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 90.86 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469 O

O

O O

2.10 Anthracene Derivatives

305

896 6,8-Di-O-methylaverantin Type: 9,10-Anthraquinones. C22H24O7 Source: Marine-derived fungus Aspergillus versicolor EN-7from brown alga Sargassum thunbergii (Qingdao, Shandong, China). Pharm: Antibacterial (Escherichia coli, 20 μg/disk, IZ = 7 mm). Ref: Y. Zhang, et al, Biosci., Biotechnol., Biochem., 2012, 76, 1774 O

O

OH

OH

O

OH O

897 Dioxamycin Type: 9,10-Anthraquinones. C38H40O15 Orange amorph. powder, mp 176–178 °C (dec), [α]D23 = +43.8° (c = 0.05, MeOH), [α]D24 = +49° (c = 0.2, MeOH). Source: Marine-derived streptomycete Streptomyces fradiae PTZ00025 (sediment, source unspecified). Pharm: Antibacterial (gram-positive bacteria); cytotoxic. Ref: R. Sawa, et al, J. Antibiot., 1991, 44, 396│W. Xin, et al, Mar. Drugs, 2012, 10, 2388 OH O

OH O

O 3

O

OH OH

O

O

O

OH

OH

O

O

898 Emodin 1,3,8-Trihydroxy-6-methylanthraquinone Type: 9,10-Anthraquinones. C15H10O5 Orange or yellow-brown needles (Py aq or MeOH), mp 266–268 °C, mp 254–256 °C. Source: Marine-derived fungus Monodictys sp. from urchin Anthocidaris crassispina (Japan waters), mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382 and occurs in terrestrial plants. Pharm: Antimicrobial; antineoplastic; cathartic; monoamine oxidase inhibitor; cytotoxic (drug-sensitive parental KB, IC50 > 500 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 > 500 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: A. A. El-Beih, et al, CPB, 2007, 55, 1097│ J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469

306

2 Aromatic Metabolites

OH

O

OH

OH O

899 Evariquinone Type: 9,10-Anthraquinones. C16H12O6 Orange needles, mp 238–242 °C (subl). Source: Marine-derived fungus Emericella variecolor from sponge Haliclona valliculata. Pharm: Antiproliferative (KB and NCI-H460, 3.16 μg/mL effective). Ref: G. Bringmann, et al, Phytochemistry, 2003, 63, 437│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) OH

O

O

HO

HO O

900 Fradimycin A Type: 9,10-Anthraquinones. C39H42O15 Orange amorph. powder, [α]D23 = +39.5° (c = 0.05, MeOH). Source: Marine-derived streptomycete Streptomyces fradiae PTZ00025 (sediment, source unspecified). Pharm: Antibacterial (Staphylococcus aureus, MIC = 2.0–6.0 μg/mL); cytotoxic (hmn colon HCT15, IC50 = (0.52 ± 0.11)μmol/L; hmn colon SW620, IC50 = (6.46 ± 1.44)μmol/L; Rat glioma C6, IC50 = (1.28 ± 0.37)μmol/L). Ref: W. Xin, et al, Mar. Drugs, 2012, 10, 2388 OH O O OH

O O

OH

O

O

OH

O 3

O

OH

O

O

901 Fradimycin B Type: 9,10-Anthraquinones. C38H38O14 Orange amorph. powder, [α]D23 = +36.3° (c = 0.05, MeOH). Source: Marine-derived streptomycete Streptomyces fradiae PTZ00025 (sediment, source unspecified). Pharm: Antibacterial (Staphylococcus aureus, MIC = 2.0–6.0 μg/mL); cytotoxic (Hmn colon HCT15, IC50 = (0.13 ± 0.04)μmol/L;

2.10 Anthracene Derivatives

307

hmn colon SW620, IC50 = (4.33 ± 1.56)μmol/L; rat glioma C6, IC50 = (0.47 ± 0.09)μmol/L). Ref: W. Xin, et al, Mar. Drugs, 2012, 10, 2388 OH O O OH

OH O

O

O

OH OH

O 3

O

O

O

902 Galvaquinone B Type: 9,10-Anthraquinones. C21H20O6 Source: Marine-derived streptomycete Streptomyces spinoverrucosus (sediment, Trinity Bay, Galveston, Texas). Pharm: Epigenetic modulatory activity; cytotoxic (NSCLC, Calu3 and H2887, moderate). Ref: Y. Hu, et al, JNP, 2012, 75, 1759

OH

O

OH

O

OH

O

903 Halawanone C Type: 9,10-Anthraquinones. C21H20O7 Source: Marine-derived streptomycete Streptomyces sp. BD-18T (shallow water sediment on Oahu). Pharm: Antibacterial (Bacillus subtilis, Staphylococcus aureus, gram-positive bacteria). Ref: P. W. Ford, et al, JNP, 1998, 61, 1232 O O

OH O

OH

OH

O

904 Halawanone D Type: 9,10-Anthraquinones. C22H22O7 Source: Marine-derived streptomycete Streptomyces sp. BD-18T (shallow water sediment on Oahu). Pharm: Antibacterial (Bacillus subtilis, Staphylococcus aureus, gram-positive bacteria). Ref: P. W. Ford, et al, JNP, 1998, 61, 1232

308

2 Aromatic Metabolites

O O

OH O

OH

OH

O

905 1-Hydroxy-2,4-dimethoxy-7-methylanthraquinone Type: 9,10-Anthraquinones. C17H14O5 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 = 68.39 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 243.69 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs 2010, 8, 1469 O

OH O

O

O

906 Isorhodoptilometrin-1-methyl ether Type: 9,10-Anthraquinones. C18H16O6 Source: Marine-derived fungus Aspergillus versicolor from green alga Halimeda opuntia (Rass Mohamed, south Sinai, Egypt). Pharm: Antibacterial (3 gram-positive bacteria, 50 μg/disk: Bacillus cereus, IZ = 2 mm, Bacillus subtilis, IZ = 3 mm, Staphylococcus aureus, IZ = 5 mm). Ref: U. W. Hawas, et al, Arch. Pharmacal Res., 2012, 35, 1749 O

O

OH

OH OH O

907 1-Methoxy-3-methyl-8-hydroxyanthraquinone Type: 9,10-Anthraquinones. C16H12O4 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 > 500 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 185.68 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs, 2010, 8, 1469

2.10 Anthracene Derivatives

OH

O

309

O

O

908 MK844-mF10 Type: 9,10-Anthraquinones. C38H38O13 Orange amorph. powder, [α]D23 = +39.6° (c = 0.01, MeOH). Source: Marine-derived streptomycete Streptomyces fradiae PTZ00025 (sediment, source unspecified). Pharm: Antibacterial (Staphylococcus aureus, MIC = 2.0–6.0 μg/mL); cytotoxic (Hmn colon HCT15, IC50 = (0.30 ± 0.07)μmol/L; hmn colon SW620, IC50 = (4.39 ± 0.93)μmol/L; rat glioma C6, IC50 = (1.31 ± 0.32)μmol/L). Ref: W. Xin, et al, Mar. Drugs, 2012, 10, 2388 OH O O OH

O

OH O

O OH

O 3

O

O

O

909 Monodictyquinone 1,8-Dihydroxy-2-methoxy-6-methylanthraquinone Type: 9,10-Anthraquinones. C16H12O5 Yellow solid. Source: Marine-derived fungus Monodictys sp. from urchin Anthocidaris crassispina (Japan waters). Pharm: Antibacterial (Paper disks diameter 6 mm, impregnated with compound 2.5 μg, were incubated on agar plates containing Microorganisms: Bacillus subtilis, IZD = 7 mm; Escherichia coli, IZD = 8 mm); antifungal (yeast Candida albicans, IZD = 7 mm). Ref: A. A. El-Beih, et al, CPB, 2007, 55, 1097 OH

O

OH

O

O

910 Pachybasin 1-Hydroxy-3-methylanthraquinone Type: 9,10-Anthraquinones. C15H10O3 Yellow needles, mp 175–176 °C, mp 234–237 °C. Source: Marine-derived fungus Halorosellinia sp. 1403 (decayed wood in Hong Kong and a salt lake in Bahamas), mangrove-derived

310

2 Aromatic Metabolites

endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (KB, IC50 = 1.40 μg/mL; KBV200, IC50 = 2.58 μg/mL); cytotoxic (drug-sensitive parental KB, IC50 = 3.17 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 3.21 μmol/L, Adriamycin, IC50 = 1.894 μmol/L, might induce apoptosis via a mitochondrial pathway). Ref: X. -K. Xia, et al, Magn. Reson. Chem., 2007, 45, 1006│A. A. El-Beih, et al, CPB, 2007, 55, 1097│J. Y. Zhang, et al, Mar. Drugs 2010, 8, 1469 O

OH

O

911 1,2,3,6,8-Pentahydroxy-7-(1R-methoxyethyl)anthraquinone Type: 9,10-Anthraquinones. C17H14O8 Orange-yellow powder, [α]D = −380.2° (c = 0.1, EtOH). Source: Marine-derived fungus Microsphaeropsis sp. from sponge Aplysina aerophoba (Mediterranean Sea). Pharm: Kinases inhibitor (PKC-ε, IC50 = 54.0 μmol/L; CDK4/cyclin D1, IC50 = 37.5 μmol/L; and EGFR, IC50 = 41.0 μmol/L). Ref: G. Brauers, et al, JNP, 2000, 63, 739 OH

O

OH

O

HO

HO

OH O

912 Physcion Type: 9,10-Anthraquinones. C16H12O5 Orange needles (EtOAc/petrol), mp 209–210 °C. Source: Mangrove-derived fungus Alternaria sp. from mangrove Aegiceras corniculatum (Guangdong, China), an unidentified mangrove-derived fungus 2526 (South China Sea), and widely distributed in lichens, e.g. Parmelia spp., and higher plants. Pharm: Antimicrobial; possesses cathartic properties; LD50 (mus, ipr) = 10 mg/kg. Ref: M. Saleem, et al, NPR, 2007, 24, 1142 (rev)│C. -H. Huang, et al, Mar. Drugs, 2011, 9, 832 O O

OH

O

OH

2.10 Anthracene Derivatives

311

913 Questin 3-α-D-ribofuranoside 3-O-(a-D-Ribofuranosyl)questin Type: 9,10-Anthraquinones. C21H20O9 Amorph. orange powder, [α]D25 = +89.4° (c = 0.02, MeOH). Source: Mangrove-derived fungus Eurotium rubrum from semimangrove Hibiscus tiliaceus (China waters). Pharm: Antioxidant (DPPH scavenger, moderate). Ref: D. -L. Li, et al, J. Microbiol. Biotechnol., 2009, 19, 675 OH

O

O

O HO

O

O

OH OH

914 Tetrahydroaltersolanol C Type: 9,10-Anthraquinones. C16H20O6 Source: Marine-derived fungus Alternaria sp. ZJ-2008003 from soft coral Sarcophyton sp. (Weizhou coral reef, Giuangxi, China). Pharm: Antiviral (porcine reproductive and respiratory syndrome (PRRS) virus, IC50 = 65 μmol/L). Ref: C. -J. Zheng, et al, JNP, 2012, 75, 189│S. Z. Moghadamtousi, et al, Mar. Drugs, 2015, 13, 4520 (rev) OH O H

OH OH

H OH

O

915 1,3,6,8-Tetrahydroxy-2-(1-hydroxyethyl)anthraquinone Type: 9,10-Anthraquinones. C16H12O7 Orange-yellow powder, [α]D = +151.5° (c = 0.1, EtOH). Source: Marine-derived fungus Microsphaeropsis sp. from sponge Aplysina aerophoba (Mediterranean Sea). Pharm: Kinases inhibitors (PKC-ε, IC50 = 18.5 μmol/L; CDK4/cyclin D1, IC50 = 43.5 μmol/L; and EGFR, IC50 = 37.5 μmol/L). Ref: G. Brauers, et al, JNP, 2000, 63, 739 OH

O

HO

OH

OH

OH O

312

2 Aromatic Metabolites

916 1,3,6,8-Tetrahydroxy-2-(1-methoxyethyl)anthraquinone Type: 9,10-Anthraquinones. C17H14O7 Orange-yellow powder, [α]D = −193.8° (c = 0.1, EtOH). Source: Marine-derived fungus Microsphaeropsis sp. from sponge Aplysina aerophoba (Mediterranean Sea). Pharm: Kinases inhibitors (PKC-ε, IC50 = 27.0 μmol/L; CDK4/cyclin D1, IC50 = 22.5 μmol/L; and EGFR, IC50 = 27.5 μmol/L). Ref: G. Brauers, et al, JNP, 2000, 63, 739 OH

O

OH

HO

O

OH O

917 Trichodermaquinone Type: 9,10-Anthraquinones. C15H14O6 Source: Marine-derived fungus Trichoderma aureoviride PSU-F95 from gorgonian sea fan Annella sp. (Similan Is., Thailand). Pharm: Antibacterial (MRSA, MIC = 8 μg/mL). Ref: N. Khamthong, et al, Arch. Pharmacal Res., 2012, 35, 461 O

OH

HO

HO O

OH

918 1,3,8-Trihydroxyanthraquinone Type: 9,10-Anthraquinones. C14H8O5 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 > 500 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200, IC50 = 72.60 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs 2010, 8, 1469 OH

O

OH

OH O

919 1,4,7-Trihydroxy-2-methoxy-6-methylanthraquinone Type: 9,10-Anthraquinones. C16H12O6 Source: Mangrove-derived endophytic fungi Halorosellinia sp. 1403 and Guignardia sp. 4382. Pharm: Cytotoxic (drug-sensitive parental KB, IC50 > 500 μmol/L, control Adriamycin, IC50 = 0.034 μmol/L; KBV200,

2.10 Anthracene Derivatives

313

IC50 > 500 μmol/L, Adriamycin, IC50 = 1.894 μmol/L). Ref: J. Y. Zhang, et al, Mar. Drugs 2010, 8, 1469 O

OH O

HO

O

OH

920 γ-Indomycinone Type: Pyrano[b]anthraquinones. C22H18O6 Yellow powder. Source: Marine-derived streptomycete Streptomyces sp. (psychrophilic, cold water, depth of 4680 m sediment core, culture broth). Pharm: Cytotoxic (hmn colon cancer line HCT116); inhibits DNA synthesis; pluramycin antibiotics. Ref: R. W. Schumacher, et al, JNP, 1995, 58, 613│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) 14S

16

HO OH

O

O O

13

8

O

921 δ-Indomycinone Type: Pyrano[b]anthraquinones. C24H22O7 Yellow solid, mp 181 °C. Source: Marinederived streptomycete Streptomyces sp. B8300 (Lagoon, Gulf of Mexico), marinederived streptomycete Streptomyces sp. (psychrophilic, cold water, depth of 4680 m sediment core, culture broth). Pharm: Antioxidant.antibiotic (pluramycin-class); Ref: R. W. Schumacher, et al, JNP, 1995, 58, 613│M. A. F. Biabani, et al, J. Antibiot., 1997, 50, 874│L. F. Tietze, et al, Chem. Eur. J., 2007, 13, 9939│M. D. Lebar, et al, NPR, 2007, 24, 774 (rev) OH

HO OH

O

O O

O

314

2 Aromatic Metabolites

922 Saliniquinone A Type: Pyrano[b]anthraquinones. C23H16O7 Yellow solid, [α]D = +440° (c = 0.2, CHCl3). Source: Marine-derived bacterium Salinispora arenicola CNS-325 (sediment, Palau, Oceania). Pharm: Cytotoxic (HCT116, potent); antibacterial (MRSA, weak). Ref: B. T. Murphy, et al, Aust. J. Chem., 2010, 63, 929 O 14

OH

O

16 17

O O OH 13

O

923 Aranciamycin Antibiotic SM 173A Type: Anthracyclinones. C27H28O12 Orange-yellow cryst. (MeOH), mp 240 °C (dec), [α]D = +149.5° (c = 0.5, MeOH). Source: Marine-derived streptomycete Streptomyces sp. from sponge Haliclona sp. (Tateyama City, Chiba, Japan), terrestrial streptomycetes (Streptomyces echinatus and Streptomyces chromofuscus). Pharm: Cytotoxic (HeLa, IC50 = 2.7 μmol/L; HL60, IC50 = 4.1 μmol/L); antibacterial (gram-positive bacteria). Ref: K. Schmidt-Bäse, et al, Acta Cryst. C, 1993, 49, 250│K. Motohashi, et al, JNP, 2010, 73, 755 O

O OH

O OH

O

OH

O

O

HO HO

O

924 Tetracenoquinocin Type: Anthracyclinones. C26H24O9 Red oil, [α]D25 = −69° (c = 0.1, CHCl3). Source: Marine-derived streptomycete Streptomyces sp. from sponge Haliclona sp. (Tateyama City, Chiba, Japan). Pharm: Cytotoxic (HeLa, IC50 = 120 μmol/L; HL60, IC50 = 210 μmol/L). Ref: K. Motohashi, et al, JNP, 2010, 73, 755

2.11 Extended Quinones

315

O

OH

O

OH

O

O

HO HO

O

2.11 Extended Quinones 925 Aspergiolide A Type: Extended quinones. C25H16O9 Red needles (CHCl3/MeOH). Source: Mangrovederived fungus Aspergillus glaucus HB1-119 (cultured from sediment around mangrove roots, China). Pharm: Cytotoxic (MTT method: HL60, IC50 = 0.28 μmol/L; P388, IC50 = 35.0 μmol/L; SRB method: A549, IC50 = 0.13 μmol/L; Bel7402, IC50 = 7.5 μmol/L). Ref: L. Du, et al, Tetrahedron, 2007, 63, 1085; 2008, 64, 4657 (corrigendum) OH

OH

O

8

HO O

O O OH

OH

926 Aspergiolide B Type: Extended quinones. C26H18O9 Red solid (MeOH). Source: Mangrove-derived fungus Aspergillus glaucus HB1-119 (cultured from sediment around mangrove roots, China). Pharm: Cytotoxic (MTT assay, HL60, IC50 = 0.51 μmol/L; SRB method, A549, IC50 = 0.24 μmol/L). Ref: L. Du, et al, JNP, 2008, 71, 1837

316

2 Aromatic Metabolites

O

O

OH

8

HO O

O O OH

OH

2.12 Phenalenes 927 Conioscleroderolide Type: Phenalenes. C18H16O6 Source: Marine-derived fungus Coniothyrium cereale from green alga Enteromorpha sp. (Fehmarn I., Baltic Sea, Germany). Pharm: Antibacterial (Staphylococcus aureus); hmn leukocyte elastase (HLE) inhibitor. Ref: M. F. Elsebai, et al, Org. Biomol. Chem., 2011, 9, 802 O O

O HO

OH

O

928 (E)-Coniosclerodinol Type: Phenalenes. C18H16O7 Source: Marine-derived fungus Coniothyrium cereale from green alga Enteromorpha sp. (Fehmarn I., Baltic Sea, Germany). Pharm: Antibacterial (Mycobacterium phlei). Ref: M. F. Elsebai, et al, Org. Biomol. Chem., 2011, 9, 802

2.12 Phenalenes

O

317

O

O

HO

OH

O

OH

929 (Z)-Coniosclerodinol Type: Phenalenes. C18H16O7 Source: Marine-derived fungus Coniothyrium cereale from green alga Enteromorpha sp. (Fehmarn I., Baltic Sea, Germany). Pharm: Antibacterial (Mycobacterium phlei, (20 μg/disk, IZ = 16 mm). Ref: M. F. Elsebai, et al, Org. Biomol. Chem., 2011, 9, 802 O

O

O

HO

OH

O Z

OH

930 (15S,17S)-(−)-Sclerodinol Type: Phenalenes. C18H16O7 Source: Marine-derived fungus Coniothyrium cereale. Pharm: Antibacterial (Mycobacterium phlei, 20 μg/disk, IZ = 20 mm). Ref: M. F. Elsebai, et al, Org. Biomol. Chem., 2011, 9, 802 O

O

O

HO

OH

O

OH

931 Sculezonone A Type: Phenalenes. C20H20O8 Amorph. yellow solid, [α]D23 = +45° (c = 0.2, MeOH). Source: Marine-derived fungus Penicillium sp. (cultured broth) from mussel Mytilus coruscus (Okinawa). Pharm: DNA polymerases inhibitor (bovine DNA polymerase a

318

2 Aromatic Metabolites

and c; moderate activity for bovine DNA polymerase). Ref: K. Komatsu, et al, JNP, 2000, 63, 408│M. Perpelescu, et al, Biochemistry, 2002, 41, 7610│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) O HO

OH O OH

OH

O O

932 Sculezonone B Type: Phenalenes. C20H20O9 Amorph. yellow solid, [α]D23 = +130° (c = 0.2, MeOH). Source: Marine-derived fungus Penicillium sp. (cultured broth) from mussel Mytilus coruscus (Okinawa). Pharm: DNA polymerases inhibitor (bovine DNA polymerase a and c; moderate activity for bovine DNA polymerase). Ref: K. Komatsu, et al, JNP, 2000, 63, 408│M. Perpelescu, et al, Biochemistry, 2002, 41, 7610│M. Saleem, et al, NPR, 2007, 24, 1142 (rev) O HO

OH O OH

HO OH

O O

2.13 Acenaphthalenes 933 Coniosclerodione Type: Acenaphthalenes. C18H16O5 Source: Marine-derived fungus Coniothyrium cereale from green alga Enteromorpha sp. (Fehmarn I., Baltic Sea, Germany). Pharm: Antibacterial (20 μg/disk: Micrococcus luteus, IZ = 10 mm, Mycobacterium phlei, IZ = 12 mm; Staphylococcus aureus, MIC = 65.7 μmol/L). Ref: M. F. Elsebai, et al, Org. Biomol. Chem., 2011, 9, 802

2.14 Miscellaneous Polycyclic Aromatics

319

O

O

HO

OH

O

934 (−)-Sclerodione Type: Acenaphthalenes. C18H16O5 Bright-red or red-brown cryst. (CH2Cl2/hexane), mp 210–212 °C, mp 204–207 °C, [α]D = −115.3° (c = 0.17, CHCl3). Source: Marinederived fungus Coniothyrium cereal, terrestrial fungi Gremmeniella abietina and Roesleria hypogeal. Pharm: Antibacterial (gram-positive bacteria); antifungal (yeast); Phytotoxin. Ref: W. A. Ayer, et al, Can. J. Chem., 1986, 64, 1585│M. F. Elsebai, et al, Org. Biomol. Chem., 2011, 9, 802 O

O

HO

OH

S

O

2.14 Miscellaneous Polycyclic Aromatics 935 Arenjimycin Type: Miscellaneous polycyclic aromatics. C33H33NO14 Source: Marine-derived bacterium Salinispora arenicola from ascidian Ecteinascidia turbinata (Sweetings Cay, Grand Bahama I., Bahamas). Pharm: Cytotoxic (HCT116, potent); antibacterial (DRS, other gram-positive pathogens, Mycobacterium bacille). Ref: R. N. Asolkar, et al, J. Antibiot., 2010, 63, 37 O

OH

O O

O

H HO

O

N H

OH O

O

HO O

O

320

2 Aromatic Metabolites

936 Bryoanthrathiophene 5,7-Dihydroxy-1-methyl-6H-anthra[1,9-bc]thiophen-6-one Type: Miscellaneous polycyclic aromatics. C16H10O3S Yellow powder. Source: Bryozoan Watersipora subtorquata. Pharm: Antiangiogenic. Ref: S. -J. Jeong, et al, JNP, 2002, 65, 1344 OH

O

OH

S

937 Citreaglycon A Type: Miscellaneous polycyclic aromatics. C27H20O11 Source: Marine-derived streptomycete Streptomyces caelestis (seawater, Jiddah, Saudi Arabia). Pharm: Antibacterial (Staphylococcus haemolyticus UST950701-004, MIC = 8.0 μg/mL, control Penicillin G, MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Staphylococcus aureus UST950701-005, MIC = 16.0 μg/mL, Penicillin G, MIC = 0.25 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Bacillus subtilis 769, MIC = 8.0 μg/mL, Penicillin G, MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; MRSA ATCC43300, MIC = 8.0 μg/mL, Penicillin G, MIC > 50 μg/mL, Streptomycin, MIC > 50 μg/mL); cytotoxic (HeLa, IC50 > 40 μg/mL, control Cisplatin, IC50 = 18.14 μg/mL). Ref: L. -L. Liu, et al, Mar. Drugs, 2012, 10, 2571 O

O

O OH OH

O

OH

O OH

O OH

938 Citreamicin θA Type: Miscellaneous polycyclic aromatics. C30H25NO11 Source: Marine-derived streptomycete Streptomyces caelestis (seawater, Jiddah, Saudi Arabia). Pharm: Antibacterial (Staphylococcus haemolyticus UST950701-004, MIC = 0.5 μg/mL, control Penicillin G, MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Staphylococcus aureus UST950701-005, MIC = 1.0 μg/mL, Penicillin G, MIC = 0.25 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Bacillus subtilis 769, MIC = 0.25 μg/mL, Penicillin G, MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Staphylococcus aureus (MRSA) ATCC43300, MIC = 0.25 μg/mL, Penicillin G, MIC > 50 μg/mL, Streptomycin,

2.14 Miscellaneous Polycyclic Aromatics

321

MIC > 50 μg/mL); cytotoxic (HeLa, IC50 = 0.055 μg/mL, control Cisplatin, IC50 = 18.14 μg/mL). Ref: L. -L. Liu, et al, Mar. Drugs, 2012, 10, 2571 O OH

O N O OH O

HO

O OH

O

OH

939 Citreamicin θB Type: Miscellaneous polycyclic aromatics. C30H25NO11 Source: Marine-derived streptomycete Streptomyces caelestis (seawater, Jiddah, Saudi Arabia). Pharm: Antibacterial (Staphylococcus haemolyticus UST950701-004, MIC = 0.5 μg/mL, control Penicillin G, MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Staphylococcus aureus UST950701-005, MIC = 1.0 μg/mL, Penicillin G, MIC = 0.25 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Bacillus subtilis 769, MIC = 0.25 μg/mL, Penicillin G, MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Staphylococcus aureus (MRSA) ATCC43300, MIC = 0.25 μg/mL, Penicillin G, MIC > 50 μg/mL, Streptomycin, MIC > 50 μg/mL); cytotoxic (HeLa, IC50 = 0.072 μg/mL, control Cisplatin, IC50 = 18.14 μg/mL). Ref: L. -L. Liu, et al, Mar. Drugs, 2012, 10, 2571 O OH

O N O OH O

HO

O OH

O

OH

940 Dehydrocitreaglycon A Type: Miscellaneous polycyclic aromatics. C27H20O10 Source: Marine-derived streptomycete Streptomyces caelestis (seawater, Jiddah, Saudi Arabia). Pharm: Antibacterial (Staphylococcus haemolyticus UST950701-004, MIC = 8.0 μg/mL, control Penicillin G,

322

2 Aromatic Metabolites

MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Staphylococcus aureus UST950701-005, MIC = 16.0 μg/mL, Penicillin G, MIC = 0.25 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Bacillus subtilis 769, MIC = 8.0 μg/mL, Penicillin G, MIC = 0.13 μg/mL, Streptomycin, MIC = 8.0 μg/mL; Staphylococcus aureus (MRSA) ATCC43300, MIC > 50 μg/mL, Penicillin G, MIC > 50 μg/mL, Streptomycin, MIC > 50 μg/mL); cytotoxic (HeLa, IC50 > 40 μg/mL, control Cisplatin, IC50 = 18.14 μg/mL). Ref: L. -L. Liu, et al, Mar. Drugs, 2012, 10, 2571 O

O

O OH OH

O

OH

O OH

O

941 5,7-Dihydroxy-1-(hydroxymethyl)-6H-anthra[1,9-bc]thiophen-6-one Type: Miscellaneous polycyclic aromatics. C16H10O4S mp > 260 °C. Source: Bryozoan Dakaria subovoidea (Japan waters). Pharm: Antioxidant; hypolipemic. Ref: T. Shindo, et al, Experientia, 1993, 49, 177 OH

O

HO

OH

S

942 5,7-Dihydroxy-6-oxo-6H-anthra[1,9-bc]thiophene-1-carboxylic acid, methyl ester Type: Miscellaneous polycyclic aromatics. C17H10O5S mp 230–235 °C. Source: Bryozoan Dakaria subovoidea (Japan waters). Pharm: Antioxidant; hypolipemic. Ref: T. Shindo, et al, Experientia, 1993, 49, 177│T. R. Kelly, et al, Org. Lett., 2000, 2, 2351-2352 O O

OH

S

O

OH

2.14 Miscellaneous Polycyclic Aromatics

323

943 1-Hydroxy-1-norresistomycin 1,3,5,7,10-Pentahydroxy-1,9-dimethyl-2H-benzo[cd]pyrene-2,6(1H)-dione Type: Miscellaneous polycyclic aromatics. C21H14O7 Orange solid. Source: Marine-derived streptomycete Streptomyces chibaensis AUBN1/7. Pharm: Cytotoxic (gastric adenocarcinoma HM02 and hmn liver cancer HepG2 cells); antibacterial (gram-positive and -negative bacteria). Ref: A. Gorajana, et al, J. Antibiot., 2005, 58, 526│I. Kock, et al, J. Antibiot., 2005, 58, 530 OH HO

O OH

OH

O

OH

944 Kiamycin Type: Miscellaneous polycyclic aromatics. C20H18O4 Source: Marine-derived streptomycete Streptomyces sp. M268 (sediment, Qingdao, China). Pharm: Cytotoxic (100 μmol/L: HL60, InRt = 68.8%, control Adriamycin, InRt = 70.0%; Bel7402, InRt = 31.7%, Adriamycin, InRt = 79.3%; A549, InRt = 55.9%, Adriamycin, InRt = 80.8%). Ref: Z. Xie, et al, Mar. Drugs, 2012, 10, 551 O

H OH O

OH

945 (–)-Lomaiviticin A Type: Miscellaneous polycyclic aromatics. C68H80N6O24 Amorph. red powder, [α]D = −101.4° (c = 0.07, MeOH). Source: Marine-derived bacterium Micromonospora lomaivitiensis LL-37I366. Pharm: Cytotoxic (biochemical induction assay, potent DNA damaging agent with minimum induction concentration ≤ 0.1 ng/spot); cytotoxic (24 cancer cell line panel, cytotoxicity profile was compared to known DNA-damaging anticancer drugs adriamycin and mitomicin C, suggesting different mechanism of interaction with DNA molecules); cytotoxic (potent: K562, IC50 = 11 nmol/L, LNCaP, IC50 = 2 nmol/L, HCT116, IC50 = 2 nmol/L, HeLa, IC50 = 7 nmol/L);cytotoxic (number of cancer cell lines, IC50 = 0.01–98 ng/mL); antibacterial (plate assay, gram-positive bacteria, MIC = 6–25 ng/spot). Ref: H. He, et al, JACS, 2001, 123, 5362│C. M. Woo, et al, JACS, 2012, 134, 15285

324

2 Aromatic Metabolites

OH O

O

O O OH OH

N O

O

N2

O H

OH

O

O

OH

O

OH

H OH O O O

O

O

N2

OH

O N

946 Lomaiviticin B Type: Miscellaneous polycyclic aromatics. C54H56N6O18 Amorph. red powder, [α]D = −71.4° (c = 0.07, MeOH). Source: Marine-derived bacterium Micromonospora lomaivitiensis LL-37I366. Pharm: Cytotoxic (biochemical induction assay, potent DNA damaging agent with minimum induction concentration ≤ 0.1 ng/spot); cytotoxic (24 cancer cell line panel, cytotoxicity profile was compared to known DNA-damaging anticancer drugs adriamycin and mitomicin C, suggesting different mechanism of interaction with DNA molecules); antibacterial (plate assay, gram-positive bacteria, MIC = 6–25 ng/spot). Ref: H. He, et al, JACS, 2001, 123, 5362│C. M. Woo, et al, JACS, 2012, 134, 15285

O

O OH

OH

O

N N2 O H

OH

O

HO

OH

O

OH

O

OH

H O

O O OH N

N2

2.14 Miscellaneous Polycyclic Aromatics

325

947 (–)-Lomaiviticin C Type: Miscellaneous polycyclic aromatics. C68H82N4O24 Source: Marine-derived bacterium Salinispora pacifica (USDA Agricultural Research Service). Pharm: Cytotoxic (K562, IC50 = 472 nmol/L, LNCaP, IC50 = 332 nmol/L, HCT116, IC50 = 223 nmol/L, HeLa, IC50 = 589 nmol/L). Ref: C. M. Woo, et al, JACS, 2012, 134, 15285 O N OH

O HO

O

H

O

O

O

O

O H

HO

OH

H O

O

O

OH O OH

N2

O

HO

O O HO N

948 (–)-Lomaiviticin D Type: Miscellaneous polycyclic aromatics. C69H84N4O24 Source: Marine-derived bacterium Salinispora pacifica (USDA Agricultural Research Service). Pharm: Cytotoxic (K562, IC50 = 197 nmol/L, LNCaP, IC50 = 196 nmol/L, HCT116, IC50 = 167 nmol/L, HeLa, IC50 = 161 nmol/L). Ref: C. M. Woo, et al, JACS, 2012, 134, 15285 O N

and R1=H, R2=Me

O

O

H HO

O

R2

HO O

O

O

O

O H

HO O OH

OH

H O

O O

OH

R1 and R1=H, R2=Me

N2

O O

O O HO N

326

2 Aromatic Metabolites

949 (–)-Lomaiviticin E Type: Miscellaneous polycyclic aromatics. C70H86N4O24 Source: Marine-derived bacterium Salinispora pacifica (USDA Agricultural Research Service). Pharm: Cytotoxic (K562, IC50 = 496 nmol/L, LNCaP, IC50 = 964 nmol/L, HCT116, IC50 = 255 nmol/L, HeLa, IC50 = 292 nmol/L). Ref: C. M. Woo, et al, JACS, 2012, 134, 15285 O N

O

O HO

O

HO

O

O O

O

O H

HO

OH

O

O

O

OH

OH

H

O

N2

O O

O O

HO N

950 Talaromycesone A Type: Miscellaneous polycyclic aromatics. C28H24O11 Source: Marine fungus Talaromyces sp. LF458. Pharm: Antibacterial (hmn pathogenic Staphylococcus epidermidis, IC50 = 3.70 μmol/L; MRSA, IC50 = 5.48 μmol/L); acetylcholinesterase inhibitor. Ref: B. Wu, et al, Mar. Biotechnol., 2015, 17, 110 O

OH

O HO O H O O

O O H

O HO

951 Talaromycesone B Type: Miscellaneous polycyclic aromatics. C27H18O10 Source: Marine fungus Talaromyces sp. LF458. Pharm: Antibacterial (hmn pathogenic Staphylococcus

2.14 Miscellaneous Polycyclic Aromatics

327

epidermidis, IC50 = 17.36 μmol/L; MRSA, IC50 = 19.50 μmol/L); acetylcholinesterase inhibitor. Ref: B. Wu, et al, Mar. Biotechnol., 2015, 17, 110 O

OH

O

O HO O O O

H

O HO

Index 1 Compound Name and Synonym Index This index lists in alphabetical order all active compound’s 1,084 entry names including both 951 key names and 133 synonym names contained in the bodies of compound entries. A equal sign (=) and compound code number (from 1 to 951) follow the name immediately for locating the compound in the “Handbook of Active Marine Natural Products Volume 7” book. Following symbols are ineffective in ordering: D-, L-, dl, R-, S-, E-, Z-, O-, N-, C-, H-, cis-, trans-, ent-, epi-, meso-, erythro-, threo-, sec-, seco-§, m-, o-, p-, n-, α-, β-, γ-, δ-, ε-, κ-, ξ-, ψ-, ω-, (+), (−), (±) etc., and: 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, {,}, [,], (,),,,;,, *, ‘, ‘‘, ‘‘‘, →, etc. (§note: In the books regular “seco-” is effective in ordering as “nor-”.) A Abietinarin A = 861. Abietinarin B = 862. Accinal A = 772. (±)-Acetophthalidin = 632. 3-(2-Acetoxy-4,8-dimethyl-3,7-nonadienyl) benzaldehyde = 300. Acetoxyfimbrolide A = 18. Acetoxyfimbrolide B = 19. Acetoxyfimbrolide D = 20. Acetylbenzoyl = 308. 3-Acetyl-5,7-dihydroxy-1(3H)isobenzofuranone = 632. 3-Acetyl-7-hydroxy-5-methoxy-3,4-dimethyl-1 (3H)-isobenzofuranone = 633. 7-O-Acetylsecopeni-cillide C = 480. Acetylsumiki’s acid = 4. Acremonin A = 271. Acremonin A 5-β-glucopyranoside = 272. Actinoflavoside = 765. (+)-Aeroplysinin 1 = 331. Aflatoxin B2b = 650. AGI-B4 = 425. Albidopyrone = 90. Albopunctatone = 881. Alterporriol K = 882. Alterporriol L = 883. Alterporriol P = 884. Alterporriol Q = 885. Ambigol A = 481. Ambigol B = 482. Ambigol C = 483. Amicoumacin A = 744. Amicoumacin B = 745. Amicoumacin C = 746. Ammonificin C = 651. Ammonificin D = 652.

https://doi.org/10.1515/9783110655810-003

Anhydroexfoliamycin = 850. Anhydrofulvic acid = 681. Anhydrofusarubin = 851. Annulin A = 826. Annulin B = 827. Annulin C = 828. Anomalin A = 401. Anthracene derivative 100 = 863. Antibiotic 2240A = 887. Antibiotic A 80915A = 841. Antibiotic A 80915C = 842. Antibiotic AGI-B4 = 402. Antibiotic AI 77F = 747. Antibiotic BE 43472A = 886. Antibiotic CB 104 = 624. Antibiotic DC 45A = 873. Antibiotic DC 45B1 = 874. Antibiotic DC 45B2 = 875. Antibiotic F 12517 = 256. Antibiotic GS 1302-3 = 784. Antibiotic H 668 = 221. Antibiotic LL-Z 1276 = 151. Antibiotic MC 142 = 461. Antibiotic MKN 003C = 21. Antibiotic MS 347B = 447. Antibiotic NPI 0047 = 2. Antibiotic NPI 0052 = 1. Antibiotic PM94128 = 748. Antibiotic SB236049 = 653. Antibiotic SB236050 = 682. Antibiotic SB238569 = 683. Antibiotic SC 2051 = 803. Antibiotic Sg17-1-4 = 749. Antibiotic SM 173A = 923. Antibiotic TUF 95F47 = 783. Aplysillin A = 564. Aplysiopsene C = 170.

330

Index 1 Compound Name and Synonym Index

Apralactone A = 654. Aquastatin A = 453. Aranciamycin = 923. Arenjimycin = 935. Arugosin A = 454. Arugosin B = 455. Arugosin H = 386. Ascochital = 320. Ascochitin = 687. Ascochytatin = 222. Ascolactone B = 634. Asnipyrone A = 91. Asnipyrone B = 92. Asperbiphenyl = 688. Asperflavin 6-O-α-D-Ribofuranoside = 864. Aspergillitine = 655. Aspergillumarin A = 750. Aspergillumarin B = 751. Aspergillusene A = 345. Aspergillusone B = 403. Aspergilone A = 689. Aspergiolide A = 925. Aspergiolide B = 926. Aspergione B = 742. Asperlactone = 22. Aspernolide A = 23. Aspernolide B = 24. Asperpyrone A = 804. Asperpyrone C = 805. Aspiketolactonol = 25. Aspilactonol A = 26. Aspilactonol B = 27. Aspilactonol C = 28. Aspilactonol D = 29. Aspilactonol E = 30. Aspilactonol F = 31. Aspulvinone E = 582. Aspyrone = 93. Aspyronol = 94. Attenol A = 223. Aurasperone A = 806. Aurasperone B = 807. Aurasperone E = 814. Auripyrone A = 172. Auripyrone B = 173. 7-epi-Austdiol = 690. Austrocortinin = 891. Austrocortirubin = 876. Avrainvilleol = 376.

Awajanoran = 484. Ayamycin = 360. Azaspirofuran A = 224. B Bacillisporin A = 823. Bacillisporin C = 824. Bacillosporin A = 823. Bacillosporin C = 824. Bacillosporin D‡ = 825. Bacilosarcin B = 752. Balticol A = 773. Balticol B = 774. Balticol C = 775. Balticol D = 776. Balticol E = 777. Balticol F = 778. BDDE = 285. 1,2-Benzenedicarboxylic acid2,12-Diethyl11-methylhexadecyl 2-ethyl-11methylhexadecyl ester = 321. 1,2-Benzenedicarboxylic acid2-Ethyldecyl 2-ethylundecyl ester = 322. 2-Benzyl-5-hydroxy-6,8-dimethoxy-4H-benzo[g] chromen-4-one = 796. 6-Benzyl-4-oxo-4H-pyran-3-carboxamide = 175. Bicoumanigrin = 685. 6,6ʹ-Bieckol = 544. 8,8ʹ-Bieckol = 544. 4ʹʹʹ-O-7-Bieckol = 547. 7,7ʹ-Bihelminthosporin = 887. 2,2ʹ-Bihelminthosporin = 887. Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether = 285. Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether = 286. Bis(2-ethyldodecyl) phthalate = 323. (Z,Z)-3,3′-Bis-3-[(4-hydroxy-2-methoxyphenyl)2-propenamide] = 539. Bissetone = 174. Bistramide A = 225. Bistramide B = 226. Bistramide C = 227. Bistramide D = 228. Bistramide K = 229. Bistratene A = 225. Bistratene B = 230. Bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether = 287.

Index 1 Compound Name and Synonym Index

1,2-Bis(2,3,6-tribromo-4,5-dihydroxyphenyl) ethane = 565. Bitungolide A = 95. Bitungolide B = 96. Bitungolide C = 97. Bitungolide D = 98. Bitungolide E = 99. Bitungolide F = 100. Bostrycin = 877. 4-Bromobeckerelide = 32. 3-Bromo-4,5-bis(2,3-dibromo4,5-dihydroxybenzyl)pyrocatechol = 377. 2-Bromo-5-[4-(4-bromo-2-hydroxy-5methoxyphenyl)-2-butenyl]-1,3-benzenediole = 567. 3-Bromo-5-[4-(3-bromo-4-hydroxyphenyl)2,3-bis(sulfoxy)-1,3-butadienyl]1,2-benzenediol = 564. Bromochlorogentisylquinone A = 361. Bromochlorogentisylquinone B = 362. 5-Bromo-4,7-dihydroxy-1-indanone = 858. Bromol = 266. 2-(5-Bromo-2-methoxy-phenoxy)3,5-dibromophenol = 485. Bromomethylchlamydosporol A = 101. Bromomethylchlamydosporol B = 102. Bryoanthrathiophene = 936. BST-A = 225. BST-B = 226. BST-C = 227. BST-D = 228. Butyl-isobutylphthalate = 324. 3-Butyl-7-methoxyphthalide = 635. (+)-Butyrolactone I = 33. (+)-Butyrolactone II = 34. (+)-Butyrolactone III = 35. (–)-Byssochlamic acid = 171. C Cadiolide B = 583. Cadiolide E = 584. Cadiolide G = 585. (5E)-Cadiolide H = 586. (5Z)-Cadiolide H = 587. Cadiolide I = 588. Caffeoylate ester = 656. Callystatin A = 103. Carbamidocyclophane A = 604.

331

Carbamidocyclophane B = 605. Carbamidocyclophane C = 606. Carbamidocyclophane D = 607. Carbamidocyclophane E = 608. Carbonarone A = 175. Carbonarone B = 176. 8-Carboxy-isoiantheran A = 566. 8-Carboxy-isoiantheran A = 569. 5-Carboxymellein = 753. Caulerprenylol A = 346. Caulerprenylol B = 347. (–)-Cereoaldomine = 789. (–)-Cereolactam = 790. Chaetocyclinone A = 684. Chaetomugilin A = 709. 4′-epi-Chaetomugilin A = 710. 11-epi-Chaetomugilin A = 711. Chaetomugilin B = 712. Chaetomugilin C = 713. Chaetomugilin D = 714. Chaetomugilin E = 715. Chaetomugilin F = 716. Chaetomugilin G = 717. Chaetomugilin H = 718. Chaetomugilin I = 719. 11-epi-Chaetomugilin I = 720. Chaetomugilin J = 721. Chaetomugilin K = 722. Chaetomugilin L = 723. Chaetomugilin N = 724. Chaetomugilin O = 725. Chaetomugilin P = 726. Chaetomugilin Q = 727. Chaetomugilin R = 728. Chaetomugilin S = 729. Chaetopyranin = 301. Chaetoquadrin F = 104. Chaetoxanthone A = 404. Chaetoxanthone B = 405. Chaetoxanthone C = 406. Chlamydosporol = 105. 3-Chloro-4,5-dihydroxybenzyl alcohol = 288. Chlorogentisyl alcohol = 289. Chlorogentisylquinone = 363. Chlorohydroaspyrone A = 106. Chlorohydroaspyrone B = 107. 9-Chloro-8-hydroxy-8,9-deoxyasperlactone = 36. 8-Chloro-9-hydroxy-8,9-deoxyasperlactone = 37.

332

Index 1 Compound Name and Synonym Index

9-Chloro-8-hydroxy-8,9-deoxyaspyrone = 108. 2-Chloro-6-(hydroxymethyl)1,4-benzenediol = 289. 2-Chloro-6-(methoxymethyl)1,4-benzenediol = 290. Chromanone = 177. Chromanone A = 657. Chromenol = 658. Chrysophaentin A = 486. Chrysophaentin E = 487. Chrysophaentin F = 488. Chrysophanol = 888. Cillifuranone = 38. Citreaglycon A = 937. Citreamicin θA = 938. Citreamicin θB = 939. Citreopyrone = 156. Citrinin = 691. Citrinin H2 = 267. Coenzyme Q9 = 364. Coibacin A = 109. Coibacin B = 110. Coibacin C = 111. Coibacin D = 112. Colpol = 567. Comazaphilone A = 730. Comazaphilone B = 731. Comazaphilone C = 732. Comazaphilone D = 733. Comazaphilone E = 734. Comazaphilone F = 735. Communol A = 309. Communol F = 310. Communol G = 311. Comosone A = 273. Comosusol A = 274. Comosusol B = 275. Comosusol C = 276. Comosusol D = 277. Coniolactone = 779. Conioscleroderolide = 927. (E)-Coniosclerodinol = 928. (Z)-Coniosclerodinol = 929. Coniosclerodione = 933. Cordyol C = 489. Cordyol Cʹ = 490. Cordyol E = 491. Corollosporin = 636. Corynesidone A = 456.

Crispatene = 178. Crispatone = 179. Crossbyanol B = 545. 9(13)-Cyclodiscodermolide = 113. Cyercene 1 = 114. Cyercene 2 = 115. Cyercene 3 = 116. Cyercene 4 = 117. Cyercene 5 = 118. Cyercene A = 180. Cyercene B = 181. Cylindrocarpol = 302. Cylindrocyclophane A = 609. Cylindrocyclophane A1 = 610. Cylindrocyclophane A2 = 611. Cylindrocyclophane A3 = 612. Cylindrocyclophane A4 = 613. Cylindrocyclophane AB4 = 614. Cylindrocyclophane C = 615. Cylindrocyclophane C2 = 616. Cylindrocyclophane C4 = 617. Cylindrocyclophane F = 618. Cylindrocyclophane F4 = 619. Cymobarbatol = 398. Cytosporone B = 312. Cytosporone C = 692. Cytosporone E = 637. D Dantron = 889. 12-O-Deacetyl-phomoxanthone A = 407. Deacetylphomoxanthone B = 408. Deacetyl-phomoxanthone C = 409. 19-Deaminocarbonyldiscodermolide = 119. Debromoisocymobarbatol = 399. Debromomarinone = 829. Debromomethoxymarinone = 830. Decarboxyhydroxycitrinone = 754. 4a-Dechloroantibiotic A 80915C = 843. 4a-Dechloro-4,4a-didehydro-antibiotic A 80915A = 844. Dehydrocitreaglycon A = 940. 9-Dehydroxyeurotinone = 457. 9-Dehydroxyeurotinone = 458. 8,9-Dehydroxylarone = 120. 2-Demethyldiscodermolide = 121. 8ʹ-O-Demethylisonigerone = 808. 8-O-Demethylnigerone = 809. 8ʹ-O-Demethylnigerone = 809.

Index 1 Compound Name and Synonym Index

6-Demethylsorbicillin = 313. 5,7-Dideoxybostrycin = 878. 5-Deoxybostrycin = 879. 3ʹʹ-Deoxy-6ʹ-O-desmethylcandidusin B = 573. Deoxyfusapyrone = 182. 4ʹʹ-Deoxyisoterprenin = 574. Deoxylapachol = 831. 4ʹʹ-Deoxyprenylterphenyllin = 575. 1-Deoxyrubralactone = 755. 4ʹʹ-Deoxyterprenin = 576. 1-Deoxytetrahydrobostrycin = 867. 6-Desmethoxyhormothamnione = 693. 6ʹ-O-Desmethylterphenyllin = 577. Desmethylubiquinone Q2 = 367. Dianhydroaurasperone C = 810. Diaporthelactone = 638. Dibenzo [1,4]dioxine-2,4,7, 9-tetraol = 546. 4,5-Dibromo-1,3-benzenediol = 268. 5,6-Dibromocatechol = 268. 2,3-Dibromo-5-chloro-6-(2,4-dibromophenoxy) phenol = 492. 2,4-Dibromo-6-chlorophenol = 260. 3,5-Dibromo-1-cyanomethyl-4-methoxy3,5-cyclohexadiene-1,2-diol = 331. 3,5-Dibromo-2-(2,4-dibromophenoxy)4-methoxyphenol = 493. 2,3-Dibromo-4,5-dihydroxybenzyl alcohol = 291. 4,6-Dibromo-homogentisic acid methyl ester = 338. 4,6-Dibromo-2-(2ʹ-methoxy-4ʹ,6ʹdibromophenoxy)phenol = 494. 2-(3,5-Dibromo-2-methoxy-phenoxy)3-bromophenol = 495. 2-(4,6-Dibromo-2-methoxy-phenoxy)3,5-dibromophenol = 496. 2-(3,5-Dibromo-2-methoxy-phenoxy)3,4,5-tribromoanisole = 497. 2,6-Dibromophenol = 261. 2,4-Dibromophenol = 262. 2,4-Dibromophenol = 263. 2-(2,4-Dibromo-phenoxy)3,4,5-tribromophenol = 498. 3,5-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹhydroxyphenoxy) phenol = 499. 4,6-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹhydroxyphenoxy) phenol = 500.

333

4,6-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo2ʹ-hydroxyphenoxy) phenol1-methylether = 501. Dicerandrol A = 410. Dicerandrol B = 411. Dicerandrol C = 412. (±)-Dictyochromenol = 659. Didemnaketal A = 231. Didemnaketal B = 232. Dieckol = 547. Diemenensin A = 122. Diemenensin B = 123. Dihydroanhydrojavanicin = 791. Dihydroaspyrone = 124. 4,5-Dihydro-2,4-dimethyl-3furancarboxaldehyde = 5. Dihydro-3 (2H)-furanone = 10. (2R)-2,3-Dihydro-7-hydroxy-6,8-dimethyl2-[(E)-prop-l-enyl]chromen-4-one = 660. 2,3-Dihydro-2-hydroxy-2,4-dimethyl-5-transpropenylfuran-3-one = 6. 2,3-Dihydro-5-hydroxy-8-methoxy-2,4dimethylnaphtho[1,2-b]furan-6,9dione = 791. 6,7-Dihydro-3-(hydroxymethyl)-6-methyl4(5H)-benzofuranone = 626. 6,9-Dihydro-7-hydroxy-7-methyl-2-(1methylethylidene)-7H-furo[3,2-h][2] benzopyran-3(2H)-one = 743. 2,3-Dihydro-7-hydroxy-6-methyl-2-(1-propenyl)4H-1-benzopyran-4-one = 661. 3′,4′-Dihydroinfectopyrone = 125. 2,3-Dihydro-1-methoxy-6-methyl-3-oxo-1Hindene-4-carboxaldehyde = 859. 3,4-Dihydro-3,4,6,8-tetrahydroxy-3-methyl-1H2-benzopyran-1-one = 756. 3,4-Dihydro-3,4,8-trihydroxy3-(2-hydroxypropyl)-6-methoxy-1(2H)naphthalenone = 777. 1,8-Dihydroxyanthraquinone = 889. 3,4-Dihydroxybenzoic acid = 325. 2,5-Dihydroxybenzyl alcohol = 292. 1,11-Dihydroxy-1,3,5,7E-bisabolatetren-15-oic acid = 348. 1,7-Dihydroxy-2,4-dimethoxy-6methylanthraquinone = 890. 3,3′-Dihydroxy-5,5′-dimethyldiphenyl ether = 505.

334

Index 1 Compound Name and Synonym Index

(2E,4E)-1-(2,6-Dihydroxy-3,5-dimethyl-phenyl) hexa-2,4-dien-1-one = 315. 5,7-Dihydroxy-1-(hydroxymethyl)-6Hanthra[1,9-bc]thiophen-6-one = 941. 1,4-Dihydroxy-2-methoxy-7methylanthraquinone = 891. 1,3-Dihydroxy-6-methoxy-8methylanthraquinone = 892. 1,8-Dihydroxy-2-methoxy-6methylanthraquinone = 909. 1,7-Dihydroxy-2-methoxy-3-(3-methylbut2-enyl)-9H-xanthen- 9-one = 413. 5,7-Dihydroxy-2-[[1-(4-methoxy-2-oxo-2H-pyran6-yl)-2-phenylethyl]amino]-1,4naphthoquinone = 126. 1,8-Dihydroxy-3-methylanthraquinone = 888. 1,4-Dihydroxy-6-methylanthraquinone = 893. 5,7-Dihydroxy-1-methyl-6H-anthra[1,9-bc] thiophen-6-one = 936. 1,7-Dihydroxy-9-methyldibenzo[b,d] furan3-carboxylic acid = 391. 1,3-Dihydroxy-6-methyl-8methoxyanthraquinone = 894. 1-(2,4-Dihydroxy-5-methylphenyl)-2,4-hexadien -1-one = 313. 1-(2,4-Dihydroxy-5-methylphenyl)-4-hexen1-one = 318. 5,7-Dihydroxy-6-oxo-6H-anthra[1,9-bc] thiophene-1-carboxylic acid, methyl ester = 942. 1-(3′,5′-Dihydroxyphenoxy)-7-(2″,4″, 6″-trihydroxyphenoxy)-2,4,9trihydroxydibenzo-1,4-dioxin = 556. (3S)-(3,5-Dihydroxyphenyl)butan-2-one = 339. 3,4-Dihydroxystyryl sulfate = 336. (3R,4S)-6,8-Dihydroxy-3,4,5trimethyisochroman-1-one = 757. 2,4-Dihydroxy-3,5,6-trimethylbenzaldehyde = 269. 2,6-Dimethoxy-1,4-benzoquinone = 365. 1,3-Dimethoxy-6-methylanthraquinone = 895. 6,8-Di-O-methylaverantin = 896. 2,2-Dimethyl-2H-1-benzopyran-6-ol = 662. 3,9-Dimethyldibenzo[b,d]furan-1,7-diol = 392. Dimethyl-2,3ʹ-dimethylosoate = 502. 6-(3,5-Dimethyl-1,3-hexadienyl)-4-methoxy3-methyl-2H-pyran-2-one = 116. 6-(1,3-Dimethyl-1,3-hexadienyl)-4-methoxy5-methyl-2H-pyran-2-one = 118.

Dimethyl 8-methoxy-9-oxo-9H-xanthene1,6-dicarboxylate = 414. 4-(1,3-Dimethyl-2-oxopentyl)-3-formyl2,6-dihydroxybenzoic acid = 320. 6-(1,3-Dimethyl-1,3-pentadienyl)-4-methoxy5-methyl-2H-pyran-2-one = 117. 2-(1,1-Dimethyl-2-propenyl)-5-(3-methyl2-butenyl)-1,4-benzoquinone = 366. 4-(1,1-Dimethyl-2-propenyl)-2-(3-methyl2-butenyl)phenol = 264. Diorcinol = 503. Diorcinol = 504. Diorcinol = 505. Diorcinol D = 506. Diorcinol E = 507. Dioxamycin = 897. Dioxinodehydroeckol = 548. Diphlorethohydroxycarmalol = 549. 2,4-Diprenylphenol = 265. Discodermolide = 127. 2-epi-Discodermolide = 128. Disermolide = 127. Dothiorelone D = 694. DPHC = 549. E Echinofuran‡. = 7. Eckol = 550. Emerixanthone A = 415. Emerixanthone C = 416. Emerixanthone D = 417. Emodin = 898. Engyodontiumone B = 418. Engyodontiumone C = 419. Engyodontiumone D = 420. (±)-Engyodontiumone E = 421. (±)-Engyodontiumone F = 422. (±)-Engyodontiumone G = 423. Engyodontiumone H = 424. (2β)-Engyodontiumone H = 425. Engyodontiumone I = 348. Epicoccone = 639. 8,12-Epoxy-1 (10),4 (15),7,11-guaiatetraene = 7. Esculetin-4-carboxylic acid ethyl ester = 686. Ethyl 3,5-dibromo-4(3ʹN,Ndimethylaminopropyloxy)cinnamate = 340. Ethyl 5-ethoxy-2-formyl-3-hydroxy4-methylbenzoate = 314.

Index 1 Compound Name and Synonym Index

Ethyl 2-(3-hydroxy-2-(7-hydroxyoctanoyl)5-methoxyphenyl) acetate = 316. Eurorubrin = 865. Eutypoid B = 39. Eutypoid C = 40. Eutypoid D = 41. Eutypoid E = 42. Evariquinone = 899. Excoecariphenol D = 769. F Felinone B = 627. N-trans-Feruloyl-3,5-dimethoxytyramine = 342. Fijiensin = 219. Fijiolide A = 341. Flavalactone 1 = 43. Flavalactone 2 = 44. Flavalactone 3 = 45. Flavasperone = 802. Flavipesin A = 46. Flavoglaucin = 303. Fonsecin = 797. Fonsecinone A = 811. Fonsecinone B = 812. Fonsecinone C = 813. Fonsecinone D = 814. 5-Formyl-6-hydroxy-2-(3-hydroxy-1-butenyl)7-prenylchroman = 301. 7-Formyl-3-methoxy-5-methyl1-indanone = 859. p-Formylphenol = 304. Fradimycin A = 900. Fradimycin B = 901. Fucodiphlorethol G = 551. Fucofuroeckol A = 552. Fusapyrone = 183. Fusaquinone B = 866. Fusaquinone C = 867. Fusaranthraquinone = 868. Fusarnaphthoquinone A = 832. Fusarnaphthoquinone B = 833. Fusarubin = 852. G Galvaquinone B = 902. Genistein = 767. Gentisyl alcohol = 292. Geroquinol = 278. Glabruquinone A = 367.

335

globosuxanthone A = 426. Grisephenone A = 427. Griseusin C = 834. Guisinol = 459. Gymnastatin A = 233. Gymnastatin B = 234. Gymnastatin C = 235. Gymnastatin D = 236. Gymnastatin E = 237. Gymnastatin I = 238. Gymnastatin J = 239. Gymnastatin K = 240. H Halawanone A = 853. Halawanone B = 854. Halawanone C = 903. Halawanone D = 904. Harzialactone A = 47. Harzialactone B = 129. Helicascolide C = 130. 2-(1-Heptenyl)-2,3,4,6,7,8-hexahydro6-hydroxy-5H-1-benzopyran-5-one = 677. (E)-6-(1-Heptenyl)-2H-pyran-2-one = 131. 1-Heptyl-1,4-dihydro-6,8-dihydroxy-3H-2benzopyran-3-one = 692. 2,3,3′,4,5,5′-Hexabromo-2′,6-dihydroxydiphenyl ether = 508. 1,2,3,4,4a,9a-Hexahydro-1,3,4,8-tetrahydroxy4a,6-dimethyl-9H-xanthen-9-one = 433. 1,2,3,4,4a,9a-Hexahydro-1,4,8-trihydroxy3,4a-dimethyl-9H-xanthen-9-one = 434. Hexahydroxyphenoxydibenzo[1,4]dioxine = 550. 4-[2-(1-Hexenyl)-4-methylphenyl]-3-butenoic acid = 350. 3-Hexyl-3,7-dihydroxy-1(3H)-isobenzofuranone = 636. Hibiscusamide = 342. Hiburipyranone = 758. Himeic acid A = 184. Honaucin A = 48. Hormothamnione = 695. Hyalopyrone = 185. p-Hydroxybenzaldehyde = 304. 4-Hydroxybenzoic acid = 326. 5-[(2S,3R)-3-Hydroxybutan-2-yl]-4methylbenzene-1,3-diol = 343. 2-Hydroxy-2,4,6-cycloheptatrien-1-one = 625. Hydroxydebromomarinone = 835.

336

Index 1 Compound Name and Synonym Index

(2S,3S,5R)-5-[(1R)-1-Hydroxydec-9-enyl]2-pentyltetrahydrofuran-3-ol = 8. (2S,3S,5S)-5-[(1S)-1-Hydroxydec-9-enyl]2-pentyltetrahydrofuran-3-ol = 9. 3-Hydroxy-6ʹ-O-desmethylterphenyllin = 578. 9α-Hydroxydihydrodesoxybostrycin = 869. 1-Hydroxy-2,4-dimethoxy-7methylanthraquinone = 905. 1-Hydroxy-4,7-dimethoxy-6-(3-oxobutyl)9H-xanthen-9-one = 428. 2-(7-Hydroxy-3,7-dimethyl-2-octenyl)1,4-benzenediol = 279. 2-(3-Hydroxy-3,7-dimethyl-6-octenyl)1,4-benzenediol = 280. 2-Hydroxy-3,6-dimethyl-5-(1-oxo-4-hexenyl)1,4-benzoquinone = 368. 2-Hydroxy-3,5-dimethyl-6-(2-oxopropyl)1,4-benzoquinone = 369. 4-Hydroxy-3,5-dimethyl-6- (1,3,5,7-tetramethyl1,3-decadienyl)-2H-pyran-2-one = 122. 4-Hydroxy-3,5-dimethyl-6- (1,3,5,7-tetramethyl1-decenyl)-2H-pyran-2-one = 148. (S)-2-(2′-Hydroxyethyl)-4-methyl-γbutyrolactone = 49. 9α-Hydroxyhalorosellinia A = 870. 5-Hydroxy-4-(hydroxymethyl)-2H-pyran2-one = 132. Hydroxyjavanicin = 852. 6-Hydroxymellein = 759. (Z)-5-(Hydroxymenthyl)-2-(6′-methylhept2′-en-2′-yl)-phenol = 349. 5-Hydroxy-2-methoxy benzoic acid = 327. 4-Hydroxy-3-methoxyphenylglyoxylic acid methyl ester = 332. 1-Hydroxy-3-methylanthraquinone = 910. 3-(Hydroxymethyl)-9-methyldibenzo[b,d]furan1,7-diol = 393. 8-Hydroxy-3-methyl-9-oxo-9H-xanthene1-carboxylic acid methyl ether = 429. 6-Hydroxy-5-methylramulosin = 760. 1-Hydroxy-1-norresistomycin = 943. Hydroxypestalopyrone = 133. 4-Hydroxyphenethyl 2-(4-hydroxyphenyl) acetate = 333. 4-Hydroxyphenethyl methyl succinate = 334. 4-(3-Hydroxypropyl)-5,6-dimethoxybiphenyl -3,4ʹ-diol = 540. 6- (2-Hydroxypropyl)-3-methyl-2(1-methylpropyl)-4H-pyran-4-one = 185.

4-Hydroxy-8-thioxocyclohept[c][1,2]oxathiol-3 (8H)-one = 624. Hypochromin A = 815. Hypochromin B = 816. Hypogallicacid = 325. I Iantheran A = 568. Iantheran B = 569. Ilikonapyrone = 186. Ilimaquinone = 370. 5-epi-Ilimaquinone = 371. γ-Indomycinone = 920. δ-Indomycinone = 921. Irciniastatin A = 761. Irciniastatin B = 762. Isoacremine D = 628. Isoaspulvinone E = 50. Isoaspulvinone E = 589. Isobutyrolactone II = 51. Isochromophilone XI = 696. Isocladospolide B = 52. Isocymobarbatol = 400. Isodihydroauroglaucin = 305. Isoiantheran A = 570. Isojaspisin = 335. Isomarinone = 836. Isomonodictyphenone = 387. Isonigerone = 817. Isopectinatone = 134. Isoplacidene A = 187. Isoplacidene B = 188. Isopopopolohuanone E = 394. 7-Isopropenylbicyclo[4.2.0]octa-1,3,5-triene-2,5diol = 271. 7-Isopropenylbicyclo[4.2.0]octa1,3,5-triene-2,5-diol-5β-glucopyranoside = 272. Isorawsonol = 378. Isorhodoptilometrin-1-methyl ether = 906. Isosorbicillin = 315. J Jaspisin = 336. Javanicin tautomeric with 5,8-quinone structure = 837. JBIR 97 = 430. JBIR 98 = 431. JBIR 99 = 432.

Index 1 Compound Name and Synonym Index

K Kaempferol 7-glucoside = 766. Kalkipyrone = 189. Kandelisesquilignan A = 770. Kandelisesquilignan B = 771. Karanjapin = 768. Keisstetralone = 780. Kiamycin = 944. L Lagunapyrone B = 135. Laurencione (cyclic hemiacetal form) = 10. Lehualide B = 190. Lehualide D = 191. Lehualide E = 136. Leptosphaerodione = 857. Lissoclinolide = 53. Lithothamnin A = 509. (–)-Lomaiviticin A = 945. Lomaiviticin B = 946. (–)-Lomaiviticin C = 947. (–)-Lomaiviticin D = 948. (–)-Lomaiviticin E = 949. Longithorone A = 372. Lorneic acid A = 350. Lorneic acid B = 351. M (–)-Malyngolide = 137. Malyngolide dimer = 138. Marfuraquinocin A = 792. Marfuraquinocin C = 793. Marfuraquinocin D = 794. Marilone A = 640. Marilone B = 641. Marilone C = 642. Marinactinone B = 192. Marinactinone C = 193. Marinisporolide A = 241. Marinone = 838. Maurapyrone A = 194. Maurapyrone C = 195. Maurapyrone D = 196. Mediterraneol A = 281. Methoxydebromomarinone = 830. (4R*,5R*,9S*,10R*,11Z)-4-Methoxy-9((dimethylamino)-methyl)-12,15-epoxy-11 (13)-en-decahydronaphthalen-16-ol = 781.

337

2-(Methoxymethyl)-1,4-benzenediol = 282. 1-Methoxy-3-methyl-8-hydroxyanthraquinone = 907. (2′S)-4-Methoxy-3-(2′-methyl-3′-hydroxy) propionyl-methyl benzoate = 328. 4-Methoxy-3-methyl-6-(3-methyl-1,3hexadienyl-)2H-pyran-2-one = 115. 4-Methoxy-3-methyl-6-(3-methyl-1,3pentadienyl)-2H-pyran2-one = 114. 5ʹ-Methoxyvermistatin = 197. 2-O-Methyl-4-O-(a-D-ribofuranosyl)-9deoxyeurotinone = 460. 8-O-Methyl-epi-austdiol = 697. 7-Methylcyercene 1 = 139. 3ʹ-O-Methyldehydroisopenicillide = 461. 2-O-Methyl-9-deoxyeurotinone = 462. 3-O-Methyldiorcinol = 491. 5-O-Methyldothiorelone A = 316. 5,5ʹ-Methylenebisasperflavin = 865. 3-O-Methylfusarubin = 855. Methyl 4-hydroxy-3-(3-methylbut-2-enyloxy) benzoate = 329. Methyl 4-hydroxyphenylacetate = 337. (–)-5-Methylmellein = 763. 6-O-Methylnorrubrofusarin = 800. 30-Methyloscillatoxin D = 242. Methyl phenyl diketone = 308. 2-Methyl-2-(prenylmethyl)-2H-1-benzopyran6-ol = 658. 6-Methylquinizarin = 893. O-Methylspongiadioxin A = 510. O-Methylspongiadioxin B = 511. O-Methylspongiadioxin C = 512. Microsphaerol = 513. MK844-mF10 = 908. Monascidin A = 691. Monodictyochrome A = 663. Monodictyochrome B = 664. Monodictyphenone = 388. Monodictyquinone = 909. Monodictysin A = 433. Monodictysin B = 434. Monodictysin C = 435. Monodictyxanthone = 436. Mutafuran H = 11. Mycalamide C = 83. Mycophenolic acid = 643.

338

Index 1 Compound Name and Synonym Index

N Nakitriol = 352. Napyradiomycin A = 845. Napyradiomycin B = 846. Napyradiomycin D = 847. Napyradiomycin E = 848. Napyradiomycin F = 849. Nectriapyrone A = 140. Neofusapyrone = 141. Neomarinone = 839. Neurymenolide A = 142. Neurymenolide B = 143. NG 261 = 52. Nigerapyrone B = 144. Nigerapyrone D = 145. Nigerapyrone E = 146. Nigerasperone A = 798. Nigerasperone B = 818. Nigerasperone C = 819. Nigerone = 820. Nigrosporapyrone A = 147. Nigrosporin B = 880. Nodulisporacid A = 54. Nodulisporacid A benzyl ester = 55. Nodulisporacid A methyl ester = 56. Norlichexanthone = 437. Nostocyclophane A = 620. Nostocyclophane B = 621. Nostocyclophane C = 622. Nostocyclophane D = 623. NSC 646282 = 84. O Obionin A = 856. Obioninene = 857. Octaphlorethol A = 553. Onchitriol I = 198. Onchitriol IA = 199. Onchitriol IB = 200. Onchitriol IC = 201. Onchitriol ID = 202. Onchitriol II = 203. Onchitriol IIA = 204. Onchitriol IIB = 205. Onchitriol IIC = 206. Onchitriol IID = 207. Oscillatoxin D = 243. Oxirapentyne E = 665. Oxisterigmatocystin A = 438.

Oxisterigmatocystin B = 439. Oxisterigmatocystin C = 440. 39-Oxobistramide K = 244. 8-[(2-Oxo-3-piperidinyl)amino]-8-oxooctyl-5,9anhydro-2,3,8-trideoxy-8-(5-hydroxy-4methyl-2-hexenyl)-3-methyl-DL-glycero-LDallo-non-2-enoate = 85. 4,4ʹ-[Oxybis(methylene)]bis[3,5,6-tribromo-1,2benzenediol] = 287. Oxyjavanicin = 852. P Pachybasin = 910. Paecilocin A = 644. Paecilocin B = 645. Paecilocin C = 646. Paecilospirone = 245. Paeciloxanthone = 441. Panicein A2 = 571. Panicein F1 = 572. Pectinatone = 148. (+)-Pederin = 86. Peneciraistin A = 698. Peneciraistin B = 699. Peneciraistin C = 700. Peneciraistin D = 701. Penexanthone A = 442. Penicilactone = 57. Penicillanthranin A = 702. Penicillide = 463. Penicitide A = 149. Penicitrinol C = 703. Penilactone A = 666. Penilactone B = 667. Peniphenone B = 150. Peniphenone C = 379. Penisporolide A = 246. Penisporolide B = 247. Penostatin A = 668. Penostatin B = 669. Penostatin C = 670. Penostatin D = 671. Penostatin E = 860. 2,3′,4,5,5′-Pentabromo-2′,6-dihydroxydiphenyl ether = 514. 2,3′,4,4′,5′-Pentabromo-2′-hydroxydiphenyl ether = 515. 2,3′,4,5,5′-Pentabromo-2′-hydroxy6-methoxydiphenyl ether = 516.

Index 1 Compound Name and Synonym Index

2′,5′,6′,5,6-Pentabromo-3′,4′,3,4tetramethoxybenzo-phenone = 389. 1,3,5,7,10-Pentahydroxy-1,9-dimethyl-2H-benzo [cd]pyrene-2,6(1H)-dione = 943. 1,2,3,6,8-Pentahydroxy-7-(1R-methoxyethyl) anthraquinone = 911. 2-Pentaprenyl-1,4-benzenediol = 283. Pergillin = 743. Peroniatriol I = 208. Peroniatriol II = 209. Pestalachloride C = 704. Pestalachloride D = 705. Pestaliopen A = 647. Pestalolide = 58. Pestalone = 390. Pestalotether A = 517. Pestalotether B = 518. Pestalotiopsone F = 672. Phenol A = 343. Phenol A acid = 270. N-Phenyl-1-naphthylamin = 782. Phialofurone = 629. 2-Phloro-6,6ʹ-bieckol = 554. 2-Phloroeckol = 555. 7-Phloroeckol = 556. Phlorofucofuroeckol A = 557. Phlorofucofuroeckol B = 558. Phloroglucinol = 284. 2,7ʹʹ-Phloroglucinol-6,6ʹ-bieckol = 559. Phlorotannin DDBT = 560. Phlorotannin representative trimer B = 561. Phlorotannin representative trimer C = 562. Phlorotannin representative trimer D = 563. Phomalactone = 151. Phomapyrone C = 152. Phomolactonexanthone A = 443. Phomolactonexanthone B = 444. Phomopsidin = 783. Phomopsis H76C = 153. Photodeoxytridachione = 210. Physcion = 912. Physcion-10,10′-cis–bianthrone = 871. Physcion-10,10′-trans–bianthrone = 872. Pinnamine = 211. Pinophilin A = 706. Pinophilin B = 707. Placidene A = 212. Placidene B = 213. Plakilactone C = 59.

Plakorfuran A = 12. Plakorsin B = 13. Plakorsin D = 60. Plakortone G = 61. Plakortoxide A = 62. Plakortoxide B = 63. Polyporapyranone A = 214. Polyporapyranone D = 215. 5,5ʹ-diepi-Δ3,Δ3ʹ-Popolohuanone E = 395. Popolohuanone E = 396. Populnin = 766. Porric acid D = 397. 2-Prenyl-1,4-naphthoquinone = 831. Prenylterphenyllin = 579. 3-[6-(1-Propenyl)-2H-pyran-2-ylidene]-2,4pyrrolidinedione = 87. Prunolide A = 248. Prunolide B = 249. Prunolide C = 250. Pseudodeflectusin = 742. Pseudopyronine A = 154. Psymberin = 761. Pterocidin = 155. Pulvic acid = 590. Pulvinic acid = 590. Purpurester A = 648. Purpurquinone B = 736. Purpurquinone C = 737. Pyrenocine A = 156. Pyrenocine B = 157. Pyrenocine E = 158. Q Questin 3-α-D-ribofuranoside = 913. R Rawsonol = 380. Redoxcitrinin = 306. Rhodosporin = 877. 3-O-(a-D-Ribofuranosyl)questin = 913. Rubrenoic acid A = 353. Rubrenoic acid B = 354. Rubrenoic acid C = 355. Rubrofusarin B = 801. Rubrolide A = 591. Rubrolide B = 592. Rubrolide C = 593. Rubrolide D = 594. Rubrolide E = 595.

339

340

Index 1 Compound Name and Synonym Index

Rubrolide F = 596. Rubrolide G = 597. Rubrolide H = 598. Rubrolide I = 599. Rubrolide K = 600. Rubrolide L = 601. Rubrolide M = 602. Rubrolide O = 603. Rubrolide R = 64. Rubrolide S = 65. S Sacrochromenol A sulfate = 673. Sacrochromenol B sulfate = 674. Sacrochromenol C sulfate = 675. Salinipyrone A = 159. Saliniquinone A = 922. Salinosporamide A = 1. Salinosporamide B = 2. Salinosporamide K = 3. Sarcophytonone = 373. Sargafuran = 14. Sargaquinoic acid = 374. (−)-Scleroderolide = 799. (15S,17S)-(−)-Sclerodinol = 930. (−)-Sclerodione = 934. (+)-Sclerotiorin = 738. (−)-Sclerotiorin = 739. Sculezonone A = 931. Sculezonone B = 932. Secochaetomugilin A = 740. Secochaetomugilin D = 741. 14,15-Secocurvularin = 317. Seriniquinone = 840. Simplactone A = 160. Simplactone B = 161. (5E)-Simplexolide = 66. (5E)-Simplexolide A = 67. (5Z)-Simplexolide A = 68. (5Z)-Simplexolide B = 69. (5E)-Simplexolide E = 70. Simplextone A = 71. Simplextone B = 72. Simplextone C = 73. Simplextone D = 74. Smenoquinone = 375. Sohirnone A = 318. Solanapyrone A = 162. Solanapyrone C = 163.

Solanapyrone E = 164. 7β-Solanapyrone F = 165. Solanapyrone F = 166. Solanapyrone G = 167. (4ʹZ)-Sorbicillin = 319. Spiculisporic acid B = 75. Spiculisporic acid D = 76. Spirastrellolide A = 251. Spirastrellolide B = 252. Spirastrellolide D = 253. Spirastrellolide E = 254. Spiromastixone A = 464. Spiromastixone B = 465. Spiromastixone C = 466. Spiromastixone D = 467. Spiromastixone E = 468. Spiromastixone F = 469. Spiromastixone G = 470. Spiromastixone H = 471. Spiromastixone I = 472. Spiromastixone J = 473. Spiromastixone K = 474. Spiromastixone L = 475. Spiromastixone M = 476. Spiromastixone N = 477. Spiromastixone O = 478. Spirostrellolide E = 252. Spiroxin A = 255. Spiroxin B = 256. Spiroxin C = 257. Spiroxin D = 258. Spiroxin E = 259. Spongiadioxin A = 519. Spongiadioxin B = 520. Spongiadioxin C = 521. Stachybogrisephenone B = 445. Strepchloritide A = 356. Strepchloritide B = 357. Stromemycin = 479. Subereaphenol B = 338. Sulfated cinnamic acid = 344. 2′′-O-Sulfoglucoluteolin = 764. (ξ)-Sydonic acid = 358. Sydowinin A = 446. Sydowinin B = 447. T Talaroflavone = 649. Talaromycesone A = 950.

Index 1 Compound Name and Synonym Index

Talaromycesone B = 951. TAN-931 = 448. (+)-Tanikolide = 168. Tanzawaic acid A = 784. Tedarene A = 522. Tedarene B = 541. Tenellic acid C = 330. Terphenyllin = 581. Terprenin = 580. Terrelactone = 24. Terrestrol A = 381. Terrestrol B = 293. Terrestrol C = 294. Terrestrol D = 295. Terrestrol E = 296. Terrestrol F = 382. Terrestrol G = 383. Terrestrol H = 384. Testufuran A = 15. 2,3′,4,5′-Tetrabromo-2′,6-dimethoxydiphenyl ether = 523. 3′,5′,6′,6-Tetrabromo-2,4-dimethyldiphenyl ether = 524. 3,3′,5,5′-Tetrabromo-2-hydroxy-2′,6dimethoxydiphenyl ether = 525. 2,2′,4,4′-Tetrabromo-6-hydroxydiphenyl ether = 526. 2,3′,4,5′-Tetrabromo-2′-hydroxydiphenyl ether = 527. 2,3′,4,5′-Tetrabromo-6-hydroxy-2′methoxydiphenyl ether = 528. 2,2ʹ,3,3ʹ-Tetrabromo-4,4ʹ,5,5ʹtetrahydroxydiphenylmethane = 385. Tetracenoquinocin = 924. 3′,4,5′,6-Tetrachloro-3-(2,4-dichlorophenoxy)2,2′-biphenyldiol. = 481. Tetracyclic salimabromide = 77. (all-Z)-5-(2,5,8,11-Tetradecatetraenyl)2-furanacetic acid = 16. Tetrahydroaltersolanol C = 914. Tetrahydrobostrycin = 866. 1,3,6,8-Tetrahydroxy-2-(1-hydroxyethyl) anthraquinone = 915. 1,3,6,8-Tetrahydroxy-2-(1-methoxyethyl) anthraquinone = 916. 2,3,6,8-Tetrahydroxy-1-methylxanthone = 401. Tetraorcinol A = 529. Tetrenolin = 53. Thalassiolin A = 764.

341

Thelepin = 630. Thiotropocin = 624. TMC 256A1 = 800. TMC 256A2 = 801. TMC 256C2 = 802. Tribromo-3-bromoamino-7bromomethylnaphthalene = 785. 2,5,8-Tribromo-3-bromoamino-7bromomethylnaphthalene = 786. 2,5,6-Tribromo-3-bromoamino-7bromomethylnaphthalene = 787. 3,5,6-Tribromo-1-(2ʹ-bromophenoxy)-2-benzene methyl ether = 530. 3,5,6-Tribromo-2-(2ʹ-bromophenoxy) phenol = 531. 3,4,6-Tribromo-2-(2ʹ-bromophenoxy) phenol = 532. 3,4,5-Tribromo-2-(2ʹ-bromophenoxy) phenol = 533. 2,3,4-Tribromo-6-(3,5-dibromo-2hydroxyphenoxy)phenol = 534. 3,4,6-Tribromo-2-(3,5-dibromo-2hydroxyphenoxy)phenol = 535. 2,3,6-Tribromo-4,5-dihydroxybenzaldehyde = 307. 2,3,6-Tribromo-4,5-dihydroxybenzyl alcohol = 297. 2,3,6-Tribromo-4,5-dihydroxybenzyl methyl ether = 298. 2,4,6-Tribromophenol = 266. 2,2′,3-Tribromo-3′,4,4′,5-tetrahydroxy-6′ethyloxymethyldiphenylmethane = 299. 2,4ʹ,5-Tribromo-2ʹ,3ʹ,6-trihydroxy-3,6ʹ-bis (hydroxymethyl)diphenyl ether = 536. 2,4,4ʹ-Trichloro-2ʹ-hydroxydiphenyl ether = 537. Trichodermaquinone = 917. Trichodermatide B = 676. Trichodermatide C = 677. Trichodermatide D = 678. Trichoharzin = 788. Tridachiapyrone A = 216. Tridachiapyrone B = 217. Tridachiapyrone D = 218. 1,3,8-Trihydroxyanthraquinone = 918. 3′,4,4′′-Trihydroxy-2′,6′-dimethoxy-pterphenyl = 542. 3′,4,4′′-Trihydroxy-2′,5′-dimethoxy-pterphenyl = 581.

342

Index 1 Compound Name and Synonym Index

2,3,3′-Trihydroxy-5,5′-dimethyldiphenyl ether = 490. 1,2,8-Trihydroxy-6-(hydroxymethyl)-9-oxo9H-xanthene-1-carboxylic acid methyl ester = 403. 4ʹ,5,7-Trihydroxyisoflavone = 767. 1,4,7-Trihydroxy-2-methoxy-6methylanthraquinone = 919. 1,3,8-Trihydroxy-6-methylanthraquinone = 898. 2,4,7-Trihydroxy-9-methyldibenz[b,e]oxepin-6 (11H)-one = 457. 2,4,7-Trihydroxy-9-methyldibenz[b,e]oxepin-6 (11H)-one = 458. 3,6,8-Trihydroxy-1-methylxanthone = 437. 2-O-(2,4,6-Trihydroxyphenyl)6,6ʹ-bieckol = 554. (3R,4S)-3,4,5-Trimethyisochroman6,8-diol = 708. Trioxacarcin A = 873. Trioxacarcin B = 874. Trioxacarcin C = 875. Tropolone = 625. (–)-Trypethelone = 795. Tuberatolide A = 78. Tuberatolide B = 79. 2ʹ-epi-Tuberatolide B = 80. Tubingenoic anhydride A = 81. U Ubiquinone 45 = 364.

Ulocladol = 543. Ustusorane E = 631. V Vanilloylformic acid = 332. Varioxirane = 359. Varitriol = 17. Varixanthone = 449. Velcide = 266. Vermelhotin = 87. Vermistatin = 219. Verrucosidin = 169. Vinaxanthone = 450. X Xanalteric acid I = 821. Xanalteric acid II = 822. Xestin A = 88. Xestin B = 89. Xiamenmycin C = 679. Xiamenmycin D = 680. Xylarone = 170. Y Yicathin B = 451. Yicathin C = 452. Yoshinone A = 220. Z Zooxanthellactone = 82.

Index 2 Compound Molecular Formula Index The Molecular Formula Index of Volume 7 lists the molecular formulae of all 951 active isolated compounds from marine organisms given in the HAMNP Volume 7 in Hill convention order. Under a bold formula, all related compound names following code numbers are listed in the code number order too. C5 C5H8O3 – Laurencione (cyclic hemiacetal form), 10. C6 C6H3Br2ClO – 2,4-Dibromo-6-chlorophenol, 260. C6H3Br3O – 2,4,6-Tribromophenol, 266. C6H4Br2O – 2,6-Dibromophenol, 261. – 2,4-Dibromophenol, 262. – 2,4-Dibromophenol Me ether, 263. C6H4Br2O2 – 5,6-Dibromocatechol, 268. C6H6O3 – Phloroglucinol, 284. C6H6O4 – 5-Hydroxy-4-(hydroxymethyl)2H-pyran-2-one, 132. C7 C7H3Br3O3 – 2,3,6-Tribromo-4,5-dihydroxybenzaldehyde, 307. C7H4BrClO3 – Bromochlorogentisylquinone A, 361. – Bromochlorogentisylquinone B, 362. C7H5Br3O3 – 2,3,6-Tribromo-4,5-dihydroxybenzyl alcohol, 297. C7H5ClO3 – Chlorogentisylquinone, 363. C7H6Br2O3 – 2,3-Dibromo-4,5-dihydroxybenzyl alcohol, 291. C7H6O2 – p-Hydroxybenzaldehyde, 304. – Tropolone, 625. C7H6O3 – 4-Hydroxybenzoic acid, 326.

C7H6O4 – 3,4-Dihydroxybenzoic acid, 325. C7H7ClO3 – 3-Chloro-4,5-dihydroxybenzyl alcohol, 288. – Chlorogentisyl alcohol, 289. C7H8O3 – Gentisyl alcohol, 292. C7H10O2 – 4,5-Dihydro-2,4-dimethyl-3-furancarboxaldehyde, 5. C7H10O3 – (S)-2-(2′-Hydroxyethyl)-4-methyl-γbutyrolac- tone, 49. – Harzialactone B, 129. C7H10O4 – Penicilactone, 57. C7H12O3 – Simplactone A, 160. – Simplactone B, 161. C8 C8H4O3S2 – Thiotropocin, 624. C8H7Br3O3 – 2,3,6-Tribromo-4,5-dihydroxybenzyl methyl ether, 298. C8H8O4 – 5-Hydroxy-2-methoxy benzoic acid, 327. – 2,6-Dimethoxy-1,4-benzoquinone, 365. C8H8O5 – Acetylsumiki’s acid, 4. C8H8O6S – Isojaspisin, 335. – Jaspisin, 336. C8H9ClO3 – 2-Chloro-6-(methoxymethyl)1,4-benzenediol, 290. C8H9NO4 – Honaucin A, 48. C8H10O3 – Phomalactone, 151. – 2-(Methoxymethyl)-1,4-benzenediol, 282.

344

Index 2 Compound Molecular Formula Index

C9 C9H7BrO3 – 5-Bromo-4,7-dihydroxy-1-indanone, 858. C9H8Br2O4 – Subereaphenol B, 338. C9H8O2 – Acetylbenzoyl, 308. C9H8O5 – Epicoccone, 639. C9H8O6S – Sulfated cinnamic acid, 344. C9H9Br2NO3 – (+)-Aeroplysinin 1, 331. C9H10O3 – Methyl 4-hydroxyphenylacetate, 337. C9H12O3 – 2,3-Dihydro-2-hydroxy-2,4-dimethyl-5-transpropenylfuran-3-one, 6. C9H12O4 – Asperlactone, 22. – Aspiketolactonol, 25. – Aspyrone, 93. – Chaetoquadrin F, 104. C9H13BrO4 – 4-Bromobeckerelide, 32. C9H13ClO4 – 9-Chloro-8-hydroxy-8,9-deoxyasperlactone, 36. – 8-Chloro-9-hydroxy-8,9-deoxyasperlactone, 37. – Chlorohydroaspyrone A, 106. – Chlorohydroaspyrone B, 107. C9H14O3 – Aspilactonol A, 26. C9H14O4 – Aspilactonol E, 30. – Aspilactonol F, 31. – Dihydroaspyrone, 124. C9H14O5 – Aspilactonol B, 27. – Aspilactonol C, 28. – Bissetone, 174. C10 C10H7Cl3O4 – Strepchloritide B, 357. C10H8Cl2O4 – Strepchloritide A, 356.

C10H8O5 – (±)-Acetophthalidin, 632. C10H10O4 – Communol F, 310. – 6-Hydroxymellein, 759. C10H10O5 – 4-Hydroxy-3-methoxyphenylglyoxylic acid methyl ester, 332. C10H10O6 – 3,4-Dihydro-3,4,6,8-tetrahydroxy-3-methyl -1H-2-benzopyran-1-one, 756. C10H12O3 – 2,4-Dihydroxy-3,5,6-trimethylbenzaldehyde, 269. – (3S)-(3,5-Dihydroxyphenyl)butan-2-one, 339. – 6,7-Dihydro-3-(hydroxymethyl)-6-methyl-4 (5H)-benzofuranone, 626. C10H12O4 – Cillifuranone, 38. – Hydroxypestalopyrone, 133. C10H14O3 – Phomapyrone C, 152. C10H15ClO3 – 9-Chloro-8-hydroxy-8,9-deoxyaspyrone, 108. C10H16O5 – Aspilactonol D, 29. – Aspyronol, 94. C11 C11H7ClO3 – Polyporapyranone D, 215. C11H10O4 – Diaporthelactone, 638. C11H10O5 – 5-Carboxymellein, 753. – Decarboxyhydroxycitrinone, 754. C11H12BrIO4 – Acetoxyfimbrolide D, 20. C11H12Br2O4 – Acetoxyfimbrolide A, 18. – Acetoxyfimbrolide B, 19. C11H12O2 – Acremonin A, 271. – 2,2-Dimethyl-2H-1-benzopyran-6-ol, 662. C11H12O3 – Harzialactone A, 47. – Nakitriol, 352. – (–)-5-Methylmellein, 763.

Index 2 Compound Molecular Formula Index

C11H12O4 – Lissoclinolide, 53. – Nigerapyrone E, 146. – Pyrenocine A, 156. – 2-Hydroxy-3,5-dimethyl-6-(2-oxopropyl)1,4-benzoquinone, 369. – Marilone B, 641. C11H14O3 – Nectriapyrone A, 140. C11H14O4 – Communol G, 311. C11H14O5 – Chlamydosporol, 105. – Pyrenocine B, 157. C11H16O3 – Tubingenoic anhydride A, 81. – Phenol A, 343. C11H16O4 – 6-Hydroxy-5-methylramulosin, 760. C12 C12H4Br4O3 – Spongiadioxin A, 519. – Spongiadioxin B, 520. C12H4Br6O3 – 2,3,3′,4,5,5′-Hexabromo-2′,6dihydroxydiphenyl ether, 508. C12H5Br3O3 – Spongiadioxin C, 521. C12H5Br4ClO2 – 2,3-Dibromo-5-chloro-6-(2,4-dibromophenoxy) phenol, 492. C12H5Br5O2 – 2-(2,4-Dibromo-phenoxy)-3,4,5tribromophenol, 498. – 2,3′,4,4′,5′-Pentabromo-2′-hydroxydiphenyl ether, 515. C12H5Br5O3 – 3,5-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹhydroxy- phenoxy) phenol, 499. – 4,6-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹhydroxy- phenoxy) phenol, 500. – 2,3′,4,5,5′-Pentabromo-2′,6dihydroxydiphenyl ether, 514. – 2,3,4-Tribromo-6-(3,5-dibromo-2hydroxyphen-oxy)phenol, 534. – 3,4,6-Tribromo-2-(3,5-dibromo-2hydroxyphen-oxy)phenol, 535.

345

C12H6Br4O2 – 2,2′,4,4′-Tetrabromo-6-hydroxydiphenyl ether, 526. – 2,3′,4,5′-Tetrabromo-2′-hydroxydiphenyl ether, 527. – 3,5,6-Tribromo-2-(2ʹ-bromophenoxy) phenol, 531. – 3,4,6-Tribromo-2-(2ʹ-bromophenoxy) phenol, 532. – 3,4,5-Tribromo-2-(2ʹ-bromophenoxy) phenol, 533. C12H7Br5 – Tribromo-3-bromoamino-7bromomethylnaphthalene, 785. – 2,5,8-Tribromo-3-bromoamino-7bromomethyl-naphthalene, 786. – 2,5,6-Tribromo-3-bromoamino-7-bromomethylnaphthalene, 787. C12H7Cl3O2 – 2,4,4ʹ-Trichloro-2ʹ-hydroxydiphenyl ether, 537. C12H8O4 – Pulvic acid, 590. C12H8O6 – Dibenzo [1,4]dioxine-2,4,7,9-tetraol, 546. C12H10O3 – Diorcinol, 503. – Accinal A, 772. C12H10O4 – Cordyol C, 489. C12H10O6 – Esculetin-4-carboxylic acid ethyl ester, 686. C12H11NO3 – Vermelhotin, 87. C12H12O3 – 2,3-Dihydro-1-methoxy-6-methyl-3-oxo-1Hindene-4-carboxaldehyde, 859. C12H12O4 – Chromanone A, 657. C12H12O5 – 7-epi-Austdiol, 690. C12H13BrO4 – Hiburipyranone, 758. C12H14Br2O5 – Bromomethylchlamydosporol B, 102. C12H14O3 – Felinone B, 627. – Isoacremine D, 628.

346

Index 2 Compound Molecular Formula Index

C12H14O4 – (3R,4S)-6,8-Dihydroxy-3,4,5-trimethyisochroman-1-one, 757. C12H14O5 – Balticol B, 774. C12H14O6 – Balticol C, 775. C12H15BrO5 – Bromomethylchlamydosporol A, 101. C12H16O2 – (E)-6-(1-Heptenyl)-2H-pyran-2-one, 131. C12H16O3 – (3R,4S)-3,4,5-Trimethyisochroman6,8-diol, 708. C12H16O4 – Citrinin H2, 267. C12H16O5 – Pyrenocine E, 158. – Phenol A acid, 270. C12H18O3 – Helicascolide C, 130. C12H20O2 – Pestalolide, 58. C12H20O4 – Isocladospolide B, 52. C13 C13H6Br4O3 – O-Methylspongiadioxin A, 510. – O-Methylspongiadioxin B, 511. C13H7Br3O3 – O-Methylspongiadioxin C, 512. C13H7Br5O3 – 4,6-Dibromo-2-(4ʹ,5ʹ,6ʹ-tribromo-2ʹ-hydroxyphenoxy) phenol-1-methylether, 501. – 2,3′,4,5,5′-Pentabromo-2′-hydroxy-6-methoxydiphenyl ether, 516. C13H8Br4O2 – 3,5,6-Tribromo-1-(2ʹ-bromophenoxy)-2benzene methyl ether, 530. C13H8Br4O3 – 3,5-Dibromo-2-(2,4-dibromophenoxy)-4methoxyphenol, 493. – 4,6-Dibromo-2-(2ʹ-methoxy-4ʹ,6ʹ-dibromophenoxy)phenol, 494. – 2-(4,6-Dibromo-2-methoxy-phenoxy)-3,5dibromophenol, 496. – 2,3′,4,5′-Tetrabromo-6-hydroxy-2′-methoxydiphenyl ether, 528.

C13H8Br4O4 – 2,2ʹ,3,3ʹ-Tetrabromo-4,4ʹ,5,5ʹ-tetrahydroxydiphenylmethane, 385. C13H9Br3O3 – 2-(5-Bromo-2-methoxy-phenoxy)-3,5-dibromophenol, 485. – 2-(3,5-Dibromo-2-methoxy-phenoxy)-3-bromophenol, 495. C13H11NO3 – Carbonarone A, 175. – Carbonarone B, 176. C13H12O4 – Polyporapyranone A, 214. C13H14O3 – 6-Demethylsorbicillin, 313. – 2,3-Dihydro-7-hydroxy-6-methyl-2-(1-propenyl)-4H-1-benzopyran-4-one, 661. C13H14O5 – 3-Acetyl-7-hydroxy-5-methoxy-3,4-dimethyl- 1 (3H)-isobenzofuranone, 633. – Citrinin, 691. – 8-O-Methyl-epi-austdiol, 697. C13H16O3 – Cyercene 1, 114. – 8,9-Dehydroxylarone, 120. – Sohirnone A, 318. – 3-Butyl-7-methoxyphthalide, 635. C13H16O4 – Redoxcitrinin, 306. – Methyl 4-hydroxy-3-(3-methylbut-2-enyloxy) benzoate, 329. C13H16O5 – Ethyl 5-ethoxy-2-formyl-3-hydroxy-4-methylbenzoate, 314. – 4-Hydroxyphenethyl methyl succinate, 334. – Purpurester A, 648. C13H16O6 – (2′S)-4-Methoxy-3-(2′-methyl-3′-hydroxy) propionyl-methyl benzoate, 328. C13H17NO4 – Salinosporamide K, 3. C13H18O3 – Xylarone, 170. C13H19NO2 – Pinnamine, 211. C13H20O3 – Hyalopyrone, 185. C13H22O3 – Antibiotic MKN 003C, 21.

Index 2 Compound Molecular Formula Index

C14 C14H8Br6O4 – 1,2-Bis(2,3,6-tribromo-4,5-dihydroxyphenyl) ethane, 565. C14H8Br6O5 – Bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether, 287. C14H8O4 – 1,8-Dihydroxyanthraquinone, 889. C14H8O5 – 1,3,8-Trihydroxyanthraquinone, 918. C14H9Br3O3 – Thelepin, 630. C14H9Br5O2 – 2-(3,5-Dibromo-2-methoxy-phenoxy)-3,4,5tribromoanisole, 497. C14H9NO6 – Antibiotic SB236049, 653. C14H10Br4O – 3′,5′,6′,6-Tetrabromo-2,4-dimethyldiphenyl ether, 524. C14H10Br4O3 – 2,3′,4,5′-Tetrabromo-2′,6-dimethoxydiphenyl ether, 523. C14H10Br4O4 – 3,3′,5,5′-Tetrabromo-2-hydroxy-2′,6dimethoxy-diphenyl ether, 525. C14H10Br4O5 – BDDE, 285. – Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether, 286. C14H10O5 – 1,7-Dihydroxy-9-methyldibenzo[b,d] furan-3carboxylic acid, 391. – Norlichexanthone, 437. C14H10O6 – Anomalin A, 401. C14H10O7 – Anhydrofulvic acid, 681. C14H11Br3O6 – 2,4ʹ,5-Tribromo-2ʹ,3ʹ,6-trihydroxy-3,6ʹ-bis (hydroxymethyl)diphenyl ether, 536. C14H12O3 – 3,9-Dimethyldibenzo[b,d]furan1,7-diol, 392. C14H12O4 – 3-(Hydroxymethyl)-9-methyldibenzo[b,d] furan-1,7-diol, 393.

347

C14H12O5 – 1-Deoxyrubralactone, 755. C14H12O6 – Talaroflavone, 649. C14H13ClO5 – Terrestrol B, 293. – Terrestrol D, 295. – Terrestrol F, 382. – Terrestrol G, 383. C14H13NO4 – Albidopyrone, 90. C14H14Br2O4 – Avrainvilleol, 376. C14H14O3 – Diorcinol, 504. – Diorcinol, 505. C14H14O4 – Cordyol Cʹ, 490. C14H14O5 – Terrestrol C, 294. – Terrestrol E, 296. C14H16O3 – Isosorbicillin, 315. – (2R)-2,3-Dihydro-7-hydroxy-6,8-dimethyl-2[(E)-prop-l-enyl]chromen-4-one, 660. C14H16O4 – Nigerapyrone D, 145. – 2-Hydroxy-3,6-dimethyl-5-(1-oxo-4-hexenyl)1,4-benzoquinone, 368. – Phialofurone, 629. – Aspergillumarin A, 750. C14H16O5 – Balticol A, 773. C14H16O6 – Balticol D, 776. C14H16O7 – (4ʹZ)-Sorbicillin, 319. C14H17Cl2NO3 – Ayamycin, 360. C14H18O3 – Cyercene 2, 115. – Cyercene 4, 117. – 7-Methylcyercene 1, 139. – Cyercene B, 181. C14H18O4 – Corollosporin, 636. – Penicitrinol C, 703. – Aspergillumarin B, 751.

348

Index 2 Compound Molecular Formula Index

C14H18O5 – 3′,4′-Dihydroinfectopyrone, 125. C14H18O6 – Balticol E, 777. C15 C15H10O3 – Pachybasin, 910. C15H10O4 – Chrysophanol, 888. – 1,4-Dihydroxy-6-methylanthraquinone, 893. C15H10O5 – Monodictyxanthone, 436. – Genistein, 767. – Emodin, 898. C15H10O6 – Yicathin C, 452. C15H10O7 – TAN-931, 448. C15H12O5 – Corynesidone A, 456. – 9-Dehydroxyeurotinone, 457. – 9-Dehydroxyeurotinone, 458. – TMC 256A1, 800. C15H12O6 – Isomonodictyphenone, 387. – Monodictyphenone, 388. – Porric acid D, 397. – Anhydrofusarubin, 851. C15H12O7 – Globosuxanthone A, 426. C15H12O8 – Antibiotic SB238569, 683. C15H13NO2 – Aspergillitine, 655. C15H14O2 – Deoxylapachol, 831. C15H14O5 – 2,3-Dihydro-5-hydroxy-8-methoxy-2,4dimethylnaphtho[1,2-b]furan6,9-dione, 791. C15H14O6 – Altenusin, 538. – Fonsecin, 797. – Javanicin tautomeric with 5,8-quinone structure, 837. – Trichodermaquinone, 917. C15H14O7 – Fusarubin, 852.

C15H14O8 – Antibiotic SB236050, 682. C15H16O3 – Cordyol E, 491. C15H16O4 – Aspergione B, 742. – Pergillin, 743. C15H16O5 – Terrestrol H, 384. – Ascochitin, 687. – Fusarnaphthoquinone B, 833. C15H16O6 – Peneciraistin D, 701. C15H16O7 – Ascolactone B, 634. C15H18O – Echinofuran‡., 7. C15H18O5 – Monodictysin B, 434. C15H18O6 – Ascochital, 320. – Monodictysin A, 433. – Balticol F, 778. C15H18O7 – Fusarnaphthoquinone A, 832. C15H19ClO2 – Coibacin C, 111. C15H20ClNO4 – Salinosporamide A, 1. C15H20O3 – Cyercene 3, 116. – Cyercene 5, 118. – Isoplacidene B, 188. – Placidene B, 213. C15H20O4 – 1,11-Dihydroxy-1,3,5,7E-bisabolatetren-15-oic acid, 348. C15H20O5 – Varitriol, 17. – Varioxirane, 359. – Dothiorelone D, 694. – Peneciraistin A, 698. – Peneciraistin B, 699. C15H21ClO2 – Coibacin D, 112. C15H21NO4 – Salinosporamide B, 2. C15H22O2 – Aspergillusene A, 345.

Index 2 Compound Molecular Formula Index

– (Z)-5-(Hydroxymenthyl)-2-(6′-methylhept-2′-en2′-yl)-phenol, 349. C15H22O4 – (ξ)-Sydonic acid, 358. – Ustusorane E, 631. C15H22O5 – Cytosporone E, 637. C15H24O3 – Plakorsin D, 60. C16 C16H10O3S – Bryoanthrathiophene, 936. C16H10O4S – 5,7-Dihydroxy-1-(hydroxymethyl)-6H-anthra [1,9-bc]thiophen-6-one, 941. C16H11ClO6 – Engyodontiumone B, 418. C16H12Br2O11S2 – Aplysillin A, 564. C16H12O4 – 1-Methoxy-3-methyl-8-hydroxyanthraquinone, 907. C16H12O5 – 8-Hydroxy-3-methyl-9-oxo-9Hxanthene-1- carboxylic acid methyl ether, 429. – 1,4-Dihydroxy-2-methoxy-7-methylanthraquinone, 891. – 1,3-Dihydroxy-6-methoxy-8-methylanthraquinone, 892. – 1,3-Dihydroxy-6-methyl-8-methoxyanthraquinone, 894. – Monodictyquinone, 909. – Physcion, 912. C16H12O6 – Sydowinin A, 446. – Yicathin B, 451. – Evariquinone, 899. – 1,4,7-Trihydroxy-2-methoxy-6-methylanthraquinone, 919. C16H12O7 – Sydowinin B, 447. – 1,3,6,8-Tetrahydroxy-2-(1-hydroxyethyl) anthraquinone, 915. C16H13N – N-Phenyl-1-naphthylamin, 782. C16H14O5 – 2-O-Methyl-9-deoxyeurotinone, 462.

349

– TMC 256A2, 801. – TMC 256C2, 802. C16H14O6 – Nigerasperone A, 798. C16H14O7 – Antibiotic AGI-B4, 402. – Engyodontiumone C, 419. – Engyodontiumone H, 424. – (2β)-Engyodontiumone H, 425. – Ulocladol, 543. C16H14O8 – Aspergillusone B, 403. C16H15Br3O5 – 2,2′,3-Tribromo-3′,4,4′,5-tetrahydroxy-6′ethyloxymethyldiphenylmethane, 299. C16H15ClO6 – Stachybogrisephenone B, 445. – Pestalotether B, 518. C16H15NO5 – (–)-Cereoaldomine, 789. C16H16O4 – 4-Hydroxyphenethyl 2-(4-hydroxyphenyl) acetate, 333. – (–)-Trypethelone, 795. C16H16O6 – Communol A, 309. – 5,7-Dideoxybostrycin, 878. – Nigrosporin B, 880. C16H16O7 – Engyodontiumone D, 420. – (±)-Engyodontiumone E, 421. – 3-O-Methylfusarubin, 855. – Austrocortirubin, 876. – 5-Deoxybostrycin, 879. C16H16O8 – (±)-Engyodontiumone F, 422. – (±)-Engyodontiumone G, 423. – Bostrycin, 877. C16H20Br2O2 – Cymobarbatol, 398. – Isocymobarbatol, 400. C16H20O2 – Rubrenoic acid B, 354. – Rubrenoic acid C, 355. – 2-(1,1-Dimethyl-2-propenyl)-5-(3-methyl-2butenyl)-1,4-benzoquinone, 366. – Chromenol, 658. C16H20O5 – Oxirapentyne E, 665.

350

Index 2 Compound Molecular Formula Index

C16H20O6 – Nodulisporacid A, 54. – Monodictysin C, 435. – Tetrahydroaltersolanol C, 914. C16H20O7 – Fusaquinone C, 867. – Fusaranthraquinone, 868. – 9α-Hydroxydihydrodesoxybostrycin, 869. C16H20O8 – Fusaquinone B, 866. – 9α-Hydroxyhalorosellinia A, 870. C16H21BrO2 – Debromoisocymobarbatol, 399. C16H21Br2NO3 – Ethyl 3,5-dibromo-4(3ʹN,N-dimethylaminopropyloxy)-cinnamate, 340. C16H22O – 4-(1,1-Dimethyl-2-propenyl)-2-(3-methyl-2butenyl)phenol, 264. – 2,4-Diprenylphenol, 265. C16H22O2 – Comosusol C, 276. – Geroquinol, 278. – Rubrenoic acid A, 353. C16H22O3 – Cyercene A, 180. – Isoplacidene A, 187. – Placidene A, 212. – Comosusol A, 274. – Comosusol B, 275. – Paecilocin A, 644. C16H22O4 – Butyl-isobutylphthalate, 324. – Cytosporone C, 692. C16H22O5 – 14,15-Secocurvularin, 317. C16H24O2 – Comosone A, 273. C16H24O3 – Plakilactone C, 59. – 2-(7-Hydroxy-3,7-dimethyl-2-octenyl)-1,4benzenediol, 279. – 2-(3-Hydroxy-3,7-dimethyl-6-octenyl)-1,4benzenediol, 280. – Trichodermatide C, 677. C16H24O4 – Trichodermatide B, 676. – Trichodermatide D, 678.

C16H24O5 – Comosusol D, 277. C16H26Br2O4 – Mutafuran H, 11. C16H26O3 – Pseudopyronine A, 154. – Marinactinone B, 192. – Marinactinone C, 193. C16H30O3 – (–)-Malyngolide, 137. C17 C17H7Br4ClO4 – Rubrolide B, 592. C17H8Br3ClO4 – Rubrolide I, 599. C17H8Br4O4 – Rubrolide A, 591. C17H9Br2ClO4 – Rubrolide K, 600. – Rubrolide L, 601. – Rubrolide O, 603. C17H9Br4ClO5 – Rubrolide H, 598. C17H10BrClO4 – Rubrolide M, 602. C17H10Br2O4 – Rubrolide C, 593. – Rubrolide D, 594. C17H10Br4O5 – Rubrolide G, 597. C17H10O5S – 5,7-Dihydroxy-6-oxo-6H-anthra[1,9-bc]thiophene-1-carboxylic acid, methyl ester, 942. C17H12O4 – Rubrolide E, 595. C17H12O5 – Isoaspulvinone E, 50. – Aspulvinone E, 582. – Isoaspulvinone E, 589. C17H13Br5O5 – 2′,5′,6′,5,6-Pentabromo-3′,4′,3,4tetramethoxy- benzo-phenone, 389. C17H14O4 – Eutypoid B, 39. – 1,3-Dimethoxy-6-methylanthraquinone, 895. C17H14O5 – Eutypoid C, 40.

Index 2 Compound Molecular Formula Index

– Eutypoid D, 41. – 1-Hydroxy-2,4-dimethoxy-7-methylanthraquinone, 905. C17H14O6 – Eutypoid E, 42. – 1,7-Dihydroxy-2,4-dimethoxy-6-methylanthraquinone, 890. C17H14O7 – 1,3,6,8-Tetrahydroxy-2-(1-methoxyethyl) anthrax-quinone, 916. C17H14O8 – 1,2,3,6,8-Pentahydroxy-7-(1R-methoxyethyl) anthraquinone, 911. C17H16Br2O4 – Colpol, 567. C17H16O5 – Coniolactone, 779. C17H16O8 – Chaetocyclinone A, 684. C17H17ClO6 – Grisephenone A, 427. C17H17NO4 – (–)-Cereolactam, 790. C17H20O5 – 4-(3-Hydroxypropyl)-5,6-dimethoxybiphenyl3,4ʹ-diol, 540. – Pestalotiopsone F, 672. C17H20O6 – Mycophenolic acid, 643. C17H21NO3 – Solanapyrone G, 167. C17H21NO4 – 7β-Solanapyrone F, 165. – Solanapyrone F, 166. C17H22O2 – Coibacin B, 110. – Lorneic acid A, 350. C17H22O6 – Nodulisporacid A methyl ester, 56. C17H22O7 – Acremonin A 5-β-glucopyranoside, 272. C17H23ClO5 – Chaetomugilin R, 728. C17H23NO3 – Xiamenmycin C, 679. C17H24O3 – Lorneic acid B, 351. C17H24O4 – Salinipyrone A, 159.

C17H26O5 – Penisporolide B, 247. C17H26O6 – Spiculisporic acid B, 75. C17H28O3 – Plakortoxide A, 62. C17H30O3 – (5E)-Simplexolide A, 67. – (5Z)-Simplexolide A, 68. – (5Z)-Simplexolide B, 69. – (5E)-Simplexolide E, 70. C17H30O4 – Simplextone B, 72. – Simplextone D, 74. C17H32O3 – (+)-Tanikolide, 168. C18 C18H8Cl6O3 – Ambigol A, 481. – Ambigol B, 482. – Ambigol C, 483. C18H10O9 – Dioxinodehydroeckol, 548. C18H12O9 – Eckol, 550. C18H14O4 – Rubrolide F, 596. C18H14O6 – (2E,2ʹZ)-3,3ʹ-(6,6ʹ-Dihydroxybiphenyl-3,3ʹdiyl)diacrylic acid, 539. C18H14O7 – Dimethyl 8-methoxy-9-oxo9H-xanthene-1,6-dicarboxylate, 414. C18H16O5 – Coniosclerodione, 933. – (−)-Sclerodione, 934. C18H16O6 – Isobutyrolactone II, 51. – Vermistatin, 219. – (−)-Scleroderolide, 799. – Isorhodoptilometrin-1-methyl ether, 906. – Conioscleroderolide, 927. C18H16O7 – Karanjapin, 768. – (E)-Coniosclerodinol, 928. – (Z)-Coniosclerodinol, 929. – (15S,17S)-(−)-Sclerodinol, 930.

351

352

Index 2 Compound Molecular Formula Index

C18H16O8 – Phlorotannin representative trimer D, 563. C18H16O9 – Phlorotannin DDBT, 560. – Phlorotannin representative trimer B, 561. – Phlorotannin representative trimer C, 562. C18H17ClO8 – Pestalotether A, 517. C18H18O6 – Chromanone, 177. – Peniphenone C, 379. C18H20O6 – (–)-Byssochlamic acid, 171. – Apralactone A, 654. C18H22O4 – Solanapyrone A, 162. C18H22O5 – Nigrosporapyrone A, 147. C18H24O4 – Solanapyrone E, 164. – Glabruquinone A, 367. C18H25BrO3 – Testufuran A, 15. C18H26O2 – Caulerprenylol A, 346. – Caulerprenylol B, 347. – Tanzawaic acid A, 784. C18H26O3 – Tuberatolide A, 78. C18H26O5 – Cytosporone B, 312. C18H28O4 – Paecilocin B, 645. – Paecilocin C, 646. C18H30O2 – Plakortone G, 61. C18H30O3 – Plakortoxide B, 63. C18H30O4 – Simplextone C, 73. C18H30O5 – Penisporolide A, 246. C18H30O6 – Spiculisporic acid D, 76. C18H32O3 – (5E)-Simplexolide, 66. C18H32O4 – Simplextone A, 71.

C18H34O4 – Penicitide A, 149. C19 C19H14O6 – 3ʹʹ-Deoxy-6ʹ-O-desmethylcandidusin B, 573. C19H16Cl4O5 – Spiromastixone I, 472. – Spiromastixone O, 478. C19H16O5 – 6ʹ-O-Desmethylterphenyllin, 577. C19H16O6 – 3-Hydroxy-6ʹ-O-desmethylterphenyllin, 578. C19H16O7 – (+)-Butyrolactone II, 34. – Oxisterigmatocystin C, 440. C19H17Cl3O5 – Spiromastixone F, 469. – Spiromastixone H, 471. – Spiromastixone N, 477. C19H17O5S1– – Tedarene B, 541. C19H18Cl2O5 – Spiromastixone D, 467. – Spiromastixone E, 468. – Spiromastixone M, 476. C19H18O2 – Tedarene A, 522. C19H18O7 – 5ʹ-Methoxyvermistatin, 197. C19H19ClO5 – Spiromastixone B, 465. – Spiromastixone C, 466. C19H20O5 – Spiromastixone A, 464. C19H20O7 – Annulin A, 826. C19H20O8 – Dimethyl-2,3ʹ-dimethylosoate, 502. C19H22O3 – Diorcinol D, 506. C19H22O4 – Awajanoran, 484. – Diorcinol E, 507. – Abietinarin A, 861. – Abietinarin B, 862. C19H24O2 – Coibacin A, 109.

Index 2 Compound Molecular Formula Index

C19H24O3 – Isodihydroauroglaucin, 305. C19H24O4 – Chaetopyranin, 301. C19H24O5 – Keisstetralone, 780. C19H25NO4 – Solanapyrone C, 163. C19H26O9 – Peneciraistin C, 700. C19H28O3 – Flavoglaucin, 303. C19H28O6 – 5-O-Methyldothiorelone A, 316. C19H30O4 – Plakorfuran A, 12. C19H36O3 – (2S,3S,5R)-5-[(1R)-1-Hydroxydec-9-enyl]-2pentyltetrahydrofuran-3-ol, 8. – (2S,3S,5S)-5-[(1S)-1-Hydroxydec-9-enyl]-2pentyltetrahydrofuran-3-ol, 9. C20 C20H8Cl2O8 – Spiroxin B, 256. C20H8O4S – Seriniquinone, 840. C20H9ClO8 – Spiroxin A, 255. C20H10Cl2O8 – Spiroxin E, 259. C20H10O7 – Spiroxin C, 257. C20H12O7 – Spiroxin D, 258. – Xanalteric acid I, 821. – Xanalteric acid II, 822. C20H13Br5O6 – 3-Bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)pyrocatechol, 377. C20H14O7 – Ascochytatin, 222. C20H16O9 – Griseusin C, 834. C20H18Cl4O5 – Spiromastixone J, 473. – Spiromastixone L, 475. C20H18O3 – Anthracene derivative 100, 863.

353

C20H18O4 – Kiamycin, 944. C20H18O5 – 1,7-Dihydroxy-2-methoxy-3-(3-methylbut-2enyl)-9H-xanthen- 9-one, 413. – 3′,4,4′′-Trihydroxy-2′,6′-dimethoxy-pterphenyl, 542. – 3′,4,4′′-Trihydroxy-2′,5′-dimethoxy-pterphenyl, 581. C20H18O6 – Chaetoxanthone B, 405. – 1-Hydroxy-4,7-dimethoxy-6-(3-oxobutyl)-9Hxanthen-9-one, 428. C20H18O7 – Chaetoxanthone A, 404. – 6-Desmethoxyhormothamnione, 693. C20H18O8 – Oxisterigmatocystin A, 438. – Oxisterigmatocystin B, 439. C20H19ClO6 – Chaetoxanthone C, 406. C20H19Cl3O5 – Spiromastixone G, 470. – Spiromastixone K, 474. C20H20Br2O3 – Tetracyclic salimabromide, 77. C20H20O3 – Asnipyrone B, 92. C20H20O4 – Paeciloxanthone, 441. C20H20O8 – Sculezonone A, 931. C20H20O9 – Sculezonone B, 932. C20H22O7 – Annulin C, 828. C20H23NO6 – Hibiscusamide, 342. C20H23NO7 – Antibiotic AI 77F, 747. C20H26N2O7 – Amicoumacin C, 746. C20H26O3 – (all-Z)-5-(2,5,8,11-Tetradecatetraenyl)-2-furanacetic acid, 16. – 3-(2-Acetoxy-4,8-dimethyl-3,7-nonadienyl) benzaldehyde, 300. C20H26O4 – Marilone C, 642.

354

Index 2 Compound Molecular Formula Index

C20H26O6 – Terprenin, 580. C20H28N2O8 – Amicoumacin B, 745. C20H28O4 – Kalkipyrone, 189. C20H29N3O7 – Amicoumacin A, 744. C20H30O5 – Sarcophytonone, 373. C20H35NO8 – Mycalamide C, 83. C21 C21H14O7 – 1-Hydroxy-1-norresistomycin, 943. C21H18O8 – Peniphenone B, 150. C21H20Cl2O5 – Pestalachloride C, 704. – Pestalachloride D, 705. C21H20Cl2O6 – Pestalone, 390. C21H20O3 – Nigerapyrone B, 144. C21H20O6 – Galvaquinone B, 902. C21H20O7 – Halawanone C, 903. C21H20O8 – Hormothamnione, 695. – Purpurquinone C, 737. C21H20O9 – Questin 3-α-D-ribofuranoside, 913. C21H20O10 – Purpurquinone B, 736. C21H20O11 – Populnin, 766. C21H20O14S – Thalassiolin A, 764. C21H22O3 – Asnipyrone A, 91. C21H22O5 – Obioninene, 857. C21H22O7 – Pinophilin A, 706. – Comazaphilone D, 733. – Annulin B, 827.

C21H22O8 – Pinophilin B, 707. C21H22O9 – 2-O-Methyl-4-O-(a-D-ribofuranosyl)-9deoxyeurotinone, 460. C21H23ClO5 – (+)-Sclerotiorin, 738. – (−)-Sclerotiorin, 739. C21H24O5 – Obionin A, 856. C21H24O6 – Penicillide, 463. C21H24O9 – Asperflavin 6-O-α-D-Ribofuranoside, 864. C21H28O2 – (±)-Dictyochromenol, 659. C21H28O4 – Smenoquinone, 375. – Marilone A, 640. C21H30O3 – Phomopsidin, 783. C21H32O3 – Diemenensin A, 122. – Diemenensin B, 123. C21H32O5 – Yoshinone A, 220. C21H34O3 – Isopectinatone, 134. – Pectinatone, 148. C21H34O4S – Lehualide D, 191. C21H38O3 – Flavalactone 1, 43. C22 C22H18O5 – 2-Benzyl-5-hydroxy-6,8-dimethoxy4H-benzo[g]chromen-4one, 796. C22H18O6 – γ-Indomycinone, 920. C22H18O8 – Bicoumanigrin, 685. C22H20O4 – Rubrolide R, 64. – Rubrolide S, 65. C22H20O6 – Arugosin H, 386.

Index 2 Compound Molecular Formula Index

C22H20O9 – Halawanone B, 854. C22H20O10 – Aflatoxin B2b, 650. C22H21NO7 – Azaspirofuran A, 224. C22H22O5 – Flavipesin A, 46. C22H22O7 – Terrestrol A, 381. – Halawanone D, 904. C22H24O6 – Nodulisporacid A benzyl ester, 55. – 3ʹ-O-Methyldehydroisopenicillide, 461. C22H24O7 – 7-O-Acetylsecopeni-cillide C, 480. – 6,8-Di-O-methylaverantin, 896. C22H24O8 – Comazaphilone C, 732. – Comazaphilone E, 734. – Anhydroexfoliamycin, 850. C22H26O3 – Panicein A2, 571. C22H26O7 – Comazaphilone A, 730. C22H26O8 – Comazaphilone B, 731. – Comazaphilone F, 735. C22H27ClO4 – Chaetomugilin J, 721. C22H27ClO5 – Chaetomugilin I, 719. – 11-epi-Chaetomugilin I, 720. – Chaetomugilin P, 726. C22H28O4 – Panicein F1, 572. C22H29ClO6 – Chaetomugilin Q, 727. C22H29NO8 – Himeic acid A, 184. C22H30O2 – Zooxanthellactone, 82. – Penostatin C, 670. C22H30O3 – Photodeoxytridachione, 210. C22H30O4 – Ilimaquinone, 370. – 5-epi-Ilimaquinone, 371.

C22H31NO6 – Xiamenmycin D, 680. C22H32O3 – Penostatin A, 668. – Penostatin B, 669. – Penostatin E, 860. C22H34N2O6 – Antibiotic PM94128, 748. C22H34O3 – Penostatin D, 671. C22H38O3 – Plakorsin B, 13. C22H38O5 – Attenol A, 223. C23 C23H16O7 – Saliniquinone A, 922. C23H19Br2NO5 – Ammonificin D, 652. C23H20BrNO6 – Ammonificin C, 651. C23H21Cl3O5 – Microsphaerol, 513. C23H22O9 – Halawanone A, 853. C23H25ClO5 – Guisinol, 459. – Chaetomugilin F, 716. – Chaetomugilin O, 725. C23H25ClO6 – Chaetomugilin C, 713. – Chaetomugilin N, 724. C23H26O8 – Tenellic acid C, 330. C23H27ClO6 – Chaetomugilin D, 714. – Chaetomugilin S, 729. C23H27ClO7 – Chaetomugilin A, 709. – 4′-epi-Chaetomugilin A, 710. – 11-epi-Chaetomugilin A, 711. C23H29ClO4 – Chaetomugilin L, 723. C23H29ClO5 – Chaetomugilin K, 722. C23H31Br2NO4 – Gymnastatin I, 238.

355

356

Index 2 Compound Molecular Formula Index

C23H31Cl2NO4 – Gymnastatin A, 233. C23H34ClNO5 – Gymnastatin D, 236. – Gymnastatin E, 237. C23H34O5 – Cylindrocarpol, 302. C23H34O6 – Pterocidin, 155. C24 C24H10Br6O6 – Cadiolide B, 583. C24H11Br5O6 – Cadiolide E, 584. C24H14Br4O6 – Cadiolide G, 585. C24H14O11 – Fucofuroeckol A, 552. C24H16O12 – 2-Phloroeckol, 555. – 7-Phloroeckol, 556. C24H16O13 – Diphlorethohydroxycarmalol, 549. C24H18O8 – Caffeoylate ester, 656. C24H18O12 – Fucodiphlorethol G, 551. C24H19NO7 – 5,7-Dihydroxy-2-[[1-(4-methoxy2-oxo-2H-pyran-6-yl)-2phenylethyl]amino]-1,4naphthoquinone, 126. C24H22O7 – δ-Indomycinone, 921. C24H24O7 – Aspernolide A, 23. – (+)-Butyrolactone I, 33. C24H24O8 – (+)-Butyrolactone III, 35. C24H26O8 – Aspernolide B, 24. C24H29ClO6 – Chaetomugilin E, 715. – Chaetomugilin H, 718. C24H29ClO7 – Chaetomugilin B, 712. – Chaetomugilin G, 717.

C24H30O6 – Asperbiphenyl, 688. C24H31ClO7 – Secochaetomugilin D, 741. C24H31ClO8 – Secochaetomugilin A, 740. C24H32O3 – Neurymenolide A, 142. C24H32O4 – Bitungolide F, 100. C24H32O6 – Verrucosidin, 169. C24H34N2O9 – Antibiotic Sg17-1-4, 749. C24H34O4 – Lehualide E, 136. C24H35Br2NO6 – Gymnastatin J, 239. C24H35Cl2NO5 – Gymnastatin B, 234. C24H35N3O8 – Bacilosarcin B, 752. C24H37Br2NO6 – Gymnastatin K, 240. C24H37Cl2NO6 – Gymnastatin C, 235. C24H43NO3 – (4R*,5R*,9S*,10R*,11Z)-4-Methoxy-9((dimethylamino)-methyl)-12, 15-epoxy-11(13)-en-decahydronaphthalen-16ol, 781. C25 C25H12Br6O7 – Cadiolide I, 588. C25H16Br4O6 – (5E)-Cadiolide H, 586. – (5Z)-Cadiolide H, 587. C25H16O9 – Aspergiolide A, 925. C25H26Cl2O5 – Napyradiomycin D, 847. C25H26O4 – 4ʹʹ-Deoxyprenylterphenyllin, 575. C25H26O5 – 4ʹʹ-Deoxyisoterprenin, 574. – 4ʹʹ-Deoxyterprenin, 576. – Prenylterphenyllin, 579.

Index 2 Compound Molecular Formula Index

C25H26O9 – Penilactone A, 666. C25H27BrO5 – Isomarinone, 836. – Marinone, 838. C25H27ClO6 – Emerixanthone A, 415. – Napyradiomycin A, 845. C25H28BrClO5 – Napyradiomycin E, 848. C25H28O5 – Debromomarinone, 829. C25H28O6 – Arugosin A, 454. – Arugosin B, 455. – Hydroxydebromomarinone, 835. C25H28O7 – Napyradiomycin B, 846. C25H29ClO8 – Isochromophilone XI, 696. C25H32Cl2O6 – Napyradiomycin F, 849. C25H32O5 – Tridachiapyrone B, 217. C25H33ClO5 – Bitungolide A, 95. – Bitungolide B, 96. – Bitungolide C, 97. – Bitungolide D, 98. C25H34O4 – Bitungolide E, 99. – Crispatene, 178. – Tridachiapyrone A, 216. C25H34O5 – Crispatone, 179. – Maurapyrone C, 195. – Maurapyrone D, 196. C25H34O6 – Tridachiapyrone D, 218. C25H38O7 – Trichoharzin, 788. C25H42O3 – Flavalactone 2, 44. C25H45NO9 – (+)-Pederin, 86. C26 C26H16O11 – Bacillosporin D‡, 825.

C26H18O10 – Bacillosporin C, 824. C26H18O9 – Aspergiolide B, 926. C26H24O9 – Tetracenoquinocin, 924. C26H26O3 – Aspergilone A, 689. C26H26O11 – Penilactone B, 667. C26H28O8 – Varixanthone, 449. C26H30Cl2O5 – 4a-Dechloro-4,4a-didehydro-antibiotic A 80915A, 844. C26H30O6 – Debromomethoxymarinone, 830. C26H31Cl3O5 – Antibiotic A 80915A, 841. C26H32O5 – Marfuraquinocin A, 792. – Neomarinone, 839. C26H32O6 – Marfuraquinocin C, 793. – Marfuraquinocin D, 794. C26H33Cl3O6 – Antibiotic A 80915C, 842. C26H34Cl2O6 – 4a-Dechloroantibiotic A 80915C, 843. C26H36O3 – Neurymenolide B, 143. C26H36O5 – Maurapyrone A, 194. C27 C27H18O10 – Talaromycesone B, 951. C27H20O10 – Dehydrocitreaglycon A, 940. C27H20O11 – Citreaglycon A, 937. C27H28O12 – Aranciamycin, 923. C27H30O8 – Emerixanthone D, 417. C27H32O7 – Emerixanthone C, 416. C27H33ClO10 – Pestaliopen A, 647.

357

358

Index 2 Compound Molecular Formula Index

C27H33NO9 – Actinoflavoside, 765. C27H34O4 – Tuberatolide B, 79. – 2ʹ-epi-Tuberatolide B, 80. C27H36O4 – Sargafuran, 14. – Sargaquinoic acid, 374. C27H36O5 – Mediterraneol A, 281. C27H44O3 – Flavalactone 3, 45. C27H46O4 – Xestin A, 88. – Xestin B, 89. C28 C28H16O8 – Albopunctatone, 881. C28H16O14 – Vinaxanthone, 450. C28H20O10 – Bacillosporin A, 823. C28H22Br4O7 – Isorawsonol, 378. C28H24O10 – Penicillanthranin A, 702. C28H24O11 – Talaromycesone A, 950. C28H26O5 – Tetraorcinol A, 529. C28H36O4 – Lehualide B, 190. C29 C29H24Br4O7 – Rawsonol, 380. C29H44O4 – Callystatin A, 103. C30 C30H15Br7O12S2 – Crossbyanol B, 545. C30H16N2O12 – Phomopsis H76C, 153. C30H18O10 – 7,7ʹ-Bihelminthosporin, 887. C30H18O14 – Phlorofucofuroeckol A, 557.

– Phlorofucofuroeckol B, 558. C30H20O11 – Hypochromin B, 816. C30H25NO11 – Citreamicin θA, 938. – Citreamicin θB, 939. C30H30O11 – Monodictyochrome A, 663. – Monodictyochrome B, 664. C30H50N2O8 – NSC 646282, 84. C30H50N2O9 – 8-[(2-Oxo-3-piperidinyl)amino]-8-oxooctyl-5,9anhydro-2,3,8-trideoxy-8-(5-hydroxy-4methyl-2-hexenyl)-3-methyl-DL-glycero- LDallo-non-2-enoate, 85. C31 C31H24O10 – Asperpyrone A, 804. – 8ʹ-O-Demethylisonigerone, 808. – 8-O-Demethylnigerone, 809. – Dianhydroaurasperone C, 810. C31H26O11 – Nigerasperone C, 819. C31H36O11 – Kandelisesquilignan A, 770. C31H42O8 – Oscillatoxin D, 243. C31H45NO11 – Irciniastatin B, 762. C31H46O2 – 2-Pentaprenyl-1,4-benzenediol, 283. C31H47NO11 – Irciniastatin A, 761. C32 C32H18Br4O12S2 – Iantheran A, 568. – Isoiantheran A, 570. C32H22Br4O12S2 – Iantheran B, 569. C32H22O10 – Alterporriol Q, 885. C32H22O12 – Antibiotic SC 2051, 803. C32H24Cl4O8 – Chrysophaentin A, 486. – Chrysophaentin F, 488.

Index 2 Compound Molecular Formula Index

C32H24O10 – Antibiotic BE 43472A, 886. C32H24O12 – Hypochromin A, 815. C32H26Cl4O6 – Chrysophaentin E, 487. C32H26O8 – Physcion-10,10′-cis-bianthrone, 871. – Physcion-10,10′-trans-bianthrone, 872. C32H26O10 – Asperpyrone C, 805. – Aurasperone A, 806. – Fonsecinone A, 811. – Isonigerone, 817. – Nigerone, 820. C32H26O11 – Alterporriol K, 882. C32H26O12 – Alterporriol L, 883. – Alterporriol P, 884. C32H28O11 – Fonsecinone B, 812. – Fonsecinone C, 813. – Fonsecinone D, 814. C32H30O12 – Aurasperone B, 807. – Nigerasperone B, 818. C32H38O12 – Kandelisesquilignan B, 771. C32H44O5 – Paecilospirone, 245. C32H44O8 – 30-Methyloscillatoxin D, 242. C32H48O7 – Ilikonapyrone, 186. – Onchitriol I, 198. – Onchitriol II, 203. – Peroniatriol I, 208. – Peroniatriol II, 209. C32H53NO8 – 2-Demethyldiscodermolide, 121. C32H54O7 – 19-Deaminocarbonyldiscodermolide, 119. C32H60O6 – Malyngolide dimer, 138.

C33H28O12 – JBIR 97, 430. – JBIR 98, 431. – JBIR 99, 432. C33H32O10 – Eurorubrin, 865. C33H33NO14 – Arenjimycin, 935. C33H50O7 – Auripyrone A, 172. – Auripyrone B, 173. C33H53NO7 – 9(13)-Cyclodiscodermolide, 113. C33H55NO8 – Discodermolide, 127. – 2-epi-Discodermolide, 128. C33H56O4 – 1,2-Benzenedicarboxylic acid2-Ethyldecyl 2-ethylundecyl ester, 322.

C33 C33H18Br4O14S2 – 8-Carboxy-isoiantheran A, 566.

C35 C35H52Cl2O6 – Nostocyclophane C, 622.

C34 C34H14Br8O9 – Prunolide A, 248. C34H16Br6O9 – Prunolide B, 249. C34H22O9 – Prunolide C, 250. C34H27Br5N4O10 – Lithothamnin A, 509. C34H34O14 – Deacetylphomoxanthone B, 408. – Deacetyl-phomoxanthone C, 409. – Dicerandrol A, 410. – Phomolactonexanthone A, 443. – Phomolactonexanthone B, 444. C34H38Cl2N2O10 – Fijiolide A, 341. C34H50O8 – Onchitriol IIA, 204. C34H52O5 – Lagunapyrone B, 135. C34H54O8 – Deoxyfusapyrone, 182. C34H54O9 – Neofusapyrone, 141. – Fusapyrone, 183.

359

360

Index 2 Compound Molecular Formula Index

C35H52O8 – Onchitriol IIB, 205.

C37H70O17 C37H72N4O5S

C36 C36H22O18 – 6,6ʹ-Bieckol, 544. – Dieckol, 547. C36H36O15 – 12-O-Deacetyl-phomoxanthone A, 407. – Dicerandrol B, 411. – Penexanthone A, 442. C36H52Br4O6 – Cylindrocyclophane AB4, 614. C36H52Cl4O4 – Cylindrocyclophane F4, 619. C36H52Cl4O5 – Cylindrocyclophane C4, 617. C36H52Cl4O6 – Cylindrocyclophane A4, 613. C36H52O5S – Sacrochromenol A sulfate, 673. C36H52O9 – Onchitriol IA, 199. – Onchitriol IID, 207. C36H52O12 – Aquastatin A, 453. C36H53Cl3O6 – Cylindrocyclophane A3, 612. C36H54Cl2O5 – Cylindrocyclophane C2, 616. C36H54Cl2O6 – Cylindrocyclophane A2, 611. – Nostocyclophane D, 623. C36H55ClO6 – Cylindrocyclophane A1, 610. C36H56O4 – Cylindrocyclophane F, 618. C36H56O5 – Cylindrocyclophane C, 615. C36H56O6 – Cylindrocyclophane A, 609. C36H62O4 – Bis(2-ethyldodecyl) phthalate, 323. C36H64O12 – Antibiotic H 668, 221.

C38 C38H38O13 – MK844-mF10, 908. C38H38O14 – Fradimycin B, 901. C38H38O16 – Dicerandrol C, 412. C38H40O15 – Dioxamycin, 897. C38H48O12 – Stromemycin, 479. C38H54Cl4N2O8 – Carbamidocyclophane A, 604. C38H54O10 – Onchitriol IIC, 206. C38H55Cl3N2O8 – Carbamidocyclophane B, 605. C38H56Cl2N2O8 – Carbamidocyclophane C, 606. C38H57ClN2O8 – Carbamidocyclophane D, 607. C38H58N2O8 – Carbamidocyclophane E, 608. C38H58O10 – Marinisporolide A, 241.

C37 C37H54O9 – Onchitriol IB, 200. – Onchitriol IC, 201.

C41 C41H60O5S – Sacrochromenol B sulfate, 674.

C39 C39H42O15 – Fradimycin A, 900. C40H58O10 – Onchitriol ID, 202. C40H66N2O8 – Bistramide C, 227. C40H68N2O8 – Bistramide A, 225. – 39-Oxobistramide K, 244. C40H70N2O8 – Bistramide B, 226. – Bistramide K, 229. C40H77N2O8 – Bistramide D, 228.

Index 2 Compound Molecular Formula Index

C42 C42H26O21 – 2-Phloro-6,6ʹ-bieckol, 554. C42H46O5 – Longithorone A, 372. C42H52O20 – Trioxacarcin A, 873. C42H54O6 – Isopopopolohuanone E, 394. – 5,5ʹ-diepi-Δ3,Δ3ʹ-Popolohuanone E, 395. – Popolohuanone E, 396. C42H54O20 – Trioxacarcin C, 875. C42H54O21 – Trioxacarcin B, 874. C42H64Cl2O11 – Nostocyclophane B, 621. C42H70N2O9 – Bistratene B, 230. C44 C44H72O14 – Didemnaketal A, 231. C46 C46H36O31 – Excoecariphenol D, 769. C46H68O5S – Sacrochromenol C sulfate, 675. C48 C48H30O23 – 2,7ʹ’-Phloroglucinol-6,6ʹ-bieckol, 559. C48H34O24 – Octaphlorethol A, 553. C48H74Cl2O16 – Nostocyclophane A, 620.

361

C48H86O4 – 1,2-Benzenedicarboxylic acid 2,12-diethyl-11methylhexadecyl 2-ethyl-11-methylhexadecyl ester, 321. C52 C52H80Cl2O17 – Spirastrellolide D, 253. C52H81ClO17 – Spirastrellolide A, 251. C52H82O17 – Spirastrellolide E, 254. C52H84O17 – Spirastrellolide B, 252. C52H86O15 – Didemnaketal B, 232. C54 C54H56N6O18 – Lomaiviticin B, 946. C54H82O4 – Coenzyme Q9, 364. C68 C68H80N6O24 – (–)-Lomaiviticin A, 945. C68H82N4O24 – (–)-Lomaiviticin C, 947. C69 C69H84N4O24 – (–)-Lomaiviticin D, 948. C70 C70H86N4O24 – (–)-Lomaiviticin E, 949.

Index 3 Compound Organism Source Index This index lists in alphabetical order all 594 marine organism in Latin names in HAMNP Volume 7, 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 923 of this index, one will know that the Haliclona sp. is a sponge. A Abietinaria sp. 861, 862. Acanthaster planci 319, 661. Acanthella cavernosa 391, 392, 393. Acanthophora spicifera 654. Acanthus ilicifolius 46, 408, 409, 410, 411, 412, 414, 442, 443, 444. Acremonium sp. 271, 272, 302. Acremonium sp. AWA16-1 484. Acropora sp. 352. Actinomyces sp. CNB-984 135. Aegiceras corniculatum 823, 824, 882, 883, 912. Aiolochroia crassa 331. Alternaria niger 91, 92, 144, 145, 146. Alternaria sp. 397, 882, 883, 884, 885, 912. Alternaria sp. JCM9.2 538, 821, 822. Alternaria sp. ZJ-2008003 914. Alternaria tenuis Sg17-1 745, 747, 749. Alteromonas rubra 353, 354, 355. Alteromonas sp. 84, 85. Amaroucium multiplicatum 280. Ampelomyces sp. 289. Annella sp. 57, 147, 326, 403, 702, 832, 833, 851, 876, 917. Anthocidaris crassispina 75, 76, 888, 898, 909. Apiospora montagnei 401. Aplidium californicum 662. Aplidium constellatum 658. Aplidium glabrum 367. Aplidium longithorax 372. Aplidium savignyi 278, 280. Aplidium sp. 278, 279. Aplysina aerophoba 911, 915, 916. Aplysina aerophoba [Syn. Verongia aerophoba] 331. Aplysina archeri 331. Aplysina fistularis fulva 564. Aplysiopsis formosa 120, 170.

Arthrinium sacchari 754. Arthrinium sp. 401, 437. Ascochyta salicorniae 6, 6, 185, 320, 634, 687, 767. Ascochyta sp. NGB4 222. Aspergillus candidus 542, 576, 581. Aspergillus candidus IF10 574, 575, 579. Aspergillus carbonarius WZ-4-11 175, 176, 797, 800, 801, 802, 808, 809, 817, 820. Aspergillus flavipes AIL8 46. Aspergillus flavus 092008 650. Aspergillus flavus C-F-3 132. Aspergillus fumigatus 224. Aspergillus glaucus 871, 872. Aspergillus glaucus HB1-119 925, 926. Aspergillus niger 685. Aspergillus niger EN-13 126, 798, 804, 805, 806, 807, 810, 811, 812, 813, 814, 818, 819. Aspergillus niger JV-33-48 804, 805. Aspergillus niger TC 1629 800. Aspergillus ostianus 01F313 124. Aspergillus ostianus TUF 01F313 36, 37, 108. Aspergillus parasiticus 288, 292. Aspergillus pseudodeflectus 742. Aspergillus sp. 184, 632, 689, 750, 751, 867, 877. Aspergillus sp. 05F16 866. Aspergillus sp. 16-02-1 25, 26, 27, 28, 29, 30, 31, 49, 94, 104, 124, 328. Aspergillus sp. B-F-2 502. Aspergillus sp. CXCTD-06-6a 327. Aspergillus sp. HDf2 75, 76. Aspergillus sp. KY52178 447. Aspergillus sp. MF-93 688. Aspergillus sp. SCSIOW3 270. Aspergillus sp. XS-20090066 491. Aspergillus sydowi 224, 358, 446, 447. Aspergillus sydowi YH11-2 269, 343, 660, 708, 757.

Index 3 Compound Organism Source Index

Aspergillus sydowii 403. Aspergillus sydowii ZSDS1-F6 345, 349, 489, 490, 503, 505. Aspergillus terreus 24, 589. Aspergillus terreus GWQ-48 50, 582, 590. Aspergillus terreus OUCMDZ-1925 64, 65. Aspergillus terreus PT06-2 23, 24, 33, 34, 35, 759. Aspergillus terreus SCSGAF0162 23, 51. Aspergillus tubingensis OY907 81. Aspergillus unguis 459. Aspergillus ustus 094102 631, 743. Aspergillus varians 289, 292. Aspergillus versicolor 438, 439, 440, 504, 505, 506, 507, 529, 655, 742, 906. Aspergillus versicolor EN-7 896. Aspergillus wentii 451, 452. Avicennia marina 91, 92, 144, 145, 146, 413, 428. Avrainvillea longicaulis 376. Avrainvillea rawsonii 378, 380. Axinella cf. corrugata 686. Axinella damicornis 685. B Bacillus pumilus 744, 745, 747. Bacillus sp. 748. Bacillus subtilis B1779 744, 745, 746, 747, 752. Bacillus subtilis TP-B0611 752. Balanoglossus biminiensis 261. Balanoglossus cornosus 262. Bartalinia robillardoides LF550 696. Beauveria bassiana 426, 889. Beauveria felina EN-135 627. Beckerella subcostatum 32. Boodlea composita 304. Botryllus sp. 583. Botryllus tuberatus 78, 79, 80. Botrytis sp. 131. Briareum polyanthes 174. Bruguiera gymnorrhiza 461, 463, 540, 631, 743, 750, 751. Bruguiera sexangula var. rhynchopetala 365. C Callyspongia aerizusa 4. Callyspongia flammea 640, 641, 642. Callyspongia truncata 103.

363

Callyspongia vaginalis 5. Carpophyllum maschalocarpum 549. Carteriospongia foliascens [Syn. Phyllospongia foliascens] 508, 514, 523. Caulerpa racemosa 346, 347. Caulobacter sp. PK654 624. Chaetomium funicola TCF 6040 653, 682, 683. Chaetomium globosum 301, 720, 726, 727, 728, 729. Chaetomium globosum OUPS-T106B-6 709, 710, 711, 712, 714, 715, 716, 717, 718, 719, 721, 722, 723, 724, 725, 740, 741. Chaetomium sp. 404, 405. Chaetomium sp. Gö 100/2 684. Chrysophaeum taylorii 486, 487, 488, 693, 695. Cladiella sp. 529. Cladosporium cladosporioides sp. TF-0380 52. Cladosporium herbarum 4. Codium fragile 760, 763. Colpomenia sinuosa 126, 567. Comantheria briareus 800. Coniothyrium cereal 799, 934. Coniothyrium cereale 779, 789, 790, 795, 927, 928, 929, 930, 933. Coniothyrium sp. 339. cordyceps sp. BCC1861 490. Corollospora maritima 636. Corynespora cassiicola L36 456. Cosmospora sp. SF-5060 453. Curvularia eschscholzii 130. Curvularia sp. 768 654. Cyerce cristallina 114, 115, 116, 117, 118, 180, 181. Cylindrospermum licheniforme ATCC 29204 609, 615. Cylindrospermum licheniforme ATCC 29412 618. Cymopolia barbata 398, 399, 400. Cystoseira mediterranea 281. Cytospora sp. 312, 637. D Dactylospongia elegans 370, 371. Dakaria subovoidea 889, 941, 942. Daldinia eschscholzii KT32 130. Darwinella rosacea 84, 85. Delisea fimbriata 18, 19, 20. Dendrilla sp. 745, 747.

364

Index 3 Compound Organism Source Index

Dendryphiella salina 365. Diaporthe sp. HLY2 638. Dichotella gemmacea 689. Dictyonella incisa 16. Dictyopteris undulata 659. Didemnum albopunctatum 881. Didemnum sp. 231, 232. Discodermia dissoluta 127. Discodermia sp. 113, 119, 121, 128. Dolabella auricularia 172, 173. Dothiorella sp. 694. Dysidea chlorea 527. Dysidea dendyi 510, 511, 512, 519, 520, 521. Dysidea granulosa 492, 493. Dysidea herbacea 497, 498, 508, 514, 515, 523, 526, 527, 528, 530, 531, 532, 533. Dysidea sp. 268, 394, 395, 396, 494, 499, 500, 501, 516. Dysidea spp. 528. E Echinogorgia praelonga 7. Ecklonia cava 544, 547, 551, 556, 557, 559. Ecklonia kurome 544, 547, 550, 554, 555, 557. Ecklonia maxima 284, 546, 548, 550. Ecklonia stolonifera 284, 547, 548, 550, 556, 557. Ecteinascidia turbinata 935. Ectyoplasia ferox 339. Eisenia arborea 544, 548, 550, 558. Eisenia bicyclis 284, 547, 548, 550, 552, 556, 557. Elysia crispata [Syn. Tridachia crispate] 178, 179, 216, 217, 218. Elysia timida 210. Emericella nidulans var. acristata 386, 454, 455. Emericella sp. SCSIO 05240 415, 416, 417. Emericella unguis 459. Emericella variecolor 359, 479, 899. Emericella variecolor M75-2 17, 449. Encyothalia cliftonii 265. Engyodontium album DFFSCS021 348, 358, 403, 418, 419, 420, 421, 422, 423, 424, 425, 446, 447, 490, 505. Enhygromxya salina 77. Enteromorpha intestinalis 668, 669, 670, 671, 860.

Enteromorpha sp. 779, 789, 790, 795, 927, 928, 929, 933. Enteromorpha tubulosa 132. Epicoccum sp. 4, 639. Epipolasis sp. 251, 252. Ercolania funerea 139, 181. Euplexaura flava 43, 44, 45. Eurotium rubrum 457, 458, 460, 462, 865, 913. Excoecaria agallocha 153, 316, 491, 769, 796. Exophiala sp. 22, 93, 106, 107, 809. F Fenestraspongia sp. 371. Fischerella ambigua 481, 482, 483. Fucus distichus 561, 562, 563. Fucus sp. 177. Fucus vesiculosus 639. Fusarium sp. FH-146 141, 182, 183. Fusarium sp. O5F13 877. Fusarium sp. PSU-F135 791, 851. Fusarium sp. PSU-F14 876, 877. Fusarium sp. ZH-210 866, 867. Fusarium spp. 832, 833, 851, 876. Fusarium spp. PSU-F135 837, 852, 855. Fusarium spp. PSU-F14 868, 869, 870, 880. Fusarium tricinctum 101, 102, 105. G Garveia annulata (order Anthoathecata) 826, 827, 828. Geodia cydonium 401, 437. Gloiopeitis tenax 289, 292, 361, 362. Gracilaria sp. 130. Grateloupia elliptica 262, 263, 266. Grateloupia elliptica and many marine algae 262. Guignardia sp. 4382 197, 219, 888, 889, 890, 891, 892, 893, 894, 895, 898, 905, 907, 910, 918, 919. Gymnascella dankaliensis 233, 234, 235, 236, 237, 238, 239, 240. Gymnogongrus flabelliformis 451, 452. H Halichondria japonica 233, 234, 235, 236, 237. Halichondria okadai 47, 129. Halichondria panicea 106, 107. Haliclona sp. 923, 924. Haliclona valliculata 479, 899.

Index 3 Compound Organism Source Index

Halimeda monile 163, 165, 166, 167. Halimeda opuntia 906. Halimeda spp. 300. Halorosellinia oceanica BCC5149 633, 753. Halorosellinia sp. 1403 888, 889, 890, 891, 891, 892, 893, 893, 894, 895, 898, 905, 907, 910, 910, 918, 919. Hibiscus tiliaceus 342, 457, 460, 462, 650, 865, 913. Hippocampus Kuda 321, 322, 323. Hippospongia metachromia 370. Hippospongia sp. 370, 371. Hormothamnion enteromorphoides 695. Hyalosiphonia caespitosa 131. Hyatella spp. 370. Hymeniacidon hauraki 16. Hypocrea vinosa AY380904 803, 815, 816. Hypoxylon spp. 753. Hyrtios sp. 371. I Ianthella quadrangulata 566, 570. Ianthella sp. 331, 568, 569. Ircinia cf. ramosa 761, 762. Ircinia sp. 283. Ircinia spinosula 673. Isaria felina 665. Ishige foliacea 553. Ishige okamurae 549. J Jaspis sp. 335, 336. K Kandelia candel 197, 219, 246, 247, 330, 573, 577, 578, 690, 697, 834. Kandelia obovata 770, 771. Keissleriella sp. YS4108 780. Kirschsteiniothelia maritima 320. L Laguncularia racemosa 656. Lamellodysidea herbacea 534, 535. Laminaria japonica 324. Landsburgia quercifolia 831. Laurencia similis 389, 524, 785, 786, 787. Laurencia sp. 149. Laurencia spectabilis 10. Lenormandia prolifera 291.

365

Leptolyngbya crossbyana 48, 545. Leptolyngbya sp. 220. Leptosphaeria obiones 856. Leptosphaeria oraemaris 857. Leptosphaeria sp. KTC 727 633. Leucostoma persoonii 312, 637, 692. Lissoclinum bistratum 225, 226, 227, 228, 229, 230. Lissoclinum patella 53. Lithothamnion fragilissimum 509. Lomentaria catenata 303, 305, 691, 864. Lumnitzera racemosa 333, 334. Lyngbya majuscula 137, 138, 168, 189, 242, 859. M Marinactinospora thermotolerans 192, 193. Marinispora sp. CNQ-140 241. Micrococcus luteus 537. Micromonospora lomaivitiensis LL-37I366 945, 946. Microsphaeropsis olivacea 543. Microsphaeropsis sp. 911, 915, 916. Microsphaeropsis sp. 7820 513. Microsporum sp. 303, 305, 691, 864. Monodictys putredinis 435, 663, 664. Monodictys putredinis 187/195 15 I 388, 433, 434, 436. Monodictys sp. 888, 898, 909. Mugil cephalus 224, 709, 710, 711, 712, 714, 715, 716, 717, 720, 726, 727, 728, 729, 740, 741. Muricella abnormalis 309. Mycale adhaerens 758. Mycale cecilia 788. Myceliophthora lutea 628. Mytilus coruscus 931, 932. Myxilla incrustans 543. N Neopilema nomurai 644, 645, 646. Neosartorya fischeri 1008F1 325, 402. Neurymenia fraxinifolia 142, 143. Nigrospora sp. 879. Nigrospora sp. 1403 878. Nigrospora sp. PSU-F12 326. Nigrospora sp. PSU-F18 147, 151, 162. Nigrospora sp. PSU-F5 133. Nocardia sp. ALAA 2000 360. Nocardia sp. KMM 3749 364. Nocardiopsis sp. CNS-653 341.

366

Index 3 Compound Organism Source Index

Nodulisporium sp. CRI247-01 87. Nodulisporium sp. CRIF 1 54, 55, 56. Nostoc linckia UTEX B1932 620, 621, 622, 623. Nostoc sp. CAVN 10 604, 605, 606, 607, 608. Nostoc sp. UIC 10022A 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619. Notheia anomala 8, 9. O Occurs in higher plants 325. Occurs in lichens, e.g. Parmelia spp., and higher plants 912. Occurs in marine algae, fishes, molluscs and crustaceans, such as green alga Ulva lactuca 261. Occurs in molluscs and crustaceans 262. Occurs in plants 766, 888. Oceanibulbus indolifex HEL-4 308. Odonthalia corymbifera 285, 291, 536. Odonthalia spp. 291. Ohchidium sp. 198. Onchidium sp. 199, 200, 201, 202, 203, 204, 205, 206, 207. Onchidium verraculatum 186. Oscillatoria nigroviridis 242, 243. Oscillatoria sp. 109, 110, 111, 112. Oscillatoria spongeliae 527. P Padina australis 260. Paecilomyces lilacinus 152. Paecilomyces sp. 245. Paecilomyces sp. Tree1-7 441. Paecilomyces variotii 644, 645, 646. Paederus fuscipes 86. Penicillium afacidum 681. Penicillium aurantiogriseum 169. Penicillium chermesinum 573, 577, 578. Penicillium chrysogenum 38. Penicillium chrysogenum QEN-24S 149. Penicillium citrinum 702, 703, 784. Penicillium commune 518 309, 310, 311. Penicillium commune QSD-17 730, 731, 732, 733, 734, 735. Penicillium crustosum PRB-2 666, 667. Penicillium dipodomyicola 150, 379. Penicillium expansum 491. Penicillium glabrum 450. Penicillium griseofulvum Y19-07 333, 334.

Penicillium multicolor 738, 739. Penicillium oxalicum 0312f1 337. Penicillium pinophilum 706, 707. Penicillium purpurogenum 461. Penicillium purpurogenum JS03-21 448, 648, 736, 737. Penicillium raistrickii 698, 699, 700, 701. Penicillium sclerotiorum 738, 739. Penicillium sp. 39, 40, 41, 42, 461, 461, 463, 657, 931, 932. Penicillium sp. BM923 756. Penicillium sp. GT200261505 834. Penicillium sp. HKI GT20022605 246, 247. Penicillium sp. JP-1 823, 824. Penicillium sp. M207142 315. Penicillium sp. MA-37 387, 480. Penicillium sp. MFA446 267, 306, 343. Penicillium sp. OUPS-79 668, 669, 670, 671, 860. Penicillium sp. PSU-F44 57. Penicillium sp. ZZF 32 414. Penicillium terrestre 282, 290, 293, 294, 295, 296, 368, 369, 381, 382, 383, 384. Penicillium thomi 540. Penicillium waksmanii 156, 157. Penicillium waksmanii OUPS-N133 158. Perithalia capillaris 264, 366. Perithalia caudata 264. Peronia peronia 208, 209. Pestalotia sp. 390. Pestalotiopsis sp. 58, 304, 517, 518, 647. Pestalotiopsis sp. JCM2A4 672. Pestalotiopsis sp. ZJ-2009-7-6 704, 705. Pestalotiopsis vaccinii 772. Petriella sp. TUBS 7961 125. Petrosaspongia metachromia 370. Phaeobacter gallaciensis DSM17395 625. Phialocephala sp. 629. Phoma herbarum 289, 292, 361, 362. Phomopsis sp. 407, 408, 409, 410, 411, 412, 413, 428, 442, 443, 444, 783. Phomopsis sp. hzla01-1 626. Phomopsis sp. ZSU-H26 796. Phomopsis sp. ZSU-H76 153, 316. Phoronopsis viridis 261, 266. Phyllospongia dendyi 485, 495, 496, 525. Phyllospongia foliascens 508, 514, 523. Phyllospongia foliascens [Syn. Carteriospongia foliascens] 508, 514, 523.

Index 3 Compound Organism Source Index

Pinna attenuata 223. Pinna muricata 211. Placida dendritica 187, 188, 212, 213. Placobranchus ocellatus 210. Plakinastrella mamillaris 59. Plakortis simplex 12, 13, 60, 62, 63, 66, 67, 68, 69, 70, 71, 72, 73, 74, 160, 161. Plakortis sp. 61, 136, 190, 191. Plakortis sp. (subclass Homoscleromorpha, order Homosclerophorida, famiily Plakinidae) 61. Poecillastra wondoensis 336. Polyandrocarpa zorritensis 332. Polyfibrospongia australis 370. Polyopes lancifolia 285. Polyporales sp. 214, 215. Polysiphonia elongata 297. Polysiphonia lanosa 297. Polysiphonia spp. 291. Polysiphonia urceolata 301. Pongamia pinnata 768. Psammaplysilla purpurea 331. Psammocinia aff. bulbosa 761. Pseudoalteromonas luteoviolacea 260. Pseudoceratina crassa 340. Pseudoceratina purpurea 430, 431, 432. Pseudoceratina sp. 338. Pseudodistoma antinboja 583, 584. Pseudomonas sp. F92S91 154. Ptychodera flava laysanica 266. Ptychodera sp. 262. R Reniera mucosa 571, 572. Rhizophora mucronata 304, 407, 647, 672. Rhizophora apiculata 58, 517, 518. Rhizophora mangle 312, 637, 692. Rhodomela confervoides 286, 299, 377, 385. Rhodomela larix 385. Rhodomela spp. 285, 291. Rhodomela subfusca 297. Ritterella rubra 591, 592, 593, 594, 595, 596, 597, 598. Rosenvingea sp. 390. S Salegentibacter sp. T436 365. Salinispora arenicola 935.

367

Salinispora arenicola CNS-325 922. Salinispora pacifica 3, 947, 948, 949. Salinispora pacifica CNS-237 159. Salinispora tropica CNB-392 1, 2. Sarcophyton crassocaule 373. Sarcophyton sp. 884, 914. Sarcophyton sp. ZJ-2008003 885. Sarcotragus spinulosus 673, 674, 675. Sargassum macrocarpum 14. Sargassum patens 560. Sargassum ringgoldianum 101, 102, 105, 158. Sargassum serratifolium 374. Sargassum thunbergii 896. Schizothrix calcicola 242, 243. Serinicoccus sp. 840. Sinularia kavarattiensis 24. Sinularia sp. 781. Siphonaria diemenensis 122, 123. Siphonaria grisea 148. Siphonaria maura 194, 195, 196. Siphonaria pectinata 134, 148. Smenospongia sp. 375. Smenospongia spp. 370. Spicaria elegans KLA-03 539. Spirastrella coccinea 251, 252, 253, 254. Spirastrella vagabunda 317. Spiromastix sp. MCCC 3A00308 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478. Spongia sp. 283, 370. Sporochnus comosus 264, 273, 274, 275, 276, 277, 366. Sporochnus pedunculatus 264. Stachybotrys sp. HH1 ZSDS1F1-2 427, 437, 445. Stachylidium sp. 640, 641, 642. Stagonospora spp. 857. Stelletta sp. 302. Stemphylium radicinum 6. Sterile mycelium 760, 763. Streptomyces caelestis 937, 938, 939, 940. Streptomyces chibaensis AUBN1/7 943. Streptomyces exfoliates 850. Streptomyces fradiae PTZ00025 897, 900, 901, 908. Streptomyces hygroscopicus TP-A0451 155. Streptomyces niveus 792, 793, 794. Streptomyces sp. 155, 356, 357, 765, 863, 920, 921, 923, 924.

368

Index 3 Compound Organism Source Index

Streptomyces sp. B8300 921. Streptomyces sp. B8335 782. Streptomyces sp. B8652 873, 874, 875. Streptomyces sp. BD-18T 853, 854, 903, 904. Streptomyces sp. CNH-070 849. Streptomyces sp. CNQ-329 845, 846, 847, 848. Streptomyces sp. H668 221. Streptomyces sp. M02750 21. Streptomyces sp. M268 944. Streptomyces sp. N1-78-1 886. Streptomyces sp. NPS-554 350, 351. Streptomyces sp. NTK 227 90. Streptomyces spinoverrucosus 902. Streptomyces sundarbansensis 177. Streptomyces xiamenensis 679, 680. Stylinos sp. 83. Stylotella sp. 140. Suberea mollis 338. Suberea sp. 338. Suberites domuncula 125. Symbiodinium spp. 82. Symphyocladia latiuscula 285, 287, 297, 298, 307, 565. Synechocystis sp. 352. Synoicum blochmanni 591, 592, 593, 595, 599, 600, 601, 602. Synoicum globosum 595, 596. Synoicum prunum 248, 249, 250, 591. Synoicum sp. 585, 586, 587, 588, 603. T Talaromyces bacillisporus SBE-14 823, 824, 825. Talaromyces sp. 690. Talaromyces sp. LF458 950, 951. Talaromyces sp. SBE-14 330. Talaromyces sp. ZH-154 697. Tedania ignis 522, 541. Terrestrial and marine-derived Aspergillus terreus 33. Terrestrial and marine-derived fungus Aspergillus sydowi 358. Terrestrial Aspergillus sp. Y80118 402. Terrestrial Dicerandra frutescens 410, 411, 412. Terrestrial fungi Ascochyta spp. 687. Terrestrial fungi Aspergillus spp. 93, 802, 806, 807. Terrestrial fungi Cortinarius spp. 891.

Terrestrial fungi Fusarium acuminatum and Fusarium chlamydosporum 105. Terrestrial fungi Gremmeniella abietina and Roesleria hypogeal 934. Terrestrial fungi Penicillium spp. 643. Terrestrial fungi Penicillium verrucosum var. cyclopium and Penicillium variabile 169. Terrestrial fungi toadstools Cortinarius toadstools and Dermocybe splendid 876. Terrestrial fungus Aspergillus candidus 580, 581. Terrestrial fungus Aspergillus carbonarius 811. Terrestrial fungus Aspergillus fonsecaeus 811, 812, 813. Terrestrial fungus Aspergillus fonsecaeus and Aspergillus niger 814. Terrestrial fungus Aspergillus niger 810, 817, 820. Terrestrial fungus Aspergillus ochraceus 124. Terrestrial fungus Aspergillus terreus 582. Terrestrial fungus Aspergillus ustus 743. Terrestrial fungus Chaetomium globosum 709, 714. Terrestrial fungus Epicoccum purpurascens MYC 1097 639. Terrestrial fungus Gremmeniella abietina 799. Terrestrial fungus Penicillium sp. 442. Terrestrial fungus Phomopsis longicolla 410, 411, 412. Terrestrial fungus Phomopsis sp. PSU-D15 408. Terrestrial fungus Talaromyces flavus 649. Terrestrial lichens 590. Terrestrial plant pea Pisum sativum 743. Terrestrial plant Rubia cordifolia 893. Terrestrial plants 898. Terrestrial plants Aspergillus niger in infected mango fruits and peanuts 802. Terrestrial plants, family Leguminosae spp. and Papilionoideae spp. 767. Terrestrial plants, Rheum palmatum, Xyris semifuscata, Cinchona ledgeriana and Pyrrhalta luteola 889. Terrestrial streptomycetes Streptomyces echinatus and Streptomyces chromofuscus 923. Terrestrial streptomycetes Streptomyces ochraceus and Streptomyces bottropensis 873, 874, 875.

Index 3 Compound Organism Source Index

Terrestrial unidentified plant 426. Tethya aurantium 38, 696. Thalassia hemprichii 214, 215. Thalassia testudinum 764. Thelepus setosus 630. Theonella cf. swinhoei 95, 96, 97, 98, 99, 100. Thermovibrio ammonificans 651, 652. Thespesia populnea 766. Tolypothrix sp. 189. Trichoderma aureoviride PSU-F95 917. Trichoderma harzianum 788. Trichoderma harzianum OUPS-N115 47, 129. Trichoderma reesei 676, 677, 678. Trichoderma sp. 319, 661. Trichoderma sp. f-13 313, 318. Tridachia crispata [Syn. Elysia crispata) 178, 179, 216, 217, 218. Trididemnum cyclops 225, 228, 244. Tritirachium sp. 430, 431, 432. U Ulocladium botrytis 5, 543. Ulva fasciata 706, 707. Ulva lactate 266. Ulva pertusa 267, 306, 343. Ulva sp. 6, 185, 320, 634, 657, 687, 767. Unidentified alga 404, 405, 749, 867, 877. Unidentified algae 649, 755. Unidentified fungus IFM 52672 87. Unidentified gorgonian 310, 311. Unidentified green alga 386, 454, 455. Unidentified jellyfish 459. Unidentified mangrove 441, 582, 589, 590, 783, 866, 867. Unidentified mangrove-derived fungi 1839 and dz17 753. Unidentified mangrove-derived fungus 329. Unidentified mangrove-derived fungus 2240 887. Unidentified mangrove-derived fungus 2526 912. Unidentified mangrove-derived fungus k38 171. Unidentified marine alga 684. Unidentified marine fungi E3 and K38 310, 311, 314. Unidentified marine fungi E33 and K38 429. Unidentified marine fungus 164, 739.

369

Unidentified marine fungus (order Pleosporales) 358. Unidentified marine origin 626. Unidentified marine-derived actinomycete CNB-632 829, 838. Unidentified marine-derived actinomycete CNH-099 830, 835, 836, 838, 839. Unidentified marine-derived actinomycete CNQ-525 841, 842, 843, 844. Unidentified marine-derived fungus 140, 163, 167, 363, 649, 755, 773, 774, 775, 776, 777, 778. Unidentified marine-derived fungus (phylum Ascomycota, order Pleosporales) 773, 774, 775, 776, 777, 778. Unidentified marine-derived fungus 951014 317. Unidentified marine-derived fungus CNC-159 165, 166. Unidentified marine-derived fungus CRIF2 (order Pleosporales) 635. Unidentified marine-derived fungus I96S215 52. Unidentified marine-derived fungus LL-37H248 255, 256, 257, 258, 259. Unidentified mollusc 459. Unidentified sea anemone 878, 879. Unidentified soft coral 255, 256, 257, 258, 259, 356, 357, 704, 705. Unidentified sponge 36, 37, 52, 108, 124, 426, 635, 754, 858, 889. Urechis unicinctus 888. V Verongia aerophoba [Syn. Aplysina aerophoba] 331. Verongula rigida 331. W Wardomyces anomalus 401, 437. Watersipora subtorquata 889, 936. X Xestospongia exigua 655, 742. Xestospongia sp. 88, 89, 537. Xestospongia testudinaria 11, 15. Z Zostera marina 344.

Index 4 Compound Sampling Geographic Locality Index In this index, all geographic locations in HAMNP Volume 7 have been devided as 17 large areas: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

CHINA JAPAN RUSSIA KOREA WATERS R. O. KOREA ASIA AUSTRALIA OCEANIA EUROPE AFRICA USA NORTH AMERICA CARIBBEAN SEA SOUTH AMERICA PACIFIC OCEAN ATLANTIC OCEAN ANTARCTIC/ARCTIC

For all 147 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” books and a number code sequence of the related compounds follows the detail information immediately. There are 555 related compounds with geographic information in HAMNP Volume 7. 1 CHINA China, Bohai Bay, Shandong 698, 699, 700, 701. China, Bohai Sea 169. China, Bohai Sea, Tianjin 397. China, China waters 126, 132, 153, 223, 246, 247, 282, 290, 293, 294, 295, 296, 301, 304, 316, 318, 329, 381, 382, 383, 384, 414, 460, 462, 502, 540, 676, 677, 678, 743, 749, 769, 796, 797, 800, 801, 802, 808, 809, 817, 820, 823, 824, 834, 913, 925, 926. China, Danzhou, Hainan 309. China, Dongzhai of South China Sea coast 428. China, Dongzhai, Hainan 91, 92, 144, 145, 146, 413. China, Fujian 313, 582, 589, 590. China, Guangdong 882, 883, 912. China, Hainan Sanya National Coral Reef Reserve 319, 661. China, Hainan 408, 409, 410, 411, 412, 442, 443, 457, 461, 463, 647, 672, 865.

China, Hainan, South China Sea 444. China, Jiaozhou Bay, Shandong 224. China, Kiaochow Bay, Qingdao 863. China, Lanqi I., Fujian 703. China, Lingao, Hainan 529. China, Lingshui Bay, Hainan 373. China, Lujiang River, Yunnan 448. China, Pingtan I., Fujian 451, 452. China, Qi’ao I., Zhuhai, Guangdong 690, 697. China, Qingdao, Shandong 896, 944. China, Qionghai, Hainan 75, 76. China, Quang-Zhou Gulf 688. China, region of red soil by Lujiang River, Yunnan 648, 736, 737. China, Sanya, Hainan 11. China, South China Sea, Guangdong 573, 577, 578. China, Weizhou coral reef, Guangxi 884, 885, 914. China, Weizhou I., Guangxi 149, 356, 357, 879.

Index 4 Compound Sampling Geographic Locality Index

China, Wenchang, Hainan 631, 650. China, Ximen I., Zhejiang 770, 771. China, Zhanjiang coastline 346, 347. Hong Kong, Hong Kong 330, 891, 893, 910. South China Sea, open voyage to South China Sea 415, 416, 417. South China Sea, South China Sea 750, 751, 171, 192, 193, 197, 219, 689, 730, 731, 732, 733, 734, 735, 792, 793, 794, 912. South China Sea, Yongxing I., South China Sea, China 12, 60, 62, 63, 66, 67, 68, 69, 70, 71, 72, 73, 74. Taiwan, Taiwan waters 13, 441. Yellow Sea 506, 507. Yellow Sea, near Sheyang Port 780. 2 JAPAN Japan, Atami-shi, Shizuoka 754. Japan, Japan waters 14, 103, 141, 182, 183, 335, 336, 484, 574, 575, 576, 579, 649, 755, 760, 763, 888, 889, 898, 909, 941, 942. Japan, Katsuura Bay 224, 709, 710, 711, 712, 714, 715, 716, 717, 720, 726, 727, 728, 729. Japan, Miyazaki Harbor 350, 351. Japan, Nagannu I., Japan, East China Sea 251, 252. Japan, off shore Japan 756. Japan, Otsuchi Bay 155. Japan, Tateyama City, Chiba 923, 924. Okinawa, Iriomote I. 426, 889. Okinawa, Okinawa 7, 211, 352, 815, 816, 931, 932. Okinawa, Sakuraguchi, Ishigaki I. 430, 431, 432. Tokyo, Kasai 706, 707. 3 RUSSIA Kuril Is., Kuril and Simushir Is., Sea of Okhotsk 364. Sea of Okhotsk, Russia Sakhalin Bay, Sea of Okhotsk 504. 4 KOREA WATERS Korea waters, 21, 106, 107, 131, 267, 302, 303, 305, 306, 343, 691, 864. 5 R. O. KOREA Cheokpo Cheokpo, Tongnyeong 289, 292, 361, 362. Chuja-do Chuja-do 585, 586, 587, 588.

371

GeoMun I. GeoMun I., Yeosu 101, 102, 105. Jeju I. Jeju I. 553, 559. Southern coast Southern coast of R. O. Korea 644, 645, 646. Tong-Yeong City 78, 79, 80, 583, 584. 6 ASIA India waters 24. Indonesia 130, 867, 877. Indonesia along Lembeh Strait off Bitung, Sulawesi I. 95, 96, 97, 98, 99, 100. Indonesia Mengangan I., Bali 655. Indonesia Muara Angke, Jakarta 407. Indonesia South Sulawesi coast 130. Indonesia West Sumatra 530, 531, 532, 533. Indo-Pacific Sea Indo-Pacific 268, 317, 494, 499, 500, 501, 516, 537. Red Sea 567, 744, 745, 746, 747, 752. Saudi Arabia Jiddah 937, 938, 939, 940. Thailand 57, 326, 635, 753. Thailand Koh Hin Ran Pet, Surat Thani province 832, 833, 851, 876. Thailand location unspecified, presumably Thailand 214, 215. Thailand Satun province 58, 517, 518. Thailand Similan Is., Phangnga 147, 702, 917. Thailand Surat Thani province 403. Vietnam 665. 7 AUSTRALIA Australia 122, 123, 248, 249, 250, 265, 283, 370, 497, 508, 514, 523, 528, 566, 568, 570, 591. Australia Sydney 640, 641, 642. Great Barrier Reef, Australia Bowden Reef 781. Great Barrier Reef, 569. Great Barrier Reef, Australia Swain Reefs 881. Northwestern Australia North West coast of Australia 519. Queensland Shaw I. 264, 273, 274, 275, 276, 277, 366. Southern Australia 9. 8 OCEANIA Federated States of Micronesia Pohnpei I. 36, 37, 108, 124, 396, 783. Federated States of Micronesia Yap 245. Fiji 3, 59, 226, 227, 228, 229, 391, 392, 393, 523.

372

Index 4 Compound Sampling Geographic Locality Index

Fiji Taveuni I. 142, 143. Fiji Vim Levu 534, 535. New Zealand 16, 394, 395, 765. Palau, Oceania 231, 232, 370, 371, 485, 495, 496, 498, 508, 514, 515, 523, 525, 526, 527, 922. Palau, Oceania Lighthouse Reef, Palau Is. 509. Papua New Guinea Milne Bay 492, 493. Vanuatu 338. 9 EUROPE Adriatic Sea, Croatia Limski Channel, Adriatic Sea, Croatia 38. Adriatic Sea, Italy Adriatic Sea 401, 437. Baltic Sea, Germany Baltic coast, Germany 773, 774, 775, 776, 777, 778. Baltic Sea, Germany Fehmarn I., Germany 779, 789, 790, 795, 927, 928, 929, 933. Germany Prerow I. 77. Greece waters 404, 405. Mediterranean Sea 16, 125, 139, 210, 386, 454, 455, 911, 915, 916. Mediterranean Sea Bay of Taranto 332. North Sea 39, 40, 41, 42. Portugal Azores Is. 120, 170. Spain 278, 279, 599, 600, 601, 602. Spain Cádiz 134, 148. 10 AFRICA Algeria Bejaia 177. Egypt Hurghada 338. Egypt Rass Mohamed, south Sinai 906. Egypt Suez Canal 657. Madagascar 168, 244. South Africa Algoa Bay 595, 596. 11 USA Alaska, USA 561, 562, 563. California, USA Batiquitos Lagoon, North of San Diego 830, 835, 836, 838, 839. California, USA La Jolla 241. California, USA San Diego 845, 846, 847, 848. California, USA San Elijo Lagoon, Encinitas 849. California, USA Southern California 135. Florida, USA Everglades 312, 637, 692. Florida, USA Florida Keys 399. Guam, USA 269, 343, 654, 660, 708, 757, 859.

Hawaii, USA 260. Hawaii, USA Honaunau Reef 48, 545. Oregon, USA 10. Puerto Rico 695. Texas, USA Trinity Bay, Galveston 902. USDA Agricultural Research Service 947, 948, 949. 12 NORTH AMERICA Canada Vancouver I. 255, 256, 257, 258, 259. Gulf of Mexico Lagoon 921. Panama Coiba National Park 109, 110, 111, 112, 138. 13 CARIBBEAN SEA Bahamas a salt lake in Bahamas 910. Bahamas Caribbean Sea 113, 119, 121, 128, 390, 891, 893. Bahamas Sweeting Cay, Grand Bahama I. 935. Bahamas Sweetings Cay 522, 541. Caribbean Sea 160, 161. Curacao I., Caribbean Sea 189. Grand Bahama I. off Grand Bahama I., Caribbean 127. Jamaica 61. 14 SOUTH AMERICA Venezuela 459. 15 PACIFIC OCEAN East Pacific Ocean 629, 679, 680. East Pacific Ocean hydrothermal vent, East Pacific Rise 651, 652. Lau Basin hydrothermal vent 25, 26, 27, 28, 29, 30, 31, 49, 94, 104, 124. New Caledoinia (Fr.) 199, 200, 201, 202, 204, 205, 206, 207, 226, 227, 228, 229, 283. Northeastern Pacific Ocean 826, 827, 828. Oahu 853, 854, 903, 904. 16 ATLANTIC OCEAN South Atlantic Ocean 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478. 17 ANTARCTIC/ARCTIC Antarctic Antarctic Ocean 666, 667.

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. [±]-Aeroplysinin 1 has a wide spectrum of bioactivities. In preclinical studies, it has been shown to have promising antiinflammatory, anti-angiogenic and antitumor effects. It might have a pharmaceutical interest for different pathologies 331. 3α-Hydroxysteroid dehydrogenase inhibitor 246, 247, 834. 15-Lipoxygenase inhibitor 268, 494, 499, 500, 501, 516. 20S-proteasome inhibitor 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619. 20S-Proteasome inhibitor, chymotrypsinlike 3. A A lead for Alzheimer’s disease therapy 374. A lead for anti-obesity drug 220. Acaricide 744. Acetylcholinesterase inhibitor 573, 950, 951. AChE inhibitor 11, 441. active against Clostridium welchii 437. Adenosine triphosphatases inhibitor, mammalian 453. Algicide, green alga Dunaliella sp. 165. Anti-acne prevent or improve propionibacterium acne 14. Anti-AD, preclinical trial, GSK3β mediated by JNK pathway, animal model, 3xTg-AD mice, effect, GSK3β inhibition τ phosphorylation reduction 850. Antialgal, green alga Chlorella fusca 386. Antialgal, green alga Dunaliella sp. 163, 164, 166, 167. Anti-allergic phlorotannins 558. Antiangiogenic 754, 936. Anti-angiogenic, BAEC 331. Anti-angiogenic, BAEC Cell Line, target MMP-2, effect decrease 331.

Anti-angiogenic, BAEC Cell Line, target PA, effect decrease 331. Anti-angiogenic, BAEC Cell Line, target PAI, effect increase 331. Anti-angiogenic, EVLC-2 331. Anti-angiogenic, EVLC-2 Cell Line, target MMP-2, effect decrease 331. Anti-angiogenic, HMEC 331. Anti-angiogenic, HUVEC 331. Anti-angiogenic, HUVEC Cell Line, target MMP-2, effect decrease 331. Anti-angiogenic, RF-24 331. Anti-angiogenic, RF-24 Cell Line, target MMP-2, effect decrease 331. Anti-Aβ peptide aggregation inhibition, Aβ42 assembling activity 270. Antibacterial 14, 22, 105, 123, 264, 289, 340, 365, 410, 453, 487, 488, 490, 505, 636, 745, 746, 747, 752, 823, 824, 825, 826, 842, 886. Antibacterial inactive, Bacillus subtilis 730, 731, 733, 735. Antibacterial inactive, Candida albicans 538. Antibacterial inactive, Enterobacter cloacae 538. Antibacterial inactive, Enterococcus faecalis 538. Antibacterial inactive, ESBLs− 12-14 466, 468, 469, 470, 471, 472, 473. Antibacterial inactive, ESBLs− 12-4 466, 468, 469, 470, 471, 472, 473. Antibacterial inactive, ESBLs− 1515 466, 468, 469, 470, 471, 472, 473. Antibacterial inactive, ESBLs− 7 466, 468, 469, 470, 471, 472, 473. Antibacterial inactive, ESBLs− ATCC 25922 466, 468, 469, 470, 472, 473. Antibacterial inactive, ESBLs+ 12-15 466, 468, 469, 470, 471, 472, 473. Antibacterial inactive, ESBLs+ 12-8 466, 468, 469, 470, 471, 472, 473.

374

Index 5 Compound Pharmacological Activity Index

Antibacterial inactive, ESBLs+ ATCC 700603 466, 468, 469, 471, 470, 471, 472, 473. Antibacterial inactive, Escherichia coli ATCC 25922 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478. Antibacterial inactive, MDR Vibrio parahemolyticus 7001 644, 645, 646. Antibacterial inactive, Micrococcus luteus 480, 765. Antibacterial inactive, MRSA 147, 538, 692, 730, 731, 734, 735, 822. Antibacterial inactive, MRSA 12-33 468. Antibacterial inactive, MRSA 3089 644, 646. Antibacterial inactive, MSSA 12-28 468. Antibacterial inactive, NDM-1+ ATCC BAA-2146 466, 468, 469, 470, 471, 472, 473. Antibacterial inactive, Pseudomonas aeruginosa 24, 730, 731, 732, 733, 734, 735. Antibacterial inactive, Pseudomonas aeruginosa ATCC 15442 141, 182, 183. Antibacterial inactive, Pseudomonas fluorescens 730, 731, 732, 735. Antibacterial inactive, Staphylococcus aureus 24, 628, 765, 933. Antibacterial inactive, Staphylococcus aureus ATCC 25923 147. Antibacterial inactive, Staphylococcus aureus NBRC 13276 141, 182, 183. Antibacterial inactive, Staphylococcus aureus SG 511 644. Antibacterial inactive, Staphylococcus pneunoniae 765. Antibacterial inactive, VRE 09-9 466, 470, 468. Antibacterial inactive, VRE 12-1 466, 468. Antibacterial inactive, VRE 12-3 466, 470, 468. Antibacterial inactive, VRE ATCC 51299 466, 470, 468. Antibacterial inactive, VRE ATCC 700221 466, 470, 468. Antibacterial inactive, VSE 12-5 466, 470, 468. Antibacterial inactive, VSE ATCC 29212 466, 470, 468. Antibacterial, Acinetobacter baumannii ATCC 19606 415, 416. Antibacterial, Aeromonas hydrophila ATCC 7966 415, 416.

Antibacterial, Aeromonas hydrophilia 387. Antibacterial, Arthrobacter cristallopoietes 77. Antibacterial, Bacillus cereus 878, 879, 906. Antibacterial, Bacillus megaterium 454, 455, 513. Antibacterial, Bacillus subtilis 4, 46, 122, 148, 317, 320, 348, 358, 394, 395, 403, 424, 425, 449, 504, 626, 650, 655, 696, 732, 734, 744, 750, 751, 838, 853, 854, 874, 878, 903, 904, 906, 909. Antibacterial, Bacillus subtilis 769 937, 938, 939, 940. Antibacterial, Bacillus subtilis ATCC 6051 330. Antibacterial, Bacillus subtilis ATCC 6633 481, 482. Antibacterial, Bacillus subtilis SCSIO BT01 466, 469, 470, 472, 473, 471, 468, 464, 465, 467, 474, 475, 476, 477, 478. Antibacterial, Bacillus thuringiensis SCSIO BT01 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478. Antibacterial, Burkholderia cepacia 260. Antibacterial, Candida albicans 626. Antibacterial, DRS and other gram-positive pathogens 935. Antibacterial, Enterobacter aerogenes 650, 24, 311, 539, 310, 309. Antibacterial, Enterobacter coli 480, 650, 311, 539, 310, 458, 513, 704, 705. Antibacterial, Enterococcus faecalis 449, 647. Antibacterial, Enterococcus faecalis ATCC 29212 415, 416. Antibacterial, Escherichia coli 53, 309, 358, 403, 424, 425, 441, 449, 626, 795, 866, 874, 878, 896, 909. Antibacterial, Escherichia coli ATCC 25922 329. Antibacterial, Escherichia coli ATCC 25922.18 481, 482. Antibacterial, Escherichia coli ATCC 29922 415, 416. Antibacterial, five different bacterial strains 484. Antibacterial, gram-positive and -negative bacteria 360, 584, 585, 586, 587, 588, 624, 687, 873, 875, 943. Antibacterial, gram-positive bacteria 148, 222, 799, 850, 853, 854, 855, 897, 903, 904, 923, 934, 945, 946.

Index 5 Compound Pharmacological Activity Index

Antibacterial, including MRSA 154, 841. Antibacterial, Klebsiella pneumonia 345, 349, 503. Antibacterial, Klebsiella pneumonia ATCC 13883 415, 416. Antibacterial, Loktanella hongkongensis 744. Antibacterial, MDRSA 106, 107, 864. Antibacterial, Microbotryum violaceum 513. Antibacterial, Micrococcus luteus 120, 878, 933. Antibacterial, Micrococcus luteus ATCC 9341 481, 482. Antibacterial, Micrococcus tetragenus 878. Antibacterial, MRSA 106, 107, 142, 143, 260, 312, 390, 538, 545, 583, 637, 702, 732, 733, 821, 845, 846, 851, 852, 864, 869, 876, 917, 922, 950, 951. Antibacterial, MRSA 12-33 466, 469, 470, 472, 473, 471. Antibacterial, MRSA 3089 645. Antibacterial, MRSA ATCC 33591 466, 469, 470, 472, 473, 471, 468. Antibacterial, MRSA ATCC43300 937, 938, 939. Antibacterial, MRSA SK1 57. Antibacterial, MRSA, MMOA: - inhibits GTPase activity of bacterial cell division protein FtsZ, which is a structural homolog of eukaryotic tubulin 486. Antibacterial, MRSAATCC43300 940. Antibacterial, MRSE 793, 794. Antibacterial, MRSE12-8 466, 469, 470, 472, 473, 471, 468. Antibacterial, MSSA 583. Antibacterial, MSSA 12-28 466, 469, 470, 472, 473, 471. Antibacterial, MSSA 15 466, 469, 470, 472, 473, 471, 468. Antibacterial, MSSA ATCC 29213 466, 469, 470, 472, 473, 471, 468. Antibacterial, MSSE ATCC 12228 466, 469, 470, 472, 473, 471, 468. Antibacterial, MSSE12-6 466, 469, 470, 472, 473, 471, 468. Antibacterial, Mycobacterium phlei 933, 779, 795, 928, 929, 930. Antibacterial, Mycobacterium smegmatis 137. Antibacterial, Photobacterium phosphoreum 331.

375

Antibacterial, Pseudomonas aeruginosa 539, 627. Antibacterial, Pseudomonas fluorescens 733, 734. Antibacterial, Pseudomonas putida 491. Antibacterial, Pseudomonas spp 151. Antibacterial, Ruegeria atlantica 36, 37, 108. Antibacterial, Saccharomyces cerevisiae 626. Antibacterial, several gram-positive bacteria 407. Antibacterial, Staphylococcus albus 878. Antibacterial, Staphylococcus aureus 4, 46, 75, 76, 106, 107, 122, 397, 449, 459, 491, 504, 539, 607, 608, 702, 744, 750, 751, 792, 793, 794, 795, 829, 851, 852, 853, 854, 866, 867, 869, 874, 876, 878, 900, 901, 903, 904, 906, 908, 927. Antibacterial, Staphylococcus aureus and MRSA 791. Antibacterial, Staphylococcus aureus ATCC 29213 330, 415, 416, 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478. Antibacterial, Staphylococcus aureus ATCC 6538 604, 605, 606. Antibacterial, Staphylococcus aureus ATCC27154 329. Antibacterial, Staphylococcus aureus SG 511 645, 646. Antibacterial, Staphylococcus aureus UST950701-005 937, 938, 939, 940. Antibacterial, Staphylococcus aureus, three strains 101, 102. Antibacterial, Staphylococcus epidermidis 491, 950, 951. Antibacterial, Staphylococcus epidermis 829. Antibacterial, Staphylococcus Haemolyticus UST950701-004 937, 938, 939, 940. Antibacterial, Staphylococcus lentus 696. Antibacterial, Staphylococcus pneumonia 829. Antibacterial, Staphylococcus pyrogenes 829. Antibacterial, Streptococcus pyogenes 137. Antibacterial, Streptomyces viridochromogenes 874. Antibacterial, temperature-sensitive mutant Bacillus subtilis CNM2000, suggesting ascochytatin inhibited function of YycG/ YycF-TCS in bacterium 222. Antibacterial, Trichophyton spp 151.

376

Index 5 Compound Pharmacological Activity Index

Antibacterial, Vibrio anguillarum 194, 195, 196, 491, 704, 705, 878. Antibacterial, Vibrio parahaemolyticus 704, 705, 878. Antibacterial, Vibrio parahemolyticus 491. Antibacterial, VRE 09-9 469, 471, 472, 473. Antibacterial, VRE 12-1 469, 470, 471, 472, 473. Antibacterial, VRE 12-3 469, 471, 472, 473. Antibacterial, VRE ATCC 51299 469, 471, 472, 473. Antibacterial, VRE ATCC 700221 469, 471, 472, 473. Antibacterial, VREF 142, 143, 390. Antibacterial, VREF, MMOA: - inhibits GTPase activity of bacterial cell division protein FtsZ, which is a structural homolog of eukaryotic tubulin 486. Antibacterial, VSE 12-5 469, 472, 473, 471. Antibacterial, VSE ATCC 29212 469, 472, 473, 471. Antibacterial, Xanthomonas campestris 38. Antibarnacle 921. Antibiotic 18, 19, 20, 177, 297, 783. Antibiotic, broad-spectrum 93. Antibiotic, gram-positive bacteria and several dinoflagellate microalgae causing toxic blooms 331. Anticholinesterase activity of plastoquinones 374. Antidiabetic 553. Antidiabetic and anti-arthrosclerosis, due to its covalent binding to PPARγ, inhibiting adipocyte gene transcription 59. Antifeedant 265. Antifeedant, fish 399. Antifeedant, reef fish 376. Antifoulant 21, 344. Antifoulant, barnacle Balanus amphitrite at nontoxic concentration 689. Antifungal 5, 12, 18, 19, 20, 22, 66, 67, 68, 133, 264, 287, 326, 346, 347, 624, 630, 681, 783, 855. Antifungal inactive, ABRCA 142, 143. Antifungal inactive, Aspergillus clavatus F318a 141, 183. Antifungal inactive, Aspergillus niger 780.

Antifungal inactive, Blumeria graminearum 429. Antifungal inactive, Candida albicans 24, 730, 731, 732, 733, 734, 735, 780. Antifungal inactive, Candida albicans ATCC 10231 329. Antifungal inactive, Candida albicans ATCC 14053 330. Antifungal inactive, Candida albicans ATCC 2019 141, 182, 183. Antifungal inactive, Candida albicans NCPF3153 58, 517, 518. Antifungal inactive, Cryptococcus neoformans and Microsporum gypseum 833. Antifungal inactive, Cryptococcus neoformans ATCC 90112 58, 517, 518. Antifungal inactive, Fusarium oxysporum 429. Antifungal inactive, Trichophyton rubrum 780. Antifungal, agricultural pathogens Fusarium sp. 417. Antifungal, and filamentous fungi 738, 739. Antifungal, Aspergillus brassicae 149. Antifungal, Aspergillus clavatus F318a 182. Antifungal, Aspergillus niger 149, 417. Antifungal, Blumeria graminearum 314. Antifungal, Candida albicans 126, 148, 168, 219, 222, 241, 441, 441, 484, 504, 539, 542, 735, 805, 807, 811, 819. Antifungal, Candida albicans 909. Antifungal, Colletotrichum glocosporioides 429. Antifungal, Cryptococcus neoformans 852. Antifungal, Cryptococcus neoformans and Microsporum gypseum 868. Antifungal, Curvularia lunata 441. Antifungal, Eurotium repens 6. Antifungal, five flimantous fungal strains 429. Antifungal, Fusarium oxysporum 329. Antifungal, Fusarium oxysporum f. cubense 414. Antifungal, Fusariumoxy sporium f. sp. cucumeris 417. Antifungal, Fusariumoxy sporium f. sp. niveum 417. Antifungal, Gloeasporium musae 314, 429. Antifungal, inhibits phytopathogenic fungus Phytophthora infestan, selectly 684. Antifungal, Microbotryum violacea 6.

Index 5 Compound Pharmacological Activity Index

Antifungal, Microsporum gypseum 852. Antifungal, Mycotypha microspore 386. Antifungal, Neurospora crassa 81. Antifungal, P. oralicum CBS 219.30 481, 482. Antifungal, Penicillium sp. 417. Antifungal, Perononphthora cichoralearum 429. Antifungal, phytopathogenic fungi 763. Antifungal, phytopathogenic fungus Cladosporium cucumerinum 130. Antifungal, Phytophthora sojae 314. Antifungal, Rhizoctonia solani 314, 417. Antifungal, Saccharomyces cerevisiae 148. Antifungal, Septoria tritici 38. Antifungal, Trichophyton mentagrophytes 394, 395. Antifungal, Trichophyton rubrum 696. Antifungal, Ustilago violacea 339. Antifungal, yeast 799, 934. Anti-hepatitis C virus, HCV 769. Anti-HIV 505, 370. Anti-HIV-1 331. Antihyperlipidaemic 461. Anti-inflammatory 43, 44, 45, 109, 110, 111, 112, 658, 744, 746, 747, 766. Anti-inflammatory HUVEC Cell Line, target MMP-1, effect decrease, 331. Anti-inflammatory, hmn neutrophil free radical release inhibition, MMOA: - superoxide anion inhibition 366. Anti-inflammatory, HUVEC Cell Line, target COX-2, effect decrease 331. Anti-inflammatory, HUVEC Cell Line, target Il-1α, effect decrease 331. Anti-inflammatory, HUVEC Cell Line, target MCP-1, effect decrease 331. Anti-inflammatory, HUVEC Cell Line, target TSP-1, effect decrease 331. Anti-inflammatory, inhibits PMA-induced adhesion of neutrophils to microtitre plate 603. Anti-inflammatory, inhibits superoxide production by hmn neutrophils in vitro, no short-term toxicity 603. Anti-inflammatory, mouse splenocyte IL-5 inhibitor 159. Anti-inflammatory, rat basophilic leukemia cell histamine release inhibition, MMOA:

377

- inhibition of β-hexosaminidase release 558. Anti-inflammatory, reduction of pro-inflammatory NF-κB, COX-2 and iNOS expressions 547. Antileishmanial 109, 110, 111, 112. Antileishmanial, Leishmania donovani MHOM-ET-67/L82 404, 405, 406. Antileukemia 242, 243. Antimalarial 142. Antimalarial inactive 143. Antimalarial, Plasmodium falciparum 753. Antimalarial, Plasmodium falciparum D6 221. Antimalarial, Plasmodium falciparum K1 404, 405, 406. Antimalarial, Plasmodium falciparum W2 221. Anti-meiotic 738, 739. Anti-metabolite effect 576. Antimicroalgal, marine microalga Coscinodiskus wailesii 331. Antimicroalgal, marine microalga Prorocentrum minimum 331. Antimicrobial 32, 84, 85, 174, 300, 359, 451, 452, 497, 498, 508, 514, 515, 523, 526, 527, 528, 888, 898, 912. Antimitotic 251. Antimutagenic 398, 400, 662. Antimycobacterial, Mycobacterium bacille 935. Antimycoplasmas 624. Antineoplastic, in vivo 303, 426, 643, 666, 667, 858, 898. Antineoplastic, in vivo, ovarian carcinoma in nude mice 255. Anti-obesity, inhibits differentiation of 3T3-L1 cells into adipocytes without accompanying cytotoxicity 220. Antioxidant 280, 559, 768, 782, 889, 921, 941, 942, 401, 278, 767. Antioxidant, ABTS∙+ radical cation scavenger 64. Antioxidant, DPPH radical scavenger 267, 282, 284, 289, 290, 292, 293, 294, 295, 296, 297, 301, 303, 305, 306, 343, 361, 362, 381, 382, 383, 384, 460, 462, 529, 546, 550, 639, 691, 698, 699, 701, 770, 771, 807, 812, 814, 819, 864, 865, 913. Antioxidant, free radical scavenger 325. Antioxidant, free radicals scavenger, DPPH radical 292, 288.

378

Index 5 Compound Pharmacological Activity Index

Antioxidant, free radicals scavenger, NO• radical 292, 288. Antioxidant, free radicals scavenger, O2•− radical 292. Antioxidant, free radicals scavenger, ONOO− radical 288, 292. Antioxidant, hydroxyl radical scavenger 657. Antioxidant, increased anti-oxidative glutathione peroxidase, catalase and superoxide dismutase activities 553. Antioxidant, O2•− radical scavenger 288. Antioxidant, radical scavenger 333, 334. Antioxidant, reduction of ROS over-production 553, 547. Antioxidant, significant 656. Antioxidant, thiobarbituric acid reactive substance TBARS assay 271, 272. Antiparasitic 229, 226, 227, 228. Antiplasmin inhibitor 544, 554, 557. Antiplasmodial, CRPF 881. Antiplasmodial, CRPF W2 138, 61. Antiplasmodial, CSPF 881. Antiplasmodial, CSPF D6 61. Antiplasmodial, hmn erythrocytes type O infected by CRPF 94 87. Antiplasmodial, Plasmodium berghei liver stages 640. Antiplasmodial, Plasmodium falciparum 483, 637. Antiplasmodial, Plasmodium falciparum 94 54. Antiplasmodial, Plasmodium falciparum K1 6, 767, 837, 851, 870, 877, 880. Antiplasmodial, Plasmodium falciparum NF 54 6, 767. Antiproliferative 227, 603, 642. Antiproliferative, KB 899. Antiproliferative, NCI-H460 899. Antiproliferative, weak 640. Antistaphylococcal 370. Antitrypanosomal, Trypanosoma brucei rhodesiense 483. Antitrypanosomal, Trypanosoma brucei rhodesiense STIB 900 404, 405, 406. Antitrypanosomal, Trypanosoma cruzi Tulahuen C4 404, 405, 406.

Antituberculosis, Mycobacterium tuberculosis 61, 150, 379, 633, 808, 809, 851, 870, 880. Antitumor, EGFR tumor 331. Antiulcer 744, 745. Antiviral 643. Antiviral, Enterovirus-71 427, 445, 437. Antiviral, H1N1 virus inhibitor 589. Antiviral, H3N2 virus 349, 489, 503. Antiviral, Herpes simplex virus HSV-1 198, 203. Antiviral, HSV virus 23, 51. Antiviral, HSV-1 490, 773, 774, 775, 776, 777, 778. Antiviral, IFV 448, 490, 648, 736, 737. Antiviral, IFV H1N1 582, 590. Antiviral, influenza A H1N1 50. Antiviral, influenza A H1N1 with lower cytotoxicity 33. Antiviral, influenza A virus/MDCK 773, 774, 775, 776, 777, 778. Antiviral, influenza virus IFV virus 65. Antiviral, inhibits HIV-1 infection, MMOA: - Viralp24 antigen production and reverse transcriptase inhibition 544. Antiviral, inhibits multiplication of tobacco mosaic virus TMV 688. Antiviral, porcine reproductive and respiratory syndrome PRRS virus 885, 914. Antiviral, SARS-Corona virus viral protease 3CL 686. Antiviral, TMV virus 325, 337, 402. Antiviral, Vesicular stomatitis virus VSV 198, 203. Apoptogenic, BAEC Cell Line, target Caspase-2, -3, -8, -9, effect increase 331. Apoptogenic, BAEC Cell Line, target Cleaved lamin-A, effect increase 331. Apoptogenic, BAEC Cell Line, target Cytochrome C, effect increase in cytoplasm 331. Apoptogenic, HUVEC Cell Line, target p-Bad, effect increase 331. Apoptosis inducer 651, 652. Aromatase inhibitor 456, 663, 664. Aromatase inhibitor, hmn recombinant aromatase [hmn Cyp 19 + P450 reductase supersomes] 435. Arrests cells in G2/M phase of cell cycle 127. Atropisomeric 522, 541. Attenuates type II diabetes, db/db mouse model 547.

Index 5 Compound Pharmacological Activity Index

B Bacteriostatic 537. Bcl-2 protein inhibitor 492, 493, 534, 535. Binds to neuropeptide Y receptor 283. Blocking proliferation of EGFR-dependent hmn cancer cell lines MCF7 and ZR-75-1 331. Blood vessel growth inhibitor 153. Bronchodilator 353, 354, 355. C Cancer-preventive activity, mouse JB6 P+ CI41 cells 367. Cathartic 888, 898, 912, 889. Cathepsin B inhibitor 321, 322, 323. Causes dermatitis 365. CD-4-binding activity 450. Cell cycle arrest were evaluated, HepG2 371. Cell cycle inhibitor, mammalian 756. Cell cycle inhibitor, mammalian, tsFT210, caused complete arrest in G2/M phase 632. Cell division inhibitor, fertilized eggs of sea urchin Strongylocentrotus intermedius 510, 511, 512, 519, 520, 521. Cell division inhibitor, fertilized sea urchin eggs 7. Cell growth and proliferation inhibitor, HTCLs cells 706, 707. Cell growth inhibitor 729, 761, 762, 792, 793. Cell proliferation inhibitor 679, 680. CETP inhibitor 799. Collagenase inhibitor 681. COMPARE analysis 712, 714, 715. COMPARE program suggested a novel mechanism of action 709, 713, 716, 719. Contact allergen 278, 367. COX-2 inhibitor 772. CYP1A inhibitor 434, 435, 436. CYP1A inhibitor, without cytotoxicity 388, 433. Cytochrome P450 1A inhibitor 663, 664. Cytoprotection of pancreatic β-cells, protects pancreatic β-cells damage caused by hyperglycaemia due to streptozotocin 553. Cytotoxic 34, 35, 82, 155, 156, 157, 172, 173, 190, 191, 208, 209, 300, 333, 342, 390, 632, 685, 694, 695, 788, 831, 841, 842, 843, 844, 862, 874, 875, 886, 897.

379

Cytotoxic inactive, A375-S2 676, 677, 678. Cytotoxic inactive, A549 60, 62, 63, 69, 70, 73, 74, 91, 145, 146, 203, 282, 290, 384, 631, 637, 637, 689, 692, 709, 712, 715, 798, 804, 805, 806, 807, 810, 811, 812, 813, 814, 818, 819. Cytotoxic inactive, ACC-MESO-1 430, 431, 432. Cytotoxic inactive, ACHN 712. Cytotoxic inactive, Bel7402 60, 62, 63, 69, 70, 73, 74, 282, 290, 293, 294, 295, 296, 381, 382, 384. Cytotoxic inactive, BSY1 709. Cytotoxic inactive, C6 332. Cytotoxic inactive, Calu3 409, 412, 443, 444. Cytotoxic inactive, CCRF-CEM 1. Cytotoxic inactive, CHO-K1 274, 277. Cytotoxic inactive, Colo320 120, 170. Cytotoxic inactive, cultured P388 47, 129. Cytotoxic inactive, DMS114 709, 712. Cytotoxic inactive, DMS273 709, 712. Cytotoxic inactive, drug-sensitive parental KB 888, 890, 891, 892, 893, 894, 895, 898, 905, 907, 918, 919. Cytotoxic inactive, DU145 1, 146, 709, 712, 714. Cytotoxic inactive, EAC 519, 520. Cytotoxic inactive, H460 264, 274, 277, 366, 781. Cytotoxic inactive, H929 with or without stromal cell 442. Cytotoxic inactive, H9c2 332. Cytotoxic inactive, HBC4 709, 712, 714. Cytotoxic inactive, HBC5 709, 714. Cytotoxic inactive, HCC2998 709, 712, 714. Cytotoxic inactive, HCT116 409, 412, 443, 444, 709, 712, 714. Cytotoxic inactive, HCT15 709, 712, 714. Cytotoxic inactive, HeLa 60, 62, 63, 70, 71, 72, 74, 332, 418, 419, 420, 421, 422, 423, 425, 446, 447, 752, 924, 940. Cytotoxic inactive, Hep2 171, 316. Cytotoxic inactive, HepG2 144, 145, 146, 171, 316, 418, 419, 420, 421, 422, 423, 424, 425, 446, 447. Cytotoxic inactive, HL60 120, 282, 296, 318, 381, 382, 710, 711, 740, 741, 871, 924. Cytotoxic inactive, HT29 203, 264, 274, 276, 277, 366, 709, 712, 714.

380

Index 5 Compound Pharmacological Activity Index

Cytotoxic inactive, Huh7 412, 443, 418, 419, 420, 421, 422, 423, 425, 446, 447, 424, 411, 409, 444, 442. Cytotoxic inactive, K562 60, 62, 63, 70, 74, 175, 176, 502. Cytotoxic inactive, KB 197, 219, 228, 229, 428, 710, 711, 717, 740, 741, 876. Cytotoxic inactive, KBV200 197, 428, 888, 890, 891, 892, 893, 894, 895, 898, 905, 907, 918, 919. Cytotoxic inactive, KM12 709, 712, 714. Cytotoxic inactive, KMS34 with stromal cell 442. Cytotoxic inactive, L1210 120, 170, 710, 711, 717, 718, 740, 741, 861. Cytotoxic inactive, L363 with or without stromal cell 442. Cytotoxic inactive, LOX-IMVI 709, 712. Cytotoxic inactive, MCF-10A 408, 409, 412, 443, 444. Cytotoxic inactive, MCF7 145, 146, 274, 277, 418, 419, 420, 421, 422, 423, 424, 425, 446, 447, 642, 709, 712, 714, 715, 781. Cytotoxic inactive, MDA-MB-231 146, 709, 713, 714. Cytotoxic inactive, MDA-MB-231 with or without stromal cell 442. Cytotoxic inactive, MDA-MB-435 409, 412, 443, 444. Cytotoxic inactive, MEL28 61. Cytotoxic inactive, MKN1 709, 712. Cytotoxic inactive, MKN28 715, 712. Cytotoxic inactive, MKN45 715, 712. Cytotoxic inactive, MKN7 709, 712. Cytotoxic inactive, MKN74 712. Cytotoxic inactive, MM1S with or without stromal cell 442. Cytotoxic inactive, Molt4 282, 290, 382. Cytotoxic inactive, NCI’s 60 tumour cell line panel 839. Cytotoxic inactive, NCI-H226 709, 712, 714. Cytotoxic inactive, NCI-H23 709, 712, 714. Cytotoxic inactive, NCI-H460 146, 642, 709, 712, 715. Cytotoxic inactive, NCI-H522 709, 714. Cytotoxic inactive, OCILY17R with or without stromal cell 442.

Cytotoxic inactive, OCIMY5 with stromal cell 442. Cytotoxic inactive, OVCAR-3 709. Cytotoxic inactive, OVCAR-4 709, 712, 713, 714. Cytotoxic inactive, OVCAR-5 709, 712, 713, 714. Cytotoxic inactive, OVCAR-8 709, 712. Cytotoxic inactive, P388 203, 223, 394, 395, 710, 711, 740, 741, 757, 925. Cytotoxic inactive, P388/Dox 229. Cytotoxic inactive, PC3 709, 712, 714. Cytotoxic inactive, PC3 with or without stromal cel 442. Cytotoxic inactive, RXF-631L 712, 713, 714. Cytotoxic inactive, SF268 264, 274, 276, 277, 642, 709, 712, 714, 781. Cytotoxic inactive, SF295 709, 712, 714. Cytotoxic inactive, SF539 709, 712. Cytotoxic inactive, SGC7901 71, 72. Cytotoxic inactive, SK-OV-3 709, 712, 715. Cytotoxic inactive, SMMC-7721 798, 804, 805, 806, 807, 810, 811, 812, 813, 814, 818, 819. Cytotoxic inactive, SNB75 709, 712, 714. Cytotoxic inactive, SNB78 709, 712, 714. Cytotoxic inactive, St4 709, 712. Cytotoxic inactive, SW1990 146, 457. Cytotoxic inactive, SW480 71, 72. Cytotoxic inactive, U251 709, 712, 714. Cytotoxic inactive, U937 418, 419, 420, 422, 423, 446, 447. Cytotoxic inactive, Vero 791, 832, 876. Cytotoxic inactive, WEHI-164 160, 161. Cytotoxic, 9KB 693. Cytotoxic, A2780 244, 401, 437. Cytotoxic, A2780CisR 401, 437. Cytotoxic, A375-S2 749. Cytotoxic, A498 1. Cytotoxic, A549 55, 56, 61, 87, 88, 113, 119, 121, 127, 127, 128, 134, 148, 198, 224, 278, 279, 293, 294, 295, 296, 301, 312, 368, 369, 371, 381, 382, 383, 438, 439, 440, 484, 540, 567, 571, 572, 600, 601, 602, 700, 713, 714, 716, 719, 748, 863, 871, 872, 879, 925, 926. Cytotoxic, A549, 100μmol/L 944. Cytotoxic, ACHN 709, 715, 714, 713, 716, 719. Cytotoxic, B16 225, 226, 227, 228, 229.

Index 5 Compound Pharmacological Activity Index

Cytotoxic, B16-F-10 371. Cytotoxic, BC-1 753. Cytotoxic, Bel7402 383, 925. Cytotoxic, Bel7402, 100μmol/L 944. Cytotoxic, BGC823 29. Cytotoxic, BGC823, 100μg/mL 328. Cytotoxic, biochemical induction assay 945, 946. Cytotoxic, BR1 DNA repair competent Chinese hamster ovary line 352. Cytotoxic, BSY1 670, 712, 713, 714, 715, 716, 719. Cytotoxic, BXF-1218L 654. Cytotoxic, BXF-T24 654. Cytotoxic, BXPC3 767. Cytotoxic, C6 900, 901, 908. Cytotoxic, Calu3 408, 410, 411, 442, 902. Cytotoxic, CHO-K1 264, 273, 275, 276, 366, 370. Cytotoxic, CNXF-SF268 654. Cytotoxic, Colon205 509. Cytotoxic, Colon250 13. Cytotoxic, CV-1 567. Cytotoxic, CXF-HCT116 654. Cytotoxic, CXF-HT29 654. Cytotoxic, differentiation-inducing activity to K562 cells into erythroblast 370, 371. Cytotoxic, DMS114 670, 713, 714, 715, 716, 719. Cytotoxic, DMS273 713, 714, 715, 716, 719. Cytotoxic, DNA repair defective cell lines 352. Cytotoxic, Dox40 with or without stromal cell 442. Cytotoxic, drug-sensitive parental KB 889. Cytotoxic, DU145 713, 715, 716, 719, 767. Cytotoxic, DU4475 142, 143. Cytotoxic, EAC 219. Cytotoxic, EM9 topoisomerase I sensitive Chinese hamster ovary line 352. Cytotoxic, F1 604, 605, 606. Cytotoxic, Farage with or without stromal cell 442. Cytotoxic, fertilized eggs of sea urchin Strongylocentrotus intermedius 364. Cytotoxic, fertilized sea urchin eggs 281. Cytotoxic, Fl 607, 608. Cytotoxic, free acids are more active than their methyl esters 251, 252. Cytotoxic, GXF-251L 654. Cytotoxic, H2887 902.

381

Cytotoxic, H460 138, 273, 275, 276, 370. Cytotoxic, H69AR 87. Cytotoxic, HBC4 713, 715, 716, 719. Cytotoxic, HBC5 712, 713, 715, 716, 719. Cytotoxic, HCC2998 1, 670, 713, 715, 716, 719. Cytotoxic, HCC-H102 87. Cytotoxic, HCC-S102 55, 56. Cytotoxic, HCT116 1, 2, 71, 72, 135, 367, 408, 410, 411, 442, 713, 715, 716, 719, 830, 835, 836, 839, 845, 847, 848, 849, 920, 922, 935, 947, 948, 949. Cytotoxic, HCT116, potent 945. Cytotoxic, HCT15 713, 715, 716, 719, 900, 901, 908. Cytotoxic, HCT8 88. Cytotoxic, HeLa 30, 31, 49, 55, 56, 69, 73, 87, 94, 104, 124, 248, 250, 315, 327, 331, 370, 371, 424, 430, 431, 432, 744, 749, 760, 923, 937, 938, 939, 947, 948, 949. Cytotoxic, HeLa, 100μg/mL 328. Cytotoxic, HeLa, potent 945. Cytotoxic, HeLa-S3 742. Cytotoxic, Hep2 796. Cytotoxic, HepG2 55, 56, 87, 149, 329, 370, 371, 441, 540, 796, 943. Cytotoxic, HL60 25, 26, 27, 28, 29, 33, 49, 55, 56, 87, 94, 124, 290, 293, 294, 295, 313, 331, 370, 371, 383, 384, 438, 439, 440, 631, 689, 703, 709, 712, 713, 714, 715, 716, 717, 718, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 742, 872, 923, 925, 926. Cytotoxic, HL60, 100μg/mL 328. Cytotoxic, HL60, 100μmol/L 944. Cytotoxic, HM02 943. Cytotoxic, HMEC 301. Cytotoxic, hmn primary tumour cells 61. Cytotoxic, HOP-92 1. Cytotoxic, HT with or without stromal cell 442. Cytotoxic, HT1080 331. Cytotoxic, HT29 61, 127, 134, 148, 198, 225, 226, 227, 228, 229, 273, 275, 278, 279, 370, 371, 540, 567, 571, 599, 600, 601, 602, 611, 612, 613, 614, 616, 617, 713, 715, 716, 719, 748. Cytotoxic, HT460 367. Cytotoxic, HTC116 331. Cytotoxic, HTCLs cells 192, 193, 506, 507, 706, 707, 729, 884. Cytotoxic, HuCCA-1 55, 56, 87.

382

Index 5 Compound Pharmacological Activity Index

Cytotoxic, Huh7 408, 410. Cytotoxic, inhibitory effects on cell cycle arrest in HepG2 cell line was evaluated 370. Cytotoxic, inhibitory effects on maturation of starfish oocytes was evaluated 370. Cytotoxic, inhibits cell proliferation by polymerizing and hyperstabilizing tubulin, similar to paclitaxel but shows activity against paclitaxel resistant tumours 127. Cytotoxic, K562 28, 30, 31, 64, 65, 69, 73, 94, 401, 437, 629, 947, 948, 949. Cytotoxic, K562, 100μg/mL 328. Cytotoxic, K562, potent 945. Cytotoxic, KB 55, 56, 87, 103, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 225, 226, 227, 413, 481, 482, 620, 621, 622, 623, 638, 690, 697, 718, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 753, 791, 832, 837, 851, 852, 869, 870, 877, 880, 910. Cytotoxic, KB drug-sensitive parental 910. Cytotoxic, KB16 13. Cytotoxic, KB-3-1 574, 575, 576, 579. Cytotoxic, KBV200 413, 690, 697, 889, 910, 910. Cytotoxic, KM12 713, 715, 716, 719. Cytotoxic, KM20L2 767. Cytotoxic, KMS34 without stromal cell 442. Cytotoxic, KU812F with or without stromal cell 442. Cytotoxic, L1210 375, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728. Cytotoxic, L5178Y 125, 401, 437, 672, 821, 822. Cytotoxic, L-6 404, 405, 406. Cytotoxic, LNCaP 947, 948, 949. Cytotoxic, LNCaP, potent 945. Cytotoxic, LoVo 620, 621, 622, 623. Cytotoxic, LOX 509. Cytotoxic, LOX-IMVI 1, 713, 714, 715, 716, 719. Cytotoxic, LXF-1121L 654. Cytotoxic, LXF-289L 654. Cytotoxic, LXF-526L 654. Cytotoxic, LXF-629L 654. Cytotoxic, LXF-H460 654. Cytotoxic, MAXF-401NL 654. Cytotoxic, MAXF-MCF7 654. Cytotoxic, MCF-10A 410, 411, 442.

Cytotoxic, MCF7 264, 273, 275, 276, 356, 357, 366, 370, 370, 371, 604, 605, 606, 607, 608, 640, 670, 689, 700, 713, 716, 719, 767, 791, 832, 837, 851, 852, 869, 870, 876, 877, 880, 882, 883. Cytotoxic, MDA-MB 88. Cytotoxic, MDA-MB-231 55, 56, 87, 127, 712, 715, 716, 719. Cytotoxic, MDA-MB-435 1, 408, 410, 411, 442, 882, 883. Cytotoxic, MEL28 134, 148, 278, 279, 367, 571, 572, 601, 602, 748. Cytotoxic, MEXF-276L 654. Cytotoxic, MEXF-462NL 654. Cytotoxic, MEXF-520L 654. Cytotoxic, MKN1 670, 713, 714, 715, 716, 719. Cytotoxic, MKN28 709, 713, 714, 716, 719. Cytotoxic, MKN45 709, 713, 714, 716, 719. Cytotoxic, MKN7 713, 714, 715, 716, 719. Cytotoxic, MKN74 709, 713, 714, 715, 716, 719. Cytotoxic, Molt4 293, 294, 295, 296, 381, 383, 384, 509. Cytotoxic, mouse broblast cells 795. Cytotoxic, mouse erythrocytes 364. Cytotoxic, mouse splenic cells 504. Cytotoxic, MRC5CVl 225, 230. Cytotoxic, murine and hmn tumour cells, GI50 from 0.001μg/mL to < 0.0001μg/mL 761, 762. Cytotoxic, mus xenograft model, hmn ovarian carcinoma 256, 257, 258, 259. Cytotoxic, NCI-H226 1, 713, 715, 716, 719. Cytotoxic, NCI-H23 713, 715, 716, 719. Cytotoxic, NCI-H460 370, 371, 640, 713, 714, 716, 719, 767, 792, 793. Cytotoxic, NCI-H522 1, 670, 712, 713, 715, 716, 719. Cytotoxic, NOMO-1 331. Cytotoxic, NSCLC 902. Cytotoxic, NSCLC-N6 225, 226, 227, 228, 229. Cytotoxic, NUGC-3 742. Cytotoxic, number of tumour cell lines, IC50 = 0.01~98 ng/mL 945. Cytotoxic, OCIMY5 without stromal cell 442. Cytotoxic, OPM2 with or without stromal cell 442. Cytotoxic, OVCAR-3 1, 509, 670, 712, 713, 714, 715, 716, 719.

Index 5 Compound Pharmacological Activity Index

Cytotoxic, OVCAR-4 715, 716, 719. Cytotoxic, OVCAR-5 715, 716, 719. Cytotoxic, OVCAR-8 713, 714, 715, 716, 719. Cytotoxic, OVXF-899L 654. Cytotoxic, OVXF-OVCAR3 654. Cytotoxic, P388 16, 55, 56, 83, 87, 127, 219, 225, 226, 227, 228, 229, 371, 600, 709, 714, 715, 717, 718, 720, 726, 728, 729, 748, 88, 89, 113, 119, 121, 128, 134, 148, 158, 198, 233, 234, 235, 236, 237, 240, 269, 278, 279, 343, 368, 369, 372, 567, 571, 572, 601, 602, 629, 660, 668, 669, 670, 671, 708, 712, 713, 716, 719, 721, 722, 723, 724, 725, 727, 758, 855, 860. Cytotoxic, P388, potent 238, 239. Cytotoxic, P388/Dox 225, 226, 227, 228. Cytotoxic, panel of 12 cell lines 142, 143. Cytotoxic, panel of 24 tumour cell lines 945, 946. Cytotoxic, panel of 25 diverse cell lines, IC50 = 0.09μg/mL 255. Cytotoxic, panel of 36 hmn tumour cell lines 654. Cytotoxic, panel of 36 hmn tumour cell lines, mean IC50 = 5.5μg/mL, 10μg/mL, 7 active, 29 inactive 454, 455. Cytotoxic, panel of 39 hmn tumour cell lines 238, 239. Cytotoxic, panel of 39 hmn tumour cell lines, 22 inactive, 17 active, selective, mean Log10 GI50 mol/L = –4.05 714. Cytotoxic, panel of 39 hmn tumour cell lines, 34 inactive, 5 active, selective, mean Log10 GI50 mol/L = –4.10 709. Cytotoxic, panel of 39 hmn tumour cell lines, 34 inactive, 5 active, selective, mean Log10 GI50 mol/L = –4.19 712. Cytotoxic, panel of 39 hmn tumour cell lines, 39 active, mean Log10 GI50 mol/L = –5.45 716. Cytotoxic, panel of 39 hmn tumour cell lines, 39 active, mean Log10 GI50 mol/L = –5.15 719. Cytotoxic, panel of 39 hmn tumour cell lines, 4 inactive, 35 active, selective, mean Log10 GI50 mol/L = –4.83 713. Cytotoxic, panel of 39 hmn tumour cell lines, 6 inactive, 33 active, selective, mean Log10 GI50 mol/L = –4.61 715.

383

Cytotoxic, panel of NCI’s 60 cell lines, selected for renal, CNS and breast tumour cell lines 17. Cytotoxic, panel of NCI’s 60 hmn tumour cell lines, mean GI50 < 0.011μmol/L 1. Cytotoxic, PAXF-1657L 654. Cytotoxic, PAXF-PANC1 654. Cytotoxic, PC3 1, 713, 715, 716, 719. Cytotoxic, PRXF-22RV1 654. Cytotoxic, PRXF-DU145 654. Cytotoxic, PRXF-LNCAP 654. Cytotoxic, PRXF-PC3M 654. Cytotoxic, PS (=P388) 178, 179, 216, 217, 218. Cytotoxic, PXF-1752L 654. Cytotoxic, Raji 638. Cytotoxic, RPMI8226 with or without stromal cell 442. Cytotoxic, RXF-1781L 654. Cytotoxic, RXF-393 1. Cytotoxic, RXF-486L 654. Cytotoxic, RXF-631L 709, 715, 716, 719. Cytotoxic, selective 840. Cytotoxic, several cell lines 635. Cytotoxic, several HTCLs cells 319, 661. Cytotoxic, several tumour cell lines, mild 23. Cytotoxic, SF268 273, 275, 366, 370, 370, 371, 640, 713, 715, 716, 719, 767. Cytotoxic, SF295 713, 715, 716, 719. Cytotoxic, SF539 713, 714, 715, 716, 719. Cytotoxic, significant 280. Cytotoxic, SK-MEL-28 1. Cytotoxic, SK-OV-3 713, 714, 716, 719. Cytotoxic, SMMC-7721 301. Cytotoxic, SNB19 509. Cytotoxic, SNB75 1, 1, 713, 715, 716, 719. Cytotoxic, SNB78 713, 715, 716, 719. Cytotoxic, St4 713, 714, 715, 716, 719. Cytotoxic, SW1990 734. Cytotoxic, SW620 315, 900, 901, 908. Cytotoxic, T-24 225, 230. Cytotoxic, T47D 55, 56, 87. Cytotoxic, THP-1 331. Cytotoxic, two mammalian tumour cell lines 222. Cytotoxic, U251 713, 715, 716, 719. Cytotoxic, U937 421, 424, 425. Cytotoxic, UV20 352. Cytotoxic, UXF-1138L 654. Cytotoxic, Vero 837, 851, 852, 869, 870, 877, 880.

384

Index 5 Compound Pharmacological Activity Index

Cytotoxic, Vero, weak 214, 215. Cytotoxic, weak 249. Cytotoxic, WI26 679, 680. Cytotoxic, XRS-6 topoisomerase II sensitive Chinese hamster ovary line 352. Cytotoxin 691. D Defence allomone of pulmonate Onchidium verruculatum 186, 186. Dermatoxic 86. DHFR inhibitor 572. Dietary chemopreventive agent, inhibits development of neoplasms in animal models 325. DNA cleaving agent, Antineoplastic, Antibiotics 256, 257, 258, 259. DNA polymerases inhibitor, bovine DNA polymerase a and c 931, 932. DNA polymerases inhibitor, mammalian, A family, pol γ, B family, pols α, δ and ε, and Y family pols η, ι and κ, selective 706, 707. Dual-specificity PP inhibitor, VHR 95, 96, 97, 98, 99, 100. E EGFR inhibitor 331. Endoproteinase inhibitor 336. Enoyl-ACP reductases inhibitor 453. Enzymes inducer, enzymes involved in carcinogen metabolism 657. Enzymes inducer, epoxide hydrolase 657. Enzymes inducer, glutathione S-transferase 657. Epigenetic modulatory activity 902. Estrogen 767. Eukaryotic DNA polymerases selective inhibitor, MMOA: - specific inhibition of DNA polymerase β and κ 755. Eukaryotic DNA polymerases selective inhibitor, X and Y families 649. Eye irritant, eye skin 326. F Fab I inhibitor 537. Farnesoid X receptor antagonist 78, 79, 80.

Farnesyl-protein transferase inhibitor 302. Fertilisation inhibitor, Asterina pectinifera 336. Flavour component, marine fish, molluscs and crustaceans 261. Flavouring ingredient 308. G Glucose-6-phosphatase inhibitor 582. Glutathione S-transferases GST inhibitor 657. Glycation inhibitor 550. Glycogen synthase kinase-3β inhibitor 39, 40, 41, 42. Growth stimulant, corn and barley rootlets 665. Guanosine monophosphate synthetase inhibitor 268, 494, 499, 500, 501, 516. H Hemolytic 504. Herbicide 151. Histamine release inhibitor, hmn basophilic granulocyte KU-812 547. HIV reverse transcriptase inhibitor 370. HIV-1 protease inhibitor 231, 232. HIV-integrase inhibitor 283. HLE inhibitor 927. HMG-CoA reductase inhibitor 380. Hmn kinases inhibitor FLT3 656. Hmn kinases inhibitor SAK 656. hTopo l isomerase inhibitor 887. Hypoglycaemic, in vivo, streptozotocin-induced diabetic mice 324. Hypoglycemic, AGE formation inhibition 547, 550, 556. Hypoglycemic, aldose reductase inhibitor, RLAR 284, 547, 548, 550, 556, 557. Hypoglycemic, C57BL/KsJ-db/db diabetic mice in vivo, reduction of blood glucose, glycosylated hemoglobin levels 547. Hypoglycemic, C57BL/KsJ-db/db diabetic mice in vivo, reduction of hepatic lipids concentration and improvement of impaired glucose tolerance 547. Hypoglycemic, C57BL/KsJ-db/db diabetic mice in vivo, reduction of glucose-6-phosphatase and phosphoenolpyruvate carboxykinase enzymes activities and increased glucokinase activity 547.

Index 5 Compound Pharmacological Activity Index

Hypoglycemic, increased glucose uptake by GLUT4 via PI3-K/Akt and AMPK signalling pathways, L-6 rat myoblast cells 553. Hypoglycemic, maltase inhibitor 285, 297. Hypoglycemic, pancreatic lipase inhibitor 547, 550, 552, 556. Hypoglycemic, PTP1B inhibitor 284, 287, 298, 307, 389, 524, 547, 548, 550, 556, 557, 565, 785, 786, 787. Hypoglycemic, PTP1B inhibitor, PTP1B and hypoglycaemic effect in streptozotocininduced diabetic Wistar rats 286, 299, 377, 385. Hypoglycemic, streptozotocin-induced diabetic mice in vivo, reduction of post-prandial blood glucose level and delayed absorption of dietary carbohydrates 547, 549. Hypoglycemic, sucrase inhibitor 285, 297. Hypoglycemic, α-amylase inhibitor 544, 547, 547, 547, 548, 549, 550, 551, 552, 556, 557, 560. Hypoglycemic, α-amylase inhibitor, Fucus distichus’ ethyl acetate subfraction 22 561, 562, 563. Hypoglycemic, α-glucosidase inhibitor 284, 284, 285, 297, 324, 544, 546, 547, 547, 547, 548, 548, 549, 550, 550, 551, 552, 556, 556, 557, 557. Hypoglycemic, α-glucosidase inhibitor, Bacillus stearothermophilus 263, 266, 285. Hypoglycemic, α-glucosidase inhibitor, Fucus distichus’ ethyl acetate subfraction 22 561, 562, 563. Hypoglycemic, α-glucosidase inhibitor, rat intestinal maltase 285. Hypoglycemic, α-glucosidase inhibitor, rat intestinal maltase and rat instestinal sucrase 263, 266, 560. Hypoglycemic, α-glucosidase inhibitor, rat intestinal sucrase 285. Hypoglycemic, α-glucosidase inhibitor, Saccharomyces cerevisiae 263, 266, 285, 285, 291. Hypolipemic 941, 942. I Ichthyotoxic 114, 115, 116, 117, 118, 180, 181. Ichthyotoxin 187, 188, 210, 212, 213, 376, 659.

385

IL-4 signal transduction inhibitor 800. Immune system activity, activation of Ca2+-mobilization, MMOA: - ionotropic P2Y11 receptor activation 566, 570. Immunosuppressant 127, 576, 580, 643. Immunosuppressive 304. IMP dehydrogenase inhibitor 376. Increases in cells percentage in sub-G1 fraction 313, 318. Inducer of mitochondria-mediated apoptosis, yeast Saccharomyces cerevisiae 877. Inducer of NAD[P]H quinone reductase, cultured mouse Hepa1c1c7 cells 663, 664. Inducer of NAD[P]H quinone reductase, Hepa1c1c7 434, 435, 436, 388, 433. Induces production of cAMP, GPR12 transfected CHO and HEK-293 132. Induces vesiculation of golgi membranes 370. Inhibitor inactive, other eukaryotic or prokaryotic polymerases, or other DNA metabolic enzymes 755. Inhibitor inactive, other eukaryotic or prokaryotic polymerases, or other DNA metabolic enzymes 649. Inhibitor of VEGF-induced endothelial cell growth 402. Inhibitors of kinase could be useful for treating autoimmune diseases 543. Inhibitory effects on maturation of starfish oocytes 371. Inhibitory effects on proliferation, migration, and tubule formation 803, 816. Inhibits binding of dopamine D-1 selective ligand to bovine corpus striatum membrane 856. inhibits bioluminescence Vibrio harveyi 48. Inhibits cell cycle completely blocks NSCLC-N6 in G phase 229. Inhibits cell cycle significant decreases S phase with partial blocks 225, 226, 227, 228. Inhibits cholesteryl ester transfer protein activity 738, 739. Inhibits cytochrome P450 1A CYP1A 657. Inhibits DNA synthesis 920. Inhibits growth of co-occuring thaustrochytrid Schizochytrium aggregatum 764. Inhibits H1N1 virus neuraminidase 589. Inhibits hatching of sea urchin embryos 335.

386

Index 5 Compound Pharmacological Activity Index

Inhibits hypoxia-induced activation of VEGF gene promotor Hep3B 859. Inhibits indoleamine 2, 3-dioxygenase IDO 826, 827, 828. Inhibits LDL oxidation 325. Inhibits mycobacterial PTPB strongly 150, 379. Inhibits NO production and expression, several pro-infiammatory cytokines RAW264.7 cells 48. Inhibits peroxidation of linolenic acid 639. Inhibits premature mitosis, MMOA: - PP2A inhibition 253, 254. Inhibits sperm fertilizing ability 504. Inhibits VEGF-A dependent endothelial cell sprouting, cellularangiogenesis assay 401. Inihibits action of plasma α2-macroglobulin 555. Inihibits actions of plasma α2-macroglobulin and α2-plasmin inhibitor 547. Inosine monophosphate dehydrogenase IMPDH inhibitor 268, 494, 499, 500, 501, 516. Insecticidal 806. Insecticide 174. K Kinase EGFR inhibitor 391, 392, 393. Kinase inhibitor, high selectivity towards CDK1 and CDK2 33. Kinases inhibitor, CDK4/cyclin D1 911, 915, 916. Kinases inhibitor, EGFR 911, 915, 916. Kinases inhibitor, PKC-ε 911, 915, 916. L LD50 brine shrimp 168, 189. LD50 goldfish 189. LD50 mus 519, 520. LD50 mus acute toxic 211. LD50 mus ipr 873, 874, 875, 877, 912. LD50 mus ivn 875. LD50 mus orl 262, 326, 624, 691. LD50 rat ipr 625. LD50 rat orl 266. LD50 snail 168. LD50 snail vector Biomphalaria glabrata 168. LD99 mus 211. Lehualides were moderately toxic to sensitised yeast cells but not to wild type and are

therefore susceptible to efflux pump action 136. Leukocyte elastase inhibitor, hmn, selective 789, 790. Low acute toxicity 537. M Melanin biosynthesis inhibitor 140. Metalloproteinase inhibitor 479. Metallo-β-lactamase inhibitor, angiotensinconverting enzyme ACE 653, 682, 683. Metallo-β-lactamase inhibitor, bacterium Bacillus cereus II 653, 682, 682, 683, 683. Metallo-β-lactamase inhibitor, bacterium Bacteroides fragilis CfiA 653, 653, 682, 682, 683, 683. Metallo-β-lactamase inhibitor, bacterium IMP-1 683. Metallo-β-lactamase inhibitor, bacterium Pseudomonas aeruginosa IMP-1 653, 682, 682, 683. Metallo-β-lactamase inhibitor, metallo-βlactamase of L-1 653, 682, 683. Microtubule assemblage inhibitor 245. Microtubule assembly inhibitor 783. Might be possible ligand for GPR12, which can be significant molecular target for treating a variety of neurological disorders 132. Might induce apoptosis via a mitochondrial pathway 910. Migration inhibitor 803, 815, 816. Mitotic cell division inhibitor 281. Molluscacidal 331. Molluscacidal, marine snail Biomphalaria glabrata 481, 482. Molluscacidal, snail vector Biomphalaria glabrata 168. Monoamine oxidase inhibitor 898. Mosine 5ʹ-monophosphate dehydrogenase inhibitor 378. Mutagenic 365. Mycotoxin 797, 801, 802, 817, 820, 823, 824, 825. N Na/K-ATPase inhibitor 568, 569, 673, 674, 675. Nematocide, potent and selective, inhibitor of larval development of parasitic nematodes 8, 9.

Index 5 Compound Pharmacological Activity Index

Nerve growth factor agonist 52. Nervous system activity, butyrylcholinesterase inhibitor 374. Neurotoxin 169. NO production inhibitor, LPS-induced macrophages 522. NS3-4A protease inhibitor 769. O Odour 261. P P2Y11 receptor agonist 570. P2Y11 receptor agonist, some selectivity for P2Y11 over P2Y1 and P2Y2 receptors 566. PDE inhibitor 803. PDE5 inhibitor, hmn platelet 350, 351. Pfnek-1 inhibitor 338. Phospholipase C inhibitor 450. Phytotoxic 304, 691, 759, 801. Phytotoxin 139, 151, 152, 157, 162, 163, 185, 857, 934. Phytotoxin, various banana cultivars 219. PK inhibitor inactive 437. PK inhibitor inactive, AKT1 401, 437. PK inhibitor inactive, AXL 437. PK inhibitor inactive, FAK 437. PK inhibitor inactive, MEK1 wt 401, 437. PK inhibitor inactive, MET wt 437. PK inhibitor inactive, NEK2 437. PK inhibitor inactive, NEK6 437. PK inhibitor, ALK 401, 437. PK inhibitor, ARK5 401, 437. PK inhibitor, Aurora-B 401, 437. PK inhibitor, AXL 401. PK inhibitor, FAK 401. PK inhibitor, IGF1-R 401, 437. PK inhibitor, MET wt 401, 437. PK inhibitor, NEK2 401, 437. PK inhibitor, NEK6 401. PK inhibitor, PIM1 401, 437. PK inhibitor, PLK1 401, 437. PK inhibitor, PRK1 401, 437. PK inhibitor, SRC 401, 437. PK inhibitor, VEGF-R2 401, 437. PKs inhibitor, 16 different PKs 401, 437. Plant growth inhibitor 156, 463, 581, 743. Plant growth regulator 174. Platelet aggregation inhibitor 325.

387

Pluramycin Antibiotics 920. Potent DNA damaging agent with minimum induction concentration ≤ 0.1 ng/spot 945, 946. PP inhibitor inactive, Cdc25a, PTP1B, VHR, MPtpA and VE-PTP 185. PP inhibitor, MPtpB 185. PP inhibitor, selective 251. PP1 inhibitor, selective 591, 592, 593, 594, 595, 596, 597, 598. PP2A inhibitor, selective 591, 592, 593, 594, 595, 596, 597, 598. PPs inhibitor inactive, VHR, MPtpA and VE-PTP 687. PPs inhibitor, Cdc25a 687. PPs inhibitor, MPtpB 320, 634, 687. PPs inhibitor, PTP1B 687. PPs inhibitors inactive, Cdc25a, PTP1B, VHR, MPtpA and VE-PTP 320, 634. Proliferation inhibitor 803, 815, 816. Promotor of tubulin assembly, similar to paclitaxel 127. Proteasome inhibitor 1. PTK inhibitor, Src 383. PTP1B inhibitor 453. PTPB inhibitor 90. R Radioprotectant 278. Reduction of oxidative stress, in vivo, increasing activities of hepatic Antioxidant, enzymes including glutathione peroxidase and superoxide dismutase 547. RNA synthesis inhibitor 695. RNA synthesis inhibitors, as an elastase inhibitor 219. S SARS-coronovirus 3CL protease inhibitor 686. Sea urchin gamete inhibitor 336. Selective antagonist of serotonin receptor 5-HT2B 641. Semaphorin inhibitor 450. Settlement inhibitor 689. Severe skin irritant 691. Skin irritant 831. Sphingomyelinase inhibitor, rat brain membrane 363.

388

Index 5 Compound Pharmacological Activity Index

Stimulator of adipogenesis, preadipocyte differentiation-inducing activity 15. Suggesting different mechanism of interaction with DNA molecules 945, 946. Superoxide anion production inhibitor 784. Synergist of antibacterial, Bacteroides fragilis 262, 460 and 288, meropenem as synergist 682, 683. Synergist of antibacterial, Stenotrophomonas maltophilia 511 and Pseudomonas aeruginosa 101, meropenem as synergist 682, 683. T Taq DNA polymerase inhibitor 804, 811. Thrombin receptor antagonist, inhibits binding of [125I]-thrombin to platelet membranes 564. Tissue regeneration stimulant 180. TNF-α-induced NF-κB activation inhibitor 341. Topoisomerase II inhibitor 192. Topoisomerase II inhibitor, with selective cytotoxicity against A549 396. Toxic, brine shrimp 10, 530, 531, 532, 533, 545. Toxic, brine shrimp Artemia larvae 371. Toxic, brine shrimp Artemia salina 373, 481, 482. Toxic, highly 211. Toxic, variety of micro- and macro-algae 485, 495, 496, 525. Toxin 211, 242, 243, 376. TPK inhibitor 283. Tubule formation inhibitor 815, 803, 816. Tyrosinase inhibitor 131. Tyrosine kinase inhibitor 815.

(The End of HAMNP Volume 7)

Tyrosine kinase inhibitor, HUVEC lysate, tyrosine kinase assay, growth inhibition assay and migration assay 803, 816. Tyrosine kinase inhibitor, TKp56lck 6. Tyrosine kinase p56lck inhibitor, ELISA-based assay, reduced enzyme activity 543. Tyrosine kinase p56lck is necessary for T-cell activation 543. U Ubiquitin-activating enzyme inhibitor 184. Used in prophylaxis of acute kidney rejection 643. Used in treating psoriasis and leishmaniasis 643. V Varitriol displayed increased potency 17. Vesicant, hmn and animal skin 86. Virus inhibitor IFV H1N1 582, 590. X Xanthine oxidase inhibitor 246, 247. Y Yrosine kinase inhibitor TKp56lck 767. α α2-Macroglobulin inhibitor 554, 550, 544. α2-plasmin inhibitor 555. α-Glucosidase inhibitor 285, 536, 577, 578.