New marine diterpenoids, including a unique hydroperoxide, from a caribbean gorgonian coral of the genus pseudopterogorgia

Harvis, C. A.; Burch, Mark T.; Fenical, William

doi:10.1016/s0040-4039(00)80495-5

Cited by 38 publications

(9 citation statements)

References 6 publications

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“…115 The a configuration assigned to the isobutenyl side chain in elisabatins A and B distinguishes these metabolites from other amphilectanes previously isolated from P. elisabethae. 92,97,116 Scheme 1 Proposed biosynthesis of pseudopterosins.…”

Section: Family Gorgoniidaementioning

confidence: 99%

Diterpenes from gorgonian corals

2009

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Covering: 1995 to April 2008. Gorgonian corals continue to provide a wealth of novel structures, many of which exhibit potentially useful biological activity. Notably, the families Briareidae, Gorgoniidae and Plexauridae have been demonstrated to contain a wide variety of natural products including steroids, acetogenins, sesquiterpenes and diterpenes. The most common of the gorgonian natural products are the diterpenes, and the intent of this review is to describe such compounds isolated from gorgonian corals, with a focus on the structures of new compounds as well as their biological activity. There have been developments improving our understanding of the biosynthetic origin of selected diterpenes, and these will also be discussed. This review describes 602 new compounds from 177 articles.

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Section: Family Gorgoniidaementioning

confidence: 99%

Diterpenes from gorgonian corals

2009

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“…Sequential treatment of tobagolide with methyl iodide and sodium hydride results in intramolecular SN' displacement with reconstruction of pseudopterolide. 179,180 Two collections of P. acerosa from Tobago produced mixtures of acids that were esterified with diazomethane to obtain deoxypseudopterolide (216) and acerosolide (217) in the former collection and tobagolide (215) in the latter collection. The reported structural assignments for the pseudopterane 216 and the cembrane 217 were devoid of relevant stereochemistry and depended heavily on 2D-NMR spectroscopy.…”

Section: Pseudoplexaura Porosa (Houttuyn)mentioning

confidence: 99%

The natural products chemistry of West Indian gorgonian octocorals

1995

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Plexauddae flourish as they do nowhere in the world. Gorgonian corals (order Gorgonacea, phylum Cnidaria) are 4571 4572 A.D. RODRIGUEZ conspicuous members of most tropical and subtropical marine habitats, being the most abundant octocorals found in the West Indies. With over 195 species documented from these two major families, gorgonian octocorals represent an estimated 38% of the known fauna, l Studies of the natural products chemistry of this interesting group of marine invertebrates began in the late 1950's. Since these early investigations, numerous studies of the chemistry of gorgonian corals have been published and summarized. 2-9 This Report documents the exciting chemistry that has been generated through the investigation of gorgonian octocorals from the West Indian region.It includes only research published in refereed journals up to December, 1994. A short communication in Science by Burkholder and Burkholder in 1958, highlighting the occurrence of antibiotic substances in gorgonian corals from Puerto Rico, was used as the starting point for the present review, to This Report is not intended to be comprehensive but instead concentrates on novel marine natural products with interesting biological and pharmaceutical properties. With the exception of several unusual sterols having interesting functionalities, marine sterols, carotenoids, fatty acids, and biopolymers isolated have not been included, since they have been reviewed by specialists, l 1-15 Studies of the chemical ecology aiming at the elucidation of the defensive roles of secondary metabolites from West Indian gorgonians and the value of secondary metabolite composition as a chemotaxonomic tool are discussed. The cited articles were retrieved from computer literature searches by use of Chemical Abstracts (CA Selects), MarinLit, STN International and also NAPRALERT. Terms such as West Indian, Caribbean, gorgonian, sea whip, octocoral, and phylla names were used. The primary focus will be the structural chemistry and biological activities of the metabolites produced by a relatively small group of gorgonians found within a limited geographic area. Wherever possible, every effort was made to record the biological and pharmacological properties of new metabolites. Since marine natural products in general are often the targets of synthetic chemists, we include synthetic work, where available, on novel compounds isolated from these animals.We hope to illustrate the diversity of compounds produced by West Indian gorgonians, while highlighting their specialized ability to biosynthesize secondary metabolites with promising pharmacological activity. 16-19 NATURAL PRODUCTS CHEMISTRYGorgonian metabolites possess novel structures that are largely unknown from terrestrial sources. These animals are now recognized to produce acetogenins, sesquiterpenoids, diterpenoids, prostanoids, and, in some cases, highly functionalized steroids. 7 The chemistry of West Indian gorgonian octocorals will be presented taxonomically according to genus and species (in alphabetic...

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“…Harvis and coworkers isolated the first hydroperoxy‐pseudopterosin analogue 1 from the Caribbean gorgonian coral Pseudopterogorgia sp. (Figure ), and its structure was established by spectroscopic methods and chemical conversion.…”

Section: Gorgonaceamentioning

confidence: 99%

“…Since the discovery of the first hydroperoxyditerpenoid 1 (Figure ), a pseudopterosin analogue obtained by Harvis et al . from the Caribbean gorgonian coral Pseudopterogorgia sp., 75 diterpenoids featuring a hydroperoxy group have been obtained from various octocorals. These marine‐origin hydroperoxyditerpenoids continue to attract the attention of investigators owing to the structural complexity and interesting biological activities (e. g., cytotoxicity, anti‐inflammatory activity, antibacterial activity, and antimalarial activity) associated with numerous compounds of this type.…”

Section: Introductionmentioning

confidence: 99%

Hydroperoxyditerpenoids from Octocorals

Sheu

Peng

Fang

et al. 2019

Israel Journal of Chemistry

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The structures, names, bioactivities, and references of 75 marine diterpenoids from octocorals possessing a hydroperoxy group, including 46 cembranes, 8 eunicellins, 5 briaranes, 5 dolabellanes, 4 germacranes, 3 xenicins, 2 caryophyllanes, 1 decalin, and 1 pseudopterosin, are summarized in this review article. All the hydroperoxyditerpenoids mentioned in this review were isolated from octocorals from Alcyonacea (Briareum excavatum, Briareum polyanthes, Briareum violaceum, Briareum sp., Cespitularia sp., Cladiella tuberculosa, Cladiella sp., Clavularia inflata, Klyxum simplex, Lemnalia sp., Lobophytum crassum, Lobophytum sp., Nephthea pacifica, Sarcophyton cherbonnieri, Sarcophyton crassocaule, Sarcophyton glaucum, Sarcophyton mililatensis, Sarcophyton trocheliophorum, Sarcophyton sp., Sinularia arborea, Sinularia erecta, Sinilaria flexibilis, Sinularia gibberosa, Sinularia manaarensis, Xenia umbellata) and Gorgonacea (Astrogorgia sp., Eunicea calyculata, Eunicea pinta, Eunicea succinea, Eunicea sp., Pseudopterogorgia sp.). Among these isolates, 41 compounds exhibited potential biomedical activities, including cytotoxicity, antimalarial activity, anti‐inflammatory activity, and antibacterial activity.

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New marine diterpenoids, including a unique hydroperoxide, from a caribbean gorgonian coral of the genus pseudopterogorgia

Cited by 38 publications

References 6 publications

Diterpenes from gorgonian corals

Diterpenes from gorgonian corals

The natural products chemistry of West Indian gorgonian octocorals

Hydroperoxyditerpenoids from Octocorals

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