Briarane, Erythrane, and Aquariane Diterpenoids from the Caribbean Gorgonian <i>Erythropodium caribaeorum</i>

Taglialatela‐Scafati, Orazio; Craig, Kyle S.; Reberioux, Delphine; Roberge, Michel; Andersen, Raymond J.

doi:10.1002/ejoc.200300214

Cited by 18 publications

(10 citation statements)

References 15 publications

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“…8 Desmethyleleutherobin (5) (IC 50 20 nM) and isoeleutherobin A (7) (IC 50 50 nM) were found to be more potent than eleutherobin (IC 50 100 nM). 7 Two new natural products, caribaeorane (11) and 15-hydroxycaribaeorane (12), were identified by the isolation of their C-4 methylketal artifact, which led to a proposal for the late stages of eleutherobin biosynthesis. 9 A further investigation of a methanol extract of a cultured E. caribaeorum resulted in the isolation of a diterpene with a highly rearranged carbon skeleton, aquariolide A (13).…”

Section: Family Anthothelidaementioning

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 Anthothelidaementioning

confidence: 99%

Diterpenes from gorgonian corals

2009

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“…429 In addition to a number of known metabolites, seven new briaranes, erythrolides R-U 549-552, an erythrane, erythrolide V 553, and two aquariane-skeletoned diterpenes, aquariolides B 554 and C 555, were reported from a Caribbean collection of Erythropodium caribaeorum. 430 Aquariolide A 556, previously isolated from aquarium-grown specimens of E. caribaeorum, 431 was also identified from the organism collected in the wild. The relative stereochemistries of 549-555 were determined either by conversion to known related derivatives, or by interpretation of ROESY NMR data, while for erythrolide S 550, Mosher methodology established the absolute configuration of the 3-hydroxybutanoyl side chain as (3 S).…”

Section: Coelenteratesmentioning

confidence: 99%

Marine natural products

et al. 2005

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This review covers the literature published in 2003 for marine natural products, with 619 citations (413 for the period January to December 2003) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates and echinoderms. The emphasis is on new compounds (656 for 2003), together with their relevant biological activities, source organisms and country or origin. Biosynthetic studies or syntheses that lead to the revision of structures or stereochemistries have been included (78), including any first total syntheses of a marine natural product.

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“…Biogenetically, briarane analogues are suggested to be originated from host corals rather than the endophytic microorganisms, 6,7 while they are supposed to be generated through 3,8-cyclization of cembranoids. 8,9 The structural variation was attributed to different species or the same species collected in different seasons and at varying geographical locations. Due to the structural novelty and complex, chemists continue to engage in the discovery of the chemical diversity, with which a profile of more than 600 briarane-based derivatives has been isolated to date, and the numbers of new entities increasingly developed in recent years.…”

Section: Introductionmentioning

confidence: 99%

Fragilolides A-Q, norditerpenoid and briarane diterpenoids from the gorgonian coral Junceella fragilis

Cheng

et al. 2017

Tetrahedron

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Chemical investigation of the gorgonian coral Junceella fragilis resulted in the isolation of a new norditerpenoid fragilolide A (1), sixteen new briarane diterpenoids fragilolides B-Q (2-17), together with frajunolides H and N, and three known norcembranoids scabrolide D, sinuleptolide and 5-epi-sinuleptolide. The structures of new compounds were determined on the basis of extensive spectroscopic analysis, including the experimental and calculated ECD data and single-crystal X-ray diffraction for the configurational assignments. The structure of fragilolide A featured an unprecedented 4,13-and 7,11-fused tetracyclic norcembranoid, while the biogenetic relationships of the briarane analogues were postulated. Frajunolide H exerted significant inhibition against a panel of tumor cell lines, and six briarane diterpenoids (3, 6, 8, 12, 16, and frajunolide N) exhibited the inhibitory effects against the HBeAg express of hepatitis B virus in HepAD38 cells. In addition, sinuleptolide and 5-epi-sinuleptolide exerted the effects to inhibit NO production in RAW264.7 macrophage cells, in addition to the activation of ARE and the inhibition of NF-B expression.

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Briarane, Erythrane, and Aquariane Diterpenoids from the Caribbean Gorgonian Erythropodium caribaeorum

Abstract: Seven new diterpenoids belonging to the briarane [erythrolides R (5), S (6), T (7), and U (8)

Cited by 18 publications

References 15 publications

Diterpenes from gorgonian corals

Diterpenes from gorgonian corals

Marine natural products

Fragilolides A-Q, norditerpenoid and briarane diterpenoids from the gorgonian coral Junceella fragilis

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