Bioactive (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids from the South China Sea gorgonian Dichotella gemmacea

Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N-S (1-6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7-10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by t...

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Bibliographic Details
Published in:Marine drugs 2011-08, Vol.9 (8), p.1403-1418
Main Authors: Li, Cui, La, Ming-Ping, Sun, Peng, Kurtan, Tibor, Mandi, Attila, Tang, Hua, Liu, Bao-Shu, Yi, Yang-Hua, Li, Ling, Zhang, Wen
Format: Article
Language:English
Subjects:
Animals
Anthozoa - chemistry
Anti-Infective Agents - chemistry
Anti-Infective Agents - isolation & purification
Anti-Infective Agents - pharmacology
Bacteria - drug effects
biological activity
briarane diterpenoids
Cell Line, Tumor
China
Dichotella gemmacea
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Fungi - drug effects
gorgonian
Humans
Magnetic Resonance Spectroscopy - methods
Models, Molecular
Oceans and Seas
structure elucidation
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Summary:Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N-S (1-6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7-10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7-10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli.
ISSN:1660-3397
1660-3397
DOI:10.3390/md9081403