Chemistry and tumor cell growth inhibitory activity of 11,20-epoxy-3Z,5(6)E-diene briaranes from the South China Sea gorgonian Dichotella gemmacea

Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA-AR (1-18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spec...

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Bibliographic Details
Published in:Marine drugs 2013-05, Vol.11 (5), p.1565-1582
Main Authors: Li, Cui, Jiang, Mei, La, Ming-Ping, Li, Tie-Jun, Tang, Hua, Sun, Peng, Liu, Bao-Shu, Yi, Yang-Hua, Liu, Zhiyong, Zhang, Wen
Format: Article
Language:English
Subjects:
Animals
Anthozoa - chemistry
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
biological activity
briarane diterpenoids
Cell Line, Tumor
China
Dichotella gemmacea
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Drug Screening Assays, Antitumor
gorgonian
Humans
Neoplasms - drug therapy
Neoplasms - pathology
Oceans and Seas
Spectrum Analysis
Structure-Activity Relationship
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Summary:Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA-AR (1-18), were isolated together with three known analogs, dichotellides F (19) and I (20), and juncenolide C (21), from the South China Sea gorgonian Dichotella gemmacea. The structures of the compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was determined based on the ECD experiment. In the in vitro bioassay, compounds 1-3, 5, 6, 8-12, and 14-19 exhibited different levels of growth inhibition activity against A549 and MG63 cell lines. Preliminary structure-activity analysis suggests that 12-O-isovalerate may increase the activity whereas 13- or 14-O-isovalerate may decrease the activity. Contribution of substitutions at C-2 and C-16 remains uncertain.
ISSN:1660-3397
1660-3397
DOI:10.3390/md11051565