Abstract
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.
Highlights
Briarane-type diterpenoids are a group of highly oxidized secondary metabolites reported from marine organisms, from octocorals [1]
Chemical investigation on the species led to the isolation and structure elucidation of nineteen new briaranes, namely gemmacolides G–Y, together with eight known analogues, praelolide, juncin O, junceellolide C, juncenolide D and J, and juncins R, S and U [10,11,12]
Gemmacolides J, V and Y were more active than the positive control adriamycin against A549 cells [10,12], demonstrating a potent activity in tumor cell growth inhibition
Summary
Briarane-type diterpenoids are a group of highly oxidized secondary metabolites reported from marine organisms, from octocorals [1]. Chemical investigation on the species led to the isolation and structure elucidation of nineteen new briaranes, namely gemmacolides G–Y, together with eight known analogues, praelolide, juncin O, junceellolide C, juncenolide D and J, and juncins R, S and U [10,11,12]. Isolation of the compounds from natural sources is a better choice for the chemical and biological study of such cluster of compounds This promotes repeated collections of gorgonian D. gemmacea, a promising source of briarane diterpenoids.
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