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Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, China
Department of Organic Chemistry, University of Debrecen, POB 20, 4010 Debrecen, Hungary
* Authors to whom correspondence should be addressed.
Received: 1 July 2011; in revised form: 28 July 2011 / Accepted: 8 August 2011 / Published: 16 August 2011
Abstract: 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.
Keywords: briarane diterpenoids; biological activity; structure elucidation; gorgonian; Dichotella gemmacea
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MDPI and ACS Style
Li, C.; La, M.-P.; Sun, P.; Kurtan, T.; Mandi, A.; Tang, H.; Liu, B.-S.; Yi, Y.-H.; Li, L.; Zhang, W. Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea. Mar. Drugs 2011, 9, 1403-1418.
Li C, La M-P, Sun P, Kurtan T, Mandi A, Tang H, Liu B-S, Yi Y-H, Li L, Zhang W. Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea. Marine Drugs. 2011; 9(8):1403-1418.
Li, Cui; La, Ming-Ping; Sun, Peng; Kurtan, Tibor; Mandi, Attila; Tang, Hua; Liu, Bao-Shu; Yi, Yang-Hua; Li, Ling; Zhang, Wen. 2011. "Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea." Mar. Drugs 9, no. 8: 1403-1418.