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Mar. Drugs 2013, 11(5), 1565-1582; doi:10.3390/md11051565
Article

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

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2,*  and 1,*
1 Research Center for Marine Drugs, and Department of Pharmacology, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, China 2 Department of Urology, Changhai Hospital, Second Military Medical University, 168 Chang-Hai Road, Shanghai 200003, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 1 March 2013 / Revised: 7 April 2013 / Accepted: 11 April 2013 / Published: 15 May 2013
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Abstract

Eighteen new 11,20-epoxy-3Z,5E-dien briaranes, gemmacolides AA–AR (118), 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 13, 5, 6, 812, and 1419 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.
Keywords: structure activity relationship; briarane diterpenoids; biological activity; Dichotella gemmacea; gorgonian structure activity relationship; briarane diterpenoids; biological activity; Dichotella gemmacea; gorgonian
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Li, C.; Jiang, M.; La, M.-P.; Li, T.-J.; Tang, H.; Sun, P.; Liu, B.-S.; Yi, Y.-H.; Liu, Z.; Zhang, W. 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. Mar. Drugs 2013, 11, 1565-1582.

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