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Lobocrassins A–E: New Cembrane-Type Diterpenoids from the Soft Coral Lobophytum crassum
Graduate Institute of Marine Biotechnology, National Dong Hwa University, Pingtung 944, Taiwan
National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan
Division of Marine Biotechnology, Asia-Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung 804, Taiwan
Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan
Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan
Department of Pharmacy, Tajen University, Pingtung 907, Taiwan
Tsuzuki Institute for Traditional Medicine, College of Pharmacy, China Medical University, Taichung 404, Taiwan
Department of Life Science and Institute of Biotechnology, National Dong Hwa University, Hualien 974, Taiwan
Department of Sport, Health, and Leisure, Cheng Shiu University, Kaohsiung 833, Taiwan
* Author to whom correspondence should be addressed.
Received: 5 July 2011; in revised form: 17 July 2011 / Accepted: 28 July 2011 / Published: 5 August 2011
Abstract: Five new cembrane-type diterpenoids, lobocrassins A–E (1–5), were isolated from the soft coral Lobophytum crassum. The structures of cembranes 1–5 were established by spectroscopic and chemical methods and by comparison of the spectral data with those of known cembrane analogues. Lobocrassin A (1) is the first cembranoid possessing an α-chloromethyl-α-hydroxy-γ-lactone functionality and is the first chlorinated cembranoid from soft corals belonging to the genus Lobophytum. Lobocrassins B (2) and C (3) were found to be the stereoisomers of the known cembranes, 14-deoxycrassin (6) and pseudoplexaurol (7), respectively. Lobocrassin B (2) exhibited modest cytotoxicity toward K562, CCRF-CEM, Molt4, and HepG2 tumor cells and displayed significant inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.
Keywords: lobocrassin; cembrane; Lobophytum crassum; cytotoxicity; superoxide anion; elastase
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Kao, C.-Y.; Su, J.-H.; Lu, M.-C.; Hwang, T.-L.; Wang, W.-H.; Chen, J.-J.; Sheu, J.-H.; Kuo, Y.-H.; Weng, C.-F.; Fang, L.-S.; Wen, Z.-H.; Sung, P.-J. Lobocrassins A–E: New Cembrane-Type Diterpenoids from the Soft Coral Lobophytum crassum. Mar. Drugs 2011, 9, 1319-1331.
Kao C-Y, Su J-H, Lu M-C, Hwang T-L, Wang W-H, Chen J-J, Sheu J-H, Kuo Y-H, Weng C-F, Fang L-S, Wen Z-H, Sung P-J. Lobocrassins A–E: New Cembrane-Type Diterpenoids from the Soft Coral Lobophytum crassum. Marine Drugs. 2011; 9(8):1319-1331.
Kao, Chia-Ying; Su, Jui-Hsin; Lu, Mei-Chin; Hwang, Tsong-Long; Wang, Wei-Hsien; Chen, Jih-Jung; Sheu, Jyh-Horng; Kuo, Yueh-Hsiung; Weng, Ching-Feng; Fang, Lee-Shing; Wen, Zhi-Hong; Sung, Ping-Jyun. 2011. "Lobocrassins A–E: New Cembrane-Type Diterpenoids from the Soft Coral Lobophytum crassum." Mar. Drugs 9, no. 8: 1319-1331.