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. 2013 Mar 4;18(3):2895-903.
doi: 10.3390/molecules18032895.

A new 5α,8α-Epidioxysterol from the soft coral Sinularia gaweli

Wei-Hsuan Yen  1 , Wu-Fu Chen, Ching-Hsiao Cheng, Chang-Feng Dai, Mei-Chin Lu, Jui-Hsin Su, Yin-Di Su, Yu-Hsin Chen, Yu-Chia Chang, Yung-Husan Chen, Jyh-Horng Sheu, Chan-Hsing Lin, Zhi-Hong Wen, Ping-Jyun Sung
Affiliations

A new 5α,8α-Epidioxysterol from the soft coral Sinularia gaweli

Wei-Hsuan Yen et al. Molecules. .

Abstract

A new sterol, (22R,23R,24R)-5α,8α-epidioxy-22,23-methylene-24-methyl-cholest-6,9(11)-dien-3β-ol (1), and two known sterols, (22R,23R,24R)-5α,8α-epidioxy-22,23-methylene-24-methylcholest-6-en-3β-ol (2) and 24-methylenecholestane-1α,3β,5α, 6β,11α-pentol (3), were isolated from the soft coral Sinularia gaweli. The structure of sterol 1 was established by spectroscopic methods and by comparison of the spectral data with those of known analogues. The cytotoxicity of sterols 1-3 towards various tumor cells is reported.

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Figures

Figure 1
Figure 1
The soft coral Sinularia gaweli and the structures of (22R,23R,24R)-5α,8α-epidioxy-22,23-methylene-24-methylcholest-6,9(11)-dien-3β-ol (1), (22R,23R,24R)-5α,8α-epidioxy-22,23-methylene-24-methylcholest-6-en-3β-ol (2) and 24-methylenecholestane-1α,3β,5α,6β,11α-pentol (3).
Figure 2
Figure 2
The 1H–1H COSY and selective HMBC correlations (protons→quaternary carbons) for sterol 1.
Figure 3
Figure 3
The 1H and 13C-NMR chemical shifts of the side-chain methyl groups of epidioxysterols 1 and 2 and synthetic isomers of demethylgorgosterols [4,18,19].
See this image and copyright information in PMC

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