Ophirasterol, a new C31 sterol from the marine sponge Topsentia ophiraphidites

被引:24
作者
Calderón, GJ
Castellanos, L
Duque, C
Echigo, S
Hara, N
Fujimoto, Y
机构
[1] Univ Nacl Colombia, Dept Quim, Bogota 14490, Colombia
[2] Tokyo Inst Technol, Dept Chem & Mat Sci, Meguro Ku, Tokyo 1528551, Japan
关键词
marine sterols; Topsentia ophiraphidites; ophirasterol; C-31; sterols; Caribbean sponges; orthoester claisen rearrangement; stereochemistry;
D O I
10.1016/j.steroids.2003.11.001
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Analysis of the sterol fraction obtained from the Colombian Caribbean sponge Topsentia ophiraphidites revealed that this sponge is a rich source of C-30 and C-31 sterols. Among them, a new C-31 sterol, named ophirasterol, was isolated, and its structure was established as (22E,24R)-24-(1-buten-2-yl)cholesta-5,22-dien-3beta-oI (1) by spectral means and comparison with synthetic C-24 epimers with known configuration. Other isolated C-30 and C-31 sterols were the known 24-ethyl-24-methyl-22-dehydrocholesteroI (2), 24-isopropyl-22-dehydrocholesterol (3), 24-isopropyjcholesterol (4), 24-ethyl-24-methylcholesterol (5), 24-isopropenyl-25-methyl-22-dehydrocholesteroI (6) and 24-isopropenyl-25-methylcholesteroI (7), and 24-isopropenyl-22-dehydrocholesteroI (8). (C) 2003 Elsevier Inc. All rights reserved.
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页码:93 / 100
页数:8
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