Novel polyhydroxysterols from the Red Sea marine sponge Lamellodysidea herbacea

Chemical investigation of the dichloromethane extract of the Red Sea marine sponge Lamellodysidea herbacea led to the isolation of four novel polyhydroxysteroids: cholesta-8-en-3 beta,5 alpha,6 alpha,25-tetrol (1), cholesta-8(14)-en-3 beta,5 alpha,6 alpha,25-tetrol (2), cholesta-8,24-dien-3 beta,5 alpha,6 alpha-triol (3), and cholesta-8(14),24-dien-30,5 alpha,6 alpha-triol (4). Their structures were identified through 1D and 2D NMR studies. Relative stereochemistries were established by analysis of chemical shifts, coupling constants, and NOESY correlations. Compounds 3-4 showed antifungal activity against Candida tropicalis, with an inhibition diameter of 13 and 11 mm at 10 mu g/disc, respectively. (c) 2005 Elsevier Inc. All rights reserved.