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-3beta,5alpha,6alpha,25-tetrol (1), cholesta-8(14)-en-3beta,5alpha,6alpha,25-tetrol (2), cholesta-8,24-dien-3beta,5alpha,6alpha-triol (3), and cholesta-8(14),24-dien-3beta,5alpha,6alpha-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 microg/disc, respectively.
Sauleau
Pierre
P
Laboratoire de Chimie, UMR 5154 CNRS, Muséum National d' Histoire Naturelle, 63 rue Buffon, 75231 Paris Cedex 05, France.
Bourguet-Kondracki
Marie-Lise
ML
D000818:Animals; D002774:Cholestadienes / Q000032:analysis / Q000737:chemistry; D006914:Hydroxysteroids / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D019156:Indian Ocean; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry*
D002774:Cholestadienes; D006914:Hydroxysteroids