Polyhydroxylated steroids from the soft coral Sinularia dissecta

A repeated silica gel column chromatography followed by HPLC purification on the methanol extract of marine soft coral Sinularia dissecta, resulted in the isolation of fifteen polyhydroxylated steroids (1-15), involving six new C- 18 functionalized steroids, 3 beta-acetoxy-1 alpha, 11 alpha-dihydroxygorgost-5-en- 18-oic acid (1), gorgost-5-en-1 alpha,3 beta,11 alpha, 18-tetrol (2), 18-acetoxy-1 alpha,3 beta, 11 alpha-trihydroxygorgost-5-ene (3), 24(S)-3 beta-acetoxy- 1 alpha, 11 alpha-dihydroxyergost-5-en- 18-oic acid (4), 24(S)-ergost-5-en- 1 alpha,3 beta, 11 alpha, 18-tetrol (5), and dissectolide (6). The structures of the new compounds were determined on the basis of extensive spectroscopic data (IR. MS, (1)H and (13)C NMR, HMQC, HMBC, and NOESY) analysis. Compound 6 was found as an unusual sterol bearing a lactone functionality. (c) 2005 Elsevier Inc. All rights reserved.