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Tamosterone Sulfates: A C-14 Epimeric Pair of Polyhydroxylated Sterols from a New Oceanapiid Sponge Genus
Xiong Fu1, Maria L. G. Ferreira, Francis J. Schmitz
1Department of Chemistry and Biochemistry, University of Oklahoma, Norman, Oklahoma 73019, and National Institute of Water and Atmospheric Research (NIWA), Private Bag 109-695, Newmarket, Auckland, New Zealand.
Abstract:
Two novel, C-14 epimeric polyhydroxylated 15-keto steroid sulfates, tamosterone sulfate and 14beta-tamosterone sulfate (1 and 2), were isolated from a sponge belonging to a new genus collected in Yap, Federated States of Micronesia. Their structures were assigned by analysis of spectroscopic data and chemical conversions. 14beta-Tamosterone sulfate (2) has the rare naturally occurring C/D cis ring fusion and is the less stable epimer based on equilibration studies. Both compounds possess side-chain substitution patterns not observed previously in marine sterols.