Journal
TETRAHEDRON
Volume 57, Issue 18, Pages 3885-3890Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00259-9
Keywords
biologically active compounds; enzyme inhibitors; marine metabolites; steroids and sterols
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Two inhibitors of membrane-type matrix metalloproteinase (MT1-MMP) were isolated from a marine sponge Cribrochalinasp. Their structures were elucidated as unusual phosphorylated sterol sulfates by spectroscopic and chemical methods. One of the sterol sulfates was found to be identical to haplosamate A, whose structure was previously proposed to be a steroidal sulfamate ester, which led to structure revisions of both haplosamates A and B. The absolute stereochemistry of haplosamate A was determined by chemical transformation and the modified Mosher's method. The sterol sulfates inhibited MT1-MMP with IC50 values of 150 and 160 mug/mL, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.
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