Elsevier

Tetrahedron

Volume 51, Issue 45, 6 November 1995, Pages 12293-12300
Tetrahedron

Downeyoside A and B, Two New Sulphated Steroid Glucuronides from the Starfish Henricia downeyae

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Abstract

Two new sulphated polyhydroxylated steroid glucuronides. downeyoside A and B (1, 2), C-24 methyl epimers possessing an ethereal ring linking C-16 to C-22 of the steroid, were isolated from the starfish Henricia downeyae collected from the Gulf of Mexico. Their structures were determined by spectral analysis and the stereochemistry of the highly oxygenated steroid side chain was derived from NMR data combined with molecular dynamics calculation. Compounds 1 and 2 were tested against non-small-cell lung human carcinoma cells and found to be cytotoxic with IC50 of 60 μg/ml and 36 μg/ml, respectively.

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