Polyhydroxysteroids from the Far-Eastern starfishCtenodiscus crispatus

Russian Chemical Bulletin
1994.0

Abstract

In continuation of the study on steroid fractions of Far-Eastern starfish species, five polyhydroxysteroids were isolated from the starfish Ctenodiscus crispatus. Four of them are new: 5α-cholesta-3β,5,6β,15α,16β,25,26-heptaol, 24-ethyl-5α-cholesta-3β,5,6β,15α,28,29-heptaol-29-sulfate, (22E)-24-methyl-5α-cholest-22-ene-3β,5,6β,15α,25,26-hexaol-26-sulfate, and 24-propyl-5α-cholesta-3β,5,6β,8,15α,28,29-heptaol; the fifth is the known 5α-cholesta-3β,5,6β,15α,16β,26-hexaol. Their structures were determined mainly by 1H and 13C NMR spectroscopy (including J-modulation and nuclear Overhauser effect experiments), and fast atom bombardment mass spectrometry (FAB-MS). Compound 2 was isolated as a 1:1 mixture of C(25)-epimers. Compound 3, a potassium salt, has an unusual side chain with a hydroxy group at C(28) and a sulfated hydroxy group at C(29). Compound 4 is a mixture of potassium and sodium salts, whose structure was deduced from the NMR spectra of its desulfated analog. The structure of compound 1 was confirmed by comparison with a known steroid from Luidia maculata, and other compounds were elucidated by analyzing NMR signal differences, comparing with model compounds, and using data from desulfated derivatives.

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