Study on the bile salt, sodium scymnol sulfate, from Lamna distropis. III. The structures of a new sodium scymnol sulfate and new anhydroscymnols

Article abstract of DOI:10.1248/cpb.40.864

Two sodium scymnol sulfates, 1 and 2, were isolated by two steps of chromatography from the bile of Lamna ditropis. Compound 2 was identified as (24R,25S)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate and the structure of 1 was determined to be (24R,25R)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate, based on the spectral data and chemical transformations. Based on the physical data, the structures of two new anhydroscymnols, 3 and 4, prepared from 1 by alkaline degradation with aqueous potassium hydroxide, were established as (24R,25R)-(+)-24,26-epoxy-5β-cholestane-3α,7α,12α,27-tetrol and (24R)-(+)-26,27-epoxy-5β-cholestane-3α,7α,12α,24-tetrol, respectively. The other shark bile constituents were also analyzed, and the hydrolysis of the sulfate ester function of 1 and 2 was examined.

Full text of DOI:10.1248/cpb.40.864

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