Study on the bile salt, sodium scymnol sulfate, from Rhizoprionodon acutus. IV. Structures of chimaerol and sodium chimaerol sulfate in the bile of Lamna ditropis and Rhizoprionodon acutus.

Sodium chimaerol sulfate (1) was isolated from the bile of Lamna ditropis and Rhizoprionodon acutus by chromatography on silica gel and Sephadex LH-20, together with sodium scymnol sulfates, (24R,25S)- and (24R,25R)-(+)-3 alpha,7 alpha,12 alpha,24,26-pentahydroxy-5 beta-cholestan-27-yl sodium sulfates (3 and 4) and 3, respectively. On acid hydrolysis, compound 1 afforded chimaerol (2), which was identified as (24R,25R)-(+)-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,26-pentol by direct comparison with an authentic sample, prepared by reduction of (24R,25S)-(+)-24,26-epoxy-5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol (5) with LiAlH4. The structure of 1 was concluded to be (24R,25R)-(+)-3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-yl sodium sulfate, based on the chemical transformation and spectral data.