title: 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.
abstract: 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.
authors.affiliation: School of Pharmaceutical Science, University of Shizuoka, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Ishida
authors.forename: N
authors.initials: N
authors.lastname: Yamamoto
authors.forename: H
authors.initials: H
authors.lastname: Nukaya
authors.forename: K
authors.initials: K
authors.lastname: Tsuji
authors.forename: T
authors.initials: T
authors.lastname: Kosuge
mesh_terms: D017607:Aluminum Compounds; D000818:Animals; D001646:Bile / Q000737:chemistry*; D002777:Cholestanols / Q000737:chemistry* / Q000302:isolation & purification; D005704:Gallbladder / Q000737:chemistry; D018020:Lithium Compounds; D008419:Materia Medica; D010084:Oxidation-Reduction; D012754:Sharks / Q000378:metabolism*
chemical_list: D017607:Aluminum Compounds; D002777:Cholestanols; D018020:Lithium Compounds; D008419:Materia Medica; C092641:chimaerol; C042073:lithium aluminum hydride