Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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
石田 均司山本 信糠谷 東雄辻 邦郎小菅 卓夫
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1994 年 42 巻 12 号 p. 2514-2517

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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)-(+)-3α, 7α, 12α, 24, 26-pentahydroxy-5β-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)-(+)-5β-cholestane-3α, 7α, 12α, 24, 26-pentol by direct comparison with an authentic sample, prepared by reduction of (24R, 25S)-(+)-24, 26-epoxy-5β-cholestane-3α, 7α, 12α, 27-tetrol (5) with LiAlH4. The structure of 1 was concluded to the (24R, 25R)-(+)-3α, 7α, 12α, 24-tetrahydroxy-5β-cholestan-26-yl sodium sulfate, based on the chemical transformation and spectral data.

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