Ishida H, Yamamoto N, Nukaya H, Tsuji K, Kosuge T
School of Pharmaceutical Science, University of Shizuoka, Japan.
Chem Pharm Bull (Tokyo). 1994 Dec;42(12):2514-7. doi: 10.1248/cpb.42.2514.
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.
通过硅胶柱色谱和葡聚糖凝胶LH - 20柱色谱，从长鳍鲭鲨（Lamna ditropis）和尖吻斜锯牙鲨（Rhizoprionodon acutus）的胆汁中分离出硫酸嵌合体醇钠（1），同时还得到了硫酸鲨胆醇钠、（24R，25S）-和（24R，25R）-（+）-3α，7α，12α，24，26 - 五羟基 - 5β - 胆甾烷 - 27 - 基硫酸钠（3和4）以及3。化合物1经酸水解后得到嵌合体醇（2），通过与用氢化铝锂还原（24R，25S）-（+）-24，26 - 环氧 - 5β - 胆甾烷 - 3α，7α，12α，27 - 四醇（5）制备的标准样品直接比较，鉴定为（24R，25R）-（+）-5β - 胆甾烷 - 3α，7α，12α，24，26 - 五醇。基于化学转化和光谱数据，确定1的结构为（24R，25R）-（+）-3α，7α，12α，24 - 四羟基 - 5β - 胆甾烷 - 26 - 基硫酸钠。
