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Journal of Lipid Research, Vol 28, 895-899, Copyright © 1987 by Lipid Research, Inc.

ARTICLES

Identification of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25,26- hexol in human urine

T Hiraoka, K Kihira, G Kajiyama, T Kuramoto and T Hoshita
First Department of Internal Medicine, Hiroshima University School of Medicine, Japan.

A new bile alcohol, 5 beta-cholestanehexol, was identified in the urine of healthy humans as the glucuronide. The bile alcohol glucuronide fraction was isolated by an ion exchange chromatography on piperidinohydroxypropyl Sephadex LH-20. After enzymatic hydrolysis, the bile alcohols were converted into trimethylsilyl ether derivatives and analyzed by a combination of gas-liquid chromatography and mass spectrometry. The major bile alcohol was 27-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25-pentol. As minor constituents the following C26 and C27 bile alcohols were identified: 27-nor-5 beta- cholestane-3 alpha,7 alpha,12 alpha,24,25,26-hexol, 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25-pentol, 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,26-pentol, 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25,26-pentol. In addition to these bile alcohols, a new bile alcohol was identified as a sixth component of the urinary bile alcohols. The structure was assigned as (24S)-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25,26-hexol by the direct comparison of mass spectral data and chromatographic properties with synthetic standard. The average daily excretion of the new bile alcohol was 28.6 micrograms and 3.0% of the total bile alcohols. The presence of 27-nor-5 beta- cholestane-3 alpha,7 alpha,12 alpha,24,25-pentol and 27-nor-5 beta- cholestane-3 alpha,7 alpha,12 alpha,24,25,26-hexol suggests that 26- hydroxylation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25- pentol is most likely for the biosynthesis of this new bile alcohol.
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				M. Une, S. Takenaka, T. Kuramoto, K. Fujimura, T. Hoshita, and K. Kihira Structural and biosynthetic studies of a principal bile alcohol, 27-nor-5{beta}-cholestane-3{alpha},7{alpha},12{alpha},24,25-pentol, in human urine J. Lipid Res., October 1, 2000; 41(10): 1562 - 1567. [Abstract] [Full Text]