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Journal of Lipid Research, Vol 26, 298-305, Copyright © 1985 by Lipid Research, Inc.

ARTICLES

Synthesis and structure of 26 (or 27)-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24S,25 xi-pentol isolated from the urine and feces of a patient with sitosterolemia and xanthomatosis

B Dayal, GS Tint, V Toome, AK Batta, S Shefer and G Salen

The urine and feces of a patient with the rare inherited lipid storage disease, sitosterolemia and xanthomatosis, were analyzed. Substantial quantities of C26-bile alcohol, 26 (or 27)-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24S,25 xi-pentol along with 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24-tetrol, 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol, 5 beta-cholestane-3 alpha,7 alpha,12 alpha,24R,25- pentol, and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25,26-pentol were found. The structure of the C26-bile alcohol was confirmed by direct comparison (gas-liquid chromatography-mass spectrometry and thin- layer chromatography) with a standard sample synthesized from cholic acid. The configurational assignment at C-24 was determined by lanthanide-induced circular dichroism Cotton effect measurements. The increased excretion of these C26- and C27-bile alcohols suggests an abnormality of bile acid biosynthesis in this disease.
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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]