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Journal of Lipid Research, Vol. 14, 391-399, July 1973
Copyright © 1973 by Lipid Research, Inc.

Bile acids. XXXIX. Metabolism of 5-cholestane-3ßbeta;,26-diol and 5-cholestane-3ßbeta;,7,26-triol in the rat with a bile fistula

Burton W. Noll , E. A. Doisy Jr. , and William H. Elliott

Department of Biochemistry, St. Louis University School of Medicine, St. Louis, Missouri 63104

25r-5-[5,6-³H₂]Cholestane-3ßbeta;,7,26-triol was prepared from 3ßbeta;,26-diacetoxy-5[5,6-³H₂]cholestan-7-one that was obtained from kryptogenin. Huang-Minlon reduction of the ketone provided 25r-5-[5-³H]cholestane-3ßbeta;,26-diol. Results from mass spectrometry, molecular rotation, and several types of chromatography are consonant with the assigned structures. Bile was collected for 8 days from adult male rats, with cannulated bile ducts, that had received approximately 0.8 mg of the triol or diol intraperitoneally. Bile from the first 12 hr was hydrolyzed, and the bile acids were separated by partition chromatography. The chromatographic pattern of separated bile acids was much simpler for the triol than the diol. Approximately 50% of the bile acids derived from the triol were trihydroxy allo acids (allocholic acid, 44%, and its 3ßbeta; isomer, 5.3%); only 16.4% allocholic acid was obtained from the diol. Comparable amounts of allochenodeoxycholic acid were derived from the diol and triol (21.2% and 28.2%, respectively). Unidentified metabolites in the dihydroxy acid fraction derived from the diol constitute 15.8% of chromatographed material.

Supplementary key words 25r-5-[5,6-³H₂]cholestane-3ßbeta;, 7,26-triol • 25r-5-[5-³H]cholestane-3ßbeta;,26-diol • allocholic acid • allochenodeoxycholic acid • 3ßbeta;-hydroxy allo bile acids • kryptogenin • mass spectrometry • gas-liquid chromatography

Submitted on October 2, 1972
Accepted on February 5, 1973

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