Chemical synthesis of 5beta-cholestane-3alpha, 7alpha, 24, 25-tetrol and its metabolism in the perfused rabbit liver.
5beta-[G-3H]Cholestane-3alpha, 7alpha, 24xi, 25-tetrol (IV) was synthesized via dehydration and peroxidation of 5beta-[G-3H]cholestane-3alpha, 7alpha, 25-triol. Following perfusion of the labeled compound in the isolated rabbit liver, the bile alcohol and bile acid metabolites secreted into the bile were identified by a combination of thin layer chromatography, gas-liquid chromatography, and gas-liquid chromatography/mass spectrometry. The following bile alcohols were tentatively identified: 5beta-cholest-23-ene-3alpha, 7alpha, 25-triol, 5beta-cholest-25-ene-3alpha, 7alpha, 12alpha, 24xi-tetrol, and 5beta-cholestane-3alpha, 7alpha, 12alpha, 24xi, 25-pentol. The amount of administered tetrol recovered unchanged ranged from 1 to 88%. Cholic acid was the major product, but limited amounts of chemodeoxycholic acid were also formed. The 24-hydroxyl group in the steroid side chain did not prevent 12alpha-hydroxylation.
D000818:Animals; D001646:Bile / Q000378:metabolism; D001647:Bile Acids and Salts / Q000378:metabolism; D002635:Chenodeoxycholic Acid / Q000096:biosynthesis; D002777:Cholestanols / Q000138:chemical synthesis / Q000378:metabolism*; D008099:Liver / Q000378:metabolism*; D008297:Male; D010477:Perfusion; D011817:Rabbits
D001647:Bile Acids and Salts; D002777:Cholestanols; D002635:Chenodeoxycholic Acid