Bile acids and bile alcohols of bullfrog1
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چکیده
Gallbladder bile of the bullfrog, R a m catesbezana was found to contain a number of minor bile acids and bile alcohols in unconjugated forms. The following bile acids and bile alcohols were identified by combined gas-liquid chromatography-mass spectrometry: cholic acid, allocholic acid, 3a,7a, 12a-trihydroxy-5a-cholestan-26-oic acid, 3a,7a, 12atrihydroxy-24-methyl-5~-cholestan-26-oic acid, 3a,7a, 12a,24tetrahydroxy-5a-cholestan-26-oic acid, 3a,7a,12a,24-tetrahydroxy-5P-cholestan-26-oic acid, 3a,7a,12a,26-tetrahydroxy-5a-cholestan-27-oic acid, 3a,7a,12a,26-tetrahydroxy-5P-cholestan-27-oic acid, 3a,7a, 12a-trihydroxy27-nor-5a-cholestan-24-one, and 3a,7a, 12a-trihydroxy27-nor-5P-cholestan-24-one. These minor constituents of the bile may represent intermediates in the biosynthetic pathway of bile acids and bile alcohols in the bullfrog.Noma, Y., M. Une, K. Kihira, M. Yasuda, T. Kuramoto, and T. Hoshita. Bile acids and bile alcohols of bullfrog. J . Lzpid Res. 1980. 21: 339-346. Supplementary key words spectrometry gas-liquid chromatography . mass The bile of the bullfrog, Rana catesbeiana, has been known to contain a number of biogenetically interesting bile acid and bile alcohols. Up to now, the following major bile acid and bile alcohols have been isolated and characterized: trihydroxycoprostanic acid (3a ,7a , 12a-trihydroxy-5P-cholestan-26-oic acid) ( l ) , 5a-cyprinol(5a-cholestane-3a,7a, 12a,26,27pentol) (2), 5aand 5P-ranols (27-nor-5aand 5Pcholestane-3a,7a, 12a,24,26-pentols) (2, 3), and the four isomers at C-5 and C-24 of 26-deoxyranol (2). The major bile acid, trihydroxycoprostanic acid has been shown to be an important intermediate in the course of cholic acid (3a,7a, 12a-trihydroxy-5Pcholan-24-oic acid) biosynthesis. According to present knowledge (4) the biosynthetic pathway for cholic acid involves the transformation of cholesterol to trihydroxycoprostanic acid via 5P-cholestane-3a,7a, 12a-triol. The C,, bile acid then undergoes P-oxidation forming cholic acid with the loss of the three-carbon fragment, propionic acid. The occurrence of ranols and 26-deoxyranols as the major bile alcohols presents a metabolic question. The biosynthesis of the 27-norcholestanepolyols clearly indicates a departure from the pathway for the cholic acid production, since at some stage a single carbon atom must be lost from the cholesterol side chain. In order to better understand the formation of the CZ6 bile alcohols in the bullfrog, we have studied the minor constituents of bullfrog bile. MATERIALS AND METHODS
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