Bile acids. LXVII. The major bile acids of Varanus monitor

Abstract

The major bile acids of gall bladder bile of Varanus monitor have been separated by thin-layer chromatography and shown to be derivatives of taurine. After alkaline hydrolysis, the free acids were separated by thin-layer and partition chromatography. Identification or characterization of the free acids was facilitated by gas-liquid chromatography and gas-liquid chromatography-mass spectometry of the methyl esters or methyl ester-trimethylsilyl ethers. About 13% of the total bile acids was represented by the C24 acids cholic, deoxycholic, allocholic, chenodeoxycholic, and 12-oxo-3 alpha-hydroxy-5 beta-cholanic acids, of which cholic acid constituted about 50%. The remainder of the bile acids consisted of eight C27 acids of which varanic acid was the major constituent; an isomer of varanic acid and 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestanoic acid were also identified. By chromatographic behavior and mass spectral fragmentation, the structures of four C27 acids with unsaturated side chains were elucidated as follows: 3 alpha, 7 alpha-dihydroxy-5 beta-cholest-23-enoic, 3 alpha, 7 alpha-dihydroxy-5 beta-cholest-24-enoic, 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholest-23-enoic, and 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholest-24-enoic acids. Similarly, the structure of the 12-deoxy analog of varanic acid, 3 alpha, 7 alpha, 24 xi-trihydroxy-5 beta-cholestanoic acid, was suggested for the component that constituted 7% of the total.