A New Bile Acid Conjugate, Ciliatocholic Acid, from Bovine Gall Bladder Bile1

Abstract

This study was carried out to investigate the occurrence of ciliatocholic acid in bovine gall bladder bile. Ciliatocholic acid was synthesized according to the method described by Bergstrom and Norman for the synthesis of taurocholic acid. Elemental analysis, melting point, and the infrared spectrum of this substance were determined. An isolation procedure for ciliatocholic acid was established by stepwise elution with an HCl-ethanol solvent system using a Dowex-1 anion exchange resin column chromatographic technique. Ciliatocholic acid amounting to 158 [ig (as ciliatine) per 100 ml of gall bladder bile was found in the fraction eluted with 0.01 N HC1 in 50% ethanol. This compound was purified by preparative thin-layer chromatography and confirmed to be ciliatocholic acid from the hydrolytic stability, phosphorus determi-nation, and chromatographic behavior. Thus, bovine gall bladder bile contains a small amount of ciliatocholic acid. The phosphonic acid analog of phosphoryl-•ethanolamine, taurine and /)-alanine, ciliatine {2-aminoethylphosphonic acid) occurs free and as a major constituent of the phospholipid of protozoa (1—3), marine (4) and fresh water invertebrates (5, 6) and mammalian tissues {7-9). Since the isolation of ciliatine, six other-aminophosphonic acids structurally related t