Journal of Lipid Research, Vol. 7, 511-523, July 1966
Copyright © 1966 by Lipid Research, Inc.

Identification of mono- and dihydroxy bile acids in human feces by gas-liquid chromatography and mass spectrometry

Peter Eneroth , Bruce Gordon , Ragnar Ryhage , and Jan Sjövall

Department of Chemistry and Laboratory for Mass Spectrometry, Karolinska Institutet, Stockholm, Sweden

The mono- and disubstituted cholanoic acids present in human feces have been investigated. Extracts of feces were fractionated on silicic acid column and individual bile acids were isolated by preparative thin-layer chromatography. The isolated compounds were studied by gas-liquid chromatography of the methyl esters, partial trimethylsilyl ethers, oxidation products, and trifluoroacetates. The probable structures deduced were confirmed by gas chromatography-mass spectrometry and by comparisons with authentic compounds.

The following derivatives of 5-cholanoic acid not previously isolated from human feces were identified: 3,12-diketo, 3-keto-12-hydroxy, 3,12-dihydroxy, 3,12-dihydroxy, 3-keto-7-hydroxy, 3-hydroxy-7-keto, 3,7-dihydroxy, 3,7-dihydroxy, and 3,7-dihydroxy.

The presence of 3-keto-, 3-hydroxy-, 3-hydroxy-, 3-hydroxy-12-keto-, 3-hydroxy-12-keto-, 3,12-dihydroxy-, and 3,12-dihydroxy-5-cholanoic acids was confirmed.

Evidence was obtained for the presence of two bile acids having at least one hydroxyl group at a carbon atom other than C₃, C₇, or C₁₂.

Supplementary key words bile acids • trifluoroacetates • partial trimethylsilyl ethers • dimethylhydrazones • thin-layer chromatography • gas-liquid chromatography • mass spectrometry • identification • feces • man

Submitted on February 14, 1966
Accepted on April 5, 1966

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