title: Dehydroxylation of cholic acid at C12 and epimerization at C5 and C7 by Bacteroides species.
abstract: Freshly isolated cultures (2060) of human intestinal bacteria of the predominant flora, among them 1029 strains of saccharolytic Bacteroides species, were tested for cholic acid transformation. Eight Bacteroides strains reduced cholate to chenodeoxycholate, while 73 strains dehydroxylated at C7, producing deoxycholate. Concurrent oxidation of hydroxyl groups, mainly at C7, was seen with many strains. No strain was able to dehydroxylate simultaneously at C7 and C12. One isolate, identified as a mixed culture of Bacteroides fragilis and B. uniformis, epimerized cholic acid at C5 and simultaneously epimerized, oxidized and dehydroxylated at C7. The following transformation products were identified: 3 alpha,7 alpha,12 alpha-trihydroxy-5 alpha-cholanoic acid, 3 alpha,7 beta,12 alpha-trihydroxy-5 beta-cholanoic acid (ursocholic acid), 3 alpha,12 alpha-dihydroxy-7-keto-5 beta-cholanoic acid, 3 alpha,12 alpha-dihydroxy-5 alpha-cholanoic acid and a 3 alpha,12 alpha-dihydroxy-5 alpha-cholenoic acid. Dehydroxylating and epimerizing abilities were detected when fresh isolates were tested first for cholate transformation. They were no longer recognizable after some serial transfers. Dehydroxylation at C12 of cholate could not be demonstrated with mixed fecal cultures. The possible intermediate, however, 3 alpha,7 alpha-dihydroxy-5 beta-chol-11-enoate, was abundantly hydrogenated by stool suspensions.
mesh_terms: D001439:Bacteroides / Q000302:isolation & purification / Q000378:metabolism*; D002635:Chenodeoxycholic Acid / Q000302:isolation & purification; D019826:Cholic Acid; D002793:Cholic Acids / Q000378:metabolism*; D002849:Chromatography, Gas; D005243:Feces / Q000382:microbiology; D006801:Humans; D013058:Mass Spectrometry; D013045:Species Specificity
chemical_list: D002793:Cholic Acids; D002635:Chenodeoxycholic Acid; D019826:Cholic Acid