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Conversion of 7-ketolithocholic acid to ursodeoxycholic acid by human intestinal anaerobic microorganisms: Interchangeability of chenodeoxycholic acid and ursodeoxycholic acid

Summary

Chenodeoxycholic acid, ursodeoxycholic acid and 7-ketolithocholic acid were incubated with human intestinal bacteria (source: 4 healthy males) at 37‡C for 72 hours in an anaerobic condition. The bile acids of the products in culture medium were identified by three independent methods, thin layer chromatography, gas-liquid chromatography and GLC-mass spectrometry.

Lithocholic acid, ursodeoxycholic acid and 7-ketolithocholic acid were observed in the culture of chenodeoxycholic acid. Lithocholic acid, chenodeoxycholic acid and 7-ketolithocholic acid were observed in the culture of ursodeoxycholic acid. Chenodeoxycholic acid and ursodeoxycholic acid were produced from 7-ketolithocholic acid. These data may suggest that chenodeoxycholic acid and ursodeoxycholic acid are interconvertible via 7-ketolithocholic acid by the mixed culture of human intestinal microorganisms under an anaerobic condition.

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References

  1. Aries V, Hill MJ: Degradation of steroids by intestinal bacteria. II. Enzymes catalysing the oxidoreduction of the 3α-, 7α- and 12α-hydroxyl groups in cholic acid, and the dehydroxylation of the 7-hydroxyl group. Biochim Biophys Acta 202: 535–543, 1970

    PubMed  CAS  Google Scholar 

  2. Gustafsson BE, Midtvedt T, Norman A: Isolated fecal microorganisms capable of 7α-dehydroxylating bile acids. J Exp Med 123: 413–432, 1966

    PubMed  Article  CAS  Google Scholar 

  3. Midtvedt T, Norman A: Anaerobic, bile acid transforming microorganisms in rat intestinal content. Acta Pathol Microbiol Scand 72: 337–344, 1968

    PubMed  CAS  Article  Google Scholar 

  4. Midtvedt T, Norman A: Bile acid transformations by microbial strains belonging to genera found in intestinal contents. Acta Pathol Microbiol Scand 71: 629–638, 1967

    PubMed  CAS  Article  Google Scholar 

  5. Hellström K, Sjövall J: Metabolism of chenodeoxycholic acid in the rabbit. Bile acids and steroids 104. Acta Chem Scand 14: 1763–1769, 1960

    Google Scholar 

  6. Salen G, Tint GS, Eliav B, Dering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest 53: 612–621, 1974

    PubMed  CAS  Google Scholar 

  7. Gallagher TF, Long WP: Partial oxidation of cholic acid. J Biol Chem 147: 131–134, 1943

    CAS  Google Scholar 

  8. Drasar BS: Cultivation of anaerobic intestinal bacteria. J Path Bact 94: 417–427, 1967

    PubMed  Article  CAS  Google Scholar 

  9. Hellström K, Sjövall J: On the origin of lithocholic and ursodeoxycholic acids in man. Bile acids and steroids 106. Acta Physiol Scand 51: 218–223, 1961

    PubMed  Article  Google Scholar 

  10. Samuelsson B: The metabolism of 7-ketolithocholic acid-24-14C in the rat. Bile acids and steroids 70. Acta Chem Scand 13: 236–240, 1959

    CAS  Google Scholar 

  11. Mahowald TA, Yin, MW, Matschiner JT, Hsia SL, Doisy EAJ, Elliott WH, Doisy EA: VIII. Metabolism of 7-ketolithocholic acid-24-14C in the rat. J Biol Chem 230: 581–588, 1958

    PubMed  CAS  Google Scholar 

  12. Hayaishi O, Slaughters C, Jakoby WB: 3-hydroxy bile acid dehydrogenase from Escherichia Freundii. J Bacteriol 79: 145–149, 1960

    PubMed  CAS  Google Scholar 

  13. Hayaishi O, Sato Y, Jakoby WB, Stohlman EF: Reversible enzymatic oxidation of bile acids. Arch Biochem Biophys 56: 554–555, 1955

    Article  CAS  Google Scholar 

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Higashi, S., Setoguchi, T. & Katsuki, T. Conversion of 7-ketolithocholic acid to ursodeoxycholic acid by human intestinal anaerobic microorganisms: Interchangeability of chenodeoxycholic acid and ursodeoxycholic acid. Gastroenterol Jpn 14, 417–424 (1979). https://doi.org/10.1007/BF02773728

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  • DOI: https://doi.org/10.1007/BF02773728

Key Words

  • bile acid
  • oxidoreduction
  • intestinal microorganisms
  • anaerobic culture