Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus

FEMS Microbiol Lett. 2002 Mar 5;208(2):197-202. doi: 10.1111/j.1574-6968.2002.tb11081.x.


Eubacterium ramulus, a flavonoid-degrading anaerobic bacterium from the human gastrointestinal tract, was tested for its ability to transform the isoflavonoids genistein-7-O-glucoside (genistin), genistein and daidzein. Genistein was completely degraded by E. ramulus via 6'-hydroxy-O-desmethylangolensin to 2-(4-hydroxyphenyl)-propionic acid. Dihydrogenistein was neither observed as an intermediate in this transformation nor converted itself by growing cells or cell-free extracts of E. ramulus. Genistein-7-O-glucoside was partially transformed by way of genistein to the product 2-(4-hydroxyphenyl)-propionic acid. Daidzein was in part degraded to O-desmethylangolensin, the corresponding metabolite to 6'-hydroxy-O-desmethylangolensin. The hydroxyl group in position 6' of O-desmethylangolensin is crucial for further degradation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Eubacterium / metabolism*
  • Genistein / chemistry
  • Genistein / metabolism*
  • Isoflavones / chemistry
  • Isoflavones / metabolism*
  • Models, Molecular


  • Isoflavones
  • genistin
  • daidzein
  • Genistein