Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus.
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.
Schoefer
Lilian
L
Department of Gastrointestinal Microbiology, German Institute of Human Nutrition, Arthur-Scheunert-Allee 114-116, 14558 Bergholz-Rehbrücke, Germany.
Mohan
Ruchika
R
Braune
Annett
A
Birringer
Marc
M
Blaut
Michael
M
D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D005051:Eubacterium / Q000378:metabolism*; D019833:Genistein / Q000737:chemistry / Q000378:metabolism*; D007529:Isoflavones / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular
D007529:Isoflavones; C040641:genistin; C004742:daidzein; D019833:Genistein