Open AccessAnaerobic C‐ring cleavage of genistein and daidzein by Eubacterium ramulus
Author(s) -
Schoefer Lilian,
Mohan Ruchika,
Braune Annett,
Birringer Marc,
Blaut Michael
Publication year - 2002
Publication title -
fems microbiology letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.899
H-Index - 151
eISSN - 1574-6968
pISSN - 0378-1097
DOI - 10.1111/j.1574-6968.2002.tb11081.x
Subject(s) - genistein , daidzein , genistin , metabolite , eubacterium , chemistry , biotransformation , biochemistry , flavonoid , isoflavones , stereochemistry , biology , bacteria , enzyme , endocrinology , antioxidant , genetics
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.