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Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus.
FEMS Microbiol Lett. 2002 Mar 05; 208(2):197-202.FM

Abstract

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.

Authors+Show Affiliations

Department of Gastrointestinal Microbiology, German Institute of Human Nutrition, Arthur-Scheunert-Allee 114-116, 14558 Bergholz-Rehbrücke, Germany.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

11959436

Citation

Schoefer, Lilian, et al. "Anaerobic C-ring Cleavage of Genistein and Daidzein By Eubacterium Ramulus." FEMS Microbiology Letters, vol. 208, no. 2, 2002, pp. 197-202.
Schoefer L, Mohan R, Braune A, et al. Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. FEMS Microbiol Lett. 2002;208(2):197-202.
Schoefer, L., Mohan, R., Braune, A., Birringer, M., & Blaut, M. (2002). Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. FEMS Microbiology Letters, 208(2), 197-202.
Schoefer L, et al. Anaerobic C-ring Cleavage of Genistein and Daidzein By Eubacterium Ramulus. FEMS Microbiol Lett. 2002 Mar 5;208(2):197-202. PubMed PMID: 11959436.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. AU - Schoefer,Lilian, AU - Mohan,Ruchika, AU - Braune,Annett, AU - Birringer,Marc, AU - Blaut,Michael, PY - 2002/4/18/pubmed PY - 2002/8/20/medline PY - 2002/4/18/entrez SP - 197 EP - 202 JF - FEMS microbiology letters JO - FEMS Microbiol. Lett. VL - 208 IS - 2 N2 - 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. SN - 0378-1097 UR - https://www.unboundmedicine.com/medline/citation/11959436/Anaerobic_C_ring_cleavage_of_genistein_and_daidzein_by_Eubacterium_ramulus_ L2 - https://academic.oup.com/femsle/article-lookup/doi/10.1111/j.1574-6968.2002.tb11081.x DB - PRIME DP - Unbound Medicine ER -