An NADH-Dependent Reductase from Eubacterium ramulus Catalyzes the Stereospecific Heteroring Cleavage of Flavanones and Flavanonols.

Applied and Environmental Microbiology
Annett BrauneMichael Blaut

Abstract

The human intestinal anaerobe Eubacterium ramulus is known for its ability to degrade various dietary flavonoids. In the present study, we demonstrate the cleavage of the heterocyclic C-ring of flavanones and flavanonols by an oxygen-sensitive NADH-dependent reductase, previously described as enoate reductase, from E. ramulus This flavanone- and flavanonol-cleaving reductase (Fcr) was purified following its heterologous expression in Escherichia coli and further characterized. Fcr cleaved the flavanones naringenin, eriodictyol, liquiritigenin, and homoeriodictyol. Moreover, the flavanonols taxifolin and dihydrokaempferol served as substrates. The catalyzed reactions were stereospecific for the (2R)-enantiomers of the flavanone substrates and for the (2S,3S)-configured flavanonols. The enantioenrichment of the nonconverted stereoisomers allowed for the determination of hitherto unknown flavanone racemization rates. Fcr formed the corresponding dihydrochalcones and hydroxydihydrochalcones in the course of an unusual reductive cleavage of cyclic ether bonds. Fcr did not convert members of other flavonoid subclasses, including flavones, flavonols, and chalcones, the latter indicating that the reaction does not involve a chalcone in...Continue Reading

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Citations

Dec 3, 2020·PloS One·Gina Paola Rodriguez-CastañoAlejandro Acosta-González
Oct 3, 2020·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Rebeca Santes-PalaciosJesús Javier Espinosa-Aguirre
May 1, 2021·Nature Communications·Bridget B McGivernKelly C Wrighton
Apr 18, 2021·International Journal of Biological Macromolecules·Yale Luck NunesJosé C S Dos Santos
Jun 19, 2021·Chemical Society Reviews·Dong YiUwe T Bornscheuer
Oct 12, 2021·Annual Review of Nutrition·Lucas J OsbornJ Mark Brown

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