Novel enzymatic route to the synthesis of C-8 hydroxyflavonoids including flavonols and isoflavones.

Autor: Dulak K; Department of Food Chemistry and Biocatalysis, Wroclaw University of Environmental and Life Sciences, Wroclaw, Poland., Sordon S; Department of Food Chemistry and Biocatalysis, Wroclaw University of Environmental and Life Sciences, Wroclaw, Poland., Matera A; Department of Food Chemistry and Biocatalysis, Wroclaw University of Environmental and Life Sciences, Wroclaw, Poland., Wilczak A; Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland., Huszcza E; Department of Food Chemistry and Biocatalysis, Wroclaw University of Environmental and Life Sciences, Wroclaw, Poland., Popłoński J; Department of Food Chemistry and Biocatalysis, Wroclaw University of Environmental and Life Sciences, Wroclaw, Poland. jaroslaw.poplonski@upwr.edu.pl.
Jazyk: angličtina
Zdroj: Scientific reports [Sci Rep] 2024 Aug 06; Vol. 14 (1), pp. 18217. Date of Electronic Publication: 2024 Aug 06.
DOI: 10.1038/s41598-024-68513-5
Abstrakt: Flavin-dependent monooxygenases (FMOs) are a valuable group of biocatalysts that can regioselectively introduce a hydroxy group for the targeted modification of biologically active compounds. Here, we present the fdeE, the FMO from Herbaspirillum seropedicae SmR1 that is a part of the naringenin degradation pathway and is active towards a wide range of flavonoids-flavanones, flavones, isoflavones, and flavonols. Bioinformatics and biochemical analysis revealed a high similarity between the analyzed enzyme and other F8H FMOs what might indicate convergent evolutionary mechanism of flavonoid degradation pathway emergence by microorganism. A simple approach with the manipulation of the reaction environment allowed the stable formation of hydroxylation products, which showed very high reactivity in both in vivo and in vitro assays. This approach resulted in an 8-hydroxyquercetin-gossypetin titer of 0.16 g/L and additionally it is a first report of production of this compound.
(© 2024. The Author(s).)
Databáze: MEDLINE
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