Regioselective ortho-Hydroxylations of Flavonoids by Yeast.
Natural flavonoids, such as naringenin, hesperetin, chrysin, apigenin, luteolin, quercetin, epicatechin, and biochanin A, were subjected to microbiological transformations by Rhodotorula glutinis. Yeast was able to regioselectively C-8 hydroxylate hesperetin, luteolin, and chrysin. Naringenin was transformed to 8- and 6-hydroxyderivatives. Quercetin, epicatechin, and biochanin A did not undergo biotransformation. A metabolic pathway for the degradation of chrysin has been elucidated. The metabolism of chrysin proceeds via an initial C-8 hydroxylation to norwogonin, followed by A-ring cleavage to 4-hydroxy-6-phenyl-2H-pyran-2-one.
Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.
Sandra
S
Sordon
Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.
Anna
A
Madej
Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.
Jarosław
J
Popłoński
Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.
Agnieszka
A
Bartmańska
Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.
Tomasz
T
Tronina
Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.
Ewa
E
Brzezowska
Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences , Chełmońskiego 37/41, 51-630 Wrocław, Poland.
Piotr
P
Juszczyk
Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.
Ewa
E
Huszcza
D001711:Biotransformation; D005419:Flavonoids / Q000737:chemistry* / Q000378:metabolism*; D006900:Hydroxylation; D012248:Rhodotorula / Q000378:metabolism*; D013237:Stereoisomerism
D005419:Flavonoids
Rhodotorula glutinis; biotransformation; flavonoids; hydroxylation; regioselectivity; yeast