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酵母对黄酮类化合物的区域选择性邻位羟基化反应

Regioselective ortho-Hydroxylations of Flavonoids by Yeast.

作者信息

Sordon Sandra, Madej Anna, Popłoński Jarosław, Bartmańska Agnieszka, Tronina Tomasz, Brzezowska Ewa, Juszczyk Piotr, Huszcza Ewa

机构信息

Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wroclaw, Poland.

Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences , Chełmońskiego 37/41, 51-630 Wrocław, Poland.

出版信息

J Agric Food Chem. 2016 Jul 13;64(27):5525-30. doi: 10.1021/acs.jafc.6b02210. Epub 2016 Jul 5.

DOI:10.1021/acs.jafc.6b02210
PMID:27324975
Abstract

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.

摘要

天然黄酮类化合物,如柚皮素、橙皮素、白杨素、芹菜素、木犀草素、槲皮素、表儿茶素和染料木黄酮,经粘红酵母进行微生物转化。该酵母能够区域选择性地对橙皮素、木犀草素和白杨素进行C-8羟基化。柚皮素被转化为8-和6-羟基衍生物。槲皮素、表儿茶素和染料木黄酮未发生生物转化。已阐明了白杨素的降解代谢途径。白杨素的代谢首先通过C-8羟基化生成去甲黄酮,然后A环裂解生成4-羟基-6-苯基-2H-吡喃-2-酮。

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