烟色红曲霉 KCh J2 对雌激素的级联生物转化

Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2.

机构信息

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

出版信息

Sci Rep. 2019 Jul 24;9(1):10734. doi: 10.1038/s41598-019-47225-1.

DOI:10.1038/s41598-019-47225-1

PMID:31341201

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6656742/

Abstract

Estrone, estradiol, ethynylestradiol and estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transformed to D-ring lactone. Ethynylestradiol was coupled with methylglucoside and 6β-hydroxyderivative was obtained. Estrone 3-methyl ether was not transformed indicating that a free hydroxyl group at C-3 is necessary for glycosylation. Baeyer-Villiger oxidation combined with hydroxylation and glycosylation was observed. All glycosides obtained in this study are 3-O-β-methylglucosides.

摘要

雌酮、雌二醇、炔雌醇和雌酮 3-甲醚在玫烟色棒束孢（Isaria fumosorosea KCh J2）的液体培养中经历了生物转化过程。雌酮转化为七种代谢物，其中四种为糖基化产物。雌二醇在 C-3 位选择性糖基化，然后转化为 D-环内酯。炔雌醇与甲基葡萄糖苷偶联，得到 6β-羟基衍生物。雌酮 3-甲醚未发生转化，表明 C-3 位的游离羟基是糖基化的必要条件。观察到 Baeyer-Villiger 氧化与羟化和糖基化的结合。本研究中获得的所有糖苷均为 3-O-β-甲基葡萄糖苷。