期刊
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 23, 期 7, 页码 1957-1960出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2013.02.031
关键词
Xanthohumol; Biotransformation; Glycosylation; Antiproliferative activity; Antioxidant activity; Spent hops
资金
- European Union within the European Regional Development Found [POIG.01.03.01-00-158/09]
The biotransformation of xanthohumol (1), a prenylated chalcone isolated from hops by selected fungi, was investigated. Microbial regioselective glycosylation at the C-4' position led to xanthohumol 4'-O-beta-D-glucopyranoside (2) and xanthohumol 4'-O-beta-D-(4 '''-O-methyl)-glucopyranoside (3). The subsequent cyclization of 2 resulted in isoxanthohumol 7-O-beta-glucopyranoside (4). The structures of the products were identified based on spectroscopic methods. The biological activity of isolated metabolites has been evaluated. Compared to xanthohumol (1), metabolite 2 is a better 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenger, while 2 and 3 have stronger antiproliferative activity against the human HT-29 colon cancer cell line. (C) 2013 Elsevier Ltd. All rights reserved.
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