Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 21, Issue 7, Pages 2001-2006Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2013.01.026
Keywords
Xanthohumol; Biotransformation; Antiproliferative activity; Human carcinoma; Antioxidant activity
Funding
- European Union within the European Regional Development Found [POIG 01.03.01-00-158/09]
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Xanthohumol (1) and xanthohumol D (2) were isolated from spent hops. Isoxanthohumol (3) was obtained from xanthohumol by isomerisation in alkaline solution. Six metabolites were obtained as a result of transformation of xanthohumol (1) by selected fungal cultures. Their structures were established on the basis of their spectral data. One of them: 2 ''-(2'''-hydroxyisopropyl)-dihydrofurano-[4 '',5 '':3',4']-4',2-dihydroxy-6'-methoxy-alpha,beta-dihydrochalcone (6) has not been previously reported in the literature. The antioxidant properties of hops flavonoids and xanthohumol derivatives were investigated using the 2,2'-diplienyl-1-picrylhydrazyl (DPPH) radical scavenging method. The effects of these compounds on proliferation of MCF-7, PC-3 and HT-29 human cancer cell lines were determined by the SRB assay. With the exception of one metabolite, all tested compounds showed antiproliferative activity against the tested human cancer lines. alpha,beta-Dihydroxanthohumol (4), obtained through the biotransformation of xanthohumol, showed higher antiproliferative activity against MCF-7 human breast carcinoma cell line than cisplatin, a widely used anticancer therapeutic agent, and a comparably high activity against PC-3 human prostate cancer cell line. (C) 2013 Elsevier Ltd. All rights reserved.
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