Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro.

Abstract

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-α,β-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'-diphenyl-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. α,β-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.

• Authors: Tomasz Tronina, Agnieszka Bartmańska, Beata Filip-Psurska, Joanna Wietrzyk, Jarosław Popłoński, Ewa Huszcza
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 21 Issue 7 Pg. 2001-6 (Apr 01 2013) ISSN: 1464-3391 [Electronic] England
• PMID: 23434138 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2013 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents
• Antioxidants
• Flavonoids
• Propiophenones
• xanthohumol

Topics

• Antineoplastic Agents (chemistry, isolation & purification, metabolism, pharmacology)
• Antioxidants (chemistry, isolation & purification, metabolism, pharmacology)
• Biotransformation
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Flavonoids (chemistry, isolation & purification, metabolism, pharmacology)
• Fungi (metabolism)
• Humans
• Humulus (chemistry)
• Neoplasms (drug therapy)
• Propiophenones (chemistry, isolation & purification, metabolism, pharmacology)