1. Academic Validation
  2. Antioxidant and antiproliferative activity of glycosides obtained by biotransformation of xanthohumol

Antioxidant and antiproliferative activity of glycosides obtained by biotransformation of xanthohumol

  • Bioorg Med Chem Lett. 2013 Apr 1;23(7):1957-60. doi: 10.1016/j.bmcl.2013.02.031.
Tomasz Tronina 1 Agnieszka Bartmańska Magdalena Milczarek Joanna Wietrzyk Jarosław Popłoński Edward Rój Ewa Huszcza
Affiliations

Affiliation

  • 1 Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. tomasz.tronina@up.wroc.pl
Abstract

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-β-d-glucopyranoside (2) and xanthohumol 4'-O-β-d-(4'''-O-methyl)-glucopyranoside (3). The subsequent cyclization of 2 resulted in isoxanthohumol 7-O-β-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.

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