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. Epub 2013 Feb 15.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / metabolism
  • Antioxidants / pharmacology*
  • Biotransformation*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Flavonoids / chemistry
  • Flavonoids / metabolism
  • Flavonoids / pharmacology*
  • Glycosides / chemistry
  • Glycosides / metabolism
  • Glycosides / pharmacology*
  • Glycosylation
  • HT29 Cells
  • Humans
  • Molecular Structure
  • Propiophenones / chemistry
  • Propiophenones / metabolism
  • Propiophenones / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Flavonoids
  • Glycosides
  • Propiophenones
  • xanthohumol