2'-hydroxylation of genistein enhanced antioxidant and antiproliferative activities in mcf-7 human breast cancer cells

J Microbiol Biotechnol. 2009 Nov;19(11):1348-54. doi: 10.4014/jmb.0903.00114.

Abstract

Bioconversion of the isoflavonoid genistein to 2'- hydroxygenistein (2'-HG) was performed using isoflavone 2'-hydroxylase (CYP81E1) heterologously expressed in yeast. A monohydroxylated product was analyzed by liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) and NMR spectrometry and was identified as 2'-HG. An initial bioconversion rate of 6% was increased up to 14% under optimized conditions. After recovery, the biological activity of 2'-HG was evaluated. Bioconverted 2'-HG showed higher antioxidant activity against 1,1- diphenyl-2-picryl hydrazine (DPPH) and 2,2'-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radicals than did genistein. Furthermore, 2'-HG exhibited greater antiproliferative effects in MCF-7 human breast cancer cells than did genistein. These results suggest that 2'- hydroxylation of genistein enhanced its antioxidant activity and cell cytotoxicity in MCF-7 human breast cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anticarcinogenic Agents / administration & dosage
  • Anticarcinogenic Agents / chemistry
  • Antioxidants / administration & dosage*
  • Antioxidants / chemical synthesis
  • Benzothiazoles / chemistry
  • Biphenyl Compounds / chemistry
  • Breast Neoplasms / drug therapy*
  • Breast Neoplasms / pathology
  • Breast Neoplasms / physiopathology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Cell Survival / drug effects
  • Chromatography, Liquid
  • Cytochrome P-450 Enzyme System / chemistry*
  • Dose-Response Relationship, Drug
  • Female
  • Genistein / administration & dosage
  • Genistein / analogs & derivatives*
  • Genistein / chemical synthesis
  • Genistein / chemistry*
  • Genistein / pharmacology
  • Humans
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Picrates / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfonic Acids / chemistry

Substances

  • 2'-hydroxy-genistein
  • Anticarcinogenic Agents
  • Antioxidants
  • Benzothiazoles
  • Biphenyl Compounds
  • Picrates
  • Sulfonic Acids
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • Cytochrome P-450 Enzyme System
  • 1,1-diphenyl-2-picrylhydrazyl
  • Genistein
  • cytochrome P-450 CYP81E1 (Glycyrrhiza echinata)