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J. Microbiol. Biotechnol. 2009; 19(11): 1348-1354

Published online November 28, 2009 https://doi.org/10.4014/jmb.0903.0114

Copyright © The Korean Society for Microbiology and Biotechnology.

2'-Hydroxylation of Genistein Enhanced Antioxidant and Antiproliferative Activities in MCF-7 Human Breast Cancer Cells

Jung Nam Choi , Dockyu Kim , Hyung Kyoon Choi , Kyung Mi Yoo , Jiyoung Kim and Choong Hwan Lee *

1Department of Bioscience and Biotechnology and Bio/Molecular Informatics Center, Konkuk University, Seoul 143-701, Korea, 2Polar BioCenter, Korea Polar Research Institute, KORDI, Incheon 406-840, Korea, 3College of Pharmacy, Chung-Ang University, Seoul 156-756, Korea

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.

Keywords: Genistein, 2, bioconversion, antioxidant activity, antiproliferation activity, MCF-7 cells