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
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Research Support, Non-U.S. Gov't
MeSH terms
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Anticarcinogenic Agents / administration & dosage
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Anticarcinogenic Agents / chemistry
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Antioxidants / administration & dosage*
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Antioxidants / chemical synthesis
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Benzothiazoles / chemistry
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Biphenyl Compounds / chemistry
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Breast Neoplasms / drug therapy*
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Breast Neoplasms / pathology
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Breast Neoplasms / physiopathology
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Cell Line, Tumor
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Cell Proliferation / drug effects*
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Cell Survival / drug effects
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Chromatography, Liquid
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Cytochrome P-450 Enzyme System / chemistry*
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Dose-Response Relationship, Drug
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Female
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Genistein / administration & dosage
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Genistein / analogs & derivatives*
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Genistein / chemical synthesis
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Genistein / chemistry*
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Genistein / pharmacology
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Humans
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Hydroxylation
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Magnetic Resonance Spectroscopy
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Picrates / chemistry
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Spectrometry, Mass, Electrospray Ionization
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Sulfonic Acids / chemistry
Substances
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2'-hydroxy-genistein
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Anticarcinogenic Agents
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Antioxidants
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Benzothiazoles
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Biphenyl Compounds
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Picrates
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Sulfonic Acids
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2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
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Cytochrome P-450 Enzyme System
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1,1-diphenyl-2-picrylhydrazyl
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Genistein
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cytochrome P-450 CYP81E1 (Glycyrrhiza echinata)