2'-hydroxylation of genistein enhanced antioxidant and antiproliferative activities in mcf-7 human breast cancer cells.
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.
Choi
Jung Nam
JN
Department of Bioscience and Biotechnology and Bio/Molecular Informatics Center, Konkuk University, Seoul 143-701, Korea.
Kim
Dockyu
D
Choi
Hyung Kyoon
HK
Yoo
Kyung Mi
KM
Kim
Jiyoung
J
Lee
Choong Hwan
CH
D016588:Anticarcinogenic Agents / Q000008:administration & dosage / Q000737:chemistry; D000975:Antioxidants / Q000008:administration & dosage* / Q000138:chemical synthesis; D052160:Benzothiazoles / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D001943:Breast Neoplasms / Q000188:drug therapy* / Q000473:pathology / Q000503:physiopathology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D002470:Cell Survival / Q000187:drug effects; D002853:Chromatography, Liquid; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D005260:Female; D019833:Genistein / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D010851:Picrates / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013451:Sulfonic Acids / Q000737:chemistry
C482259:2'-hydroxy-genistein; D016588:Anticarcinogenic Agents; D000975:Antioxidants; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D010851:Picrates; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D003577:Cytochrome P-450 Enzyme System; C004931:1,1-diphenyl-2-picrylhydrazyl; D019833:Genistein; C115412:cytochrome P-450 CYP81E1 (Glycyrrhiza echinata)