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Volumn 19, Issue 11, 2009, Pages 1348-1354

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

Author keywords

2 hydroxygenistein; Antioxidant activity; Antiproliferation activity; Bioconversion; Genistein; MCF 7 cells

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2' HYDROXYGENISTEIN; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); GENISTEIN; ISOFLAVONOID; UNCLASSIFIED DRUG; 2' HYDROXY GENISTEIN; 2'-HYDROXY-GENISTEIN; 2,2' AZINO DI (3 ETHYLBENZOTHIAZOLINE) 6 SULFONIC ACID; 2,2'-AZINO-DI-(3-ETHYLBENZOTHIAZOLINE)-6-SULFONIC ACID; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTINEOPLASTIC AGENT; ANTIOXIDANT; BENZOTHIAZOLE DERIVATIVE; BIPHENYL DERIVATIVE; CYTOCHROME P 450 CYP81E1 (GLYCYRRHIZA ECHINATA); CYTOCHROME P-450 CYP81E1 (GLYCYRRHIZA ECHINATA); CYTOCHROME P450; DRUG DERIVATIVE; PICRIC ACID; SULFONIC ACID DERIVATIVE;

EID: 71549151334     PISSN: 10177825     EISSN: 17388872     Source Type: Journal    
DOI: 10.4014/jmb.0903.0114     Document Type: Article
Times cited : (21)

References (37)
  • 1
    • 0032500379 scopus 로고    scopus 로고
    • CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2′-hydroxylase
    • Akashi, T., T. Aoki, and S. Ayabe. 1998. CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2′-hydroxylase. Biochem. Biophys. Res. Commun. 251: 67-70.
    • (1998) Biochem. Biophys. Res. Commun. , vol.251 , pp. 67-70
    • Akashi, T.1    Aoki, T.2    Ayabe, S.3
  • 3
    • 0032529383 scopus 로고    scopus 로고
    • Antioxidant activities of isoflavones and their biological metabolites in a liposomal system
    • Arora, A., M. G. Nair, and G. M. Strasburg. 1998. Antioxidant activities of isoflavones and their biological metabolites in a liposomal system. Arch. Biochem. Biophys. 356: 133-141.
    • (1998) Arch. Biochem. Biophys. , vol.356 , pp. 133-141
    • Arora, A.1    Nair, M.G.2    Strasburg, G.M.3
  • 4
    • 0034846868 scopus 로고    scopus 로고
    • Antioxidant and antiradical activities of flavonoids
    • Burda, S. and W. Oleszek. 2001. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 49: 2774-2779.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 2774-2779
    • Burda, S.1    Oleszek, W.2
  • 5
    • 0028856746 scopus 로고
    • Biological effects of isoflavones in young women: Importance of the chemical composition of soyabean products
    • Cassidy, A., S. Bingham, and K. Setchell. 1995. Biological effects of isoflavones in young women: Importance of the chemical composition of soyabean products. Br. J. Nutr. 74: 587-601.
    • (1995) Br. J. Nutr. , vol.74 , pp. 587-601
    • Cassidy, A.1    Bingham, S.2    Setchell, K.3
  • 6
    • 37449004638 scopus 로고    scopus 로고
    • Correlation of antioxidant activity and major isoflavonoid contents of the phytoestrogenrich Pueraria mirifica and Pueraria lobata tubers
    • Cherdshewasart, W. and W. Sutjit. 2008. Correlation of antioxidant activity and major isoflavonoid contents of the phytoestrogenrich Pueraria mirifica and Pueraria lobata tubers. Phytomedicine 15: 38-43.
    • (2008) Phytomedicine , vol.15 , pp. 38-43
    • Cherdshewasart, W.1    Sutjit, W.2
  • 7
    • 34447510035 scopus 로고    scopus 로고
    • Commonly used Saccharomyces cerevisiae strains (e.g., BY4741, W303) are growth sensitive on synthetic complete medium due to poor leucine uptake
    • Engelberg, R. C. D. 2007. Commonly used Saccharomyces cerevisiae strains (e.g., BY4741, W303) are growth sensitive on synthetic complete medium due to poor leucine uptake. FEMS Microbiol. Lett. 273: 239-243.
    • (2007) FEMS Microbiol. Lett. , vol.273 , pp. 239-243
    • Engelberg, R.C.D.1
  • 8
    • 0032437643 scopus 로고    scopus 로고
    • Dietary genistein: Perinatal mammary cancer prevention, bioavailability and toxicity testing in the rat
    • Fritz, W. A., L. Coward, J. Wang, and C. A. Lamartiniere. 1998. Dietary genistein: Perinatal mammary cancer prevention, bioavailability and toxicity testing in the rat. Carcinogenesis 19: 2151-2158.
    • (1998) Carcinogenesis , vol.19 , pp. 2151-2158
    • Fritz, W.A.1    Coward, L.2    Wang, J.3    Lamartiniere, C.A.4
  • 9
    • 0028064562 scopus 로고
    • Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2′-dihydroxy- 4′-methoxyisoflavanol dehydratase
    • Guo, L., R. A. Dixon, and N. L. Paiva. 1994. Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2′-dihydroxy- 4′-methoxyisoflavanol dehydratase. J. Biol. Chem. 269: 22372-22378.
    • (1994) J. Biol. Chem. , vol.269 , pp. 22372-22378
    • Guo, L.1    Dixon, R.A.2    Paiva, N.L.3
  • 10
    • 0027988007 scopus 로고
    • The 'pterocarpan synthase' of alfalfa: Association and co-induction of vestitone reductase and 7,2′-dihydroxy-4′-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis
    • Guo, L., R. A. Dixon, and N. L. Paiva. 1994. The 'pterocarpan synthase' of alfalfa: Association and co-induction of vestitone reductase and 7,2′-dihydroxy-4′-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis. FEBS Lett. 356: 221-225.
    • (1994) FEBS Lett. , vol.356 , pp. 221-225
    • Guo, L.1    Dixon, R.A.2    Paiva, N.L.3
  • 11
    • 0034736046 scopus 로고    scopus 로고
    • Advances in flavonoid research since 1992
    • Harborne, J. B. and C. A. Williams. 2000. Advances in flavonoid research since 1992. Phytochemistry 55: 481-504.
    • (2000) Phytochemistry , vol.55 , pp. 481-504
    • Harborne, J.B.1    Williams, C.A.2
  • 12
    • 0034182708 scopus 로고    scopus 로고
    • 1,1-Diphenyl-2-picrylhydrazyl radical-scavenging compounds from soybean miso and antiproliferative activity of isoflavones from soybean miso toward the cancer cell lines
    • Hirota, A., S. Taki, S. Kawaii, M. Yano, and N. Abe. 2000. 1,1-Diphenyl-2-picrylhydrazyl radical-scavenging compounds from soybean miso and antiproliferative activity of isoflavones from soybean miso toward the cancer cell lines. Biosci. Biotechnol. Biochem. 64: 1038-1040.
    • (2000) Biosci. Biotechnol. Biochem. , vol.64 , pp. 1038-1040
    • Hirota, A.1    Taki, S.2    Kawaii, S.3    Yano, M.4    Abe, N.5
  • 13
    • 0942297864 scopus 로고    scopus 로고
    • Optimization of an in vivo plant P450 monooxygenase system in Saccharomyces cerevisiae
    • Jiang, H. and J. A. Morgan. 2004. Optimization of an in vivo plant P450 monooxygenase system in Saccharomyces cerevisiae. Biotechnol. Bioeng. 85: 130-137.
    • (2004) Biotechnol. Bioeng. , vol.85 , pp. 130-137
    • Jiang, H.1    Morgan, J.A.2
  • 14
    • 33750428557 scopus 로고    scopus 로고
    • Functional components in soybean cake and their effects on antioxidant activity
    • Kao, T. H. and B. H. Chen. 2006. Functional components in soybean cake and their effects on antioxidant activity. J. Agric. Food Chem. 54: 7544-7555.
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 7544-7555
    • Kao, T.H.1    Chen, B.H.2
  • 15
    • 0031741785 scopus 로고    scopus 로고
    • Mechanisms of action of the soy isoflavone genistein: Emerging role for its effects via transforming growth factor beta signaling pathways
    • Kim, H., T. G. Peterson, and S. Barnes. 1998. Mechanisms of action of the soy isoflavone genistein: Emerging role for its effects via transforming growth factor beta signaling pathways. Am. J. Clin. Nutr. 68: 1418S-1425S.
    • (1998) Am. J. Clin. Nutr. , vol.68
    • Kim, H.1    Peterson, T.G.2    Barnes, S.3
  • 16
    • 38649099376 scopus 로고    scopus 로고
    • Antioxidant and antigenotoxic activities of Korean fermented soybean
    • Kim, N. Y., E. J. Song, D. Y. Kwon, H. P. Kim, and M. Y. Heo. 2008. Antioxidant and antigenotoxic activities of Korean fermented soybean. Food Chem. Toxicol. 46: 1184-1189.
    • (2008) Food Chem. Toxicol. , vol.46 , pp. 1184-1189
    • Kim, N.Y.1    Song, E.J.2    Kwon, D.Y.3    Kim, H.P.4    Heo, M.Y.5
  • 17
    • 0034841150 scopus 로고    scopus 로고
    • Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo
    • Kulling, S. E., D. M. Honig, and M. Metzler. 2001. Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. J. Agric. Food Chem. 49: 3024-3033.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 3024-3033
    • Kulling, S.E.1    Honig, D.M.2    Metzler, M.3
  • 18
    • 0033789387 scopus 로고    scopus 로고
    • Oxidative in vitro metabolism of the soy phytoestrogens daidzein and genistein
    • Kulling, S. E., D. M. Honig, T. J. Simat, and M. Metzler. 2000. Oxidative in vitro metabolism of the soy phytoestrogens daidzein and genistein. J. Agric. Food Chem. 48: 4963-4972.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 4963-4972
    • Kulling, S.E.1    Honig, D.M.2    Simat, T.J.3    Metzler, M.4
  • 19
    • 28044449967 scopus 로고    scopus 로고
    • Identification of flavonoids using liquid chromatography with electrospray ionization and ion trap tandem mass spectrometry with an MS/MS library
    • Lee, J. S., D. H. Kim, K. H. Liu, T. K. Oh, and C. H. Lee. 2005. Identification of flavonoids using liquid chromatography with electrospray ionization and ion trap tandem mass spectrometry with an MS/MS library. Rapid Commun. Mass Spectrom. 19: 3539-3548.
    • (2005) Rapid Commun. Mass Spectrom. , vol.19 , pp. 3539-3548
    • Lee, J.S.1    Kim, D.H.2    Liu, K.H.3    Oh, T.K.4    Lee, C.H.5
  • 21
    • 0033587157 scopus 로고    scopus 로고
    • Induction of apoptosis in breast cancer cells MDA-MB-231 by genistein
    • DOI 10.1038/sj.onc.1202650
    • Li, Y., S. Upadhyay, M. Bhuiyan, and F. H. Sarkar. 1999. Induction of apoptosis in breast cancer cells MDA-MB-231 by genistein. Oncogene 18: 3166-3172. (Pubitemid 29261238)
    • (1999) Oncogene , vol.18 , Issue.20 , pp. 3166-3172
    • Li, Y.1    Upadhyay, S.2    Bhuiyan, M.3    Sarkar, F.H.4
  • 22
    • 0029805716 scopus 로고    scopus 로고
    • Genistein inhibits both estrogen and growth factor-stimulated proliferation of human breast cancer cells
    • Peterson, G. and S. Barnes. 1996. Genistein inhibits both estrogen and growth factor-stimulated proliferation of human breast cancer cells. Cell Growth Differ. 7: 1345-1351. (Pubitemid 26360683)
    • (1996) Cell Growth and Differentiation , vol.7 , Issue.10 , pp. 1345-1351
    • Peterson, G.1    Barnes, S.2
  • 23
    • 0029776005 scopus 로고    scopus 로고
    • Yeast expression of animal and plant P450s in optimized redox environments
    • Pompon, D., B. Louerat, A. Bronine, and P. Urban. 1996. Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol. 272: 51-64. (Pubitemid 26299867)
    • (1996) Methods in Enzymology , vol.272 , pp. 51-64
    • Pompon, D.1    Louerat, B.2    Bronine, A.3    Urban, P.4
  • 24
    • 20444488867 scopus 로고    scopus 로고
    • Partial reconstruction of flavonoid and isoflavonoid biosynthesis in yeast using soybean type I and type II chalcone isomerases
    • Ralston, L., S. Subramanian, M. Matsuno, and O. Yu. 2005. Partial reconstruction of flavonoid and isoflavonoid biosynthesis in yeast using soybean type I and type II chalcone isomerases. Plant Physiol. 137: 1375-1388.
    • (2005) Plant Physiol. , vol.137 , pp. 1375-1388
    • Ralston, L.1    Subramanian, S.2    Matsuno, M.3    Yu, O.4
  • 27
    • 0036945663 scopus 로고    scopus 로고
    • Mechanisms of cancer chemoprevention by soy isoflavone genistein
    • Sarkar, F. H. and Y. Li. 2002. Mechanisms of cancer chemoprevention by soy isoflavone genistein. Cancer Metastasis Rev. 21: 265-280.
    • (2002) Cancer Metastasis Rev. , vol.21 , pp. 265-280
    • Sarkar, F.H.1    Li, Y.2
  • 28
    • 0242496947 scopus 로고    scopus 로고
    • Soy isoflavones and cancer prevention
    • Sarkar, F. H. and Y. Li. 2003. Soy isoflavones and cancer prevention. Cancer Invest. 21: 744-757.
    • (2003) Cancer Invest. , vol.21 , pp. 744-757
    • Sarkar, F.H.1    Li, Y.2
  • 29
    • 0032212387 scopus 로고    scopus 로고
    • Genistein exerts multiple suppressive effects on human breast carcinoma cells
    • Shao, Z. M., J. Wu, Z. Z. Shen, and S. H. Barsky. 1998. Genistein exerts multiple suppressive effects on human breast carcinoma cells. Cancer Res. 58: 4851-4857.
    • (1998) Cancer Res. , vol.58 , pp. 4851-4857
    • Shao, Z.M.1    Wu, J.2    Shen, Z.Z.3    Barsky, S.H.4
  • 30
    • 34548329748 scopus 로고    scopus 로고
    • Genistein-induced apoptosis of human breast cancer MCF-7 cells involves calpain-caspase and apoptosis signaling kinase 1-p38 mitogen-activated protein kinase activation cascades
    • Shim, H. Y., J. H. Park, H. D. Paik, S. Y. Nah, D. S. Kim, and Y. S. Han. 2007. Genistein-induced apoptosis of human breast cancer MCF-7 cells involves calpain-caspase and apoptosis signaling kinase 1-p38 mitogen-activated protein kinase activation cascades. Anticancer Drugs 18: 649-657.
    • (2007) Anticancer Drugs , vol.18 , pp. 649-657
    • Shim, H.Y.1    Park, J.H.2    Paik, H.D.3    Nah, S.Y.4    Kim, D.S.5    Han, Y.S.6
  • 31
    • 0030798636 scopus 로고    scopus 로고
    • Pitfalls in a method for assessment of total antioxidant capacity
    • Strube, M., G. R. Haenen, H. Van Den Berg, and A. Bast. 1997. Pitfalls in a method for assessment of total antioxidant capacity. Free Radic. Res. 26: 515-521.
    • (1997) Free Radic. Res. , vol.26 , pp. 515-521
    • Strube, M.1    Haenen, G.R.2    Van Den Berg, H.3    Bast, A.4
  • 32
    • 0037478969 scopus 로고    scopus 로고
    • Thermal stability of genistein and daidzein and its effect on their antioxidant activity
    • Ungar, Y., O. F. Osundahunsi, and E. Shimoni. 2003. Thermal stability of genistein and daidzein and its effect on their antioxidant activity. J. Agric. Food Chem. 51: 4394-4399.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 4394-4399
    • Ungar, Y.1    Osundahunsi, O.F.2    Shimoni, E.3
  • 33
    • 0030852872 scopus 로고    scopus 로고
    • Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5
    • Urban, P., C. Mignotte, M. Kazmaier, F. Delorme, and D. Pompon. 1997. Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5. J. Biol. Chem. 272: 19176-19186.
    • (1997) J. Biol. Chem. , vol.272 , pp. 19176-19186
    • Urban, P.1    Mignotte, C.2    Kazmaier, M.3    Delorme, F.4    Pompon, D.5
  • 34
    • 0028944947 scopus 로고
    • Antioxidant and antipromotional effects of the soybean isoflavone genistein
    • Wei, H., R. Bowen, Q. Cai, S. Barnes, and Y. Wang. 1995. Antioxidant and antipromotional effects of the soybean isoflavone genistein. Proc. Soc. Exp. Biol. Med. 208: 124-130.
    • (1995) Proc. Soc. Exp. Biol. Med. , vol.208 , pp. 124-130
    • Wei, H.1    Bowen, R.2    Cai, Q.3    Barnes, S.4    Wang, Y.5
  • 35
    • 2442543529 scopus 로고    scopus 로고
    • LC/ UV/ESI-MS analysis of isoflavones in edamame and tofu soybeans
    • Wu, Q., M. Wang, W. J. Sciarappa, and J. E. Simon. 2004. LC/ UV/ESI-MS analysis of isoflavones in edamame and tofu soybeans. J. Agric. Food Chem. 52: 2763-2769.
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 2763-2769
    • Wu, Q.1    Wang, M.2    Sciarappa, W.J.3    Simon, J.E.4
  • 37
    • 0025189757 scopus 로고
    • Induction of mammalian topoisomerase II dependent DNA cleavage by nonintercalative flavonoids, genistein and orobol
    • Yamashita, Y., S. Kawada, and H. Nakano. 1990. Induction of mammalian topoisomerase II dependent DNA cleavage by nonintercalative flavonoids, genistein and orobol. Biochem. Pharmacol. 39: 737-744.
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 737-744
    • Yamashita, Y.1    Kawada, S.2    Nakano, H.3


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