메뉴 건너뛰기




Volumn 126, Issue 1, 2010, Pages 9-20

Dietary flavonoids in cancer therapy and prevention: Substrates and inhibitors of cytochrome P450 CYP1 enzymes

Author keywords

Chemoprevention; CYP1 enzymes; Flavonoids; Inhibition; Metabolism

Indexed keywords

2' NITROFLAVONE; 5,7 DIMETHOXYFLAVONE; AMINOFLAVONE; APIGENIN; CANCER VACCINE; CHRYSIN; CYTOCHROME P450; CYTOCHROME P450 1; CYTOCHROME P450 1B1 VACCINE; CYTOTOXIC AGENT; DIOSMETIN; DIOSMIN; ETHOXYRESORUFIN; EUPATORIN; FLAVONOID; FLAVONOID GLYCOSIDE; LUTEOLIN; NARINGENIN; PICEATTANOL; PLANT MEDICINAL PRODUCT; QUERCETIN; SCUTELLAREIN; UNCLASSIFIED DRUG;

EID: 77949275110     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.pharmthera.2010.01.009     Document Type: Review
Times cited : (178)

References (94)
  • 2
    • 55749110433 scopus 로고    scopus 로고
    • Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1 mediated metabolism
    • Androutsopoulos V., Arroo R.R., Hall J.F., Surichan S., and Potter G.A. Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1 mediated metabolism. Breast Cancer Res 10 (2008) R39
    • (2008) Breast Cancer Res , vol.10
    • Androutsopoulos, V.1    Arroo, R.R.2    Hall, J.F.3    Surichan, S.4    Potter, G.A.5
  • 3
    • 57749091536 scopus 로고    scopus 로고
    • Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450
    • Androutsopoulos V., Arroo R.R., Wilsher N., and Potter G.A. Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450. Cancer Lett 274 (2009) 54-60
    • (2009) Cancer Lett , vol.274 , pp. 54-60
    • Androutsopoulos, V.1    Arroo, R.R.2    Wilsher, N.3    Potter, G.A.4
  • 4
    • 69949161198 scopus 로고    scopus 로고
    • The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells
    • Androutsopoulos V.P., Li N., and Arroo R.R. The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells. J Nat Prod 72 (2009) 1390-1394
    • (2009) J Nat Prod , vol.72 , pp. 1390-1394
    • Androutsopoulos, V.P.1    Li, N.2    Arroo, R.R.3
  • 5
    • 67649935021 scopus 로고    scopus 로고
    • Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 cells, due to CYP1 activation
    • Androutsopoulos V.P., Mahale S., Arroo R.R., and Potter G.A. Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 cells, due to CYP1 activation. Oncol Rep 21 (2009) 1525-1528
    • (2009) Oncol Rep , vol.21 , pp. 1525-1528
    • Androutsopoulos, V.P.1    Mahale, S.2    Arroo, R.R.3    Potter, G.A.4
  • 6
    • 70349213212 scopus 로고    scopus 로고
    • CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells
    • Androutsopoulos V.P., Ruparelia K., Arroo R.R., Tsatsakis A.M., and Spandidos D.A. CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells. Toxicology 264 (2009) 162-170
    • (2009) Toxicology , vol.264 , pp. 162-170
    • Androutsopoulos, V.P.1    Ruparelia, K.2    Arroo, R.R.3    Tsatsakis, A.M.4    Spandidos, D.A.5
  • 7
    • 67650074960 scopus 로고    scopus 로고
    • Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention
    • Androutsopoulos V.P., Tsatsakis A.M., and Spandidos D.A. Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention. BMC Cancer 9 (2009) 187
    • (2009) BMC Cancer , vol.9 , pp. 187
    • Androutsopoulos, V.P.1    Tsatsakis, A.M.2    Spandidos, D.A.3
  • 10
    • 33746690306 scopus 로고    scopus 로고
    • Metabolism of the soyabean isoflavone daidzein by CYP1A2 and the extra-hepatic CYPs 1A1 and 1B1 affects biological activity
    • Atherton K.M., Mutch E., and Ford D. Metabolism of the soyabean isoflavone daidzein by CYP1A2 and the extra-hepatic CYPs 1A1 and 1B1 affects biological activity. Biochem Pharmacol 72 (2006) 624-631
    • (2006) Biochem Pharmacol , vol.72 , pp. 624-631
    • Atherton, K.M.1    Mutch, E.2    Ford, D.3
  • 11
    • 0031057115 scopus 로고    scopus 로고
    • Inhibition of ultraviolet light skin carcinogenesis in SKH-1 mice by apigenin, a plant flavonoid
    • Birt D.F., Mitchell D., Gold B., Pour P., and Pinch H.C. Inhibition of ultraviolet light skin carcinogenesis in SKH-1 mice by apigenin, a plant flavonoid. Anticancer Res 17 (1997) 85-91
    • (1997) Anticancer Res , vol.17 , pp. 85-91
    • Birt, D.F.1    Mitchell, D.2    Gold, B.3    Pour, P.4    Pinch, H.C.5
  • 12
    • 0034807826 scopus 로고    scopus 로고
    • Dietary agents in cancer prevention: flavonoids and isoflavonoids
    • Birt D.F., Hendrich S., and Wang W. Dietary agents in cancer prevention: flavonoids and isoflavonoids. Pharmacol Ther 90 (2001) 157-177
    • (2001) Pharmacol Ther , vol.90 , pp. 157-177
    • Birt, D.F.1    Hendrich, S.2    Wang, W.3
  • 15
    • 0038683676 scopus 로고    scopus 로고
    • In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s
    • Breinholt V.M., Rasmussen S.E., Brøsen K., and Friedberg T.H. In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s. Pharmacol Toxicol 93 (2003) 14-22
    • (2003) Pharmacol Toxicol , vol.93 , pp. 14-22
    • Breinholt, V.M.1    Rasmussen, S.E.2    Brøsen, K.3    Friedberg, T.H.4
  • 16
    • 66149107982 scopus 로고    scopus 로고
    • In vitro induction of apoptosis and in vivo effects of a flavone nitroderivative in murine mammary adenocarcinoma cells
    • Cárdenas M.G., Zotta E., Marder M., and Roguin L.P. In vitro induction of apoptosis and in vivo effects of a flavone nitroderivative in murine mammary adenocarcinoma cells. Int J Cancer 125 (2009) 222-228
    • (2009) Int J Cancer , vol.125 , pp. 222-228
    • Cárdenas, M.G.1    Zotta, E.2    Marder, M.3    Roguin, L.P.4
  • 17
    • 0041561001 scopus 로고    scopus 로고
    • A potential protective mechanism of soya isoflavones against 7, 12-dimethylbenz[a]anthracene tumour initiation
    • Chan H.Y., and Leung L.K. A potential protective mechanism of soya isoflavones against 7, 12-dimethylbenz[a]anthracene tumour initiation. Br J Nutr 90 (2003) 457-465
    • (2003) Br J Nutr , vol.90 , pp. 457-465
    • Chan, H.Y.1    Leung, L.K.2
  • 18
    • 33646131391 scopus 로고    scopus 로고
    • Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1
    • Chang T.K.H., Chen J., and Yeung E.Y.H. Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1. Toxicol Appl Pharmacol 213 (2006) 18-26
    • (2006) Toxicol Appl Pharmacol , vol.213 , pp. 18-26
    • Chang, T.K.H.1    Chen, J.2    Yeung, E.Y.H.3
  • 19
    • 0041368576 scopus 로고    scopus 로고
    • The red clover (Trifolium pratense) isoflavone biochanin A modulates the biotransformation pathways of 7, 12-dimethylbenz[a]anthracene
    • Chan H.Y., Wang H., and Leung L.K. The red clover (Trifolium pratense) isoflavone biochanin A modulates the biotransformation pathways of 7, 12-dimethylbenz[a]anthracene. Br J Nutr 90 (2003) 87-92
    • (2003) Br J Nutr , vol.90 , pp. 87-92
    • Chan, H.Y.1    Wang, H.2    Leung, L.K.3
  • 20
    • 28844494466 scopus 로고    scopus 로고
    • Inhibition of human cytochrome CYP1 enzymes by flavonoids of St John's wort
    • Chaudhary A., and Willet K.L. Inhibition of human cytochrome CYP1 enzymes by flavonoids of St John's wort. Toxicology 217 (2006) 194-205
    • (2006) Toxicology , vol.217 , pp. 194-205
    • Chaudhary, A.1    Willet, K.L.2
  • 21
    • 52649173776 scopus 로고    scopus 로고
    • Daidzein modulates induction of hepatic CYP1A1, 1B1 and AhR by 7, 12-dimethylbenz[a]anthracene in mice
    • Choi E.J., and Kim T. Daidzein modulates induction of hepatic CYP1A1, 1B1 and AhR by 7, 12-dimethylbenz[a]anthracene in mice. Arch Pharm Res 31 (2008) 1115-1119
    • (2008) Arch Pharm Res , vol.31 , pp. 1115-1119
    • Choi, E.J.1    Kim, T.2
  • 22
    • 33645569435 scopus 로고    scopus 로고
    • Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous ipriflavone in rats
    • Chung H.J., Choi Y.H., Kim S.H., and Lee M.G. Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous ipriflavone in rats. J Pharm Pharmacol 58 (2006) 449-457
    • (2006) J Pharm Pharmacol , vol.58 , pp. 449-457
    • Chung, H.J.1    Choi, Y.H.2    Kim, S.H.3    Lee, M.G.4
  • 23
    • 0033564553 scopus 로고    scopus 로고
    • Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially
    • Ciolino H.P., Daschner P.J., and Yeh G.C. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem J 340 (1999) 715-722
    • (1999) Biochem J , vol.340 , pp. 715-722
    • Ciolino, H.P.1    Daschner, P.J.2    Yeh, G.C.3
  • 24
    • 0033014568 scopus 로고    scopus 로고
    • The flavonoid galangin in an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor
    • Ciolino H.P., and Yeh G.C. The flavonoid galangin in an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Br J Cancer 79 (1999) 1340-1346
    • (1999) Br J Cancer , vol.79 , pp. 1340-1346
    • Ciolino, H.P.1    Yeh, G.C.2
  • 25
    • 0031725843 scopus 로고    scopus 로고
    • Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity
    • Ciolino H.P., Wang T.T., and Yeh G.C. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res 56 (1998) 197-206
    • (1998) Cancer Res , vol.56 , pp. 197-206
    • Ciolino, H.P.1    Wang, T.T.2    Yeh, G.C.3
  • 26
    • 0031730172 scopus 로고    scopus 로고
    • Inhibition of human cytochrome P450 1A2 by flavones: a molecular modeling study
    • Dai R., Zhai S., Wei X., Pincus M.R., Vestal R.E., and Friedman F.K. Inhibition of human cytochrome P450 1A2 by flavones: a molecular modeling study. J Protein Chem 17 (1998) 643-650
    • (1998) J Protein Chem , vol.17 , pp. 643-650
    • Dai, R.1    Zhai, S.2    Wei, X.3    Pincus, M.R.4    Vestal, R.E.5    Friedman, F.K.6
  • 27
    • 0037633665 scopus 로고    scopus 로고
    • Effect of structural modification on the inhibitory selectivity of rutaecarpine derivatives on human CYP1A1, CYP1A2 and CYP1B1
    • Don M.J., Lewis D.F., Wang S.Y., Tsai M.W., and Ueng Y.F. Effect of structural modification on the inhibitory selectivity of rutaecarpine derivatives on human CYP1A1, CYP1A2 and CYP1B1. Bioorg Med Chem Lett 13 (2003) 2535-2538
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 2535-2538
    • Don, M.J.1    Lewis, D.F.2    Wang, S.Y.3    Tsai, M.W.4    Ueng, Y.F.5
  • 28
    • 0034599543 scopus 로고    scopus 로고
    • Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1
    • Doostdar H., Burke M.D., and Mayer R.T. Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology 144 (2000) 31-38
    • (2000) Toxicology , vol.144 , pp. 31-38
    • Doostdar, H.1    Burke, M.D.2    Mayer, R.T.3
  • 30
    • 0035150315 scopus 로고    scopus 로고
    • Plasma kinetics and urinary excretion of the flavanones naringenin and hesperitin in humans after ingestion of orange juice and grapefruit juice
    • Erlund I., Meririnne E., Alfthan G., and Aro A. Plasma kinetics and urinary excretion of the flavanones naringenin and hesperitin in humans after ingestion of orange juice and grapefruit juice. J Nutr 131 (2001) 235-241
    • (2001) J Nutr , vol.131 , pp. 235-241
    • Erlund, I.1    Meririnne, E.2    Alfthan, G.3    Aro, A.4
  • 31
    • 0027510377 scopus 로고
    • Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man
    • Fuhr U., Klittich K., and Staib A.H. Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. Br J Clin Pharm 35 (1993) 431-436
    • (1993) Br J Clin Pharm , vol.35 , pp. 431-436
    • Fuhr, U.1    Klittich, K.2    Staib, A.H.3
  • 32
    • 0033391399 scopus 로고    scopus 로고
    • Extensive metabolism of the flavonoid chrysin by human Caco-2 and Hep G2 cells
    • Galijatovic A., Otake Y., Walle U.K., and Walle T. Extensive metabolism of the flavonoid chrysin by human Caco-2 and Hep G2 cells. Xenobiotica 29 (1999) 1241-1256
    • (1999) Xenobiotica , vol.29 , pp. 1241-1256
    • Galijatovic, A.1    Otake, Y.2    Walle, U.K.3    Walle, T.4
  • 33
    • 1642539168 scopus 로고    scopus 로고
    • Metabolism of apigenin by rat liver phase I and phase II enzymes and by isolated perfused rat liver
    • Gradolatto A., Canivenc-Lavier M.C., Basly J.P., Siess M.H., and Teyssier C. Metabolism of apigenin by rat liver phase I and phase II enzymes and by isolated perfused rat liver. Drug Metab Dispos 32 (2004) 58-65
    • (2004) Drug Metab Dispos , vol.32 , pp. 58-65
    • Gradolatto, A.1    Canivenc-Lavier, M.C.2    Basly, J.P.3    Siess, M.H.4    Teyssier, C.5
  • 34
    • 20444496893 scopus 로고    scopus 로고
    • Unexpected association between induction of immunity to the universal tumor antigen CYP1B1 and response to next therapy
    • Gribben J.G., Ryan D.P., Boyajian R., Urban R.G., Hedley M.L., Beach K., et al. Unexpected association between induction of immunity to the universal tumor antigen CYP1B1 and response to next therapy. Clin Cancer Res 12 (2005) 4430-4436
    • (2005) Clin Cancer Res , vol.12 , pp. 4430-4436
    • Gribben, J.G.1    Ryan, D.P.2    Boyajian, R.3    Urban, R.G.4    Hedley, M.L.5    Beach, K.6
  • 35
    • 0036016102 scopus 로고    scopus 로고
    • Arginine to lysine 108 substitution in recombinant CYP1A2 abolishes methoxyresorufin metabolism in lymphoblastoid cells
    • Hadjokas N.E., Dai R., Friedman F.K., Spence M.J., Cusack B.J., Vestal R.E., et al. Arginine to lysine 108 substitution in recombinant CYP1A2 abolishes methoxyresorufin metabolism in lymphoblastoid cells. Br J Pharmacol 136 (2002) 347-352
    • (2002) Br J Pharmacol , vol.136 , pp. 347-352
    • Hadjokas, N.E.1    Dai, R.2    Friedman, F.K.3    Spence, M.J.4    Cusack, B.J.5    Vestal, R.E.6
  • 36
    • 0031835035 scopus 로고    scopus 로고
    • Inhibition of mouse and human CYP 1A- and 2E1-dependent substrate metabolism by the isoflavonoids genistein and equol
    • Helsby N.A., Chipman J.K., Gescher A., and Kerr D. Inhibition of mouse and human CYP 1A- and 2E1-dependent substrate metabolism by the isoflavonoids genistein and equol. Food Chem Toxicol 36 (1998) 375-382
    • (1998) Food Chem Toxicol , vol.36 , pp. 375-382
    • Helsby, N.A.1    Chipman, J.K.2    Gescher, A.3    Kerr, D.4
  • 37
    • 0031613667 scopus 로고    scopus 로고
    • Bioavailability and health effects of dietary flavonols in man
    • Hollman P.C.H., and Katan M.B. Bioavailability and health effects of dietary flavonols in man. Arch Toxicol Suppl 20 (1998) 237-248
    • (1998) Arch Toxicol Suppl , vol.20 , pp. 237-248
    • Hollman, P.C.H.1    Katan, M.B.2
  • 38
    • 0037636423 scopus 로고    scopus 로고
    • Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones
    • Hu M., Krausz K., Chen J., Ge X., Li J., Gelboin H.L., et al. Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones. Drug Metab Dispos 31 (2003) 924-931
    • (2003) Drug Metab Dispos , vol.31 , pp. 924-931
    • Hu, M.1    Krausz, K.2    Chen, J.3    Ge, X.4    Li, J.5    Gelboin, H.L.6
  • 39
    • 20444481352 scopus 로고    scopus 로고
    • Theoretical quantitative structure-activity relationships of flavone ligands interacting with cytochrome P450 1A1 and 1A2 isozymes
    • Iori F., da Fonseca R., Ramos M.J., and Menziani M.C. Theoretical quantitative structure-activity relationships of flavone ligands interacting with cytochrome P450 1A1 and 1A2 isozymes. Bioorg Med Chem 13 (2005) 4366-4374
    • (2005) Bioorg Med Chem , vol.13 , pp. 4366-4374
    • Iori, F.1    da Fonseca, R.2    Ramos, M.J.3    Menziani, M.C.4
  • 40
    • 33646719529 scopus 로고    scopus 로고
    • Preventive effects of quercetin against benzo[a]pyrene-induced DNA damages and pulmonary precancerous pathologic changes in mice
    • Jin N.Z., Zhu Y.P., Zhou J.W., Mao L., Zhao R.C., Fang T.H., et al. Preventive effects of quercetin against benzo[a]pyrene-induced DNA damages and pulmonary precancerous pathologic changes in mice. Basic Clin Pharmacol Toxicol 98 (2006) 593-598
    • (2006) Basic Clin Pharmacol Toxicol , vol.98 , pp. 593-598
    • Jin, N.Z.1    Zhu, Y.P.2    Zhou, J.W.3    Mao, L.4    Zhao, R.C.5    Fang, T.H.6
  • 41
    • 27744476241 scopus 로고    scopus 로고
    • Effects of hydroxyl group numbers on the B-ring of 5, 7-dihydroxyflavones on the differential inhibition of human CYP 1A and CYP1B1 enzymes
    • Kim H.J., Lee S.B., Park S.K., Kim H.M., Park Y.I., and Dong M.S. Effects of hydroxyl group numbers on the B-ring of 5, 7-dihydroxyflavones on the differential inhibition of human CYP 1A and CYP1B1 enzymes. Arch Pharm Res 28 (2005) 1114-1121
    • (2005) Arch Pharm Res , vol.28 , pp. 1114-1121
    • Kim, H.J.1    Lee, S.B.2    Park, S.K.3    Kim, H.M.4    Park, Y.I.5    Dong, M.S.6
  • 43
    • 0036155381 scopus 로고    scopus 로고
    • Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1
    • Lautraite S., Musonda A.C., Doehmer J., Edwards G.O., and Chipman J.K. Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1. Mutagenesis 17 (2002) 45-53
    • (2002) Mutagenesis , vol.17 , pp. 45-53
    • Lautraite, S.1    Musonda, A.C.2    Doehmer, J.3    Edwards, G.O.4    Chipman, J.K.5
  • 44
    • 34547809372 scopus 로고    scopus 로고
    • Developing a high-throughput system for the screening of cytochrome P450 1A1-inhibitory polyphenols
    • Leung H.Y., Wang Y., Chan H.Y., and Leung L.K. Developing a high-throughput system for the screening of cytochrome P450 1A1-inhibitory polyphenols. Toxicol in vitro 21 (2007) 996-1002
    • (2007) Toxicol in vitro , vol.21 , pp. 996-1002
    • Leung, H.Y.1    Wang, Y.2    Chan, H.Y.3    Leung, L.K.4
  • 45
    • 0038327885 scopus 로고    scopus 로고
    • Molecular modeling of human CYP1B1 substrate interactions and investigation of allelic variant effects on metabolism
    • Lewis D.F.V., Gillam E.M.J., Everett S.A., and Shimada T. Molecular modeling of human CYP1B1 substrate interactions and investigation of allelic variant effects on metabolism. Chem Biol Interact 145 (2003) 281-295
    • (2003) Chem Biol Interact , vol.145 , pp. 281-295
    • Lewis, D.F.V.1    Gillam, E.M.J.2    Everett, S.A.3    Shimada, T.4
  • 46
    • 3242808209 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships within a homologous series of 7-alkoxyresorufins exhibiting activity towards CYP1A and CYP2B enzymes: molecular modeling studies on key members of the resorufin series with CYP2C5-derived models of human CYP1A1, CYP1A2, CYP2B6 and CYP3A4
    • Lewis D.F., Lake B.G., and Dickins M. Quantitative structure-activity relationships within a homologous series of 7-alkoxyresorufins exhibiting activity towards CYP1A and CYP2B enzymes: molecular modeling studies on key members of the resorufin series with CYP2C5-derived models of human CYP1A1, CYP1A2, CYP2B6 and CYP3A4. Xenobiotica 34 (2004) 501-513
    • (2004) Xenobiotica , vol.34 , pp. 501-513
    • Lewis, D.F.1    Lake, B.G.2    Dickins, M.3
  • 47
    • 0032722410 scopus 로고    scopus 로고
    • Molecular modeling of CYP1 family enzymes CYP1A1, CYP1A2, CYP1A6 and CYP1B1 based on sequence homology with CYP102
    • Lewis D.F.V., Lake B.G., George S.G., Dickins M., Eddershaw P.J., Tarbit M.H., et al. Molecular modeling of CYP1 family enzymes CYP1A1, CYP1A2, CYP1A6 and CYP1B1 based on sequence homology with CYP102. Toxicology 139 (1999) 53-79
    • (1999) Toxicology , vol.139 , pp. 53-79
    • Lewis, D.F.V.1    Lake, B.G.2    George, S.G.3    Dickins, M.4    Eddershaw, P.J.5    Tarbit, M.H.6
  • 48
    • 36049033829 scopus 로고    scopus 로고
    • Comparative homology modeling of human cytochrome P4501A1 (CYP1A1) and confirmation of residues involved in 7-ethoxyresorufin O-deethylation by site-directed mutagenesis and enzyme kinetic analysis
    • Lewis B.C., Mackenzie P.I., and Miners J.O. Comparative homology modeling of human cytochrome P4501A1 (CYP1A1) and confirmation of residues involved in 7-ethoxyresorufin O-deethylation by site-directed mutagenesis and enzyme kinetic analysis. Arch Biochem Biophys 468 (2007) 58-69
    • (2007) Arch Biochem Biophys , vol.468 , pp. 58-69
    • Lewis, B.C.1    Mackenzie, P.I.2    Miners, J.O.3
  • 49
    • 0032930071 scopus 로고    scopus 로고
    • Soybean isoflavones reduce experimental metastasis in mice
    • Li D.H., Yee J.A., McGuire M.H., Murphy P.A., and Yan L. Soybean isoflavones reduce experimental metastasis in mice. J Nutr 129 (1999) 1075-1078
    • (1999) J Nutr , vol.129 , pp. 1075-1078
    • Li, D.H.1    Yee, J.A.2    McGuire, M.H.3    Murphy, P.A.4    Yan, L.5
  • 51
    • 1542328873 scopus 로고    scopus 로고
    • The effect of reciprocal active site mutations in human cytochromes P450 1A1 and 1A2 on alkoxyresorufin metabolism
    • Liu J., Ericksen S.S., Sivaneri M., Besspiata D., Fisher C.W., and Szklarz G.D. The effect of reciprocal active site mutations in human cytochromes P450 1A1 and 1A2 on alkoxyresorufin metabolism. Arch Biochem Biophys 424 (2004) 33-43
    • (2004) Arch Biochem Biophys , vol.424 , pp. 33-43
    • Liu, J.1    Ericksen, S.S.2    Sivaneri, M.3    Besspiata, D.4    Fisher, C.W.5    Szklarz, G.D.6
  • 52
    • 0037377894 scopus 로고    scopus 로고
    • Characterization of substrate binding to cytochrome P450 1A1 using molecular modeling and kinetic analyses: case of residue 382
    • Liu J., Ericksen S.S., Sivaneri M., Besspiata D., Fisher C.W., and Szklarz G.D. Characterization of substrate binding to cytochrome P450 1A1 using molecular modeling and kinetic analyses: case of residue 382. Drug Metab Dispos 31 (2003) 412-420
    • (2003) Drug Metab Dispos , vol.31 , pp. 412-420
    • Liu, J.1    Ericksen, S.S.2    Sivaneri, M.3    Besspiata, D.4    Fisher, C.W.5    Szklarz, G.D.6
  • 53
    • 4444223703 scopus 로고    scopus 로고
    • Aryl hydrocarbon receptor activation of an antitumor aminoflavone: basis of selective toxicity for MCF-7 breast tumor cells
    • Loaiza-Pérez A.I., Kenney S., Boswell J., Hollingshead M., Alley M.C., Hose C., et al. Aryl hydrocarbon receptor activation of an antitumor aminoflavone: basis of selective toxicity for MCF-7 breast tumor cells. Mol Cancer Ther 3 (2004) 715-725
    • (2004) Mol Cancer Ther , vol.3 , pp. 715-725
    • Loaiza-Pérez, A.I.1    Kenney, S.2    Boswell, J.3    Hollingshead, M.4    Alley, M.C.5    Hose, C.6
  • 54
    • 0037248572 scopus 로고    scopus 로고
    • Micronised purified flavonoid fraction: a review of its use in chronic venous insufficiency, venous ulcers and haemorrhoids
    • Lyseng-Williamson K.A., and Perry C.M. Micronised purified flavonoid fraction: a review of its use in chronic venous insufficiency, venous ulcers and haemorrhoids. Drugs 63 (2003) 71-100
    • (2003) Drugs , vol.63 , pp. 71-100
    • Lyseng-Williamson, K.A.1    Perry, C.M.2
  • 55
    • 4444223732 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes: novel options for cancer therapeutics
    • McFadyen M.C., Melwin W.T., and Murray G.I. Cytochrome P450 enzymes: novel options for cancer therapeutics. Mol Cancer Ther 3 (2004) 363-371
    • (2004) Mol Cancer Ther , vol.3 , pp. 363-371
    • McFadyen, M.C.1    Melwin, W.T.2    Murray, G.I.3
  • 56
    • 33646463990 scopus 로고    scopus 로고
    • Cytochrome P450 1B1: a novel anticancer therapeutic target
    • McFadyen M.C., and Murray G.I. Cytochrome P450 1B1: a novel anticancer therapeutic target. Future Oncol 2 (2005) 259-263
    • (2005) Future Oncol , vol.2 , pp. 259-263
    • McFadyen, M.C.1    Murray, G.I.2
  • 57
    • 0036765669 scopus 로고    scopus 로고
    • In vitro effects of genistein on the synthesis and distribution of glycosaminoglycans/proteoglycans by estrogen receptor-positive and -negative human breast cancer epithelial cells
    • Mitropoulou T.N., Tzanakakis G.N., Nikitovic D., Tsatsakis A., and Karamanos N.K. In vitro effects of genistein on the synthesis and distribution of glycosaminoglycans/proteoglycans by estrogen receptor-positive and -negative human breast cancer epithelial cells. Anticancer Res 22 (2002) 2841-2846
    • (2002) Anticancer Res , vol.22 , pp. 2841-2846
    • Mitropoulou, T.N.1    Tzanakakis, G.N.2    Nikitovic, D.3    Tsatsakis, A.4    Karamanos, N.K.5
  • 58
    • 0043063961 scopus 로고    scopus 로고
    • Antioxidative flavonoid quercetin: implication of its intestinal absorption and metabolism
    • Murota K., and Terao J. Antioxidative flavonoid quercetin: implication of its intestinal absorption and metabolism. Arch Biochem Biophys 417 (2003) 12-17
    • (2003) Arch Biochem Biophys , vol.417 , pp. 12-17
    • Murota, K.1    Terao, J.2
  • 59
    • 0028805027 scopus 로고
    • The immunohistochemical localization of drug-metabolizing enzymes in prostate cancer
    • Murray G.I., Taylor V.E., McKay J.A., Weaver R.J., Ewen S.W., Melvin W.T., et al. The immunohistochemical localization of drug-metabolizing enzymes in prostate cancer. J Pathol 177 (1995) 147-152
    • (1995) J Pathol , vol.177 , pp. 147-152
    • Murray, G.I.1    Taylor, V.E.2    McKay, J.A.3    Weaver, R.J.4    Ewen, S.W.5    Melvin, W.T.6
  • 61
    • 0037233849 scopus 로고    scopus 로고
    • The effects of genistein on the synthesis and distribution of glycosaminoglycans/proteoglycans by two osteosarcoma cell lines depends on tyrosine kinase and the estrogen receptor density
    • Nikitovic D., Tsatsakis A.M., Karamanos N.K., and Tzanakakis G.N. The effects of genistein on the synthesis and distribution of glycosaminoglycans/proteoglycans by two osteosarcoma cell lines depends on tyrosine kinase and the estrogen receptor density. Anticancer Res 23 (2003) 459-464
    • (2003) Anticancer Res , vol.23 , pp. 459-464
    • Nikitovic, D.1    Tsatsakis, A.M.2    Karamanos, N.K.3    Tzanakakis, G.N.4
  • 62
    • 0036146585 scopus 로고    scopus 로고
    • Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9
    • Otake Y., and Walle T. Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9. Drug Metab Dispos 30 (2002) 103-105
    • (2002) Drug Metab Dispos , vol.30 , pp. 103-105
    • Otake, Y.1    Walle, T.2
  • 63
    • 0036241543 scopus 로고    scopus 로고
    • Glucuronidation versus oxidation of the flavonoid galangin by human liver microsomes and hepatocytes
    • Otake Y., Hsieh F., and Walle T. Glucuronidation versus oxidation of the flavonoid galangin by human liver microsomes and hepatocytes. Drug Metab Dispos 30 (2002) 576-581
    • (2002) Drug Metab Dispos , vol.30 , pp. 576-581
    • Otake, Y.1    Hsieh, F.2    Walle, T.3
  • 64
    • 0031581817 scopus 로고    scopus 로고
    • Distinction of CYP1A1 and CYP1A2 activity by selective inhibition using fluvoxamine and isosafrole
    • Pastrakuljic A., Tang B.K., Roberts E.A., and Kalow W. Distinction of CYP1A1 and CYP1A2 activity by selective inhibition using fluvoxamine and isosafrole. Biochem Pharmacol 53 (1997) 531-538
    • (1997) Biochem Pharmacol , vol.53 , pp. 531-538
    • Pastrakuljic, A.1    Tang, B.K.2    Roberts, E.A.3    Kalow, W.4
  • 65
    • 0036015562 scopus 로고    scopus 로고
    • Tumor cytochrome P450 and drug activation
    • Patterson L.H., and Murray G.I. Tumor cytochrome P450 and drug activation. Curr Pharm Des 15 (2002) 1335-1347
    • (2002) Curr Pharm Des , vol.15 , pp. 1335-1347
    • Patterson, L.H.1    Murray, G.I.2
  • 66
    • 42149112242 scopus 로고    scopus 로고
    • Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation
    • Paysant J., Sansilvestri-Morel P., Bouskela E., and Verbeuren T.J. Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation. Int Angiol 27 (2008) 81-85
    • (2008) Int Angiol , vol.27 , pp. 81-85
    • Paysant, J.1    Sansilvestri-Morel, P.2    Bouskela, E.3    Verbeuren, T.J.4
  • 67
    • 0042510053 scopus 로고    scopus 로고
    • Effect of daidzein on CYP1A2 activity and pharmacokinetics of theophylline in healthy volunteers
    • Peng W.X., Li H.D., and Zhou H.H. Effect of daidzein on CYP1A2 activity and pharmacokinetics of theophylline in healthy volunteers. Eur J Clin Pharmacol 59 (2003) 237-241
    • (2003) Eur J Clin Pharmacol , vol.59 , pp. 237-241
    • Peng, W.X.1    Li, H.D.2    Zhou, H.H.3
  • 68
    • 33745617086 scopus 로고    scopus 로고
    • Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1
    • Peterson S., Lampe J.W., Bammler T.K., Gross-Steinmeyer K., and Eaton D.L. Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1. Food Chem Toxicol 44 (2006) 1474-1484
    • (2006) Food Chem Toxicol , vol.44 , pp. 1474-1484
    • Peterson, S.1    Lampe, J.W.2    Bammler, T.K.3    Gross-Steinmeyer, K.4    Eaton, D.L.5
  • 69
    • 0031864029 scopus 로고    scopus 로고
    • Prospects for bioreductive drug development
    • Phillips R.M. Prospects for bioreductive drug development. Expert Opin Investig Drugs 6 (1998) 905-928
    • (1998) Expert Opin Investig Drugs , vol.6 , pp. 905-928
    • Phillips, R.M.1
  • 70
    • 18344372908 scopus 로고    scopus 로고
    • The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1
    • Potter G.A., Patterson L.H., Wanogho E., Perry P.J., Butler P.C., Ijac T., et al. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br J Cancer 86 (2002) 774-778
    • (2002) Br J Cancer , vol.86 , pp. 774-778
    • Potter, G.A.1    Patterson, L.H.2    Wanogho, E.3    Perry, P.J.4    Butler, P.C.5    Ijac, T.6
  • 72
    • 6344277277 scopus 로고    scopus 로고
    • Inhibition of extrahepatic human cytochrome P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pretense (red clover)
    • Roberts D.W., Doerge D.R., Churchwell M.I., Gamboa da Costa G., Marques M.M., and Tolleson W.H. Inhibition of extrahepatic human cytochrome P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pretense (red clover). J Agric Food Chem 52 (2004) 6623-6632
    • (2004) J Agric Food Chem , vol.52 , pp. 6623-6632
    • Roberts, D.W.1    Doerge, D.R.2    Churchwell, M.I.3    Gamboa da Costa, G.4    Marques, M.M.5    Tolleson, W.H.6
  • 73
    • 34347235844 scopus 로고    scopus 로고
    • Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2
    • Sansen S., Yano J.K., Reynald R.L., Schoch G.A., Griffin K.J., Stout C.D., et al. Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J Biol Chem 282 (2007) 14348-14355
    • (2007) J Biol Chem , vol.282 , pp. 14348-14355
    • Sansen, S.1    Yano, J.K.2    Reynald, R.L.3    Schoch, G.A.4    Griffin, K.J.5    Stout, C.D.6
  • 74
    • 0033863355 scopus 로고    scopus 로고
    • Dietary intake and bioavailability of dietary polyphenols
    • Scalbert A., and Williamson G. Dietary intake and bioavailability of dietary polyphenols. J Nutr 130 (2000) 2073S-2085S
    • (2000) J Nutr , vol.130
    • Scalbert, A.1    Williamson, G.2
  • 75
    • 0037432647 scopus 로고    scopus 로고
    • In vitro assessment of inhibition by natural polyphenols of metabolic activation of procarcinogens by human CYP1A1
    • Schwarz D., and Roots I. In vitro assessment of inhibition by natural polyphenols of metabolic activation of procarcinogens by human CYP1A1. Biochem Biophys Res Commun 303 (2003) 902-907
    • (2003) Biochem Biophys Res Commun , vol.303 , pp. 902-907
    • Schwarz, D.1    Roots, I.2
  • 76
    • 0345707567 scopus 로고    scopus 로고
    • St John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7, 8-dihydrodiol by human CYP1A1
    • Schwarz D., Kisselev P., and Roots I. St John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7, 8-dihydrodiol by human CYP1A1. Cancer Res 63 (2003) 8062-8068
    • (2003) Cancer Res , vol.63 , pp. 8062-8068
    • Schwarz, D.1    Kisselev, P.2    Roots, I.3
  • 77
    • 11144269768 scopus 로고    scopus 로고
    • CYP1A1 genotype-selective inhibition of benzo[a]pyrene activation by quercetin
    • Schwarz D., Kisselev P., and Roots I. CYP1A1 genotype-selective inhibition of benzo[a]pyrene activation by quercetin. Eur J Cancer 41 (2005) 151-158
    • (2005) Eur J Cancer , vol.41 , pp. 151-158
    • Schwarz, D.1    Kisselev, P.2    Roots, I.3
  • 78
    • 1142275258 scopus 로고    scopus 로고
    • Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1
    • Shimada T., and Fujii-Kuriyama Y. Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1. Cancer Sci 95 (2004) 1-6
    • (2004) Cancer Sci , vol.95 , pp. 1-6
    • Shimada, T.1    Fujii-Kuriyama, Y.2
  • 79
    • 0028842375 scopus 로고
    • Heterogeneous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes
    • Siess M.H., Leclerc J., Canivenc-Lavier M.C., Rat P., and Suschetet M. Heterogeneous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicol Appl Pharmacol 130 (1995) 73-78
    • (1995) Toxicol Appl Pharmacol , vol.130 , pp. 73-78
    • Siess, M.H.1    Leclerc, J.2    Canivenc-Lavier, M.C.3    Rat, P.4    Suschetet, M.5
  • 80
    • 0030773207 scopus 로고    scopus 로고
    • Involvement of rat cytochrome 1A1 in the biotransformation of kaempferol to quercetin: relevance to the genotoxicity of kaempferol
    • Silva I.D., Rodrigues A.S., Gaspar J., Maia R., Laires A., and Rueff J. Involvement of rat cytochrome 1A1 in the biotransformation of kaempferol to quercetin: relevance to the genotoxicity of kaempferol. Mutagenesis 12 (1997) 383-390
    • (1997) Mutagenesis , vol.12 , pp. 383-390
    • Silva, I.D.1    Rodrigues, A.S.2    Gaspar, J.3    Maia, R.4    Laires, A.5    Rueff, J.6
  • 81
    • 0031417008 scopus 로고    scopus 로고
    • Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids diosmin and hesperidin
    • Tanaka T., Makita H., Kawabata K., Mori H., Kakumoto M., Satoh K., et al. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids diosmin and hesperidin. Carcinogenesis 18 (1997) 957-965
    • (1997) Carcinogenesis , vol.18 , pp. 957-965
    • Tanaka, T.1    Makita, H.2    Kawabata, K.3    Mori, H.4    Kakumoto, M.5    Satoh, K.6
  • 83
    • 1642528478 scopus 로고    scopus 로고
    • Absorption and metabolism of flavonoids
    • Walle T. Absorption and metabolism of flavonoids. Free Rad Biol Med 36 (2004) 829-837
    • (2004) Free Rad Biol Med , vol.36 , pp. 829-837
    • Walle, T.1
  • 84
    • 35548940326 scopus 로고    scopus 로고
    • Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones
    • Walle U.K., and Walle T. Bioavailable flavonoids: cytochrome P450-mediated metabolism of methoxyflavones. Drug Metab Dispos 35 (2007) 1985-1989
    • (2007) Drug Metab Dispos , vol.35 , pp. 1985-1989
    • Walle, U.K.1    Walle, T.2
  • 86
    • 0034795649 scopus 로고    scopus 로고
    • Carbon dioxide is the major metabolite of quercetin in humans
    • Walle T., Walle U.K., and Halushka P.V. Carbon dioxide is the major metabolite of quercetin in humans. J Nutr 131 (2001) 2648-2652
    • (2001) J Nutr , vol.131 , pp. 2648-2652
    • Walle, T.1    Walle, U.K.2    Halushka, P.V.3
  • 87
    • 33947359919 scopus 로고    scopus 로고
    • Cancer chemopreventive properties of orally bioavailable flavonoids-methylated versus unmethylated flavones
    • Walle T., Ta N., Kawamori T., Wen X., Tsuji P.A., and Walle U.K. Cancer chemopreventive properties of orally bioavailable flavonoids-methylated versus unmethylated flavones. Biochem Pharmacol 73 (2007) 1288-1296
    • (2007) Biochem Pharmacol , vol.73 , pp. 1288-1296
    • Walle, T.1    Ta, N.2    Kawamori, T.3    Wen, X.4    Tsuji, P.A.5    Walle, U.K.6
  • 88
    • 0031686175 scopus 로고    scopus 로고
    • Isoflavone genistein inhibits the initiation and promotion of two-stage skin carcinogenesis in mice
    • Wei H.C., Bowen R., Zhang X.S., and Lebwohl M. Isoflavone genistein inhibits the initiation and promotion of two-stage skin carcinogenesis in mice. Carcinogenesis 19 (1998) 1509-1514
    • (1998) Carcinogenesis , vol.19 , pp. 1509-1514
    • Wei, H.C.1    Bowen, R.2    Zhang, X.S.3    Lebwohl, M.4
  • 89
    • 27144443044 scopus 로고    scopus 로고
    • Preferential induction of CYP1B1 by benzo[a]pyrene in human oral epithelial cells: impact on DNA adduct formation and prevention by polyphenols
    • Wen X., and Walle T. Preferential induction of CYP1B1 by benzo[a]pyrene in human oral epithelial cells: impact on DNA adduct formation and prevention by polyphenols. Carcinogenesis 26 (2005) 1774-1781
    • (2005) Carcinogenesis , vol.26 , pp. 1774-1781
    • Wen, X.1    Walle, T.2
  • 90
    • 33748916241 scopus 로고    scopus 로고
    • Methylated flavonoids have greatly improved intestinal absorption and metabolic stability
    • Wen X., and Walle T. Methylated flavonoids have greatly improved intestinal absorption and metabolic stability. Drug Metab Dispos 34 (2006) 1786-1792
    • (2006) Drug Metab Dispos , vol.34 , pp. 1786-1792
    • Wen, X.1    Walle, T.2
  • 91
    • 17844394448 scopus 로고    scopus 로고
    • 5, 7-Dimethoxyflavone downregulates CYP1A1 expression and benzo[a]pyrene-induced DNA binding in Hep G2 cells
    • Wen X., Walle U.K., and Walle T. 5, 7-Dimethoxyflavone downregulates CYP1A1 expression and benzo[a]pyrene-induced DNA binding in Hep G2 cells. Carcinogenesis 26 (2005) 803-809
    • (2005) Carcinogenesis , vol.26 , pp. 803-809
    • Wen, X.1    Walle, U.K.2    Walle, T.3
  • 92
    • 0042265520 scopus 로고    scopus 로고
    • Crystal structure of human cytochrome P450 2C9 with bound warfarin
    • Williams P.A., Cosme J., Ward A., Angove H.C., Matak Vinkovic D., et al. Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature 424 (2003) 464-468
    • (2003) Nature , vol.424 , pp. 464-468
    • Williams, P.A.1    Cosme, J.2    Ward, A.3    Angove, H.C.4    Matak Vinkovic, D.5
  • 93
    • 0031785065 scopus 로고    scopus 로고
    • Comparative inhibition of human cytochrome P450 1A1 and 1A2 by flavonoids
    • Zhai S., Dai R., Friedman F.K., and Vestal R.E. Comparative inhibition of human cytochrome P450 1A1 and 1A2 by flavonoids. Drug Metab Dispos 26 (1998) 989-992
    • (1998) Drug Metab Dispos , vol.26 , pp. 989-992
    • Zhai, S.1    Dai, R.2    Friedman, F.K.3    Vestal, R.E.4
  • 94
    • 0032541119 scopus 로고    scopus 로고
    • Inhibition of methoxyresorufin demethylase activity by flavonoids in human liver microsomes
    • Zhai S., Dai R., Wei X., Friedman F.K., and Vestal R.E. Inhibition of methoxyresorufin demethylase activity by flavonoids in human liver microsomes. Life Sci 63 (1998) 119-123
    • (1998) Life Sci , vol.63 , pp. 119-123
    • Zhai, S.1    Dai, R.2    Wei, X.3    Friedman, F.K.4    Vestal, R.E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.