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Volumn 16, Issue 2, 2014, Pages 258-268

Dietary flavonoids modulate CYP2C to improve drug oral bioavailability and their qualitative/quantitative structure-activity relationship

Author keywords

bioavailability; CYP2C; flavonoid; structure activity relationship; tamarixetin

Indexed keywords

4 HYDROXYTOLBUTAMIDE; CYTOCHROME P450 2C; CYTOCHROME P450 INHIBITOR; FLAVONOID; FLUINDOSTATIN; TAMARIXETIN; TOLBUTAMIDE; UNCLASSIFIED DRUG;

EID: 84895860767     PISSN: 15507416     EISSN: None     Source Type: Journal    
DOI: 10.1208/s12248-013-9549-4     Document Type: Article
Times cited : (10)

References (47)
  • 1
    • 17644380257 scopus 로고    scopus 로고
    • Predicting drug disposition via application of BCS: Transport/absorption/ elimination interplay and development of a biopharmaceutics drug disposition classification system
    • DOI 10.1007/s11095-004-9004-4
    • Wu CY, Benet LZ. Predicting drug disposition via application of BCS: transport/absorption/elimination interplay and development of a biopharmaceutics drug disposition classification system. Pharm Res. 2005;22:11-23. (Pubitemid 40558141)
    • (2005) Pharmaceutical Research , vol.22 , Issue.1 , pp. 11-23
    • Wu, C.-Y.1    Benet, L.Z.2
  • 4
    • 0346220388 scopus 로고    scopus 로고
    • Herbal bioactivation: The good, the bad and the ugly
    • DOI 10.1016/j.lfs.2003.09.035
    • Zhou S, Koh HL, Gao Y, Gong ZY, Lee EJD. Herbal bioactivation: the good, the bad and the ugly. Life Sci. 2004;74:935-68. (Pubitemid 37522131)
    • (2004) Life Sciences , vol.74 , Issue.8 , pp. 935-968
    • Zhou, S.1    Koh, H.-L.2    Gao, Y.3    Gong, Z.-Y.4    Lee, E.J.D.5
  • 5
    • 0036720280 scopus 로고    scopus 로고
    • Recent advances in the discovery of flavonoids and analogs with high-affinity binding to P-glycoprotein responsible for cancer cell multidrug resistance
    • Boumendjel A, Pietro AD, Dumontet C, Barron D. Recent advances in the discovery of flavonoids and analogs with high-affinity binding to P-glycoprotein responsible for cancer cell multidrug resistance. Med Res Rev. 2002;22:512-29.
    • (2002) Med Res Rev , vol.22 , pp. 512-529
    • Boumendjel, A.1    Pietro, A.D.2    Dumontet, C.3    Barron, D.4
  • 6
    • 33749444911 scopus 로고    scopus 로고
    • The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms
    • DOI 10.2174/138920006778520570
    • Cermak R, Wolffram S. The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms. Curr Drug Metab. 2006;7:729-44. (Pubitemid 44509679)
    • (2006) Current Drug Metabolism , vol.7 , Issue.7 , pp. 729-744
    • Cermak, R.1    Wolffram, S.2
  • 7
    • 39049146064 scopus 로고    scopus 로고
    • Effect of dietary flavonoids on pathways involved in drug metabolism
    • DOI 10.1517/17425255.4.1.17
    • Cermak R. Effect of dietary flavonoids on pathways involved in drug metabolism. Expert Opin Drug Metab Toxicol. 2008;4:17-35. (Pubitemid 351234098)
    • (2008) Expert Opinion on Drug Metabolism and Toxicology , vol.4 , Issue.1 , pp. 17-35
    • Cermak, R.1
  • 9
    • 0033863355 scopus 로고    scopus 로고
    • Dietary intake and bioavailability of polyphenols
    • Scalbert A, Williamson G. Dietary intake and bioavailability of polyphenols. J Nutr. 2000;130(Suppl):2073-85.
    • (2000) J Nutr , vol.130 , Issue.SUPPL. , pp. 2073-2085
    • Scalbert, A.1    Williamson, G.2
  • 10
    • 30644456411 scopus 로고    scopus 로고
    • Dietary flavonoids: Effects on xenobiotic and carcinogen metabolism
    • DOI 10.1016/j.tiv.2005.06.048, PII S0887233305002080
    • Moon YJ, Wang X, Morris ME. Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Toxicol in Vitro. 2006;20:187-210. (Pubitemid 43087702)
    • (2006) Toxicology in Vitro , vol.20 , Issue.2 , pp. 187-210
    • Moon, Y.J.1    Wang, X.2    Morris, M.E.3
  • 11
    • 0028054999 scopus 로고
    • Extrahepatic metabolism of drugs in humans
    • Krishna D, Klotz U. Extrahepatic metabolism of drugs in humans. Clin Pharmacokinet. 1994;26:144-60. (Pubitemid 24064238)
    • (1994) Clinical Pharmacokinetics , vol.26 , Issue.2 , pp. 144-160
    • Krishna, D.R.1    Klotz, U.2
  • 12
    • 0030834058 scopus 로고    scopus 로고
    • Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors
    • Rendic S, di Carlo FJ. Human cytochrome P450s enzymes: a status report summarizing their reactions, substances, inducers, and inhibitors. Drug Metab Rev. 2001;29:413-580. (Pubitemid 27293618)
    • (1997) Drug Metabolism Reviews , vol.29 , Issue.1-2 , pp. 413-580
    • Rendic, S.1    Di, C.F.J.2
  • 13
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. Interindividual variations in human liver cytochrome P450s enzymes involved in the oxidation of drugs, carcinogens and toxic chemical: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther. 1994;270:414-23. (Pubitemid 24229655)
    • (1994) Journal of Pharmacology and Experimental Therapeutics , vol.270 , Issue.1 , pp. 414-423
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 14
    • 0034792584 scopus 로고    scopus 로고
    • Clinical relevance of genetic polymorphisms in the human CYP2C subfamily
    • DOI 10.1046/j.0306-5251.2001.01499.x
    • Goldstein JA. Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Brit J Clin Pharmacol. 2001;52:349-55. (Pubitemid 32939439)
    • (2001) British Journal of Clinical Pharmacology , vol.52 , Issue.4 , pp. 349-355
    • Goldstein, J.A.1
  • 16
    • 0037131892 scopus 로고    scopus 로고
    • CYP2C9 allelic variants: Ethnic distribution and functional significance
    • DOI 10.1016/S0169-409X(02)00076-5, PII S0169409X02000765
    • Xie HG, Prasad HC, Kim RB, Stein CM. CYP2C9 allelic variants: ethnic distribution and functional significance. Adv Drug Deliv Rev. 2002;54:1257-70. (Pubitemid 35284252)
    • (2002) Advanced Drug Delivery Reviews , vol.54 , Issue.10 , pp. 1257-1270
    • Xie, H.-G.1    Prasad, H.C.2    Kim, R.B.3    Stein, C.M.4
  • 17
    • 0036909078 scopus 로고    scopus 로고
    • Improvement of oral drug treatment by temporary inhibition of drug transporters and/or cytochrome P450 in the gastrointestinal tract and liver: An overview
    • DOI 10.1634/theoncologist.7-6-516
    • Kruijtzer CMF, Beijnen JH, Schellens JHM. Improvement of oral drug treatment by temporary inhibition of drug transporters and/or cytochrome P450 in the gastrointestinal tract and liver: an overview. Oncologist. 2002;7:516-30. (Pubitemid 36009000)
    • (2002) Oncologist , vol.7 , Issue.6 , pp. 516-530
    • Kruijtzer, C.M.F.1    Beijnen, J.H.2    Schellens, J.H.M.3
  • 18
    • 0037478407 scopus 로고    scopus 로고
    • Human Extrahepatic Cytochromes P450: Function in Xenobiotic Metabolism and Tissue-Selective Chemical Toxicity in the Respiratory and Gastrointestinal Tracts
    • DOI 10.1146/annurev.pharmtox.43.100901.140251
    • Ding X, Kaminsky LS. Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol. 2003;43:149-73. (Pubitemid 37372638)
    • (2003) Annual Review of Pharmacology and Toxicology , vol.43 , pp. 149-173
    • Ding, X.1    Kaminsky, L.S.2
  • 19
    • 13844271387 scopus 로고    scopus 로고
    • Bioavailability and bioefficacy of polyphenols in human. II. Review of 93 intervention studies
    • Williamson G, Manach C. Bioavailability and bioefficacy of polyphenols in human. II. Review of 93 intervention studies. Am J Clin Nutr. 2005;81 Suppl 1:243-55.
    • (2005) Am J Clin Nutr , vol.81 , Issue.SUPPL. 1 , pp. 243-255
    • Williamson, G.1    Manach, C.2
  • 21
    • 78449259627 scopus 로고    scopus 로고
    • Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro
    • Quintieri L, Bortolozzo S, Straliotto S, Moro S, Pavanetto M, Nassi A, et al. Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro. Drug Metab Pharmacokinet. 2010;25:466-76.
    • (2010) Drug Metab Pharmacokinet , vol.25 , pp. 466-476
    • Quintieri, L.1    Bortolozzo, S.2    Straliotto, S.3    Moro, S.4    Pavanetto, M.5    Nassi, A.6
  • 22
    • 72149090100 scopus 로고    scopus 로고
    • Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity
    • Kimura Y, Ito H, Ohnishi R, Hatano T. Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity. Food Chem Toxicol. 2010;48:429-35.
    • (2010) Food Chem Toxicol , vol.48 , pp. 429-435
    • Kimura, Y.1    Ito, H.2    Ohnishi, R.3    Hatano, T.4
  • 23
    • 0036893593 scopus 로고    scopus 로고
    • Evaluation of cytochrome p450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions
    • DOI 10.1124/dmd.30.12.1311
    • Yuan R, Madani S, Wei XX, Reynolds K, Huang SM. Evaluation of cytochrome P450s probe substrates commonly used by the pharmaceutical industry to study in vitro drug interaction. Drug Metab Dispos. 2002;30:1311-9. (Pubitemid 35397032)
    • (2002) Drug Metabolism and Disposition , vol.30 , Issue.12 , pp. 1311-1319
    • Yuan, R.1    Madani, S.2    Wei, X.-X.3    Reynolds, K.4    Huang, S.-M.5
  • 24
    • 70350025073 scopus 로고    scopus 로고
    • Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes
    • Toda T, Eliasson E, Ask B, Inotsume N, Rane A. Roles of different CYP enzymes in the formation of specific fluvastatin metabolites by human liver microsomes. Basic Clin Pharmacol Toxicol. 2009;105:327-32.
    • (2009) Basic Clin Pharmacol Toxicol , vol.105 , pp. 327-332
    • Toda, T.1    Eliasson, E.2    Ask, B.3    Inotsume, N.4    Rane, A.5
  • 25
    • 0035023185 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of fluvastatin
    • Scripture CD, Pieper JA. Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40:263-81. (Pubitemid 32458153)
    • (2001) Clinical Pharmacokinetics , vol.40 , Issue.4 , pp. 263-281
    • Scripture, C.D.1    Pieper, J.A.2
  • 26
    • 77956304287 scopus 로고    scopus 로고
    • A quantitative structure-activity relationship for the modulation effects of flavonoids on P-glycoprotein-mediated transport
    • Sheu MT, Liou YB, Kao YH, Lin YK, Ho HO. A quantitative structure-activity relationship for the modulation effects of flavonoids on P-glycoprotein-mediated transport. Chem Pharm Bull. 2010;58:1187-94.
    • (2010) Chem Pharm Bull , vol.58 , pp. 1187-1194
    • Sheu, M.T.1    Liou, Y.B.2    Kao, Y.H.3    Lin, Y.K.4    Ho, H.O.5
  • 27
    • 84863057043 scopus 로고    scopus 로고
    • Herb-drug interaction of 50 Chinese herbal medicines on CYP3A4 activity in vitro and in vivo
    • Pao LH, Hu OYP, Fan HY, Lin CC, Liu LC, Huang PW. Herb-drug interaction of 50 Chinese herbal medicines on CYP3A4 activity in vitro and in vivo. Am J Chin Med. 2012;40:57-73.
    • (2012) Am J Chin Med , vol.40 , pp. 57-73
    • Pao, L.H.1    Hu, O.Y.P.2    Fan, H.Y.3    Lin, C.C.4    Liu, L.C.5    Huang, P.W.6
  • 29
    • 0023873591 scopus 로고
    • Tolbutamide hydroxylation by human liver microsomes. Kinetic characterisation and relationship to other cytochrome P-450 dependent xenobiotic oxidations
    • DOI 10.1016/0006-2952(88)90522-9
    • Miners JO, Smith KJ, Robson RA, McManus ME, Veronese ME, Birkett DJ. Tolbutamide hydroxylation by human liver microsomes: kinetic characterisation and relationship to other cytochrome P450 dependent xenobiotic oxidations. Biochem Pharmacol. 1988;37:1137-44. (Pubitemid 18066470)
    • (1988) Biochemical Pharmacology , vol.37 , Issue.6 , pp. 1137-1144
    • Miners, J.O.1    Smith, K.J.2    Robson, R.A.3    McManus, M.E.4    Veronese, M.E.5    Birkett, D.J.6
  • 30
    • 0031962621 scopus 로고    scopus 로고
    • Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes
    • DOI 10.1046/j.1365-2125.1998.00679.x
    • Eagling VA, Tjia JF, Back DJ. Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes. Br J Clin Pharmacol. 1998;45:107-14. (Pubitemid 28045676)
    • (1998) British Journal of Clinical Pharmacology , vol.45 , Issue.2 , pp. 107-114
    • Eagling, V.A.1    Tjia, J.F.2    Back, D.J.3
  • 31
    • 0029978107 scopus 로고    scopus 로고
    • Determination of fluvastatin enantiomers and the racemate in human blood plasma by liquid chromatography and fluorometric detection
    • DOI 10.1016/0021-9673(95)00897-7
    • Toreson H, Eriksson BM. Determination of fluvastatin enantiomers and the racemate in human blood plasma by liquid chromatography and fluorometric detection. J Chromatogr A. 1996;729:13-8. (Pubitemid 26135002)
    • (1996) Journal of Chromatography A , vol.729 , Issue.1-2 , pp. 13-18
    • Toreson, H.1    Eriksson, B.-M.2
  • 32
    • 29844435006 scopus 로고    scopus 로고
    • Inhibitory effects of polyphenols on P-glycoprotein-mediated transport
    • DOI 10.1248/bpb.29.1
    • Kitagawa S. Inhibitory effects of polyphenols on P-glycoprotein-mediated transporter. Biol Pharm Bull. 2006;29:1-6. (Pubitemid 43036683)
    • (2006) Biological and Pharmaceutical Bulletin , vol.29 , Issue.1 , pp. 1-6
    • Kitagawa, S.1
  • 33
    • 78650456545 scopus 로고    scopus 로고
    • Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives
    • Shimada T, Tanaka K, Takenaka S, Murayama N, Martin MV, Foroozesh MK, et al. Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010;23:1921-35.
    • (2010) Chem Res Toxicol , vol.23 , pp. 1921-1935
    • Shimada, T.1    Tanaka, K.2    Takenaka, S.3    Murayama, N.4    Martin, M.V.5    Foroozesh, M.K.6
  • 34
    • 1242294387 scopus 로고    scopus 로고
    • A Constituent of Green Tea, Epigallocatechin-3-gallate, Activates Endothelial Nitric Oxide Synthase by a Phosphatidylinositol-3-OH-kinase-, cAMP-dependent Protein Kinase-, and Akt-dependent Pathway and Leads to Endothelial-dependent Vasorelaxation
    • DOI 10.1074/jbc.M309114200
    • Lorenz M, Wessler S, Follmann E, Michaelis W, Dusterhoft T, Baumann G, et al. A constituent of green tea, epigallocatechin-3-gallate, activates endothelial nitric oxide synthase by a phosphatidylinositol-3-OH-kinase-, cAMP-dependent protein kinase-, and Akt-dependent pathway and leads to endothelial-dependent vasorelaxation. J Biol Chem. 2004;279:6190-5. (Pubitemid 38220652)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.7 , pp. 6190-6195
    • Lorenz, M.1    Wessler, S.2    Follmann, E.3    Michaelis, W.4    Dusterhoft, T.5    Baumann, G.6    Stangl, K.7    Stangl, V.8
  • 36
    • 0031958268 scopus 로고    scopus 로고
    • In vitro biotransformation of flavonoids by rat liver microsomes
    • DOI 10.1080/004982598239498
    • Nielsen SE, Breinholt V, Justesen U, Cornett C, Dragsted LO. In vitro biotransformation of flavonoids by rat liver microsomes. Xenobiotica. 1998;29:389-401. (Pubitemid 28207043)
    • (1998) Xenobiotica , vol.28 , Issue.4 , pp. 389-401
    • Nielsen, S.E.1    Breinholt, V.2    Justesen, U.3    Cornett, C.4    Dragsted, L.O.5
  • 37
    • 0036229022 scopus 로고    scopus 로고
    • In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids
    • DOI 10.1016/S0278-6915(01)00125-9, PII S0278691501001259
    • Breinholt VM, Offord EA, Brouwer C, Nielsen SE, Brosen K, Friedberg T. In vitro investigation of cytochrome P450s-mediated metabolism of dietary fl avonoids. Food Chem Toxicol. 2002;40:609-16. (Pubitemid 34310426)
    • (2002) Food and Chemical Toxicology , vol.40 , Issue.5 , pp. 609-616
    • Breinholt, V.M.1    Offord, E.A.2    Brouwer, C.3    Nielsen, S.E.4    Brosen, K.5    Friedberg, T.6
  • 38
    • 77949389166 scopus 로고    scopus 로고
    • A structure basis for the inhibition of collagen-stimulated platelet function by quercetin and structurally related flavonoids
    • Wright B, Moraes LA, Kemp CF, Mullen W, Crozier A, Lovegrove JA, et al. A structure basis for the inhibition of collagen-stimulated platelet function by quercetin and structurally related flavonoids. Br J Pharm. 2010;159:1312-25.
    • (2010) Br J Pharm , vol.159 , pp. 1312-1325
    • Wright, B.1    Moraes, L.A.2    Kemp, C.F.3    Mullen, W.4    Crozier, A.5    Lovegrove, J.A.6
  • 39
    • 1642528478 scopus 로고    scopus 로고
    • Absorption and metabolism of flavonoids
    • DOI 10.1016/j.freeradbiomed.2004.01.002, PII S0891584904000346
    • Walle T. Absorption and metabolism of flavonoids. Free Radic Biol Med. 2004;36:829-37. (Pubitemid 38401062)
    • (2004) Free Radical Biology and Medicine , vol.36 , Issue.7 , pp. 829-837
    • Walle, T.1
  • 40
    • 33846209551 scopus 로고    scopus 로고
    • Quantitative determination of isorhamnetin, quercetin and kaempferol in rat plasma by liquid chromatography with electrospray ionization tandem mass spectrometry and its application to the pharmacokinetic study of isorhamnetin
    • DOI 10.1002/rcm.2814
    • Lan K, Jiang XH, He JL. Quantitative determination of isorhamnetin, quercetin and kaempferol in rat plasma by liquid chromatography with electrospray ionization tandem mass spectrometry and its application to the pharmacokinetic study of isorhamnetin. Rapid Commun Mass Spectrom. 2007;21:112-20. (Pubitemid 46095469)
    • (2007) Rapid Communications in Mass Spectrometry , vol.21 , Issue.2 , pp. 112-120
    • Lan, K.1    Jiang, X.2    He, J.3
  • 42
    • 79955438343 scopus 로고    scopus 로고
    • Effects of cranberry juice consumption on vascular function in patients with coronary artery disease
    • Dohadwala MM, Holbrook M, Hamburg NM, Shenouda SM, Chung WB, Titas M, et al. Effects of cranberry juice consumption on vascular function in patients with coronary artery disease. Am J Clin Nutr. 2011;93:934-40.
    • (2011) Am J Clin Nutr , vol.93 , pp. 934-940
    • Dohadwala, M.M.1    Holbrook, M.2    Hamburg, N.M.3    Shenouda, S.M.4    Chung, W.B.5    Titas, M.6
  • 43
    • 79955655412 scopus 로고    scopus 로고
    • Citrus polyphenol hesperidin stimulates production of nitric oxide in endothelial cells while improving endothelial function and reducing inflammatory markers in patients with metabolic syndrome
    • Rizza S, Muniyappa R, Iantorno M, Kim JA, Chen H, Pullikotil P, et al. Citrus polyphenol hesperidin stimulates production of nitric oxide in endothelial cells while improving endothelial function and reducing inflammatory markers in patients with metabolic syndrome. J Clin Endocrinol Metab. 2011;96:E782-92.
    • (2011) J Clin Endocrinol Metab , vol.96
    • Rizza, S.1    Muniyappa, R.2    Iantorno, M.3    Kim, J.A.4    Chen, H.5    Pullikotil, P.6
  • 45
    • 80053942110 scopus 로고    scopus 로고
    • Which sources of flavonoids: Complex diets or dietary supplements?
    • Egert S, Rimbach G. Which sources of flavonoids: complex diets or dietary supplements? Adv Nutr. 2011;2:8-14.
    • (2011) Adv Nutr , vol.2 , pp. 8-14
    • Egert, S.1    Rimbach, G.2
  • 47
    • 0032520707 scopus 로고    scopus 로고
    • 5 in the reductive metabolism of 3'-azido-3'-deoxythymidine (AZT) to 3'-amino-3'-deoxythymidine
    • DOI 10.1016/S0006-2952(97)00538-8, PII S0006295297205388
    • Pan-Zhou XR, Cretton-Scott E, Zhou XJ, Yang MX, Lasker JM, Sommadossi JP. Role of human liver P450s and cytochrome b5 in the reductive metabolism of 3′-azido-3′-deoxythymidine (AZT) to 3′-amino-3′- deoxythymidine. Biochem Pharmacol. 1998;55:757-66. (Pubitemid 28329338)
    • (1998) Biochemical Pharmacology , vol.55 , Issue.6 , pp. 757-766
    • Pan-Zhou, X.-R.1    Cretton-Scott, E.2    Zhou, X.-J.3    Yang, M.-X.4    Lasker, J.M.5    Sommadossi, J.-P.6


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