Interactions between CYP3A4 and Dietary Polyphenols

Oxidative Medicine and Cellular Longevity

Volumn 2015, Issue , 2015, Pages

  Basheer, Loai ^a   Kerem, Zohar ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; DRUG INTERACTIONS; ENZYMES; PHYSIOLOGY; POLYPHENOLIC COMPOUNDS;

BROAD SPECTRUM; GUT MICROBIOTA; HUMAN CYTOCHROME; METABOLIC FATE; OXIDATIVE REACTION; POLYPHENOLICS; POLYPHENOLS; SMALL INTESTINE;

METABOLISM;

ANTHOCYANIN; COUMARIC ACID; CYTOCHROME P450 3A4; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; HYDROXYBENZOIC ACID DERIVATIVE; ISOFLAVONE DERIVATIVE; LIGNAN; PHENOL DERIVATIVE; POLYPHENOL; TANNIN DERIVATIVE; XENOBIOTIC AGENT; CYTOCHROME P450 3A; PHENOLIC ACID; STILBENE DERIVATIVE;

AEROBIC METABOLISM; CATALYSIS; DIETARY INTAKE; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME MODIFICATION; FOOD DRUG INTERACTION; HUMAN; IN VITRO STUDY; IN VIVO STUDY; INTESTINE FLORA; PROTEIN EXPRESSION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW; STRUCTURE ACTIVITY RELATION; CHEMISTRY; METABOLISM;

CYTOCHROME P-450 CYP3A; FLAVONOIDS; HUMANS; HYDROXYBENZOATES; POLYPHENOLS; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84935019074     PISSN: 19420900     EISSN: 19420994     Source Type: Journal    
DOI: 10.1155/2015/854015     Document Type: Review

References (211)

1. I. G. Denisov, T. M. Makris, S. G. Sligar, and I. Schlichting, "Structure and chemistry of cytochrome P450, " Chemical Reviews, vol. 105, no. 6, pp. 2253-2277, 2005
2. T. L. Domanski, Y. A. He, K. K. Khan, F. Roussel, Q. Wang, and J. R. Halpert, "Phenylalanine and tryptophan scanningmutagenesis of CYP3A4 substrate recognition site residues and effect on substrate oxidation and cooperativity, " Biochemistry, vol. 40, no. 34, pp. 10150-10160, 2001
3. D. W. Nebert and D. W. Russell, "Clinical importance of the cytochromes P450, "TheLancet, vol. 360, no.9340, pp. 1155-1162, 2002
4. P. R. O. deMontellano, Cytochrome P450: Structure, Mechanism, and Biochemistry, Springer, 3rd edition, 2005
5. D. R. Nelson, "The cytochrome P450 homepage, " Human Genomics, vol. 4, no. 1, pp. 59-65, 2009
6. D. R. Nelson, "A world of cytochrome P450s, " Philosophical transactions of the Royal Society of London, Series B: Biological Sciences, vol. 368, no. 1612, Article ID20120430, 2013
7. D. W. Nebert, K. Wikvall, and W. L. Miller, "Human cytochromes P450 in health and disease, " Philosophical transactions of the Royal Society of London. Series B, Biological sciences, vol. 368, no. 1612, Article ID 20120431, 2013
8. D. W. Nebert, D. R. Nelson, M. J. Coon et al., "The P450 superfamily: update on new sequences, gene mapping, and recommended nomenclature, "DNA and Cell Biology, vol. 10, no. 1, pp. 1-14, 1991
9. U. M. Zanger and M. Schwab, "Cytochrome P450 enzymes in drug metabolism: regulation of gene expression, enzyme activities, and impact of genetic variation, " Pharmacology & Therapeutics, vol. 138, no. 1, pp. 103-141, 2013
10. F. P. Guengerich, "Cytochrome P450 and chemical toxicology, " Chemical Research in Toxicology, vol. 21, no. 1, pp. 70-83, 2008
11. S. Ekins, D. M. Stresser, and J. A. Williams, "In vitro and pharmacophore insights into CYP3A enzymes, " Trends in Pharmacological Sciences, vol. 24, no. 4, pp. 161-166, 2003
12. K. S. Lown, D. G. Bailey, R. J. Fontana et al., "Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression, " The Journal of Clinical Investigation, vol. 99, no. 10, pp. 2545-2553, 1997
13. J. C. Kolars, K. S. Lown, P. Schmiedlin-Ren et al., "CYP3A gene expression in human gut epithelium, " Pharmacogenetics and Genomics, vol. 4, no. 5, pp. 247-259, 1994
14. C. S. Ferguson and R. F. Tyndale, "CytochromeP450enzymes in the brain: emerging evidence of biological significance, " Trends in Pharmacological Sciences, vol. 32, no. 12, pp. 708-714, 2011
15. C. Ghosh, N. Marchi, N. K. Desai et al., "Cellular localization and functional significance of CYP3A4 in the human epileptic brain, " Epilepsia, vol. 52, no. 3, pp. 562-571, 2011
16. F. P. Guengerich, "Cytochrome P-450 3A4: regulation and role in drug metabolism, " Annual Review of Pharmacology and Toxicology, vol. 39, pp. 1-17, 1999
17. Z. Huang, M. J. Fasco, H. L. Figge, K. Keyomarsi, and L. S. Kaminsky, "Expression of cytochromes P450 in human breast tissue and tumors, " Drug Metabolism and Disposition, vol. 24, no. 8, pp. 899-905, 1996
18. J. H. Lin, M. Chiba, and T. A. Baillie, "Is the role of the small intestine in first-pass metabolism overemphasized?" Pharmacological Reviews, vol. 51, no. 2, pp. 135-158, 1999
19. M. F. Paine, H. L. Hart, S. S. Ludington, R. L. Haining, A. E. Rettie, and D. C. Zeldin, "The human intestinal cytochrome P450 'pie', " Drug Metabolism & Disposition, vol. 34, no. 5, pp. 880-886, 2006
20. A. Galetin, M. Gertz, and J. B. Houston, "Contribution of intestinal cytochrome P450-mediated metabolism to drugdrug inhibition and induction interactions, " Drug Metabolism and Pharmacokinetics, vol. 25, no. 1, pp. 28-47, 2010
21. J. Yang, G. T. Tucker, and A. Rostami-Hodjegan, "Cytochrome P450 3A expression and activity in the human small intestine, " Clinical Pharmacology and Therapeutics, vol. 76, no. 4, article 391, 2004
22. M. F. Paine, M. Khalighi, J. M. Fisher et al., "Characterization of interintestinal and intraintestinal variations in human CYP3Adependent metabolism, " Journal of Pharmacology and Experimental Therapeutics, vol. 283, no. 3, pp. 1552-1562, 1997
23. F. H. Karlsson, S. Bouchene, C. Hilgendorf, H. Dolgos, and S. A. Peters, "Utility of in vitro systems and preclinical data for the prediction of human intestinal first-passmetabolismduring drug discovery and preclinical development, " Drug Metabolism and Disposition, vol. 41, no. 12, pp. 2033-2046, 2013
24. S. Siissalo and A. T. Heikkinen, "In vitro methods to study the interplay of drug metabolism and efflux in the intestine, " Current Drug Metabolism, vol. 14, no. 1, pp. 102-111, 2013
25. M. Gertz, J.D. Davis, A. Harrison, J. B. Houston, and A. Galetin, "Grapefruit juice-drug interaction studies as a method to assess the extent of intestinal availability: utility and limitations, " Current Drug Metabolism, vol. 9, no. 8, pp. 785-795, 2008
26. S. D. Hall, K. E. Thummel, P. B. Watkins et al., "Molecular and physical mechanisms of first-pass extraction, " DrugMetabolism and Disposition, vol. 27, no. 2, pp. 161-166, 1999
27. D. G. Bailey, G. Dresser, and J. M. O. Arnold, "Grapefruitmedication interactions: forbidden fruit or avoidable consequences?" Canadian Medical Association Journal, vol. 185, no. 4, pp. 309-316, 2013
28. M. Gertz, A. Harrison, J. B. Houston, and A. Galetin, "Prediction of human intestinal first-pass metabolism of 25 CYP3A substrates from in vitro clearance and permeability data, " Drug Metabolism and Disposition, vol. 38, no. 7, pp. 1147-1158, 2010
29. J. vanDuynhoven, E. E. Vaughan, D. M. Jacobs et al., "Metabolic fate of polyphenols in the human superorganism, " Proceedings of the National Academy of Sciences of the United States of America, vol. 108, no. 1, pp. 4531-4538, 2011
30. G. Williamson and M. N. Clifford, "Colonicmetabolites of berry polyphenols: the missing link to biological activity?" British Journal of Nutrition, vol. 104, supplement 3, pp. S48-S66, 2010
31. L. S. Kaminsky and Q.-Y. Zhang, "The small intestine as a xenobiotic-metabolizing organ, " Drug Metabolism and Disposition, vol. 31, no. 12, pp. 1520-1525, 2003
32. M. Martignoni, G. Groothuis, and R. deKanter, "Comparisonof mouse and rat cytochrome P450-mediated metabolism in liver and intestine, " Drug Metabolism and Disposition, vol. 34, no. 6, pp. 1047-1054, 2006
33. M. Lindell, M. Lang, and H. Lennerns, "Expression of genes encoding for drug metabolising cytochrome P450 enzymes and P-glycoprotein in the rat small intestine; comparison to the liver, " European Journal of Drug Metabolism and Pharmacokinetics, vol. 28, no. 1, pp. 41-48, 2003
34. X. Cao, S. T. Gibbs, L. Fang et al., "Why is it challenging to predict intestinal drug absorption and oral bioavailability in human using rat model, " Pharmaceutical Research, vol. 23, no. 8, pp. 1675-1686, 2006
35. C. Awortwe, P. S. Fasinu, and B. Rosenkranz, "Application of Caco-2 cell line in herb-drug interaction studies: current approaches and challenges, " Journal of Pharmacy and Pharmaceutical Sciences, vol. 17, no. 1, pp. 1-19, 2014
36. N. Holmstock, F. J. Gonzalez, M. Baes, P. Annaert, and P. Augustijns, "PXR/CYP3A4-humanized mice for studying drugdrug interactions involving intestinal P-glycoprotein, " Molecular Pharmaceutics, vol. 10, no. 3, pp. 1056-1062, 2013
37. K. Schroer, M. Kittelmann, and S. Ltz, "Recombinant human cytochrome P450 monooxygenases for drugmetabolite synthesis, " Biotechnology and Bioengineering, vol. 106, no. 5, pp. 699-706, 2010
38. G. Regev-Shoshani, O. Shoseyov, and Z. Kerem, "Influence of lipophilicity on the interactions of hydroxy stilbenes with cytochrome P450 3A4, " Biochemical and Biophysical Research Communications, vol. 323, no. 2, pp. 668-673, 2004
39. L. Tang, L. Ye, C. Lv, Z. Zheng, Y. Gong, and Z. Liu, "Involvement of CYP3A4/5 and CYP2D6 in themetabolism of aconitine using human liver microsomes and recombinant CYP450 enzymes, " Toxicology Letters, vol. 202, no. 1, pp. 47-54, 2011
40. Y. V. Grinkova, I. G. Denisov, M. A. McLean, and S. G. Sligar, "Oxidase uncoupling in heme monooxygenases: human cytochrome P450 CYP3A4 in Nanodiscs, " Biochemical and Biophysical Research Communications, vol. 430, no. 4, pp. 1223-1227, 2013
41. D. Hamdane, H. Zhang, and P. Hollenberg, "Oxygen activation by cytochrome P450 monooxygenase, " Photosynthesis Research, vol. 98, no. 1-3, pp. 657-666, 2008
42. B. Meunier, S. P. de Visser, and S. Shaik, "Mechanism of oxidation reactions catalyzed by cytochrome P450 enzymes, " Chemical Reviews, vol. 104, no. 9, pp. 3947-3980, 2004
43. P. R. O. deMontellano and J. J. de Voss, "Substrate oxidation by cytochrome P450 enzymes, " in Cytochrome P450, pp. 183-245, Springer, NewYork, NY, USA, 3rd edition, 2005
44. S.-F. Zhou, J.-P. Liu, and B. Chowbay, "Polymorphism of human cytochrome P450 enzymes and its clinical impact, " Drug Metabolism Reviews, vol. 41, no. 2, pp. 89-295, 2009
45. M. H. Choi, P. L. Skipper, J. S. Wishnok, and S. R. Tannenbaum, "Characterization of testosterone 11-hydroxylation catalyzed by human liver microsomal cytochromes P450, " Drug Metabolism and Disposition, vol. 33, no. 6, pp. 714-718, 2005
46. N. Yasui-Furukori, M. Hidestr and , E. Spina, G. Facciol, M. G. Scordo, and G. Tybring, "Different enantioselective 9-hydroxylation of risperidone by the two humanCYP2D6 and CYP3A4 enzymes, " Drug Metabolism & Disposition, vol. 29, no. 10, pp. 1263-1268, 2001
47. Z. Liu and M. Hu, "Natural polyphenol disposition via coupled metabolic pathways, " Expert Opinion on Drug Metabolism and Toxicology, vol. 3, no. 3, pp. 389-406, 2007
48. C. Manach, J. Hubert, R. Llorach, and A. Scalbert, "The complex links between dietary phytochemicals and human health deciphered by metabolomics, " Molecular Nutrition and Food Research, vol. 53, no. 10, pp. 1303-1315, 2009
49. M. P. Corcoran, D. L. McKay, and J. B. Blumberg, "Flavonoid basics: chemistry, sources, mechanisms of action, and safety, " Journal of Nutrition in Gerontology and Geriatrics, vol. 31, no. 3, pp. 176-189, 2012
50. G. F. Ferrazzano, I. Amato, A. Ingenito, A. Zarrelli, G. Pinto, and A. Pollio, "Plant polyphenols and their anti-cariogenic properties: a review, " Molecules, vol. 16, no. 2, pp. 1486-1507, 2011
51. A. Scalbert and G. Williamson, "Dietary intake and bioavailability of polyphenols, " Journal of Nutrition, vol. 130, no. 8, pp. 2073S-2085S, 2000
52. J. D. Lambert, S. Sang, and C. S. Yang, "Biotransformation of green tea polyphenols and the biological activities of those metabolites, " Molecular Pharmaceutics, vol. 4, no. 6, pp. 819-825, 2007
53. J. D. Lambert, S. Sang, and C. S. Yang, "Possible controversy over dietary polyphenols: benefits vs risks, " Chemical Research in Toxicology, vol. 20, no. 4, pp. 583-585, 2007
54. S. Wanwimolruk and V. Prachayasittikul, "Cytochrome P450 enzyme mediated herbal drug interactions (part 1), " EXCLI Journal, vol. 13, pp. 347-391, 2014
55. K. E. Heim, A. R. Tagliaferro, and D. J. Bobilya, "Flavonoid antioxidants: chemistry, metabolism and structure-Activity relationships, " Journal of Nutritional Biochemistry, vol. 13, no. 10, pp. 572-584, 2002
56. I. Rodeiro, M. T. Donato, A. Lahoz, G. Garrido, R. Delgado, and M. J. Gmez-Lechn, "Interactions of polyphenols with the P450 system: possible implications on human therapeutics, " Mini-Reviews in Medicinal Chemistry, vol. 8, no. 2, pp. 97-106, 2008
57. L. M. Blanco-Colio, M. Valderrama, L. A. Alvarez-Sala et al., "Red wine intake prevents nuclear factor-B activation in peripheral blood mononuclear cells of healthy volunteers during postpr and ial lipemia, " Circulation, vol. 102, no. 9, pp. 1020-1026, 2000
58. L. Hooper, P. A. Kroon, E. B. Rimm et al., "Flavonoids, flavonoid-rich foods, and cardiovascular risk: a meta-Analysis of r and omized controlled trials, "The American Journal of Clinical Nutrition, vol. 88, no. 1, pp. 38-50, 2008
59. J. P. E. Spencer, "Flavonoids and brain health: multiple effects underpinned by common mechanisms, " Genes and Nutrition, vol. 4, no. 4, pp. 243-250, 2009
60. Y. J. Surh, "Cancer chemoprevention with dietary phytochemicals, " Nature Reviews Cancer, vol. 3, no. 10, pp. 768-780, 2003
61. L. Rodruez-Fragoso, J. L. Martez-Arismendi, D. Orozco-Bustos, J. Reyes-Esparza, E. Torres, and S. W. Burchiel, "Potential risks resulting from fruit/vegetable-drug interactions: effects on drug-metabolizing enzymes and drug transporters, " Journal of Food Science, vol. 76, no. 4, pp. R112-R124, 2011
62. L. Korkina, C. De Luca, and S. Pastore, "Plant polyphenols and human skin: friends or foes, " Annals of the New York Academy of Sciences, vol. 1259, no. 1, pp. 77-86, 2012
63. Y. D. Muthiah, C. E. Ong, S. A. Sulaiman, S. C. Tan, and R. Ismail, "In-vitro inhibitory effect of Tualang honey on cytochrome P450 2C8 activity, " Journal of Pharmacy and Pharmacology, vol. 64, no. 12, pp. 1761-1769, 2012
64. D. Schwarz, P. Kisselev, W.-H. Schunck, and I. Roots, "Inhibition of 17-estradiol activation by CYP1A1: genotype-And regioselective inhibition by St. John'sWort and several natural polyphenols, " Biochimica et Biophysica Acta-Proteins and Proteomics, vol. 1814, no. 1, pp. 168-174, 2011
65. J. M. Lillywhite, J. E. Simonsen, and V. Wilson, "Growing Chinese medicinal herbs in the United States: underst and ing practitioner preferences, " Agriculture and Human Values, vol. 29, no. 2, pp. 151-159, 2012
66. A. Jain, R. Sharma, N. Gahalain, J. Chaudary, and G. K. Gupta, "Herbal plants used in diabetic complications: an overview, " Journal of Pharmacy Research, vol. 4, no. 4, pp. 986-988, 2011
67. S. Zhou, Y. Gao, W. Jiang, M. Huang, A. Xu, and J. W. Paxton, "Interactions of herbs with cytochrome P450, " DrugMetabolism Reviews, vol. 35, no. 1, pp. 35-98, 2003
68. A. A. Izzo, "Herb-drug interactions: an overview of the clinical evidence, " Fundamental and Clinical Pharmacology, vol. 19, no. 1, pp. 1-16, 2005
69. P. H. Marathe and A. D. Rodrigues, "In vivo animal models for investigating potential CYP3A-And Pgp-mediated drug-drug interactions, " Current Drug Metabolism, vol. 7, no. 7, pp. 687-704, 2006
70. T. L. Poulos, "Cytochrome P450 dynamics, " in Fifty Years of Cytochrome P450 Research, pp. 75-94, Springer, Tokyo, Japan, 2014
71. A. R. Topletz, J. B. Dennison, R. J. Barbuch, C. E. Hadden, S. D. Hall, and J. L. Renbarger, "The relative contributions of CYP3A4 and CYP3A5 to the metabolism of vinorelbine, " Drug Metabolism & Disposition, vol. 41, no. 9, pp. 1651-1661, 2013
72. S. J. Brantley, A. A. Argikar, Y. S. Lin, S. Nagar, and M. F. Paine, "Herb-drug interactions: challenges and opportunities for improved predictions, " Drug Metabolism and Disposition, vol. 42, no. 3, pp. 301-317, 2014
73. Y. Kimura, H. Ito, R. Ohnishi, and T. Hatano, "Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity, " Food and Chemical Toxicology, vol. 48, no. 1, pp. 429-435, 2010
74. I. Rodeiro, M. T. Donato, N. Jimenez et al., "Inhibition of human P450 enzymes by natural extracts used in traditionalmedicine, " Phytotherapy Research, vol. 23, no. 2, pp. 279-282, 2009
75. R. Z. Harris, G. R. Jang, and S. Tsunoda, "Dietary effects on drug metabolism and transport, " Clinical Pharmacokinetics, vol. 42, no. 13, pp. 1071-1088, 2003
76. D. G. Bailey, J. Malcolm, O. Arnold, and J. D. Spence, "Grapefruit juice-drug interactions, " British Journal ofClinical Pharmacology, vol. 46, no. 2, pp. 101-110, 1998
77. Y.-M. Ku, D. I. Min, and M. Flanigan, "Effect of grapefruit juice on the pharmacokinetics of microemulsion cyclosporine and its metabolite in healthy volunteers: does the formulation difference matter?" Journal of Clinical Pharmacology, vol. 38, no. 10, pp. 959-965, 1998
78. D. I. Min, Y.-M. Ku, P. J. Perry et al., "Effect of grapefruit juice on cyclosporine pharmacokinetics in renal transplant patients1, " Transplantation, vol. 62, no. 1, pp. 123-125, 1996
79. J. S. Markowitz, J. L. Donovan, C. L. deVane et al., "Effect of St. John's Wort on drug metabolism by induction of cytochrome P450 3A4 enzyme, " Journal of theAmericanMedical Association, vol. 290, no. 11, pp. 1500-1504, 2003
80. G. W. Barone, B. J. Gurley, B. L. Ketel, M. L. Lightfoot, and S. R. Abul-Ezz, "Drug interaction between St. John's wort and cyclosporine, " Annals of Pharmacotherapy, vol. 34, no. 9, pp. 1013-1016, 2000
81. H.-H. S. Chow, L. L. Garl and , C.-H. Hsu et al., "Resveratrol modulates drug-And carcinogen-metabolizing enzymes in a healthy volunteer study, " Cancer Prevention Research, vol. 3, no. 9, pp. 1168-1175, 2010
82. S. F. Zhou, C. C. Xue, X. Q. Yu, C. Li, and G. Wang, "Clinically important drug interactions potentially involving mechanismbased inhibition of cytochrome P450 3A4 and the role of therapeutic drug monitoring, " Therapeutic Drug Monitoring, vol. 29, no. 6, pp. 687-710, 2007
83. X.-W. Chen, K. B. Sneed, S.-Y. Pan et al., "Herb-drug interactions and mechanistic and clinical considerations, " Current Drug Metabolism, vol. 13, no. 5, pp. 640-651, 2012
84. F. Qiu, J. Jiang, Y. Ma et al., "Opposite effects of single-dose and multidose administration of the ethanol extract of danshen on CYP3A in healthy volunteers, " Evidence-Based Complementary and Alternative Medicine, vol. 2013, Article ID 730734, 8 pages, 2013
85. R. Rahimi and M. Abdollahi, "An update on the ability of St. John's wort to affect the metabolism of other drugs, " Expert Opinion on Drug Metabolism and Toxicology, vol. 8, no. 6, pp. 691-708, 2012
86. H. G. Xie and R. B. Kim, "St. John's wort-Associated drug interactions: Short-term inhibition and long-term induction?" Clinical Pharmacology & Therapeutics, vol. 78, no. 1, pp. 19-24, 2005
87. J. Patel, B. Buddha, S. Dey, D. Pal, and A. K. Mitra, "In vitro interaction of the HIV protease inhibitor ritonavir with herbal constituents: changes in P-gp and CYP3A4 activity, " The American Journal ofTherapeutics, vol. 11, no. 4, pp. 262-277, 2004
88. T. M. Vijayakumar, R. M. Kumar, A. Agrawal, G. P. Dubey, and K. Ilango, "Comparative inhibitory potential of selected dietary bioactive polyphenols, phytosterols on CYP3A4 and CYP2D6 with fluorometric high-throughput screening, " Journal of Food Science and Technology, 2014
89. S. J. Brantley, T. N. Graf, N. H. Oberlies, and M. F. Paine, "A systematic approach to evaluate herb-drug interaction mechanisms: investigation of milk thistle extracts and eight isolated constituents as CYP3A inhibitors, " Drug Metabolism and Disposition, vol. 41, no. 9, pp. 1662-1670, 2013
90. I. Rodeiro, M. J. Gmez-Lechn, G. Perez et al., "Mangifera indica L. extract and mangiferin modulate cytochrome P450 and UDP-glucuronosyltransferase enzymes in primary cultures of human hepatocytes, " Phytotherapy Research, vol. 27, no. 5, pp. 745-752, 2013
91. J. I. Boullata, "Drug and nutrition interactions: not just food for thought, " Journal of Clinical Pharmacy and Therapeutics, vol. 38, no. 4, pp. 269-271, 2013
92. O.A. Fahmi, T. S. Maurer, M. Kish, E. Cardenas, S. Boldt, and D. Nettleton, "A combined model for predicting CYP3A4 clinical net drug-drug interaction based on CYP3a4 inhibition, inactivation, and induction determined in vitro, " Drug Metabolism and Disposition, vol. 36, no. 8, pp. 1698-1708, 2008
93. Y.-H. Wang, D. R. Jones, and S. D. Hall, "Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites, "DrugMetabolism and Disposition, vol. 32, no. 2, pp. 259-266, 2004
94. J. A. Ross and C.M. Kasum, "Dietary flavonoids: bioavailability, metabolic effects, and safety, " Annual Review of Nutrition, vol. 22, pp. 19-34, 2002
95. A. Scalbert, I. T. Johnson, and M. Saltmarsh, "Polyphenols: antioxidants and beyond, " The American Journal of Clinical Nutrition, vol. 81, no. 1, pp. 215S-217S, 2005
96. P. Chabert, C. Auger, J. Pincemail, and V. B. Schini-Kerth, "Overview of plant-derived antioxidants, " in Systems Biology of Free Radicals and Antioxidants, pp.4005-4022, Springer, Berlin, Germany, 2014
97. J. Prez-Jimnez, M. E. Diz-Rubio, and F. Saura-Calixto, "Nonextractable polyphenols, a major dietary antioxidant: occurrence, metabolic fate and health effects, " Nutrition Research Reviews, vol. 26, no. 2, pp. 118-129, 2013
98. M.-L. Ovaskainen, R. Trrnen, J. M. Koponen et al., "Dietary intake and major food sources of polyphenols in Finnish adults, " Journal of Nutrition, vol. 138, no. 3, pp. 562-566, 2008
99. N.N. Thu, C. Sakurai, H. Uto et al., "Thepolyphenol content and antioxidant activities of the main edible vegetables in Northern Vietnam, " Journal of Nutritional Science and Vitaminology, vol. 50, no. 3, pp. 203-210, 2004
100. F. Saura-Calixto, J. Serrano, and I. Gõni, "Intake and bioaccessibility of total polyphenols in a whole diet, " Food Chemistry, vol. 101, no. 2, pp. 492-501, 2007
101. J. Kanner and T. Lapidot, "The stomach as a bioreactor: dietary lipid peroxidation in the gastric fluid and the effects of plantderived antioxidants, " Free Radical Biology & Medicine, vol. 31, no. 11, pp. 1388-1395, 2001
102. Z. Kerem, D. Chetrit, O. Shoseyov, and G. Regev-Shoshani, "Protection of lipids from oxidation by epicatechin, transresveratrol, and gallic and caffeic acids in intestinal model systems, " Journal of Agricultural and Food Chemistry, vol. 54, no. 26, pp. 10288-10293, 2006
103. C. J. Dufresne and E. R. Farnworth, "A review of latest research findings on the health promotion properties of tea, " Journal of Nutritional Biochemistry, vol. 12, no. 7, pp. 404-421, 2001
104. F. Shahidi and Y. Zhong, "Novel antioxidants in food quality preservation and health promotion, " European Journal of Lipid Science and Technology, vol. 112, no. 9, pp. 930-940, 2010
105. N. Khan and H. Mukhtar, "Cancer and metastasis: prevention and treatment by green tea, " Cancer and Metastasis Reviews, vol. 29, no. 3, pp. 435-445, 2010
106. B. B. Aggarwal and S. Shishodia, "Molecular targets of dietary agents for prevention and therapy of cancer, " Biochemical Pharmacology, vol. 71, no. 10, pp. 1397-1421, 2006
107. G. Garrido, D. Gonzlez, Y. Lemus et al., "In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG), " Pharmacological Research, vol. 50, no. 2, pp. 143-149, 2004
108. S. N. Nichenametla, T.G. Taruscio, D. L. Barney, and J. H. Exon, "A review of the effects and mechanisms of polyphenolics in cancer, " Critical Reviews in Food Science and Nutrition, vol. 46, no. 2, pp. 161-183, 2006
109. N. T. Zaveri, "Green tea and its polyphenolic catechins: medicinal uses in cancer and noncancer applications, " Life Sciences, vol. 78, no. 18, pp. 2073-2080, 2006
110. N. Kalogeropoulos, K. Yannakopoulou, A. Gioxari, A. Chiou, and D. P. Makris, "Polyphenol characterization and encapsulation in-cyclodextrin of a flavonoid-rich Hypericum perforatum (St John's wort) extract, " LWT-Food Science and Technology, vol. 43, no. 6, pp. 882-889, 2010
111. H. J. Lee, H.-S. Lee, H. J. Cho, S. Y. Kim, and H. J. Suh, "Utilization of hydrolytic enzymes for the extraction of ginsenosides from Korean ginseng leaves, " Process Biochemistry, vol. 47, no. 3, pp. 538-543, 2012
112. M. Maizura, A. Aminah, and W. M. W. Aida, "Total phenolic content and antioxidant activity of kesum (Polygonum minus), ginger (Zingiber officinale) and turmeric (Curcuma longa) extract, " International Food Research Journal, vol. 18, no. 2, pp. 529-534, 2011
113. B. Jiang, F. Kronenberg, M. J. Balick, and E. J. Kennelly, "Stability of black cohosh triterpene glycosides and polyphenols: potential clinical relevance, " Phytomedicine, vol. 20, no. 6, pp. 564-569, 2013
114. S. S. Georgieva, V. L. Christova-Bagdassarian, and M. S. Atanassova, "Comparative evaluation of the polyphenol composition and antioxidant capacity of propolis and Echinacea purpurea, " Journal of Experimental and IntegrativeMedicine, vol. 4, no. 1, pp. 51-56, 2014
115. F. F. Anhe, D. Roy, G. Pilon et al., "A polyphenol-rich cranberry extract protects from diet-induced obesity, insulin resistance and intestinal inflammation in association with increased Akkermansia spp. population in the gut microbiota of mice, " Gut, 2014
116. A. R. Rechner, G. Kuhnle, P. Bremner, G. P. Hubbard, K. P. Moore, and C. A. Rice-Evans, "The metabolic fate of dietary polyphenols in humans, " Free Radical Biology and Medicine, vol. 33, no. 2, pp. 220-235, 2002
117. L. Bravo, "Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance, " Nutrition Reviews, vol. 56, no. 11, pp. 317-333, 1998
118. H. Doostdar, M. D. Burke, and R. T. Mayer, "Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1, " Toxicology, vol. 144, no. 1-3, pp. 31-38, 2000
119. C. Rice-Evans, "Flavonoid antioxidants, " Current Medicinal Chemistry, vol. 8, no. 7, pp. 797-807, 2001
120. P. Jancov, E. Anzenbacherov, B. Papouskov et al., "Silybin is metabolized by cytochrome P450 2C8 in vitro, " Drug Metabolism & Disposition, vol. 35, no. 11, pp. 2035-2039, 2007
121. C. S. Yang and E. Pan, "The effects of green tea polyphenols on drug metabolism, " Expert Opinion on Drug Metabolism and Toxicology, vol. 8, no. 6, pp. 677-689, 2012
122. S. Sang, J. D. Lambert, C.-T. Ho, and C. S. Yang, "The chemistry and biotransformation of tea constituents, " Pharmacological Research, vol. 64, no. 2, pp. 87-99, 2011
123. R. Didziapetris, J. Dapkunas, A. Sazonovas, and P. Japertas, "Trainable structure-Activity relationship model for virtual screening of CYP3A4 inhibition, " Journal of Computer-Aided Molecular Design, vol. 24, no. 11, pp. 891-906, 2010
124. K. Roy and P. P. Roy, "QSAR of cytochrome inhibitors, " Expert Opinion on Drug Metabolism and Toxicology, vol. 5, no. 10, pp. 1245-1266, 2009
125. S. Misaka, K. Kawabe, S. Onoue et al., "Green tea extract affects the cytochrome P450 3A activity and pharmacokinetics of simvastatin in rats, " Drug Metabolism and Pharmacokinetics, vol. 28, no. 6, pp. 514-518, 2013
126. M. Nishikawa, N. Ariyoshi, A. Kotani et al., "Effects of continuous ingestion of green tea or grape seed extracts on the pharmacokinetics of midazolam, " Drug Metabolism and Pharmacokinetics, vol. 19, no. 4, pp. 280-289, 2004
127. A. Amri, J. C. Chaumeil, S. Sfar, and C. Charrueau, "Administration of resveratrol: what formulation solutions to bioavailability limitations?" Journal of Controlled Release, vol. 158, no. 2, pp. 182-193, 2012
128. T. Walle, "Bioavailability of resveratrol, " Annals of the New York Academy of Sciences, vol. 1215, no. 1, pp. 9-15, 2011
129. J.-F. Marier, P. Vachon, A. Gritsas, J. Zhang, J.-P. Moreau, and M. P. Ducharme, "Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model, " Journal of Pharmacology and ExperimentalTherapeutics, vol. 302, no. 1, pp. 369-373, 2002
130. G. Singh and R. S. Pai, "In-vitro/in-vivo characterization of trans-resveratrol-loaded nanoparticulate drug delivery system for oral administration, " Journal of Pharmacy and Pharmacology, vol. 66, no. 8, pp. 1062-1076, 2014
131. K. B. Seljak, K. Berginc, J. Trontelj, A. Zvonar, A. Kristl, and M. Gasperlin, "A self-microemulsifying drug delivery system to overcome intestinal resveratrol toxicity and presystemic metabolism, " Journal of Pharmaceutical Sciences, vol. 103, no. 11, pp. 3491-3500, 2014
132. S.G. Parkar, T. M. Trower, and D. E. Stevenson, "Fecalmicrobial metabolism of polyphenols and its effects on human gut microbiota, " Anaerobe, vol. 23, pp. 12-19, 2013
133. S. G. Parkar, D. E. Stevenson, and M. A. Skinner, "The potential influence of fruit polyphenols on colonic microflora and human gut health, " International Journal of FoodMicrobiology, vol. 124, no. 3, pp. 295-298, 2008
134. S. Bolca, T. van deWiele, and S. Possemiers, "Gut metabotypes govern health effects of dietary polyphenols, " Current Opinion in Biotechnology, vol. 24, no. 2, pp. 220-225, 2013
135. C. Mor and , C. Dubray, D. Milenkovic et al., "Hesperidin contributes to the vascular protective effects of orange juice: a r and omized crossover study in healthy volunteers, " The American Journal of Clinical Nutrition, vol. 93, no. 1, pp. 73-80, 2011
136. J. W. Lampe, "Interindividual differences in response to plantbased diets: implications for cancer risk, " The American Journal of Clinical Nutrition, vol. 89, no. 5, pp. 1553S-1557S, 2009
137. S. Stoupi, G. Williamson, J. W. Drynan, D. Barron, and M. N. Clifford, "A comparison of the in vitro biotransformation of (-)-epicatechin and procyanidin B2 by human faecal microbiota, " Molecular Nutrition and Food Research, vol. 54, no. 6, pp. 747-759, 2010
138. G. K. Dresser, J. D. Spence, and D. G. Bailey, "Pharmacokineticpharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition, " Clinical Pharmacokinetics, vol. 38, no. 1, pp. 41-57, 2000
139. S. Muto, K.-I. Fujita, Y. Yamazaki, and T. Kamataki, "Inhibition by green tea catechins of metabolic activation of procarcinogens by human cytochrome P450, " Mutation Research-Fundamental and Molecular Mechanisms of Mutagenesis, vol. 479, no. 1-2, pp. 197-206, 2001
140. C. R. Wolf, "Chemoprevention: increased potential to bear fruit, " Proceedings of the National Academy of Sciences of the United States of America, vol. 98, no. 6, pp. 2941-2943, 2001
141. S. Parys, S. Kehraus, A. Krick et al., "In vitro chemopreventive potential of fucophlorethols from the brown alga Fucus vesiculosus L. by anti-oxidant activity and inhibition of selected cytochrome P450 enzymes, " Phytochemistry, vol. 71, no. 2-3, pp. 221-229, 2010
142. M. Athar, J. H. Back, X. Tang et al., "Resveratrol: a review of preclinical studies for human cancer prevention, " Toxicology and Applied Pharmacology, vol. 224, no. 3, pp. 274-283, 2007
143. K. Sahu, A. A. Siddiqui, M. Shaharyar, and S. Malik, "Pharmacokinetic interaction between febuxostat and morin in rats, " ExpertOpinion on Drug Metabolism and Toxicology, vol. 10, no. 3, pp. 307-312, 2014
144. K. K. Kumar, L. Priyanka, K. Gnananath, P. R. Babu, and S. Sujatha, "Pharmacokinetic drug interactions between apigenin, rutin and paclitaxel mediated by P-glycoprotein in rats, " European Journal of Drug Metabolism and Pharmacokinetics, 2014
145. A. Ferreira, S. Pousinho, A. Fortuna, A. Falcao, and G. Alves, "Flavonoidcompounds as reversal agents of theP-glycoproteinmediatedmultidrug resistance: biology, chemistry and pharmacology, " Phytochemistry Reviews, 2014
146. B. T. Gufford, G. Chen, P. Lazarus, T. N. Graf, N. H. Oberlies, and M. F. Paine, "Identification of diet-derived constituents as potent inhibitors of intestinal glucuronidation, " Drug Metabolism & Disposition, vol. 42, no. 10, pp. 1675-1683, 2014
147. X. F. Koe, T. S. T. Muhammad, A. S. C. Chong, H. AbdulWahab, and M. L. Tan, "Cytochrome P450 induction properties of food and herbal-derived compounds using a novel multiplex RTqPCR in vitro assay, a drug-food interaction prediction tool, " Food Science & Nutrition, vol. 2, no. 5, pp. 500-520, 2014
148. T. Shimada, K. Tanaka, S. Takenaka et al., "Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives, " Chemical Research in Toxicology, vol. 23, no. 12, pp. 1921-1935, 2010
149. M. A. Sarkar, G. Scambia, F. O. Ranelletti et al., "Quercetin not only inhibits P-glycoprotein efflux activity but also inhibits CYP3A isozymes, " Cancer Chemotherapy and Pharmacology, vol. 36, no. 5, pp. 448-449, 1995
150. J.-S. Choi, Y.-J. Piao, and K. W. Kang, "Effects of quercetin on the bioavailability of doxorubicin in rats: role of CYP3A4 and P-gp inhibition by quercetin, " Archives of Pharmacal Research, vol. 34, no. 4, pp. 607-613, 2011
151. C.-P. Yu, P.-P. Wu, Y.-C. Hou et al., "Quercetin and rutin reduced the bioavailability of cyclosporine from Neoral, an immunosuppressant, through activating P-glycoprotein and CYP 3A4, " Journal of Agricultural and Food Chemistry, vol. 59, no. 9, pp. 4644-4648, 2011
152. J. Rashid, C. McKinstry, A. G. Renwick, M. Dirnhuber, D. G. Waller, and C. F. George, "Quercetin, an in vitro inhibitor of CYP3A, does not contribute to the interaction between nifedipine and grapefruit juice, " British Journal of Clinical Pharmacology, vol. 36, no. 5, pp. 460-463, 1993
153. J. L. Raucy, "Regulation of CYP3A4 expression in human hepatocytes by pharmaceuticals and natural products, " Drug Metabolism and Disposition, vol. 31, no. 5, pp. 533-539, 2003
154. W. C. Lau, T. D. Welch, T. Shields, M. Rubenfire, U. S. Tantry, and P. A. Gurbel, "The effect of St John'sWort on the pharmacodynamic response of clopidogrel in hyporesponsive volunteers and patients: increased platelet inhibition by enhancement of CYP3A4 metabolic activity, " Journal of Cardiovascular Pharmacology, vol. 57, no. 1, pp. 86-93, 2011
155. A. Kamel and S. Harriman, "Inhibition of cytochrome P450 enzymes and biochemical aspects of mechanism-based inactivation (MBI), " Drug Discovery Today: Technologies, vol. 10, no. 1, pp. e177-e189, 2013
156. L. Quintieri, P. Palatini, A. Nassi, P. Ruzza, and M. Floreani, "Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes, " Biochemical Pharmacology, vol. 75, no. 6, pp. 1426-1437, 2008
157. E. V. Sineva, J. A. O. Rumfeldt, J. R. Halpert, and D. R. Davydov, "A large-scale allosteric transition in cytochrome P450 3A4 revealed by luminescence resonance energy transfer (LRET), " PLoS ONE, vol. 8, no. 12, Article IDe83898, 2013
158. D. R. Davydov, N. Y. Davydova, E. V. Sineva, I. Kufareva, and J. R. Halpert, "Pivotal role of P450-P450 interactions in CYP3A4 allostery: the case of-naphthoflavone, " Biochemical Journal, vol. 453, no. 2, pp. 219-230, 2013
159. D. R. Davydov, J. A. O. Rumfeldt, E. V. Sineva, H. Fern and o, N. Y. Davydova, and J. R. Halpert, "Peripheral lig and-binding site in cytochrome P450 3A4 located with fluorescence resonance energy transfer (FRET), " Journal of Biological Chemistry, vol. 287, no. 9, pp. 6797-6809, 2012
160. D. J. Frank, I. G. Denisov, and S. G. Sligar, "Analysis of heterotropic cooperativity in cytochrome P450 3A4 using-naphthoflavone and testosterone, " Journal of Biological Chemistry, vol. 286, no. 7, pp. 5540-5545, 2011
161. A. G. Roberts and W. M. Atkins, "Energetics of heterotropic cooperativity between-naphthoflavone and testosterone binding to CYP3A4, " Archives of Biochemistry and Biophysics, vol. 463, no. 1, pp. 89-101, 2007
162. M. I. Netsch, H. Gutmann, C. B. Schmidlin, C. Aydogan, and J. Drewe, "Induction of CYP1A by green tea extract in human intestinal cell lines, " Planta Medica, vol. 72, no. 6, pp. 514-520, 2006
163. D. G. Bailey, J.M.O. Arnold, and J. D. Spence, "Grapefruit juice and drugs. Howsignificant is the interaction?" Clinical Pharmacokinetics, vol. 26, no. 2, pp. 91-98, 1994
164. U. Fuhr and A. L. Kummert, "The fata of naringin in humans: a key to grapefruit juice-drug interactions?" Clinical Pharmacology and Therapeutics, vol. 58, no. 4, pp. 365-373, 1995
165. P.-C. Ho, D. J. Saville, and S. Wanwimolruk, "Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds, " Journal of Pharmacy & Pharmaceutical Sciences, vol. 4, no. 3, pp. 217-227, 2001
166. K. Iwanaga, M. Hayashi, Y. Hamahata et al., "Furanocoumarin derivatives in Kampo extract medicines inhibit cytochrome P450 3A4 and P-glycoprotein, " Drug Metabolism and Disposition, vol. 38, no. 8, pp. 1286-1294, 2010
167. K. M. V and erMolen, G. R. Ainslie, M. F. Paine, and N. H. Oberlies, "Labeled content of two furanocoumarins in dietary supplements correlates with neither actual content nor CYP3A inhibitory activity, " Journal of Pharmaceutical and Biomedical Analysis, vol. 98, pp. 260-265, 2014
168. Y.-F. Ueng, C.-C. Chen, H. Yamazaki et al., "Mechanism-based inhibition of CYP1A1 and CYP3A4 by the furanocoumarin chalepensin, " Drug Metabolism and Pharmacokinetics, vol. 28, no. 3, pp. 229-238, 2013
169. B. C. Foster, S. V and enhoek, J. Hana et al., "In vitro inhibition of human cytochrome P450-mediated metabolism of marker substrates by natural products, " Phytomedicine, vol. 10, no. 4, pp. 334-342, 2003
170. E. S. Roberts-Kirchhoff, J. R. Crowley, P. F. Hollenberg, and H. Kim, "Metabolism of genistein by rat and human cytochrome P450s, " Chemical Research in Toxicology, vol. 12, no. 7, pp. 610-616, 1999
171. L. M. Scott, P. Durant, S. Leone-Kabler et al., "Effects of prior oral contraceptive use and soy isoflavonoids on estrogenmetabolizing cytochrome P450 enzymes, " Journal of Steroid Biochemistry and Molecular Biology, vol. 112, no. 4-5, pp. 179-185, 2008
172. C.-Q. Xiao, R. Chen, J. Lin et al., "Effect of genistein on the activities of cytochrome P450 3A and P-glycoprotein inChinese healthy participants, " Xenobiotica, vol. 42, no. 2, pp. 173-178, 2012
173. Y. Chen, C.-Q. Xiao, Y.-J. He et al., "Genistein alters caffeine exposure in healthy female volunteers, " European Journal of Clinical Pharmacology, vol. 67, no. 4, pp. 347-353, 2011
174. A. Dreiseitel, P. Schreier, A. Oehme, S. Locher, G. Hajak, and P. G. S and , "Anthocyanins and their metabolites are weak inhibitors of cytochrome P450 3A4, " Molecular Nutrition and Food Research, vol. 52, no. 12, pp. 1428-1433, 2008
175. W. K. Chan and A. B. Delucchi, "Resveratrol, a red wine constituent, is a mechanism-based inactivator of cytochrome P450 3A4, " Life Sciences, vol. 67, no. 25, pp. 3103-3112, 2000
176. B. Piver, F. Berthou, Y. Dreano, and D. Lucas, "Inhibition of CYP3A, CYP1A and CYP2E1 activities by resveratrol and other non volatile red wine components, " Toxicology Letters, vol. 125, no. 1-3, pp. 83-91, 2001
177. S.-P. Hong, D.-H. Choi, and J.-S. Choi, "Effects of resveratrol on the pharmacokinetics of diltiazem and its major metabolite, desacetyldiltiazem, in rats, " Cardiovascular Therapeutics, vol. 26, no. 4, pp. 269-275, 2008
178. Y. C. Chi, S. P. Lin, and Y. C. Hou, "Anewherb-drug interaction of Polygonum cuspidatum, a resveratrol-rich nutraceutical, with carbamazepine in rats, " Toxicology and Applied Pharmacology, vol. 263, no. 3, pp. 315-322, 2012
179. P. Detampel, M. Beck, S. Krhenbhl, and J. Huwyler, "Drug interaction potential of resveratrol, " Drug Metabolism Reviews, vol. 44, no. 3, pp. 253-265, 2012
180. M. A. Correia and P. R. O. de Montellano, "Inhibition of cytochrome P450 enzymes, " in Cytochrome P450, pp. 247-322, Springer, Berlin, Germany, 3rd edition, 2005
181. Y. Sahali-Sahly, S. K. Balani, J. H. Lin, and T. A. Baillie, "In vitro studies on the metabolic activation of the furanopyridine L-754, 394, a highly potent and selective mechanism-based inhibitor of cytochrome P450 3A4, " Chemical Research in Toxicology, vol. 9, no. 6, pp. 1007-1012, 1996
182. H. Iwata, Y. Tezuka, S. Kadota, A. Hiratsuka, and T. Watabe, "Identification and characterization of potent CYP3A4 inhibitors in Schis and ra fruit extract, " Drug Metabolism and Disposition, vol. 32, no. 12, pp. 1351-1358, 2004
183. R. Venkataramanan, V. Ramach and ran, B. J. Komoroski, S. Zhang, P. L. Schiff, and S. C. Strom, "Milk thistle, a herbal supplement, decreases the activity of CYP3A4 and uridine diphosphoglucuronosyl transferase in human hepatocyte cultures, " Drug Metabolism and Disposition, vol. 28, no. 11, pp. 1270-1273, 2000
184. R. Zuber, M. Modriansk, Z. Dvork et al., "Effect of silybin and its congeners on human liver microsomal cytochrome P450 activities, " Phytotherapy Research, vol. 16, no. 7, pp. 632-638, 2002
185. H.-T. Yao, Y.-W. Chang, S.-J. Lan, and T.-K. Yeh, "The inhibitory effect of tannic acid on cytochrome P450 enzymes and NADPH-CYP reductase in rat and human liver microsomes, " Food and Chemical Toxicology, vol. 46, no. 2, pp. 645-653, 2008
186. C. Jaikang, K. Niwatananun, P. Narongchai, S. Narongchai, and C. Chaiyasut, "Inhibitory effect of caffeic acid and its derivatives on human liver cytochrome P450 3A4 activity, " Journal of Medicinal Plants Research, vol. 5, no. 15, pp. 3530-3536, 2011
187. I. Stupans, G. Stretch, and P. Hayball, "Olive oil phenols inhibit human hepatic microsomal activity, " Journal of Nutrition, vol. 130, no. 9, pp. 2367-2370, 2000
188. I. Stupans, H.-W. Tan, A. Kirlich, K. Tuck, P. Hayball, and M. Murray, "Inhibition of CYP3A-mediated oxidation in human hepatic microsomes by the dietary derived complex phenol, gallic acid, " Journal of Pharmacy and Pharmacology, vol. 54, no. 2, pp. 269-275, 2002
189. J. K. Yano, M. R. Wester, G. A. Schoch, K. J. Griffin, C. D. Stout, and E. F. Johnson, "The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05-A resolution, "The Journal of Biological Chemistry, vol. 279, no. 37, pp. 38091-38094, 2004
190. P. A. Williams, J. Cosme, D. M. Vinkovi et al., "Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone, " Science, vol. 305, no. 5684, pp. 683-686, 2004
191. J. Sridhar, J. Liu, M. Foroozesh, and C. L. K. Stevens, "Insights on cytochrome P450 enzymes and inhibitors obtained through QSAR studies, " Molecules, vol. 17, no. 8, pp. 9283-9305, 2012
192. D. F. V. Lewis and B. G. Lake, "Molecularmodelling and quantitative structure-Activity relationship studies on the interaction of omeprazole with cytochrome P450 isozymes, " Toxicology, vol. 125, no. 1, pp. 31-44, 1998
193. S. Ekins, G. Bravi, J. H. Wikel, and S. A. Wrighton, "Threedimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates, " Journal of Pharmacology and Experimental Therapeutics, vol. 291, no. 1, pp. 424-433, 1999
194. S. Ekins, M. J. de Groot, and J. P. Jones, "Pharmacophore and three-dimensional quantitative structure activity relationship methods for modeling cytochrome p450 active sites, " Drug Metabolism and Disposition, vol. 29, no. 7, pp. 936-944, 2001
195. A. Galetin, S. E. Clarke, and J. B. Houston, "Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: midazolam, testosterone, and nifedipine, " Drug Metabolism and Disposition, vol. 31, no. 9, pp. 1108-1116, 2003
196. K. Ohkura, Y. Kawaguchi, Y. Watanabe, Y. Masubuchi, Y. Shinohara, and H. Hori, "Flexible structure of cytochrome P450: promiscuity of lig and binding in the CYP3A4 heme pocket, " Anticancer Research, vol. 29, no. 3, pp. 935-942, 2009
197. K. E. Kenworthy, S. E. Clarke, J. Andrews, and J. B. Houston, "Multisite kinetic models for CYP3A4: simultaneous activation and inhibition of diazepam and testosteronemetabolism, " Drug Metabolism and Disposition, vol. 29, no. 12, pp. 1644-1651, 2001
198. M. Ekroos and T. Sjgren, "Structural basis for lig and promiscuity in cytochrome P450 3A4, " Proceedings of the National Academy of Sciences of the United States of America, vol. 103, no. 37, pp. 13682-13687, 2006
199. I. G. Denisov, D. J. Frank, and S. G. Sligar, "Cooperative properties of cytochromes P450, " Pharmacology & Therapeutics, vol. 124, no. 2, pp. 151-167, 2009
200. W. M. Atkins, "Non-Michaelis-Menten kinetics in cytochrome P450-catalyzed reactions, " Annual Review of Pharmacology and Toxicology, vol. 45, pp. 291-310, 2005
201. J. M. Hutzler and T. S. Tracy, "Atypical kinetic profiles in drug metabolism reactions, " Drug Metabolism and Disposition, vol. 30, no. 4, pp. 355-362, 2002
202. D. R. Davydov and J. R. Halpert, "Allosteric P450 mechanisms: multiple binding sites, multiple conformers of both?" Expert Opinion on Drug Metabolism and Toxicology, vol. 4, no. 12, pp. 1523-1535, 2008
203. I. G. Denisov and S. G. Sligar, "Anovel type of allosteric regulation: functional cooperativity in monomeric proteins, " Archives of Biochemistry and Biophysics, vol. 519, no. 2, pp. 91-102, 2012
204. D. F. Lewis, B. G. Lake, and M. Dickins, "Quantitative structure-Activity relationships (QSARs) in inhibitors of various cytochromes P450: the importance of compound lipophilicity, " Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 22, no. 1, pp. 1-6, 2007
205. D. F. V. Lewis, B. G. Lake, and M. Dickins, "Quantitative structure-Activity relationships (QSARs) in CYP3A4 inhibitors: the importance of lipophilic character and hydrogen bonding, " Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 21, no. 2, pp. 127-132, 2006
206. B. Mao, R. Gozalbes, F. Barbosa et al., "QSAR modeling of in vitro inhibition of cytochrome P450 3A4, " Journal of Chemical Information and Modeling, vol. 46, no. 5, pp. 2125-2134, 2006
207. P. Matouskov, H. Brtov, I. Bousov et al., "Effect of defined green tea extract in various dosage schemes on drugmetabolizing enzymes in mice in vivo, " Journal of Functional Foods, vol. 10, pp. 327-335, 2014
208. U. F. Ezuruike and J. M. Prieto, "The use of plants in the traditional management of diabetes inNigeria: pharmacological and toxicological considerations, " Journal of Ethnopharmacology, vol. 155, no. 2, pp. 857-924, 2014
209. C. Bunchorntavakul and K. R. Reddy, "Review article: herbal and dietary supplement hepatotoxicity, " Alimentary Pharmacology and Therapeutics, vol. 37, no. 1, pp. 3-17, 2013
210. E. J. Y. Kim, Y. Chen, J. Q. Huang et al., "Evidence-based toxicity evaluation and scheduling of Chinese herbal medicines, " Journal of Ethnopharmacology, vol. 146, no. 1, pp. 40-61, 2013
211. V. S. Neergheen-Bhujun, "Underestimating the toxicological challenges associated with the use of herbal medicinal products in developing countries, " BioMed Research International, vol. 2013, Article ID804086, 9 pages, 2013