Cancer phytotherapeutics: Role for flavonoids at the cellular level

Phytotherapy Research

Volumn 22, Issue 5, 2008, Pages 567-577

  Kale, Anup ^a   Gawande, Sonia ^a   Kotwal, Swati ^a  

^a RTM NAGPUR UNIVERSITY   (India)

Author keywords

CYP; Drugs; Flavonoids; P gp; Phytotherapy; Synergy

Indexed keywords

ANTHOCYANIDIN; CYTOCHROME P450; FLAVANOL DERIVATIVE; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; ISOFLAVONOID;

BIOSYNTHESIS; BIOTRANSFORMATION; CANCER CONTROL; CANCER EPIDEMIOLOGY; CANCER THERAPY; CARCINOGENESIS; CELL PROLIFERATION; CHEMICAL CARCINOGENESIS; CHEMICAL STRUCTURE; CHEMOPROPHYLAXIS; COLON FLORA; DRUG BINDING SITE; DRUG INHIBITION; DRUG METABOLISM; HUMAN; IMMUNE RESPONSE; PHENOTYPE; REVIEW;

ANIMALS; APOPTOSIS; CELL PROLIFERATION; CYTOCHROME P-450 ENZYME SYSTEM; FLAVONOIDS; HUMANS; MODELS, BIOLOGICAL; NEOPLASMS; PHYTOTHERAPY;

EID: 44149088311     PISSN: 0951418X     EISSN: 10991573     Source Type: Journal    
DOI: 10.1002/ptr.2283     Document Type: Review

References (129)

1. Afanas'ev IB, Dorozhko AI, Brodskii AV, Kostyuk VA, Potapovitch AI. 1989. Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation. Biochem Pharmacol 38: 1763-1769.
2. Ahmad N, Feyes DK, Nieminen A-L et al. 1997. Green tea constituent epigallocatechin-3-gallate and induction of apoptosis and cell cycle arrest in human carcinoma cells. J Natl Cancer Inst 89: 1881-1886.
3. Backman JT, Maenpaa J, Belle DJ, Wrighton SA, Kivisto KT, Neuvonen PJ. 2000. Lack of correlation between in vitro and in vivo studies on the effects of tangeretin and tangerine juice on midazolam hydroxylation. Clin Pharmacol Ther 67: 382-390.
4. Bailey DG, Dresser GR, Kreeft JH, Munoz C, Freeman DJ, Bend JR. 2000. Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients. Clin Pharmacol Ther 68: 468-477.
5. Barnes J, Anderson LA, Phillipson JD. 2001. St John's wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties. J Pharm Pharmacol 53: 583-600.
6. Block G, Atterson B, Subar A. 1992. Fruit, vegetables, and cancer prevention: a review of the epidemiological evidence. Nutr Cancer 18: 1-29.
7. Bors W, Heller W, Michel C, Saran M. 1990. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods Enzymol 186: 343-355.
8. Boyle SP, Dobson VL, Duthie SJ, Kyle JAM, Collins AR. 2000. Absorption and DNA protective effects of flavonoid glycosides from an onion meal. Eur J Nutr 39: 213-223.
9. Bracke ME, Depypere HT, Boterberg T et al. 1999. Influence of tangeretin on tamoxifen's therapeutic benefit in mammary cancer. J Natl Cancer Ins 91: 354-359.
10. Bravo L. 1998. Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance. Nutr Rev 56: 317-338.
11. Brown J, Byers T, Thompson K, Eldridge B, Doyle C, Williams AM. 2001. Nutrition during and after cancer treatment: a guide for informed choices by cancer survivors. CA Cancer J Clin 51: 153-181.
12. Canivenc-Lavier MC, Vernevaut MF, Totis M, Siess MH, Magdalou J, Suschetet M. 1996. Comparative effects of flavonoids and model inducers on drug-metabolizing enzymes in rat liver. Toxicology 114: 19-27.
13. Cao G, Sofic E, Prior RL. 1997. Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic Biol Med 22: 749-760.
14. Chan MM, Mattiacci JA, Hwang HS, Shah A, Fong D. 2000. Synergy between ethanol and grape polyphenols, quercetin, and resveratrol, in the inhibition of the inducible nitric oxide synthase pathway. Biochem Pharmacol 60: 1539-1548.
15. Chan WK, Nguyen LT, Miller VP, Harris RZ. 1998. Mechanism-based inactivation of human cytochrome P450 3A4 by grapefruit juice and red wine. Life Sci 62: 135-142.
16. Chen HY, Wu TS, Su SF, Kuo SC, Chao PDL. 2002. Marked decrease of cyclosporin absorption caused by phellamurin in rats. Planta Med 68: 138-141.
17. Chieli E, Romiti N, Cervelli F, Tongiani R. 1995. Effects of flavonols on P-glycoprotein activity in cultured rat hepatocytes. Life Sci 57: 1741-1751.
18. Choi JA, Kim JY, Lee JY et al. 2001. Induction of cell cycle arrest and apoptosis in human breast cancer cells by quercetin. Int J Oncol 19: 837-844.
19. Ciolino HP, Daschner PJ, Yeh GC. 1999. Dietary flavonols quercetin and kaempferol are ligands of aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem J 340: 715-722.
20. Ciolino HP, Wang TTY, Yeh GC. 1998. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Cancer Res 58: 2754-2760.
21. Clemetson CAB. 1989. Bioflavonoids. In Vitamin C, Clemetson CAB (ed). CRC Press: Boca Raton, FL, 101-128.
22. Clemetson CAB, Anderson L. 1966. Plant polyphenols as antioxidants for ascorbic acid. Ann NY Acad Sci 136: 341-376.
23. Constantinou A, Mehta R, Runyan C, Rao K, Vaughan A, Moon R. 1995. Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships. J Nat Prod 58: 217-225.
24. Critchfield JW, Welsh CJ, Phang JM, Yeh GC. 1994. Modulation of adriamycin accumulation and efflux by flavonoids in HCT-15 colon cells. Biochem Pharmacol 48: 1437-1445.
25. Cummins CL, Salphati L, Reid MJ, Benet LZ. 2003. In vivo modulation of intestinal CYP3A metabolism by P-glycoprotein: Studies using the rat single-pass intestinal perfusion model. J Pharmacol Exp Ther 305: 306-314.
26. Cushman M, Nagarathnam D, Burg DL, Geahlen RL. 1991. Synthesis and protein-tyrosine kinase inhibitory activities of flavonoid analogues. J Med Chem 34: 798-806.
27. Dai R, Zhai S, Wei X, Pincus MR, Vestal RE, Friedman FK. 1998. Inhibition of human cytochrome P450 1A2 by flavones: a molecular modeling study. J Protein Chem 17: 643-650.
28. Di Pietro A, Conseil G, Perez-Victoria JM et al. 2002. Modulation by flavonoids of cell multidrug resistance mediated by P-glycoprotein and related ABC transporters. Cell Mol Life Sci 59: 307-322.
29. Digiovanni J. 1990. Inhibition of chemical carcinogenesis. In Chemical Carcinogenesis and Mutagenesis, Cooper CS, Grover PL (eds). Springer-Verlag: Berlin, 159-253.
30. Doostdar H, Burke MD, Mayer RT. 2000. Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology 144: 31-38.
31. Elattar TM, Virji AS. 1999. The effect of red wine and its components on growth and proliferation of human oral squamous carcinoma cells. Anticancer Res 19: 5407-5414.
32. Ferriola PC, Cody V, Middleton EJ. 1989. Protein kinase C inhibition by plant flavonoids. Kinetic mechanisms and structure-activity relationships. Biochem Pharmacol 38: 1617-1624.
33. Ferte J, Kuhnel JM, Chapuis G, Rolland Y, Lewin G, Schwaller MA. 1999. Flavonoid-related modulators of multidrug resistance: synthesis, pharmacological activity and structure-activity relationships. J Med Chem 42: 478-489.
34. Fisher MB, Paine MF, Strelevitz TJ, Wrighton SA. 2001. The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism. Drug Metab Rev 33: 273-297.
35. Franke AA, Cooney RV, Custer LJ, Mordan LJ, Tanaka Y. 1998. Inhibition of neoplastic transformation and bioavailability of dietary flavonoid agents. Adv Exp Med Biol 439: 237-248.
36. Friedman FK, West D, Sugimura T, Gelboin HV. 1985. Flavone modulators of rat hepatic aryl hydrocarbon hydroxylase. Pharmacology 31: 203-207.
37. Galati G, Teng S, Moridani MY, Chan TS, O'Brien PJ. 2000. Cancer chemoprevention and apoptosis mechanisms induced by dietary polyphenolics. Drug Metab Drug Interact 17: 311-349.
38. Gamet-Payrastre L, Manenti S, Gratacap MP, Tulliez J, Chap H, Payraste B. 1999. Flavonoids and the inhibition of PKC and PI 3- kinase. Gen Pharmacol 32: 279-286.
39. Gary RB. 2003. Overview of dietary flavonoids: nomenclature, occurrence and intake. J Nutr 133: 3248S-3254S.
40. Geahlen RL, Koonchanok NM, McLaughlin JL, Pratt DE. 1989. Inhibition of protein-tyrosine kinase activity by flavanoids and related compounds. J Nat Prod 52: 982-986.
41. Guengerich FP. 1988. Roles of cytochrome P450 enzymes in chemical carcinogenesis and cancer chemotherapy. Cancer Res 48: 2946-2954.
42. Guengerich FP, Shimada T, Yun CH et al. 1994. Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes. Environ Health Perspect 102: 49-53.
43. Harper KA, Morton AD, Rolfe FJ. 1969. The phenolic compounds of black currant juice and their protective effect on ascorbic acid. J Food Technol 4: 255.
44. Havsteen B. 1983. Flavonoids, a class of natural products of high pharmacological potency. Biochem Pharmacol 32: 1141-1148.
45. He K, Iyer KP, Hayes RN, Sinz MW, Woolf TF, Hollenberg PF. 1998. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem Res Toxicol 11: 252-259.
46. Henderson MC, Miranda CL, Stevens JF, Deinzer ML, Buhler DR. 2000. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Xenobiotica 30: 235-251.
47. Hertog MGL, Hollman PCH, Katan MB, Kromhout D. 1993. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands. Nutr Cancer 20: 21-29.
48. Hodek P, Trefil P, Stiborova M. 2002. Flavonoids - potent and versatile biologically active compounds interacting with cytochromes P450. Chem Biol Interact 139: 1-21.
49. Hollman PCH, Arts ICW. 2000. Flavonols, flavones and flavanols - nature, occurrence and dietary burden. J Sci Food Agric 80: 1081-1093.
50. Hughes RE, Wilson HK. 1977. Flavonoids: Some physiological and nutritional consideration. Prog Med Chem 14: 285-301.
51. Johnson IT, Williamson G, Musk SRR. 1994. Anticarcinogenic factors in plant foods: A new class of nutrients? Nutr Res Rev 7: 175-204.
52. Jovanovic SV, Simic MG. 1990. Mechanisms of inactivation of oxygen radicals by dietary antioxidants and their models. Basic Life Sci 52: 127-137.
53. Jovanovic SV, Simic MG. 2000. Antioxidants in nutrition. Ann N Y Acad Sci 899: 326-334.
54. Kagan VE, Tyurina YY. 1998. Recycling and redox cycling of phenolic antioxidants. Ann N Y Acad Sci 854: 425.
55. Kang ZC, Tsai SJ, Lee H. 1999. Quercetin inhibits benzo[a]pyrene-induced DNA adducts in human Hep G2 cells by altering cytochrome P-450 1A1 expression. Nutr Cancer 35: 175-179.
56. Knekt P, Yvinen RJ, SeppSnen R et al. 1997. Dietary flavonoids and the risk of lung cancer and other malignant neoplasms. Am J Epidemiol 146: 223-230.
57. Knowles LM, Zigrossi DA, Tauber RA, Hightower C, Milner JA. 2000. Flavonoids suppress androgen-dependent human prostatic tumor proliferation. Nutr Cancer 38: 116-122.
58. Koide T, Kamei H, Hashimoto Y, Kojima T, Terabe K, Umeda T. 1997. Influence of flavonoids on cell cycle phase as analyzed by flow-cytometry. Cancer Biother Radiopharm 12: 111-115.
59. 1 Synthesis of trimeric, tetrameric, pentameric, and higher oligomeric epicatechin-derived procyanidins having all-4β, 8-interflavan connectivity and their inhibition of cancer cell growth through cell cycle arrest. J Org Chem 68: 1641-1658.
60. Kris-Etherton PM, Hecker KD, Bonanome A et al. 2002. Bioactive compounds in foods: their role in the prevention of cardiovascular disease and cancer. Am J Med 113(Suppl. 9B): 71S-88S.
61. Kummer V, Mašková J, Čanderle J, Zralý Z, Neča J, Machala M. 2001. Estrogenic effect of silymarin in ovariectomized rats. Vet Med Czech 46: 17-23.
62. Kuntz S, Wenzel U, Daniel H. 1999. Comparative analysis of the effects of flavonoids on proliferation, cytotoxicity, and apoptosis in human colon cancer cell lines. Eur J Nutr 38: 133-142.
63. Lasker JM, Huang MT, Conney AH. 1984. In vitro and in vivo activation of oxidative drug metabolism by flavonoids. J Pharmacol Exp Ther 229: 162-170.
64. Lee H, Yeom H, Kim YG et al. 1998. Structure-related inhibition of human hepatic caffeine N3-demethylation by naturally occurring flavonoids. Biochem Pharmacol 55: 1369-1375.
65. Liang YC, Lin-shiau SY, Chen CF, Lin JK. 1997. Suppression of extracellular signals and cell proliferation through EGF receptor binding by (-)-epigallocatechin gallate in human A431 epidermoid carcinoma cells. J Cell Biochem 67: 55-65.
66. Lin JH, Lu AYH. 1998. Inhibition and induction of cytochrome P450 and the clinical implications. Clin Pharmacokinet 35: 361-390.
67. Lin JK, Liang YC, Lin-Shiau SY. 1999. Cancer chemoprevention by tea polyphenols through mitotic signal transduction blockade. Biochemical pharmacology 58: 911-915.
68. Liu RH. 2003. Health benefits of fruit and vegetables are from additive and synergistic combinations of phytochemicals. Am J Clin Nutr 78: 517S-520S.
69. Maenpaa J, Hall SD, Ring BJ, Strom SC, Wrighton SA. 1998. Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenetics 8: 137-155.
70. Mannervik B, Danielson UH. 1998. Glutathione transferases - structure and catalytic activity. CRC Crit Rev Biochem 23: 283-337.
71. Marchand Le L, Murphy SP, Hankin JH, Wilkens LR, Kolonel LN. 2000. Intake of flavonoids and lung cancer. J Natl Cancer Inst 92: 154-160.
72. Marverti G, Andrews PA. 1996. Stimulation of cisdiammine- dichloroplatinum(II) accumulation by modulation of passive permeability with genistein: an altered response in accumulation defective resistant cells. Clin Cancer Res 2: 991-999.
73. McLemore TL, Adelberg S, Liu MC, Hines RN. 1990. Expression of CYP1A1 gene in patients with lung cancer: evidence for cigarette smoke-induced gene expression in normal lung tissue and for altered gene regulation in primary pulmonary carcinomas. J Natl Cancer Inst 82: 1333-1339.
74. Mertens-Talcott SU, Talcott ST, Percival SS. 2003. Low concentrations of quercetin and ellagic acid synergistically influence proliferation, cytotoxicity and apoptosis in MOLT-4 human leukemia cells. J Nutr 133: 2669-2674.
75. Mitsunaga Y, Takanaga H, Matsuo H et al. 2000. Effect of bioflavonoids on vincristine transport across blood-brain barrier. Eur J Pharmacol 395: 193-201.
76. Mizuno N, Niwa T, Yotsumoto Y, Sugiyama Y. 2003. Impact of drug transporter studies on drug discovery and development. Pharmacol Rev 55: 425-461.
77. Moon JY, Lee DW, Park KH. 1998. Inhibition of 7-ethoxycoumarin O-deethylase activity in rat liver microsomes by naturally occurring flavonoids: structure-activity relationships. Xenobiotica 28: 117-126.
78. Mukhtar H, Das M, Khan WA, Bik DP. 1988. Exceptional activity of tannic acid among naturally occurring plant phenols in protecting against 7,12-dimethybenz(a)anthraxcene-, benzo(a)pyrene-, 3-methylcholanthrene-, and N-methyl-N-nitrosourea-induced skin tumorigenesis in mice. Cancer Res 48: 2361-2365.
79. Newmark HL. 1992. Plant phenolic compounds as inhibitors of mutagenesis and carcinogenesis. In Phenolic Compounds in Food and Their Effects on Health. Antioxidants and Cancer Prevention, Huang HT, Ho CT, Lee CY (eds). ACS Symposium Series 507. American Chemical Society: Washington, DC, 48-53.
80. Nissler L, Gebhardt R, Berger S. 2004. Flavonoid binding to a multi-drug-resistance transporter protein: an STD-NMR study. Anal Bioanal Chem 379: 1045-1049.
81. Obach RS. 2000. Inhibition of human cytochrome P450 enzymes by constituents of St. John's wort, an herbal preparation used in the treatment of depression. J Pharmacol Exp Ther 294: 88-95.
82. Obermeier MT, White RE, Yang CS. 1995. Effects of bioflavonoids on hepatic P450 activities. Xenobiotica 25: 575-584.
83. Omiecinski CJ, Remmel RP, Hosagrahara VP. 1999. Concise review of the cytochrome P450s and their roles in toxicology. Toxicol Sci 48: 151-156.
84. Ommen GS, Goodman GE, Thomquist MD, Barnes J, Cullen MR. 1996. Effects of a combination of B-carotene and vitamin A on lung cancer and cardiovascular disease. N Engl J Med 34: 1150-1155.
85. Phang JM, Poore CM, Lopaczynska J, Yeh GC. 1993. Flavonoid-stimulated efflux of 7,12-dimethylbenz[a]anthracene in multidrug-resistant breast cancer cells. Cancer Res 53: 5977-5981.
86. Pietta P, Simonetti P. 1998. Dietary flavonoids and interaction with endogenous antioxidants. Biochem Mol Biol Int 44: 1069-1074.
87. Polkowski K, Mazurek AP. 2000. Biological properties of genistein. A review of in vitro and in vivo data. Acta Pol Pharm Drug Res 57: 135-155.
88. Primiano T, Yu R, Kong ANT. 2001. Signal transduction events elicited by natural products that function as cancer chemopreventive agents. Pharm Biol 39: 83-107.
89. Reiners Jr JJ, Lee JY, Clift RE, Dudley DT, Myrand SP. 1998. PD98059 is an equipotent antagonist of the aryl hydrocarbon receptor and inhibitor of mitogen-activated protein kinase kinase. Mol Pharmacol 53: 438-445.
90. Rice-Evans C. 2001. Flavonoid antioxidants. Curr Med Chem 8: 797-807.
91. Rice-Evans CA, Miller NJ, Bolwell PG, Bramley PM, Pridham JP. 1995. The relative antioxidant activities of plant-derived polyphenols flavonoids. Free Radic Res 22: 375-383.
92. Rice-Evans CA, Miller NJ, Paganga G. 1996. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20: 933-956.
93. Richter M, Ebermann R, Marian B. 1999. Quercetin-induced apoptosis in colorectal tumor cells: possible role of EGF receptor signaling. Nutr Cancer 34: 88-99.
94. Rietveld A, Wiseman S. 2003. Antioxidant effects of tea: evidence from human clinical trials. J Nutr 133: 3285S-3292S.
95. Rusznyak SP, Szent-Gyorgyi A. 1936.Vitamin P: flavonols as vitamins. Nature 138: 27.
96. Scambia G, Raneletti FO, Panici PB et al. 1990. Synergistic antiproliferative activity of quercetin and cisplatin on ovarian cancer cell growth. Anticancer Drugs 1: 45-48.
97. Scambia G, Raneletti FO, Panici PB et al. 1992. Inhibitory effect of quercetin on primary ovarian and endometrial cancers and synergistic activity with cis-diamminedichloroplatinum (II). Gynecol Oncol 45: 13-19.
98. Scambia G, Ranelletti FO, Panici PB et al. 1994. Quercetin potentiates the effect of adriamycin in a multidrug-resistant MCF-7 human breast-cancer cell line: P-glycoprotein as a possible target. Cancer Chemotherapy Pharmacol 34: 459-464.
99. Shapiro AB, Ling V. 1997. Positively cooperative sites for drug transport by P-glycoprotein with distinct drug specificities. Eur J Biochem 250: 130-137.
100. Shen F, Xue X, Weber G. 1999. Tamoxifen and genistein synergistically down-regulate signal transduction and proliferation in estrogen receptor-negative human breast carcinoma MDA-MB-435 cells. Anticancer Res 19: 1657-1662.
101. Shih H. Pickwell GV, Quattrochi LC. 2000. Differential effects of flavonoid compounds on tumor induced activation of human CYP1A2 enhancer. Arch Biochem Biophys 373: 287-294.
102. Sivaraman L, Leatham MP, Yee J, Wilkens LR, Marchand LL. 1994. CYP1A1 genetic polymorphisms and in situ colorectal cancer. Cancer Res 54: 3692-3695.
103. Smith TJ, Guo Z, Guengerich FP, Yang CS. 1996. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Carcinogenesis 17: 809-813.
104. Stephens NG, Parsons A, Schofield PM, Kelly F, Cheeseman K, Mitchinson MJ. 1996. Randomized controlled trial of vitamin E in patients with coronary disease: Cambridge Heart Antioxidant Study (CHAOS). Lancet 347: 781-786.
105. Sukardiman, Darwanto A, Tanjung M, Darmadi MO. 2000. Cytotoxic mechanism of flavonoid from Temu Kunci (Kaempferia pandurata) in cell culture of human mammary carcinoma. Clin Hemorheol Microcirc 23: 185-190.
106. Sun J, He ZG, Cheng G, Wang SJ, Hao XH, Zou MJ. 2004. Multidrug resistance P-glycoprotein: crucial significance in drug disposition and interaction. Med Sci Monitor 10: RA5-RA14.
107. Surth YJ. 1999. Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutat Res 428: 305-327.
108. Svehlíková V, Wang S, Jakubíková J, Williamson G, Mithen R, Bao Y. 2004. Interactions between sulforaphane and apigenin in the induction of UGT1A1 and GSTA1 in CaCo-2 cells. Carcinogenesis 25: 1629-1637.
109. Talalay P, Fahey JW. 2001. Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism. J Nutr 131: 3027S-3033S.
110. Tang W, Stearns RA. 2001. Heterotropic cooperativity of cytochrome P450 3A4 and potential drug-drug interactions. Curr Drug Metab 2: 185-198.
111. Tassaneeyakul W, Birkett DJ, Veronese ME et al. 1993. Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther 265: 401-407.
112. Trela BA, Carlson GP. 1987. Effect of flavonone on mixed-function oxidase and conjugation reactions in rats. Xenobiotica 17: 11-16.
113. Tsyrlov IB, Mikhailenko VM, Gelboin HV. 1994. Isozyme- and species-specific susceptibility of cDNA-expressed CYP1A P450s to different flavonoids. Biochim Biophys Acta 1205: 325-335.
114. Tukey RH, Strassburg CP. 2000. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Ann Rev Pharm Toxicol 40: 581-616.
115. Ueng YF, Kuwabara T, Chun YJ, Guengerich FP. 1997. Cooperativity in oxidations catalyzed by cytochrome P450 3A4. Biochemistry 36: 370-381.
116. Valcic S, Timmermann BN, Alberts DS et al. 1996. Inhibitory effect of six green tea catechins and caffeine on the growth of four selected human tumor cell lines. Anticancer Drugs 7: 461-468.
117. Venkataramanan R, Ramachandran V, Komoroski BJ, Zhang SM, Schiff PL, Strom S. 2000. Milk thistle, a herbal supplement, decreases the activity of CYP3A4 and uridine diphosphoglucuronosyl transferase in human hepatocyte cultures. Drug Metab Dispos 28: 1270-1273.
118. Versantvoort CHM, Broxterman HJ, Lankelma J, Feller N, Pinedo HM. 1994. Competitive inhibition by genistein and ATP dependence of daunorubicin transport in intact MRP overexpressing human small cell lung cancer cells. Biochem Pharmacol 48: 1129-1136.
119. Versantvoort CHM, Schuurhuis GJ, Pinedo HM et al. 1993. Genistein modulates the decreased drug accumulation in non-P-glycoprotein mediated multidrug resistant tumour cells. Br J Cancer 68: 939-946.
120. Vinson JA, Dabbagh Y, Serry M, Jang J. 1995. Plant flavonoids, especially tea flavonols, are powerful antioxidants using an in vitro oxidation model for heart disease. J Agric Food Chem 43: 2800-2802.
121. Walle T, Otake Y, Brubaker JA, Walle UK, Halushka PV. 2001. Disposition and metabolism of the flavonoid chrysin in normal volunteers. Br J Clin Pharmacol 51: 143-146.
122. Wattenberg LW. 1997. An overview of chemoprevention: current status and future prospects. Proc Soc Exp Biol Med 216: 133-141.
123. Yeh GC, Lopaczynska J, Poore CM, Phang JM. 1992. A new functional role for P-glycoprotein: Efflux pump for benzo(a)pyrene in human breast cancer MCF-7 cells. Cancer Res 52: 6692-6695.
124. Yoshida M, Sakai T, Hosokawa N et al. 1990. The effect of quercetin on cell cycle progression and growth of human gastric cancer cells. FEBS Lett 260: 10-13.
125. Yoshida M, Yamamoto M, Nikaido T. 1992. Quercetin arrests human leukemic T-cells in late G1 phase of the cell cycle. Cancer Res 2: 6676-6681.
126. Yu R, Jiao JJ, Duh JL et al. 1997. Activation of mitogen-activated protein kinases by green tea polyphenols: potential signaling pathways in the regulation of antioxidant-responsive element-mediated phase II enzyme gene expression. Carcinogenesis 18: 451-456.
127. Yusuf S, Dagenais G, Pogue J, Bosch J, Sleigh P. 2000. Vitamin E supplementation and cardiovascular events in high-risk patients. The Heart Outcomes Prevention Evaluation Study Investigators. N Engl J Med 342: 154-160.
128. Zand RS, Jenkins DJ, Diamandis EP. 2000. Steroid hormone activity of flavonoids and related compounds. Breast Cancer Res Treat 62: 35-49.
129. Zhai S, Dai R, Friedman FK, Vestal RE. 1998. Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids. Drug Metab Dispos 26: 989-992.