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Reports

Phytochemical Regulation of UDP-Glucuronosyltransferases: Implications for Cancer Prevention

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Pages 121-141 | Received 12 Jan 2007, Accepted 27 Apr 2007, Published online: 05 Dec 2007

References

  • Rushmore , T H and Kong , A N . 2002 . Pharmacogenomics, regulation and signaling pathways of phase I and II drug metabolizing enzymes . Curr Drug Metab , 3 : 481 – 490 .
  • Sugatani , J , Nishitani , S , Yamakawa , K , Yoshinari , K Sueyoshi , T . 2005 . Transcriptional regulation of human UGT1A1 gene expression: activated glucocorticoid receptor enhances constitutive androstane receptor/pregnane X receptor-mediated UDP-glucuronosyltransferase 1A1 regulation with glucocorticoid receptor-interacting protein 1 . Mol Pharmacol , 67 : 845 – 855 .
  • Zhou , J , Zhang , J and Xie , W . 2005 . Xenobiotic nuclear receptor-mediated regulation of UDP-glucuronosyl-transferases . Curr Drug Metab , 6 : 289 – 298 .
  • Brierley , C H , Senafi , S B , Clarke , D , Hsu , M H Johnson , E F . 1996 . Regulation of the human bilirubin UDP-glucuronosyltransferase gene . Adv Enzyme Regul , 36 : 85 – 97 .
  • Gregory , P A , Lewinsky , R H , Gardner-Stephen , D A and Mackenzie , P I . 2004 . Regulation of UDP glucuronosyltransferases in the gastrointestinal tract . Toxicol Appl Pharmacol , 199 : 354 – 363 .
  • Owens , I S , Basu , N K and Banerjee , R . 2005 . UDP-glucuronosyltransferases: gene structures of UGT1 and UGT2 families . Methods Enzymol , 400 : 1 – 22 .
  • Gong , Q H , Cho , J W , Huang , T , Potter , C Gholami , N . 2001 . Thirteen UDPglucuronosyltransferase genes are encoded at the human UGT1 gene complex locus . Pharmacogenetics , 11 : 357 – 368 .
  • Tukey , R H and Strassburg , C P . 2000 . Human UDP-glucuronosyltransferases: metabolism, expression, and disease . Annu Rev Pharmacol Toxicol , 40 : 581 – 616 .
  • Mackenzie , P I , Walter Bock , K , Burchell , B , Guillemette , C Ikushiro , S . 2005 . Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily . Pharmacogenet Genomics , 15 : 677 – 685 .
  • Nagar , S and Remmel , R P . 2006 . Uridine diphosphoglucuronosyltransferase pharmacogenetics and cancer . Oncogene , 25 : 1659 – 1672 .
  • Moon , Y J , Wang , X and Morris , M E . 2006 . Dietary flavonoids: effects on xenobiotic and carcinogen metabolism . Toxicol In Vitro , 20 : 187 – 210 .
  • Strassburg , C P , Manns , M P and Tukey , R H . 1997 . Differential down-regulation of the UDP-glucuronosyltransferase 1A locus is an early event in human liver and biliary cancer . Cancer Res , 57 : 2979 – 2985 .
  • Guillemette , C , Belanger , A and Lepine , J . 2004 . Metabolic inactivation of estrogens in breast tissue by UDP-glucuronosyltransferase enzymes: an overview . Breast Cancer Res , 6 : 246 – 254 .
  • Peters , U , Sinha , R , Bell , D A , Rothman , N Grant , D J . 2004 . Urinary mutagenesis and fried red meat intake: influence of cooking temperature, phenotype, and genotype of metabolizing enzymes in a controlled feeding study . Environ Mol Mutagen , 43 : 53 – 74 .
  • Wells , P G , Mackenzie , P I , Chowdhury , J R , Guillemette , C Gregory , P A . 2004 . Glucuronidation and the UDP-glucuronosyltransferases in health and disease . Drug Metab Dispos , 32 : 281 – 290 .
  • Hu , Z and Wells , P G . 1992 . In vitro and in vivo biotransformation and covalent binding of benzo(a)pyrene in Gunn and RHA rats with a genetic deficiency in bilirubin uridine diphosphate-glucuronosyltransferase . J Pharmacol Exp Ther , 263 : 334 – 342 .
  • Hu , Z and Wells , P G . 1994 . Modulation of benzo[a]pyrene bioactivation by glucuronidation in lymphocytes and hepatic microsomes from rats with a hereditary deficiency in bilirubin UDP-glucuronosyltransferase . Toxicol Appl Pharmacol , 127 : 306 – 313 .
  • Berges , R , Siess , M H , Arnault , I , Auger , J Kahane , R . 2004 . Comparison of the chemopreventive efficacies of garlic powders with different alliin contents against aflatoxin B1 carcinogenicity in rats . Carcinogenesis , 25 : 1953 – 1959 .
  • Pantuck , E J , Hsiao , K C , Loub , W D , Wattenberg , L W Kuntzman , R . 1976 . Stimulatory effect of vegetables on intestinal drug metabolism in the rat . J Pharmacol Exp Ther , 198 : 278 – 283 .
  • Pantuck , E J , Pantuck , C B , Garland , W A , Min , B H Wattenberg , L W . 1979 . Stimulatory effect of brussels sprouts and cabbage on human drug metabolism . Clin Pharmacol Ther , 25 : 88 – 95 .
  • Uotila , P and Aitio , A . 1979 . The effects of dietary vegetables on rat intestinal and hepatic metabolism of xenobiotics . Res Commun Chem Pathol Pharmacol , 26 : 425 – 428 .
  • Pantuck , E J , Pantuck , C B , Anderson , K E , Wattenberg , L W Conney , A H . 1984 . Effect of brussels sprouts and cabbage on drug conjugation . Clin Pharmacol Ther , 35 : 161 – 169 .
  • Hecht , S S , Carmella , S G and Murphy , S E . 1999 . Effects of watercress consumption on urinary metabolites of nicotine in smokers . Cancer Epidemiol Biomarkers Prev , 8 : 907 – 913 .
  • Hecht , S S , Chung , F L , Richie , J P Jr. , Akerkar , S A Borukhova , A . 1995 . Effects of watercress consumption on metabolism of a tobacco-specific lung carcinogen in smokers . Cancer Epidemiol Biomarkers Prev , 4 : 877 – 884 .
  • Brennan , P , Hsu , C C , Moullan , N , Szeszenia-Dabrowska , N Lissowska , J . 2005 . Effect of cruciferous vegetables on lung cancer in patients stratified by genetic status: a mendelian randomisation approach . Lancet , 366 : 1558 – 1560 .
  • Le Marchand , L , Hankin , J H , Kolonel , L N , Beecher , G R Wilkens , L R . 1993 . Intake of specific carotenoids and lung cancer risk . Cancer Epidemiol Biomarkers Prev , 2 : 183 – 187 .
  • Swanson , C A , Mao , B L , Li , J Y , Lubin , J H Yao , S X . 1992 . Dietary determinants of lung-cancer risk: results from a case-control study in Yunnan Province, China . Int J Cancer , 50 : 876 – 880 .
  • Wang , L I , Giovannucci , E L , Hunter , D , Neuberg , D Su , L . 2004 . Dietary intake of Cruciferous vegetables, Glutathione S-transferase (GST) polymorphisms and lung cancer risk in a caucasian population . Cancer Causes Control , 15 : 977 – 985 .
  • Lee , A H , Fraser , M L and Binns , C W . 2005 . Possible role for green tea in ovarian cancer prevention . Future Oncol , 1 : 771 – 777 .
  • McKay , D L and Blumberg , J B . 2002 . The role of tea in human health: an update . J Am Coll Nutr , 21 : 1 – 13 .
  • Sun , C L , Yuan , J M , Koh , W P and Yu , M C . 2006 . Green tea, black tea and breast cancer risk: a meta-analysis of epidemiological studies . Carcinogenesis , 27 : 1310 – 1315 .
  • Sun , C L , Yuan , J M , Koh , W P and Yu , M C . 2006 . Green tea, black tea and colorectal cancer risk: a meta-analysis of epidemiologic studies . Carcinogenesis , 27 : 1301 – 1309 .
  • Surh , Y J . 2003 . Cancer chemoprevention with dietary phytochemicals . Nat Rev Cancer , 3 : 768 – 780 .
  • Talalay , P . 2000 . Chemoprotection against cancer by induction of phase 2 enzymes . Biofactors , 12 : 5 – 11 .
  • Bianchini , F and Vainio , H . 2004 . Isothiocyanates in cancer prevention . Drug Metab Rev , 36 : 655 – 667 .
  • Conaway , C C , Yang , Y M and Chung , F L . 2002 . Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans . Curr Drug Metab , 3 : 233 – 255 .
  • Keum , Y S , Jeong , W S and Kong , A N . 2004 . Chemoprevention by isothiocyanates and their underlying molecular signaling mechanisms . Mutat Res , 555 : 191 – 202 .
  • Zhang , Y . 2004 . Cancer-preventive isothiocyanates: measurement of human exposure and mechanism of action . Mutat Res , 555 : 173 – 190 .
  • Dingley , K H , Ubick , E A , Chiarappa-Zucca , M L , Nowell , S Abel , S . 2003 . Effect of dietary constituents with chemopreventive potential on adduct formation of a low dose of the heterocyclic amines PhIP and IQ and phase II hepatic enzymes . Nutr Cancer , 46 : 212 – 221 .
  • Guo , D , Schut , H A , Davis , C D , Snyderwine , E G Bailey , G S . 1995 . Protection by chlorophyllin and indole-3-carbinol against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced DNA adducts and colonic aberrant crypts in the F344 rat . Carcinogenesis , 16 : 2931 – 2937 .
  • Thimmulappa , R K , Mai , K H , Srisuma , S , Kensler , T W Yamamoto , M . 2002 . Identification of Nrf2-regulated genes induced by the chemopreventive agent sulforaphane by oligonucleotide microarray . Cancer Res , 62 : 5196 – 5203 .
  • Xu , M , Bailey , A C , Hernaez , J F , Taoka , C R Schut , H A . 1996 . Protection by green tea, black tea, and indole-3-carbinol against 2-amino-3-methylimidazo[4,5-f]quinoline-induced DNA adducts and colonic aberrant crypts in the F344 rat . Carcinogenesis , 17 : 1429 – 1434 .
  • Guyonnet , D , Siess , M H , Le Bon , A M and Suschetet , M . 1999 . Modulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissues . Toxicol Appl Pharmacol , 154 : 50 – 58 .
  • Haber , D , Siess , M H , Canivenc-Lavier , M C , Le Bon , A M and Suschetet , M . 1995 . Differential effects of dietary diallyl sulfide and diallyl disulfide on rat intestinal and hepatic drug-metabolizing enzymes . J Toxicol Environ Health , 44 : 423 – 434 .
  • Haber , D , Siess , M H , de Waziers , I , Beaune , P and Suschetet , M . 1994 . Modification of hepatic drug-metabolizing enzymes in rat fed naturally occurring allyl sulphides . Xenobiotica , 24 : 169 – 182 .
  • Siess , M H , Le Bon , A M , Canivenc-Lavier , M C and Suschetet , M . 1997 . Modification of hepatic drug-metabolizing enzymes in rats treated with alkyl sulfides . Cancer Lett , 120 : 195 – 201 .
  • Maliakal , P P and Wanwimolruk , S . 2001 . Effect of herbal teas on hepatic drug metabolizing enzymes in rats . J Pharm Pharmacol , 53 : 1323 – 1329 .
  • Nikaidou , S , Ishizuka , M , Maeda , Y , Hara , Y Kazusaka , A . 2005 . Effect of components of green tea extracts, caffeine and catechins on hepatic drug metabolizing enzyme activities and mutagenic transformation of carcinogens . Jpn J Vet Res , 52 : 185 – 192 .
  • Bu-Abbas , A , Clifford , M N , Ioannides , C and Walker , R . 1995 . Stimulation of rat hepatic UDP-glucuronosyl transferase activity following treatment with green tea . Food Chem Toxicol , 33 : 27 – 30 .
  • Bu-Abbas , A , Clifford , M N , Walker , R and Ioannides , C . 1998 . Contribution of caffeine and flavanols in the induction of hepatic Phase II activities by green tea . Food Chem Toxicol , 36 : 617 – 621 .
  • Embola , C W , Sohn , O S , Fiala , E S and Weisburger , J H . 2002 . Induction of UDP-glucuronosyltransferase 1 (UDP-GT1) gene complex by green tea in male F344 rats . Food Chem Toxicol , 40 : 841 – 844 .
  • Santana-Rios , G , Orner , G A , Xu , M , Izquierdo-Pulido , M and Dashwood , R H . 2001 . Inhibition by white tea of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced colonic aberrant crypts in the F344 rat . Nutr Cancer , 41 : 98 – 103 .
  • Sohn , O S , Surace , A , Fiala , E S , Richie , J P Jr. Colosimo , S . 1994 . Effects of green and black tea on hepatic xenobiotic metabolizing systems in the male F344 rat . Xenobiotica , 24 : 119 – 127 .
  • Sugatani , J , Yamakawa , K , Tonda , E , Nishitani , S Yoshinari , K . 2004 . The induction of human UDP-glucuronosyltransferase 1A1 mediated through a distal enhancer module by flavonoids and xenobiotics . Biochem Pharmacol , 67 : 989 – 1000 .
  • Yang , X Y , Zhao , W P , Li , Y Q , Sun , Z Y Zhang , Y . 2006 . The role of NF-E2-related factor 2 in the induction of uridine 5′-diphosphate-glucuronosyltransferase 1A and its isoforms by epigallocatechin gallate in colon cancer cells . Zhonghua Yi Xue Za Zhi , 86 : 82 – 87 .
  • Chrungoo , V J , Reen , R K , Singh , K and Singh , J . 1997 . Effects of silymarin on UDP-glucuronic acid and glucuronidation activity in the rat isolated hepatocytes and liver in relation to D-galactosamine toxicity . Indian J Exp Biol , 35 : 256 – 263 .
  • D'Andrea , V , Perez , L M and Sanchez Pozzi , E J . 2005 . Inhibition of rat liver UDP-glucuronosyltransferase by silymarin and the metabolite silibinin-glucuronide . Life Sci , 77 : 683 – 692 .
  • Venkataramanan , R , Ramachandran , V , Komoroski , B J , Zhang , S Schiff , P L . 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 .
  • Ueng , Y F , Shyu , C C , Lin , Y L , Park , S S Liao , J F . 2000 . Effects of baicalein and wogonin on drug-metabolizing enzymes in C57BL/6J mice . Life Sci , 67 : 2189 – 2200 .
  • Williams , J A , Ring , B J , Cantrell , V E , Campanale , K Jones , D R . 2002 . Differential modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1)-catalyzed estradiol-3-glucuronidation by the addition of UGT1A1 substrates and other compounds to human liver microsomes . Drug Metab Dispos , 30 : 1266 – 1273 .
  • Brouard , C , Siess , M H , Vernevaut , M F and Suschetet , M . 1988 . Comparison of the effects of feeding quercetin or flavone on hepatic and intestinal drug-metabolizing enzymes of the rat . Food Chem Toxicol , 26 : 99 – 103 .
  • Canivenc-Lavier , M C , Vernevaut , M F , Totis , M , Siess , M H Magdalou , J . 1996 . Comparative effects of flavonoids and model inducers on drug-metabolizing enzymes in rat liver . Toxicology , 114 : 19 – 27 .
  • Siess , M H , Le Bon , A M and Suschetet , M . 1992 . Dietary modification of drug-metabolizing enzyme activities: dose-response effect of flavonoids . J Toxicol Environ Health , 35 : 141 – 152 .
  • van , d er , Logt , E M , Roelofs , H M , Nagengast , F M and Peters , W H . 2003 . Induction of rat hepatic and intestinal UDP-glucuronosyltransferases by naturally occurring dietary anticarcinogens . Carcinogenesis , 24 : 1651 – 1656 .
  • Galijatovic , A , Otake , Y , Walle , U K and Walle , T . 2001 . Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in Caco-2 cells–potential role in carcinogen bioinactivation . Pharm Res , 18 : 374 – 379 .
  • Galijatovic , A , Walle , U K and Walle , T . 2000 . Induction of UDP-glucuronosyltransferase by the flavonoids chrysin and quercetin in Caco-2 cells . Pharm Res , 17 : 21 – 26 .
  • Walle , T , Otake , Y , Galijatovic , A , Ritter , J K and Walle , U K . 2000 . Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in the human hepatoma cell line hep G2 . Drug Metab Dispos , 28 : 1077 – 1082 .
  • Walle , U K and Walle , T . 2002 . Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements . Drug Metab Dispos , 30 : 564 – 569 .
  • Chen , C and Kong , A N . 2005 . Dietary cancer-chemopreventive compounds: from signaling and gene expression to pharmacological effects . Trends Pharmacol Sci , 26 : 318 – 326 .
  • Lampe , J W . 2003 . Isoflavonoid and lignan phytoestrogens as dietary biomarkers . J Nutr , 133 : 956S – 964S . (Suppl 3)
  • Appelt , L C and Reicks , M M . 1999 . Soy induces phase II enzymes but does not inhibit dimethylbenz[a]anthracene-induced carcinogenesis in female rats . J Nutr , 129 : 1820 – 1826 .
  • Sun , X Y , Plouzek , C A , Henry , J P , Wang , T T and Phang , J M . 1998 . Increased UDP-glucuronosyltransferase activity and decreased prostate specific antigen production by biochanin A in prostate cancer cells . Cancer Res , 58 : 2379 – 2384 .
  • Pfeiffer , E , Treiling , C R , Hoehle , S I and Metzler , M . 2005 . Isoflavones modulate the glucuronidation of estradiol in human liver microsomes . Carcinogenesis , 26 : 2172 – 2178 .
  • Basu , N K , Ciotti , M , Hwang , M S , Kole , L Mitra , P S . 2004 . Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake . J Biol Chem , 279 : 1429 – 1441 .
  • Basu , N K , Kole , L , Kubota , S and Owens , I S . 2004 . Human UDP-glucuronosyltransferases show atypical metabolism of mycophenolic acid and inhibition by curcumin . Drug Metab Dispos , 32 : 768 – 773 .
  • Basu , N K , Kole , L and Owens , I S . 2003 . Evidence for phosphorylation requirement for human bilirubin UDP-glucuronosyltransferase (UGT1A1) activity . Biochem Biophys Res Commun , 303 : 98 – 104 .
  • Goud , V K , Polasa , K and Krishnaswamy , K . 1993 . Effect of turmeric on xenobiotic metabolising enzymes . Plant Foods Hum Nutr , 44 : 87 – 92 .
  • Naganuma , M , Saruwatari , A , Okamura , S and Tamura , H . 2006 . Turmeric and curcumin modulate the conjugation of 1-naphthol in Caco-2 cells . Biol Pharm Bull , 29 : 1476 – 1479 .
  • Yueh , M F and Tukey , R H . 2007 . Nrf2-Keap1 Signaling pathway regulates human UGT1A1 expression in vitro and in transgenic UGT1 mice . J Biol Chem , 282 : 8749 – 8758 .
  • Janosek , J , Hilscherova , K , Blaha , L and Holoubek , I . 2006 . Environmental xenobiotics and nuclear receptors–interactions, effects and in vitro assessment . Toxicol In Vitro , 20 : 18 – 37 .
  • Kohle , C and Bock , K W . 2006 . Activation of coupled Ah receptor and Nrf2 gene batteries by dietary phytochemicals in relation to chemoprevention . Biochem Pharmacol , 72 : 795 – 805 .
  • Quadri , S A , Qadri , A N , Hahn , M E , Mann , K K and Sherr , D H . 2000 . The bioflavonoid galangin blocks aryl hydrocarbon receptor activation and polycyclic aromatic hydrocarbon-induced pre-B cell apoptosis . Mol Pharmacol , 58 : 515 – 525 .
  • Auyeung , D J , Kessler , F K and Ritter , J K . 2003 . Mechanism of rat UDP-glucuronosyltransferase 1A6 induction by oltipraz: evidence for a contribution of the Aryl hydrocarbon receptor pathway . Mol Pharmacol , 63 : 119 – 127 .
  • Munzel , P A , Lehmkoster , T , Bruck , M , Ritter , J K and Bock , K W . 1998 . Aryl hydrocarbon receptor-inducible or constitutive expression of human UDP glucuronosyltransferase UGT1A6 . Arch Biochem Biophys , 350 : 72 – 78 .
  • Nishimura , N , Yonemoto , J , Miyabara , Y , Fujii-Kuriyama , Y and Tohyama , C . 2005 . Altered thyroxin and retinoid metabolic response to 2,3,7,8-tetrachlorodibenzo-p-dioxin in aryl hydrocarbon receptor-null mice . Arch Toxicol , 79 : 260 – 267 .
  • Riedy , M , Wang , J Y , Miller , A P , Buckler , A Hall , J M . 2000 . Genomic organization of the UGT2b gene cluster on human chromosome 4q13 . Pharmacogenetics , 10 : 251 – 260 .
  • Bock , K W , Gschaidmeier , H , Heel , H , Lehmkoster , T Munzel , P A . 1998 . AH receptor-controlled transcriptional regulation and function of rat and human UDP-glucuronosyltransferase isoforms . Adv Enzyme Regul , 38 : 207 – 222 .
  • Chen , S , Beaton , D , Nguyen , N , Senekeo-Effenberger , K Brace-Sinnokrak , E . 2005 . Tissue-specific, inducible, and hormonal control of the human UDP-glucuronosyltransferase-1 (UGT1) locus . J Biol Chem , 280 : 37547 – 37557 .
  • Finel , M , Li , X , Gardner-Stephen , D , Bratton , S , Mackenzie , P I and Radominska-Pandya , A . 2005 . Human UDP-glucuronosyltransferase 1A5: identification, expression, and activity . J Pharmacol Exp Ther , 315 : 1143 – 1149 .
  • Munzel , P A , Bookjans , G , Mehner , G , Lehmkoster , T and Bock , K W . 1996 . Tissue-specific 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible expression of human UDP-glucuronosyltransferase UGT1A6 . Arch Biochem Biophys , 335 : 205 – 210 .
  • Munzel , P A , Schmohl , S , Buckler , F , Jaehrling , J Raschko , F T . 2003 . Contribution of the Ah receptor to the phenolic antioxidant-mediated expression of human and rat UDP-glucuronosyltransferase UGT1A6 in Caco-2 and rat hepatoma 5L cells . Biochem Pharmacol , 66 : 841 – 847 .
  • Munzel , P A , Schmohl , S , Heel , H , Kalberer , K Bock-Hennig , B S . 1999 . Induction of human UDP glucuronosyltransferases (UGT1A6, UGT1A9, and UGT2B7) by t-butylhydroquinone and 2,3,7,8-tetrachlorodibenzo-p-dioxin in Caco-2 cells . Drug Metab Dispos , 27 : 569 – 573 .
  • Amakura , Y , Tsutsumi , T , Nakamura , M , Kitagawa , H Fujino , J . 2003 . Activation of the aryl hydrocarbon receptor by some vegetable constituents determined using in vitro reporter gene assay . Biol Pharm Bull , 26 : 532 – 539 .
  • Ashida , H , Fukuda , I , Yamashita , T and Kanazawa , K . 2000 . Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin . FEBS Lett , 476 : 213 – 217 .
  • Gradelet , S , Astorg , P , Leclerc , J , Chevalier , J Vernevaut , M F . 1996 . Effects of canthaxanthin, astaxanthin, lycopene and lutein on liver xenobiotic-metabolizing enzymes in the rat . Xenobiotica , 26 : 49 – 63 .
  • Jacobs , M N and Lewis , D F . 2002 . Steroid hormone receptors and dietary ligands: a selected review . Proc Nutr Soc , 61 : 105 – 122 .
  • Zhang , S , Qin , C and Safe , S H . 2003 . Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context . Environ Health Perspect , 111 : 1877 – 1882 .
  • Amakura , Y , Tsutsumi , T , Sasaki , K , Yoshida , T and Maitani , T . 2003 . Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin . Biol Pharm Bull , 26 : 1754 – 1760 .
  • Ciolino , H P and Yeh , G C . 1999 . Inhibition of aryl hydrocarbon-induced cytochrome P-450 1A1 enzyme activity and CYP1A1 expression by resveratrol . Mol Pharmacol , 56 : 760 – 767 .
  • Fukuda , I , Sakane , I , Yabushita , Y , Sawamura , S Kanazawa , K . 2004 . Black tea extract suppresses transformation of aryl hydrocarbon receptor induced by dioxin . Biofactors , 21 : 367 – 369 .
  • Palermo , C M , Hernando , J I , Dertinger , S D , Kende , A S and Gasiewicz , T A . 2003 . Identification of potential aryl hydrocarbon receptor antagonists in green tea . Chem Res Toxicol , 16 : 865 – 872 .
  • Williams , S N , Shih , H , Guenette , D K , Brackney , W Denison , M S . 2000 . Comparative studies on the effects of green tea extracts and individual tea catechins on human CYP1A gene expression . Chem Biol Interact , 128 : 211 – 229 .
  • Zhang , L , Zheng , W and Jefcoate , C R . 2003 . Ah receptor regulation of mouse Cyp1B1 is additionally modulated by a second novel complex that forms at two AhR response elements . Toxicol Appl Pharmacol , 192 : 174 – 190 .
  • Casper , R F , Quesne , M , Rogers , I M , Shirota , T Jolivet , A . 1999 . Resveratrol has antagonist activity on the aryl hydrocarbon receptor: implications for prevention of dioxin toxicity . Mol Pharmacol , 56 : 784 – 790 .
  • Ciolino , H P , Daschner , P J and Yeh , G C . 1998 . Resveratrol inhibits transcription of CYP1A1 in vitro by preventing activation of the aryl hydrocarbon receptor . Cancer Res , 58 : 5707 – 5712 .
  • Orans , J , Teotico , D G and Redinbo , M R . 2005 . The nuclear xenobiotic receptor pregnane X receptor: recent insights and new challenges . Mol Endocrinol , 19 : 2891 – 2900 .
  • Handschin , C and Meyer , U A . 2005 . Regulatory network of lipid-sensing nuclear receptors: roles for CAR, PXR, LXR, and FXR . Arch Biochem Biophys , 433 : 387 – 396 .
  • Masuyama , H , Suwaki , N , Tateishi , Y , Nakatsukasa , H Segawa , T . 2005 . The pregnane X receptor regulates gene expression in a ligand- and promoter-selective fashion . Mol Endocrinol , 19 : 1170 – 1180 .
  • Sugatani , J , Sueyoshi , T , Negishi , M and Miwa , M . 2005 . Regulation of the human UGT1A1 gene by nuclear receptors constitutive active/androstane receptor, pregnane X receptor, and glucocorticoid receptor . Methods Enzymol , 400 : 92 – 104 .
  • Jacobs , M N , Nolan , G T and Hood , S R . 2005 . Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR) . Toxicol Appl Pharmacol , 209 : 123 – 133 .
  • Watkins , R E , Maglich , J M , Moore , L B , Wisely , G B Noble , S M . 2003 . 2.1 A crystal structure of human PXR in complex with the St. John's wort compound hyperforin . Biochemistry , 42 : 1430 – 1438 .
  • Watkins , R E , Wisely , G B , Moore , L B , Collins , J L Lambert , M H . 2001 . The human nuclear xenobiotic receptor PXR: structural determinants of directed promiscuity . Science , 292 : 2329 – 2333 .
  • Bock , K W and Kohle , C . 2005 . UDP-glucuronosyltransferase 1A6: structural, functional, and regulatory aspects . Methods Enzymol , 400 : 57 – 75 .
  • Gardner-Stephen , D , Heydel , J M , Goyal , A , Lu , Y Xie , W . 2004 . Human PXR variants and their differential effects on the regulation of human UDP-glucuronosyltransferase gene expression . Drug Metab Dispos , 32 : 340 – 347 .
  • Xie , W , Yeuh , M F , Radominska-Pandya , A , Saini , S P Negishi , Y . 2003 . Control of steroid, heme, and carcinogen metabolism by nuclear pregnane X receptor and constitutive androstane receptor . Proc Natl Acad Sci USA , 100 : 4150 – 4155 .
  • Chen , C , Staudinger , J L and Klaassen , C D . 2003 . Nuclear receptor, pregname X receptor, is required for induction of UDP-glucuronosyltranferases in mouse liver by pregnenolone-16 alpha-carbonitrile . Drug Metab Dispos , 31 : 908 – 915 .
  • Lin , J H and Wong , B K . 2002 . Complexities of glucuronidation affecting in vitro in vivo extrapolation . Curr Drug Metab , 3 : 623 – 646 .
  • Menard , C , Lamiable , D , Vistelle , R , Morin , E and Ratanasavanh , D . 2000 . Induction and inhibition of cicletanine metabolism in cultured hepatocytes and liver microsomes from rats . Fundam Clin Pharmacol , 14 : 509 – 518 .
  • Shelby , M K and Klaassen , C D . 2006 . Induction of rat UDP-glucuronosyltransferases in liver and duodenum by microsomal enzyme inducers that activate various transcriptional pathways . Drug Metab Dispos , 34 : 1772 – 1778 .
  • Tukey , R H , Pendurthi , U R , Nguyen , N T , Green , M D and Tephly , T R . 1993 . Cloning and characterization of rabbit liver UDP-glucuronosyltransferase cDNAs. Developmental and inducible expression of 4-hydroxybiphenyl UGT2B13 . J Biol Chem , 268 : 15260 – 15266 .
  • Moi , P , Chan , K , Asunis , I , Cao , A and Kan , Y W . 1994 . Isolation of NF-E2-related factor 2 (Nrf2), a NF-E2-like basic leucine zipper transcriptional activator that binds to the tandem NF-E2/AP1 repeat of the beta-globin locus control region . Proc Natl Acad Sci USA , 91 : 9926 – 9930 .
  • Venugopal , R and Jaiswal , A K . 1998 . Nrf2 and Nrf1 in association with Jun proteins regulate antioxidant response element-mediated expression and coordinated induction of genes encoding detoxifying enzymes . Oncogene , 17 : 3145 – 3156 .
  • Dinkova-Kostova , A T , Holtzclaw , W D , Cole , R N , Itoh , K Wakabayashi , N . 2002 . Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants . Proc Natl Acad Sci USA , 99 : 11908 – 11913 .
  • Kobayashi , A , Kang , M I , Okawa , H , Ohtsuji , M Zenke , Y . 2004 . Oxidative stress sensor Keap1 functions as an adaptor for Cul3-based E3 ligase to regulate proteasomal degradation of Nrf2 . Mol Cell Biol , 24 : 7130 – 7139 .
  • McMahon , M , Itoh , K , Yamamoto , M and Hayes , J D . 2003 . Keap1-dependent proteasomal degradation of transcription factor Nrf2 contributes to the negative regulation of antioxidant response element-driven gene expression . J Biol Chem , 278 : 21592 – 21600 .
  • Zhang , D D , Lo , S C , Sun , Z , Habib , G M Lieberman , M W . 2005 . Ubiquitination of Keap1, a BTB-Kelch substrate adaptor protein for Cul3, targets Keap1 for degradation by a proteasome-independent pathway . J Biol Chem , 280 : 30091 – 30099 .
  • Itoh , K , Wakabayashi , N , Katoh , Y , Ishii , T Igarashi , K . 1999 . Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain . Genes Dev , 13 : 76 – 86 .
  • Ben-Dor , A , Steiner , M , Gheber , L , Danilenko , M Dubi , N . 2005 . Carotenoids activate the antioxidant response element transcription system . Mol Cancer Ther , 4 : 177 – 186 .
  • Nakamura , Y , Yoshida , C , Murakami , A , Ohigashi , H Osawa , T . 2004 . Zerumbone, a tropical ginger sesquiterpene, activates phase II drug metabolizing enzymes . FEBS Lett , 572 : 245 – 250 .
  • Wu , C C , Hsu , M C , Hsieh , C W , Lin , J B Lai , P H . 2006 . Upregulation of heme oxygenase-1 by Epigallocatechin-3-gallate via the phosphatidylinositol 3-kinase/Akt and ERK pathways . Life Sci , 78 : 2889 – 2897 .
  • Itoh , K , Chiba , T , Takahashi , S , Ishii , T Igarashi , K . 1997 . An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements . Biochem Biophys Res Commun , 236 : 313 – 322 .
  • Nguyen , T , Sherratt , P J and Pickett , C B . 2003 . Regulatory mechanisms controlling gene expression mediated by the antioxidant response element . Annu Rev Pharmacol Toxicol , 43 : 233 – 260 .
  • Katsuoka , F , Motohashi , H , Ishii , T , Aburatani , H Engel , J D . 2005 . Genetic evidence that small maf proteins are essential for the activation of antioxidant response element-dependent genes . Mol Cell Biol , 25 : 8044 – 8051 .
  • Chan , K and Kan , Y W . 1999 . Nrf2 is essential for protection against acute pulmonary injury in mice . Proc Natl Acad Sci USA , 96 : 12731 – 12736 .
  • Chanas , S A , Jiang , Q , McMahon , M , McWalter , G K McLellan , L I . 2002 . Loss of the Nrf2 transcription factor causes a marked reduction in constitutive and inducible expression of the glutathione S-transferase Gsta1, Gsta2, Gstm1, Gstm2, Gstm3 and Gstm4 genes in the livers of male and female mice . Biochem J , 365 : 405 – 416 .
  • McMahon , M , Itoh , K , Yamamoto , M , Chanas , S A Henderson , C J . 2001 . The cap'n'collar basic leucine zipper transcription factor Nrf2 (NF-E2 p45-related factor 2) controls both constitutive and inducible expression of intestinal detoxification and glutathione biosynthetic enzymes . Cancer Res , 61 : 3299 – 3307 .
  • McWalter , G K , Higgins , L G , McLellan , L I , Henderson , C J Song , L . 2004 . Transcription factor Nrf2 is essential for induction of NAD(P)H:quinone oxidoreductase 1, glutathione S-transferases, and glutamate cysteine ligase by broccoli seeds and isothiocyanates . J Nutr , 134 : 3499S – 3506S .
  • Ramos-Gomez , M , Kwak , M K , Dolan , P M , Itoh , K Yamamoto , M . 2001 . Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in nrf2 transcription factor-deficient mice . Proc Natl Acad Sci USA , 98 : 3410 – 3415 .
  • Nguyen , T , Sherratt , P J , Huang , H C , Yang , C S and Pickett , C B . 2003 . Increased protein stability as a mechanism that enhances Nrf2-mediated transcriptional activation of the antioxidant response element: degradation of Nrf2 by the 26 S proteasome . J Biol Chem , 278 : 4536 – 4541 .
  • Owuor , E D and Kong , A N . 2002 . Antioxidants and oxidants regulated signal transduction pathways . Biochem Pharmacol , 64 : 765 – 770 .
  • Huang , H C , Nguyen , T and Pickett , C B . 2002 . Phosphorylation of Nrf2 at Ser-40 by protein kinase C regulates antioxidant response element-mediated transcription . J Biol Chem , 277 : 42769 – 42774 .
  • Rushworth , S A , Ogborne , R M , Charalambos , C A and O'Connell , M A . 2006 . Role of protein kinase C delta in curcumin-induced antioxidant response element-mediated gene expression in human monocytes . Biochem Biophys Res Commun , 341 : 1007 – 1016 .
  • Bloom , D A and Jaiswal , A K . 2003 . Phosphorylation of Nrf2 at Ser40 by protein kinase C in response to antioxidants leads to the release of Nrf2 from INrf2, but is not required for Nrf2 stabilization/accumulation in the nucleus and transcriptional activation of antioxidant response element-mediated NAD(P)H:quinone oxidoreductase-1 gene expression . J Biol Chem , 278 : 44675 – 44682 .
  • Kim , S O , Kundu , J K , Shin , Y K , Park , J H Cho , M H . 2005 . [6]-Gingerol inhibits COX-2 expression by blocking the activation of p38 MAP kinase and NF-kappaB in phorbol ester-stimulated mouse skin . Oncogene , 24 : 2558 – 2567 .
  • Aggarwal , B B and Shishodia , S . 2006 . Molecular targets of dietary agents for prevention and therapy of cancer . Biochem Pharmacol , 71 : 1397 – 1421 .
  • Balogun , E , Hoque , M , Gong , P , Killeen , E Green , C J . 2003 . Curcumin activates the haem oxygenase-1 gene via regulation of Nrf2 and the antioxidant-responsive element . Biochem J , 371 : 887 – 895 .
  • Ishikawa , Y and Kitamura , M . 2000 . Anti-apoptotic effect of quercetin: intervention in the JNK- and ERK-mediated apoptotic pathways . Kidney Int , 58 : 1078 – 1087 .
  • Lin , J K , Chen , Y C , Huang , Y T and Lin-Shiau , S Y . 1997 . Suppression of protein kinase C and nuclear oncogene expression as possible molecular mechanisms of cancer chemoprevention by apigenin and curcumin . J Cell Biochem Suppl , 28–29 : 39 – 48 .
  • Liu , J Y , Lin , S J and Lin , J K . 1993 . Inhibitory effects of curcumin on protein kinase C activity induced by 12-O-tetradecanoyl-phorbol-13-acetate in NIH 3T3 cells . Carcinogenesis , 14 : 857 – 861 .
  • Salh , B , Assi , K , Templeman , V , Parhar , K Owen , D . 2003 . Curcumin attenuates DNB-induced murine colitis . Am J Physiol Gastrointest Liver Physiol , 285 : G235 – G243 .
  • Chen , C , Yu , R , Owuor , E D and Kong , A N . 2000 . Activation of antioxidant-response element (ARE), mitogen-activated protein kinases (MAPKs) and caspases by major green tea polyphenol components during cell survival and death . Arch Pharm Res , 23 : 605 – 612 .
  • Dong , Z , Ma , W , Huang , C and Yang , C S . 1997 . Inhibition of tumor promoter-induced activator protein 1 activation and cell transformation by tea polyphenols, (-)-epigallocatechin gallate, and theaflavins . Cancer Res , 57 : 4414 – 4419 .
  • Kim , H S , Kim , M H , Jeong , M , Hwang , Y S Lim , S H . 2004 . EGCG blocks tumor promoter-induced MMP-9 expression via suppression of MAPK and AP-1 activation in human gastric AGS cells . Anticancer Res , 24 : 747 – 753 .
  • Maeda-Yamamoto , M , Suzuki , N , Sawai , Y , Miyase , T Sano , M . 2003 . Association of suppression of extracellular signal-regulated kinase phosphorylation by epigallocatechin gallate with the reduction of matrix metalloproteinase activities in human fibrosarcoma HT1080 cells . J Agric Food Chem , 51 : 1858 – 1863 .
  • Masuda , M , Suzui , M and Weinstein , I B . 2001 . Effects of epigallocatechin-3-gallate on growth, epidermal growth factor receptor signaling pathways, gene expression, and chemosensitivity in human head and neck squamous cell carcinoma cell lines . Clin Cancer Res , 7 : 4220 – 4229 .
  • Pianetti , S , Guo , S , Kavanagh , K T and Sonenshein , G E . 2002 . Green tea polyphenol epigallocatechin-3 gallate inhibits Her-2/neu signaling, proliferation, and transformed phenotype of breast cancer cells . Cancer Res , 62 : 652 – 655 .
  • Sah , J F , Balasubramanian , S , Eckert , R L and Rorke , E A . 2004 . Epigallocatechin-3-gallate inhibits epidermal growth factor receptor signaling pathway: evidence for direct inhibition of ERK1/2 and AKT kinases . J Biol Chem , 279 : 12755 – 12762 .
  • Wu , B T , Hung , P F , Chen , H C , Huang , R N Chang , H H . 2005 . The apoptotic effect of green tea (-)-epigallocatechin gallate on 3T3-L1 preadipocytes depends on the Cdk2 pathway . J Agric Food Chem , 53 : 5695 – 5701 .
  • Hou , Z , Lambert , J D , Chin , K V and Yang , C S . 2004 . Effects of tea polyphenols on signal transduction pathways related to cancer chemoprevention . Mutat Res , 555 : 3 – 19 .
  • Shih , C M , Lin , H , Liang , Y C , Lee , W S Bi , W F . 2004 . Concentration-dependent differential effects of quercetin on rat aortic smooth muscle cells . Eur J Pharmacol , 496 : 41 – 48 .
  • Wang , X , Clubbs , E A and Bomser , J A . 2006 . Genistein modulates prostate epithelial cell proliferation via estrogen- and extracellular signal-regulated kinase-dependent pathways . J Nutr Biochem , 17 : 204 – 210 .
  • Llorens , F , Miro , F A , Casanas , A , Roher , N Garcia , L . 2004 . Unbalanced activation of ERK1/2 and MEK1/2 in apigenin-induced HeLa cell death . Exp Cell Res , 299 : 15 – 26 .
  • Sarkar , F H and Li , Y . 2004 . Cell signaling pathways altered by natural chemopreventive agents . Mutat Res , 555 : 53 – 64 .
  • Lee , J S and Surh , Y J . 2005 . Nrf2 as a novel molecular target for chemoprevention . Cancer Lett , 224 : 171 – 184 .
  • Xu , C , Yuan , X , Pan , Z , Shen , G Kim , J H . 2006 . Mechanism of action of isothiocyanates: the induction of ARE-regulated genes is associated with activation of ERK and JNK and the phosphorylation and nuclear translocation of Nrf2 . Mol Cancer Ther , 5 : 1918 – 1926 .
  • Nguyen , T , Yang , C S and Pickett , C B . 2004 . The pathways and molecular mechanisms regulating Nrf2 activation in response to chemical stress . Free Radic Biol Med , 37 : 433 – 441 .
  • Shen , G , Hebbar , V , Nair , S , Xu , C Li , W . 2004 . Regulation of Nrf2 transactivation domain activity. The differential effects of mitogen-activated protein kinase cascades and synergistic stimulatory effect of Raf and CREB-binding protein . J Biol Chem , 279 : 23052 – 23060 .
  • Hayes , J D and McMahon , M . 2001 . Molecular basis for the contribution of the antioxidant responsive element to cancer chemoprevention . Cancer Lett , 174 : 103 – 113 .
  • Kwak , M K , Wakabayashi , N and Kensler , T W . 2004 . Chemoprevention through the Keap1-Nrf2 signaling pathway by phase 2 enzyme inducers . Mutat Res , 555 : 133 – 148 .
  • Metz , R P and Ritter , J K . 1998 . Transcriptional activation of the UDP-glucuronosyltransferase 1A7 gene in rat liver by aryl hydrocarbon receptor ligands and oltipraz . J Biol Chem , 273 : 5607 – 5614 .
  • Rushmore , T H , Morton , M R and Pickett , C B . 1991 . The antioxidant responsive element. Activation by oxidative stress and identification of the DNA consensus sequence required for functional activity . J Biol Chem , 266 : 11632 – 11639 .
  • Wang , M , Li , Y Q , Zhong , N , Chen , J Xu , X Q . 2005 . [Induction of uridine 5′-diphosphate-glucuronosyltransferase gene expression by sulforaphane and its mechanism: experimental study in human colon cancel cells] . Zhonghua Yi Xue Za Zhi , 85 : 819 – 824 .
  • Turgeon , D , Carrier , J S , Levesque , E , Beatty , B G Belanger , A . 2000 . Isolation and characterization of the human UGT2B15 gene, localized within a cluster of UGT2B genes and pseudogenes on chromosome 4 . J Mol Biol , 295 : 489 – 504 .
  • Barbier , O , Duran-Sandoval , D , Pineda-Torra , I , Kosykh , V Fruchart , J C . 2003 . Peroxisome proliferator-activated receptor alpha induces hepatic expression of the human bile acid glucuronidating UDP-glucuronosyltransferase 2B4 enzyme . J Biol Chem , 278 : 32852 – 32860 .
  • Barbier , O , Villeneuve , L , Bocher , V , Fontaine , C Torra , I P . 2003 . The UDP-glucuronosyltransferase 1A9 enzyme is a peroxisome proliferator-activated receptor alpha and gamma target gene . J Biol Chem , 278 : 13975 – 13983 .
  • Frank , C , Gonzalez , M M , Oinonen , C , Dunlop , T W and Carlberg , C . 2003 . Characterization of DNA complexes formed by the nuclear receptor constitutive androstane receptor . J Biol Chem , 278 : 43299 – 43310 .
  • Maglich , J M , Watson , J , McMillen , P J , Goodwin , B Willson , T M . 2004 . The nuclear receptor CAR is a regulator of thyroid hormone metabolism during caloric restriction . J Biol Chem , 279 : 19832 – 19838 .
  • Ansell , P J , Lo , S C , Newton , L G , Espinosa-Nicholas , C Zhang , D D . 2005 . Repression of cancer protective genes by 17beta-estradiol: ligand-dependent interaction between human Nrf2 and estrogen receptor alpha . Mol Cell Endocrinol , 243 : 27 – 34 .
  • Liu , R H . 2004 . Potential synergy of phytochemicals in cancer prevention: mechanism of action . J Nutr , 134 : 3479S – 3485S .
  • Talalay , P and Fahey , J W . 2001 . Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism . J Nutr , 131 : 3027S – 3033S .
  • Jacobs , D R Jr. and Steffen , L M . 2003 . Nutrients, foods, and dietary patterns as exposures in research: a framework for food synergy . Am J Clin Nutr , 78 : 508S – 513S .
  • Svehlikova , V , Wang , S , Jakubikova , J , Williamson , G Mithen , R . 2004 . Interactions between sulforaphane and apigenin in the induction of UGT1A1 and GSTA1 in CaCo-2 cells . Carcinogenesis , 25 : 1629 – 1637 .
  • Carlson , D B and Perdew , G H . 2002 . A dynamic role for the Ah receptor in cell signaling? Insights from a diverse group of Ah receptor interacting proteins . J Biochem Mol Toxicol , 16 : 317 – 325 .
  • Kato , S , Sato , T , Watanabe , T , Takemasa , S Masuhiro , Y . 2005 . Function of nuclear sex hormone receptors in gene regulation . Cancer Chemother Pharmacol , 56 : 4 – 9 . (Suppl 1)
  • Matthews , J and Gustafsson , J A . 2006 . Estrogen receptor and aryl hydrocarbon receptor signaling pathways . Nucl Recept Signal , 4 : e016
  • Pocar , P , Fischer , B , Klonisch , T and Hombach-Klonisch , S . 2005 . Molecular interactions of the aryl hydrocarbon receptor and its biological and toxicological relevance for reproduction . Reproduction , 129 : 379 – 389 .
  • Safe , S . 2001 . Molecular biology of the Ah receptor and its role in carcinogenesis . Toxicol Lett , 120 : 1 – 7 .
  • Wormke , M , Stoner , M , Saville , B and Safe , S . 2000 . Crosstalk between estrogen receptor alpha and the aryl hydrocarbon receptor in breast cancer cells involves unidirectional activation of proteasomes . FEBS Lett , 478 : 109 – 112 .
  • Wormke , M , Stoner , M , Saville , B , Walker , K Abdelrahim , M . 2003 . The aryl hydrocarbon receptor mediates degradation of estrogen receptor alpha through activation of proteasomes . Mol Cell Biol , 23 : 1843 – 1855 .
  • Cullinan , S B , Gordan , J D , Jin , J , Harper , J W and Diehl , J A . 2004 . The Keap1-BTB protein is an adaptor that bridges Nrf2 to a Cul3-based E3 ligase: oxidative stress sensing by a Cul3-Keap1 ligase . Mol Cell Biol , 24 : 8477 – 8486 .
  • Buckley , D B and Klaassen , C D . 2006 . Tissue- and gender-specific mRNA expression of UDP-glucuronosyltransferases (UGTs) in mice . Drug Metab Dispos , 35 : 121 – 127 .
  • Mercke Odeberg , J , Andrade , J , Holmberg , K , Hoglund , P Malmqvist , U . 2006 . UGT1A polymorphisms in a Swedish cohort and a human diversity panel, and the relation to bilirubin plasma levels in males and females . Eur J Clin Pharmacol , 62 : 829 – 837 .
  • Takeuchi , T , Tsutsumi , O , Nakamura , N , Ikezuki , Y Takai , Y . 2004 . Gender difference in serum bisphenol A levels may be caused by liver UDP-glucuronosyltransferase activity in rats . Biochem Biophys Res Commun , 325 : 549 – 554 .
  • Visser , T J , van Haasteren , G A , Linkels , E , Kaptei , E van Toor , H . 1996 . Gender-specific changes in thyroid hormone-glucuronidating enzymes in rat liver during short-term fasting and long-term food restriction . Eur J Endocrinol , 135 : 489 – 497 .
  • Diry , M , Tomkiewicz , C , Koehle , C , Coumoul , X Bock , K W . 2006 . Activation of the dioxin/aryl hydrocarbon receptor (AhR) modulates cell plasticity through a JNK-dependent mechanism . Oncogene , 25 : 5570 – 5574 .
  • Tan , Z , Huang , M , Puga , A and Xia , Y . 2004 . A critical role for MAP kinases in the control of Ah receptor complex activity . Toxicol Sci , 82 : 80 – 87 .
  • Yim , S , Oh , M , Choi , S M and Park , H . 2004 . Inhibition of the MEK-1/p42 MAP kinase reduces aryl hydrocarbon receptor-DNA interactions . Biochem Biophys Res Commun , 322 : 9 – 16 .
  • Bock , K W and Kohle , C . 2004 . Coordinate regulation of drug metabolism by xenobiotic nuclear receptors: UGTs acting together with CYPs and glucuronide transporters . Drug Metab Rev , 36 : 595 – 615 .
  • Padmanabhan , B , Tong , K I , Ohta , T , Nakamura , Y Scharlock , M . 2006 . Structural basis for defects of Keap1 activity provoked by its point mutations in lung cancer . Mol Cell , 21 : 689 – 700 .
  • Court , M H . 2005 . Isoform-selective probe substrates for in vitro studies of human UDP-glucuronosyltransferases . Methods Enzymol , 400 : 104 – 116 .
  • Strassburg , C P , Kneip , S , Topp , J , Obermayer-Straub , P Barut , A . 2000 . Polymorphic gene regulation and interindividual variation of UDP-glucuronosyltransferase activity in human small intestine . J Biol Chem , 275 : 36164 – 36171 .
  • Court , M H , Hao , Q , Krishnaswamy , S , Bekaii-Saab , T Al-Rohaimi , A . 2004 . UDP-glucuronosyltransferase (UGT) 2B15 pharmacogenetics: UGT2B15 D85Y genotype and gender are major determinants of oxazepam glucuronidation by human liver . J Pharmacol Exp Ther , 310 : 656 – 665 .
  • Plewka , A , Kaminski , M and Plewka , D . 1997 . The influence of age and some inducers on UDP-glucuronyltransferase activity . Exp Gerontol , 32 : 305 – 313 .
  • Strassburg , C P , Vogel , A , Kneip , S , Tukey , R H and Manns , M P . 2002 . Polymorphisms of the human UDP-glucuronosyltransferase (UGT) 1A7 gene in colorectal cancer . Gut , 50 : 851 – 856 .
  • Dalhoff , K , Buus Jensen , K and Enghusen Poulsen , H . 2005 . Cancer and molecular biomarkers of phase 2 . Methods Enzymol , 400 : 618 – 627 .
  • Efferth , T and Volm , M . 2005 . Pharmacogenetics for individualized cancer chemotherapy . Pharmacol Ther , 107 : 155 – 176 .
  • Girard , H , Thibaudeau , J , Court , M H , Fortier , L C Villeneuve , L . 2005 . UGT1A1 polymorphisms are important determinants of dietary carcinogen detoxification in the liver . Hepatology , 42 : 448 – 457 .
  • Lampe , J W and Peterson , S . 2002 . Brassica, biotransformation and cancer risk: genetic polymorphisms alter the preventive effects of cruciferous vegetables . J Nutr , 132 : 2991 – 2994 .
  • Nowell , S A , Ahn , J , Rae , J M , Scheys , J O Trovato , A . 2005 . Association of genetic variation in tamoxifen-metabolizing enzymes with overall survival and recurrence of disease in breast cancer patients . Breast Cancer Res Treat , 91 : 249 – 258 .
  • Peterson , S , Bigler , J , Horner , N K , Potter , J D and Lampe , J W . 2005 . Cruciferae interact with the UGT1A1∗28 polymorphism to determine serum bilirubin levels in humans . J Nutr , 135 : 1051 – 1055 .
  • Adegoke , O J , Shu , X O , Gao , Y T , Cai , Q Breyer , J . 2004 . Genetic polymorphisms in uridine diphospho-glucuronosyltransferase 1A1 (UGT1A1) and risk of breast cancer . Breast Cancer Res Treat , 85 : 239 – 245 .
  • Duguay , Y , McGrath , M , Lepine , J , Gagne , J F Hankinson , S E . 2004 . The functional UGT1A1 promoter polymorphism decreases endometrial cancer risk . Cancer Res , 64 : 1202 – 1207 .
  • Guillemette , C , Millikan , R C , Newman , B and Housman , D E . 2000 . Genetic polymorphisms in uridine diphospho-glucuronosyltransferase 1A1 and association with breast cancer among African Americans . Cancer Res , 60 : 950 – 956 .
  • Sparks , R , Ulrich , C M , Bigler , J , Tworoger , S S Yasui , Y . 2004 . UDP-glucuronosyltransferase and sulfotransferase polymorphisms, sex hormone concentrations, and tumor receptor status in breast cancer patients . Breast Cancer Res , 6 : R488 – 498 .
  • Calcagno , A M , Ludwig , J A , Fostel , J M , Gottesman , M M and Ambudkar , S V . 2006 . Comparison of drug transporter levels in normal colon, colon cancer, and Caco-2 cells: impact on drug disposition and discovery . Mol Pharm , 3 : 87 – 93 .
  • Fenton , J I and Hord , N G . 2006 . Stage matters: choosing relevant model systems to address hypotheses in diet and cancer chemoprevention research . Carcinogenesis , 27 : 893 – 902 .
  • Sun , D , Lennernas , H , Welage , L S , Barnett , J L Landowski , C P . 2002 . Comparison of human duodenum and Caco-2 gene expression profiles for 12,000 gene sequences tags and correlation with permeability of 26 drugs . Pharm Res , 19 : 1400 – 1416 .
  • Petri , N , Tannergren , C , Holst , B , Mellon , F A Bao , Y . 2003 . Absorption/metabolism of sulforaphane and quercetin, and regulation of phase II enzymes, in human jejunum in vivo . Drug Metab Dispos , 31 : 805 – 813 .
  • Brangi , M , Litman , T , Ciotti , M , Nishiyama , K Kohlhagen , G . 1999 . Camptothecin resistance: role of the ATP-binding cassette (ABC), mitoxantrone-resistance half-transporter (MXR), and potential for glucuronidation in MXR-expressing cells . Cancer Res , 59 : 5938 – 5946 .
  • Cummings , J , Zelcer , N , Allen , J D , Yao , D Boyd , G . 2004 . Glucuronidation as a mechanism of intrinsic drug resistance in colon cancer cells: contribution of drug transport proteins . Biochem Pharmacol , 67 : 31 – 39 .
  • Felton , J S and Malfatti , M A . 2006 . What do diet-induced changes in phase I and II enzymes tell us about prevention from exposure to heterocyclic amines? . J Nutr , 136 : 2683S – 2684S .
  • Giuliani , L , Ciotti , M , Stoppacciaro , A , Pasquini , A Silvestri , I . 2005 . UDP-glucuronosyltransferases 1A expression in human urinary bladder and colon cancer by immunohistochemistry . Oncol Rep , 13 : 185 – 191 .
  • Knize , M G and Felton , J S . 2005 . Formation and human risk of carcinogenic heterocyclic amines formed from natural precursors in meat . Nutr Rev , 63 : 158 – 165 .
  • Malfatti , M A and Felton , J S . 2004 . Human UDP-glucuronosyltransferase 1A1 is the primary enzyme responsible for the N-glucuronidation of N-hydroxy-PhIP in vitro . Chem Res Toxicol , 17 : 1137 – 1144 .
  • Malfatti , M A , Wu , R W and Felton , J S . 2005 . The effect of UDP-glucuronosyltransferase 1A1 expression on the mutagenicity and metabolism of the cooked-food carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in CHO cells . Mutat Res , 570 : 205 – 214 .
  • Malfatti , M A , Ubick , E A and Felton , J S . 2005 . The impact of glucuronidation on the bioactivation and DNA adduction of the cooked-food carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in vivo . Carcinogenesis , 26 : 2019 – 2028 .
  • Tukey , R H , Strassburg , C P and Mackenzie , P I . 2002 . Pharmacogenomics of human UDP-glucuronosyltransferases and irinotecan toxicity . Mol Pharmacol , 62 : 446 – 450 .
  • Sun , D , Chen , G , Dellinger , R W , Duncan , K Fang , J L . 2006 . Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants . Breast Cancer Res , 8 : R50
  • Meyskens , F L Jr. and Szabo , E . 2005 . Diet and cancer: the disconnect between epidemiology and randomized clinical trials . Cancer Epidemiol Biomarkers Prev , 14 : 1366 – 1369 .
  • Gwilt , P R , Lear , C L , Tempero , M A , Birt , D D Grandjean , A C . 1994 . The effect of garlic extract on human metabolism of acetaminophen . Cancer Epidemiol Biomarkers Prev , 3 : 155 – 160 .
  • Taioli , E , Garbers , S , Bradlow , H L , Carmella , S G Akerkar , S . 1997 . Effects of indole-3-carbinol on the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers . Cancer Epidemiol Biomarkers Prev , 6 : 517 – 522 .
  • Vang , O , Mehrota , K , Georgellis , A and Andersen , O . 1999 . Effects of dietary broccoli on rat testicular xenobiotic metabolizing enzymes . Eur J Drug Metab Pharmacokinet , 24 : 353 – 359 .
  • Humblot , C , Lhoste , E , Knasmuller , S , Gloux , K Bruneau , A . 2004 . Protective effects of brussels sprouts, oligosaccharides and fermented milk towards 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced genotoxicity in the human flora associated F344 rat: role of xenobiotic metabolising enzymes and intestinal microflora . J Chromatogr B Analyt Technol Biomed Life Sci , 802 : 231 – 237 .
  • Kassie , F , Rabot , S , Uhl , M , Huber , W Qin , H M . 2002 . Chemoprotective effects of garden cress (Lepidium sativum) and its constituents towards 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ)-induced genotoxic effects and colonic preneoplastic lesions . Carcinogenesis , 23 : 1155 – 1161 .
  • Kassie , F , Laky , B , Gminski , R , Mersch-Sundermann , V Scharf , G . 2003 . Effects of garden and water cress juices and their constituents, benzyl and phenethyl isothiocyanates, towards benzo(a)pyrene-induced DNA damage: a model study with the single cell gel electrophoresis/Hep G2 assay . Chem Biol Interact , 142 : 285 – 296 .
  • Tepsuwan , A , Kupradinun , P and Kusamran , W R . 1999 . Effect of Siamese cassia leaves on the activities of chemical carcinogen metabolizing enzymes and on mammary gland carcinogenesis in the rat . Mutat Res , 428 : 363 – 373 .
  • Debersac , P , Heydel , J M , Amiot , M J , Goudonnet , H Artur , Y . 2001 . Induction of cytochrome P450 and/or detoxication enzymes by various extracts of rosemary: description of specific patterns . Food Chem Toxicol , 39 : 907 – 918 .
  • Teyssier , C , Amiot , M J , Mondy , N , Auger , J Kahane , R . 2001 . Effect of onion consumption by rats on hepatic drug-metabolizing enzymes . Food Chem Toxicol , 39 : 981 – 987 .
  • Le Bon , A M , Vernevaut , M F , Guenot , L , Kahane , R Auger , J . 2003 . Effects of garlic powders with varying alliin contents on hepatic drug metabolizing enzymes in rats . J Agric Food Chem , 51 : 7617 – 7623 .
  • Elegbede , J A , Maltzman , T H , Elson , C E and Gould , M N . 1993 . Effects of anticarcinogenic monoterpenes on phase II hepatic metabolizing enzymes . Carcinogenesis , 14 : 1221 – 1223 .
  • Siess , M H , Guillermic , M , Le Bon , A M and Suschetet , M . 1989 . Induction of monooxygenase and transferase activities in rat by dietary administration of flavonoids . Xenobiotica , 19 : 1379 – 1386 .
  • Siess , M H , Mas , J P , Canivenc-Lavier , M C and Suschetet , M . 1996 . Time course of induction of rat hepatic drug-metabolizing enzyme activities following dietary administration of flavonoids . J Toxicol Environ Health , 49 : 481 – 496 .
  • Shertzer , H G and Sainsbury , M . 1991 . Chemoprotective and hepatic enzyme induction properties of indole and indenoindole antioxidants in rats . Food Chem Toxicol , 29 : 391 – 400 .
  • Ahn , D , Putt , D , Kresty , L , Stoner , G D Fromm , D . 1996 . The effects of dietary ellagic acid on rat hepatic and esophageal mucosal cytochromes P450 and phase II enzymes . Carcinogenesis , 17 : 821 – 828 .
  • Szaefer , H , Cichocki , M , Brauze , D and Baer-Dubowska , W . 2004 . Alteration in phase I and II enzyme activities and polycyclic aromatic hydrocarbons-DNA adduct formation by plant phenolics in mouse epidermis . Nutr Cancer , 48 : 70 – 77 .
  • Hebbar , V , Shen , G , Hu , R , Kim , B R Chen , C . 2005 . Toxicogenomics of resveratrol in rat liver . Life Sci , 76 : 2299 – 2314 .
  • Ghosh , B , Sardar , S , Roy , K and Chatterjee , M . 1995 . Role of beta-carotene on the changes in activity patterns and levels of biotransforming enzymes in transplantable murine lymphoma . Cancer Lett , 90 : 191 – 197 .
  • Haberkorn , V , Heydel , J M , Mounie , J , Artur , Y and Goudonnet , H . 2001 . Influence of vitamin A status on the regulation of uridine (5′-)diphosphate-glucuronosyltransferase (UGT) 1A1 and UGT1A6 expression by L-triiodothyronine . Br J Nutr , 85 : 289 – 297 .
  • Haberkorn , V , Heydel , J M , Mounie , J , Artur , Y and Goudonnet , H . 2002 . Vitamin A modulates the effects of thyroid hormone on UDP-glucuronosyltransferase expression and activity in rat liver . Mol Cell Endocrinol , 190 : 167 – 175 .
  • Haberkorn , V , Oziol , L and Goudonnet , H . 2003 . 9-cis-Retinoic acid regulation of four UGT isoforms in hepatocytes from rats with various thyroid states . Pharm Res , 20 : 1568 – 1573 .
  • Lhoste , E F , Gloux , K , De Waziers , I , Garrido , S Lory , S . 2004 . The activities of several detoxication enzymes are differentially induced by juices of garden cress, water cress and mustard in human HepG2 cells . Chem Biol Interact , 150 : 211 – 219 .
  • Harrington , W R , Sengupta , S and Katzenellenbogen , B S . 2006 . Estrogen regulation of the glucuronidation enzyme UGT2B15 in estrogen receptor-positive breast cancer cells . Endocrinology , 147 : 3843 – 3850 .
  • Basten , G P , Bao , Y and Williamson , G . 2002 . Sulforaphane and its glutathione conjugate but not sulforaphane nitrile induce UDP-glucuronosyl transferase (UGT1A1) and glutathione transferase (GSTA1) in cultured cells . Carcinogenesis , 23 : 1399 – 1404 .
  • Bacon , J R , Williamson , G , Garner , R C , Lappin , G Langouet , S . 2003 . Sulforaphane and quercetin modulate PhIP-DNA adduct formation in human HepG2 cells and hepatocytes . Carcinogenesis , 24 : 1903 – 1911 .
  • Yokoi , T , Narita , M , Nagai , E , Hagiwara , H Aburada , M . 1995 . Inhibition of UDP-glucuronosyltransferase by aglycons of natural glucuronides in kampo medicines using SN-38 as a substrate . Jpn J Cancer Res , 86 : 985 – 989 .
  • Chen , W and Bowden , G T . 1999 . Activation of p38 MAP kinase and ERK are required for ultraviolet-B induced c-fos gene expression in human keratinocytes . Oncogene , 18 : 7469 – 7476 .
  • Chen , C C , Chow , M P , Huang , W C , Lin , Y C and Chang , Y J . 2004 . Flavonoids inhibit tumor necrosis factor-alpha-induced up-regulation of intercellular adhesion molecule-1 (ICAM-1) in respiratory epithelial cells through activator protein-1 and nuclear factor-kappaB: structure-activity relationships . Mol Pharmacol , 66 : 683 – 693 .
  • Ciolino , H P , Daschner , P J and Yeh , G C . 1999 . Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially . Biochem J , 340(Pt 3) : 715 – 722 .
  • Liu , D Y , Zhu , H J , Zheng , Y F and Zhu , X Q . 2006 . [Kaempferol activates human steroid and xenobiotic receptor-mediated cytochrome P450 3A4 transcription] . Zhejiang Da Xue Xue Bao Yi Xue Ban , 35 : 14 – 17 .
  • O'Prey , J , Brown , J , Fleming , J and Harrison , P R . 2003 . Effects of dietary flavonoids on major signal transduction pathways in human epithelial cells . Biochem Pharmacol , 66 : 2075 – 2088 .
  • Chen , C and Kong , A N . 2004 . Dietary chemopreventive compounds and ARE/EpRE signaling . Free Radic Biol Med , 36 : 1505 – 1516 .
  • Liu , D Y , Yang , M , Zhu , H J , Zheng , Y F and Zhu , X Q . 2006 . [Human pregnane X receptor-mediated transcriptional regulation of cytochrome P450 3A4 by some phytochemicals] . Zhejiang Da Xue Xue Bao Yi Xue Ban , 35 : 8 – 13 .
  • Ruiz , P A and Haller , D . 2006 . Functional diversity of flavonoids in the inhibition of the proinflammatory NF-kappaB, IRF, and Akt signaling pathways in murine intestinal epithelial cells . J Nutr , 136 : 664 – 671 .
  • Martin , D , Rojo , A I , Salinas , M , Diaz , R Gallardo , G . 2004 . Regulation of heme oxygenase-1 expression through the phosphatidylinositol 3-kinase/Akt pathway and the Nrf2 transcription factor in response to the antioxidant phytochemical carnosol . J Biol Chem , 279 : 8919 – 8929 .
  • Ciolino , H P and Yeh , G C . 1999 . The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor . Br J Cancer , 79 : 1340 – 1346 .
  • Chan , H Y , Wang , H and Leung , L K . 2003 . The red clover (Trifolium pratense) isoflavone biochanin A modulates the biotransformation pathways of 7,12-dimethylbenz[a]anthracene . Br J Nutr , 90 : 87 – 92 .
  • Han , E H , Kim , J Y and Jeong , H G . 2006 . Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells . Arch Pharm Res , 29 : 570 – 576 .
  • Chaudhary , L R and Hruska , K A . 2003 . Inhibition of cell survival signal protein kinase B/Akt by curcumin in human prostate cancer cells . J Cell Biochem , 89 : 1 – 5 .
  • Chen , L , Mohr , S N and Yang , C S . 1996 . Decrease of plasma and urinary oxidative metabolites of acetaminophen after consumption of watercress by human volunteers . Clin Pharmacol Ther , 60 : 651 – 660 .
  • Chen , Y R and Tan , T H . 1998 . Inhibition of the c-Jun N-terminal kinase (JNK) signaling pathway by curcumin . Oncogene , 17 : 173 – 178 .
  • Ciolino , H P , Daschner , P J , Wang , T T and Yeh , G C . 1998 . Effect of curcumin on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells . Biochem Pharmacol , 56 : 197 – 206 .
  • Kim , J H , Xu , C , Keum , Y S , Reddy , B Conney , A . 2006 . Inhibition of EGFR signaling in human prostate cancer PC-3 cells by combination treatment with beta-phenylethyl isothiocyanate and curcumin . Carcinogenesis , 27 : 475 – 482 .
  • Limtrakul , P , Lipigorngoson , S , Namwong , O , Apisariyakul , A and Dunn , F W . 1997 . Inhibitory effect of dietary curcumin on skin carcinogenesis in mice . Cancer Lett , 116 : 197 – 203 .
  • Rinaldi , A L , Morse , M A , Fields , H W , Rothas , D A Pei , P . 2002 . Curcumin activates the aryl hydrocarbon receptor yet significantly inhibits (-)-benzo(a)pyrene-7R-trans-7,8-dihydrodiol bioactivation in oral squamous cell carcinoma cells and oral mucosa . Cancer Res , 62 : 5451 – 5456 .
  • Van Dross , R , Xue , Y , Knudson , A and Pelling , J C . 2003 . The chemopreventive bioflavonoid apigenin modulates signal transduction pathways in keratinocyte and colon carcinoma cell lines . J Nutr , 133 : 3800S – 3804S .
  • Alkhalaf , M and Jaffal , S . 2006 . Potent antiproliferative effects of resveratrol on human osteosarcoma SJSA1 cells: novel cellular mechanisms involving the ERKs/p53 cascade . Free Radic Biol Med , 41 : 318 – 325 .
  • Atten , M J , Attar , B M , Milson , T and Holian , O . 2001 . Resveratrol-induced inactivation of human gastric adenocarcinoma cells through a protein kinase C-mediated mechanism . Biochem Pharmacol , 62 : 1423 – 1432 .
  • Chen , C Y , Jang , J H , Li , M H and Surh , Y J . 2005 . Resveratrol upregulates heme oxygenase-1 expression via activation of NF-E2-related factor 2 in PC12 cells . Biochem Biophys Res Commun , 331 : 993 – 1000 .
  • Kaneider , N C , Mosheimer , B , Reinisch , N , Patsch , J R and Wiedermann , C J . 2004 . Inhibition of thrombin-induced signaling by resveratrol and quercetin: effects on adenosine nucleotide metabolism in endothelial cells and platelet-neutrophil interactions . Thromb Res , 114 : 185 – 194 .
  • Kundu , J K and Surh , Y J . 2004 . Molecular basis of chemoprevention by resveratrol: NF-kappaB and AP-1 as potential targets . Mutat Res , 555 : 65 – 80 .
  • Kutuk , O , Poli , G and Basaga , H . 2006 . Resveratrol protects against 4-hydroxynonenal-induced apoptosis by blocking JNK and c-JUN/ AP-1 signaling . Toxicol Sci , 90 : 120 – 132 .
  • Niles , R M . 2004 . Signaling pathways in retinoid chemoprevention and treatment of cancer . Mutat Res , 555 : 81 – 96 .
  • Olson , E R , Naugle , J E , Zhang , X , Bomser , J A and Meszaros , J G . 2005 . Inhibition of cardiac fibroblast proliferation and myofibroblast differentiation by resveratrol . Am J Physiol Heart Circ Physiol , 288 : H1131 – 1138 .
  • She , Q B , Bode , A M , Ma , W Y , Chen , N Y and Dong , Z . Resveratrol-induced activation of p53 and apoptosis is mediated by extracellular-signal-regulated protein kinases and p38 kinase . Cancer Res , 61 1604 – 1610 .
  • She , Q B , Huang , C , Zhang , Y and Dong , Z . 2002 . Involvement of c-jun NH(2)-terminal kinases in resveratrol-induced activation of p53 and apoptosis . Mol Carcinog , 33 : 244 – 250 .
  • Slater , S J , Seiz , J L , Cook , A C , Stagliano , B A and Buzas , C J . 2003 . Inhibition of protein kinase C by resveratrol . Biochim Biophys Acta , 1637 : 59 – 69 .
  • Stewart , J R and O'Brian , C A . 2004 . Resveratrol antagonizes EGFR-dependent Erk1/2 activation in human androgen-independent prostate cancer cells with associated isozyme-selective PKC alpha inhibition . Invest New Drugs , 22 : 107 – 117 .
  • Stewart , J R , Ward , N E , Ioannides , C G and O'Brian , C A . 1999 . Resveratrol preferentially inhibits protein kinase C-catalyzed phosphorylation of a cofactor-independent, arginine-rich protein substrate by a novel mechanism . Biochemistry , 38 : 13244 – 13251 .
  • Woo , J H , Lim , J H , Kim , Y H , Suh , S I Min , D S . 2004 . Resveratrol inhibits phorbol myristate acetate-induced matrix metalloproteinase-9 expression by inhibiting JNK and PKC delta signal transduction . Oncogene , 23 : 1845 – 1853 .
  • Yu , R , Hebbar , V , Kim , D W , Mandlekar , S Pezzuto , J M . 2001 . Resveratrol inhibits phorbol ester and UV-induced activator protein 1 activation by interfering with mitogen-activated protein kinase pathways . Mol Pharmacol , 60 : 217 – 224 .
  • Zamin , L L , Dillenburg-Pilla , P , Argenta-Comiran , R , Horn , A P Simao , F . 2006 . Protective effect of resveratrol against oxygen-glucose deprivation in organotypic hippocampal slice cultures: involvement of PI3-K pathway . Neurobiol Dis , 24 : 170 – 182 .
  • Aggarwal , B B and Ichikawa , H . 2005 . Molecular targets and anticancer portential of indole-3-carbinol and its derivatives . Cell Cycle , 4 : 1201 – 1215 .
  • Chinni , S R and Sarkar , F H . 2002 . Akt inactivation is a key event in indole-3-carbinol-induced apoptosis in PC-3 cells . Clin Cancer Res , 8 : 1228 – 1236 .
  • Howells , L M , Gallacher-Horley , B , Houghton , C E , Manson , M M and Hudson , E A . 2002 . Indole-3-carbinol inhibits protein kinase B/Akt and induces apoptosis in the human breast tumor cell line MDA MB468 but not in the nontumorigenic HBL100 line . Mol Cancer Ther , 1 : 1161 – 1172 .
  • Li , Y , Li , X and Sarkar , F H . 2003 . Gene expression profiles of I3C- and DIM-treated PC3 human prostate cancer cells determined by cDNA microarray analysis . J Nutr , 133 : 1011 – 1019 .
  • Rahman , K M , Li , Y and Sarkar , F H . 2004 . Inactivation of akt and NF-kappaB play important roles during indole-3-carbinol-induced apoptosis in breast cancer cells . Nutr Cancer , 48 : 84 – 94 .
  • Duraj , J , Zazrivcova , K , Bodo , J , Sulikova , M and Sedlak , J . 2005 . Flavonoid quercetin, but not apigenin or luteolin, induced apoptosis in human myeloid leukemia cells and their resistant variants . Neoplasma , 52 : 273 – 279 .
  • Gouedard , C , Barouki , R and Morel , Y . 2004 . Dietary polyphenols increase paraoxonase 1 gene expression by an aryl hydrocarbon receptor-dependent mechanism . Mol Cell Biol , 24 : 5209 – 5222 .
  • Perez-Vizcaino , F , Duarte , J and Andriantsitohaina , R . 2006 . Endothelial function and cardiovascular disease: effects of quercetin and wine polyphenols . Free Radic Res , 40 : 1054 – 1065 .
  • Spencer , J P , Rice-Evans , C and Williams , R J . 2003 . Modulation of pro-survival Akt/protein kinase B and ERK1/2 signaling cascades by quercetin and its in vivo metabolites underlie their action on neuronal viability . J Biol Chem , 278 : 34783 – 34793 .
  • Huang , X , Chen , S , Xu , L , Liu , Y Deb , D K . 2005 . Genistein inhibits p38 map kinase activation, matrix metalloproteinase type 2, and cell invasion in human prostate epithelial cells . Cancer Res , 65 : 3470 – 3478 .
  • Li , Y and Sarkar , F H . 2002 . Inhibition of nuclear factor kappaB activation in PC3 cells by genistein is mediated via Akt signaling pathway . Clin Cancer Res , 8 : 2369 – 2377 .
  • Wang , J , Eltoum , I E and Lamartiniere , C A . 2004 . Genistein alters growth factor signaling in transgenic prostate model (TRAMP) . Mol Cell Endocrinol , 219 : 171 – 180 .
  • Acevedo-Duncan , M , Russell , C , Patel , S and Patel , R . 2004 . Aloe-emodin modulates PKC isozymes, inhibits proliferation, and induces apoptosis in U-373MG glioma cells . Int Immunopharmacol , 4 : 1775 – 1784 .
  • Huang , Q , Shen , H M and Ong , C N . 2004 . Inhibitory effect of emodin on tumor invasion through suppression of activator protein-1 and nuclear factor-kappaB . Biochem Pharmacol , 68 : 361 – 371 .
  • Kim , M S , Park , M J , Kim , S J , Lee , C H Yoo , H . 2005 . Emodin suppresses hyaluronic acid-induced MMP-9 secretion and invasion of glioma cells . Int J Oncol , 27 : 839 – 846 .
  • Lee , H Z , Hsu , S L , Liu , M C and Wu , C H . 2001 . Effects and mechanisms of aloe-emodin on cell death in human lung squamous cell carcinoma . Eur J Pharmacol , 431 : 287 – 295 .
  • Mijatovic , S , Maksimovic-Ivanic , D , Radovic , J , Miljkovic , D Kaludjerovic , G N . 2005 . Aloe emodin decreases the ERK-dependent anticancer activity of cisplatin . Cell Mol Life Sci , 62 : 1275 – 1282 .
  • Su , Y T , Chang , H L , Shyue , S K and Hsu , S L . 2005 . Emodin induces apoptosis in human lung adenocarcinoma cells through a reactive oxygen species-dependent mitochondrial signaling pathway . Biochem Pharmacol , 70 : 229 – 241 .
  • Zhou , X , Song , B , Jin , L , Hu , D Diao , C . 2006 . Isolation and inhibitory activity against ERK phosphorylation of hydroxyanthraquinones from rhubarb . Bioorg Med Chem Lett , 16 : 563 – 568 .
  • Ikeda , Y , Murakami , A and Ohigashi , H . 2005 . Ursolic acid promotes the release of macrophage migration inhibitory factor via ERK2 activation in resting mouse macrophages . Biochem Pharmacol , 70 : 1497 – 1505 .
  • Subbaramaiah , K , Michaluart , P , Sporn , M B and Dannenberg , A J . 2000 . Ursolic acid inhibits cyclooxygenase-2 transcription in human mammary epithelial cells . Cancer Res , 60 : 2399 – 2404 .
  • Shigeoka , Y , Igishi , T , Matsumoto , S , Nakanishi , H Kodani , M . 2004 . Sulindac sulfide and caffeic acid phenethyl ester suppress the motility of lung adenocarcinoma cells promoted by transforming growth factor-beta through Akt inhibition . J Cancer Res Clin Oncol , 130 : 146 – 152 .
  • Watabe , M , Hishikawa , K , Takayanagi , A , Shimizu , N and Nakaki , T . 2004 . Caffeic acid phenethyl ester induces apoptosis by inhibition of NFkappaB and activation of Fas in human breast cancer MCF-7 cells . J Biol Chem , 279 : 6017 – 6026 .
  • Zheng , Z S , Xue , G Z , Grunberger , D and Prystowsky , J H . 1995 . Caffeic acid phenethyl ester inhibits proliferation of human keratinocytes and interferes with the EGF regulation of ornithine decarboxylase . Oncol Res , 7 : 445 – 452 .
  • Hu , R , Khor , T O , Shen , G , Jeong , W S Hebbar , V . 2006 . Cancer chemoprevention of intestinal polyposis in ApcMin/+ mice by sulforaphane, a natural product derived from cruciferous vegetable . Carcinogenesis , 27 : 2038 – 2046 .
  • Keum , Y S , Owuor , E D , Kim , B R , Hu , R and Kong , A N . 2003 . Involvement of Nrf2 and JNK1 in the activation of antioxidant responsive element (ARE) by chemopreventive agent phenethyl isothiocyanate (PEITC) . Pharm Res , 20 : 1351 – 1356 .
  • Yu , R , Lei , W , Mandlekar , S , Weber , M J Der , C J . 1999 . Role of a mitogen-activated protein kinase pathway in the induction of phase II detoxifying enzymes by chemicals . J Biol Chem , 274 : 27545 – 27552 .
  • Yu , R , Mandlekar , S , Lei , W , Fahl , W E Tan , T H . 2000 . p38 mitogen-activated protein kinase negatively regulates the induction of phase II drug-metabolizing enzymes that detoxify carcinogens . J Biol Chem , 275 : 2322 – 2327 .
  • Liagre , B , Bertrand , J , Leger , D Y and Beneytout , J L . 2005 . Diosgenin, a plant steroid, induces apoptosis in COX-2 deficient K562 cells with activation of the p38 MAP kinase signalling and inhibition of NF-kappaB binding . Int J Mol Med , 16 : 1095 – 1101 .
  • Shishodia , S and Aggarwal , B B . 2006 . Diosgenin inhibits osteoclastogenesis, invasion, and proliferation through the downregulation of Akt, I kappa B kinase activation and NF-kappa B-regulated gene expression . Oncogene , 25 : 1463 – 1473 .
  • Jakubikova , J , Sedlak , J , Mithen , R and Bao , Y . 2005 . Role of PI3K/Akt and MEK/ERK signaling pathways in sulforaphane- and erucin-induced phase II enzymes and MRP2 transcription, G2/M arrest and cell death in Caco-2 cells . Biochem Pharmacol , 69 : 1543 – 1552 .
  • Xiao , D , Choi , S , Johnson , D E , Vogel , V G Johnson , C S . 2004 . Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-Jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2 . Oncogene , 23 : 5594 – 5606 .
  • Alsayed , Y , Uddin , S , Mahmud , N , Lekmine , F Kalvakolanu , D V . 2001 . Activation of Rac1 and the p38 mitogen-activated protein kinase pathway in response to all-trans-retinoic acid . J Biol Chem , 276 : 4012 – 4019 .
  • Bost , F , Caron , L , Marchetti , I , Dani , C Le Marchand-Brustel , Y . 2002 . Retinoic acid activation of the ERK pathway is required for embryonic stem cell commitment into the adipocyte lineage . Biochem J , 361 : 621 – 627 .
  • Fisher , G J , Talwar , H S , Lin , J , Lin , P McPhillips , F . 1998 . Retinoic acid inhibits induction of c-Jun protein by ultraviolet radiation that occurs subsequent to activation of mitogen-activated protein kinase pathways in human skin in vivo . J Clin Invest , 101 : 1432 – 1440 .
  • Gianni , M , Bauer , A , Garattini , E , Chambon , P and Rochette-Egly , C . 2002 . Phosphorylation by p38MAPK and recruitment of SUG-1 are required for RA-induced RAR gamma degradation and transactivation . EMBO J , 21 : 3760 – 3769 .
  • Kanungo , J , Potapova , I , Malbon , C C and Wang , H . 2000 . MEKK4 mediates differentiation in response to retinoic acid via activation of c-Jun N-terminal kinase in rat embryonal carcinoma P19 cells . J Biol Chem , 275 : 24032 – 24039 .
  • Sah , J F , Eckert , R L , Chandraratna , R A and Rorke , E A . Retinoids suppress epidermal growth factor-associated cell proliferation by inhibiting epidermal growth factor receptor-dependent ERK1/2 activation . J Biol Chem , 277 9728 – 9735 .
  • Singh , U S , Pan , J , Kao , Y L , Joshi , S Young , K L . 2003 . Tissue transglutaminase mediates activation of RhoA and MAP kinase pathways during retinoic acid-induced neuronal differentiation of SH-SY5Y cells . J Biol Chem , 278 : 391 – 399 .
  • Wang , H , Ikeda , S , Kanno , S , Guang , L M Ohnishi , M . 2001 . Activation of c-Jun amino-terminal kinase is required for retinoic acid-induced neural differentiation of P19 embryonal carcinoma cells . FEBS Lett , 503 : 91 – 96 .
  • Xu , Q , Konta , T , Furusu , A , Nakayama , K Lucio-Cazana , J . 2002 . Transcriptional induction of mitogen-activated protein kinase phosphatase 1 by retinoids. Selective roles of nuclear receptors and contribution to the antiapoptotic effect . J Biol Chem , 277 : 41693 – 41700 .
  • Yen , A , Roberson , M S , Varvayanis , S and Lee , A T . 1998 . Retinoic acid induced mitogen-activated protein (MAP)/extracellular signal-regulated kinase (ERK) kinase-dependent MAP kinase activation needed to elicit HL-60 cell differentiation and growth arrest . Cancer Res , 58 : 3163 – 3172 .
  • Gong , P , Hu , B and Cederbaum , A I . 2004 . Diallyl sulfide induces heme oxygenase-1 through MAPK pathway . Arch Biochem Biophys , 432 : 252 – 260 .
  • Knowles , L M and Milner , J A . 2003 . Diallyl disulfide induces ERK phosphorylation and alters gene expression profiles in human colon tumor cells . J Nutr , 133 : 2901 – 2906 .
  • Ruhl , R . 2005 . Induction of PXR-mediated metabolism by beta-carotene . Biochim Biophys Acta , 1740 : 162 – 169 .
  • Xiao , D , Choi , S , Lee , Y J and Singh , S V . 2005 . Role of mitogen-activated protein kinases in phenethyl isothiocyanate-induced apoptosis in human prostate cancer cells . Mol Carcinog , 43 : 130 – 140 .
  • Yu , R , Jiao , J J , Duh , J L , Tan , T H and Kong , A N . 1996 . Phenethyl isothiocyanate, a natural chemopreventive agent, activates c-Jun N-terminal kinase 1 . Cancer Res , 56 : 2954 – 2959 .
  • Chainy , G B , Manna , S K , Chaturvedi , M M and Aggarwal , B B . 2000 . Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-kappaB, AP-1, JNK, MAPKK and apoptosis . Oncogene , 19 : 2943 – 2950 .

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