Shifted concentration dependency of EpRE- and XRE-mediated gene expression points at monofunctional EpRE-mediated induction by flavonoids at physiologically relevant concentrations

Toxicology in Vitro

Volumn 22, Issue 4, 2008, Pages 921-926

  Lee Hilz, Yee Y ^a   ter Borg, Sovianne ^a   van Berkel, Willem J H ^a   Rietjens, Ivonne M C M ^a   Aarts, Jac M M J G ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

AhR; EpRE; Flavonoids; Monofunctional and bifunctional inducers; NQO1; XRE

Indexed keywords

3,3' DIHYDROXYFLAVONE; 3,3',4' TRIHYDROXYFLAVONE; ENZYME; FISETIN; FLAVONOID; FLAVONOL; QUERCETIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL LINE; DNA RESPONSIVE ELEMENT; ELECTROPHILE RESPONSIVE ELEMENT; ENHANCER REGION; GENE EXPRESSION; LIVER CELL CARCINOMA; MOUSE; NONHUMAN; XENOBIOTIC RESPONSIVE ELEMENT;

ANIMALS; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INDUCTION; FLAVONOIDS; GENE EXPRESSION REGULATION; GENES, REPORTER; LIVER NEOPLASMS; MICE; RESPONSE ELEMENTS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION, GENETIC; XENOBIOTICS;

EID: 41949111521     PISSN: 08872333     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tiv.2008.01.008     Document Type: Article

References (31)

1. Aarts J.M.M.J.G., Denison M.S., Cox M.A., Schalk M.A.C., Garrison P.M., Tullis K., de Haan L.H.J., and Brouwer A. Species-specific antagonism of Ah receptor action by 2,2′,5,5′-tetrachlorobiphenyl and 2,2′,3,3′,4,4′-hexachlorobiphenyl. European Journal of Pharmacology-Environmental Toxicology and Pharmacology Section 293 (1995) 463-474
2. Amakura Y., Tsutsumi T., Nakamura M., Kitagawa H., Fujino J., Sasaki K., Toyoda M., Yoshida T., and Maitani T. Activation of the aryl hydrocarbon receptor by some vegetable constituents determined using in vitro reporter gene assay. Biological and Pharmaceutical Bulletin 26 (2003) 532-539
3. Ashida H., Fukuda I., Yamashita T., and Kanazawa K. Flavones and flavonols at dietary levels inhibit a transformation of aryl hydrocarbon receptor induced by dioxin. FEBS Letters 476 (2000) 213-217
4. Boerboom A.M.J.F., Vermeulen M., van der Woude H., Bremer B.I., Lee-Hilz Y.Y., Kampman E., van Bladeren P.J., Rietjens I.M.C.M., and Aarts J.M.M.J.G. Newly constructed stable reporter cell lines for mechanistic studies on electrophile-responsive element-mediated gene expression reveal a role for flavonoid planarity. Biochemical Pharmacology 72 (2006) 217-226
5. CanivencLavier M.C., Bentejac M., Miller M.L., Leclerc J., Siess M.H., Latruffe N., and Suschetet M. Differential effects of non-hydroxylated flavonoids as inducers of cytochrome P450 1A and 2B isozymes in rat liver. Toxicology and Applied Pharmacology 136 (1996) 348-353
6. Ciolino H.P., Daschner P.J., and Yeh G.C. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochemical Journal 340 (1999) 715-722
7. Denison M.S., Fisher J.M., and Whitlock J.P. The DNA recognition site for the dioxin-Ah receptor complex - nucleotide-sequence and functional-analysis. Journal of Biological Chemistry 263 (1988) 17221-17224
8. Fahey J.F., and Stephenson K.K. Pinostrobin from honey and Thai ginger (Boesenbergia pandurata): a potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes. Journal of Agricultural and Food Chemistry 50 (2002) 7472-7476
9. Fahey J.W., Dinkova-Kostova A.T., Stephenson K.K., and Talalay P. The 'Prochaska' microtiter plate bioassay for inducers of NQO1. Quinones and Quinone Enzymes, Pt B 382 (2004) 243-258
10. Fresco P., Borges F., Diniz C., and Marques M.P.M. New insights on the anticancer properties of dietary polyphenols. Medicinal Research Reviews 26 (2006) 747-766
11. Hollman P.C.H., vanderGaag M., Mengelers M.J.B., vanTrijp J.M.P., deVries J.H., and Katan M.B. Absorption and disposition kinetics of the dietary antioxidant quercetin in man. Free Radical Biology and Medicine 21 (1996) 703-707
12. Jaiswal A.K. Human Nad(P)H-quinone oxidoreductase (Nqo1) gene structure and induction by dioxin. Biochemistry 30 (1991) 10647-10653
13. Kohle C., and Bock K.W. Activation of coupled Ah receptor and Nrf2 gene batteries by dietary phytochemicals in relation to chemoprevention. Biochemical Pharmacology 72 (2006) 795-805
14. Lee-Hilz Y.Y., Boerboom A.M.J.F., Westphal A.H., van Berkel W.J.H., Aarts J.M.M.J.G., and Rietjens I.M.C.M. Pro-oxidant activity of flavonoids induces EpRE-mediated gene expression. Chemical Research in Toxicology 19 (2006) 1499-1505
15. Lee-Hilz, Y.Y., Stolaki, M., van Berkel, W.J.H., Aarts, J.M.M.J.G., Rietjens, I.M.C.M., 2008. Activation of EpRE-mediated gene transcription by quercetin glucuronides depends on their deconjugation. Food and Chemical Toxicology, in press.
16. Lu Y.F., Santostefano M., Cunningham B.D.M., Threadgill M.D., and Safe S. Substituted flavones as aryl hydrocarbon (Ah) receptor agonists and antagonists. Biochemical Pharmacology 51 (1996) 1077-1087
17. Ma Q., Kinneer K., Bi Y.Y., Chan J.Y., and Kan Y.W. Induction of murine NAD(P)H:quinone oxidoreductase by 2,3,7,8-tetrachlorodibenzo-p-dioxin requires the CNC (cap 'n' collar) basic leucine zipper transcription factor Nrf2 (nuclear factor erythroid 2-related factor 2): cross-interaction between AhR (aryl hydrocarbon receptor) and Nrf2 signal transduction. Biochemical Journal 377 (2004) 205-213
18. Miao W.M., Hu L.G., Kandouz M., Hamilton D., and Batist G. A cell-based system to identify and characterize the molecular mechanism of drug-metabolizing enzyme (DME) modulators. Biochemical Pharmacology 67 (2004) 1897-1905
19. Miao W.M., Hu L.G., Scrivens P.J., and Batist G. Transcriptional regulation of NF-E2 p45-related factor (NRF2) expression by the aryl hydrocarbon receptor-xenobiotic response element signaling pathway - Direct cross-talk between phase I and II drug-metabolizing enzymes. Journal of Biological Chemistry 280 (2005) 20340-20348
20. Miranda C.L., Aponso G.L.M., Stevens J.F., Deinzer M.L., and Buhler D.R. Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Cancer Letters 149 (2000) 21-29
21. Myhrstad M.C.W., Carlsen H., Nordstrom O., Blomhoff R., and Moskaug J.O. Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter. Free Radical Biology and Medicine 32 (2002) 386-393
22. Nebert D.W., and Duffy J.J. How knockout mouse lines will be used to study the role of drug-metabolizing enzymes and their receptors during reproduction and development, and in environmental toxicity, cancer, and oxidative stress. Biochemical Pharmacology 53 (1997) 249-254
23. Olthof M.R., Hollman P.C.H., Vree T.B., and Katan M.B. Bioavailabilities of quercetin-3-glucoside and quercetin-4′-glucoside do not differ in humans. Journal of Nutrition 130 (2000) 1200-1203
24. Prochaska H.J., and Talalay P. Regulatory mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver. Cancer Research 48 (1988) 4776-4782
25. Rushmore T.H., and Pickett C.B. Transcriptional regulation of the rat glutathione S-transferase Ya subunit gene. Characterization of a xenobiotic-responsive element controlling inducible expression by phenolic antioxidants. Journal of Biological Chemistry 265 (1990) 14648-14653
26. Scalbert A., Manach C., Morand C., Remesy C., and Jimenez L. Dietary polyphenols and the prevention of diseases. Critical Reviews in Food Science and Nutrition 45 (2005) 287-306
27. Tutel'yan V.A., Gapparov M.M., Telegin L.Y., Devichenskii V.M., and Pevnitskii L.A. Flavonoids and resveratrol as regulators of Ah-receptor activity: protection from dioxin toxicity. Bulletin of Experimental Biology and Medicine 136 (2003) 533-539
28. Valerio L.G., Kepa J.K., Pickwell G.V., and Quattrochi L.C. Induction of human NAD(P)H: quinone oxidoreductase (NQO1) gene expression by the flavonol quercetin. Toxicology Letters 119 (2001) 49-57
29. Walle T., Otake Y., Brubaker J.A., Walle U.K., and Halushka P.V. Disposition and metabolism of the flavonoid chrysin in normal volunteers. British Journal of Clinical Pharmacology 51 (2001) 143-146
30. Yannai S., Day A.J., Williamson G., and Rhodes M.J.C. Characterization of flavonoids as monofunctional or bifunctional inducers of quinone reductase in murine hepatoma cell lines. Food and Chemical Toxicology 36 (1998) 623-630
31. Yueh M.-F., and Tukey R.H. Nrf2-Keap1 signaling pathway regulates human UGT1A1 expression in vitro and in transgenic UGT1 mice. Journal Biological Chemistry 282 (2007) 8749-8758