Baicalin induces NAD(P)H:quinone reductase through the transactivation of AP-1 and NF-κB in Hepa 1c1c7 cells

European Journal of Cancer Prevention

Volumn 13, Issue 6, 2004, Pages 521-528

  Park, H J ^a   Lee, Y W ^b   Lee, S K ^a  

^a Ewha Womans University   (South Korea)

^b UNIVERSITY OF KENTUCKY MEDICAL CENTER   (United States)

Author keywords

AP 1; Baicalin; Chemoprevention; NF B; Quinone reductase (QR)

Indexed keywords

ANTIOXIDANT; BAICALIN; CHLORAMPHENICOL ACETYLTRANSFERASE; ELECTROPHILE RESPONSE ELEMENT; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); TRANSCRIPTION FACTOR AP 1; UNCLASSIFIED DRUG; XENOBIOTIC AGENT;

ANIMAL CELL; ARTICLE; BINDING SITE; CANCER PREVENTION; CELL LINE; CONTROLLED STUDY; DNA FLANKING REGION; DRUG EFFECT; DRUG MECHANISM; GEL MOBILITY SHIFT ASSAY; GENE EXPRESSION; GENETIC TRANSFECTION; HEPATOMA CELL; LIVER CELL; MOUSE; NONHUMAN; PLASMID; PRIORITY JOURNAL; REPORTER GENE; TRANSACTIVATION;

CARCINOMA, HEPATOCELLULAR; CHEMOPREVENTION; ELECTROPHORETIC MOBILITY SHIFT ASSAY; ENZYME INDUCTION; ENZYME INHIBITORS; FLAVONOIDS; GENE EXPRESSION REGULATION; HUMANS; LIVER NEOPLASMS; NAD(P)H DEHYDROGENASE (QUINONE); TUMOR CELLS, CULTURED;

EID: 10244242487     PISSN: 09598278     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008469-200412000-00010     Document Type: Article

References (47)

1. Angel P, Karin M (1991). The role of Jun, Fos and the AP-1 complex in cell-proliferation and transformation. Biochim Biophys Acta 1072: 129-157.
2. Ares JJ, Outt PE, Randall JL, et al. (1995). Synthesis and biological evaluation of substituted flavones as gastroprotective agents. J Med Chem 38: 4937-4943.
3. Baeuerle PA, Baltimore D (1988). I kappa B: a specific inhibitor of the NF-kappa B transcription factor. Science 242: 540-546.
4. Baeuerle PA, Baltimore D (1989). A 65-kappa D subunit of active NF-kappaB is required for inhibition of NF-kappaB by I kappaB. Genes Dev 3: 1689-1698.
5. Beg AA, Finco TS, Nanterment PV, et al. (1993). Tumor necrosis factor and interleukin-1 lead to phosphorylation and loss of Ikappa B alpha: a mechanism for NF-kappa B activation. Mol Cell Biol 13: 3301-3310.
6. Bradford MM (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254.
7. Chan SC, Chang YS, Wang JP, et al. (1998). Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta Med 64: 153-158.
8. Cheng LC, Gerhauser C, Song LL, et al. (1997). Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase. J Natl Prod 60: 869-873.
9. Curran T, Franza BR (1988). Fos and Jun: the AP-1 connection. Cell 55: 395-397.
10. De Martin R, Hoeth M, Hofer-Warbinex R, et al. (2000). The transcription factor NF-kappa B and the regulation of vascular cell function. Arterioscler Thromb Vasc Biol 20: E83-E88.
11. De Meyer N, Haemers A, Mishra L, et al. (1991). 4′-Hydroxy-3- methoxyflavones with potent antipicornavirus activity. J Med Chem 34: 736-746.
12. Dhakshinamoorthy S, Jaiswal AK (2001). Functional characterization and role of INrf2 in antioxidant response element-mediated expression and antioxidant induction of NAD(P)H: quinone oxidoreductasel gene. Oncogene 20: 3906-3917.
13. Favreau LV, Pickett CB (1991). Transcriptional regulation of the rat NAD(P)H: quinone reductase gene. Identification of regulatory elements controlling basal level expression and inducible expression by planar aromatic compounds and phenolic antioxidants. J Biol Chem 266: 4556-4561.
14. Ferriola PC, Cody V, Middleton E Jr (1989). Protein kinase C inhibition by plant flavonoids. Kinetic mechanisms and structure-activity relationships. Biochem Pharmacol 38: 1617-1624.
15. Friling RS, Bensimon A, Tichauer Y, et al. (1990). Xenobiotic-inducible expression of murine glutathione S-transferase Ya subunit gene is controlled by an electrophile-responsive element. Proc Natl Acad Sci USA 87: 6258-6262.
16. Gorman CM, Moffat LF, Howard BH (1982). Recombinant genomes which express chloramphenicol acetyltransferase in mammalian cells. Mol Cell Biol 2: 1044-1051.
17. Havsteen B (1983). Flavonoids, a class of natural products of high pharmacological potency. Biochem Pharmacol 32: 1141-1148.
18. Huang MT, Miwa GT, Cronheim N (1979). Rat liver cytosolic azoreductase. Electron transport properties and the mechanism of dicumarol inhibition of the purified enzyme. J Biol Chem 254: 11223-11227.
19. Huang X, Tu CHL, Zhang LX et al. (1987). In: Huang X (editor): Immunopharmacology, Shanghai: Shanghai Science and Technology Press; pp. 159-160.
20. Itoh K, Chiba T, Takahashi S, et al. (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.
21. Jaiswal AK, Venugopal R (1996). Nrf1 and Nrf2 positively and c-Fos and Fra1 negatively regulate the human antioxidant response element-mediated expression of NAD(P)H:quinone oxidoreductase1 gene. Proc Natl Acad Sci USA 93: 14960-14965.
22. Jaiswal AK, Venugopal R (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.
23. Jeon YJ, Han SH, Lee YW, et al. (1998). Inhibition of NF-kB/Rel nuclear translocation by dexamethasone: mechanism for the inhibition of iNOS gene expression. Biochem Mol Biol Int 45: 435-441.
24. Kang-Shen Y, Peter JO (1995). Involvement of NF-κB in the induction of NAD(P)H: Quinone oxidoreductase (DT-diaphorase) by hypoxia, oltipraz and mytomycin C. Biochem Pharmacol 49: 275-282.
25. Kataoka K, Noda M, Nishizawa M (1994). Maf nuclear oncoprotein recognizes sequences related to an AP-1 site and forms heterodimers with both Fos and Jun. Mol Cell Biol 14: 700-712.
26. Kennelly EJ, Gerhauser C, Song LL, et al. (1997). Induction of quinone reductase by anolides isolated from Physalis philadelphica (tomatillos). J Agric Food Chem 45: 3771-3777.
27. Kubo M, Asano T, Shiomoto H, Matsuda H (1994). Studies on rehmanniae radix. I. Effect of 50% ethanolic extract from steamed and dried rehmanniae radix on hemorheology in arthritic and thrombosic rats. Biol Pharm Bull 17: 1282-1286.
28. Kuo SM (1997). Dietary flavonoid and cancer prevention: evidence and potential mechanism. Crit Rev Oncog 8: 47-69.
29. Kwak MK, Itoh K, Yamamoto M, et al. (2001). Role of transcription factor Nrf2 in the induction of hepatic phase 2 and antioxidative enzymes in vivo by the cancer chemoprotective agent, 3H-1,2-dimethiole-3-thione. Mol Med 7: 135-145.
30. Leibovitz BE, Mueller JA (1993). Bioflavonoids and polyphenols: medical application. J Optima Nutr 2: 17-35.
31. Li Y, Jaiswal AK (1992). Regulation of human NAD(P)H:quinone oxidoreductase gene. Role of AP1 binding site contained within human antioxidant response element. J Biol Chem 267: 15097-15104.
32. Lind C (1985). Relationship between the rate of reduction of benzo(a)pyrene-3, 6-quinone and the formation of benzo(a)pyrene-3,6-quinol glucuronides in rat liver microsomes. Biochem Pharmacol 34: 895-897.
33. McMahon M, Itoh K, Yamamoto M, et al. (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.
34. Mehta RG, Liu J, Constantinou A, et al. (1995). Cancer chemopreventive activity of brassinin, a phytoalexin from cabbage. Carcinogenesis 16: 399-404.
35. 2 and antioxidants have opposite effects on activation of NF-kappa B and AP-1 in intact cells: AP-1 as secondary antioxidant-responsive factor. EMBO J 12: 2005-2015.
36. Morimitsu Y, Nakagawa Y, Hayashi K, et al. (2002). A sulforaphane analogue that potently activates the Nrf2-dependent detoxification pathway. J Biol Chem 277: 3456-3463.
37. Park HJ, Lee YW, Park HH, et al. (1998). Induction of quinone reductase by a methanol extract of Scutellaria baicalensis and its flavonoids in murine Hepa 1c1c7 cells. Eur J Cancer Prev 7: 465-471.
38. Prestera T, Holtzclaw WD, Zhang Y, et al. (1993). Chemical and molecular regulation of enzymes that detoxify carcinogens. Proc Natl Acad Sci USA 90: 2965-2969.
39. Rushmore TH, Pickett CB (1990). Transcriptional regulation of the rat glutathione S-transferase Ya subunit gene. Characterization of a xenobiotic-responsive element controlling inducible expression by phenolic antioxidants. J Biol Chem 265: 14648-14653.
40. Rushmore TH, King RG, Paulson KE, et al. (1990). Regulation of glutathione S-transferase Ya subunit gene expression: identification of a unique xenobiotic-responsive element controlling inducible expression by planar aromatic compounds. Proc Natl Acad Sci USA 87: 3826-3830.
41. Rushmore TH, Morton MR, Pickett CB (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.
42. Sen R, Baltimore D (1986). Inducibility of κ immunoglobulin enhancer-binding protein NF-κB by a post-translational mechanism. Cell 47: 921-928.
43. Song LL, Kosmeder JW II, Lee SK, et al. (1999). Cancer chemopreventive activity mediated by 4′-bromoflavone, a potent inducer of phase II detoxification enzymes. Cancer Res 59: 578-585.
44. Talalay P, Benson AM (1982). Elevation of quinone reductase activity by anticarcinogenic antioxidants. Adv Enzyme Regul 20: 287-300.
45. Wall ME, Wani MC, Manikumar G, et al. (1988). Plant antimutagenic agents, 2. Flavonoids. J Nat Prod 51: 1084-1091.
46. Yamashita Y, Kawada S, Nakano H (1990). Induction of mammalian topoisomerase II dependent DNA cleavage by nonintercalative flavonoids, genistein and orobol. Biochem Pharmacol 39: 737-744.
47. Zhang Y, Kensler TW, Cho CG, et al. (1994). Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci USA 91: 3147-3150.