Nuclear factor E2-related factor 2-mediated induction of NAD(P)H:Quinone oxidoreductase 1 by 3,5-dimethoxy-trans-stilbene

Journal of Pharmacological Sciences

Volumn 116, Issue 1, 2011, Pages 89-96

  Park, Eun Jung ^a   Min, Hye Young ^a   Park, Hyen Joo ^b   Chung, Hwa Jin ^b   Ahn, Yong Hyun ^c   Pyee, Jae Ho ^c   Lee, Sang Kook ^b  

^a Ewha Womans University   (South Korea)

^b Seoul National University   (South Korea)

^c Dankook University   (South Korea)

Author keywords

3,5 dimethoxy trans stilbene (DMS); Heme oxygenase (HO 1); NAD(P)H:quinone oxidoreductase 1 (NQO1); Nuclear factor E2 related factor 2 (Nrf2); Protein kinase C (PKC )

Indexed keywords

3,5 DIMETHOXYSTILBENE; BETA ACTIN; HEME OXYGENASE 1; MESSENGER RNA; PINOSYLVIN; PROTEIN KINASE C DELTA; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE) 1; STILBENE DERIVATIVE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INDUCTION; HEPATOMA CELL; MOUSE; NONHUMAN; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN SYNTHESIS REGULATION; PROTEIN TRANSPORT; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SIGNAL TRANSDUCTION; UPREGULATION; WESTERN BLOTTING;

EID: 79956204372     PISSN: 13478613     EISSN: 13478648     Source Type: Journal    
DOI: 10.1254/jphs.11024FP     Document Type: Article

References (30)

1. Pitot HC, Dragan YP. Facts and theories concerning the mechanisms of carcinogenesis. FASEB J. 1991;5:2280-2286. (Pubitemid 21892904)
2. Chen C, Kong AN. Dietary chemopreventive compounds and ARE/EpRE signaling. Free Radic Biol Med. 2004;36:1505-1516. (Pubitemid 38746559)
3. Nioi P, Hayes JD. Contribution of NAD(P)H:quinone oxidoreductase 1 to protection against carcinogenesis, and regulation of its gene by the Nrf2 basic-region leucine zipper and the aryl-hydrocarbon receptor basic helix-loop-helix transcription factors. Mutat Res. 2004;555:149-171. (Pubitemid 39359178)
4. Cuendet M, Oteham CP, Moon RC, Pezzuto JM. Quinone reductase induction as a biomarker for cancer chemoprevention. J Nat Prod. 2006;69:460-463.
5. Rushmore TH, Morton MR, Pickett CB. The antioxidant responsive element. Activation by oxidative stress and identification of the DNA consensus sequence required for functional activity. J Biol Chem. 1991;266:11632-11639. (Pubitemid 21906996)
6. Bloom DA, Jaiswal AK. 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. 2003;278:44675-44682. (Pubitemid 37377224)
7. Lu Z, Liu D, Hornia A, Devonish W, Pagano M, Foster DA. Activation of protein kinase C triggers its ubiquitination and degradation. Mol Cell Biol. 1998;18:839-845. (Pubitemid 28063417)
8. Jorgensen E. The formation of pinosylvin and its monomethyl ether in the sapwood of Pinus resinosa ait. Can J Botany. 1961; 39:1765-1772.
9. 2 production in lipopolysaccharide-induced mouse macrophage cells. Bioorg Med Chem Lett. 2004;14:5895-5898.
10. Perecko T, Jancinova V, Drabikova K, Nosal R, Harmatha J. Structure-efficiency relationship in derivatives of stilbene. Comparison of resveratrol, pinosylvin and pterostilbene. Neuro Endocrinol Lett. 2008;29:802-805.
11. Lee J, Jung E, Lim J, Lee J, Hur S, Kim SS, et al. Involvement of nuclear factor-kappaB in the inhibition of pro-inflammatory mediators by pinosylvin. Planta Med. 2006;72:801-806. (Pubitemid 44204642)
12. Prochaska HJ, De Long MJ, Talalay P. On the mechanisms of induction of cancer-protective enzymes: a unifying proposal. Proc Natl Acad Sci U S A. 1985;82:8232-8236. (Pubitemid 16171068)
13. Prochaska HJ, Santamaria AB. Direct measurement of NAD(P) H:quinone reductase from cells cultured in microtiter wells: a screening assay for anticarcinogenic enzyme inducers. Anal Biochem. 1988;169:328-336. (Pubitemid 18081406)
14. Smith PK, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, et al. Measurement of protein using bicin-choninic acid. Anal Biochem. 1985;150:76-85. (Pubitemid 16258399)
15. Abramoff MD, Magelhaes PJ, Ram SJ. Image processing with ImageJ. Biophotonics International. 2004;11:36-42.
16. Chomczynski P, Sacchi N. Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal Biochem. 1987;162:156-159. (Pubitemid 17064313)
17. Wang TT. β-Naphthoflavone, an inducer of xenobiotic metabolizing enzymes, inhibits firefly luciferase activity. Anal Biochem. 2002;304:122-126.
18. Griner EM, Kazanietz MG. Protein kinase C and other diacylglycerol effectors in cancer. Nat Rev Cancer. 2007;7:281-294. (Pubitemid 46480971)
19. Dinkova-Kostova AT, Talalay P. NAD(P)H:quinone acceptor oxidoreductase 1 (NQO1), a multifunctional antioxidant enzyme and exceptionally versatile cytoprotector. Arch Biochem Biophys. 2010;501:116-123.
20. Iskander K, Li J, Han S, Zheng B, Jaiswal AK. NQO1 and NQO2 regulation of humoral immunity and autoimmunity. J Biol Chem. 2006;281:30917-30924. (Pubitemid 44582146)
21. Zhang Y, Kensler TW, Cho CG, Posner GH, Talalay P. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci U S A. 1994;91:3147-3150. (Pubitemid 24130192)
22. Perez JL, Jayaprakasha GK, Cadena A, Martinez E, Ahmad H, Patil BS. In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids. BMC Complement Altern Med. 2010;10:51.
23. Montano MM, Chaplin LJ, Deng H, Mesia-Vela S, Gaikwad N, Zahid M, et al. Protective roles of quinone reductase and tamoxifen against estrogen-induced mammary tumorigenesis. Oncogene. 2007;26:3587-3590. (Pubitemid 46816762)
24. Gao J, Kashfi K, Liu X, Rigas B. NO-donating aspirin induces phase II enzymes in vitro and in vivo. Carcinogenesis. 2006;27: 803-810.
25. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, et al. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science. 1997;275:218-220. (Pubitemid 127696281)
26. Heo YH, Kim S, Park JE, Jeong LS, Lee SK. Induction of quinone reductase activity by stilbene analogs in mouse Hepa 1c1c7 cells. Arch Pharm Res. 2001;24:597-600. (Pubitemid 33644620)
27. Zhang W, Go ML. Quinone reductase induction activity of methoxylated analogues of resveratrol. Eur J Med Chem. 2007;42:841-850. (Pubitemid 46810071)
28. Szekeres T, Saiko P, Fritzer-Szekeres M, Djavan B, Jäger W. Chemopreventive effects of resveratrol and resveratrol derivatives. Ann N Y Acad Sci. 2011;1215:89-95.
29. Itoh K, Wakabayashi N, Katoh Y, Ishii T, Igarashi K, Engel JD, et al. Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain. Genes Dev. 1999;13:76-86. (Pubitemid 29045117)
30. Ramos-Gomez M, Kwak MK, Dolan PM, Itoh K, Yamamoto M, Talalay P, et al. Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in nrf2 transcription factor-deficient mice. Proc Natl Acad Sci U S A. 2001;98:3410-3415. (Pubitemid 32220859)