Electrophilic and Reactive Oxygen Species Detoxification Potentials of Chalcone Dimers is Mediated by Redox Transcription Factor Nrf-2

Journal of Biochemical and Molecular Toxicology

Volumn 28, Issue 1, 2014, Pages 11-22

  Ajiboye, Taofeek O ^a   Yakubu, Musa T ^b   Oladiji, Adenike T ^b  

^a AL HIKMAH UNIVERSITY   (Nigeria)

^b UNIVERSITY OF ILORIN   (Nigeria)

Author keywords

Chalcone Dimers; Free Radicals and Electrophile Detoxifying Enzymes; Keap 1; Lophirone B; Lophirone C; Nrf2; Reactive Oxygen Species

Indexed keywords

CATALASE; CHALCONE DERIVATIVE; CHALCONE DIMER; EPOXIDE HYDROLASE; GLUCURONOSYLTRANSFERASE; GLUTATHIONE PEROXIDASE; GLUTATHIONE REDUCTASE; GLUTATHIONE TRANSFERASE; IOPHIRONE B; IOPHIRONE C; KELCH LIKE ECH ASSOCIATED PROTEIN 1; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIDOREDUCTASE; POLYPHENOL DERIVATIVE; QUINONE OXIDOREDUCTASE 1; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BARK; CELL FRACTIONATION; CELL PROTECTION; CONTROLLED STUDY; CYTOPLASM; DETOXIFICATION; DRUG EFFECT; ELECTROPHILICITY; ENZYME ACTIVITY; LIVER; LIVER MICROSOME; LOPHIRA ALATA; MALE; MEDIATOR; MEDICINAL PLANT; NONHUMAN; OXIDATION REDUCTION STATE; PLANT STEM; PROTEIN EXPRESSION; PROTEIN FUNCTION; RAT;

RATTUS;

CHALCONE DIMERS; FREE RADICALS AND ELECTROPHILE DETOXIFYING ENZYMES; KEAP-1; LOPHIRONE B; LOPHIRONE C; NRF2; REACTIVE OXYGEN SPECIES;

ANIMALS; BLOTTING, WESTERN; CHALCONES; DIMERIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MALE; METABOLIC DETOXICATION, DRUG; NF-E2-RELATED FACTOR 2; OXIDATION-REDUCTION; RATS; RATS, WISTAR; REACTIVE OXYGEN SPECIES;

EID: 84891635639     PISSN: 10956670     EISSN: 10990461     Source Type: Journal    
DOI: 10.1002/jbt.21517     Document Type: Article

References (36)

1. Talalay P. Chemoprotection against cancer by induction of phase 2 enzymes. Biofactors 2000;12:5-11.
2. Hayes JD, McMahon M. Molecular basis for the contribution of the antioxidant responsive element to cancer chemo- prevention. Cancer Lett 2001;174:103-113.
3. Zhang DD. Mechanistic studies of the Nrf2-Keap1 signaling pathway. Drug Metab Rev 2006;38:769-789.
4. Giudice A, Montella M. Activation of the Nrf2-ARE signaling pathway: a promising strategy in cancer prevention. Bioessays 2006;28:169-181.
5. Chen C, Kong AN. Dietary cancer-chemopreventive compounds: from signaling and gene expression to pharmacological effects. Trends Pharmacol Sci 2005;26:318-326.
6. Lee JS, Surh YJ. Nrf2 as a novel molecular target for chemoprevention. Cancer Lett 2005;224:171-84.
7. Dinkova-Kostova AT, Massiah MA, Bozak RE, Hicks RJ, Talalay P. Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc Natl Acad Sci U S A 2001;98:3404-3409.
8. Go ML, Wu X, Liu XL. Chalcones: an update on cytotoxic and chemoprotective properties. Curr Med Chem 2005;12(4):481-499.
9. Persinos GJ, Quimby MW. Studies on Nigerian Plants V. Comparative Anatomy of Lophira lanceolata and Lophira alata. Econ Bot 1968;22:206-220.
10. Pegnyemb DE, Messanga BB, Ghogomu R, Sondengam BL. Martin MT, Bodo B. A new benzoylglucoside and a new prenylated isoflavone from Lophira lanceolata. J Nat Prod 1998; 61:801-803.
11. Persinos GJ, Quimby MW, Mott AR, Farnsworth NR, Abraham DJ, Fong HHS, Blomster RN. Studies on Nigerian plants. 3. Biological and phytochemical screening of Lophira lanceolata, and the isolation of benzamide. Planta Med 1967;15(4):361-365.
12. Ghogomu RT, Sondengam BL, Martin MT, Bodo B. Structure of lophirones B and C from the stem bark of Lophira lanceolata. Phytochemistry 1989;28(5):1557-1559.
13. Ghogomu RT, Sondengam BL, Martin MT, Bodo B. Structure of chalcone dimers lophirone F, H and I from Lophira lanceolata stem bark. Phytochemistry 1990;29:2289.
14. Murakami A, Tanaka S, Ohigashi H, Hirota M, Irie R, Takeda N, Tatematsu A, Koshimizu K. Chalcone tetramers, lophirachalcone and alatachalcone, from Lophira alata as possible anti-tumor promoters. Biosci Biotechnol Biochem 1992;56(5):769-772.
15. Ajiboye TO, Yakubu MT, Oladiji AT. Electrophilic, free radical, reactive oxygen species and detoxification potentials of Lophira alata. Free Radicals & Antioxidants 2011;3(1):40-47.
16. National Research Council. Guide for the Care and Use of Laboratory Animals. National Academies Science Press, 8th edition.; 2011. 161-196.
17. World Health Organization. Basic OECD principles of GLP. Geneva, Switzerland: World Health Organization; 1998. Available at: www.who.int/tdrold/publications/publications/pdf/pr15/info.pdf. Access date: 24-08-09.
18. Kondraganti SR, Muthiah K, Jiang W, Barrios R, Moorthy B. Effects of 3-methylcholanthrene on gene expression profiling in the rat using cDNA microarray analyses. Chem Res Toxicol 2005;18:1634-1641.
19. Misra HP, Fridovich I. The role of superoxide anion in the autoxidation of epinephrine and a simple assay for superoxide dismutase. J Biol Chem 1972;247:3170-3175.
20. Beers RF Jr, Sizer IW. A spectrophotometric method for measuring breakdown of hydrogen peroxide by catalase. J Biol Chem 1952;195:133-140.
21. Rotruck JT, Pope AL, Ganther HF, Swason AB. Selenium: biochemical role as a component of glutathione peroxidase. Science 1973;179:588-590.
22. Mavis RD, Stellwagen E. Purification and subunit structure of glutathione reductase from bakers yeast. J Biol Chem 1968;243:809-814.
23. Habig WH, Pabst MJ, Jakoby WB. Glutathione S-transferase. J Biol Chem 1974;249:7130-7139.
24. Jaiswal AK, McBride OW, Adesnik M, Nebert DW. Human dioxin-inducible cytosolic NAD(P)H: menadione oxidoreductase. cDNA sequence and localization of gene to chromosome. J Biol Chem 1988;263:13572-13578.
25. Bock KW, Burchell B, Dutton GJ, Hanninen O, Mulder GJ, Owens IS, Siest G, Tephly TR. UDP-glucuronyl transferase activities: guidelines for consistent interim terminology and assay conditions. Biochem Pharmacol 1983;32:953-955.
26. Depierre JW, Seidegard J, Morgenstern R, Balk L, Meijer J, Astrom A, Norelius I, Ernster L. Induction of cytosolic glutathione transferase and microsomal epoxide hydrolase activities in extrahepatic organs of the rat by phenobarbital, 3-methylcholanthrene and trans-stilbene oxide. Xenobiotica 1984;14:295-301.
27. Alam J, Cook JL. Transcriptional regulation of the hemeoxygenase-1 gene via the stress response element pathway. Curr Pharm Des 2003;9:2499-2511.
28. Talalay P, Fahey JW. Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism. J Nutr 2001;131:3027S-3033S.
29. Kensler TW, Wakabayashi N, Biswal S. Cell survival responses to environmental stresses via the Keap1-2- ARE pathway. Annu Rev Pharmacol Toxicol 2007;47:89-116.
30. Kobayashi M, Yamamoto M. Nrf2-1 regulation of cellular defense mechanisms against electrophiles and reactive oxygen species. Adv Enzyme Regul 2006;46:113-140.
31. Dinkova-Kostova AT, Holtzclaw WD, Cole RN, Itoh K, Wakabayashi N, Katoh Y, Yamamoto M, Talalay P. Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proceedings of the National Academy of Science USA 2002;99:11908-11913.
32. Surh YJ. Cancer chemoprevention with dietary phytochemicals. Nat Rev Cancer 2003;3:768-780.
33. Eggler AL, Gay KA, Mesecar AD. Molecular mechanisms of natural products in chemoprevention: induction of cytoprotective enzymes by Nrf2. Mol Nutr Food Res 2008;52:S84-S94.
34. Dinkova-Kostova AT, Talalay P. irect and indirect antioxidant properties of inducers of cytoprotective proteins. Mol Nutr Food Res 2008;52:128-138.
35. Surh YJ, Kundu JK, Na HK, Lee JS. Redox-sensitive transcription factors as prime targets for chemoprevention with anti-inflammatory and antioxidative phytochemicals. J Nutr 2005;135:2993S-3001S.
36. Ajiboye TO, Salau AK, Yakubu MT, Oladiji AT, Akanji MA, Okogun JI. Acetaminophen perturbed redox homeostasis in Wistar rat liver: protective role of aqueous Pterocarpus osun leaf extract. Drug Chem Toxicol 2010;33 (1):77-87.