3,5,7,3′,4′-Pentamethoxyflavone, a quercetin derivative protects DNA from oxidative challenges: Potential mechanism of action

Journal of Photochemistry and Photobiology B: Biology

Volumn 131, Issue , 2014, Pages 96-103

  Jakhar, Rekha ^a   Paul, Souren ^a   Park, Young Rong ^b   Han, Jaehong ^b   Kang, Sun Chul ^a  

^a Daegu University   (South Korea)

^b Chung Ang University   (South Korea)

Author keywords

Antioxidant; Comet assay; DNA binding; DNA damage; ROS

Indexed keywords

3,5,7,3',4' PENTAMETHOXYFLAVONE; ANTIOXIDANT; DNA; PLANT EXTRACT; QUERCETIN DERIVATIVE; UNCLASSIFIED DRUG; 2,2'-AZINO-DI-(3-ETHYLBENZOTHIAZOLINE)-6-SULFONIC ACID; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; 3,5,7,3',4'-PENTAMETHOXYFLAVONE; BENZOTHIAZOLE DERIVATIVE; BIPHENYL DERIVATIVE; FLAVONE DERIVATIVE; NITRIC OXIDE; PICRIC ACID; PROTECTIVE AGENT; SCAVENGER; SULFONIC ACID DERIVATIVE;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING ASSAY; CELL ASSAY; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; DNA DAMAGE; DNA PROTECTION; DRUG ISOLATION; DRUG MECHANISM; KAEMPERIA PARVIFLORA; MACROPHAGE; MEDICINAL PLANT; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; ANIMAL; CELL CULTURE; CELL SURVIVAL; CHEMISTRY; COMET ASSAY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; MOUSE; TOXICITY TESTING; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; ANTIOXIDANTS; BENZOTHIAZOLES; BIPHENYL COMPOUNDS; CELL SURVIVAL; CELLS, CULTURED; COMET ASSAY; DNA; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; FLAVONES; FREE RADICAL SCAVENGERS; MICE; NITRIC OXIDE; PICRATES; PROTECTIVE AGENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFONIC ACIDS; TOXICITY TESTS;

EID: 84893701521     PISSN: 10111344     EISSN: 18732682     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2014.01.003     Document Type: Article

References (53)

1. J.H. Cho, J.G. Lee, Y.I. Yang, J.H. Kim, J.H. Ahn, N.I. Baek, K.T. Lee, and J.H. Choi Eupatilin, a dietary flavonoid, induces G2/M cell cycle arrest in human endometrial cancer cells Food Chem. Toxicol. 49 2011 1737 1744
2. M. Mamani-Matsuda, T. Kauss, A. Al-Kharrat, J. Rambert, F. Fawaz, D. Thiolat, D. Moynet, S. Coves, D. Malvy, and M.D. Mossalayi Therapeutic and preventive properties of quercetin in experimental arthritis correlate with decreased macrophage inflammatory mediators Biochem. Pharmacol. 72 2006 1304 1310
3. L. Mira, M. Silva, R. Rocha, and C.F. Manso Measurement of relative antioxidant activity of compounds: a methodological note Redox. Rep. 4 1999 69 74
4. L. Mira, M.T. Fernandez, M. Santos, R. Rocha, M.H. Florêncioand, and K.R. Jennings Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity Free Radic. Res. 36 2002 1199 1208
5. J.S.F. Swaran Structural, chemical and biological aspects of antioxidants for strategies against metal and metalloid exposure Oxid. Med. Cell Longev. 2 2009 191 206
6. C.K.B. Ferrari Free radicals, lipid peroxidation and antioxidants in apoptosis: implications in cancer, cardiovascular and neurological diseases Biologia 55 2000 581 590
7. K. Rahman Studies on free radicals, antioxidants, and co-factors Clin. Interv. Aging. 2 2007 219 236
8. M.M. Silva, M. Santos, G. Caroc, O.G. Rocha, G. Justino, and L. Mira Chalcone 3-hydroxylation is not a general property of flavonoid 3'-hydroxylase Free Radic. Res. 36 2002 1219 1227
9. N. Russo, M. Toscano, and N. Uccella Semiempirical molecular modeling into quercetin reactive site: structural, conformational, and electronic features J. Agric. Food Chem. 8 2000 3232 3237
10. P.G. Pietta Flavonoids as antioxidants J. Nat. Prod. 63 2000 1035 1042
11. Z. Zhu, C. Li, and N.Q. Li Electrochemical study of quercetin interacting with DNA Microchem. J. 71 2002 57
12. D. Ziecha, R. Francob, A. Pappac, and M.I. Panayiotidisd Reactive Oxygen Species (ROS) - Induced genetic and epigenetic alterations in human carcinogenesis Mutat Res. 711 2011 167 173
13. J. Tan, B. Wang, and L. Zhu DNA binding and oxidative DNA damage induced by a quercetin copper (II) complex J. Biol. Inorg. Chem. 14 2009 727 739
14. G. Rusak, I. Piantanida, L. Masic, K. Kapuralin, K. Durgo, and N. Kopjar Spectrophotometric analysis of flavonoids-DNA interactions and DNA damaging/protecting and cytotoxic potential of flavonoids in human peripheral blood lymphocytes Chem-Biol, Interact. 188 2010 181 189
15. E.H. Liu, L.W. Qi, and P. Li Structural relationship and binding mechanisms of five flavonoids with bovine serum albumin Molecules 15 2010 9092 9103
16. K. Sutthanut, B. Sripanidkulchai, C. Yenjai, and M. Jay Simultaneous identification and quantitation of 11 flavonoid constituents in Kaempferia parviflora by gas chromatography J. Chromatogr. A. 1143 2007 227 233
17. N. Wongsrikaew, H.C. Woo, K. Vichitphan, and J. Han Supercritical CO2 for efficient extraction of polymethoxyflavones in Kaempferia Parvifloraz J. Korean Soc. Appl. Biol. Chem. 54 2011 1008 1011
18. A. Russo, R. Acquaviva, A. Campisi, V. Sorrenti, C. Di Giacomo, G. Virgata, M.L. Barcellona, and A. Vanella Bioflavonoids as antiradicals, antioxidants and DNA cleavage protectors Cell Biol. Toxicol. 16 2000 91 98
19. P.L. Olive, and J.P. Banáth The comet assay: a method to measure DNA damage in individual cells Nat. Protoc. 1 2006 23 29
20. A.R. Collins Comet assay for DNA damage and repair: principles, applications and limitations Mol. Biotechnol. 26 2004 249 261
21. I. Orhan, M. Abu-Asaker, F.S. Senol, G. Yilmaz, and B. Senser Free redical scavenging properties and phenolic charecterization of some edible plants Food Chem. 114 2009 276 281
22. M.B. Arnao, A. Cano, and M. Acosta The hydrophilic and lipophilic contribution to total antioxidant activity Food Chem. 73 2001 239 244
23. P. Griess Bemerkungen zu der abhandlung der H.H. Weselsky und Benedikt "Ueber einige azoverbindungen" Chem. Ber. 12 1879 426 428
24. D.K. Jangir, G. Tyagi, R. Mehrotra, and S. Kundu Carboplatin interaction with calf thymus DNA: a FTIR spectroscopic approach J. Mol. Struct. 969 2010 126 129
25. I. Parejo, C. Codina, C. Petrakis, and P. Kefalas Evaluation of scavenging activity assessed by Co(II)/EDTA-induced luminol chemiluminescence and DDPH (2,2-diphenyl-1-picrylhydrazyl) free radical assay J. Pharmacol. Toxicol. Meth. 44 2007 507 512
26. X. Nianzeng, Y. Chen, S.H. Mitchell, and C. Young Quercetin inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells Carcinogenesis 3 2001 409 414
27. J. Nordberg, and E.S. Arner Reactive oxygen species, antioxidants, and the mammalian thioredoxin system Free Radic. Biol. Med. 31 2001 1287 1312
28. M. Valko, D. Leibfritz, J. Moncol, M.T.D. Cronin, M. Mazur, and J. Telser Free radicals and antioxidants in normal physiological functions and human disease Int. J. Biochem. Cell Biol. 39 2007 44 84
29. S. Bjelland, and E. Seeberg Mutagenicity, toxicity and repair of DNA base damage induced by oxidation Mutat. Res. 531 2003 37 80
30. G. Rusak, H.O. Gutzeit, and J. Ludwig-Muller Structurally related flavonoids with antioxidative properties differentially affect cell cycle progression and apoptosis of human acute leukemia cells Nutr. Res. 25 2005 141 153
31. A. Kootstra Protection from UV-B-induced DNA damage by flavonoids Plant Mol. Biol. 26 1994 771 774
32. S.J. Duthie, A.R. Collins, G.G. Duthie, and V.L. Dobson Quercetin and myricetin protect against hydrogen peroxide-induced DNA damage (strand breaks and oxidised pyrimidines) in human lymphocyte Mutat. Res. 393 1997 223 231
33. A. Robaszkiewicz, A. Balcerczyk, and G. Bartosz Antioxidative and prooxidative effects of quercetin on A549 cells Cell Biol. Int. 31 2007 1245 1250
34. M. Kessler, G. Ubeaud, and L. Jung Anti- and pro-oxidant activity of rutin and quercetin derivatives J. Pharm. Pharmacol. 55 2003 131 142
35. V.S. Rogovskii, A.I. Matiushin, N.L. Shimanovskii, A.V. Semeikin, T.S. Kukhareva, A.M. Koroteev, M.P. Koroteev, and E.E. Nifantev Antiproliferative and antioxidant activity of new dihydroquercetin derivatives Eksp Klin Farmakol. 73 2010 39 42
36. S. Pfuhler, and W. Uwe Detection of DNA-crosslinking agents with the alkaline comet assay Environ. Mol. Mutagen. 27 1996 196 201
37. F. Kassie, W. Parzefall, and S. Knasmuller Single cell gel electrophoresis assay: a new technique for human biomonitoring studies Mutat. Res. 463 2000 13 31
38. S.J. Duthie, and V.L. Dobson Dietry flavonoids protect human colonocyte DNA from oxidative attack in vitro Eur. J. Nutr. 38 1999 28 34
39. L.C. Wilms, P.C.H. Hollman, A.W. Boots, and J.C.S. Kleinjans Protection by quercetin and quercetin-rich fruit juice against induction of oxidative DNA damage and formation of BPDE-DNA adducts in human lymphocytes Mutat. Res. 582 2005 155 162
40. B.L. Pool-Zobel, A. Bub, N. Schröder, and G. Rechkemmer Anthocyanins are potent antioxidants in model systems but do not reduce endogenous oxidative DNA damage in human colon cells Eur. J. Nutr. 38 1999 227 234
41. S.C. Forester, and J.D. Lambert The role of antioxidant versus pro-oxidant effects of green tea polyphenols in cancer prevention Mol. Nutr. Food Res. 55 2011 844 854
42. K.D. Croft The chemistry and biological effects of flavonoids and phenolic acids Ann. NY Acad. Sci. 854 1998 435 442
43. D. Amic, D. Davidovic Amic, D. Beslo, and N. Trinajstic Structure-radical scavenging activity relationship of flavonoids Croatia Chem. Acta. 76 2003 55 61
44. H. Zhang Strucure- activity relatioships and rational design strategies for radical scavenging antioxidants Curr. Comput. Aided Drug Des. 1 2005 257 273
45. N. Yamamoto, J.H. Moon, T. Tsushida, A. Nagao, and J. Terao Inhibitory effect of quercetin metabolites and their related derivatives on copper ion-induced lipid per oxidation in human low-density lipoprotein Arch. Biochem. Biophys. 372 1999 347 354
46. A. Latan The relation of structure to antioxidant activity of quercetin and some of its derivatives I. Primary activity J. Food Sci. 31 2006 518 523
47. M.S. Ahmed, V. Ramesh, V. Nagaraja, J.H. Parish, and S.M. Hadi Mode of binding of quercetin to DNA Mutagenesis 1 1994 193 197
48. J. Tan, L. Zhu, and B. Wang DNA binding and cleavage activity of quercetin nickel (II) complex Dalton Trans. 2009 4722 4728
49. S.M. Ahmadi, M.A.H. Feizi, G. Dehgan, and J.E.N. Dolatabadi In vitro studies on calf thymus DNA interaction with quercetin-palladium (II) complex IPCBEE 5 2011 110 113
50. C.D. Kanakisa, P.A. Tarantilisa, M.G. Polissioua, S. Diamantogloub, and H.A. Tajmir-Riahib DNA interaction with naturally occurring antioxidant flavonoids quercetin, kaempferol, and delphinidin J. Biomol. Struct. Dyn. 22 2005 719 724
51. A.H. Hegde, S.N. Prashanth, and J. Seetharamappa Interaction of antioxidant flavonoids with calf thymus DNA analyzed by spectroscopic and electrochemical methods J. Pharmaceut. Biomed. 63 2012 40 46
52. J. Cadet, B. Kalyanaraman, M. Fontecave, J.L. Pierre, Analysis of free radicals in biological system, Boston, 1995.
53. R. Palchaudhuri, and P.J. Hergenrother DNA as a target for anticancer compound: methods to determine the mode of binding and the mechanism of action Curr. Opin. Biotechnol. 18 2007 497 503