Evaluation of multiple oxidation products for monitoring effects of antioxidants in fenton oxidation of 2′-deoxyguanosine

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 6, 2006, Pages 2350-2358

  Grey, Carl Elovson ^a   Adlercreutz, Patrick ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

2 deoxyguanosine; Ascorbic acid; Catechin; Fenton reaction; Oxidation

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; CATECHIN; DEOXYGUANOSINE; FENTON'S REAGENT; HYDROGEN PEROXIDE; IRON;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION REDUCTION REACTION;

ANTIOXIDANTS; ASCORBIC ACID; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; HYDROGEN PEROXIDE; IRON; MASS SPECTROMETRY; OXIDATION-REDUCTION;

EID: 33645792170     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf052202q     Document Type: Article

References (38)

1. Cooke, M. S.; Evans, M. D.; Dizdaroglu, M.; Lunec, J. Oxidative DNA damage: mechanisms, mutation, and disease. FASEB J. 2003, 17, 1195-1214.
2. Breen, A. P.; Murphy, J. A. Reactions of oxyl radicals with DNA. Free Radical Biol. Med. 1995, 18, 1033-1077.
3. Henle, E. S.; Luo, Y.; Gassmann, W.; Linn, S. Oxidative damage to DNA constituents by iron-mediated Fenton reactions. The deoxyguanosine family. J. Biol. Chem. 1996, 271, 21177-21186.
4. Frelon, S.; Douki, T.; Favier, A.; Cadet, J. Comparative study of base damage induced by gamma radiation and Fenton reaction in isolated DNA. J. Chem. Soc., Perkin Trans. 1 2002, 2866-2870.
5. Luo, W.; Muller, J. G.; Rachlin, E. M.; Burrows, C. J. Characterization of Hydantoin Products from One-Electron Oxidation of 8-Oxo-7,8-dihydroguanosine in a Nucleoside Model. Chem. Res. Toxicol. 2001, 14, 927-938.
6. Cadet, J.; Douki, T.; Gasparutto, D.; Ravanat, J.-L. Oxidative damage to DNA: formation, measurement, and biochemical features. Mutat. Res. 2003, 531, 5-23.
7. Grey, C. E.; Adlercreutz, P. Time and Concentration Dependence of Fenton Induced Oxidation of dG. Nucleosides Nucleotides 2006, 25, in press.
8. Jaruga, P.; Birincioglu, M.; Rodriguez, H.; Dizdaroglu, M. Mass spectrometric assays for the tandem lesion 8,5′-cyclo-2′- deoxyguanosine in mammalian DNA. Biochemistry 2002, 41, 3703-3711.
9. Kuraoka, I.; Bender, C.; Romieu, A.; Cadet, J.; Wood, R. D.; Lindahl, T. Removal of oxygen free-radical-induced 5′,8-purine cyclodeoxynucleosides from DNA by the nucleotide excision-repair pathway in human cells. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 3832-3837.
10. Qi, W.; Reiter, R. J.; Tan, D.-X.; Garcia, J. J.; Manchester, L. C.; Karbownik, M.; Calvo, J. R. Chromium(III)-induced 8-hydroxydeoxyguanosine in DNA and its reduction by antioxidants: comparative effects of melatonin, ascorbate, and vitamin E. Environ. Health Perspect. 2000, 108, 399-402.
11. Cai, Q.; Rahn, R. O.; Zhang, R. Dietary flavonoids, quercetin, luteolin, and genistein, reduce oxidative DNA damage and lipid peroxidation and quench free radicals. Cancer Lett. 1997, 119, 99-107.
12. Spear, N.; Aust, S. D. Effects of glutathione on Fenton reagent-dependent radical production and DNA oxidation. Arch. Biochem. Biophys. 1995, 324, 111-116.
13. Halliwell, B. Vitamin C and genomic stability. Mutat. Res. 2001, 475, 29-35.
14. Carr, A.; Frei, B. Does vitamin C act as a pro-oxidant under physiological conditions? FASEB J. 1999, 13, 1007-1024.
15. Kondo, K.; Kurihara, M.; Miyata, N.; Suzuki, T.; Toyoda, M. Mechanistic studies of catechins as antioxidants against radical oxidation. Arch. Biochem. Biophys. 1999, 562, 79-86.
16. Mira, L.; Fernandez, M. T.; Santos, M.; Rocha, R.; Florencio, M. H.; Jennings, K. R. Interactions of flavonoids with iron and copper ions: A Mechanism for their antioxidant activity. Free Radical Res. 2002, 36, 1199-1208.
17. van Acker, S. A. B. E.; van den Berg, D.-J.; Tromp, M. N. J. L.; Griffioen, D. H.; van Bennekom, W. P.; van der Vijgh, W. J. F.; Bast, A. Structural aspects of antioxidant activity of flavonoids. Free Radical Biol Med. 1996, 20, 331-342.
18. Manach, C.; Texier, O.; Morand, C.; Crespy, V.; Regerat, F.; Demigne, C.; Remesy, C. Comparison of the bioavailability of quercetin and catechin in rats. Free Radical Biol. Med. 1999, 27, 1259-1266.
19. Reddy, D.; Iden, C. R. Analysis of modified deoxynucleosides by electrospray ionization mass spectrometry. Nucleosides Nucleotides 1993, 12, 815-826.
20. 18O]-labeled singlet oxygen as a tool for mechanistic studies of 8-oxo-7,8-dihydroguanine oxidative damage: detection of spiroiminodihydantoin, imidazolone, and oxazolone derivatives. Biol. Chem. 2002, 383, 607-617.
21. Duarte, V.; Gasparutto, D.; Yamaguchi, L. P.; Ravanat, J.-L.; Martinez, G. R.; Medeiros, M. H. G.; Di Mascio, P.; Cadet, J. Oxaluric acid as the major product of singlet oxygen-mediated oxidation of 8-oxo-7,8-dihydroguanine in DNA. J. Am. Chem. Soc. 2000, 122, 12622-12628.
22. Traut, T. W. Physiological concentrations of purines and pyrimidines. Mol. Cell. Biochem. 1994, 140, 1-22.
23. Suzuki, T.; Nakano, T.; Masuda, M.; Ohshima, H. Epigallocatechin Gallate Markedly Enhances Formation of 8-Oxo-7,8-Dihydro-2′-Deoxyguanosine in the Reaction of 2′-Deoxyguanosine with Hypochlorous Acid. Free Radical Biol. Med. 2004, 36, 1087-1093.
24. Dizdaroglu, M.; Jaruga, P.; Birincioglu, M.; Rodriguez, H. Free radical-induced damage to DNA: mechanisms and measurement. Free Radical Biol. Med. 2002, 32, 1102-1115.
25. Whiteman, M.; Hong, H. S.; Jenner, A.; Halliwell, B. Loss of oxidized and chlorinated bases in DNA treated with reactive oxygen species: implications for assessment of oxidative damage in vivo. Biochem. Biophys. Res. Commun. 2002, 296, 883-889.
26. Halliwell, B.; Clement, M. V.; Long, L. H. Hydrogen peroxide in the human body. FEBS Lett. 2000, 486, 10-13.
27. Colwell, B. A.; Morris, D. L. Formation of the oxidative damage marker 8-hydroxy-2′-deoxyguanosine from the nucleoside 2′-deoxyguanosine: parameter studies and evidence of Fe(II) binding. J. Inorg. Biochem. 2003, 94, 100-105.
28. Frei, B.; Higdon, J. V. Antioxidant activity of tea polyphenols in vivo: Evidence from animal studies. J. Nutr. 2003, 133, 3275S-3284S.
29. Duarte, T. L.; Lunec, J. Review: When is an antioxidant not an antioxidant? A review of novel actions and reactions of vitamin C. Free Radical Res. 2005, 39, 671-686.
30. Sawai, Y.; Moon, J.-H. NMR Analytical Approach to Clarify the Molecular Mechanisms of the Antioxidative and Radical-Scavenging Activities of Antioxidants in Tea Using 1,1-Diphenyl-2-picrylhydrazyl. J. Agric. Food Chem. 2000, 48, 6247-6253.
31. Donovan, J. L.; Bell, J. R.; Kasim-Karakas, S.; German, J. B.; Walzem, R. L.; Hansen, R. J.; Waterhouse, A. L. Catechin is present as metabolites in human plasma after consumption of red wine. J. Nutr. 1999, 129, 1662-1668.
32. Rios, L. Y.; Gonthier, M.-P.; Remesy, C.; Mila, I.; Lapierre, C.; Lazarus, S. A.; Williamson, G.; Scalbert, A. Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects. Am. J. Clin. Nutr. 2003, 77, 912-918.
33. Halliwell, B. The antioxidant paradox. Lancet 2000, 355, 1179-1180.
34. Niki, E.; Noguchi, N. Evaluation of antioxidant capacity. What capacity is being measured by which method? IUBMB Life 2000, 50, 323-329.
35. Berger, T. M.; Polidori, M. C.; Dabbagh, A.; Evans, P. J.; Halliwell, B.; Morrow, J. D.; Roberts, L. J., II.; Frei, B. Antioxidant activity of vitamin C in iron-overloaded human plasma. J. Biol. Chem. 1997, 272, 15656-15660.
36. Proteggente, A. R.; England, T. G.; Rice-Evans, C. A.; Halliwell, B. Iron Supplementation and Oxidative Damage to DNA in Healthy Individuals with High Plasma Ascorbate. Biochem. Biophys. Res. Commun. 2001, 288, 245-251.
37. Oikawa, S.; Furukawa, A.; Asada, H.; Hirakawa, K.; Kawanishi, S. Catechins induce oxidative damage to cellular and isolated DNA through the generation of reactive oxygen species. Free Radical Res. 2003, 37, 881-890.
38. Furukawa, A.; Oikawa, S.; Murata, M.; Hiraku, Y.; Kawanishi, S. (-)-Epigallocatechin gallate causes oxidative damage to isolated and cellular DNA. Biochem. Pharmacol. 2003, 66, 1769-1778.