Inhibition of radical-induced DNA strand breaks by water-soluble constituents of coffee: Phenolics and caffeine metabolites

Free Radical Research

Volumn 47, Issue 6-7, 2013, Pages 480-487

  Rathod, M A ^a   Patel, D ^a   Das, A ^a   Tipparaju, S R ^b   Shinde, S S ^b   Anderson, Robert F ^a,b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Antioxidants; Coffee; DNA strand breaks; Fast chemical repair; Reduction potentials

Indexed keywords

1 METHYLURIC ACID; 1 METHYLXANTHINE; 1,3 DIMETHYLURIC ACID; 1,7 DIMETHYLURIC ACID; 3 METHYLXANTHINE; 7 METHYLURIC ACID; 7 METHYLXANTHINE; CAFFEIC ACID; CAFFEINE; CAFFEINE DERIVATIVE; CHLOROGENIC ACID; COUMARIC ACID; DNA BASE; FERULIC ACID; FREE RADICAL; PARAXANTHINE; PHENOL DERIVATIVE; PLASMID DNA; REACTIVE OXYGEN METABOLITE; THEOBROMINE; THEOPHYLLINE; UNCLASSIFIED DRUG;

ARTICLE; COFFEE; CONTROLLED STUDY; DNA DAMAGE; DRUG DNA INTERACTION; GAMMA IRRADIATION; IN VITRO STUDY; REDUCTION; SINGLE STRANDED DNA BREAK;

CAFFEINE; CHLOROGENIC ACID; COFFEE; DNA BREAKS, SINGLE-STRANDED; FREE RADICALS; GAMMA RAYS; HUMANS; MOLECULAR STRUCTURE; PHENOLS; SOLUBILITY; WATER;

EID: 84878845966     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715762.2013.788167     Document Type: Article

References (50)

1. Bravi F, Bosetti C, Tavani A, Bagnardi V, Gallus S, Negri E, et al. Coff ee drinking and hepatocellular carcinoma risk: a meta-analysis. Hepatol 2007; 46 : 430-435.
2. Corrao G, Zambon A, Bagnardi V, D'Aicis A, Klatsky A; Collaborative SIDECIR Group. Coff ee, caff eine, and the risk of liver cirrhosis. Ann Epidemiol 2001; 11 : 458-465.
3. Tverdal A, Skurtveit S. Coff ee intake and mortality from liver cirrhosis. Ann Epidemiol 2003; 12 : 419-423.
4. Hern á n MA, Takkouche B, Caama ñ o-Isorna F, Gestal-Otero JJ. A meta-analysis of coff ee drinking, cigarette smoking, and the risk of Parkinson's disease. Ann Neurol 2002; 52: 276- 284.
5. Costa J, Lunet N, Santos C, Santos J, Vaz-Carneiro A. Caff eine exposure and the risk of Parkinson's disease: a systematic review and meta-analysis of observational studies. J Alzheimer's Disease 2010; 20 : S221 - S238.
6. Michels KB, Willett WC, Fuchs CS, Giovannucci E. Coff ee, tea, and caff eine consumption and incidence of colon and rectal cancer. J Natl Cancer Inst 2005; 97 : 282-292.
7. JoséS, Vicente V, Ishimoto EY, Cruz RJ, Dias C, Pereira S, Da Silva Torres EAF. Increase of the activity of phase II antioxidant enzymes in rats after a single dose of coff ee. J Agric Food Chem 2011; 59: 10887- 10892.
8. Grubben MJAL, van den Braak CCM, Broekhuizen R, de Jong R, Van Rijt L, de Ruijter E, et al. The eff ect of unfi ltered coffee on potential biomarkers for colonic cancer risk in healthy volunteers: a randomised trial. Aliment Pharmacol Ther 2000; 14 : 1181-1190.
9. TPA, Kamat JP, Mohan H, Kesavan PC. Caffeine as an antioxidant: inhibition of lipid peroxidation induced by reactive oxygen species. Biochimica et Biophysica Acta 1996; 1282 : 63-70.
10. Lee C. Antioxidant ability of caff eine and its metabolites based on the study of oxygen radical absorbing capacity and inhibition of LDL peroxidation. Clin Chem Acta 2000; 295 : 141-154.
11. Ames BN, Shigenaga MK, Hagen TM : Oxidants, antioxidants, and the degenerative diseases of aging. Proc Natl Acad Sci USA 1993; 90 : 7915-7922.
12. Zhang J, Perry G, Smith MA, Robertson D, Olson SJ, Graham DG, Montine TJ. Parkinson's disease is associated with oxidative damage to cytoplasmic DNA and RNA in substantia nigra neurons. Am J Pathology 1999; 154 : 1423-1429.
13. Ozawa T, Hayakawa M, Katsumata K, Yoneda M, Ikebe S, Mizuno Y. Fragile mitochondrial DNA: The missing link in the apoptotic neuronal cell death in parkinson's disease. Biochem Biophys Res Commun 1997; 235 : 158-161.
14. Iwai K, Kishimoto N, Kaakino Y, Mochida K, Fujita T. In vitro antioxidative eff ects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coff ee beans. J Agric Food Chem 2004; 52: 4893- 4898.
15. Cavin C, Mace K, Off ord EA, Schilter B. Protective eff ects of coff ee diterpenes against afl atoxin B1-induced genotoxicity: mechanisms in rat and human cells. Food Chem Toxicol 2001; 39 : 549-556.
16. Huber WW, Scharf G, Rossmanith W, Prustomersky S, GraslKraupp B, Peter B, et al. The coff ee components, kahweol and cafestol induce γ -gluamylcysteine synthetase, the rate limiting enzyme of chemoprotective glutathione synthetase, in several organs of the rat. Arch Toxicol 2002; 75: 685- 694.
17. Lee KJ, Jeong HG. Protective eff ects of kahweol and cafestol against hydrogen peroxide-induced oxidative stress and DNA damage. Toxicol Lett 2007; 173 : 80-87.
18. Anderson RF, Amarasinghe C, Fisher LJ, Mak WB, Packer JE. Reduction in free-radical-induced DNA strand breaks and base damage through fast chemical repair by fl avonoids. Free Radic Res 2000; 33: 91- 103.
19. Anderson RF, Fisher LJ, Harris T. The pivotal antioxidant hypothesis for the role of fl avonoids in their reduction of HO. radical-induced damage on DNA. Redox Rep 2001; 6: 197-199.
20. Anderson RF, Fisher LJ, Hara Y, Harris T, Mak WB, Melton LD, Packer JE. Green tea catechins partially protect DNA from. OH radical-induced strand breaks and base damage through fast chemical repair of DNA radicals. Carcinogenesis 2001; 22 : 1189-1193.
21. Zheng R, Shi Y, Jia Z, Zhao C, Zhang Q, Tan X. Fast repair of DNA radicals. Chem Soc Rev 2010; 39 : 2827-2834.
22. Schulte-Frohlinde D, Behrens G, Onal A. Lifetime of peroxyl radicals of poly(U), poly(A) and single-and double-stranded DNA and the rate of their reaction with thiols. Int J Radiat Biol 1986; 50 : 103-110.
23. Jovanovic SV, Steenken S, Tosic M, Marjanovic B, Simic MG. Flavonoids as antioxidants. J Am Chem Soc 1994; 116 : 4846-4851.
24. Steenken S, Jovanovic SV. How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J Am Chem Soc 1997; 119 : 617-618.
25. Shinde SS, Maroz A, Hay MP, Anderson RF. One-electron reduction potential of the neutral guanyl radical in the GC base pair of duplex DNA. J Am Chem Soc 2009; 131 : 5203-5207.
26. Epe B, Pfl aum M, Haring M, Hegler J, Rudiger H. Use of repair endonucleases to characterize DNA damage induced by reactive oxygen species in cellular and cell-free systems. Toxicology Lett 1993; 67 : 57-72.
27. Krisch RE, Tan PM, Flick MB. A sensitive SV40 viral probe assay for DNA strand breaks and their biological repair in higher cells: techniques and preliminary results. Radiat Res 1985; 101 : 356-372.
28. Anderson RF, Denny WA, Li W, Packer JE, Tercel M, Wilson WR. Pulse radiolysis studies on the fragmentation of arylmethyl quaternary nitrogen mustards by one-electron reduction in aqueous solution. J Phys Chem A 1997; 101: 9704- 9709.
29. Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J Phys Chem Ref Data 1989; 18 : 1637-1755.
30. Anderson RF, Shinde SS, Hay MP, Gamage SA, Denny WA. Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4- benzotriazine 1,4-dioxides. Org Biomol Chem 2005; 3 : 2167-2174.
31. Buxton GV, Greenstock CL, Helman WP, Ross AB. Critical review of rate constants of hydrated electrons, hydrogen atoms and hydroxyl radicals (.OH/.O-) in aqueous solution. J Phys Chem Ref Data 1988; 17 : 513-886.
32. van Hemmen JJ, Meuling WJA. Inactivation of biologically active DNA by γ -ray-induced superoxide radicals and their dismutation products singlet oxygen and hydrogen peroxide. Biochim Biophys Acta 1975; 402 : 133-141.
33. Hodgkins PS, Fairman MP, O'Neill P. Rejoining of gammaradiation- induced single-strand breaks in plasmid DNA by human cell extracts: dependence on the concentration of the hydroxyl radical scavenger, tris. Radiat Res 1996; 145: 24- 30.
34. Wallace SS. Enzymatic processing of radiation-induced free radical damage in DNA. Radiat Res 1998; 150: S60- S69.
35. Lelo A, Miners JO, Roson R, Birkett DJ. Assessment of caffeine exposure: Caff eine content of beverages, caff eine intake, and plasma concentrations of methylxanthines. Clin Pharmacol Ther 1986; 39 : 54-59.
36. von Sonntag C. Free-Radical-Induced DNA Damage and Its Repair. Berlin Heidelberg: Springer-Verlag; 2006.
37. Buettner GR. The pecking order of free radicals and antioxidants: lipid peroxidation, γ -tocopherol, and ascorbate. Arch Biochem Biophys 1993; 300 : 535-543.
38. Stockert AL, Shinde SS, Anderson RF, Hille R. The reaction mechanism of xanthine oxidase: Evidence for two-electron chemistry rather than sequential one-electron steps. J Am Chem Soc 2002; 124 : 14554-14555.
39. Foley S, Navaratnam S, McGarvey DJ, Land EJ, Truscott TG, Rice-Evans CA. Singlet oxygen quenching and the redox properties of hydroxycinnamic acids. Free Radic Biol Med 1999; 26 : 1202-1208.
40. Mahal HS, Mukherjee T. Radical scavenging reactions of chlorogenic acid: a pulse radiolysis study. Res Chem Intermed 2006; 32 : 671-682.
41. Jiang Y, Lin WZ, Yao SD, Lin NY, Zhu DY. Fast repair of oxidizing OH adducts of DNA by hydroxycinnamic acid derivatives. A pulse radiolytic study. Radiat Phys Chem 1999; 54 : 355-359.
42. Leakey TE. Simultaneous analysis of theophylline, caff eine and eight of their metabolic products in human plasma by gradient high-performance liquid chromatography. J Chromatog 1990; 507: 199- 220.
43. Soto J, Sacristan JA, Alsar MJ. Cerebrospinal fl uid concentrations of caff eine following oral drug administration: correlation with salivary and plasma concentrations. Ther Drug Monit 1994; 16 : 108-110.
44. Muir KT, Kunitani M, Riegelman S. Improved high-performance liquid chromatography assay for theophylline in plasma and saliva in the presence of caff eine and its metabolites and comparisons with three other assays. J Chromatog 1982; 231: 73- 82.
45. Graham TE, Spriet LL. Metabolic, catecholamine, and exercise performance responses to various doses of caff eine. J Appl Physiol 1995; 78 : 867-874.
46. Renouf M, Guy PA, Marmet C, Fraering A-L, Longet K, Moulin J, et al. Measurement of caff eic and ferulic acid equivalents in plasma after coff ee consumption: small intestine and colon are key sites for coff ee metabolism. Mol Nutr Food Res 2010; 54: 760- 766.
47. Farah A, Monteiro M, Donangelo CM, Lafay S. Chlorogenic acids from green coff ee extract are highly bioavailable in humans. J Nutr 2008, 138 : 2309-2315.
48. Monteiro M, Farah A, Perrone D, Trugo LC, Donangelo C. Chlorogenic acid compounds from coff ee are diff erentially absorbed and metabolized in humans. J Nutr 2007; 137 : 2196-2201.
49. Powers EL. Purine and its analogues and radiation damage in Bacillus megaterum spores. Int J Radiat Biol 1986; 50: 983-993.
50. Vinchurkar MS, Rao BSM, Mohan H, Mittal JP. Kinetics, spectral and redox behaviour of OH adducts of methylxanthines: a radiation chemical study. J Chem Soc, Perkin Trans 1999; 609-617.