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Original Article

Oxidation of Caffeine and Related Methylxanthines in Ascorbate and Polyphenol-Driven Fenton-Type Oxidations

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Pages 225-240 | Received 17 Aug 1995, Published online: 07 Jul 2009

References

  • Dews P. B. Caffeine. Perspectives from Recent Research. Springer Verlag, Berlin, Heidelberg, New York, Tokyo 1984
  • Barone JJ., Grice H. C. Seventh International caffeine workshop, Santorini, Greece 13–17 June 1993. Food and Chemical Toxicology 1994; 32: 65–77
  • D'Ambrosio S.M. Evaluation of the genotoxicity data on caffeine. Regulatory Toxicology and Pharmacology 1994; 19: 243–281
  • Shi X., Dalal N. S., Jain A. C. Antioxidant behaviour of caffeine: efficient scavenging of hydroxyl radicals. Food and Chemical Toxicology 1991; 29: 1–6
  • Stadler R. H., Fay L. B. Antioxidative reactions of caffeine: Formation of 8-oxocaffeine (1,3,7–trimethyluric acid) in coffee subjected to oxidative stress. Journal of Agricultural and Food Chemistry 1995; 43: 1332–1338
  • Zbaida S., Kariv R., Fischer P., Gilhar D. Reactions of theophylline, theobromine and caffeine with Fenton's reagent - simulation of hepatic metabolism. Xenobiotica 1987; 17: 617–621
  • Floyd R. A., Watson J. J., Wong P. K., Altmiller D. H., Rickard R. C. Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanism of formation. Free Radical Research Communications 1986; 1: 163–172
  • Kasai H., Nishimura S. Hydroxylation of guanine in nucleosides and DNA at the C-8 position by heated glucose and oxygen radical forming agents. Environmental Health Perspectives 1986; 67: 111–116
  • Kasai H., Crain P. F., Kuchino Y., Nishimura S., Ootsuyama A., Tanooka H. Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Cnrcinogenesis 1986; 7: 1849–1851
  • Halliwell B., Aruoma O. I. DNA damage by oxygen-derived species. Its mechanism and measurement in mammalian systems. FEES Letters 1991; 281: 9–19
  • Harman D. The aging process. Proceedings of the National Academy of Sciences of U.S.A 1981; 78: 7124–7128
  • Am- B. N., Shigenaga M. K., Hagen T. M. Oxidants, antioxidants, and the degenerative diseases of aging. Proceedings of the Nationar Academy of Sciences of U.S.A 1993; 90: 7915–7922
  • Kasai H., Nishimura S. Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Research 1984; 12: 2137–2145
  • Aruoma O. I., Halliwell B., Gajewski E., Dizdaroglu M. Copper ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochemical Journal 1991; 273: 601–604
  • Fischer-Nielsen A. F., Poulsen H. E., Loft S. 8-Hydroxydeoxyguanosine in vitro: effects of glutathione, ascorbate, and 5-aminosalicylic acid. Free Radical Biology and Medicine 1992; 13: 121–126
  • Inoue S., Ito K., Yamamoto K., Kawanishi S. Caffeic acid causes metal-dependent damage to cellular and isolated DNA through H2O2 formation. Carcinogenesis 1992; 13: 1497–1502
  • Stadler R. H., Turesky R. J., Müller O., Markovic J., Leong-Morgenthaler P.-M. The inhibitory effects of coffee on radical-mediated oxidation and mutagenicity. Mutation Research 1994; 308: 177–190
  • Stadler R. H., Marcovic J., Turesky R. J. In vitro anti- and pro-oxidative effects of natural polyphenols. Biological and Trace Element Research 1995; 47: 299–305
  • Lin T. S., Cheng J.-C., Ishiguro K., Sartorelli A. C. 8-Substituted guanosine and 2′-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells. Journal of Medicinal Chemistty 1985; 28: 1194–1198
  • Buettner G. R. In the absence of catalytic metals ascorbate does not autoxidize at pH 7 ascorbate as a test for catalytic metals. Journal of Biochemical and Biophysical Methods 1988; 16: 27–40
  • Philippossian G., Fumeaux R. Nestlé Research Centre, unpublished data
  • Joint assessment of commodity chemicals report No. 22. Hydrogen peroxide. Brussels, Belgium 1993, ECETOC (CAS No. 7722–84–1)
  • Muhammad S. S., Navaneeth Rao T. Spectro-photometric determination of the dissociation constant of hydrogen peroxide. Journal of the Chemical Society 1957; 1077–1078
  • Buettner G. R., Doherty T. P., Patterson L. K. The kinetics of the reaction of superoxide radical with Fe(III) complexes of EDTA, DETAPAC and HEDTA. FEBS Letters 1983; 158: 143–146
  • Bergmann F., Dikstein S. Studies on uric acid and related compounds. III Observations on the specificity of mammalian xanthine oxidases. Journal of Biological Chemistry 1957; 223: 765–780
  • Pogozelski W. K., McNeese T. J., Tullius T. D. What species is responsible for strand scission in the reaction of [FeIIEDTA]2– and H2O2 with DNA?. Journal of the American Ckemical Society 1995; 117: 6428–6433
  • Wink D. A., Nims R. W., Saavedra J. E., Utermahlen W. E., Ford P. C. The Fenton oxidation mechanism: reactivities of biological relevant substrates with two oxidising intermediates differ from those predicted for the hydroxyl radical. Proceedings of the National Academy of Sciences of U.S.A 1994; 91: 6604–6608
  • Luo Y., Han Z., Chin S. M., Linn S. Three chemically distinct types of oxidants formed by ironmediated Fenton reactions in the presence of DNA. Proceedings of the National Academy of Sciences of U.S.A 1994; 91: 12438–12442
  • Brodie B. B., Axelrod J., Shore P. A., Udenfriend S. Ascorbic acid in aromatic hydroxylation. II. Products formed by reaction of substrates with ascorbic acid, ferrous iron, and oxygen. Journal of Biological Chemisty 1954; 208: 741–750
  • Udenfriend S., Clark C. T., Axelrod J., Brodie B. B. Ascorbic acid in aromatic hydroxylation. I. A model system for aromatic hydroxylation. Journal of Biological Chemistry 1954; 208: 731–739
  • Cohen G. CRC Handbook of Methods for Oxygen Radical Research, R. A. Greenwald. CRC, Boca Raton, Fl 1986; 55–64
  • Graf E., Mahoney J. R., Bryant R. G., Eaton J. W. Iron-catalyzed hydroxyl radical formation. Stringent requirement for free iron coordination site. Journal of Biological Chemistry 1984; 259: 3620–3624
  • Aruoma O. I., Halliwell B., Gajewski E., Dizdaroglu M. Damage to the bases in DNA induced by hydrogen peroxide and ferric ion chelates. Journal of Biological Chemistry 1989; 264: 20509–20512
  • Hicks M., Gebicki J. M. Rate constants for reaction of hydroxyl radicals with Tris, Tricine and Hepes buffers. FEBS Letters 1986; 199: 92–94
  • Ravanat J.-L., Turesky R. J., Gremaud E., Trudel L. J., Stadler R. H. Determination of 8-oxoguanine in DNA by gas chromatography-mass spectrometry and HPLC-electrochemical detection: Overestimation of the background level of the oxidized base by the gas chromatography-mass spectrometry assay. Chemical Research in Toxicology 1995; 8: 1039–1045
  • Fraga C. G., Shigenaga M. K., Park J.-W., Degan P., Ames B. N. Oxidative damage to DNA during aging: 8-hydroxy-2′-deoxyguanosine in rat organ DNA and urine. Proceedings of the National Academy of Sciences of U.S.A 1990; 87: 4533–4537
  • Dizdaroglu M., Bergtold D. S. Characterization of free radical-induced base damage in DNA at biologically relevant levels. Analytical Chemistry 1986; 156: 182–188
  • Steenken S. Purine bases, nucleosides, and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e- and OH adducts. Chemical Reviews 1989; 89: 503–520
  • Kesavan P. C., Powers E. L. Differential modification of oxic and anoxic components of radiation damage in Bacillus megaterium spores by caffeine. International Journal of Radiation Biology 1985; 48: 223–233
  • Breen A. P., Murphy J. A. Reactions of oxyl radicals with DNA. Free Radical Biology and Medicine 1995; 18: 1033–1077
  • Inoue S., Kawanishi S. Hydroxyl radical production and human DNA damage induced by ferric nitrilotriacetate and hydrogen peroxide. Cancer Research 1987; 47: 6522–6527
  • Gutteridge J. M.C. Reactivity of hydroxyl and hydroxyl-like radicals discriminated by release of thiobarbituric acid-reactive material from deoxy sugars, nucleosides and benzoate. Biochemical Journal 1984; 224: 761–767
  • Laughton M. J., Halliwell B., Evans P. J., Hoult J. B.S. Antioxidant and pro-oxidant actions of the plant phenolics Quercetin, Gossypol and Myricetin. Biochemical Pharmacology 1989; 38: 2859–2865
  • Rowley D. A., Halliwell B. Formation of hydroxyl radicals from hydrogen peroxide and iron salts by superoxide- and ascorbate-dependent mechanisms: relevance to the pathology of rheumatoid disease. Clinical Science 1983; 64: 649–653
  • Ames B. N. Dietary carcinogens and anticarcinogens: oxygen radicals and degenerative diseases. Science 1983; 221: 1256–1264
  • Aruoma O. I. Free radicals and food. Chemistry in Britain 1993; 29: 210–214
  • Aruoma O. I. Nutrition and health aspects of free radicals and antioxidants. Food and Chemical Toxicology 1994; 32: 671–683
  • Marklund S., Marklund G. Involvement of the superoxideanion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. European Journal of Biochemistry 1974; 86: 469–474
  • Ochiai M., Nagao M., Wakabayashi K., Sugimura T. Superoxide dismutase acts as an enhancing factor for quercitin mutagenesis in rat liver cytosol by preventing its decomposition. Mutation Research 1984; 129: 19–24
  • Hanham A. F., Dunn B. P., Stich H. F. Clastogenic activity of caffeic acid and its relationship to hydrogen peroxide generated during autoxidation. Mutation Research 1983; 116: 333–339
  • Iwahashi H., Morishita H., Ishii T., Sugata R., Kido R. Enhancement by catechols of hydroxyl-radical formation in the presence of ferric ions and hydrogen peroxide. Journal of Biochemistry 1989; 105: 429–434
  • Gutteridge J. M.C., Xaio-Chang F. Enhancement of bleomycin-iron free radical damage to DNA by anti oxidants and their mhibition of lipid peroxidation. FEBS Letters 1981; 123: 71–74
  • Porter W. L. Paradoxical behaviour of antioxidants in food and biological systems. Toxicology and Industrial Health 1993; 9: 93–122
  • Mahoney J. R., Graf E. Role of alpha-tocopherol, ascorbic acid, citric acid and EDTA as oxidants in model systems. Journal of Food Science 1986; 51: 1293–1296
  • Aruoma O. I. Pro-oxidant properties: an important consideration for food additives and/or nutrient components?. Free radicals and food additives, O. I. Aruoma, B. Halliwell. Taylor & Francis, London, New York, Philadelphia 1991; 173–194
  • Tassaneeyakul W., Mohamed Z., Birkett D. J., McManus M. E., Veronese M. E., Tukey R. H., Quattrochi L. C., Gonzalez F. J., Miners J. O. Caffeine as a probe for human cytochromes P450 validation using CDNA-expression, immunoinhibition and micrwmal kinetic and Mitor techniques. Pharmacoge-netics 1992; 2: 173–183
  • Tassaneeyakul W., Birkett D. J., McManus M. E., Tassaneeyakul W., Veronese M. E., Andersson T., Tukey R. H., Miners J. O. Caffeine metabolism by human hepatic cytochromes P450: contributions of 1A1, 2E1 and 3A isoforms. Biochmical Pharmacology 1994; 47: 1767–1776

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