Antioxidant behaviour of caffeine: efficient scavenging of hydroxyl radicals.
Considerable controversy exists in the literature regarding the toxicity of coffee, including its possible carcinogenic and anticarcinogenic properties. This study reports on the reaction of 1,3,7-trimethylxanthine (caffeine) with the hydroxyl radical (.OH), as investigated by electron spin resonance (ESR) spin trapping. The .OH was generated by the Fenton reaction (Fe2+ + H2O2) as well as by the reaction of chromium(V) with H2O2. The results show that caffeine effectively scavenges .OH with a reaction rate constant of approximately 5.9 x 10(9) M-1 sec-1 that is comparable with those of other efficient .OH radical scavengers. ESR measurements provide evidence that a caffeine-derived oxygen-centred radical is formed in the reaction of caffeine with .OH and suggest a biochemical basis for the understanding of the reported anticarcinogenic properties of caffeine and related methylxanthine compounds.
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Department of Chemistry, West Virginia University, Morgantown 26506.
Dalal
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Jain
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D000975:Antioxidants / Q000737:chemistry*; D002110:Caffeine / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy; D000431:Ethanol / Q000737:chemistry; D005609:Free Radicals; D006861:Hydrogen Peroxide / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry*; D017665:Hydroxyl Radical; D007501:Iron / Q000737:chemistry; D009249:NADP / Q000737:chemistry
D000975:Antioxidants; D003497:Cyclic N-Oxides; D005609:Free Radicals; D006878:Hydroxides; D017665:Hydroxyl Radical; D002110:Caffeine; D000431:Ethanol; D009249:NADP; C017245:5,5-dimethyl-1-pyrroline-1-oxide; D006861:Hydrogen Peroxide; D007501:Iron