[Phenolic chain-breaking antioxidants--their activity and mechanisms of action].
This tutorial review is focused on some mechanistic aspects of peroxidation process and chemistry of phenolic chain-breaking antioxidants. Lipids are susceptible to oxidative degradation caused by radicals and during autoxidation (peroxidation) the chain reaction is mediated by peroxyl radicals leading to damage of integrity and the protective and organizational properties of biomembranes. Phenolic antioxidants provide active system of defence against lipid peroxidation, however, the effectiveness of their antioxidant action depends on several important parameters. Stoichiometry of the reaction with free radicals, fate of a phenoxyl radical, polarity of the microenvironment, localization of antioxidant molecules, their concentration and mobility, kinetic solvent effects, and interactions with other co-antioxidants are considered. Principal mechanisms of reaction between phenols and free radicals (Hydrogen Atom Transfer, Proton Coupled Electron Transfer and two mechanisms based on separate electron transfer and proton transfer steps) are described.
Faculty of Chemistry, University of Warsaw, 1 Pasteura St., 02-093 Warsaw, Poland.
Ewelina
E
Kowalewska
Grzegorz
G
Litwinienko
D000375:Aging / Q000378:metabolism; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D005227:Fatty Acids / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006801:Humans; D008053:Lipid Mobilization / Q000502:physiology; D015227:Lipid Peroxidation; D019636:Neurodegenerative Diseases / Q000378:metabolism; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*
D000975:Antioxidants; D005227:Fatty Acids; D005609:Free Radicals; D010636:Phenols; C013584:lipid peroxidation inhibitor