Antioxidant synergy and regeneration effect of quercetin, (-)-epicatechin, and (+)-catechin on α-tocopherol in homogeneous solutions of peroxidating methyl linoleate

Journal of Agricultural and Food Chemistry

Volumn 50, Issue 24, 2002, Pages 7138-7144

  Pedrielli, Pamela ^a   Skibsted, Leif H ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Tocopherol; (+) Catechin; ( ) Epicatechin; Antioxidants; Quercetin; Regeneration; Solvent effect; Synergism

Indexed keywords

ALPHA TOCOPHEROL; ALPHA,ALPHA' AZOISOBUTYRONITRILE; ANTIOXIDANT; CATECHIN; CHLOROBENZENE; EPICATECHIN; FLAVONOID; ISOBUTYL NITRITE; LINOLEIC ACID; LINOLEIC ACID METHYL ESTER; QUERCETIN; SOLVENT; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMISTRY; DRUG POTENTIATION; ELECTRON SPIN RESONANCE; HYDROGEN BOND; LIPID PEROXIDATION; OXIDATION REDUCTION REACTION; OXIMETRY; OXYGEN CONCENTRATION; REGENERATION; SOLUTION AND SOLUBILITY; STOICHIOMETRY;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; CATECHIN; CHLOROBENZENES; DRUG SYNERGISM; ELECTRON SPIN RESONANCE SPECTROSCOPY; LINOLEIC ACIDS; OXIDATION-REDUCTION; QUERCETIN; SOLUTIONS; SOLVENTS; TERT-BUTYL ALCOHOL;

EID: 0037145880     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020437l     Document Type: Article

References (32)

1. Hertog, M. G. L.; Hollman, P. C. H.; Katan, M. B.; Kromhout, D. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands. Nutr. Cancer 1993, 20, 21-29.
2. Rajalakshmi, D.; Narasimhau, S. Food antioxidants: Sources and methods of evaluation. In Food Antioxidants; Madhavi, D. L., Deshpande, S. S., Salunkhe, D. K., Eds.; Marcel Dekker: New York, 1996; pp 65-157.
3. Bravo, L. Polyphenols: Chemistry, dietary sources, metabolism, and nutritional significance. Nutr. Rev. 1998, 56, 317-333.
4. Bors, W.; Heller, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods Enzymol. 1990, 186, 343-355.
5. Bors, W.; Michel, C. Antioxidant capacity of flavanols and gallate esters: Pulse radiolysis studies. Free Radical Biol. Med. 1999, 27, 1413-1426.
6. Foti, M.; Ruberto, G. Kinetic solvent effects on phenolic antioxidants determined by spectrophotometric measurements. J. Agric. Food Chem. 2001, 49, 342-348.
7. Pedrielli, P.; Pedulli, G. F.; Skibsted, L. H. Antioxidant mechanism of flavonoids. Solvent effect on rate constant for chain-breaking reaction of quercetin and epicatechin in autoxidation of methyl linoleate. J. Agric. Food Chem. 2001, 49, 3034-3040.
8. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. Kinetic solvent effects on hydroxylic hydrogen atom abstractions are independent of the nature of the abstracting radical. Two extreme tests using vitamin E and phenol. J. Am. Chem. Soc. 1995, 117, 9966-9971.
9. Harbone, J. B. Nature, distribution, and function of plant flavonoids. In Plant Flavonoids in Biology and Medicine: Biochemical, Phamacological, and Structure-Activity Relationship; Cody, V., Middleton, E., Harbone, J. B., Eds.; Alan R. Liss: New York, 1986; pp 15-24.
10. Pekkarinen, S. S.; Heinonen, I. M.; Hopia A. I. Flavonoids quercetin, myricetin, kaemferol and (+)-catechin as antioxidants in methyl linoleate. J. Sci. Food Agric. 1999, 79, 499-506.
11. Zhu, Q. Y.; Huang, Y.; Tsang, D.; Chen, Z.-Y. Regeneration of α-tocopherol in human low-density lipoprotein by green tea catechin. J. Agric. Food Chem. 1999, 47, 2020-2025.
12. Jia, Z.-S.; Zhou, B.; Yang, L.; Wu, L.-M.; Liu, Z.-L. Antioxidant synergism of tea polyphenols and α-tocopherol against free radical induced peroxidation of linoleic acid in solution. J. Chem. Soc., Perkin Trans. 2 1998, 4, 911-915.
13. Jovanovic, S. V.; Steenken, S.; Hara, Y.; Simic, M. G. Reduction potentials of flavonoid and model phenoxyl radicals. Which ring in flavonoids is responsible for antioxidant activity? J. Chem. Soc., Perkin Trans. 2 1996, 11, 2497-2504.
14. Barclay, L. R. C.; Locke, S. J.; MacNeil, J. M. Autoxidation in micelles. Synergism of vitamin C with lipid-soluble vitamin E and water-soluble Trolox. Can. J. Chem. 1985, 63, 366-374.
15. Bisby, R. H.; Parker, A. W. Reaction of ascorbate with the α-tocopheroxyl radical in micellar and bilayer membrane systems. Arch. Biochem. Biophys. 1995, 317 (1), 170-178.
16. Niki, E.; Saito, T.; Kawakami, A.; Kamiya, Y. Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. J. Biol. Chem. 1984, 259 (7), 4177-4182.
17. Jørgensen, L. V.; Madsen, H. L.; Thomsen, M. K.; Dragsted, L. O.; Skibsted, L. H. Regeneration of phenolic antioxidants from I phenoxyl radicals: An ESR and electrochemical study of antioxidant hierarchy. Free Radical Res. 1999, 30, 207-220.
18. Pedulli, G. F.; Lucarini, M.; Pedrielli, P.; Sagrini, M.; Cipollone, M. The determination of the oxygen consumption in autoxidation studies by means of EPR spectroscopy. Res. Chem. Intermed. 1996, 22, 1-14.
19. Pedulli, G. F. Stable radicals as probes of the oxygen concentration in autoxidation studies. In Free Radicals and Antioxidants in Nutrition; Corongiu, F., Banni, S., Dessi, M. A., Rice-Evans, C., Eds.; Richelieu Press: London, 1993; pp 169-185.
20. Wilhelm, E.; Battino, R. Thermodynamics functions of the solubilities of gases in liquids at 25°C. Chem. Rev. 1973, 73, 1-9.
21. Burton, G. W.; Ingold, K. U. Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. J. Am. Chem. Soc. 1981, 103, 6472-6477.
22. Mukai, K.; Oka, W.; Watanabe, K.; Egawa, Y.; Nagaoka, S.-I.; Terao, J. Kinetic study of free-radical -scavenging action of flavonoids in homogeneous and aqueous triton X-100 micellar solutions. J. Phys. Chem. A 1997, 101, 3746-3753.
23. Mukai, K.; Kanesaki, Y.; Egawa, Y.; Nagaoka, S.-I. Free radical-scavenging action of catechin and related compounds in homogeneous and micellar solutions. In Phytochemicals and Phytopharmaceuticals; Shahidi, F., Ho, C. T., Eds.; AOCS Press: Champaign, IL, 1998; pp 222-238.
24. Niki, E.; Watanabe, A.; Noguchi, N. Reduction of α-tocopheroxyl radical by natural antioxidants. The Second International Symposium on Natural Antioxidants (ISNA): Molecular Mechanisms and Health Effects, June 4-8, 2001, Beijing, China, Programme and Abstracts, p 18.
25. Valgimigli, L.; Banks, J. T.; Lusztyk, J.; Ingold, K. U. Solvent effects on the antioxidant activity of vitamin E. J. Org. Chem. 1999, 64, 3381-3383.
26. Foti, M.; Ingold, K. U.; Lusztyk, J. The surprisingly high reactivity of phenoxyl radicals. J. Am. Chem. Soc. 1994, 116, 9440-9447.
27. Roginsky, V. A.; Barsukova, T. K.; Remorova, A. A.; Bors, W. Moderate antioxidative efficiencies of flavonoids during peroxidation of methyl linoleate in homogeneous and micellar solutions. J. Am. Oil Chem. Soc. 1996, 73, 777-786.
28. Jørgensen, L. V.; Cornett, C.; Justesen, U.; Skibsted, L. H.; Dragsted, L. O. Two-electron electrochemical oxidation of quercetin and kaempferol changes only the flavonoid C-ring. Free Radical Res. 1998, 29, 339-350.
29. Pedrielli, P.; Holkeri, L. M.; Skibsted, L. H. Antioxidant activity of (+)-catechin. Rate constant for hydrogen-atom transfer to peroxyl radicals. Eur. Food Res. Technol. 2001, 213, 405-408.
30. Lucarini, M.; Mugnaini, V.; Pedulli, G. F. Bond dissociation enthalpies of polyphenols: The importance of cooperative effects. J. Org. Chem. 2002, 67, 928-931.
31. Landi, L.; Cabrini, L.; Fiorentini, D.; Stefanelli, C.; Pedulli, G. F. The antioxidant activity of ubiquinol-3 in homogeneous solution and in liposomes. Chem. Phys. Lipids 1992, 61, 121-130.
32. Bowry, V. W.; Ingold, K. U. Extraordinary kinetic-behavior of the alpha-tocopheroxyl (vitamin-E) radical. J. Org. Chem. 1995, 60, 5456-5467.