Moderate antioxidative efficiencies of flavonoids during peroxidation of methyl linoleate in homogeneous and micellar solutions

JAOCS, Journal of the American Oil Chemists' Society

Volumn 73, Issue 6, 1996, Pages 777-786

  Roginsky, V A ^a   Barsukova, T K ^a   Remorova, A A ^a   Bors, W ^b  

^a SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

^b INSTITUTE OF EPIDEMIOLOGY   (Germany)

Author keywords

Antioxidants; Azoinitiators; Catechol compounds; Flavonoids; Kinetic study; Methyl linoleate; Oxygen consumption; Peroxidation; Phenols; Relative rate constants

Indexed keywords

CHEMICAL BONDS; INITIATORS (CHEMICAL); MICELLES; MOLECULAR STRUCTURE; OXIDATION; PHENOLS; PLANTS (BOTANY); REACTION KINETICS; STOICHIOMETRY;

AZOINITIATORS; CATECHOL COMPOUNDS; FLAVONOIDS; METHYL LINOLEATE; PEROXIDATION; RELATIVE RATE CONSTANTS;

ANTIOXIDANTS;

EID: 0030163989     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02517955     Document Type: Article

References (44)

1. Das, N.P., and L. Ramanathan, Studies on Flavonoids and Related Compounds as Antioxidants in Food, in Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications, edited by A.S.H. Ong and L. Packer, Birkhäuser Verlag, Basel, 1992, pp. 295-306.
2. Cody, V., E. Middleton, and J.B. Harborne (eds.), Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological, and Structure-Activity Relationship, Alan R. Liss, New York, 1986.
3. Cody V., E. Middleton, J.B., Harborne, and A. Beretz (eds.), Plant Flavonoids in Biology and Medicine II: Biochemical, Cellular and Medicinal Properties, Alan R. Liss, New York, 1988.
4. Stavric, B., and T.I. Matula, Flavonoids in Food: Their Significance for Nutrition and Health, in Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications, edited by A.S.H. Ong and L. Packer, Birkhäuser Verlag, Basel, 1992, pp. 274-294.
5. Middleton, E., and C. Kandaswami, The Impact of Plant Flavonoids on Mammalian Biology: Implications for Immunity, Inflammation, and Cancer, in The Flavonoids: Advances in Research Since 1986, edited by J.B. Harborne, Chapman & Hall, London, 1994, pp. 619-652.
6. Bors, W., W. Heller, C. Michel, and M. Saran, Flavonoids and Polyphenols: Chemistry and Biology, in Handbook on Antioxidants, edited by E. Cadenas, and L. Packer, Marcel Dekker, New York, 1996, pp. 409-466.
7. Bors, W., W. Heller, C. Michel, and M. Saran, Flavonoids as Antioxidants: Determination of Radical-Scavenging Efficiencies, Meth. Enzymol. 186:343-355 (1990).
8. Xin, W.J., B.L. Zhao, X.J. Li, and J.W. Hou, Scavenging Effects of Chinese Herbs and Natural Health Products on Active Oxygen Radicals, Res. Chem. Intermed. 14:171-183 (1990).
9. Bors, W., W. Heller, C. Michel, and M. Saran, Structural Principles of Flavonoid Antioxidants, in Free Radicals and the Liver, edited by G. Csomós and J. Fehér, Springer, Berlin, 1992, pp. 77-94.
10. Afanas'ev, I.B., A.I. Dorozhko, A.V. Brodskii, V.A. Kostyuk, and A.I. Potapovitch, Chelating and Free Radical Scavenging Mechanisms of Inhibitory Action of Rutin and Quercetin in Lipid Peroxidation, Biochem. Pharmacol. 38:1763-1769 (1989).
11. Puppo, A., Effect of Flavonoids on OH Radical Formation by Fenton-Type Reactions: Influence of the Iron Chelator, Phytochemistry 31:85-88 (1992).
12. Morel, I., G. Lescoat, P. Cogrel, O. Sergent, N. Pasdeloup, P. Brissot, P. Cillard, and J. Cillard, Antioxidant and Iron-Chelating Activities of the Flavonoids Catechin, Quercetin and Diosmetin on Iron-Loaded Rat Hepatocyte Cultures, Biochem. Pharmacol. 45:13-19 (1993).
13. Steenken, S., and P. Neta, One-Electron Redox Potentials of Phenols. Hydroxy-and Aminophenols and Related Compounds of Biological Interest, J. Phys. Chem. 86:3661-3667 (1982).
14. Suzuki, N., A. Goto, L. Oguni, S. Mashiko, and T. Nomoto, Reaction Rate Constants of Tea Leaf Catechins with Superoxide: Superoxide-Dismutase (SOD)-Like Activity Measured by Cypridina Luciferin Analogue Chemiluminescence, Chemistry Express 6:655-658 (1991).
15. Erben-Russ, M., C. Michel, W. Bors, and M. Saran, Reactions of Linoleic Acid Peroxyl Radicals with Phenolic Antioxidants: A Pulse Radiolysis Study, Int. J. Radiat. Biol. 52:393-412 (1987).
16. Bors, W., C. Michel, and M. Saran, Flavonoid Antioxidants: Rate Constants for Reactions with Oxygen Radicals, Methods Enzymol. 234:420-429 (1994).
17. Belyakov, V.A., V.A. Roginsky, and W. Bors, Rate Constants for the Reaction of Peroxyl Free Radical with Flavonoids and Related Compounds as Studied by the Kinetic Chemiluminescence Method, J. Chem. Soc., Perkin Trans. II:2319-2326 (1995).
18. Ross, A.B., W.G. Mallard, W.P. Helman, G.V. Buxton, R.E. Huie, and P. Neta, NDRL-NIST Solution Kinetics Database-Version 2, NIST Standard Reference Data, Gaithersburg, 1994.
19. Roginsky, V.A., Phenol Antioxidants. Efficiency and Reactivity. (in Russ.), Nauka, Moscow, 1988.
20. Burton, G.W., and K.U. Ingold, Vitamin E: Application of the Principles of Physical Organic Chemistry to the Exploration of Its Structure and Function, Acc. Chem. Res. 19:194-201 (1986).
21. Pratt, D.E., Role of Flavones and Related Compounds in Retarding Lipid-Oxidative Flavor Changes in Foods, ACS Symp. Ser. 26:1-13 (1976).
22. Affany, A., R. Salvayre, and L. Dousté-Blazy, Comparison of the Protective Effect of Various Flavonoids Against Lipid Peroxidation on Erythrocyte Membranes (induced by cumene hydroperoxide), Fundam. Clin. Pharmacol. 1:451-457 (1987).
23. Ratty, A.K., and N.P. Das, Effects of Flavonoids on Nonenzymatic Lipid Peroxidation: Structure-Activity Relationship, Biochem. Med. Metab. Biol. 39:69-79 (1988).
24. Mora, A., M. Paya, J.L. Rios, and M.J. Alcaraz, Structure-Activity Relationship of Polymethoxyflavonoids and Other Flavonoids as Inhibitors of Non-enzymic Lipid Peroxidation, Biochem. Pharmacol. 40:793-797 (1990).
25. Krol, W., Z. Czuba, S. Scheller, Z. Paradowski, and J. Shani, Structure-Activity Relationship in the Ability of Flavonols to Inhibit Chemiluminescence, J. Ethnopharmacol. 41:121-126 (1994).
26. Terao, J., M. Piskula, and Q. Yao, Protective Effect of Epicatechin, Epicatechin Gallate, and Quercetin on Lipid Peroxidation in Phospholipid Bilayers, Arch. Biochem. Biophys. 308:278-284 (1994).
27. Ioku, K., T. Tsushida, Y. Takei, N. Nakatani, and J. Terao, Antioxidative Activity of Quercetin and Quercetin Monoglucosides in Solution and Phospholipid Bilayers, Biochim. Biophys. Acta 1234:99-104 (1995).
28. Tsepalov, V.F., V.A. Charitonova, G.P. Gladyshev, and N.M. Emanue'I, The Determination of Rate Constants and Inhibition Coefficients for Phenolic Antioxidants by Using a Model Chain Reaction, Kinet. Catal. (in Russ.) 18:1261-1267 (1977).
29. Roginsky, V.A., Kinetics of Oxidation of Polyunsaturated Fatty Acid Esters Inhibited by Substituted Phenols, Ibid, (transl. from Russ.) 31:475-481 (1990).
30. Roginsky, V.A., Effectiveness of Lipid-and Water-Soluble Phenolic Antioxidants in the Oxidation of Polyunsaturated Fatty Acid Esters in Microheterogeous Solutions, Biol. Membr. (transl. from Russ.) 4:437-451 (1990).
31. Burton, G.W., and K.U. Ingold, Autoxidation of Biological Molecules. 1. The Antioxidant Activity of Vitamin E and Related Chain-Breaking Phenolic Antioxidants in vitro, J. Am. Chem. Soc. 103:6472-6477 (1981).
32. Buettner, G.R., In the Absence of Catalytic Metals, Ascorbate Does Not Autoxidize at pH 7: Ascorbate as a Test for Catalytic Metals, J. Biochem. Biophys. Methods 16:27-40 (1988).
33. Roginsky, V.A., and H.B. Stegmann, Kinetics of the Reaction Between Ascorbate and Free Radical from Vitamin E as Studied by ESR Steady-State Method, Chem. Phys. Lipids 65:103-112 (1993).
34. Roginsky, V.A., Thermochemistry, Mechanism, and Kinetics of Disproportionation of Organic Free Radicals, J. Org. Chem. (transl. from Russ.) 25:403-413 (1989).
35. Castle, L., and M.J. Perkins, Inhibition Kinetics of Chain-Breaking Phenolic Antioxidants in SDS Micelles. Evidence That Intermicellar Diffusion Rates May Be Rate-Limiting for Hydrophobic Inhibitors Such as α-Tocopherol, J. Am. Chem. Soc. 108:6381-6382 (1986).
36. Pryor, W.A., T. Strickland, and D.F. Church, Comparison of the Efficiencies of Several Natural and Synthetic Antioxidants in Aqueous SDS Micelle Solutions, Ibid. 110:2224-2229 (1988).
37. Niki, E., Antioxidants in Relation to Lipid Peroxidation, Chem. Phys. Lipids 44:227-253 (1987).
38. Barclay, L.R.C., Model Biomembranes: Quantitative Studies of Peroxidation, Antioxidant Action, Partitioning, and Oxidative Stress, Can. J. Chem. 77:1-16 (1993).
39. Remorova, A.A., and V.A. Roginsky, The Rate Constants for the Reaction of the Phenoxyl Radical from α-Tocopherol with Unsaturated Fatty Esters and the Contribution of This Reaction into the Kinetics of Inhibited Lipid Peroxidation, Kinet. Catal. (transl. from Russ.) 32, 726-731 (1991).
40. Bowry, V.W., and R. Stocker, Tocopherol-Mediated Peroxidation. The Prooxidant Effect of Vitamin E on the Radical-Initiated Oxidation of Human Low-Density Lipoprotein, J. Am. Chem. Soc. 115:6029-6044 (1993).
41. Jovanovic, S.V., S. Steenken, M. Tosic, B. Marjanovic, and M.G. Simic, Flavonoids as Antioxidants, Ibid. 116:4846-4851 (1994).
42. Bors, W., C. Michel, and S. Schikora, Interaction of Flavonoids with Ascorbate and Determination of Their Univalent Redox Potentials: A Pulse Radiolysis Study, Free Rad. Biol. Med. 19:45-52 (1995).
43. Harborne, J.B. (ed.), The Flavonoids: Advances in Research Since 1980, Chapman & Hall, London, 1988.
44. Harborne, J.B. (ed.), The Flavonoids: Advances in Research Since 1986, Chapman & Hall, London, 1994.