Redox cycles of caffeic acid, α-tocopherol, and ascorbate: Implications for protection of low-density lipoproteins against oxidation

IUBMB Life

Volumn 48, Issue 1, 1999, Pages 57-65

  Laranjinha, João ^a   Cadenas, Enrique ^b  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

tocopherol; Antioxidants; Ascorbic acid; Atherosclerosis; Caffeic acid; EPR; Low density lipoprotein; Redox cycle; Synergism

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; ASCORBIC ACID; CAFFEIC ACID; FERRYLMYOGLOBIN; LOW DENSITY LIPOPROTEIN; MYOGLOBIN; QUERCETIN; SEMIQUINONE;

ARTICLE; CHEMICAL REACTION KINETICS; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; HUMAN; HUMAN CELL; HUMAN TISSUE; LIPOPROTEIN METABOLISM; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; PROTEIN LOCALIZATION; SEQUENCE ANALYSIS; ULTRAVIOLET IRRADIATION;

ASCORBIC ACID; CAFFEIC ACIDS; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; KINETICS; LIPOPROTEINS, LDL; METMYOGLOBIN; MICELLES; OXIDATION-REDUCTION; ULTRAVIOLET RAYS; VITAMIN E;

EID: 0032744791     PISSN: 15216543     EISSN: None     Source Type: Journal    
DOI: 10.1080/152165499307422     Document Type: Article

References (40)

1. Bors, W., Heller, W., Michel, C., and Slettmaier, K. (1996) Flavonoids and polyphenols: Chemistry and biology. In Handbook of Antioxidants (Cadenas, E., and Packer, L., eds.). pp. 409-4146, Marcel Dekker Inc., New York.
2. Rice-Evans, C. A., and Packer, L. (1998) Flavonoids in Health and Disease. Marcel Dekker Inc., New York.
3. Cuvelier, M. E., Richard, H., and Berset, C. (1992) Comparison of the antioxidative activity of some acid phenols: structure-activity relationship. Biosci. Biotech. Biochem. 56, 324-325.
4. Terao, J., Karasawa, H., Arai, H., Nagao, A., Suzuki, T., and Takama, K. (1993) Peroxyl radical scavenging activity of caffeic acid and its related phenolic compounds in solution. Biosci. Biotech. Biochem. 57, 1204-1205.
5. Laranjinha, J., Almeida, L., and Madeira, V. (1994) Reactivity of dietary phenolic acids with peroxyl radicals: Antioxidant activity upon low-density lipoprotein peroxidation. Biochem. Pharmacol. 48, 487-494.
6. Vieira, O., Escargueil-Blanc, I., Meilhac, O., Basile, J. P., Laranjinha, J., Almeida, L., Salvayre, R., and Negre-Salvayre, A. (1998) Effect of dietary phenolic compounds on apoptosis of human cultured endothelial cells induced by oxidized LDL. Br. J. Pharmacol. 123, 565-573.
7. Bors, W., Heller, W., Christa, M., and Saran, M. (1990) Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods Enzymol. 186, 343-355.
8. Rice-Evans, C. A., and Miller, N. J. (1998) Structure-antioxidant activity relationships of flavonoids and isoflavonoids. In Flavonoids in Health and Disease (Rice-Evans, C., and Packer, L., eds.). pp. 199-219, Marcel Dekker Inc., New York.
9. Heller, W., and Forkman, G. (1993) Biosynthesis of flavonoids. In The Flavonoids: Advances in Research Since 1986 (Harborne, J. B., ed.). pp. 499-535, Chapman & Hall, London.
10. 2-dependent low-density lipoprotein lipid peroxidation by naturally occurring phenolic acids. Biochem. Pharmacol. 51, 395-402.
11. Belyakov, V. A., Roginsky, V. V., and Bors, W. (1995) Rate constants for the reaction of peroxyl free radical with flavonoids and related compounds as determined by the kinetic chemiluminescence method. J. Chem. Soc. Perkin II, 2319-2325.
12. Laranjinha, J. A., Almeida, L. M., and Madeira, V. M. (1992) Lipid peroxidation and its inhibition in low-density lipoproteins: quenching of cis-parinaric acid fluorescence. Arch. Biochem. Biophys. 297, 147-154.
13. Kono, Y., Kobayashi, K., Tagawa, S., Adachi, K., Ueda, A., Sawa, Y., and Shibata, H. (1997) Antioxidant activity of polyphenolics in diets. Rate constants of reactions of chlorogenic acid and caffeic acid with reactive species of oxygen and nitrogen. Biochim. Biophys. Acta 1335, 335-342.
14. Laranjinha, J., Vieira, O., Madeira, V., and Almeida, L. (1995) Two related phenolic antioxidants with opposite effects on vitamin E content in low-density lipoproteins oxidized by ferrylmyoglobin: consumption vs regeneration. Arch. Biochem. Biophys. 323, 373-381.
15. Giulivi, C., Romero, F. J., and Cadenas, E. (1992) The interaction of Trolox C, a water-soluble vitamin E analog, with ferrylmyoglobin. Reduction of the oxoferryl moiety. Arch. Biochem. Biophys. 299, 302-312.
16. Vieira, O. V., Laranjinha, J. A., Madeira, V., and Almeida, L. M. (1996) Rapid isolation of low-density lipoproteins in a concentrated fraction free from water-soluble plasma antioxidants. J. Lipid Res. 37, 2715-2721.
17. Esterbauer, H., Dieber-Rotheneder, M., Striegl, G., and Waeg, G. (1991) Role of vitamin E in preventing the oxidation of low-density lipoprotein. Am. J. Clin. Nutr. 53, 314S-321S.
18. Burton, G. W., Webb, A., and Ingold, K. U. (1985) A mild, rapid, and efficient method of lipid extraction for use in determining vitamin E/lipid ratios. Lipids 20, 29-39.
19. Ashworth, P. (1976) Electron spin resonance studies of structure and conformation in anion radicals formed during the autoxidation of hydroxylated coumarins. J. Org. Chem. 41, 2920-2924.
20. Mehlhorn, R. J., Fuchs, J., Sumida, S., and Packer, L. (1990) Preparation of tocopheroxyl radicals for detection by electron spin resonance. Methods Enzymol. 186, 197-205.
21. Bisby, R. H., and Parker, A. W. (1995) Reaction of ascorbate with the α-tocopheroxyl radical in micellar and bilayer membrane systems. Arch. Biochem. Biophys. 317, 170-178.
22. Witting, P. K., Westerlund, C., and Stocker, R. (1996) A rapid and simple screening test for potential inhibitors of tocopherol-mediated peroxidation of LDL lipids. J. Lipid Res. 37, 853-867.
23. Buettner, G. R., and Jurkiewicz, B. A. (1993) Ascorbate free radical as a marker of oxidative stress: an EPR study. Free Radicals-Biol. Med. 14, 49-55.
24. Jovanovic, S. V., Sleenken, S., Tosic, M., Marjanovic, B., and Simic, M. G. (1994) Flavonoids as antioxidants. J. Am. Chem. Soc. 116, 4846-4851.
25. Bors, W., Michel, C., and Schikora, S. (1995) Interaction of flavonoids with ascorbate and determination of their univalent redox potentials: A pulse radiolysis study. Free Radic. Biol. Med. 19, 45-52.
26. Giulivi, C., and Cadenas, E. (1993) The reaction of ascorbic acid with different heme iron redox states of myoglobin. FEBS Lett. 332, 287-290.
27. Buettner, G. R. (1980) Ascorbate oxidation: UV absorbance of ascorbate and ESR spectroscopy of the ascorbyl radical as assays for iron. Free Radic. Res. Commun. 10, 5-9.
28. Buettner, G. R., and Jurkiewicz, B. A. (1996) Chemistry and biochemistry of ascorbic acid. In Handbook of Antioxidants (Cadenas, E., and Packer, L., eds.). pp. 91-115, Marcel Dekker Inc., New York.
29. Satoh, K., and Sakagami, H. (1996) Ascorbyl radical scavenging activity of polyphenols. Anticancer Res. 16, 2885-2890.
30. Vieira, O. V., Laranjinha, J., Madeira, V., and Almeida, L. (1998) Cholesteryl ester hydroperoxide formation in myoglobin-catalyzed low density lipoprotein oxidation: concerted antioxidant activity of caffeic and p-coumaric acids with ascorbate. Biochem. Pharmacol. 55, 333-340.
31. Terao, J., and Piskula, M. K. (1998) Flavonoids as inhibitors of lipid peroxidation in membranes. In Flavonoids in Health and Disease (Ricc-Evans, C., and Packer, L., eds.). pp. 277-293, Marcel Dekker Inc., New York.
32. Roginsky, V. A., Barsukova, T. K., Remorova, A. A., and Bors, W. (1996) Moderate antioxidative efficiencies of flavonoids during peroxidation of methyl linoleate in homogeneous and micellar solutions. J. Am. Oil Chem. Soc. 73, 777-786.
33. Antunes, F., Salvador, A., Marinho, H. S., Alves, R. and Pinto, R. E. (1996) Lipid peroxidation in mitochondrial inner membranes. I. An integrative kinetic model. Free Radic. Biol. Med. 21, 917-943.
34. Maiani, G., Serafini, M., Salucci, M., Azzini, E., and Ferro-Luzzi, A. (1997) Application of a new high-performance liquid chromatographic method for measuring selected polyphenols in human plasma. J. Chromatogr. B. Biomed. Sci. Appl. 692, 311-317.
35. Nardini, M., Natella, F., Gentili, V. DiFelici, M., and Scaccini, C. (1997) Effect of caffeic acid dietary supplementation on the antioxidant defense system in rat: an in vivo study. Arch. Biochem. Biophys. 342, 157-160.
36. 2+)-oxidizability: Possible explanation by phenolic location. Eur. J. Clin. Nutr. 51, 682-690.
37. Takahama, U., and Onoki, T. (1994) Effects of ascorbate on the oxidation of derivatives of hydroxycinnamic acid and the mechanism of oxidation of sinapic acid by cell wall-bound peroxidases. Plant Cell Physiol. 35, 593-600.
38. 2+). J. Phys. Chem. 88, 99-101.
39. Giulivi, C., and Cadenas, E. (1994) Ferrylmyoglobin: Formation and chemical reactivity toward electron-donating compounds. Methods Enzymol. 233, 189-202.
40. Giulivi, C., and Cadenas, E. (1997) Myoblobin protein radicals: Formation, fate, and biological consequence. Free Radic. Biol. Med. 24, 269-279.