Antioxidant activity of phenolic compounds in 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced oxidation: Synergistic and antagonistic effects

  • M. N. Peyrat-MaillardEmail author
  • M. E. Cuvelier
  • C. Berset


Interactions between phenolic antioxidants in binary systems were determined by adding two antioxidants simultaneously in equimolar proportions to an aqueous dispersion of linoleic acid that was then subjected to 2,2′-azobis (2-amidinopropane) dihydrochloride-induced oxidation and by evaluating the protective effect of the antioxidant mixture. The antioxidant power of the mixture was then compared with the expected antioxidant activity calculated by the sum of efficiencies of each compound separately, relative to their proportions in the mixture. If it was higher, a synergy was pointed out whereas a lower value was representative of an antagonism. Thus, synergistic effects were observed between rosmarinic acid and quercetin, or rosmarinic acid and caffeic acid, whereas antagonistic effects were obtained with the following mixtures: α-tocopherol/caffeic acid; α-tocopherol/rosmarinic acid; (+)-catechin/caffeic acid; and caffeic acid/quercetin. These mixture effects are partly explained by regeneration mechanisms between antioxidants, depending on the chemical structure of molecules and on the possible formation of stable intermolecular complexes.

Key Words

AAPH antagonism antioxidant flavonoids phenolic acids synergism α-tocopherol 


  1. 1.
    Shahidi, F., Natural Antioxidants: An Overview, in Natural Antioxidants, Chemistry, Health Effects and Applications, edited by F. Shahidi, AOCS Press, Champaign, 1997, pp. 1–11.Google Scholar
  2. 2.
    Berset, C., and M.E. Cuvelier, Méthodes d’Évaluation du Degré d’Oxydation des Lipides et de Mesure duPouvoir antioxydant, Sci. Aliments 16:219–245 (1996).Google Scholar
  3. 3.
    Liégeois, C., G. Lermusieau, and S. Collin, Measuring Antioxidant Efficiency of Wort, Malt, and Hops Against the 2,2′-Azobis(2-amidinopropane)dihydrochloride-Induced Oxidation of an Aqueous Dispersion of Linoleic Acid, J. Agric. Food Chem. 48:1129–1134 (2000).CrossRefGoogle Scholar
  4. 4.
    Cuvelier, M.E., H. Richard, and C. Berset, Comparison of the Antioxidative Activity of Some Acid-Phenols: Structure-Activity Relationship, Biosci. Biotechnol. Biochem. 56:324–325 (1992).Google Scholar
  5. 5.
    Cuvelier, C., V. Bondet, and C. Berset, Behavior of Phenolic Antioxidants in a Partitioned Medium: Structure-Activity Relationship, J. Am. Oil Chem. Soc. 77:819–823 (2000).Google Scholar
  6. 6.
    Brand-Williams, W., M.E. Cuvelier, and C. Berset, Use of a Free Radical Method to Evaluate Antioxidant Activity, Lebensm. Wiss. Technol. 28:25–30 (1995).Google Scholar
  7. 7.
    Pekkarinen, S.S., I.M. Heinonen, and A.I. Hopia, Flavonoids Quercetin, Myricetin, Kaempferol and (+)-Catechin as Antioxidants in Methyl Linoleate, J. Sci. Food Agric. 79:499–506 (1999).CrossRefGoogle Scholar
  8. 8.
    Terao, J., H. Karasawa, H. Arai, A. Nagao, T. Suzuki, and K. Takama, Peroxyl Radical Scavenging Activity of Caffeic Acid and Its Related Phenolic Compounds in Solution, Biosci. Biotechnol. Biochem. 57:1204–1205 (1993).CrossRefGoogle Scholar
  9. 9.
    Saint-Cricq de Gaulejac, N., N. Vivas, V. de Freitas, and G. Bourgeois, The Influence of Various Phenolic Compounds on Scavenging Activity Assessed by an Enzymatic Method, J. Sci. Food Agric. 79:1081–1090 (1999).CrossRefGoogle Scholar
  10. 10.
    Maillard, M.N., M.E. Cuvelier, and C. Berset, The Antioxidant Activity of Flavonoids and Phenolic Acids: Correlation with Their Chemical Structure; Synergistic and Antagonistic Effects, in Polyphenols Communications, 18th International Conference on Polyphenols (Bordeaux), 15–18 July, 1996, pp. 543–544.Google Scholar
  11. 11.
    Bonnely, S., M.N. Peyrat-Maillard, L. Rondini, D. Masy, and C. Berset, Antioxidant Activity of Malt Rootlets Extracts, J. Agric. Food Chem. 48:2785–2792 (2000).CrossRefGoogle Scholar
  12. 12.
    Povilaityté, V., M.E. Cuvelier, and C. Berset, Antioxidant Properties of Moldavian Dragonhead (Dracocephalum moldavica L.), J. Food Lipids 8:45–64 (2001).Google Scholar
  13. 13.
    Cuppett, S.L., and C.A. Hall, Antioxidant Activity of the Labiatae, Adv. Food Nut. Res. 42:245–271 (1998).CrossRefGoogle Scholar
  14. 14.
    Jia, Z.S., B. Zhou, L. Yang, L.M. Wu, and Z.L. Liu, Antioxidant Synergism of Tea Polyphenols and α-Tocopherol Against Free Radical Induced Peroxidation of Linoleic Acid in Solution, J. Chem. Soc. Perkin Trans. 2:911–915 (1998).Google Scholar
  15. 15.
    Zhu, Q.Y., Y. Huang, D. Tsang, and Z.Y. Chen, Regeneration of α-Tocopherol in Human Low-Density Lipoprotein by Green Tea Catechin, J. Agric. Food Chem. 47:2020–2025 (1999).CrossRefGoogle Scholar
  16. 16.
    Maccarone, E., A. Maccarrone, and P. Rapisarda, Stabilization of Anthocyanins of Blood Orange Fruit Juice, J. Food Sci. 50:901–904 (1985).CrossRefGoogle Scholar
  17. 17.
    Jung, D.M., J.S. de Ropp, and S.E. Ebeler, Study of Interactions Between Food Phenolics and Aromatic Flavors Using One- and Two-Dimensional 1H NMR Spectroscopy, J. Agric. Food Chem. 48:407–412 (2000).CrossRefGoogle Scholar
  18. 18.
    Frankel, E.N., S.W. Huang, J. Kanner, and J.B. German, Interfacial Phenomena in the Evaluation of Antioxidants: Bulk Oil vs. Emulsions, J. Agric. Food Chem. 42:1054–1059 (1994).CrossRefGoogle Scholar
  19. 19.
    Koga, T., and J. Terao, Phospholipids Increase Radical-Scavenging Activity of Vitamin E in a Bulk Oil Model System, J. Agric. Food Chem. 43:1450–1454 (1995).CrossRefGoogle Scholar

Copyright information

© AOCS Press 2003

Authors and Affiliations

  • M. N. Peyrat-Maillard
    • 1
    Email author
  • M. E. Cuvelier
    • 1
  • C. Berset
    • 1
  1. 1.Département Science de l’Aliment, Laboratoire de Chimie des Substances Naturelles: Antioxydants, Arômes, ColorantsEcole Nationale Supérieure des Industries Agricoles et AlimentairesMassy CedexFrance

Personalised recommendations