Competitive kinetics in free radical reactions of cinnamic acid derivatives. Influence of phenoxyl radicals reactions

Free Radical Research

Volumn 41, Issue 10, 2007, Pages 1189-1194

  López Alarcón, Camilo ^a   Aspée, Alexis ^b   Lissi, Eduardo ^b  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

Author keywords

Cinnamic acids; Competitive kinetics; Peroxyl radicals; Phenoxyl radicals

Indexed keywords

CAFFEIC ACID; CINNAMIC ACID DERIVATIVE; FERULIC ACID; FREE RADICAL; HYDROGEN; PHENOL DERIVATIVE; SINAPIC ACID;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; DRUG STRUCTURE; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INCUBATION TIME; OXIDATION; PROTEIN TARGETING;

ANTIOXIDANTS; BINDING, COMPETITIVE; BIOCHEMISTRY; CAFFEIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CINNAMATES; FREE RADICALS; HYDROGEN; KINETICS; MODELS, CHEMICAL; OXIDATION-REDUCTION; PHENOLS; REACTIVE OXYGEN SPECIES; TIME FACTORS;

EID: 34748856845     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760701583969     Document Type: Article

References (26)

1. Roginsky, V. and Lissi, E. (2005) Review of methods to determine chain-breaking antioxidant activity in food. Food Chem, 92, pp. 235-254.
2. Lissi, E., Salim-Hanna, M., Faure, M. and Videla, LA. (1991) 2,2′-azobis-(2-amidinopropane) as a radical source for lipid peroxidation and enzyme inactivation studies. Xenobiótica, 21, pp. 995-1001.
3. Niki, E. (1990) Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Meth Enzymol, 186, pp. 100-108.
4. Lissi, E., Pascual, C. and Castillo, M. Del (1992) Luminol luminescence induced by 2,2′-Azo-bis(2-amidinopropane) thermolysis. Free Radic Res Commun, 17, pp. 299-311.
5. Lissi, E., Salim-Hanna, M., Pascual, C. and Castillo, MD. Del (1995) Evaluation of total antioxidant potential (TRAP) and total antioxidant reactivity (TAR) from enhanced chemiluminescence measurements. Free Radic Biol Med, 18, pp. 153-158.
6. Doba, T., Burton, G. and Ingold, K. (1985) Antioxidant and co-antioxidant activity of vitamin C. The effect of vitamin C, either alone or in the presence of vitamin E or a water-soluble vitamin E analogue, upon the peroxidation of aqueous multilamellar phospholipid liposomes. Biochim Biophys Acta, 835, pp. 298-303.
7. Pryor, W., Strickland, T. and Church, D. (1988) Comparison of the efficiencies of several natural and synthetic antioxidants in aqueous sodium dodecyl sulfate micellar solutions. J Am Chem Soc, 110, pp. 2224-2229.
8. Roginsky, V. and Barsukova, T. (2001) Chain-breaking antioxidant capability of some beverages as determined by the Clark technique. J Med Food, 4, pp. 219-229.
9. López-Alarcón, C. and Lissi, E. (2005) Interaction of Pyrogallol red with peroxyl radicals. A basis for a simple methodology for the evaluation of antioxidant capabilities. Free Radic Res, 39, pp. 729-736.
10. López-Alarcón, C. and Lissi, E. (2006) A novel and simple ORAC methodology based on the interaction of Pyrogallol red with peroxyl radicals. Free Radic Res, 40, pp. 979-985.
11. Pino, E. and Lissi, E. (2001) Quantitative treatment of the kinetics of free-radical mediated damage. Protection by free-radical scavengers. Helv Chim Acta, 84, pp. 3677-3685.
12. Lissi, E., Pizarro, M., Aspee, A. and Romay, C. (2000) Kinetics of phycocyanine bilin groups destruction by peroxyl radicals. Free Radic Biol Med, 28, pp. 1051-1055.
13. Cao, G., Alessio, HM and Clutler, RG. (1993) Oxygen-radical absorbance capacity assay for antioxidants. Free Radic Biol Med, 14, pp. 303-311.
14. Hampsch-Woodill, M. and Prior, RL. (2001) Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J Agric Food Chem, 49, pp. 4619-4626.
15. Natella, F., Nardini, M., Giannetti, I., Dattilo, C. and Scaccini, C. (2002) Coffee drinking influences plasma antioxidant capacity in humans. J Agric Food Chem, 50, pp. 6211-6216.
16. Tubaro, F., Gheselli, A., Rapuzzi, P., Maiorino, M. and Ursini, F. (1998) Analysis of plasma antioxidant capacity by competition kinetics. Free Radic Biol Med, 24, pp. 1228-1234.
17. Campos, AM, Sotomayor, CP, Pino, E. and Lissi, E. (2004) A pyranine based procedure for evaluation of the total antioxidant potential (TRAP) of polyphenols. A comparison with closely related methodologies. Biol Res, 37, pp. 287-292.
18. Cheynier, V. and Moutounet, M. (1992) Oxidative reactions of caffeic acid in model systems containing polyphenols oxidase. J Agric Food Chem, 40, pp. 2038-2044.
19. Kader, F., Irmouli, M., Zitouni, N., Nicolas, JP and Metche, M. (1999) Degradation of Cyanin 3-glucoside by caffeic acid o-quinone. Determination of the stoichiometry and characterization of the degradation products. J Agric Food Chem, 47, pp. 4625-4630.
20. Foti, M., Ingold, KU and Lusztyk, J. (1994) The surprinsingly high reactivity of phenoxyl radicals. J Am Chem Soc, 116, pp. 9440-9447.
21. Jackson, R. and Hosseini, K. (1992) Phenol-phenoxyl radical equilibria by electron spin resonance: Are radicals derived from tocopherol and analogues exceptionally stabilized?. J Chem Soc Chem Commun, pp. 967-968.
22. Pino, E., Campos, AM, López-Alarcón, C., Aspée, A. and Lissi, E. (2006) Free radical scavenging capacity of hydroxycinnamic acids and related compounds. J Phys Org Chem, 19, pp. 754-764.
23. Lithoxoidou, A. and Bakalbassis, EG. (2004) Liquid-phase theoretical antioxidant activity trend of some cinnamic acid antioxidants. J Am Oil Chem Soc, 81, pp. 799-802.
24. Mendenhall, GD, Grillerand, D. and Ingold, KU. (1974) Prolonging the life-expectancy of uncongugated organic free radicals. Chem Br, 10, pp. 248-253.
25. Pino, E., Campos, AM and Lissi, E. (2003) 8-Hydroxy-1,3,6-pyrene trisulfonic acid (pyranine) bleaching by 2,2′-azobis(2-amidinopropane) derived peroxyl radicals. Int J Chem Kinet, 35, pp. 525-531.
26. Hanham, AF, Dunn, BP and Stich, HF. (1983) Clastogenic activity of caffeic acid and its relationship to hydrogen peroxide generated during autooxidation. Mutat Res, 116, pp. 333-339.