Novel antioxidant reactions of cinnamates in wine

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 11, 2011, Pages 6221-6226

  Gislason, Nick Emil ^a   Currie, Bruce Lamonte ^a   Waterhouse, Andrew Leo ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

, unsaturated side chain; 1 hydroxyethyl radical; allylic alcohol; antioxidant; caffeic acid; cinnamate; ferulic acid; hydroxycinnamate; oxidation; phenolic; radical scavenging; wine

Indexed keywords

1-HYDROXYETHYL RADICAL; ALLYLIC ALCOHOL; ANTIOXIDANT; CAFFEIC ACIDS; CINNAMATES; FERULIC ACIDS; HYDROXYCINNAMATE; PHENOLIC; RADICAL SCAVENGING; SIDE-CHAINS;

CATALYTIC OXIDATION; FREE RADICALS; HYDROGEN; HYDROGEN PEROXIDE; OXIDATION; PHENOLS; SALTS; UNSATURATED COMPOUNDS;

WINE;

ANTIOXIDANT; CINNAMIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; WINE;

ANTIOXIDANTS; CINNAMATES; OXIDATION-REDUCTION; WINE;

EID: 79957988613     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf200115y     Document Type: Article

References (26)

1. Clifford, M. N. Diet derived phenols in plasma and tissues and their implications for health Planta Med. 2004, 70, 1103-1114 (Pubitemid 40109506)
2. Fernandez-Martinez, E.; Bobadilla, R. A.; Morales-Rios, M. S.; Muriel, P.; Perez-Alvarez, P. M. trans -3-Phenyl-2-propenoic acid (cinnamic acid) derivatives: structure-activity relationship as hepatoprotective agents Med. Chem. 2007, 3, 475-479 (Pubitemid 47455738)
3. Bourne, L. C.; Rice-Evans, C. A. The effect of phenolic antioxidant ferulic acid on the oxidation of low density lipoprotein depends on the pro-oxidant used Free Radical Res. 1997, 27, 337-344 (Pubitemid 27474892)
4. Khopde, S. M.; Priyadarsini, K. I.; Guha, S. N.; Mukherjee, T. Hydroxyl radical induced oxidation of 3-methoxy-4-hydroxy cinnamic acid (ferulic acid) Res. Chem. Intermed. 2001, 27, 519-527 (Pubitemid 32828798)
5. Iglesias, J.; Pazos, M.; Andersen, M. L.; Skibsted, L. H.; Medina, I. Caffeic acid as antioxidant in fish muscle: mechanism of synergism with endogerous ascorbic acid and α-tocopherol J. Agric. Food Chem. 2009, 57, 675-681
6. Masuda, T.; Yamada, K.; Maekawa, T.; Takeda, Y.; Tamaguchi, H. Antioxidant mechanism studies on ferulic acid: identification of oxidative coupling products from methyl ferulate and linoleate J. Agric. Food Chem. 2006, 54, 6069-6074 (Pubitemid 44342244)
7. Hapiot, P.; Neudeck, A.; Pinson, J.; Fulcrand, H.; Neta, P.; Rolando, C. Oxidation of caffeic acid and related hydroxycinnamic acids J. Electroanal. Chem. 1996, 405, 169-176 (Pubitemid 126385920)
8. Moon, J. H.; Terao, J. Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein J. Agric. Food Chem. 1998, 46, 5062-5065 (Pubitemid 128488258)
9. Natella, F.; Nardini, M.; Felice, M. D.; Scaccini, C. Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation J. Agric. Food Chem. 1999, 47, 1453-1459 (Pubitemid 29217138)
10. Bobrowski, K.; Raghavan, N. V. Pulse radiolytic and product analysis studies of the reaction of hydroxyl radicals with cinnamic acid. The relative extent of addition to the ring and side chain J. Phys. Chem. 1982, 86, 4432-4435
11. Bobrowski, K. Pulse radiolysis of p -hydroxycinnamic acid in aqueous solution J. Chem. Soc., Faraday Trans. 1 1984, 80, 1377-1389
12. Yadav, P.; Mohan, H.; Maity, D. K.; Suresh, C. H.; Madhav Rao, B. S. Oxidation of cinnamic acid derivatives: a pulse radiolysis and theoretical study Chem. Phys. 2008, 351, 57-64
13. Anouar, E.; Kosinova, P.; Kozlowski, D.; Mokrini, R.; Duroux, J. L.; Trouillas, P. New aspects of the antioxidant properties of phenolic acids: a combined theoretical and experimental approach Phys. Chem. Chem. Phys. 2009, 11, 7659-7668
14. Kennedy, J. A.; Hayasaka, Y.; Vidal, S.; Waters, E. J.; Jones, G. P. Composition of grape skin proanthocyanidins at different stages of berry development J. Agric. Food Chem. 2001, 49, 5348-5355 (Pubitemid 33089676)
15. Danilewicz, J. C.; Seccombe, J. T.; Whelan, J. Mechanism of interaction of polyphenols, oxygen, and sulfur dioxide in model wine and wine Am. J. Enol. Vitic. 2008, 59, 128-136 (Pubitemid 351874266)
16. Danilewicz, J. C. Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: central role of iron and copper Am. J. Enol. Vitic. 2003, 54, 73-85 (Pubitemid 36689421)
17. Singleton, V. L.; Zaya, J.; Trousdale, E. K. Caftaric and coutaric acids in fruit of Vitis Phytochemistry 1986, 25, 2127-2133
18. Elias, R. J.; Laurie, V. F.; Ebeler, S. E.; Wong, J. W.; Waterhouse, A. L. Analysis of selected carbonyl oxidation products in wine by liquid chromatography with diode array detection Anal. Chim. Acta 2008, 626, 104-110
19. Elias, R. J.; Andersen, M. L.; Skibsted, L. H.; Waterhouse, A. L. Identification of free radical intermediates in oxidized wine using electron paramagnetic resonance spin trapping J. Agric. Food Chem. 2009, 57, 4359-4365
20. Fulcrand, H.; Cheminat, A.; Brouillard, R.; Cheynier, V. Characterization of compounds obtained by chemical oxidation of caffeic acid in acidic conditions Phytochemistry 1994, 35, 499-505
21. Rollick, K. L.; Kochi, J. K. Ligand effects on the reduction of iron(III) complexes by alkyl radicals. Formation of alkyl isocyanides and chlorides from cyanoiron(III) and chloroiron(III) species Organometallics 1982, 1, 725-732
22. Rollick, K. L.; Kochi, J. K. Oxidation-reduction mechanisms. Inner sphere and outer sphere electron transfer in the reduction of iron(III), ruthenium(III), and osmium(III) complexes by alkyl radicals J. Am. Chem. Soc. 1982, 104, 1319-1330 (Pubitemid 12499165)
23. 3- J. Chem. Soc., Perkins Trans. 2 1996, 3, 551-556
24. Ballester, M.; Miravitlles, C.; Molins, E.; Carreras, C. Oxidation of the perchlorotriphenylmethyl radical to the carbocation, and its unique abrupt reversion J. Org. Chem. 2003, 68, 2748-2751 (Pubitemid 36512648)
25. Schaller, C.; Klassen, J.; Asmus, L.; Graham, K.; Johnson, B. A mechanistic puzzle: variations on decarboxylative eliminations Chem. Educ. 2001, 6, 10-14
26. Nenadis, N.; Zhang, H. Y.; Tsimidou, M. Z. Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups J. Agric. Food Chem. 2003, 51, 1874-1879