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BioMed Research International
Volume 2013 (2013), Article ID 251754, 11 pages
Hydroxycinnamic Acid Antioxidants: An Electrochemical Overview
1CIQ/Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal
2Departamento de Engenharia Química, Instituto Superior de Engenharia do Porto (ISEP), Instituto Politécnico do Porto, 4200-072 Porto, Portugal
Received 30 April 2013; Accepted 18 June 2013
Academic Editor: Kent M. Reed
Copyright © 2013 José Teixeira et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- P. A. Kroon and G. Williamson, “Hydroxycinnamates in plants and food: current and future perspectives,” Journal of the Science of Food and Agriculture, vol. 79, no. 3, pp. 355–361, 1999.
- F. Shahidi and A. Chandrasekara, “Hydroxycinnamates and their in vitro and in vivo antioxidant activities,” Phytochemistry Reviews, vol. 9, no. 1, pp. 147–170, 2010.
- P. Fresco, F. Borges, C. Diniz, and M. P. M. Marques, “New insights on the anticancer properties of dietary polyphenols,” Medicinal Research Reviews, vol. 26, no. 6, pp. 747–766, 2006.
- N. Razzaghi-Asl, J. Garrido, H. Khazraei, F. Borges, and O. Firuzi, “Antioxidant properties of hydroxycinnamic acids: a review of structure-activity relationships,” Current Medicinal Chemistry. In press.
- C. A. Rice-Evans, N. J. Miller, and G. Paganga, “Structure-antioxidant activity relationships of flavonoids and phenolic acids,” Free Radical Biology and Medicine, vol. 20, no. 7, pp. 933–956, 1996.
- D. Galato, K. Ckless, M. F. Susin, C. Giacomelli, R. M. Ribeiro-do-Valle, and A. Spinelli, “Antioxidant capacity of phenolic and related compounds: correlation among electrochemical, visible spectroscopy methods and structure-antioxidant activity,” Redox Report, vol. 6, no. 4, pp. 243–250, 2001.
- A. Gaspar, E. M. Garrido, M. Esteves et al., “New insights into the antioxidant activity of hydroxycinnamic acids: synthesis and physicochemical characterization of novel halogenated derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 5, pp. 2092–2099, 2009.
- F. M. F. Roleira, C. Siquet, E. Orr et al., “Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties,” Bioorganic and Medicinal Chemistry, vol. 18, no. 16, pp. 5816–5825, 2010.
- J. Garrido, A. Gaspar, E. M. Garrido et al., “Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress,” Biochimie, vol. 94, no. 4, pp. 961–967, 2012.
- A. Gaspar, M. Martins, P. Silva et al., “Dietary phenolic acids and derivatives. Evaluation of the antioxidant activity of sinapic acid and its alkyl esters,” Journal of Agricultural and Food Chemistry, vol. 58, no. 21, pp. 11273–11280, 2010.
- J. Teixeira, T. Silva, S. Benfeito et al., “Exploring nature profits: development of novel and potent lipophilic antioxidants based on galloyl—cinnamic hybrids,” European Journal of Medicinal Chemistry, vol. 62, pp. 289–296, 2013.
- T. Nguyen, P. J. Sherratt, and C. B. Pickett, “Regulatory mechanisms controlling gene expression mediated by the antioxidant response element,” Annual Review of Pharmacology and Toxicology, vol. 43, pp. 233–260, 2003.
- R. Rodrigo, A. Miranda, and L. Vergara, “Modulation of endogenous antioxidant system by wine polyphenols in human disease,” Clinica Chimica Acta, vol. 412, no. 5-6, pp. 410–424, 2011.
- J. K. Jacob, K. Tiwari, J. Correa-Betanzo, A. Misran, R. Chandrasekaran, and G. Paliyath, “Biochemical basis for functional ingredient design from fruits,” Annual Review of Food Science Technology, vol. 3, pp. 79–104, 2012.
- C. M. A. Brett and A. M. Oliveira Brett, Electrochemistry: Principles, Methods and Applications, Oxford University Press, Oxford, UK, 1993.
- A. J. Bard and L. R. Faulkner, Electrochemical Methods: Fundamentals and Applications, Wiley, New York, 2001.
- S. P. Kounaves, “Voltammetric techniques,” in Handbook of Instrumental Techniques for Analytical Chemistry, F. A. Settle, Ed., Prentice Hall, Upper Saddle River, NJ, USA, 1997.
- R. Greef, R. Peat, L. M. Peter, D. Pletcher, and J. Robinson, Instrumental Methods in Electrochemistry, Ellis Horwood, Chichester, UK, 1985.
- G. Denuault, M. Sosna, and K. J. Williams, “Classical experiments,” in Handbook of Electrochemistry, C. G. Zoski, Ed., Elsevier, Amsterdam, The Netherlands, 2007.
- G. Denuault, “Electrochemical techniques and sensors for ocean research,” Ocean Science, vol. 5, no. 4, pp. 697–710, 2009.
- E. M. Becker, L. R. Nissen, and L. H. Skibsted, “Antioxidant evaluation protocols: food quality or health effects,” European Food Research and Technology, vol. 219, no. 6, pp. 561–571, 2004.
- B. Halliwell, “How to characterize a biological antioxidant,” Free Radical Research Communications, vol. 9, no. 1, pp. 1–32, 1990.
- B. Halliwell, “Antioxidants: the basics—what they are and how to evaluate them,” Advances in Pharmacology, vol. 38, pp. 3–20, 1997.
- D. Huang, O. U. Boxin, and R. L. Prior, “The chemistry behind antioxidant capacity assays,” Journal of Agricultural and Food Chemistry, vol. 53, no. 6, pp. 1841–1856, 2005.
- S. Chevion and M. Chevion, “Antioxidant status and human health. Use of cyclic voltammetry for the evaluation of the antioxidant capacity of plasma and of edible plants,” Annals of the New York Academy of Sciences, vol. 899, pp. 308–325, 2000.
- S. Chevion, M. A. Roberts, and M. Chevion, “The use of cyclic voltammetry for the evaluation of antioxidant capacity,” Free Radical Biology and Medicine, vol. 28, no. 6, pp. 860–870, 2000.
- A. J. Blasco, A. G. Crevillén, M. C. González, and A. Escarpa, “Direct electrochemical sensing and detection of natural antioxidants and antioxidant capacity in vitro systems,” Electroanalysis, vol. 19, no. 22, pp. 2275–2286, 2007.
- P. Hapiot, A. Neudeck, J. Pinson, H. Fulcrand, P. Neta, and C. Rolando, “Oxidation of caffeic acid and related hydroxycinnamic acids,” Journal of Electroanalytical Chemistry, vol. 405, no. 1-2, pp. 169–176, 1996.
- W. R. Sousa, C. da Rocha, C. L. Cardoso, D. H. S. Silva, and M. V. B. Zanoni, “Determination of the relative contribution of phenolic antioxidants in orange juice by voltammetric methods,” Journal of Food Composition and Analysis, vol. 17, no. 5, pp. 619–633, 2004.
- P. Janeiro, I. Novak, M. Seruga, and A. M. Oliveira-Brett, “Electroanalytical oxidation of p-coumaric acid,” Analytical Letters, vol. 40, no. 17, pp. 3309–3321, 2007.
- A. Simić, D. Manojlović, D. Šegan, and M. Todorović, “Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics,” Molecules, vol. 12, no. 10, pp. 2327–2340, 2007.
- H. Lund and M. M. Baizer, Organic Electrochemistry, Marcel Dekker, New York, NY, USA, 3rd edition, 1991.
- C. Giacomelli, K. Ckless, D. Galato, F. S. Miranda, and A. Spinelli, “Electrochemistry of caffeic acid aqueous solutions with pH 2.0 to 8.5,” Journal of the Brazilian Chemical Society, vol. 13, no. 3, pp. 332–338, 2002.
- S. K. Trabelsi, N. B. Tahar, B. Trabelsi, and R. Abdelhedi, “Electrochemical oxidation of ferulic acid in aqueous solutions at gold oxide and lead dioxide electrodes,” Journal of Applied Electrochemistry, vol. 35, no. 10, pp. 967–973, 2005.
- N. Nenadis, S. Boyle, E. G. Bakalbassis, and M. Tsimidou, “An experimental approach to structure-activity relationships of caffeic and dihydrocaffeic acids and related monophenols,” Journal of the American Oil Chemists' Society, vol. 80, no. 5, pp. 451–458, 2003.
- M. Born, P.-A. Carrupt, R. Zini et al., “Electrochemical behaviour and antioxidant activity of some natural polyphenols,” Helvetica Chimica Acta, vol. 79, no. 4, pp. 1147–1158, 1996.
- A. Neudörffer, D. Bonnefont-Rousselot, A. Legrand, M.-B. Fleury, and M. Largeron, “4-Hydroxycinnamic ethyl ester derivatives and related dehydrodimers: relationship between oxidation potential and protective effects against oxidation of low-density lipoproteins,” Journal of Agricultural and Food Chemistry, vol. 52, no. 7, pp. 2084–2091, 2004.
- W. Brand-Williams, M. E. Cuvelier, and C. Berset, “Use of a free radical method to evaluate antioxidant activity,” LWT-Food Science and Technology, vol. 28, no. 1, pp. 25–30, 1995.
- F. A. M. Silva, F. Borges, C. Guimarães, J. L. F. C. Lima, C. Matos, and S. Reis, “Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters,” Journal of Agricultural and Food Chemistry, vol. 48, no. 6, pp. 2122–2126, 2000.
- C. Siquet, F. Paiva-Martins, J. L. F. C. Lima, S. Reis, and F. Borges, “Antioxidant profile of dihydroxy- and trihydroxyphenolic acids—a structure-activity relationship study,” Free Radical Research, vol. 40, no. 4, pp. 433–442, 2006.
- C. Bocchi, M. Careri, F. Groppi, A. Mangia, P. Manini, and G. Mori, “Comparative investigation of UV, electrochemical and particle beam mass spectrometric detection for the high-performance liquid chromatographic determination of benzoic and cinnamic acids and of their corresponding phenolic acids,” Journal of Chromatography A, vol. 753, no. 2, pp. 157–170, 1996.
- J. A. Kennedy and A. L. Waterhouse, “Analysis of pigmented high-molecular-mass grape phenolics using ion- pair, normal-phase high-performance liquid chromatography,” Journal of Chromatography A, vol. 866, no. 1, pp. 25–34, 2000.
- S. A. Lazarus, G. E. Adamson, J. F. Hammerstone, and H. H. Schmitz, “High-performance liquid chromatography/mass spectrometry analysis of proanthocyanidins in foods and beverages,” Journal of Agricultural and Food Chemistry, vol. 47, no. 9, pp. 3693–3701, 1999.
- S. F. Price, P. J. Breen, M. Valladao, and B. T. Watson, “Cluster sun exposure and quercetin in Pinot noir grapes and wine,” American Journal of Enology and Viticulture, vol. 46, no. 2, pp. 187–194, 1995.
- M. Ibern-Gómez, C. Andrés-Lacueva, R. M. Lamuela-Raventós, and A. L. Waterhouse, “Rapid HPLC analysis of phenolic compounds in red wines,” American Journal of Enology and Viticulture, vol. 53, no. 3, pp. 218–221, 2002.
- V. Castaignède, H. Durliat, and M. Comtat, “Amperometric and potentiometric determination of catechin as model of polyphenols in wines,” Analytical Letters, vol. 36, no. 9, pp. 1707–1720, 2003.
- V. Parra, T. Hernando, M. L. Rodríguez-Méndez, and J. A. De Saja, “Electrochemical sensor array made from bisphthalocyanine modified carbon paste electrodes for discrimination of red wines,” Electrochimica Acta, vol. 49, no. 28, pp. 5177–5185, 2004.
- D. De Beer, J. F. Harbertson, P. A. Kilmartin et al., “Phenolics: a comparison of diverse analytical methods,” American Journal of Enology and Viticulture, vol. 55, no. 4, pp. 389–400, 2004.
- J. Piljac, S. Martinez, T. Stipčević, Ž. Petrović, and M. Metikoš-Huković, “Cyclic voltammetry investigation of the phenolic content of croatian wines,” American Journal of Enology and Viticulture, vol. 55, no. 4, pp. 417–422, 2004.
- V. Roginsky, D. De Beer, J. F. Harbertson, P. A. Kilmartin, T. Barsukova, and D. O. Adams, “The antioxidant activity of Californian red wines does not correlate with wine age,” Journal of the Science of Food and Agriculture, vol. 86, no. 5, pp. 834–840, 2006.
- O. Makhotkina and P. A. Kilmartin, “The use of cyclic voltammetry for wine analysis: determination of polyphenols and free sulfur dioxide,” Analytica Chimica Acta, vol. 668, no. 2, pp. 155–165, 2010.
- R. C. Martins, R. Oliveira, F. Bento et al., “Oxidation management of white wines using cyclic voltammetry and multivariate process monitoring,” Journal of Agricultural and Food Chemistry, vol. 56, no. 24, pp. 12092–12098, 2008.
- S. C. Petrovic, “Correlation of perceived wine astringency to cyclic voltammetric response,” American Journal of Enology and Viticulture, vol. 60, no. 3, pp. 373–378, 2009.
- A. S. Arribas, M. Martínez-Fernández, and M. Chicharro, “The role of electroanalytical techniques in analysis of polyphenols in wine,” Trends in Analytical Chemistry, vol. 34, pp. 78–96, 2012.
- M. Hilgemann, V. C. Bassetto, and L. T. Kubota, “Electrochemical approaches employed for sensing the antioxidant capacity exhibited by vegetal extracts: a review,” Combinatorial Chemistry & High Throughput Screen, vol. 16, no. 2, pp. 98–108, 2013.
- E. N. Frankel, A. L. Waterhouse, and P. L. Teissedre, “Principal phenolic phytochemicals in selected California wines and their antioxidant activity in inhibiting oxidation of human low-density lipoproteins,” Journal of Agricultural and Food Chemistry, vol. 43, no. 4, pp. 890–894, 1995.
- P. A. Kilmartin and C. F. Hsu, “Characterisation of polyphenols in green, oolong, and black teas, and in coffee, using cyclic voltammetry,” Food Chemistry, vol. 82, no. 4, pp. 501–512, 2003.
- W. J. R. Santos, M. Santhiago, I. V. P. Yoshida, and L. T. Kubota, “Novel electrochemical sensor for the selective recognition of chlorogenic acid,” Analytica Chimica Acta, vol. 695, no. 1-2, pp. 44–50, 2011.
- Á. M. Alonso, C. Domínguez, D. A. Guillén, and C. G. Barroso, “Determination of antioxidant power of red and white wines by a new electrochemical method and its correlation with polyphenolic content,” Journal of Agricultural and Food Chemistry, vol. 50, no. 11, pp. 3112–3115, 2002.
- P. A. Kilmartin, H. Zou, and A. L. Waterhouse, “A cyclic voltammetry method suitable for characterizing antioxidant properties of wine and wine phenolics,” Journal of Agricultural and Food Chemistry, vol. 49, no. 4, pp. 1957–1965, 2001.
- J. Dobes, O. Zitka, J. Sochor et al., “Electrochemical tools for determination of phenolic compounds in plants: a review,” International Journal of Electrochemical Science, vol. 8, pp. 4520–4542, 2013.