Effects of caffeic acid and bovine serum albumin in reducing the rate of development of rancidity in oil-in-water and water-in-oil emulsions
Conde, E., Gordon, M. H., Moure, A. and Dominguez, H. (2011) Effects of caffeic acid and bovine serum albumin in reducing the rate of development of rancidity in oil-in-water and water-in-oil emulsions. Food Chemistry, 129 (4). pp. 1652-1659. ISSN 0308-8146
To link to this article DOI: 10.1016/j.foodchem.2011.06.027
The antioxidant properties of caffeic acid and bovine serum albumin in oil-in-water and water-in-oil emulsions were studied. Caffeic acid (5 mmol/kg emulsion) showed good antioxidant properties in both 30% sunflower oil-in-water (OW) and 20% water-in-sunflower oil emulsions (WO), pH 5.4, during storage at 50 ºC. Although bovine serum albumin (BSA) (0.2%) had a slight antioxidant effect, the combination of caffeic acid and BSA showed a synergistic reduction in the rate of development of rancidity, with significant reductions in concentration of total volatiles, peroxide value (PV) and p-anisidine value (PA) for both emulsion types. The synergistic increase in stability of the OW and WO emulsions containing BSA and caffeic acid was 102.9 and 50.4 % respectively based on TOTOX values, which are calculated as 2PV + PA, with greater synergy calculated if based on formation of headspace volatiles, The OW emulsion was more susceptible to the development of headspace volatiles by oxidation than the WO emulsion, even though the degree of oxidation assessed by the TOTOX value was similar.
• Aidos, I.; Jacobsen, C., Jensen, B., Luten, J. B., Van der Padt, A., & Boom, R. M. (2002). Volatile oxidation products formed in crude herring oil under accelerated oxidative conditions. Eur. Food Res. Technol., 104, 808–818. • Almajano, M. P., Carbo, R., Delgado, M. E., & Gordon, M. H. (2007). Effect of pH on the antimicrobial activity and oxidative stability of oil-in-water emulsions containing caffeic acid. J. Food Sci., 72, 258-263. • Almajano, M. P., & Gordon, M. H. (2004). Synergistic effect of BSA on antioxidant activities in model food emulsions. J. Am. Oil Chem. Soc., 81, 275-280. • AOCS Official Method cd 18-90. (1989). In Official methods and recommended practices of the American Oil Chemists’ Society, 4th Ed., Firestone, D. Ed., American Oil Chemists’ Society: Champaign, IL. • Arcan, I. & Yemenicioğlu, A. (2007). Antioxidant activity of protein extracts from heat-treated or thermally processed chickpeas and white beans. Food Chem., 103, 301–312. • Bartolomé, B., Estrella, I., & Hernández, M. T. (2000). Interaction of low molecular weight phenolics with proteins (BSA). J. Food Sci., 65, 617-621. • Chen, J. H., & Ho, C. T. (1997). Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem., 45, 2374–2378. • Decker, E. A., Warner, K., Richards, M. P., & Shahidi, F. (2005). Measuring antioxidant effectiveness in food. J. Agric. Food Chem. 53, 4303–4310. • De Leonardis A., & Macciola V. (2003). Effectiveness of caffeic acid as an anti-oxidant for cod liver oil. Int. J. Food Sci. Technol., 38, 475–480. • Díaz, M., Dunn, C., McClements, D. J., & Decker, E. A. (2003). Use of caseinophosphopeptides as natural antioxidants in oil-in-water emulsions. J. Agric. Food Chem., 51, 2365-2370. • Frankel, E. N. (1998). Lipid Oxidation. The Oily Press Ltd.: West Ferry, Dundee, Scotland. • Frankel, E. N., Huang, S.-W., Kanner, J., & German, J. B. (1994). Interfacial phenomena in the evaluation of antioxidants: bulk oils vs emulsions. J. Agric. Food Chem., 42, 1054-1059. • Gülçin, I. (2006). Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicol., 217, 213–220. • Halliwell, B., Murcia, M. A., Chirico, S., & Aruoma, O. I. (1995). Free radicals and antioxidants in food and in vivo: what they do and how they work. Crit. Rev. Food Sci. Nutr. 35, 7-20. • He, T., Liang, Q., Wang, Y., & Luo, G. (2010). Characterization of the interactions between natural flavonoid compounds and bovine serum albumin by capillary electrophoresis and fluorescence method. J. Liq. Chromatogr. Rel. Technol., 33, 548-562. • Huang, S.-W., Hopia A., Schwarz K., Frankel E. N., & German J. B. (1996). Antioxidant activity of a tocopherol and trolox in different lipid substrates: bulk oils vs oil-in-water emulsions. J. Agric. Food Chem., 44, 444-452. • Jacobsen, C., Let, M. B., Nielsen, N. S., & Meyer, A. S. (2008). Antioxidant strategies for preventing oxidative flavour deterioration of foods enriched with n-3 polyunsaturated lipids: a comparative evaluation. Trends in Food Sci. & Technol., 19, 76-93 • Jiménez-Álvarez, D., Giuffrida, F., Golay, P. A., Cotting, C., Destaillats, F., Dionisi, F., et al.; (2008). Profiles of volatile compounds in milk containing fish oil analyzed by HS-SPMEGC/ MS. Eur. J. Lipid Sci. Technol., 110, 277–283. • Lee, S.H., Suh, J.K., & Li, M. (2003). Determination of bovine serum albumin by its enhancement effect of nile blue fluorescence. B. Kor. Chem.Soc., 24 (1), 45-48. • Leonardis, A. D., & Macciola, V. (2003). Effectiveness of caffeic acid as an antioxidant for cod liver oil. Int. J. Food Sci. Technol., 38, 475–480. • List, G. R., Evans, C. D., Kwolek, W. F., Warner, K., Boundy, B. K., & Cowan, J. C. (1974). Oxidation and quality of soybean oil: A preliminary study of the anisidine test. J. Am. Oil Chem. Soc., 51, 17–21. • Mancuso, J. R., McClements, D. J., & Decker, E. A. (1999). The effects of surfactant type, pH, and chelators on the oxidation of salmon oil-in- water emulsions. J. Agric. Food Chem. 47, 4112–4116. • Maqsood, S., & Benjakul, S. (2010). Comparative studies of four different phenolic compounds on in vitro antioxidative activity and the preventive effect on lipid oxidation of fish oil emulsion and fish mince. Food Chem., 119, 123-132. • McClements, D. J., & Decker, E. A. (2000). Lipid oxidation in oil-in-water emulsions: impact of molecular environment on chemical reactions in heterogeneous food systems. J. Food Sci. 65, 1270-1282. • Oda Y. M., Kinoshita, K., Nakayama, K., & Kakehi, K. (1998). Evaluation of fluorescence polarization method for binding study in carbohydrate–lectin interaction. Bio. Pharm. Bulletin., 21, 1215–1217. • Porter, W. L. (1993). Paradoxical behavior of antioxidants in food and biological systems. Toxicol. Ind. Health., 9, 93-122. • Prigent, S. V. E., Voragen, A. G. J., Visser, A. J. W. G., Van Koningsveld, G. A., & Gruppen, H. (2007). Covalent interactions between proteins and oxidation products of caffeoylquinic acid (chlorogenic acid). J. Sci. Food Agric., 87, 2502-2510. • Rampon, V., Lethuaut, L., Mouhous-Riou, N., & Genot, C. (2001). Interface characterization and aging of bovine serum albumin stabilized oil-in-water emulsions as revealed by front-surface fluorescence, J. Agric. Food Chem., 49, 4046–4051. • Rawel, H.M., Rohn, S., Kruse, H.P., & Kroll, J. (2002). Structural changes induced in bovine serum albumin by covalent attachment of chlorogenic acid. Food Chem., 78 (4), 443-445. • Rouseff, R. L., & Cadwallader, K. R. (2001). Headspace volatile aldehydes as indicators of lipid oxidation in food. In Headspace techniques in foods and flavours; Kluwer Academic/Plenum Publishers: New York. • Selke, E., Rohwedder, W. K., & Dutton, H. J. (1980). Volatile components from trilinolein heated in air, J. Am. Oil Chem. Soc., 57, 25-30. • Shehata, A. J., de Man. J. M., & Alexander, J. C. (1970). A simple and rapid method for the preparation of methyl esters of fats in milligram amounts for gas chromatography. Can. Inst. Food Sci. Technol. J., 3, 85-89. • SØrensen, A. M., Haahr, A., Becker, E. M., Skibsted, L. H., Bergenståhl, B., Nilsson, L.et al. (2008). Interactions between iron, phenolic compounds, emulsifiers, and pH in omega-3-enriched oil-in-water emulsions. J. Agric. Food Chem. 56, 1740-1750. • Wang, W.Q., & Goodman, M. T. (1999). Antioxidant property of dietary phenolic agents in a human LDL oxidation ex vivo model: Interaction of protein binding activity, Nutr. Res., 19, 191–202. • Yanishlieva, N., & Marinova, E. M. (1995). Effects of antioxidants on the stability of triacylglycerols and methyl esters of fatty acids of sunflower oil. Food Chem., 54, 377–382. • Yoshida, H. (1993). Influence of fatty acids of different unsaturation in the oxidation of purified vegetable-oils during microwave irradiation. J. Sci. Food Agric., 62, 41–47.