Evaluation of effeciancy of luteolin on stability of olive and canola oils in different temperatures according to the mechanism of inhibitory action

Authors
1 1Ph.D student of department of Food Science and Technology, Faculty of Agriculture, Ferdowsi University of Mashhad, P.O. Box 91775-1163, Mashhad, Iran, E-mail: sma_257@yahoo.com.
2 full Professor, Department of Food Science and Technology, Faculty of Agriculture, Ferdowsi University of Mashhad
Abstract
A kinetic analysis was performed to evaluate the antioxidant behaviour of luteolin in the triacylglycerols of olive (TGO) and canola (TGC) oils. The process was performed at high (kinetic regime) oxygen concentrations at at 60, 80, and 100 °C in the dark. Different kinetic parameters were determined, including the stabilization factor F, the oxidation rate ratio ORR, the antioxidant activity (A) and the mean rate of inhibitor consumption WInH. The oxidative stability measures of the bulk olive and canola oils dramatically improved by the antioxidant added. Luteolin due to its increased partitioning at water-oil interface exerted a highest activity at 60°C and a concentration of 0.02%. Also, the rate of olive triacylglycerols oxidation increased significantly with increasing luteolin concentration at the corresponding temperature. This behaviour was explained in terms of a more participation of antioxidant molecules and radicals in side reactions, i.e. 10 and 11 ( and , respectively). The rate constant of antioxidant consumption in side reaction(s) (Keff) and mean rate of initiation (Wi/f) values revealed that luteolin takes part in chain propagation and initiation reactions to a higher extent during TGC oxidation. Generally, the activity of luteolin increased and decreased, respectively, in TGO and TGC with rising temperature. This behavior was attributed to the change in the mechanism of inhibitory action with prevailing the reactions 7 ( , 8 ( ), and 9 ( ) for olive oil, and pro-oxidative side reactions to a higher degree in TGC.
Keywords

Subjects


1. Chaiyasit, W., Elias, R.J., McClements, D.J., and Decker, A. (2007). Role of physical structures in bulk oils on lipid oxidation. Critical Reviews in Food Science and Nutrition, 47, 299–317.
2. Farhoosh, R. (2005). Antioxidant activity and mechanism of action of butein in linoleic acid. Food Chemistry, 93, 633–639.
3. Amic, D., Davidovic-Ami, D., Beslo, D., Rastija, V., Lucic, B., and Trinajstic, N. (2007). SAR and QSAR of the antioxidant activity of flavonoids, Current Medicinal Chemistry, 14, 827-845.
4. Leopoldini, M., Pitarch, I. P., Russo, N., and Toscano, M. (2004b). Structure, conformation and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study. The Journal of Physical Chemistry A., 108, 92–96.
5. Brighente, I.M.C., Dias, M., Verdi, L.G., and Pizzolatti, M.G. (2007). Antioxidant activity and total phenolic content of some brazilian species. Pharmaceutical Biology, 45, 156–161.
6. Ruzic, I., Kerget, M., and Knez, Z. (2010). Potential of phenolic antioxidants. Acta Chimica Slovenia, 57, 263–271.
7. Kulisica, T., Radonicb, A., Katalinicc, V., and Milosa, M. (2004). Use of different methods for testing antioxidative activity of oregano essential oil. Food Chemistry, 85, 633–640.
8. Yang, J., Sung Kim, J., Jeong H.J., Kang, H., Cho J., Yeom, H., and Kim, M.J. 2011. Determination of antioxidant and α-glucosidase inhibitory activities and luteolin contents of Chrysanthemum morifolium Ramat extracts. African Journal of Biotechnology, 10, 19197–19202.
9. Lopez-Lazaro, M. (2009). Distribution and biological activities of the flavonoid luteolin. Mini-views in Medicinal Chemistry, 9, 31–59.
10. Maestri, D.M., Nepote, V., Lamarque, A.L., and Zygadlo, J.A. (2006). Natural products as antioxidant phytochemistry. Phytochemistry: Advances in Research, 37(2), 105–135.
11. Ai-Li, J., and Chang-Hai, W. 2006. Antioxidant properties of natural components from Salvia plebeia on oxidative stability of ascidian oil. Process Biochemistry, 41, 1111–1116.
12. Yang, J. G., Liu, B. G., Liang, G. Z., and Ning, Z. X. (2009). Structure activity relationship of flavonoids active against Lard oil oxidation based on quantum chemical analysis. Molecules, 14, 46-52.
13. Chaiyasit, W., McClements, D.J., and Decker, E.A. (2005). The relationship between the physicochemical properties of antioxidants and their ability to inhibit lipid oxidation in bulk oil and oil-in-water emulsions. Journal of Agricultural and Food Chemistry, 53(12), 4982-8.
14. Yanishlieva, N.V., Marinova, E.M., Gordonb, M.H., and Raneva, G.V. 1999. Antioxidant activity and mechanism of action of thymol and carvacrol in two lipid systems. Food Chemistry, 64, 59–66.
15. Cuvelier, M. E., Bondet, V., and Berset, C. (2000). Behavior of Phenolic Antioxidants in a Partitioned Medium: Structure–Activity Relationship. Journal of the American Oil Chemists' Society, 77( 8), 819-823.
16. Yanishlieva, N.V., and Marinova, E.M. (1995). Effects of antioxidants on the stability of triacylglycerols and methyl esters of fatty acids of sunflower oil. Food Chemistry, 54, 371–382.
17. Asnaashari, M., Farhoosh, R., and Sharif, A. 2014. Antioxidant activity of gallic acid and methyl gallate in triacylglycerols of Kilka fish oil and its oil-in-water emulsion. Food Chemistry, 159, 439–444.
18. Yanishlieva, N.V., & Marinova, E.M. (2003). Kinetic evaluation of the antioxidant activity in lipid oxidation. In A. Kamal-Eldin (Ed.), Lipid Oxidation Pathways (pp. 85–110). AOCS Press: Champaign.
19. Soobrattee, M. A., Neergheen, V. S., Luximon-Rammaa, A., Aruomab, O.I., and., Bahorun, T. (2005). Phenolics as potential antioxidant therapeutic agents: Mechanism and actions. Mutation Research, 56, 200–213.
20. Bassani, D. C., Nunes, D. S., and Granato, D. (2014). Optimization of phenolics and flavonoids extraction conditions and antioxidant activity of roasted yerba-mate leaves (Ilex paraguariensis St.-Hil., Aquifoliaceae) using response surface methodology. Annals of the Brazilian Academy of Sciences, 86(2), 923–933.
21. Budilarto, E. S., & Kamal-Eldin, A. (2015). The Supramolecular Chemistry of Lipid Oxidation and Antioxidation in Bulk Oils (accepted article). European Journal of Lipid Science and Technology. 1-74.
22. Laguerre, M., Bayrasy, C., Panya , A., Weiss, J., McClements, J., Lecomte, J., Decker, E. A., and Villeneuve, P. (2013). What makes good antioxidants in lipid-based systems? The next theories beyond the polar paradox. Critical Reviews in Food Science and Nutrition, 55(2), 183-201.
23. Ghnimi, S., Budilarto, E., and Kamal-Eldin, A. (2017). The new paradigm for lipid oxidation and insights to microencapsulation of omega-3 fatty acids. Comprehensive Reviews in Food Science and Food Safety, 16, 1206–1218.
24. Mahdavianmehr, H., Farhoosh, R., and Sharif, A. (2016). Mechanism of the Inhibitory Effect of Hydroxytyrosol on Lipid Oxidation in Different Bulk Oil Systems, Journal of the American Oil Chemists' Society, 93(9), 1233-1242.
25. Kamal-Eldin, A. (2003). Lipid oxidation pathways. AOCS Press: USA.