بررسی پایداری حرارتی تری‌آسیل‌گلیسرول‌های آفتابگردان و زیتون تحت تأثیر اسید‌گالیک و متیل‌گالات

مجله پژوهشهای علوم و صنایع غذایی ایران

مقاله 3، دوره 20، شماره 2 - شماره پیاپی 86، خرداد و تیر 1403، صفحه 217-227   

نوع مقاله: مقاله پژوهشی فارسی

شناسه دیجیتال (DOI): 10.22067/ifstrj.2023.80273.1228

نویسندگان

مژگان اکبری؛ رضا فرهوش^* ؛ مرضیه معین فرد

گروه علوم و مهندسی صنایع غذائی، دانشکده کشاورزی، دانشگاه فردوسی مشهد، مشهد، ایران

چکیده

در پژوهش حاضر، تجزیه‌وتحلیل سینتیکی رفتار آنتی­ اکسیدانی اسیدگالیک، متیل­ گالات و TBHQ در تری ­آسیل­ گلیسرول‌های روغن‌زیتون و آفتابگردان انجام شد. فرایند اکسایش روغن‌ها در رژیم سینتیکی (غلظت بالای اکسیژن) در دمای ٨٠ درجه سانتی‌گراد و در یک سطح غلظتی (2/1 میکرو مول بر گرم) در محیط تاریک صورت گرفت. پارامترهای سینتیکی مختلف شامل فاکتور پایدارسازی (F) که نمایانگر میزان کارآمدی، نسبت سرعت اکسایش (ORR) که نمایانگر قدرت، فعالیت آنتی­ اکسیدانی (A) که ترکیب فاکتور پایداری و قدرت موردبررسی قرار گرفت. پایداری اکسایشی تری­ آسیل­گلیسرول‌ها به‌صورت معنی‌داری در حضور آنتی‌اکسیدان‌های افزوده‌شده در سطح غلظتی و دمایی، نسبت به نمونه کنترل بهبود یافت. در دمای 80 و هر دو نوع تری­ آسیل­ گلیسرید مورداستفاده، قدرت آنتی­ اکسیدانی TBHQ به‌طور معنی­ داری از اسید­گالیک و متیل ­گالات بیشتر بود. در روغن آفتابگردان، متیل­ گالات قدرت آنتی­ اکسیدانی بیشتری نسبت به اسید­گالیک نشان داد و نتایج به‌دست‌آمده با خاصیت حملی بالاتر اسید­گالیک مطابقت نداشت، درحالی‌که در روغن‌زیتون، اسید­گالیک قدرت آنتی­ اکسیدانی بیشتری نشان داد. زمان لازم برای رسیدن به حد بحرانی عدد کربونیل، برای هر دو نوع تری­ آسیل ­گلیسرول و تمام تیمارها به‌صورت معنی­ دار نسبت به تیمار کنترل، در دمای 80 درجه سانتی‌گراد، بهبود نشان داد و بین دو تیمار اسید­گالیک و متیل ­گالات، متیل­ گالات مؤثرتر بود.

کلیدواژه‌ها

پایداری حرارتی؛ سینتیک؛ عددهای اکسیداسیون

مراجع

1. Asnaashari, M., Farhoosh, R., & 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. https://doi.org/10.1016/j.foodchem.2014.03.038
2. Baccouri, O., Guerfel, M., Baccouri, B., Cerretani, L., Bendini, A., Lercker, G., Zarrouk, M., & Daoud Ben Miled, D. (2008). Chemical composition and oxidative stability of Tunisian monovarietal virgin olive oils with regard to fruit ripening. Food Chemistry, 109, 743-754. https://doi.org/10.1016/j.foodchem.2008.01.034
3. Becker, E.M., Nissen, L.R., & Skibsted, L.H. (2004). Antioxidant evaluation protocols: food quality or health effects. European Food Research and Technology, 219, 561-571. https://doi.org/10.1007/s00217-004-1012-4
4. Bendary, E., Francis, R.R., Ali, H.M.G., Sarwat, M.I., & Hady, S.EI. (2013). Antioxidant and structure-activity relationships (SARs) of some phenolic and anilines compounds. Annals of Agricultural Science, 58, 173-181. https://doi.org/10.1016/j.aoas.2013.07.002
5. Borde, V., UPangrikar, P.P., & Tekale, S.U. (2011). Gallic acid in ayurvedic herbs and formulations. Recent Research in Science and Technology, 3(7), 51-54.
6. 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. https://doi.org/10.1002/ejlt.201400200
7. Cao, G., Sofic, E., & Prior, R.L. (1997). Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships, 22(5), 749-760. https://doi.org/10.1016/s0891-5849(96)00351-6
8. Chaiyasit, W., McClements, D.J., & 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. https://doi.org/10.1021/jf0501239
9. Choe, E., & Min, D.B. (2009). Mechanisms of antioxidants in the oxidation of foods. Comprehensive Reviews in Food Science and Food Safety, 8, 345-358. https://doi.org/10.1111/j.1541-4337.2009.00085
10. Cuvelier, M.E., Richard, H., & Berset, C. (1992) .Comparison of the antioxidative activity of some acid-phenols: structureactivity relationship. Bioscience, Biotechnology, and Biochemistry, 56(2), 324-325. https://doi.org/10.1271/bbb.56.324
11. Denisove, E., & Khudyakov, I. (1987). Mechanism of action and reactivities of the free radicals of inhibitors. Chemical Reviews, 87, 1313-1357. https://doi.org/10.1021/cr00082a003
12. Endo, Y., Li, C.M., Tagiri-Endo, M., & Fugimoto, K. (2001). A modified method for the estimation of total carbonyl compounds in heated and frying oils using 2-propanol as a solvent. Journal of the American Oil Chemists’ Society, 10, 1021-1024. https://doi.org/10.1007/s11746-001-0381-1
13. Farhoosh, R. (2005). Antioxidant activity and mechanism of action of butein in linoleic acid. Food Chemistry, 93, 633-639. https://doi.org/10.1016/j.foodchem.2004.10.041
14. Farhoosh, R. (2007). The effect of operational parameters of the Rancimat method on the determination of the oxidative stability measures and shelf life of soybean oil. Journal of the American Oil Chemists’ Society, 84, 205-209. https://doi.org/10.1007/s11746-006-1030-4
15. Farhoosh, R., Niazmand, R., Rezaei, M., & Sarabi, M. (2008). Kinetic parameter determination of vegetable oil oxidation under rancimat test conditions. European Journal of Lipid Science and Technology, 110, 587-592. https://doi.org/10.1002/ejlt.200800004
16. Farhoosh, R., & Tavasoli Kafrani, M.H. (2011) Simutaneous monitoring of conventional qualitative indicators during frying of sunflower oil. Food Chemistry, 125, 209-213. https://doi.org/10.1016/j.foodchem.2010.08.064
17. Farhoosh, R., & Hoseini-Yazdi, S.Z. (2013). Shelf-life prediction of olive oils using empirical models developed at low and high temperatures. Food Chemistry, 141, 557-565. https://doi.org/10.1016/j.foodchem.2013.03.024
18. Farhoosh, R., & Hoseini-Yazdi, S.Z. (2014). Evolution of oxidative values during Kinetic studies on olive oil oxidation in the Rancimat test. Journal of the American Oil Chemists' Society, 91(2), 281-293. https://doi.org/10.1007/s11746-013-2368-z
19. Farhoosh, R., Johnny, S., Asnaashari, M., Molaahmadibahraseman, N., & Sharif, A. (2016a). Structure-antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid. Food Chemistry, 194, 128-134. https://doi.org/10.1016/j.foodchem.2015.08.003
20. Farhoosh, R., Sharif, A., Asnaashari, M., Johnny, S., & Molaahmadibahraseman, N. (2016b). Temperature-dependent mechanism of antioxidant activity of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid in fish oil. Journal of the American Oil Chemists' Society, 93, 555-567. https://doi.org/10.1007/s11746-016-2790-0
21. Farhoosh, R, & Nystrom, L.(2018). Antioxidant potency of gallic acid, methyl gallate and their combinations in sunflower oil triacylglycerols at high temperature. Food Chemistry, 244, 29-35. https://doi.org/1016/j.foodchem.2017.10.025
22. Frankel, E.N. (1980). Lipid oxidation. Progress in Lipid Research, 19, 1-22. https://doi.org/10.1016/0163-7827(80)90006-5
23. Frankel, E.N. (2005). Lipid oxidation. The Oily Press LTD. Dundee, Scotland.
24. Frankel, E.N., Huang, S.W., Kanner, J., & German, J.B. (1994). Interfacial phenomena in the evaluation of antioxidants: bulk oils vs. emulsions. Journal of Agricultural and Food Chemistry, 42, 1054-1059. https://doi.org/10.1021/jf00041a001
25. Hsieh, R.J., & Kinsella, J.E. (1980). Oxidation of polyunsaturated fatty acids: mechanisms, products, and inhibition with emphasis on fish. Advances in Food and Nutrition Research, 33, 233-341. https://doi.org/10.1016/S1043-4526(08)60129-1
26. Huang, S.W., Frankel, E.N., Schwarz, K., Aeschbach, R., & German, J.B. (1996). Antioxidant activity of carnosic acid and methyl carnosate in bulk oils and oil-in-water emulsions. Journal of Agricultural and Food Chemistry, 44, 2951-2956. https://doi.org/10.1021/jf960068r
27. Kamal-Eldin, A. (2003). Lipid oxidation pathways. AOCS Press: USA. https://doi.org/10.1201/9781003040316
28. Kikuzaki, H., Hisamoto, M., Hirose, K., Akiyama, K., & Taniguchi, H. (2002). Antioxidant properties of ferulic acid and its related compounds, Journal of Agricultural and Food Chemistry, 50, 2161-2168. https://doi.org/10.1021/jf011348w
29. Kim, S.H, Jun, C.D., Suk, K., Choi, B.J., Lim, H., Park, S., Lee, S.H., Shin, H.Y., Kim, D.K., & Shin, T.Y. (2006). Gallic acid inhibits histamine release and pro-inflammatory cytokine production in mast cells. Toxicol Science, 91, 123-131. https://doi.org/10.1093/toxsci/kfj063
30. Leopoldini, M., Pitarch, I.P., Russo, N., & Toscano, M. (2004a). 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. https://doi.org/10.1021/jp035901j
31. Leopoldini, M., Marino, T., Russo, N., & Toscano, M. (2004b). Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism. The Journal of Physical Chemistry A, 108, 4916-4922. https://doi.org/10.1021/jp037247d
32. Leopoldini, M., Russo, N., & Toscano, M. (2011). The molecular basis of natural polyphenolic antioxidants. Food Chemistry, 125, 288-306. https://doi.org/10.1016/j.foodchem.2010.08.012
33. Marinova, E.M., & Yanishlieva, N.V. (1992). Effect of temperature on the antioxidative action of inhibitors in lipid autoxidation. Journal of the Science of Food and Agriculture, 60, 313-318. https://doi.org/10.1002/JSFA.2740600307
34. Matalgyto, F.S., & Al-Khalifa, A.S. (1998). Effect of microwave oven heating on stability of some oil and fats. Arab Gulf Journal of Scientific Research, 16, 21-40. https://doi.org/10.1080/10942912.2016.1152481
35. Mattia, C.D.D., Sacchetti, G., Mastrocola, D., & Pittia, P. (2009). Effect of phenolic antioxidants on the dispersion state and chemical stability of olive oil O/W emulsions. Food Research International (Ottawa, Ont.), 42(8), 1163-1170. https://doi.org/10.1016/j.foodres.2009.05.017
36. Merkl, R., Hradkova, I., Filip, V., & Smidrkal, J.(2010). Antimicrobial and antioxidant properties of phenolic acids alkylesters. Czech Journal of Food Sciences, 28, 275-279. https://doi.org/10.17221/132/2010-CJFS
37. Mendez, E., Sanhueza, J., Speisky, H., & Valenzuela, A. (1996). Validation of the Rancimat test for the assessment of the relative stability of fish oils. Journal of the American Oil Chemists’ Society, 73, 1033-1037. https://doi.org/10.1007/BF02523412
38. Pekkarinen, S., Heinonen, M., & Hopia, A. (1999). Flavonoids quercetin, myricetin, kaemferol and (+)-catechin as antioxidants in methyl linoleate. Journal of the Science of Food and Agriculture, 79, 499-506. https://doi.org/10.1002/(SICI)1097-0010(19990315)79:4<499::AID-JSFA204>3.0.CO;2-U
39. Pe´rez-Gonza´lez, A., Galano, A., & Alvarez-Idaboy, J.R. (2014). Dihydroxybenzoic acids as free radical scavengers: Mechanisms, kinetics, and trends in activity. New Journal of Chemistry, 38, 2639-2652. https://doi.org/10.1039/C4NJ00071D
40. Pokorny, J. (1987). Major factors affecting the autoxidation of lipids. In H.W.S. Chan (Ed.), Autoxidation of Unsaturated Lipids (pp. 141-205). Academic Press: London.
41. Porter, W.L. (1993). Paradoxical behavior of antioxidants in food and biological systems, in Antioxidants: Chemical, Physiological, Nutritional and Toxicological Aspects (William, G.M., ed.), (pp. 93-122). Princeton Scientific, Princeton. https://doi.org/10.1177/0748233793009001-209
42. Rice-Evans, C.A., Miller, N.J., & Paganga, G. (1996). Structure-antioxidant activity relationship of flavonoids and phenolic acids. Free Radical Biology and Chemistry, 20, 933-956. https://doi.org/10.1016/0891-5849(95)02227-9
43. Shahidi, F., Janitha, P.K., & Wanasundara, P.D. (1992). Phenolic antioxidants. Critical Reviews in Food Science and Nutrition, 32, 67-103. https://doi.org/10.1080/10408399209527581
44. Wanasundara, P.K., & Shahidi, F. (2005). Antioxidants: science, technology, and applications. In: Bailey’s Industrial Oil and Fat Products. John Wiley & Sons, Inc. New Jersey. Pp: 431-489. https://doi.org/10.1002/047167849X.bio002
45. Yanishlieva, N.V., & Marinova, E.M. (1992). Inhibited oxidation of lipids I. Complex estimation and comparison of the antioxidative properties of some natural and synthetic antioxidants. Fats Science Technology, 94, 374-379. https://doi.org/10.1002/lipi.19920941004
46. Yanishlieva, N.V., & 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. https://doi.org/10.1016/0308-8146(95)00061-M
47. Yanishlieva, N.V., Marinova, E.M., Gordon, M.H., & Raneva, V.G. (1999). Antioxidant activity and mechanism of action of thymol and carvacrol in two lipid systems. Food Chemistry, 64, 59-66. https://doi.org/10.1016/S0308-8146(98)00086-7
48. Zhu, Y., Long, Q.Z., Zhou, B., Prenzler, P.D., & Zhong, H.Y. (2013). Antioxidant activity of phenolic compounds in bulk camellia oil and corresponding oil in water (O/W) emulsions. Advance Journal of Food Science and Technology, 5, 1238-1243. https://doi.org/10.19026/ajfst.5.3089