Natural phenolic antioxidants to protect flaxseed oil from oxidation
Abstract
The aim of this work was to identify effective natural antioxidants (AO) for stabilizing flaxseed oil (FO), which is characterized by a high content of α-linolenic acid (omega-3 fatty acid). Under conditions of accelerated oxidation at 100 °C, the values of the induction period and the efficiency of FO oxidation inhibition (stabilization factor F) were determined in the presence of additives of 0.02 wt. % of 26 natural phenolic compounds, as well as some known synthetic AO for comparison. The most effective AO were identified: gallic and caffeic acids, fraxetin, gossypol (F = 1.97–2.58). The AO activity of fraxetine, gallic and caffeic acids does not statistically significantly differ from the synthetic AO propyl gallate and ascorbyl palmitate and significantly exceeds the AO activity of butylated hydroxytoluene.The second group of natural AO, including sinapic acid, esculetin, and quercetin, showed lower efficiency in FO (F = 1.40–1.52). Other hydroxylated derivatives of benzoic and cinnamic acids, as well as coumarin, dicoumarol, curcumin and resveratrol showed low or no AO activity in FO. It was shown that the use of compositions of ascorbyl palmitate and natural phenolic AO, such as gallic acid, caffeic acid and fraxetine, allows to effectively inhibit FO oxidation, significantly increasing the stabilization factor (up to 3.77–4.18).
About the Authors
A. A. Sosnovskaya
Research Institute for Physical Chemical Problems, Belarusian State University
Belarus
Belarus
Sosnovskaya Anna Alekseevna, Ph.D (Chemistry), leading researcher of laboratory of chemistry of free radical processes
31, Korzhenevsky St., арt. 335. 220108, Minsk
I. P. Edimecheva
Research Institute for Physical Chemical Problems, Belarusian State University
Belarus
Belarus
Edimecheva Irina Petrovna, Ph.D (Chemistry), leading researcher of laboratory of chemistry of free radical processes
27, K. Marx St., арt. 7, 220030, Minsk
G. A. Ksendzova
Research Institute for Physical Chemical Problems, Belarusian State University
Belarus
Belarus
Ksendzova Galina Anatolievna, Ph.D (Chemistry), the head of the sector of chemistry of free radical processes of laboratory of chemistry of free radical processes
11, Dachnaja str., 223034, Zaslavl
References
1. Al-Madhagy, S. A comprehensive review of the health benefits of flaxseed oil in relation to its chemical composition and comparison with other omega-3-rich oils / S. Al-Madhagy, N. S. Ashmawy, A. Mamdouh [et al.] // Eur. J. Med. Res. — 2023. — V. 28. — 240. URL: https://doi.org/10.1186/s40001-023-01203-6.
2. Choe, E. Mechanisms and factors for edible oil oxidation / E. Choe, D. B. Vin // Compr. Rev. Food Sci. F. — 2006. — V. 5. P. 169–186. URL: https://doi.org/10.1111/j.1541-4337.2006.00009.x.
3. Frankel, E. N. Antioxidants in lipid foods and their impact on food quality / E. N. Frankel // Food Chem. — 1996. — V. 57. — P. 51–55. URL: https://doi.org/10.1016/0308-8146(96)00067-2.
4. Liu, R. Synthetic Phenolic Antioxidants: A Review of Environmental Occurrence, Fate, Human Exposure, and Toxicity / R. Liu, S. A. Mabury // Environ. Sci. Technol.– 2020.– V. 54.– P. 11706–11719. https://doi.org/10.1021/acs.est.0c05077.
5. Wu, L. Food additives: From functions to analytical methods / L. Wu, C. Zhang, Y. Long [at al.] // Crit. Rev. Food Sci. Nutr. — 2022. — V. 62(30). — P. 8497-8517. URL: https://doi.org/10.1080/10408398.2021.192982.
6. Yanishlieva, N. V. Stabilization of edible oils with natural antioxidants / N. V. Yanishlieva, E. M. Marinova // Eur. J. Lipid Sci. Technol. — 2001 — V. 103(11). — P. 752–767. URL: https://doi.org/10.1002/1438-9312(200111)103:11<752::AID-EJLT752>3.0.CO;2-0.
7. Viana da Silva, M. Synthetic and Natural Antioxidants Used in the Oxidative Stability of Edible Oils: An Overview / M. Viana da Silva, M. R. C. Santos, I. R. Alves Silva [at al.] // Food Rev. Intern. — 2021. — V. 38(sup. 1). — P. 1–24. URL: https://doi.org/10.1080/87559129.2020.1869775.
8. Li, A-N. Resources and Biological Activities of Natural Polyphenols / A-N. Li, S. Li, Y-J. Zhang [at al.] // Nutrients. — 2014. — V. 6(12). — P. 6020–6047. URL: https://doi.org/10.3390/nu6126020.
9. Rice-Evans, C. A. Structure-antioxidant activity relationships of flavonoids and phenolic acids / C. A. Rice-Evans, N. J. Miller, G. Paganga // Free Radic. Biol. Med. — 1996. — V. 20(7). — P. 933–956. URL: https://doi.org/10.1016/0891-5849(95)02227-9.
10. Kumar, N. Phenolic acids: Natural versatile molecules with promising therapeutic applications / N. Kumar, N. Goel // Biotechnol. Rep. (Amst). — 2019. — V. 24. — e00370. URL: https://doi.org/10.1016/j.btre.2019.e00370.
11. Kiokias, S. Phenolic Acids of Plant Origin — Review on Their Antioxidant Activity In Vitro (O/W Emulsion Systems) Along with Their in Vivo Health Biochemical Properties / S. Kiokias, C. Proestos, V. Oreopoulou // Foods. — 2020. — V. 9(4). — 534. URL: https://doi.org/10.3390/foods9040534.
12. Coumarins: Biology, Applications, and Mode of Action / eds. R. O’Kennedy, R.D. Thornes. — New York, U.S: John Wiley & Sons, 1997. — Р. 360.
13. Kadakol, A. Esculetin: A phytochemical endeavor fortifying effect against non-communicable diseases / A. Kadakol, N. Sharma, Y. A. Kulkarni, A. B. Gaikwad // Biomed. Pharmacother. — 2016. — V. 84. — P. 1442–1448. URL: https://doi.org/10.1016/j.biopha.2016.10.072.
14. Yanishlieva, N. V. Antioxidative effectiveness of some natural antioxidants in sunflower oil / N. V. Yanishlieva, E. M. Marinova // Z. Lebensm. Unters. Forsch. — 1996. — V. 203(3). — P. 220–223. URL: https://doi.org/10.1007/bf01192867.
15. Omar, K. I. Stabilizing flaxseed oil with individual antioxidants and their mixtures / K. I. Omar, L. Shan, Y. L.Wang, X. Wang // Eur. J. Lipid Sci. Technol. — 2010. — V. 112(9). — P. 1003–1011. URL: https://doi.org/10.1002/ejlt.200900264.
16. Michotte, D. Linseed oil stabilisation with pure natural phenolic compounds / D. Michotte, H. Rogez, R. Chirinos, E. Mignolet // Food Chem. — 2011. — V. 129. — P. 1228–1231. URL: https://doi.org/10.1016/j.foodchem.2011.05.108.
17. Shadyro, O. I. Flaxseed oil stabilization using natural and synthetic antioxidants / O.I. Shadyro, A. A. Sosnovskaya, I. P. Edimecheva // Eur. J. Lipid Sci. Technol. — 2017. — V. 119, 1700079. URL: https://doi.org/ejlt.201700079.
18. Колар, М.Х. Натуральный антиоксидант — экстракт розмарина / М. Х. Колар, С. Урбанчич // Масла и жиры. — 2008. — Т. 3. — С. 26–28.
19. Nag, A. Stabilization of flaxseed oil with capsicum antioxidant / A. Nag // J. Am. Oil Chem. Soc. — 2000. — V. 77. P. 799–800. URL: https://doi.org/10.1007/s11746-000-0127-0.
20. Шадыро, О. И. Применение растительного сырья для защиты льняного масла от окисления / О. И. Шадыро, А. А. Сосновская, И. П. Едимечева // Вес. Нац. акад. навук Беларусi. Cер. аграр. навук. — № 1. — С. 121–126.
21. Abad, A. A robust stripping method for the removal of minor components from edible oils / A. Abad, F. Shahidi // Food Prod. Process. and Nutr. — 2020. — V. 2(1), P. 2–9. URL: https://doi.org/10.1186/s43014-019-0015-2.
22. ГОСТ Р 53160–2008 (ИСО 6886: 2006). Жиры и масла животные и растительные. Определение устойчивости к окислению (ускоренное испытание на окисление). — Введ. 01.01.2010. — М.: Стандартинформ, 2009. — 16 с.
23. СТБ ГОСТ Р 51487–2001. Масла растительные и жиры животные. Метод определения перекисного числа. — Введ. 01.11.2002. — Минск: БелГИСС, 2001. — 6 с.
24. ГОСТ 31933–2012. Масла растительные. Методы определения кислотного числа и кислотности (с Изменением N 1). — Введ. 01.01.2014. — М.: Стандартинформ, 2014. — 11 с.
25. СТБ 1869–2008 (ИСO 6885:2006). Жиры и масла животные и растительные Определение анизидинового числа. — Введ. 01.01.2009. — Минск: БелГИСС, 2008. — 15 с.
26. ГОСТ 5475-69 (ISO 3691:2013). Масла растительные. Методы определения йодного числа (с Изменениями N 1, 2). — Введ. 01.01.1970. — М.: ИПК Издательство стандартов, 2001. — 19-23 с.
27. CТБ ИСО 5509-2007. Жиры и масла животные и растительные. Приготовление метиловых эфиров жирных кислот. — Введ. 01.10.2007. — Минск: БелГИСС, 2007 — 20 с.
28. Herchi, W. Characterisation of the glycerophospholipid fraction in flaxseed oil using liquid chromatographymass spectrometry / W. Herchi, F. Sakouhi, S.Khaled [at al.] // Food Chem.– 2011. — V. 129. — P. 437–442. URL: https://doi.org/10.1016/j.foodchem.2011.04.096.
29. Chen, J. Structure-antioxidant activity relationship of methoxy, phenolic hydroxyl, and carboxylic acid groups of phenolic acids / J. Chen, J. Yang, L. Ma [at al.] // Sci. Rep. –2020. — V. 10(1). — 2611. URL: https://doi.org/10.1038/s41598-020-59451-z.
30. Pokorny, J. Antioxidant in food preservation. / J. Pokorny // Handbook of food preservation / eds. M. S. Rahman, M. Dekker. — New York (USA): CRC Press, 1999. — P. 309–337.
31. Kamal-Eldin, A. The chemistry and antioxidant properties of tocopherols and tocotrienols / A. Kamal-Eldin, L-A. Appelqvist // Lipids. — 1996. — V. 31. — P. 671–701. URL: https://doi.org/10.1007/BF02522884.
32. Quinn, P. J. Expansion of antioxidant function of vitamin E by coenzyme Q / P. J. Quinn, J. P. Fabisiak, V. E. Kagan // Biofactors. — 1999. — V. 9. — P. 149–154. URL: https://doi.org/10.1002/biof.5520090209.
33. Bandarra, N. M. Antioxidant synergy of α-tocopherol and phospholipids / N. M. Bandarra, R. M. Campos, I. Batista, M. L. Nunes, J. M. Empis // J. Am. Oil Chem.’ Soc. — 1999. — V. 76. — P. 905–913. URL: https://doi.org/10.1007/s11746-999-0105-4.
34. Moser, B. R. Efficacy of gossypol as an antioxidant additive in biodiesel / B. R. Moser // Renew. Energy. — 2012. — V. 40(1). — P. 65–70. URL: https://doi.org/10.1016/j.renene.2011.09.022.
35. Sakanashi, Y. Possible use of quercetin, an antioxidant, for protection of cells suffering from overload of intracellular Ca2+: a model experiment / Y. Sakanashi, K. Oyama, H. Matsui [et al.] // Life Sci. — 2008. – V. 83. — P. 164–169. URL: https://doi.org/10.1016/j.lfs.2008.05.009.
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Sosnovskaya A.A., Edimecheva I.P., Ksendzova G.A. Natural phenolic antioxidants to protect flaxseed oil from oxidation. Food Industry: Science and Technology. 2025;18(3):75-87. (In Russ.)
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