Oxidative stability of echium crude oil during the cold-press extraction process
Main Article Content
Keywords
Echium, oxidation, lipoxygenase, volatile, sensory
Abstract
Crude oil extracted from Echium plantagineum L. is a promising sustainable and economical source of omega-3 fatty acids (n-3 FA) for human consumption. However, it is highly susceptible to oxidation during seed processing and oil storage. The objective of this study was to enhance the oxidative stability of crude echium oil by applying antioxidants or thermal treatment to inactivate potential lipoxygenase activity. Echium seeds were subjected to thermal treatment (100°C for 15 min) to inhibit enzymatic oxidation or mixed with tocopherols (300 ppm, oil-based) to mitigate autoxidation during seed crushing. Our analysis revealed no detectable lipoxygenase activity in echium seeds. Interestingly, both thermal treatment (ECH) and the addition of a tocopherol mixture (TOC) increased hydroperoxide concentrations to 10.37 ± 0.56 mmol and12.69 ± 0.49 mmol, respectively, compared to 7.81 ± 0.18 mmol in the untreated seeds (CONT). Similarly, volatile compound levels rose significantly, reaching a ratio of 1.15 ± 0.04 (ECH) and 2.16 ± 0.33 (TOC), compared to 0.44 ± 0.12 in the CONT. In addition, these treatments also reduced the total tocopherol content, with values of 53.69 ± 0.22 mg/100 g (ECH) and 29.62 ± 0.21 mg/100 g (TOC) compared to 62.47 ± 0.71 mg/100 g in the CONT. These findings suggest that oxidation of crude echium oil is not catalyzed by lipoxygenases and that the tocopherol-based antioxidant strategy used in this study, at the tested dose and protocol, did not improve oxidative stability. Future research should explore alternative approaches, such as CO2 supercritical extraction, to enhance the preservation of crude echium oil.
References
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Mihaylova, D., Gandova, V., Deseva, I., Tschuikowa, S., Schalow, S., & Westphal, G. (2020). Arrhenius equation modeling for the oxidative stability evaluation of Echium oil enriched with a natural preservative. European Journal of Lipid Science and Technology, 122(10),
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Matoba T., Hidaka H., Narita H., Kitamura K., Kaizuma N., and Kito M. 1985. Lipoxygenase-2 Isozyme is responsible for generation of n-hexanal in soybean homogenate. J. Agric. Food Chem. 33: 852–855. 10.1021/jf00065a021
Minhas A.M.K., Jain V., Li M., Ariss R.W., Fudim M., Michos E.D., et al. 2023 Family income and cardiovascular disease risk in American adults. Sci. Rep. 13:1–10. 10.1038/s41598-023-27474-x.
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Baysal T., and Demirdöven A. 2007. Lipoxygenase in fruits and vegetables: A review. EMT. 40(4): 491–496. 10.1016/j.enzmictec.2006.11.025
Ben-Aziz A., Grossman S., Ascarelli I., and Budowski P. 1970. Linoleate oxidation induced by lipoxygenase and heme proteins: A direct spectrophotometric assay. Anal. Biochem. 34:88–100.
Botelho P.B., Guimarães J.P., Mariano K.R., Afonso M.S., Koike M. K., Lottenberg A.M.P., et al. 2015. Effect of Echium oil combined with phytosterols on biomarkers of atherosclerosis in LDLr-knockout mice: Echium oil is a potential alternative to marine oils for use in functional foods. Eur. J. Lipid Sci. Technol. 117(10):1561–1568.
Botelho P.B., Mariano K.R., Rogero M.M., and de Castro I.A. 2013. Effect of Echium oil compared with marine oils on lipid profile and inhibition of hepatic steatosis in LDLr knockout mice. Lipids Health and Dis. 12:38. 10.1186/1476-511X-12-38
Burri L., Hoem N., Banni S., Berge K. 2012. Marine omega-3 phospholipids: Metabolism and biological activities. Int. J. Mol. Sci. 13:15401–15419. 10.3390/ijms131115401
Carlini G.C.G., Roschel G.G., Ferrari R.A., Alencar S.M., Ota H.C., da Silveira T.F.F., et al. 2021. Chemical characterization of Echium plantagineum seed oil obtained by three methods of extraction. J. Food Sci. 86(12):5307–5317. 10.1111/1750-3841.15972
Chen B., McClements J.D., and Decker E.A. 2011. Minor components in food oils: A critical review of their roles on lipid oxidation chemistry in bulk oils and emulsions. Crit. Rev. Food Sci. Nutr. 51(10):901–916. 10.1080/10408398.2011.606379
Chong W.K., Mah S.Y., Easa A.M., Tan T.C. 2019. Thermal inactivation of lipoxygenase in soya bean using superheated steam to produce low beany flavour soya milk. JFST. 56(9):4371–4379. 10.1007/s13197-019-03905-4
Comunian, T.A., Favaro L.F., Thomazini M., Pallone E.M.J.A., do Amaral Sobral P.J., de Castro I.A., et al. 2019. Echium oil with oxidative stability increased by emulsion preparation in the presence of the phenolic compound sinapic acid followed by dehydration by spray and freeze drying processes. JFST, 56(3):1155–1164. 10.1007/s13197-019-03576-1
Comunian T.A., Nogueira M., Scolaro B., Thomazini M., Ferro-Furtado R., de Castro I.A., et al. 2018. Enhancing stability of echium seed oil and beta-sitosterol by their coencapsulation by complex coacervation using different combinations of wall materials and crosslinkers. Food Chem. 252:277–284. 10.1016/j.foodchem.2018.01.121
da Silveira T.F.F., Cajaíba L.M., Valentin L., Baréa B., Villeneuve P., and Castro I.A. 2020. Effect of sinapic acid ester derivatives on the oxidative stability of omega-3 fatty acids rich oil-in-water emulsions. Food Chem. 309:125586. 10.1016/j.foodchem.2019.125586
Espinosa R.R., Inchingolo R., Alencar S.M., Rodriguez-Estrada M.T., Castro I.A. 2015. Antioxidant activity of phenolic compounds added to a functional emulsion containing omega-3 fatty acids and plant sterol esters. Food Chem. 182:95–104. 10.1016/j.foodchem.2015.02.130
Garssen G.J., Vliegenthart J.F.G., and Boldingh J. 1971. An anaerobic reaction between lipoxygenase, linoleic acid and its hydroperoxides. Biochem. J. 122: 327–332. 10.1042/bj1220327
Grosshagauer S., Steinschaden R., and Pignitter M. 2019. Strategies to increase the oxidative stability of cold pressed oils. LWT. 106:72–77. 10.1016/j.lwt.2019.02.046
Hammer M., and Schieberle P. 2013. Model studies on the key aroma compounds formed by an oxidative degradation of ω-3 fatty acids initiated by either copper(II) ions or lipoxygenase. J. Agric. Food Chem. 61(46):10891–108900. 10.1021/jf403827p
Hayward S., Cilliers T., and Swart P. 2016. Lipoxygenases: From isolation to application. Comprehensive reviews in food science and food safety. 00:1–13. 10.1111/1541-4337.12239
Hong Y.L., Yeh S.L., Chang C.Y., and Hu M.L. 2000. Total plasma malondialdehyde levels in 16 Taiwanese college students determined by various thiobarbituric acid tests and an improved high-performance liquid chromatography-based method. Clinical Biochemistry. 33(8):619–625. 10.1016/s0009-9120(00)00177-6
Jacobsen, C., Hartvigsen, K., Lund, P., Meyer, A. S., Adler-Nissen, J., & Hølmer, G. (2010). xidation in fish oil enriched mayonnaise: Aspects of oil quality, fish oil addition,., and tocopherol content. European Journal of Lipid Science and Technology, 102(8–9), 624–632.
Kim H.J., Lee H.O., and Min D.B. 2007. Effects and prooxidant mechanisms of oxidized alpha-tocopherol on the oxidative stability of soybean oil. JFST. 72(4):C223–C230. 10.1111/j.1750-3841
Mach F., Baigent C., Catapano A.L., Koskinas K.C., Casula M., Badimon L., et al. 2019. 2019 ESC/EAS guidelines for the management of dyslipidaemias: Lipid modification to reduce cardiovascular risk. Eur. Heart J. 41(1):111–188. 10.1093/eurheartj/ehz455
Martin-Rubio, A. S., Sopelana, P., Ibargoitia, M. L., & Guillén, M. D. (2018). Prooxidant effect of α-tocopherol on soybean oil. Global monitoring of its oxidation process under accelerated storage conditions by 1H nuclear magnetic resonance. Food Chemistry, 245, 312–323. 10.1016/j.foodchem.2017.10.098
Mateos R., Goya L., and Bravo L. 2004. Determination of malondialdehyde (MDA) by high-performance liquid chromatography in serum and liver as a biomarker for oxidative stress: Application to a rat model for hypercholesterolemia and evaluation of the effect of diets rich in phenolic antioxidants from fruits. J. Chrom. B. 827(1):76–82. 10.1016/j.jchromb.2005.04.035
Matoba T., Hidaka H., Narita H., Kitamura K., Kaizuma N., and Kito, M. 1985. Lipoxygenase-2 Isozyme is responsible for generation of n-hexanal in soybean homogenate. J. Agric. Food Chem. 33: 852–855. 10.1021/jf00065a021
Mihaylova, D., Gandova, V., Deseva, I., Tschuikowa, S., Schalow, S., & Westphal, G. (2020). Arrhenius equation modeling for the oxidative stability evaluation of Echium oil enriched with a natural preservative. European Journal of Lipid Science and Technology, 122(10),
Minhas A.M.K., Jain V., Li M., Ariss R.W., Fudim M., Michos E.D., et al. 2023 Family income and cardiovascular disease risk in American adults. Sci. Rep. 13:1–10. 10.1038/s41598-023-27474-x.
Matoba T., Hidaka H., Narita H., Kitamura K., Kaizuma N., and Kito M. 1985. Lipoxygenase-2 Isozyme is responsible for generation of n-hexanal in soybean homogenate. J. Agric. Food Chem. 33: 852–855. 10.1021/jf00065a021
Minhas A.M.K., Jain V., Li M., Ariss R.W., Fudim M., Michos E.D., et al. 2023 Family income and cardiovascular disease risk in American adults. Sci. Rep. 13:1–10. 10.1038/s41598-023-27474-x.
Morales A., Clerici M.T.P.S., and Castro, I.A. 2012. Oxidative stability of model systems and processed foods enriched with omega-3 rich oils. Crit. Rev. Food Sci. Nutr. 52(9):850–873. 10.1080/10408398.2010.507697
Nogueira, M. S., Scolaro, B., Milne, G. L., & Castro, I. A. (2019). Oxidation products from omega-3 and omega-6 fatty acids during a simulated shelf life of edible oils. LWT, 101, 113–122. 10.1016/j.lwt.2018.11.044
Nawar W.W. 1996. Lipids. In Fennema, O.R. (Ed.), Food Chemistry (3rd ed., pp. 225–319). New York: Marcel Dekker Inc.
O’Keefe S.F., and Pike O.A. 2010. Fat characterization. In Nielsen S.S. (Ed.), Food Analysis (4th ed., pp. 239–260). Springer. 10.1007/978-1-4419-1478-1_14
O’Brien R.D. 2008. Fats and Oils: Formulating and Processing for Applications (3rd ed.). CRC Press.
Olsen, R.E., Waagbø, R., Melle, W., Ringø, E, Lall, S.P. Alternative marine sources. In Fish Oil Replacement and Alternative Lipid Sources in Aquaculture Feeds; Turchini, G.M., Ng, W.-K., Tocher, D.R., eds.; CRC Press: Boca Raton, FL, USA, 2011; pp. 267–324, ISBN 9781439808627
Prasad, P., Anjali, P., & Sreedhar, R. V. (2021). Plant-based stearidonic acid as a sustainable source of omega-3 fatty acid with functional outcomes on human health. *Critical Reviews in Food Science and Nutrition, 61(10), 1725–1737. 10.1080/10408398.2020.1765137
Roschel, G. G., da Silveira, T. F. F., Cajaíba, L. M., Ferrari, R. A., & Castro, I. A. (2021). Combination of natural strategies to improve the oxidative stability of echium seed oil. Journal of Food Science, 86(2), 411–419. 10.1111/1750-3841.15590
Roth G.A., Mensah, G.A., Johnson C.O., Addolorato G., Ammirati E., Baddour L.M., et al. 2020. Global burden of cardiovascular diseases and risk factors, 1990–2019: Update from the GBD 2019 study. JACC. 76: 2982–3021. 10.1016/j.jacc.2020.11.010
Schön C., Trautmann A., Steinhart H., and Paschke A. 2002. Determination of soybean lipoxygenase activity by coupled optical and polarographic measurements. Anal. Bioanal. Chem. 373(6): 408–414. 10.1007/s00216-002-1365-6
Shantha, N. C., & Decker, E. A. (1994). Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids. Journal of AOAC International, 77(2), 421–424. PMid: 8199478.
Sherratt, S. C. R., Libby, P., Budoff, M. J., Bhatt, D. L., & Mason, R. P. (2023). Role of omega-3 fatty acids in cardiovascular disease: The debate continues. Current Atherosclerosis Reports, 25(1), 1–17. 10.1007/s11883-022-01075-x
Singh, P., Arif, Y., Miszczuk, E., Bajguz, A., & Hayat, S. (2022). Specific roles of lipoxygenases in development and responses to stress in plants. Plants, 11(7), 979. 10.3390/plants11070979
So, J., Wu, D., Lichtenstein, A. H., Tai, A. K., Matthan, N. R., Maddipati, K. R., Lamon-Fava, S. (2021). EPA and DHA differentially modulate monocyte inflammatory response in subjects with chronic inflammation in part via plasma specialized pro-resolving lipid mediators: A randomized, double-blind, crossover study. Atherosclerosis, 316, 90–98. 10.1016/j.atherosclerosis.2020.11.018
Song J., Zhao X., and Yang X. 2020. Echium oil in a controlled in vitro digestion model: The impact of emulsification on bioaccessibility and oxidative stability. Food Chem. 332:127394. 10.1016/j.foodchem.2020.127394
Sun W., Miao H., Zhao H., Chen L., Huang Z., Yang Y., et al. 2016. Comparison of three different methods for the determination of lipoxygenase activity in oat. J. Food Sci. Technol. 53(10): 3677–3683. 10.1007/s13197-016-2314-0
Takic, M., Pokimica, B., Petrovic-Oggiano, G., & Popovic, T. (2022). Effects of dietary α-linolenic acid treatment and the efficiency of its conversion to eicosapentaenoic and docosahexaenoic acids in obesity and related diseases. Molecules, 27(14), 4471. 10.3390/molecules27144471
Tian, Q., & Hua, Y. (2021). Oxidation reactions in model systems simulating the processing of soybeans into soymilk: Role of lipase and lipoxygenase in volatile flavors formation. International Journal of Food Properties, 24(1), 192–202. 10.1080/10942912.2021.1873363
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Jan 4, 2025
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Cesconetto-Bisinotto, M., Dourado Chedid, L., Souza Gouveia, A. de, de Oliveira Ramos, H. J., García-Moreno, P. J., & Alves Castro, I. (2025). Oxidative stability of echium crude oil during the cold-press extraction process. Italian Journal of Food Science, 37(2), 12-22. https://doi.org/10.15586/ijfs.v37i2.2878
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Cesconetto-Bisinotto, M., Dourado Chedid, L., Souza Gouveia, A. de, de Oliveira Ramos, H. J., García-Moreno, P. J., & Alves Castro, I. (2025). Oxidative stability of echium crude oil during the cold-press extraction process. Italian Journal of Food Science, 37(2), 12-22. https://doi.org/10.15586/ijfs.v37i2.2878