Enzymatic Acidolysis of Fish Oil with Milk Fat Fatty Acids for the Synthesis of Structured Lipid
DOI:
https://doi.org/10.3923/pjn.2019.372.378Keywords:
Enzymatic acidolysis, fish oil, milk fat fatty acid, Polyunsaturated fatty acid, structured lipidAbstract
Background and Objective: Structured lipids (SLs) consisting of saturated fatty acids (SFAs) at the outside position (sn-1,3) and polyunsaturated fatty acids (PUFAs) at the sn-2 position have good nutritional values and high stabilities for oxidation. The objective of this research was to synthesize SLs containing SFAs at the sn-1,3 position and PUFAs at the sn-2 position by the enzymatic acidolysis of fish oil with milk fat fatty acids (MFFAs). Materials and Methods: Fish oil, containing high PUFAs, was combined with milk fat that was hydrolyzed to MFFAs through saponification with KOH followed by acidification with HCl and extraction with hexane. SLs were synthesized by acidolysis using a specific lipase from Mucor miehei. The factors of substrate ratio and reaction time were studied. The SLs were analyzed for the fatty acid compositions, acylglycerol profiles and positional distributions of the fatty acids at sn-2 and sn-1,3. Results: The increasing proportions of the MFFAs and the increase in the reaction time increased the incorporation of SFA into the SLs. An acidolysis ratio of fish oil to MFFAs of 1:3 and a reaction time of 6 h at 40°C resulted in a good SL, where EPA and DHA were incorporated at sn-2 at 13.20 and 12.85%, respectively and SFAs (capric, lauric, myristic, palmitic and stearic acids) at sn-1,3 at approximately 58.25%. The SL had an acylglycerol profile containing triacylglycerol (TAG), diacylglycerol (DAG) and monoacylglycerol (MAG) at 69.45, 22.32 and 8.23%, respectively. Conclusion: The optimum enzymatic acidolysis conditions for synthesizing the SL were a molar ratio of fish oil to MFFAs of 1:3 and a reaction time of 6 h at 40°C. The SL has the potential to fortify high-nutrition dairy products.
References
Osborn, H.T. and C.C. Akoh, 2002. Structured lipids-novel fats with medical, nutraceutical and food applications. Comp. Rev. Food Sci., 1: 110-120.
Kim, B.H. and C.C. Akoh, 2015. Recent research trends on the enzymatic synthesis of structured lipids. J. Food Sci., 80: C1713-C1724.
Subroto, E., Supriyanto, T. Utami and C. Hidayat, 2018. Enzymatic glycerolysis-interesterification of palm stearin-olein blend for synthesis structured lipid containing high mono-and diacylglycerol. Food Sci. Biotechnol.
Shahidi, F. and P. Ambigaipalan, 2018. Omega-3 polyunsaturated fatty acids and their health benefits. Annu. Rev. Food Sci. Technol., 9: 345-381.
Endo, Y., S. Hoshizaki and K. Fujimoto, 1997. Oxidation of synthetic triacylglycerols containing eicosapentaenoic and docosahexaenoic acids: Effect of oxidation system and triacylglycerol structure. J. Am. Oil Chem. Soc., 74: 1041-1045.
Gunstone, F.D., 1999. Enzymes as biocatalysts in the modification of natural lipids. J. Sci. Food Agric., 79: 1535-1549.
Paez, B.C., A.R. Medina, F.C. Rubio, P.G. Moreno and E.M. Grima, 2002. Production of structured triglycerides rich in n-3 polyunsaturated fatty acids by the acidolysis of cod liver oil and caprylic acid in a packed-bed reactor: Equilibrium and kinetics. Chem. Eng. Sci., 57: 1237-1249.
Hita, E., A. Robles, B. Camacho, A. Ramirez and L. Esteban et al., 2007. Production of structured triacylglycerols (STAG) rich in docosahexaenoic acid (DHA) in position 2 by acidolysis of tuna oil catalyzed by lipases. Process Biochem., 42: 415-422.
Balcao, V.M. and F.X. Malcata, 1998. Interesterification and acidolysis of butterfat with oleic acid by Mucor javanicus lipase: Changes in the pool of fatty acid residues. Enzyme Microb. Technol., 22: 511-519.
Nadeem, M., M. Abdullah, A. Javid, A.M. Arif and T. Mahmood, 2012. Evaluation of functional fat from interesterified blends of butter oil and Moringa oleifera oil. Pak. J. Nutr., 11: 823-827.
Subroto, E., T. Tensiska, R. Indiarto and C. Hidayat, 2013. The effect of substrat ratio fish oil and milk fat on synthesis of structured lipid by enzimatic transesterification. Int. J. Adv. Sci. Eng. Infor. Technol., 3: 117-121.
Kim, I.H. and C.G. Hill Junior, 2006. Lipase-catalyzed acidolysis of menhaden oil with pinolenic acid. J. Am. Oil Chem. Soc., 83: 109-115.
AOCS., 2004. Official Methods and Recommended Practices of the American Oil Chemists' Society. American Oil Chemist's Society Press, Champaign, IL., USA.
Fuchs, B., R. Suß, K. Teuber, M. Eibisch and J. Schiller, 2011. Lipid analysis by thin-layer chromatography-a review of the current state. J. Chromatogr. A, 1218: 2754-2774.
Jin, Y., Y. Yuan, L. Gao, R. Sun, L. Chen, D. Li and Y. Zheng, 2017. Characterization and functional analysis of a type 2 diacylglycerol acyltransferase (DGAT2) gene from oil palm (Elaeis guineensis Jacq.) mesocarp in Saccharomyces cerevisiae and transgenic Arabidopsis thaliana. Front. Plant Sci., Vol. 8.
Torres, C.F., F. Munir, R.M. Blanco, C. Otero and C.G. Hill Junior,, 2002. Catalytic transesterification of corn oil and tristearin using immobilized lipases from Thermomyces lanuginosa. J. Am. Oil Chem. Soc., 79: 775-781.
Zock, P.L., J.H. de Vries, N.J. de Fouw and M.B. Katan, 1995. Positional distribution of fatty acids in dietary triglycerides: Effects on fasting blood lipoprotein concentrations in humans. Am. J. Clin. Nutr., 61: 48-55.
Lubary, M., G.W. Hofland and J.H. Ter Horst, 2011. The potential of milk fat for the synthesis of valuable derivatives. Eur. Food Res. Technol., 232: 1-8.
Ozturk, T., G. Ustun and H.A. Aksoy, 2010. Production of medium-chain triacylglycerols from corn oil: Optimization by response surface methodology. Bioresour. Technol., 101: 7456-7461.
Subroto, E., C. Hidayat and Supriyadi, 2010. Enzymatic interesterification of fish oil with lauric acid for the synthesis of structured lipid. J. Teknol. Ind. Pangan, 19: 105-112.
Akoh, C.C. and D.B. Min, 2002. Food Lipids: Chemistry, Nutrition and Biotechnology. Marcel Dekker, New York.
Xu, X., H. Mu, A.R.H. Skands, C.E. Hoy and J. Adler-Nissen, 1999. Parameters affecting diacylglycerol formation during the production of specificâ€structured lipids by lipaseâ€catalyzed interesterification. J. Am. Oil Chem. Soc., 76: 175-181.
Xu, X., A.R.H. Skands, C.E. Hoy, H. Mu, S. Balchen and J. Adler-Nissen, 1998. Production of specific-structured lipids by enzymatic interesterification: Elucidation of acyl migration by response surface design. J. Am. Oil Chem. Soc., 75: 1179-1186.
Noor, I.M., M. Hasan and K.B. Ramachandran, 2003. Effect of operating variables on the hydrolysis rate of palm oil by lipase. Process Biochem., 39: 13-20.
Subroto, E., M.F. Wisamputri, Supriyanto, T. Utami and C. Hidayat, 2018. Enzymatic and chemical synthesis of high mono-and diacylglycerol from palm stearin and olein blend at different type of reactor stirrers. J. Saudi Soc. Agric. Sci., (In Press).
Yankah, V.V. and C.C. Akoh, 2000. Lipaseâ€catalyzed acidolysis of tristearin with oleic or caprylic acids to produce structured lipids. J. Am. Oil Chem. Soc., 77: 495-500.
Carrin, M.E. and G.H. Crapiste, 2008. Enzymatic acidolysis of sunflower oil with a palmitic-stearic acid mixture. J. Food Eng., 84: 243-249.
Lo, S.K., C.P. Tan, K. Long, M.S.A. Yusoff and O.M. Lai, 2008. Diacylglycerol oil-properties, processes and products: A review. Food Bioprocess Technol., 1: 223-233.
Matsuo, N. and I. Tokimitsu, 2001. Metabolic characteristics of diacylglycerol oil. Inform, 12: 1098-1102.
Rodrigues, R.C. and R. Fernandez-Lafuente, 2010. Lipase from Rhizomucor miehei as a biocatalyst in fats and oils modification. J. Mol. Catal. B: Enzym., 66: 15-32.
Downloads
Published
Issue
Section
License
Copyright (c) 2019 The Author(s)
This work is licensed under a Creative Commons Attribution 4.0 International License.
This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution and reproduction in any medium, provided the original author and source are credited.
