Use of Echium oil fatty acids and tricaprylin as substrates of enzymatic interesterification for the production of structured lipids

Authors

DOI:

https://doi.org/10.3989/gya.0996171

Keywords:

Echium oil, Enzymatic acidolysis, Lipozyme® RM IM, Response surface methodology, Stearidonic acid, Tricaprylin

Abstract


Structured lipids (SLs) were produced from the free fatty acids of Echium oil and tricaprylin by enzymatic acidolysis reactions. Lipozyme® RM IM, immobilized sn-1,3 specific lipase was used in the enzymatic reactions. In order to optimize the incorporation of stearidonic acid (SDA), three factors were chosen [Reaction temperature (50-60 ºC), reaction time (6-12 hour) and substrate molar ratio (3-6 mol/mol (total free fatty acids/tricaprylin)] for the application of response surface methodology (RSM) using a central composite circumscribed design (CCC) with five levels. The optimum temperature, time and substrate molar ratio obtained from the models were 60 ºC; 6 h, 6 mol/mol, respectively. Furthermore, SLs with 6.2% SDA content at sn-2 position were produced by scaling up the process. SL was obtained with nearly 78-79% of long-chain fatty acids at the sn-2 position. According to the melting profile analysis, the melting peaks of tricaprylin and Echium oil were sharper and narrower while the SL had more broadened peaks.

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References

Akoh CC, Sellappan S, Fomuso LB, Yankah, VV. 2002. Enzymatic synthesis of structured lipids, in Kuo TM, Gardner HW (Eds), Lipid Biotechnology, Marcel Dekker, Inc., New York, pp. 432-460.

AOCS Official Method Cj 1-94. 1989. Official methods and recommended practices of the American Oil Chemists' Society, in Firestone D (Ed), 4th edn, American Oil Chemists' Society, Champaign IL.

Bilgiç S, Ye?ilçubuk N?. 2012. Lipase-Catalyzed Acidolysis of Olive Oil with Echium Oil Stearidonic Acid: Optimization by Response Surface Methodology. J. Am. Oil Chem. Soc. 89, 1971-1980. https://doi.org/10.1007/s11746-012-2097-8

Chávez-Servín JL, Castellote AI, Martín M, Chifré R, López- Sabater MC.2009. Stability during storage of LC-PUFA-supplemented infant formula containing single cell oil or egg yolk, Food Chem. 113, 484-492. https://doi.org/10.1016/j.foodchem.2008.07.082

Chopra R, Rastogi NK, Sambaiah K. 2011. Enrichment of rice bran oil with ?-linolenic acid by enzymatic acidolysis: Optimization of parameters by response surface methodology. Food Bioproc. Tech. 4, 1153-1163. https://doi.org/10.1007/s11947-009-0191-1

Gökçe G, ?ahin-Ye?ilçubuk N, Üstün G. 2013. Enzymatic production of low-calorie structured lipid from Echium seed oil and lauric acid: optimisation by response surface methodology. J. Food Sci. Technol. 48, 1383–1389. https://doi.org/10.1111/ijfs.12099

Guil-Guerrero JL, Gómez-Mercado F, García-Maroto F, Campra-Madrid P. 2000. Occurrence and characterization of oils rich in ?-linolenic acid Part I: Echium seeds from Macaronesia. Phytochem. 53, 451-456. https://doi.org/10.1016/S0031-9422(99)00549-X

Hita E., Robles A, Camacho B, González PA, Esteban L, Jiménez MJ, Mu-ío MM, Molina E. 2009. Production of structured triacylglycerols by acidolysis catalyzed by lipases immobilized in a packed bed reactor. Biochem. Eng. J. 46, 257–264. https://doi.org/10.1016/j.bej.2009.05.015

Ifeduba EA, Akoh CC. 2014. Modification of stearidonic acid soybean oil by ımmobilized Rhizomucor miehei lipase to ıncorporate caprylic acid. J. Am. Oil Chem. Soc. 91, 953- 965. https://doi.org/10.1007/s11746-014-2433-2

Jennings BH, Akoh CC. 1999. Enzymatic modification of triacylglycerols of high eicosapentaenoic and docosahexaenoic acids content to produce structured lipids. J. Am. Oil Chem. Soc. 76, 1133-1137. https://doi.org/10.1007/s11746-999-0085-4

Kim H-R, Hou CT, Lee K-T, Kim BH, Kim I-H. 2010. Enzymatic synthesis of structured lipids using a novel cold-active lipase from Pichia lynferdii NRRL Y-7723. Food Chem. 122, 846–849. https://doi.org/10.1016/j.foodchem.2010.03.067

Kleiner L, Vázquez L, Akoh CC. 2012. Increasing Stearidonic Acid (SDA) in Modified Soybean Oil by Lipase-Mediated Acidolysis. J. Am. Oil Chem. Soc. 89, 1267–1275. https://doi.org/10.1007/s11746-012-2108-9

Lee J-H, Shin J-A, Lee J-H, Lee K-T. 2004. Production of lipase-catalyzed structured lipids from safflower oil with conjugated linoleic acid and oxidation studies with rosemary extracts. Food Res. Int. 37, 967-974. https://doi.org/10.1016/j.foodres.2004.06.005

Lumor SE, Akoh CC. 2005. Enzymatic incorporation of stearic acid into a blend of palm olein and palm kernel oil: Optimization by response surface methodology. J. Am. Oil Chem. Soc. 82, 412-426. https://doi.org/10.1007/s11746-005-1087-0

Matulka RA, Noguchi O, Nosaka N. 2006. Safety evaluation of a medium- and long-chain triacylglycerol oil produced from medium-chain triacylglycerols and edible vegetable oil. Food Chem. Toxicol. 44, 1530–1538. https://doi.org/10.1016/j.fct.2006.04.004 PMid:16753249

Mu H, Høy C-E. 2004. The digestion of dietary triacylglycerols. J. Prog. Lipid Res. 43, 105–133. https://doi.org/10.1016/S0163-7827(03)00050-X

Nunes PA, Pires-Cabral P, Ferreira-Dias S. 2011. Production of olive oil enriched with medium chain fatty acids catalysed by commercial immobilised lipases. Food Chem. 127, 993– 998. https://doi.org/10.1016/j.foodchem.2011.01.071 PMid:25214088

Osborn HT, Akoh CC. 2002. Structured lipids- novel fats with medical, nutraceutical, and food applications. Compr. Rev. Food Sci. Food Saf. 3, 110-120. https://doi.org/10.1111/j.1541-4337.2002.tb00010.x

Özcan T. 2008. Analysis of the total oil and fatty acid composition of seeds of some Boraginaceae taxa from Turkey. Plant Syst. Evol. 274, 143–153. https://doi.org/10.1007/s00606-008-0039-6

Öztürk T, Ustun G, Aksoy HA. 2010. Production of medium-chain triacylglycerols from corn oil: Optimization by response surface methodology. Bioresour. Technol. 101, 7456–7461. https://doi.org/10.1016/j.biortech.2010.04.096 PMid:20576567

Pina-Rodriguez AM, Akoh CC. 2009. Enrichment of amaranth oil with ethyl palmitate at the sn-2 position by chemical and enzymatic synthesis. J. Agric. Food Chem. 57, 4657- 4662. https://doi.org/10.1021/jf900242g PMid:19413361

Rao R, Manohar B, Sambaiah K, Lokesh BR. 2002. Enzymatic acidolysis in hexane to produce n-3 or n-6 FA-enriched structured lipids from coconut oil: Optimization of reactions by response surface methodology. J. Am. Oil Chem. Soc. 79, 885-890. https://doi.org/10.1007/s11746-002-0574-7

Rubin M, Moser A, Vaserberg N, Greig F, Levy, Spivak H, et al. 2000. Structured triacylglycerol emulsion, containing both medium- and long-chain fatty acids, in long-term home parenteral nutrition: a double-blind randomized cross-over study. Nutrition 16, 95–100. https://doi.org/10.1016/S0899-9007(99)00249-X

Sahin N, Akoh CC, Karaali A. 2005a. Lipase-catalyzed acidolysis of tripalmitin with hazelnut oil fatty acids and stearic acid to produce human milk fat substitutes. J. Agric. Food Chem. 53, 5779-5783. https://doi.org/10.1021/jf050465e PMid:15998148

Sahin N, Akoh CC, Karaali A. 2005b. Enzymatic production of human milk fat substitutes containing ?-linolenic acid: Optimization of reactions by response surface methodology. J. Am. Oil Chem. Soc. 82, 549–557. https://doi.org/10.1007/s11746-005-1108-z

Surette ME. 2013. Dietary omega-3 PUFA and health: Stearidonic acid-containing seed oils as effective and sustainable alternatives to traditional marine oils. Mol. Nutr. Food Res. 57, 748–759. https://doi.org/10.1002/mnfr.201200706 PMid:23417895

Whelan J. 2009. Dietary stearidonic acid is a long chain (n-3) polyunsaturated fatty acid with potential health benefits. J. Nutr. 139, 5–10. https://doi.org/10.3945/jn.108.094268 PMid:19056654

Yang T, Xu X, He C, Li L. 2003. Lipase-catalyzed modification of lard to produce human milk fat substitutes. Food Chem. 80, 473-481. https://doi.org/10.1016/S0308-8146(02)00315-1

Yüksel A, Ye?ilçubuk N?. 2012. Enzymatic production of human milk fat analogues containing stearidonic acid and optimization of reactions by response surface methodology. LWT-Food Sci. Technol. 46, 210-216.

Published

2018-03-30

How to Cite

1.
Yüksel A, Şahin-Yeşilçubuk N. Use of Echium oil fatty acids and tricaprylin as substrates of enzymatic interesterification for the production of structured lipids. Grasas aceites [Internet]. 2018Mar.30 [cited 2024Mar.28];69(1):e236. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1703

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