Concentration of Docosahexaenoic Acid (DHA) by Selective Alcoholysis Catalyzed by Lipases

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• 作者：L. Martín Valverde (1)
  P. A. González Moreno (1)
  A. Rodríguez Quevedo (1)
  E. Hita Pe?a (1)
  M. J. Jiménez Callejón (1)
  L. Esteban Cerdán (1)
  E. Molina Grima (1)
  A. Robles Medina (2) arobles@ual.es
• 关键词：Docosahexaenoic acid (DHA) – Lipase – Acylglycerols – Lipozyme TL IM – Short ; path distillation
• 刊名：Journal of the American Oil Chemists' Society
• 出版年：2012
• 出版时间：September 2012
• 年：2012
• 卷：89
• 期：9
• 页码：1633-1645
• 全文大小：498.5 KB
• 参考文献：1. Simopoulos AP (1999) Essential fatty acids in health and chronic disease. Am J Clin Nutr 70:560S–569S
  2. Connor WE (2000) Importance of n-3 fatty acids in health and disease. Am J Clin Nutr 71(1 Suppl):171S–175S
  3. Dyerberg J, Bang HO, Stoffersen E (1978) Eicosapentaenoic acid and prevention of thrombosis and atherosclerosis? Lancet 2:117–119
  4. Bao DQ, Mori TA, Burke V, Puddey IB, Beilin J (1998) Effects of dietary fish and weight reduction on ambulatory blood pressure in overweight hypertensives. Hypertension 32:710–717
  5. Mori TA, Woodman RJ (2006) The independent effects of eicosapentaenoic acid and docosahexaenoic acid on cardiovascular risk factors in humans. Curr Opin Clin Nutr Metab Care 9:95–104
  6. Sijben JWC, Calder PC (2008) Differential immunomodulation with long-chain n-3 PUFA in health and chronic disease. Proc Nutr Soc 66:237–259
  7. McCann JC, Ames BN (2005) Is docosahexaenoic acid, an n-3 long-chain polyunsaturated fatty acid, required for development of normal brain function? An overview of evidence from cognitive and behavioral tests in humans and animals. Am J Clin Nutr 82:281–295
  8. Ryan AS, Astwood JD, Gautier S, Kuratko CN, Nelson EB, Salem N Jr (2010) Effects of long-chain polyunsaturated fatty acid supplementation on neurodevelopment in childhood: a review of human studies. Prostaglandins Leukot Essent Fatty Acids 82:305–314
  9. Eilander A, Hundscheid DC, Osendarp SJ, Transler C, Zock PL (2007) Effects of n-3 long chain polyunsaturated fatty acid supplementation on visual and cognitive development throughout childhood: a review of human studies. Prostaglandins Leukot Essent Fatty Acids 76:189–203
  10. Ramakrishnan U, Imhoff-Kunsch B, DiGirolamo AM (2009) Role of docosahexaenoic acid in maternal and child mental health. Am J Clin Nutr 89(suppl):958S–962S
  11. Shahidi F, Wanasundara UN (1998) Omega-3 fatty acid concentrates: nutritional aspects and production technologies. Trends Food Sci Technol 9:230–240
  12. Rubio-Rodríguez N, Beltrán S, Jaime I, de Diego SM, Sanz MT, Carballido JR (2010) Production of omega-3 polyunsaturated fatty acid concentrates: a review. Innov Food Sci Emerg Technol 11:1–12
  13. Robles Medina A, Giménez Giménez A, García Camacho F, Sánchez Pérez JA, Molina Grima E, Contreras Gómez A (1995) Concentration and purification of stearidonic, eicosapentaenoic, and docosahexaenoic acids from cod liver oil and the marine microalga Isochrysis galbana. J Am Oil Chem Soc 72:575–583
  14. Ibá?ez González MJ, Robles Medina A, Molina Grima E, Giménez Giménez A, Carstens M, Esteban Cerdán L (1998) Optimization of fatty acid extraction from Phaeodactylum tricornutum UTEX 640 Biomass. J Am Oil Chem Soc 75:1735–1740
  15. Dyerberg J, Madsen P, M?ller JM, Aardestrup I, Schmidt EB (2010) Bioavailability of marine n-3 fatty acid formulations. Prostaglandins Leukot Essent Fatty Acids 83:137–141
  16. Tamai T, Murota I, Maruyama K, Baba T, Toyama T, Watanabe N, Kudo N, Kawashima Y (2007) Effects of supplemented diacylglycerol rich in docosahexaenoic acid on serum triacylglycerol in a diet-induced hyperlipidemic model of rats are essentially equivalent to those of triacylglycerol rich in docosahexaenoic acid. Biol Pharm Bull 30:2381–2388
  17. Haraldsson GG (1989) The application of lipases for modification of fats and oils, including marine oils. In: Bohtta R, Voigt MN (eds) Advanced in Fisheries Technology for Increased Profitability. Technomic Publishing, Lancaster, pp 337–357
  18. Haraldsson GG, Kristinson F, Sigurdardottir R, Gudmundsson FF, Breivik H (1997) The preparation of concentrates of eicosapentaenoic acid docosohexaenoic acid by lipase-catalyzed transesterification of fish oil with ethanol. J Am Oil Chem Soc 74:1419–1424
  19. Miller C, Austin H, Posorske L, González J (1988) Characteristics of an immobilized lipase for the commercial synthesis of esters. J Am Oil Chem Soc 65:927–931
  20. Shimada Y, Sugihara A, Nakano H, Kuramoto T, Nagao T, Gemba M, Tominaga Y (1997) Purification of docosohexaenoic acid by selective esterification of fatty acids from tuna oil with Rhizopus delemar lipase. J Am Oil Chem Soc 74:97–101
  21. Ramírez Fajardo A, Esteban Cerdán L, Robles Medina A, Mu?ío Martínez MM, Hita Pe?a E, Molina Grima E (2006) Concentration of eicosapentaenoic acid by selective esterification using lipase. J Am Oil Chem Soc 83:215–221
  22. Halldorsson A, Kristinson B, Glynn C, Haraldsson GG (2003) Separation of EPA and DHA in fish oil by lipase-catalyzed esterification with glycerol. J Am Oil Chem Soc 80:915–921
  23. Lyberg A-M, Adlercreutz P (2008) Lipase-catalyzed enrichment of DHA and EPA in acylglycerols resulting from squid oil ethanolysis. Eur J Lipid Sci Technol 110:317–324
  24. Haraldsson GG, Kristinsson B (1998) Separation of eicosapentaenoic acid and docosahexaenoic acid in fish oil by kinetic resolution using lipase. J Am Oil Chem Soc 75:1551–1556
  25. Hita E, Robles A, Camacho B, Ramírez A, Esteban L, Jiménez MJ, Mu?ío MM, González PA, Molina E (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
  26. 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
  27. Lepage G, Roy C (1984) Improved recovery of fatty acids acid through direct transesterification without prior extraction or purification. J Lipid Res 25:1391–1396
  28. Rodríguez-Ruiz J, Belarbi E, García Sánchez JL, López Alonso D (1998) Rapid simultaneous lipid extraction and transesterification for fatty acids analysis. Biotechnol Techniq 12:689–691
  29. Shimada Y, Ogawa J, Watanabe Y, Nagao T, Kawashima A, Kobayashi T, Shimizu S (2003) Regiospecific analysis by ethanolysis of oil with immobilized Candida antarctica lipase. Lipids 38:1281–1286
  30. Robles A, Jiménez MJ, Esteban L, González PA, Martín L, Rodríguez A, Molina E (2011) Enzymatic production of human milk fat substitute containing palmitic and docosohexaenoic acids at sn-2 position and oleic acid at sn-1,3 positions, LWT. Food Sci Technol 44:1986–1992
  31. Akoh CC, Chang SS, Lee GG, Shaw JJ (2007) Enzymatic approach to biodiesel production. Agric Food Chem 55:8995–9005
  32. Camacho Páez B, Robles Medina A, Camacho Rubio F, González Moreno P, Molina Grima E (2002) Production of structured triacylglycerides 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
  33. González Moreno PA, Robles Medina A, Camacho Rubio F, Camacho Páez B, Molina Grima E (2004) Production of Structured lipids by acidolysis of an EPA-enriched fish oil and caprylic acid in a packed bed reactor: analysis of three different operation modes. Biotechnol Prog 20:1044–1052
  34. Shimada Y, Watanabe Y, Sugihara A, Tominaga Y (2002) Enzymatic alcoholysis for biodiesel fuel production and application of the reaction to oil processing. J Mol Catal B Enzym 17:133–142
• 作者单位：1. Department of Chemical Engineering, University of Almería, 04120 Almería, Spain2. Chemical Engineering Department, Almería University, 04120 Almería, Spain
• ISSN：1558-9331

文摘

The aim of this work was to obtain acylglycerols from tuna oil (23 % weight DHA) rich in docosahexaenoic acid (DHA) by selective ethanolysis, catalyzed by lipases. First, seven immobilized lipases were tested and the best DHA concentration and recovery in the acylglycerol fraction were attained with Lipozyme TL IM? from Thermomyces lanuginosus, Lipozyme RM IM from Rhizomucor miehei, and lipase from Thermomyces lanuginosus immobilized on Immobead 150. As it is the cheapest, Lipozyme TL IM? was selected to optimize the reaction conditions. The influence of temperature, reaction time, and ethanol/oil and lipase/oil ratios were studied. Under the optimized conditions (35 °C, ethanol/oil molar ratio 2.3, lipase/oil ratio 5 % weight and 48 h) and for a 56 % conversion, acylglycerols were obtained with a 45 % DHA concentration and 90 % recovery. In these optimized conditions the reaction was scaled up to 766 g of tuna oil and carried out in a batch stirred tank reactor, with the lipase contained in a cartridge filter attached to the stirring rod. The results were similar to those obtained on the smaller scale. The DHA-enriched acylglycerols were separated from the ethyl esters by evaporation of the latter in a short-path vacuum distiller, where the influence of distillation temperature was studied. At 170 °C DHA-rich acylglycerols (44 % DHA) were recovered in the residue with 94.5 % purity and 72 % recovery.