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Lipase-Catalyzed Concentration of Stearidonic Acid in Modified Soybean Oil by Partial Hydrolysis

  • Original Paper
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Journal of the American Oil Chemists' Society

Abstract

Stearidonic acid (SDA, 18:4 ω-3) content of modified soybean oil (MSO) containing ~25 % SDA, was increased by lipase-catalyzed hydrolysis. Four non-immobilized powdered lipases, Lipase AY 30 (Candida rugosa), Lipase G 50 (Penicillium camembertii), Lipomod™ 34P-L034P (Candida cylindracea [rugosa]), Lipomod™ 36P-L036P (Rhizopus oryzae), and an immobilized lipase, Lipozyme RM IM (Rhizomucor miehei) were assessed, at various incubation times, for their ability to hydrolyze MSO and specificity toward SDA. The SDA enriched products contained triacylglycerols (TAG), diacylglycerols (DAG) and monoacylglycerols (MAG). Lipase 34P-L034P exhibited specificity towards SDA, while Lipase AY was able to discriminate against it. The highest total SDA content (40.9 mol%) was obtained with Amano AY lipase at 4 h incubation (66.2 % hydrolysis). Unhydrolyzed TAG, 1,3-DAG, 2,3(1)-DAG, and MAG contained 37.7 (56.4 at the sn-2 position), 41.6, 51.5 (54.9 at the sn-2 position), and 49.9 % SDA, respectively. Amano AY lipase was also used to hydrolyze previously SDA-enriched TAG (48.7 % SDA) obtained from low temperature crystallization of MSO. The highest total SDA content (62.7 mol%) was obtained at 12 h incubation (85.9 % hydrolysis). The SDA contents of unhydrolyzed TAG, 1,3-DAG, 2,3(1)-DAG, and MAG were 58.7 (65.7 at the sn-2 position), 71.2, 70.2 (52.9 at the sn-2 position), and 59.4 %, respectively.

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References

  1. Calder PC (2006) n-3 Polyunsaturated fatty acids, inflammation, and inflammatory diseases. Am J Clin Nutr 83:S1505–S1519

    Google Scholar 

  2. Kris-Etherton PM, Harris WS, Appel LJ (2002) Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation 106:2747–2757

    Article  Google Scholar 

  3. Larsson SC, Kumlin M, Ingelman-Sundberg M, Wolk A (2004) Dietary long-chain n-3 fatty acids for the prevention of cancer: a review of potential mechanisms. Am J Clin Nutr 79:935–945

    CAS  Google Scholar 

  4. Whelan J (2009) Dietary stearidonic acid is a long chain (n-3) polyunsaturated fatty acid with potential health benefits. Am J Clin Nutr 139:5–10

    CAS  Google Scholar 

  5. Jacobsen C, Let MB, Nielsen NS, Meyer AS (2008) Antioxidant strategies for preventing oxidative flavour deterioration of foods enriched with n-3 polyunsaturated lipids: a comparative evaluation. Trends Food Sci Tech 19:76–93

    Article  CAS  Google Scholar 

  6. Passi S, Cataudella S, Di Marco P, De Simone F, Rastrelli L (2002) Fatty acid composition and antioxidant levels in muscle tissue of different Mediterranean marine species of fish and shellfish. J Agric Food Chem 50:7314–7322

    Article  CAS  Google Scholar 

  7. Venegas-Calerón M, Sayanova O, Napier JA (2010) An alternative to fish oils: metabolic engineering of oil-seed crops to produce omega-3 long chain polyunsaturated fatty acids. Prog Lipid Res 49:108–119

    Article  Google Scholar 

  8. Guil-Guerrero J, Campra-Madrid P, Navarro-Juarez R (2003) Isolation of some PUFA from edible oils by argentated silica gel chromatography. Grasas y Aceites 54:116–121

    Article  CAS  Google Scholar 

  9. Kleiner-Shuhler L, Vazquez L, Akoh CC (2011) Purification of stearidonic acid from modified soybean oil by argentation silica gel column chromatography. J Am Oil Chem Soc 88:1161–1171

    Article  CAS  Google Scholar 

  10. Vazquez L, Akoh CC (2011) Concentration of stearidonic acid in free fatty acid and fatty acid ethyl ester forms from modified soybean oil by winterization. J Am Oil Chem Soc 88:1775–1785

    Article  CAS  Google Scholar 

  11. Vazquez L, Akoh CC (2012) Enrichment of stearidonic acid in modified soybean oil by low temperature crystallisation. Food Chem 130:147–155

    Article  CAS  Google Scholar 

  12. Rincón-Cervera MA, Guil-Guerrero JL (2010) Preparation of stearidonic acid-enriched triacylglycerols from Echium plantagineum seed oil. Eur J Lipid Sci Technol 112:227–232

    Article  Google Scholar 

  13. Teichert SA, Akoh CC (2011) Stearidonic acid soybean oil enriched with palmitic acid at the sn-2 position by enzymatic interesterification for use as human milk fat analogues. J Agric Food Chem 59:5692–5701

    Article  CAS  Google Scholar 

  14. Yüksel A, Sahin Yesilçubuk 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

    Article  Google Scholar 

  15. Kleiner L, Vazquez L, Akoh CC (2012) Increasing stearidonic acid (SDA) in modified soybean oil by lipase-mediated acidolysis. J Am Oil Chem Soc. doi:10.1007/s11746-012-2022-1

    Google Scholar 

  16. Wanasundara UN, Shahidi F (1998) Lipase-assisted concentration of n-3 polyunsaturated fatty acids in acylglycerols from marine oils. J Am Oil Chem Soc 75:945–951

    Article  CAS  Google Scholar 

  17. Xu X (2003) Engineering of enzymatic reactions and reactors for lipid modification and synthesis. Eur J Lipid Sci Technol 105:289–304

    Article  CAS  Google Scholar 

  18. Kahveci D, Xu X (2011) Repeated hydrolysis process is effective for enrichment of omega 3 polyunsaturated fatty acids in salmon oil by Candida rugosa lipase. Food Chem 129:1552–1558

    Article  CAS  Google Scholar 

  19. Bornscheuer UT (1995) Lipase-catalyzed synthesis of monoacylglycerols. Enzyme Microb Technol 17:578–586

    Article  CAS  Google Scholar 

  20. Weber N, Mukherjee KD (2004) Solvent-free lipase-catalyzed preparation of diacylglycerols. J Agric Food Chem 52:5347–5353

    Article  CAS  Google Scholar 

  21. Watanabe Y, Shimada Y, Yamauchi-Sato Y, Kasai M, Yamamoto T, Tsutsumi K, Tominaga Y, Sugihara A (2002) Synthesis of MAG of CLA with Penicillium camembertii lipase. J Am Oil Chem Soc 79:891–896

    Article  CAS  Google Scholar 

  22. Pinsirodom P, Parkin KL (2001) Lipase Assays. Curr Protoc Food Analyt Chem C3.1.1–C3.1.3

  23. Storch J, Zhou YX, Lagakos WS (2008) Metabolism of apical versus basolateral sn-2-monoacylglycerol and fatty acids in rodent small intestine. J Lipid Res 49:1762–1769

    Article  CAS  Google Scholar 

  24. Muñío MM, Esteban L, Robles A, Hita E, Jimenez MJ, Gonzalez PA, Camacho B, Molina E (2008) Synthesis of 2-monoacylglycerols rich in polyunsaturated fatty acids by ethanolysis of fish oil catalyzed by 1,3 specific lipases. Process Biochem 43:1033–1039

    Article  Google Scholar 

  25. AOAC International (1998) Official Methods of Analysis of AOAC International, 17th edn. Gaithersburg, MD, Method 996.01

  26. 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

    Article  CAS  Google Scholar 

  27. Luddy FE, Bardford RA, Herb SF, Magidman P, Riemenschneider RW (1964) Pancreatic lipase hydrolysis of triacylglycerides as a semi-micro technique. J Am Oil Chem Soc 41:639–696

    Article  Google Scholar 

  28. Rua ML, Diaz-Mauriño T, Fernandez VM, Otero C, Ballesteros A (1993) Purification and characterization of two distinct lipases from Candida cylindracea. Biochim Biophys Acta 1156:181–189

    Article  CAS  Google Scholar 

  29. Halldorson A, Kristinsson B, Haraldsson GG (2004) Lipase selectivity toward fatty acids commonly found in fish oil. Eur J Lipid Sci Technol 106:79–87

    Article  Google Scholar 

  30. Vasel B, Hecht H-J, Schmid RD, Schomburg D (1993) 3D-Structure of the lipase Rhizomucor miehei at different temperatures and computer modeling of a complex of the lipase with trilaurylglycerol. J Biotechnol 28:99–115

    Article  CAS  Google Scholar 

  31. Moore SR, McNeill GP (1996) Production of triglycerides enriched in long-chain n-3 polyunsaturated fatty acids from fish oil. J Am Oil Chem Soc 73:1409–1414

    Article  CAS  Google Scholar 

  32. Willis WM, Marangoni AG (1999) Assessment of lipase- and chemically catalyzed lipid modification strategies for the production of structured lipids. J Am Oil Chem Soc 76(443):450

    Google Scholar 

  33. Okada T, Morrissey MT (2007) Production of n-3 polyunsaturated fatty acid concentrate from sardine oil by lipase-catalyzed hydrolysis. Food Chem 103:1411–1419

    Article  CAS  Google Scholar 

  34. Sun T, Pigott GM, Herwig RP (2002) Lipase-assisted concentration of n-3 polyunsaturated fatty acids from viscera of farmed Atlantic salmon (Salmo salar L.). J Food Sci 67:130–136

    Article  CAS  Google Scholar 

  35. Hoshino T, Yamane T, Shimizu S (1990) Selective hydrolysis of fish oil by lipase to concentrate n-3 polyunsaturated fatty acids. Agric Biol Chem 54:1459–1467

    Article  CAS  Google Scholar 

  36. Lopez-Martinez JC, Campra-Madrid P, Guil-Guerrero JL (2004) γ-Linolenic acid enrichment from Borago officinalis seed oils and fatty acids by low temperature crystallization. J Biosci Bioeng 97:294–298

    CAS  Google Scholar 

  37. Campra-Madrid R, Guil-Guerrero JL (2002) High-performance liquid chromatographic purification of γ-linolenic acid (GLA) from the seed oil of two Boraginaceae species. Chromatographia 56:673–677

    Article  CAS  Google Scholar 

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Acknowledgments

The authors would like to acknowledge the grant from Monsanto Company (St. Louis, MO).

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Authors and Affiliations

  1. Department of Food Science and Technology, University of Georgia, Athens, GA, 30602-2610, USA

    Leslie Kleiner & Casimir C. Akoh

  2. Institute of Food Science Research (CIAL) (CSIC-UAM), UAM Cantoblanco Campus, Madrid, 28049, Spain

    Luis Vázquez

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  1. Leslie Kleiner
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  2. Luis Vázquez
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  3. Casimir C. Akoh
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Correspondence to Casimir C. Akoh.

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Kleiner, L., Vázquez, L. & Akoh, C.C. Lipase-Catalyzed Concentration of Stearidonic Acid in Modified Soybean Oil by Partial Hydrolysis. J Am Oil Chem Soc 89, 1999–2010 (2012). https://doi.org/10.1007/s11746-012-2108-9

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  • DOI: https://doi.org/10.1007/s11746-012-2108-9

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