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Chemoenzymatic Method for Producing Stearidonic Acid Concentrates from Stearidonic Acid Soybean Oil

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Journal of the American Oil Chemists' Society

Abstract

The aim of this study was to produce stearidonic acid (SDA, 18:4n-3) omega-3 concentrates from 25 % SDA soybean oil (SDASO) by enzymatic acidolysis. Substrates were prepared by chemical and enzymatic hydrolysis of SDASO. A 62 % SDA free fatty acid mixture (SDA-FFA) was obtained by low temperature crystallization of the chemical hydrolyzate while partial hydrolysis of SDASO by non-immobilized lipase AY 30 (Candida rugosa) yielded a 51 % SDA acylglycerol mixture (SDA-GLY). Reaction conditions for acidolysis between SDA-FFA and SDA-GLY were optimized using response surface methodology (RSM). Incorporation of SDA into SDA-GLY by immobilized Lipozyme RM IM (Rhizomucor miehei) and non-immobilized Lipomod 34P-LO34P (C. cylindracea [rugosa]) lipases were modeled under varying levels of the substrate molar ratio (S r ), temperature (T), and time (t). Optimal conditions for production of a 60 % SDA concentrate were predicted to be S r  = 4.8, T = 65 °C and t = 8 h for Lipozyme RM IM and S r  = 5.0, T = 43 °C and t = 48 h for Lipomod 34P-L034P. The model was verified experimentally by gram scale synthesis under optimal conditions which resulted in the production of 59.98 and 58.98 % SDA concentrates (≥96 % triacylglycerols) by Lipozyme RM IM and Lipomod 34P-L034P, respectively.

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References

  1. Lavie CJ, Milani RV, Mehra MR, Ventura HO (2009) Omega-3 polyunsaturated fatty acids and cardiovascular diseases. J Am Coll Cardiol 54:585–594

    Article  CAS  Google Scholar 

  2. Makrides M, Neumann M, Simmer K, Pater J, Gibson R (1995) Are long-chain polyunsaturated fatty acids essential nutrients in infancy. Lancet 345:1463–1468

    Article  CAS  Google Scholar 

  3. Farquharson J, Jamieson EC, Abbasi KA, Patrick WJ, Logan RW, Cockburn F (1995) Effect of diet on the fatty acid composition of the major phospholipids of infant cerebral cortex. Arch Disease Childhood 72:198–203

    Article  CAS  Google Scholar 

  4. Harris WS (2007) Omega-3 Fatty acids and cardiovascular disease: a case for omega-3 index as a new risk factor. Pharmacol Res 55:217–223

    Article  CAS  Google Scholar 

  5. Gerster H (1998) Can adults adequately convert alpha-linolenic acid(18:3n–3) to eicosapentaenoic acid (20:5n–3) and docosahexaenoic acid (22:6n–3)? Int J Vitam Nutr Res 68:159–173

    CAS  Google Scholar 

  6. Naylor RL, Goldburg RJ, Prlmavera JH, Kautsky N, Beveldge MCM, Clay J, Follae C, Lubchenco J, Mooney H, Troell M (2000) Effect of aquaculture on world fish supplies. Nature 405:1017–1024

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  8. Froman B, Duong C, Listello J (2011) Soybean plant corresponding to transgenic event MON87769 and methods for detection thereof. US Patent 12,865,844

  9. Brenna JT (2002) Efficiency of conversion of α-linolenic acid to long chain n-3 fatty acids in man. Curr Opin Clin Nutr Metab Care 5:127–132

    Article  CAS  Google Scholar 

  10. James MJ, Ursin VM, Cleland LG (2003) Metabolism of stearidonic acid in human subjects: comparison with the metabolic of other n-3 fatty acids. Am J Clin Nutr 77:1140–1145

    CAS  Google Scholar 

  11. Monsanto Company Omega-3 enriched soybean oil: an effective means of enriching the body with heart-healthy stearidonic acid. http://www.monsanto.com/SiteCollectionDocuments/sda-omega3-index-study.pdf. Accessed Oct 2012

  12. Nutraingredients-USA Retail omega-3 s sales to hit $34.7 billion in 2016, report predicts. http://www.nutraingredients-usa.com/Product-Categories/Nutritional-lipids-and-oils/Retail-omega-3s-sales-to-hit-34.7-billion-in-2016-report-predicts. Accessed Oct. 2012

  13. Shahidi F, Wanasundara UN (1998) Omega-3 fatty acid concentrates: nutritional aspects and production technologies. Trends Food Sci Tech 9:230–240

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Kleiner L, Vazquez L, Akoh CC (2012) Increasing stearidonic acid (SDA) in modified soybean oil by lipase mediated acidolysis. J Am Oil Chem Soc 89:1267–1275

    Article  CAS  Google Scholar 

  17. Kleiner L, Vazquez L, Akoh CC (2012) Lipase-catalyzed concentration of stearidonic acid in modified soybean oil by partial hydrolysis. J Am Oil Chem Soc 89:1999–2010

    Article  CAS  Google Scholar 

  18. Pinsirodom P, Parkin KL (2001) In lipase assays. In: Wrolstad RE, Acree TE, Decker EA, Penner MH, Reid DS, Schwartz SJ, Shoemaker CF, Smith DM, Sporns P (eds) Current protocols in food analytical chemistry. Wiley, USA, pp C3.1.1–C3.1.13

    Google Scholar 

  19. Official methods and recommended practices of the American Oil Chemists’ Society (2009), 6th edn. AOCS, Champaign

  20. 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 

  21. AOAC International (1998) Official methods of analysis of AOAC International, 17th edn. Method 996.01, Gaithersburg

  22. Ichihara K, Fukubayashi Y (2010) Preparation of fatty acid methyl esters for gas–liquid chromatography. J Lipid Res 51:635–640

    Article  CAS  Google Scholar 

  23. McNeill GP, Ackman RG, Moore SR (1996) Lipase-catalyzed enrichment of long-chain polyunsaturated fatty acids. J Am Oil Chem Soc 73:1403–1407

    Article  CAS  Google Scholar 

  24. 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 

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

    Article  CAS  Google Scholar 

  26. Bottino NR, Vandenburg GA, Reiser R (1967) Resistance of certain long-chain polyunsaturated fatty acids of marine oils to pancreatic lipase hydrolysis. Lipids 2:489–493

    Article  CAS  Google Scholar 

  27. Jachmanian I, Schulte E, Mukherjee KD (1996) Substrate selectivity in esterification of less common fatty acids catalyzed by lipases from different sources. Appl Micro Biotech 44:563–567

    Article  CAS  Google Scholar 

  28. Lie O, Lambertsen G (1985) Digestive lipolytic enzymes in cod (Gadus morhua): fatty acid specificity. Comp Biochem Physiol 80:447–450

    Google Scholar 

  29. Mistry BS, Min DB (1988) Prooxidant effects of monoglycerides and diglycerides in soybean oil. J Food Sci 53:1896–1897

    Article  CAS  Google Scholar 

  30. Tischer W, Wedekind F (1999) Immobilized enzymes: methods and applications. Topics Curr Chem 200:95–126

    Article  CAS  Google Scholar 

Download references

Acknowledgments

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

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Correspondence to Casimir C. Akoh.

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Ifeduba, E.A., Akoh, C.C. Chemoenzymatic Method for Producing Stearidonic Acid Concentrates from Stearidonic Acid Soybean Oil. J Am Oil Chem Soc 90, 1011–1022 (2013). https://doi.org/10.1007/s11746-013-2251-y

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  • DOI: https://doi.org/10.1007/s11746-013-2251-y

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