Skip to main content
Log in

Synthesis of polyunsaturated fatty acid-enriched triglycerides by lipase-catalyzed esterification

  • Published:
Journal of the American Oil Chemists' Society

Abstract

This paper reports on the synthesis of triglycerides by enzymatic esterification of polyunsaturated fatty acids (PUFA) with glycerol. A PUFA concentrate obtained from cod liver oil was used to optimize the reaction to favor triglyceride synthesis with lipases. The type and amount of lipase and organic solvent, glycerol content, temperature, water content, and amount and time of addition of molecular sieves were studied. The optimal reaction mixture and conditions were: 9 mL hexane, 60°C, 0.5% (vol/vol) water, 1 g molecular sieves added after 24 h of reaction, glycerol/fatty acid molar ratio 1:3 and 100 mg of Novozym 435 (Novo Nordisk A/S) lipase. Under these conditions, an enriched triglyceride yiedl of 84.7% containing 27.4% eicosapentaenoic acid and 45.1% docosahexaenoic acid was obtained from a cod liver oil PUFA concentrate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Simopoulos, A.P., Omega-3 Fatty Acids in Health and Disease and in Growth and Development, Am. J. Clin. Nutr. 54:438–463 (1991).

    PubMed  CAS  Google Scholar 

  2. Nettleton, J.A., Are n-3 Fatty Acids Essential Nutrients for Fetal and Infant Development?, J. Am. Diet. Assoc. 93:58–64 (1993).

    Article  PubMed  CAS  Google Scholar 

  3. Innis, S.M., Essential Fatty Acids in Growth and Development, Prog. Lipid Res. 30:39–103 (1991).

    Article  PubMed  CAS  Google Scholar 

  4. Weylandt, K.H., J.X. Kang, and A. Leaf, Polyunsaturated Fatty Acids Exert Antiarrhythmic Actions as Free Acids Rather Than in Phospholipids, Lipids 31:977–982 (1996).

    Article  PubMed  CAS  Google Scholar 

  5. Wigmore, S.J., J.A. Ross, J.S. Falconer, C.E. Plester, M.J. Tisdade, D.C. Carter, and K.C.H. Faron, Effect of PUFA on the Progress of Cachexia in Patients with Pancreatic Cancer, Nutrition 12:27–30 (1996).

    Google Scholar 

  6. Hamazaki, T., S. Fischer, H. Schweer, C.O. Meese, M. Urakaze, A. Yokoyama, and S. Yano, The Infusion of Trieicosapentaenoyl-Glycerol into Humans and the in vivo Formation of Prostaglandin I3 and Tromboxane A3, Biochem. Biophys. Res. Commun. 151:1386–1394 (1988).

    Article  PubMed  CAS  Google Scholar 

  7. Li, Z.-Y., and O.P. Ward, Lipase-Catalyzed Esterification of Glycerol and n-3 Polyunsaturated Fatty Acid Concentrate in Organic Solvent, J. Am. Oil Chem. Soc. 70:745–748 (1993).

    Article  CAS  Google Scholar 

  8. Kosugi, Y., and N. Azuma, Synthesis of Triacylglycerol from Polyunsaturated Fatty Acid by Immobilized Lipase, Ibid.:1397–1403 (1994).

    Article  CAS  Google Scholar 

  9. Robles Medina, A., A. Giménez Giménez, F. García Camacho, J.A. Sánchez Pérez, E. Molina Grima, and A. Contreras Gómez, Concentration and Purification of Stearidonic, Eicosapentaenoic and Docosahexaenoic Acids from Cod Liver Oil and the Marine Microalga Isochrysis galbana, Ibid.:575–583 (1995).

    CAS  Google Scholar 

  10. Molina Grima, E., A. Robles Medina, A. Giménez Giménez, J.A. Sánchez Pérez, F. García Camacho, and J.L. García Sánchez, Comparison Between Extraction of Lipids and Fatty Acids from Microalgal Biomass, Ibid.:955–959 (1994).

    Article  CAS  Google Scholar 

  11. Cartens, M., E. Molina Grima, A. Robles Medina, A. Giménez Giménez, and M.J. Ibáñez González, Eicosapentaenoic Acid (EPA, 20:5n3) from the Microalga Phaeodactylum tricornutum, Ibid.:1025–1031 (1996).

    Article  CAS  Google Scholar 

  12. Molina Grima, E., A. Robles Medina, A. Giménez Giménez, and M.J. Ibáñez González, Gram-Scale Purification of Eicosapentaenoic Acid (EPA 20:5n-3) from Wet Phaeodactylum tricornutum UTEX 640 Biomass, J. Appl. Phycol. 8:359–367 (1996).

    Article  Google Scholar 

  13. Lepage, G., and C. Roy, Improved Recovery of Fatty Acid Through Direct Transesterification Without Prior Extraction or Purification, J. Lipid Res. 25:1391–1396 (1984).

    PubMed  CAS  Google Scholar 

  14. Dordick, J.S., Enzymatic Catalysis in Monophasic Organic Solvents, Enzyme Microb. Technol. 11:194–211 (1989).

    Article  CAS  Google Scholar 

  15. Castillo, E., V. Dossat, A. Marty, J.S. Condoret, and D. Combes, The Role of Silica Gel in Lipase-Catalyzed Esterification Reactions of High-Polar Substrates, J. Am. Oil Chem. Soc. 74:77–85 (1997).

    Article  CAS  Google Scholar 

  16. Ergan, F., M. Trani, and G. André, Production of Glycerides from Glycerol and Fatty Acid by Immobilized Lipases in Nonaqueous Media, Ibid.:195–200 (1990).

    CAS  Google Scholar 

  17. Ergan, F., M. Trani, and G. André, Solvent-Free Triglyceride Synthesis Using Lipozyme™ IM-20, Biotechnol. Lett. 10:629–634 (1988).

    Article  CAS  Google Scholar 

  18. Ergan, F., and M. Trani, Effect of Lipase Specificity on Triglyceride Synthesis, Ibid.:19–24 (1991).

    Article  CAS  Google Scholar 

  19. Greasham, R., and E. Inamine, Nutritional Improvement of Processes, in Manual of Industrial Microbiology and Biotechnology, edited by A.L. Demain and N.A. Solomon, American Society for Microbiology, Washington, DC, 1986, pp. 41–48.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

Cerdán, L.E., Medina, A.R., Giménez, A.G. et al. Synthesis of polyunsaturated fatty acid-enriched triglycerides by lipase-catalyzed esterification. J Amer Oil Chem Soc 75, 1329–1337 (1998). https://doi.org/10.1007/s11746-998-0180-y

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-998-0180-y

Key words

Navigation