Skip to main content
Log in

Lipase catalyzed production of monoacylglycerols by the esterification of fish oil fatty acids with glycerol

  • Published:
Biotechnology and Bioprocess Engineering Aims and scope Submit manuscript

Abstract

In this study, we attempted the efficient production of monoacylglycerols (MAG) via the lipase-catalyzed esterification of glycerol with fatty acids obtained from sardine oil. The reaction factors that influenced MAG synthesis were the glycerol to fatty acid mole ratio, amount of enzyme, organic solvent, temperature, and the type of lipase used. Porcine pancreas lipase was selected to catalyze this reaction. The optimum conditions we determined for MAG synthesis were a glycerol to fatty acid mole ratio of 1∶6, 100 mg/mL of lipase, and 30°C in dioxane. Under these conditions, the MAG content was 68% (w/w) after 72 h of reaction. The MAGs synthesized via the lipase-catalyzed esterification of glycerol with fatty acids included monomyristin, monopamiltin, and monoolein, as identified by GCMS.

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. Jackson, M. A. and J. W. King (1997) Lipase-catalyzed glycerolysis of soybean oil in supercritical carbon dioxide.J. Am. Oil Chem. Soc. 74: 103–106.

    Article  CAS  Google Scholar 

  2. Stevenson, D. E., R. A. Stanley, and R. H. Furneaux (1993) Glycerolysis of tallow with immobilized lipase.Biotechnol. Lett. 15: 1043–1048.

    Article  CAS  Google Scholar 

  3. Coteron, A., M. Martinez, and J. Aracil (1998) Reaction of olive oil and glycerol over immobilized lipasesJ. Am. Oil Chem. Soc. 75: 657–660.

    Article  CAS  Google Scholar 

  4. Sonntag, N. O. V. (1982) Glycerolysis of fats and methyl esters-status.J. Am. Oil Chem. Soc. 59: 795A-802A.

    Article  CAS  Google Scholar 

  5. Bornscheuer, U. T. (1995) Lipase-catalyzed synthesis of monoacylglycerols.Enzyme Microb. Technol. 17: 578–586.

    Article  CAS  Google Scholar 

  6. McNeill, G. P. and T. Yamane (1991) Further improvements in the yield of monoglycerols during enzymatic glycerolysis of fats and oils.J. Am. Oil Chem. Soc. 68: 6–10.

    Article  CAS  Google Scholar 

  7. Park, S. C., W. J. Chang, S. M. Lee, Y. J. Kim, and Y. M. Koo (2005) Lipase-catalyzed transensterification in several reaction systems: An application of room temperature ionic liquids for bi-phasic production ofn-butyl acetate.Biotechnol. Bioprocess Eng. 10: 99–102.

    Article  CAS  Google Scholar 

  8. Wu, J. C., H. R. Low, Y. Leng, Y. Chow, R. Li, M. Talukder, and W. J. Choi (2006) Ketoprofen resolution by enzymatic esterification and hydrolysis of the ester product.Biotechnol. Bioprocess Eng. 11: 211–214.

    Article  CAS  Google Scholar 

  9. Lee, D. H., J. M. Kim, H. Y. Shin, S. W. Kang, and S. W. Kim (2006) Biodiesel production using a mixture of immobilizedRhizopus oryzae andCandida rugosa lipases.Biotechnol. Bioprocess Eng. 11: 522–525.

    Article  CAS  Google Scholar 

  10. Watanabe, Y., Y. Yamauchi-Sato, T. Nagao, T. Yamamoto, K. Ogita, and Y. Shimada (2004) Production of monoacylglycerol of conjugated linoleic acid by esterification followed by dehydration at low temperature usingPenicillium camembertii lipase.J. Mol. Catal. B 27: 249–254.

    Article  CAS  Google Scholar 

  11. Bornscheuer, U. T. and T. Yamane (1994) Activity and stability of lipase in the solid-phase glycerolysis of triolein.Enzyme Microb. Technol. 16: 864–869.

    Article  CAS  Google Scholar 

  12. Hess, R., U. Bornscheuer, A. Capewell, and T. Scheper (1995) Lipase-catalyzed synthesis of monostearlylglycerol in organic solvents from 1,2-O-isopropylidene glycerol.Enzyme Microb. Technol. 17: 725–728.

    Article  CAS  Google Scholar 

  13. Janssen, A. E. M., A. Van der Padt, and K. Van't Riet (1993) Solvent effects on lipase-catalyzed esterification of glycerol and fatty acids.Biotechnol. Bioeng. 42: 953–962.

    Article  CAS  Google Scholar 

  14. Soumanou, M. M., U. T. Bornscheuer, and R. D. Schmid (1998) Two-step enzymatic reaction for the synthesis of pure structured triacyglycerides.J. Am. Oil Chem. Soc. 75: 703–710.

    Article  CAS  Google Scholar 

  15. Mukherjec, K. D. and I. Kiewitt (1996) Enrichment of very-long-chain mono-unsaturated fatty acids by lipasecatalysed hydrolysis and transesterification.Appl. Microbiol. Biotechnol. 44: 557–562.

    Article  Google Scholar 

  16. Matsuo, T., N. Sawamura, Y. Hashimoto, and W. Hashida (1980) Method for producing a cacao butter substitute.UK Patent GB 2035359 B.

  17. Godfrey, T. (1995) Lipases for industrial use.Lipid Technol. 7: 58–61.

    Google Scholar 

  18. Stamatis, H., A. Xenakis, M. Provelegiou, and F. N. Kolisis (1993) Esterification reactions catalyzed by lipases in microemulsions: The role of enzyme localization in relation to its selectivity.Biotechnol. Bioeng. 42: 103–110.

    Article  CAS  Google Scholar 

  19. Hamam, F. and F. Shahidi (2004) Synthesis of structured lipids via acidolysis of docosahexaenoic acid single cell oil (DHASCO) with capric acid.J. Agric. Food Chem. 52: 2900–2906.

    Article  CAS  Google Scholar 

  20. Soumanou, M. M., U. T. Bornscheuer, U. Schmid, and R. D. Schmid (1998) Synthesis of structured triglycerides by lipase catalysis.Fett. Lipid 100: 156–160.

    Article  CAS  Google Scholar 

  21. Esteban Cerdan, L., A. Robles Medina, A. Gimenez Gimenez, M. J. Ibanez Gonzalez, and E. Molina Grima (1998) Synthesis of polyunsaturated fatty acid-enriched triglycerides by lipase-catalyzed esterification.J. Am. Oil Chem. Soc. 75: 1329–1337.

    Article  Google Scholar 

  22. Halling, P. J. (1989) Lipase-catalyzed reactions in low water organic media: Effects of water activity and chemical modification.Biochem. Soc. Trans. 17: 1142–1145.

    CAS  Google Scholar 

  23. Cremonesi, P., G. Carrea, L. Ferrara, and E. Antonini (1974) Enzymatic dehydrogenenation of testosterone coupled to pyruvate reduction in a two-phase system.Eur. J. Biochem. 44: 401–405.

    Article  CAS  Google Scholar 

  24. Dordick, J. S. (1989) Enzymatic catalysis in monophasic organic-solvents.Enzyme Microb. Technol. 11: 194–211.

    Article  CAS  Google Scholar 

  25. Akoh, C. C. and K. H. Huang (1995) Enzymatic synthesis of structured lipids: Transesterification of triolein and caprylic acid.J. Food Lipids 2: 219–230.

    Article  CAS  Google Scholar 

  26. Yamane, T. (1987) Enzyme technology for the lipids industry: An engineering overview.J. Am. Oil Chem. Soc. 64: 1657–1662.

    Article  CAS  Google Scholar 

  27. Zaks, A. and A. M. Klibanov (1984) Enzymatic catalysis in organic media at 100°C.Science 224: 1249–1251.

    Article  CAS  Google Scholar 

  28. Shahani, K. M. (1975) Lipases and esterases. 2nd ed., pp. 182–221. In: G. Reed (ed.)Enzymes in Food Processing. Academic Press, New York, NY, USA.

    Google Scholar 

  29. Pinsirodom, P., Y. Watanabe, T. Nagao, A. Sugihara, T. Kobayashi, and Y. Shimada (2004) Critical temperature for production of MAG by esterification of different FA with glycerol usingPenicillium camembertii lipase.J. Am. Oil Chem. Soc. 81: 543–547.

    Article  CAS  Google Scholar 

  30. Robles Medina, A., L. Esteban Cerdan, A. Gimenez Gimenez, B. Camacho Paez, M. J. Ibanez Gonzalez, and E. Molina Grima (1999) Lipase-catalyzed esterification of glycerol and polyunsaturated fatty acids from fish and microalgae oils.J. Biotechnol. 70: 379–391.

    Article  CAS  Google Scholar 

  31. Chong, F. C., B. T. Tey, Z. M. Dom, K. H. Cheong, B. Satiawihardja, M. N. Ibrahim, R. A. Rahman, D. R. A. Biak, and T. C. Ling (2007) Rice bran lipase catalyzed esterification of palm oil fatty acid distillate and glycerol in organic solvent.Biotechnol. Bioprocess Eng. 12: 250–256.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Se-Kwon Kim.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Byun, HG., Eom, TK., Jung, WK. et al. Lipase catalyzed production of monoacylglycerols by the esterification of fish oil fatty acids with glycerol. Biotechnol. Bioprocess Eng. 12, 491–496 (2007). https://doi.org/10.1007/BF02931345

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02931345

Keywords

Navigation