Skip to main content
Log in

Effects of organic solvents on transesterification of phospholipids using phospholipase A2 and lipase

  • Research Article
  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

The transesterification abilities of phospholipase A2 and Mucor javanicus lipase in various organic solvents were studied. Phosphatidylcholine and caprylic acid (molar ratio, 1:6) were transesterified by incubation at 40°C in three organic solvents using phospholipase A2 and M. javanicus lipase. The fatty acid composition of the reaction product was measured using gas chromatography. Caprylic acid was incorporated into the sn-1 and -2 positions at a rate of 87.7% using phospholipase A2 in hexane, and 36.7% using M. javanicus lipase in diethyl ether. Higher acyl migration into sn-2 was observed in diethyl ether than in hexane during transesterification using M. javanicus lipase, however, there was no substantial difference in the caprylic acid content at the sn-2 position. Acyl migration during transesterification in methanol was lower than in other organic solvents. Non-polar hexane and diethyl ether were more effective for transesterification than methanol.

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. Yang TH, Han JJ, Rhee JS. Enzymatic synthesis of low-calorie structured lipid in a solvent free system. J. Am. Oil Chem. Soc. 78: 291–296 (2001)

    Article  CAS  Google Scholar 

  2. Akoh CC, Yee LN. Enzymatic synthesis of position specific lowcalorie structured lipids. J. Am. Oil Chem. Soc. 11: 1409–1413 (1997)

    Article  Google Scholar 

  3. Kim IH, Kim H, Lee KT, Chung SH, Ko SN. Lipase-catalyzed acidolysis of perilla oil with caprylic acid to produce structured lipids. J. Am. Oil Chem. Soc. 79: 363–367 (2002)

    Article  CAS  Google Scholar 

  4. Kim EJ, Yoon SH. Recent progress in enzymatic production of structured lipids. Food Sci. Biotechnol. 12: 721–726 (2003)

    CAS  Google Scholar 

  5. Aura AM, Forssell P, Mustranta A, Poutanen K. Transesterification of soy lecithin by lipase and phospholipase. J. Am. Oil Chem. Soc. 72: 1375–1379 (1995)

    Article  CAS  Google Scholar 

  6. Peng L, Xu X, Mu H, Hoy CE, Nissen JA. Production of structured phospholipids by lipase catalyzed acidolysis: optimization using response surface methodology. Enzym. Microb. Tech. 31: 523–532 (2002)

    Article  CAS  Google Scholar 

  7. Hossen M, Hernandez E. Enzyme catalyzed synthesis of structured phospholipids with conjugated linoleic acid. Eur. J. Lipid Sci. Technol. 107: 730–736 (2005)

    Article  CAS  Google Scholar 

  8. Vikbjerg AF, Mu H, Xu X. Parameters affecting incorporation and by-product formation during the production of structured phospholipids by lipase-catalyzed acidolysis in solvent-free system. J. Mol. Catal. B Enzym. 36: 14–21 (2005)

    Article  CAS  Google Scholar 

  9. Hara F. Nakashima T, Fukuda H. Comparative study of commercially available lipase in hydrolysis reaction of phosphatidylcholine. J. Am. Oil Chem. Soc. 74: 1129–1132 (1997)

    Article  CAS  Google Scholar 

  10. Zaks A, Klibanov AM. Enzyme-catalyzed processes in organic solvents. P. Natl. Acad. Sci. USA 82: 3192–3196 (1985)

    Article  CAS  Google Scholar 

  11. Klibanov AM. Improving enzymes by using them in organic solvents. Nature 409: 241–246 (2001)

    Article  CAS  Google Scholar 

  12. Peng L. Xu X, Mu H, Hoy CE, Nissen JA. Production of structured phospholipid by lipase catalyzed acidolysis: optimization using response surface methodology. Enzym. Microb. Tech. 31: 523–532 (2002)

    Article  CAS  Google Scholar 

  13. Reddy JRC, Vijeeta T, Karuna MSL, Rao BVSK, Prasad RBN. Lipase catalyzed preparation of palmitic and stearic acid rich phosphatidylcholine. J. Am. Oil Chem. Soc. 82: 727–730 (2005)

    Article  CAS  Google Scholar 

  14. Adlercreutz D, Budde H, Wehtje E. Synthesis of phosphatidylcholine with defined fatty acid in sn-1 position by lipase-catalyzed esterification and transesterification reaction. Biotechnol. Bioeng. 78: 403–411 (2002)

    Article  CAS  Google Scholar 

  15. Vikbjerg AF, Mu H, Xu X. Elucidation of acyl migration during lipase-catalyzed production of structured phospholipids. J. Am. Oil Chem. Soc. 83: 609–614 (2006)

    Article  CAS  Google Scholar 

  16. Noh S. Yoon SH. Stereospecific positional distribution of fatty acids of camellia (Camellia japonica L.) seed oil. J. Food Sci. 77: C1055–7 (2012)

    Article  CAS  Google Scholar 

  17. Lai OM, Ghazzli HM, Chong CL. Effect enzymatic transesterification on the melting points of palm stearin sunflower oil mixtures. J. Am. Oil Chem. Soc. 75: 881–886 (1998)

    Article  CAS  Google Scholar 

  18. Haynes WM. CRC Handbook of Chemistry and Physics. 72nd ed. CRC Press, Boca Raton, FL, USA. p. 730 (1991)

    Google Scholar 

  19. Merck. The Merck Index. 11th ed. Merk Co., Whitehouse Station, NJ, USA. pp. 1086–1098 (1989)

    Google Scholar 

  20. Li ZY, Ward OP. 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 

  21. Laane C, Boeren S, Vos K, Veeger C. Rules for optimization of biocatalysts in organic solvents. Biotechnol. Bioeng. 30: 81–87 (1987)

    Article  CAS  Google Scholar 

  22. Adlercreutz DH. Enzymatic synthesis of mixed acid phospholipids. PhD thesis, Lund University, Lund, Sweden (2002)

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Suk Hoo Yoon.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kim, J.H., Yoon, S.H. Effects of organic solvents on transesterification of phospholipids using phospholipase A2 and lipase. Food Sci Biotechnol 23, 1207–1211 (2014). https://doi.org/10.1007/s10068-014-0165-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-014-0165-6

Keywords

Navigation