Skip to main content
Log in

Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study

  • Original Research Paper
  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

Non-enzymatic acyl migration could be counter-productive for the preparation of structured phospholipids with docosahexaenoic acid (DHA) at a designated position. Therefore enzymatic approaches have been developed to investigate acyl migration. First, acyl migration from sn-2 to sn-1 position has been set into relief by a three step enzymatic method using a typo-selective lipase, a phospholipase A2 and a non-selective lipase. The effect of reaction temperature on acyl migration from sn-2 to sn-1 was monitored: lowering the reaction temperature from 40 to 30°C allowed a reduction of DHA migration rate of 40%. Secondly, acyl migration from sn-1 to sn-2 position was negligible. This last result was obtained through the study of structured phosphatidylcholine selective deacylation using a phospholipase A2.

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.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Bligh EG, Dyer WJ (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37:911–917

    PubMed  CAS  Google Scholar 

  • Cansell M, Nacka F, Combe N (2003) Marine lipid-based liposomes increase in vivo FA bioavailability. Lipids 38:551–559

    Article  PubMed  CAS  Google Scholar 

  • Devos M, Poisson L, Ergan F et al (2006) Enzymatic hydrolysis of phospholipids from Isochrysis galbana for docosahexaenoic acid enrichment. Enzyme Microb Technol 39:548–554

    Article  CAS  Google Scholar 

  • Guo Z, Vikbjerg AF, Xu X (2005) Enzymatic modification of phospholipids for functional applications and human nutrition. Biotechnol Adv 23:203–259

    Article  PubMed  CAS  Google Scholar 

  • Halldorsson 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  CAS  Google Scholar 

  • Haraldsson GG, Kristinsson B (1998) Separation of eicosapentaenoic acid and docosahexaenoic acid in fish oil by kinetic resolution using lipase. J Am Oil Chem Soc 75:1551–1556

    Article  CAS  Google Scholar 

  • Haraldsson GG, Kristinsson B, Sigurdardottir R et al (1997) The preparation of concentrates of eicosapentaenoic acid and docosahexaenoic acid by lipase-catalyzed transesterification of fish oil with ethanol. J Am Oil Chem Soc 74:1419–1424

    Article  CAS  Google Scholar 

  • Morimoto T, Murakami N, Nagatsu A et al (1993) Regiospecific deacylation of glycerophospholipids by use of Mucor javanicus lipase. Tetrahedron Lett 34:2487–2490

    Article  CAS  Google Scholar 

  • Mu H, Kurvinen J-P, Kallio H et al (2001) Quantitation of acyl migration during lipase-catalyzed acidolysis, and of the regioisomers of structured triacylglycerols formed. J Am Oil Chem Soc 78:959–964

    Article  CAS  Google Scholar 

  • Peng L, Xu X, Mu H et al (2002) Production of structured phospholipids by lipase-catalyzed acidolysis: optimization using response surface methodology. Enzyme Microb Technol 31:523–532

    Article  CAS  Google Scholar 

  • Plückthun A, Dennis EA (1982) Acyl and phosphoryl migration in lysophospholipids: importance in phospholipid synthesis and phospholipase specificity. Biochemistry 21:1743–1750

    Article  PubMed  Google Scholar 

  • Poisson L, Ergan F (2001) Docosahexaenoic acid ethyl esters from Isochrysis galbana. J Biotechnol 91:75–81

    Article  PubMed  CAS  Google Scholar 

  • Slover HT, Lanza E (1979) Quantitative analysis of food fatty acids by capillary gas chromatography. J Am Oil Chem Soc 56:933–943

    Article  CAS  Google Scholar 

  • Tangkam K, Weber N, Wiege B (2008) Solvent-free lipase-catalyzed preparation of diglycerides from co-products of vegetable oil refining. Grasas y Aceites 59:245–253

    CAS  Google Scholar 

  • Vikbjerg AF, Mu H, Xu X (2005) 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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Vikbjerg AF, Mu H, Xu X (2007) Synthesis of structured phospholipids by immobilized phospholipase A2 catalyzed acidolysis. J Biotechnol 128:545–554

    Article  PubMed  CAS  Google Scholar 

  • Virto C, Svensson I, Adlercreutz P (1999) Enzymatic synthesis of lysophosphatidic acid and phosphatidic acid. Enzyme Microb Technol 24:651–658

    Article  CAS  Google Scholar 

  • Ward OP, Singh A (2005) Omega–3/6 fatty acids: alternative sources of production. Proc Biochem 40:3627–3652

    Article  CAS  Google Scholar 

  • Williams JP, Khan MU, Wong D (1995) A simple technique for the analysis of positional distribution of fatty acids on di- and triacylglycerols using lipase and phospholipase A2. J Lipid Res 36:1407–1412

    PubMed  CAS  Google Scholar 

  • Wongsakul S, Prasertsan P, Bornscheuer UT et al (2003) Synthesis of 2-monoglysis of palm oil and tuna oil using immobilized lipases. Eur J Lipid Sci Technol 105:68–73

    Article  CAS  Google Scholar 

  • Yang T, Fruekilde M-B, Xu X (2005) Suppression of acyl migration in enzymatic production of structured lipids through temperature programming. Food Chem 92:101–107

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by Laval Agglomération and the Conseil Général de la Mayenne (fellowships for M. Devos and S. Godet). The authors thank Pierre Goffi for his contribution to this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Laurent Poisson.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Poisson, L., Devos, M., Godet, S. et al. Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study. Biotechnol Lett 31, 743–749 (2009). https://doi.org/10.1007/s10529-009-9932-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10529-009-9932-5

Keywords

Navigation