Journal of the American Oil Chemists' Society

, Volume 75, Issue 11, pp 1489–1494 | Cite as

Application of potato lipid acyl hydrolase for the synthesis of monoacylglycerols

  • Alasdair R. Macrae
  • Jean E. Visicchio
  • Alexandra Lanot
Article

Abstract

Protein extracts from potato tubers contain a lipid acyl hydrolase (LAH) with an unusual selectivity. The component responsible for the enzyme activity is a group of closely related glycoproteins, known as patatin. Potato LAH catalyzes the rapid hydrolysis of monoacylglycerols (MAG), but in contrast expresses only low activity with di- and triacylglycerols. The selectivity of the LAH can be exploited for the synthesis of MAG from fatty acids and glycerol in microaqueous reaction systems. Oleic, linoleic, linolenic, capric, lauric, and myristic acids can be used as reactants, and in each case the reaction products contain >95 mol% MAG and <5 mol% diacylglycerol. By removing water from the reaction mixture by distillation under vacuum, excellent conversions of fatty acids into MAG are possible. Low conversions are observed with palmitic and stearic acids, because of the necessity to use a high temperature (70°C) to maintain a liquid reaction mixture. Potato LAH is rapidly inactivated at 70°C in the microaqueous reaction systems. Potato LAH also catalyzes the selective synthesis of monoesters from oleic acid and simple diols. With oleic acid and diglycerol, monoesters are again the main reaction products, but 17 mol% diesters are also formed.

Key Words

Diglycerol diol fatty acid glycerol lipase lipid acyl hydrolase monoacylglycerol patatin potato 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Galliard, T., The Enzymic Deacylation of Phospholipids and Galactolipids in Plants: Purification and Properties of a Lipolytic Acyl Hydrolase from Potato Tubers, Biochem. J. 121:379–390 (1971).PubMedGoogle Scholar
  2. 2.
    Hirayama, O., H. Matsuda, H. Takeda, K. Maenaka, and H. Takatsuka, Purification and Properties of a Lipid Acyl Hydrolase from Potato Tubers, Biochim. Biophys. Acta 384:127–137 (1975).PubMedGoogle Scholar
  3. 3.
    Racusen, D., Lipid Acyl Hydrolase of Patatin, Can. J. Bot. 62:1640–1644 (1984).CrossRefGoogle Scholar
  4. 4.
    Andrews, D.L., B. Beames, M.D. Summers, and W.D. Park, Characterization of the Lipid Acyl Hydrolase Activity of the Major Potato (Solanum tuberosum) Tuber Protein, Patatin, by Cloning and Abundant Expression in a Baculovirus Vector, Biochem. J. 252:199–206 (1988).PubMedGoogle Scholar
  5. 5.
    Racusen, D., and M. Foote, A Major Soluble Glycoprotein of Potato Tubers, J. Food Biochem. 4:43–52 (1980).CrossRefGoogle Scholar
  6. 6.
    Racusen, D., Occurrence of Patatin During Growth and Storage of Potato Tubers, Can. J. Bot. 61:370–373 (1983).Google Scholar
  7. 7.
    Galliard, T., and S. Dennis, Phospholipase, Galactolipase and Acyl Transferase Activities of a Lipolytic Enzyme from Potato, Phytochemistry 13:1731–1735 (1974).CrossRefGoogle Scholar
  8. 8.
    Krog, N., Food Emulsifiers, in Lipid Technologies and Applications, edited by F.D. Gunstone and F.B. Padley, Marcel Dekker, New York, 1997, pp. 521–534.Google Scholar
  9. 9.
    Bornscheuer, U.T., Lipase Catalysed Synthesis of Monoacylglycerols, Enzyme Microb. Technol. 17:578–586 (1995).CrossRefGoogle Scholar
  10. 10.
    McNeill, G.P., S. Shimizu, and T. Yamani, High Yield Enzymatic Glycerolysis of Fats and Oils, J. Am. Oil Chem. Soc. 68:1–5 (1991).Google Scholar
  11. 11.
    McNeill, G.P., and T. Yamane, Further Improvements in the Yield of Monoglycerides During Enzymatic Glycerolysis of Fats and Oils, Ibid.:6–10 (1991).Google Scholar
  12. 12.
    Berger, M., and M.P. Schneider, Enzymatic Esterification of Glycerol II. Lipase Catalyzed Synthesis of Regioisomerically Pure 1(3)-rac-Monoacylglycerols, Ibid.:961–965 (1992).CrossRefGoogle Scholar
  13. 13.
    Bohac, J.R., A Modified Method to Purify Patatin from Potato Tubers, J. Agric. Food Chem. 39:1411–1415 (1991).CrossRefGoogle Scholar
  14. 14.
    Partington, J.C., and G.P. Bolwell, Purification of Polyphenol Oxidase Free of the Storage Protein Patatin from Potato Tuber, Phytochemistry 42:1499–1502 (1996).PubMedCrossRefGoogle Scholar
  15. 15.
    Stiekema, W.J., F. Heidekamp, W.G. Dirkse, J. van Beckum, P. de Haan, C. ten Bosch, and J.D. Louwerse, Molecular Cloning and Analysis of Four Potato Tuber mRNAs, Plant Mol. Biol. 11:255–269 (1988).CrossRefGoogle Scholar
  16. 16.
    Bosley, J., Turning Lipases into Industrial Biocatalysts, Biochem. Soc. Trans. 25:174–178 (1997).PubMedGoogle Scholar

Copyright information

© AOCS Press 1998

Authors and Affiliations

  • Alasdair R. Macrae
    • 1
  • Jean E. Visicchio
    • 1
  • Alexandra Lanot
    • 1
  1. 1.Unilever ResearchColworth LaboratorySharnbrookUnited Kingdom

Personalised recommendations