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.
Similar content being viewed by others
References
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)
Akoh CC, Yee LN. Enzymatic synthesis of position specific lowcalorie structured lipids. J. Am. Oil Chem. Soc. 11: 1409–1413 (1997)
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)
Kim EJ, Yoon SH. Recent progress in enzymatic production of structured lipids. Food Sci. Biotechnol. 12: 721–726 (2003)
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)
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)
Hossen M, Hernandez E. Enzyme catalyzed synthesis of structured phospholipids with conjugated linoleic acid. Eur. J. Lipid Sci. Technol. 107: 730–736 (2005)
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)
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)
Zaks A, Klibanov AM. Enzyme-catalyzed processes in organic solvents. P. Natl. Acad. Sci. USA 82: 3192–3196 (1985)
Klibanov AM. Improving enzymes by using them in organic solvents. Nature 409: 241–246 (2001)
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)
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)
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)
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)
Noh S. Yoon SH. Stereospecific positional distribution of fatty acids of camellia (Camellia japonica L.) seed oil. J. Food Sci. 77: C1055–7 (2012)
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)
Haynes WM. CRC Handbook of Chemistry and Physics. 72nd ed. CRC Press, Boca Raton, FL, USA. p. 730 (1991)
Merck. The Merck Index. 11th ed. Merk Co., Whitehouse Station, NJ, USA. pp. 1086–1098 (1989)
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)
Laane C, Boeren S, Vos K, Veeger C. Rules for optimization of biocatalysts in organic solvents. Biotechnol. Bioeng. 30: 81–87 (1987)
Adlercreutz DH. Enzymatic synthesis of mixed acid phospholipids. PhD thesis, Lund University, Lund, Sweden (2002)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10068-014-0165-6