Grasas y Aceites, Vol 65, No 4 (2014)

Lipase-catalyzed interesterification of egg-yolk phosphatidylcholine and plant oils


https://doi.org/10.3989/gya.0585141

A. Chojnacka
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Poland

W. Gładkowski
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Poland

G. Kiełbowicz
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Poland

A. Gliszczyńska
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Poland

N. Niezgoda
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Poland

C. Wawrzeńczyk
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Poland

Abstract


The incorporation of polyunsaturated fatty acids into the sn-1 position of egg-yolk phosphatidylcholine (PC) in the process of lipase-catalyzed interesterification was investigated. For this purpose plant oils containing these acids in the triacylglycerol (TAG) form were used as acyl donors and three commercially available immobilized lipases were examined as biocatalysts. In all the experiments the best results were obtained using Novozym 435. After 72 h of the reaction of PC with linseed oil the maximum incorporation of α-linolenic acid into PC was 34%. The result of this reaction was also a reduction in the n-6/n-3 ratio in egg-yolk PC from 24.5 to 0.7. The highest incorporation n-6 PUFAs into PC were obtained with evening primrose oil as the acyl donor, and in this case, 50.7% of n-6 PUFA as the sum of linoleic and γ-linolenic was achieved. The highest content of γ-linolenic acid in modified PC (7.3%) was achieved in the reaction of PC with borage oil.

Keywords


Egg-yolk phosphatidylcholine; Interesterification; Lipase; Plant oil; Polyunsaturated fatty acids; Structured phospholipids

Full Text:


HTML PDF XML

References


Adlercreutz D, Budde H, Wehtje E. 2002. Synthesis of phosphatidylcholine with defined fatty acid in the sn-1 position by lipase-catalyzed esterification and transesterification reaction. Biotechnol. Bioeng. 78, 403–411. http://dx.doi.org/10.1002/bit.10225 PMid:11948447

Akoh CC, Jennings BH, Lillard DA. 1995. Enzymatic modification of trilinolein: Incorporation of n-3 polyunsaturated fatty acids. J. Am. Oil Chem. Soc. 72, 1317–1321. http://dx.doi.org/10.1007/BF02546205

Anderson EM, Larsson KM, Kirk O. 1998. One Biocatalyst–Many Applications: The Use of Candida Antarctica B-Lipase in Organic Synthesis. Biocatal. Biotransform. 16, 181–204. http://dx.doi.org/10.3109/10242429809003198

Aymond WM, Van Elswyk ME. 1995. Yolk thiobarbituric acid reactive substances and n-3 fatty acids in response to whole and ground flaxseed. Poult. Sci. 74, 1388–1394. http://dx.doi.org/10.3382/ps.0741388 PMid:7479519

Baeza-Jiménez R, González-Rodríguez J, Kim I-H, García HS, Otero C. 2012. Use of immobilized phospholipase A1-catalyzed acidolysis for the production of structured phosphatidylcholine with an elevated conjugated linoleic acid content. Grasas Aceites 63, 44–52. http://dx.doi.org/10.3989/gya.045211

Berry EJ, Hirsch J. 1986. Does dietary linolenic acid influence blood pressure? Am. J. Clin. Nutr. 44, 336–340. PMid:2875645

Bigger JT, El-Sherif T. 2001. Polyunsaturated fatty acids and cardiovascular events. A fish tale. Circulation. 103, 623– 625. http://dx.doi.org/10.1161/01.CIR.103.5.623 PMid:11156869

Brockerhoff H, Yurkowski M. 1966. Stereospecific analyses of several vegetable fats. J Lipid Res. 7, 62–64. PMid:5900222

Chojnacka A, Gładkowski W, Kiełbowicz G, Wawrzenczyk C. 2009. Enzymatic enrichment of egg-yolk phosphatidylcholine with α-linolenic acid. Biotechnol. Lett. 31, 705–709. http://dx.doi.org/10.1007/s10529-009-9915-6 PMid:19165607

Christie WW, Nikolova-Damyanova B, Laakso P, Herslof B. 1991. Stereospecific analysis of triacyl-sn-glycerols via resolution of diastereomeric diacylglycerol derivatives by HPLC on silica. J. Am. Oil Chem. Soc. 68, 695–701. http://dx.doi.org/10.1007/BF02662155

Cobos A, de la Hoz L, Cambero MI, Ordó-ez JA. 1995. Dietary modification and hen strain dependence of egg yolk lipids. Food Res. Int. 28, 71–76. http://dx.doi.org/10.1016/0963-9969(95)93333-P

Dowhan W. 1997. Molecular basis for membrane phospholipid diversity: why are there so many phosholipids? Annu. Rev. Biochem. 66, 199–232. http://dx.doi.org/10.1146/annurev.biochem.66.1.199 PMid:9242906

Fernandez-Lafuente R. 2010. Lipase from Thermomyces lanuginosus: Uses and prospects as an industrial biocatalyst. J. Mol. Catal. B: Enzym. 62, 197–212. http://dx.doi.org/10.1016/j.molcatb.2009.11.010

Fomuso LB, Akoh CC. 1998. Structured lipids: Lipase-catalyzed interesterification of tricaproin and trilinolein. J. Am. Oil Chem. Soc. 75, 405–410. http://dx.doi.org/10.1007/s11746-998-0059-y

Fraeye I, Bruneel C, Lemahieu C, Buyse J, Muylaert K, Foubert I. 2012. Dietary enrichment of eggs with omega-3 fatty acids: A review. Food Res. Int. 48, 961–969. http://dx.doi.org/10.1016/j.foodres.2012.03.014

Gabizon A, Goren D, Horowitz AT, Tzemach D, Lossos A, Siegal T. 1997. Long-circulating liposomes for drug delivery in cancer therapy: a review of biodistribution in tumorbearing animals. Adv. Drug Deliv. Res. 24, 337–344. http://dx.doi.org/10.1016/S0169-409X(96)00476-0

Garcia HS, Kim I-H, Lopez-Hernandez A, Hill Jr. CG. 2008. Enrichment of lecithin with n-3 fatty acids by acidolysis using immobilized phospholipase A1. Grasas Aceites, 59, 368–374. http://dx.doi.org/10.3989/gya.2008.v59.i4.531

Ghosh M, Bhattacharyya DK. 1997. Soy lecithin – monoester interchange reaction by microbial lipase. J. Am. Oil Chem. Soc. 74, 761–763. http://dx.doi.org/10.1007/s11746-997-0215-9

Gładkowski W, Kiełbowicz G, Chojnacka A, Bobak Ł, Spychaj R, Dobrzan’ski Z, Trziszka T, Wawrzen’czyk C. 2014. The effect of feed supplementation with dietary sources of n-3 polyunsaturated fatty acids, flaxseed and algae Schizochytrium sp., on their incorporation into lipid fractions of Japanese quail eggs. Int. J. Food Sci. Tech. 49, 1876–1885. http://dx.doi.org/10.1111/ijfs.12497

Gładkowski W, Chojnacka A, Kiełbowicz G, Trziszka T, Wawrzenczyk C. 2012. Isolation of pure phospholipid fraction from egg-yolk. J. Am. Oil Chem. Soc. 89, 179–182. http://dx.doi.org/10.1007/s11746-011-1893-x

Gładkowski W, Kiełbowicz G, Chojnacka A, Gil M, Trziszka T, Dobrzan’ski Z, Wawrzen’czyk C. 2011. Fatty acid composition of egg yolk phospholipid fractions as the effect of feed supplementation of Lohmann Brown hens with humine-fat preparations. Food Chem. 126, 1013–1018. http://dx.doi.org/10.1016/j.foodchem.2010.11.112

Van Gool CJ, Zeegers MP, Thijs C. 2004. Epidemiology and health services research. Oral essential fatty acids supplementation in atopic dermatitis – a meta-analysis of placebo-controlled trials. Br. J. Dermatol. 150, 728–740. http://dx.doi.org/10.1111/j.0007-0963.2004.05851.x PMid:15099370

Gunstone FD. 1999. Enzymes as biocatalysts in the modification of natural lipids. J. Sci. Food Agric. 79, 1535–1549. http://dx.doi.org/10.1002/(SICI)1097-0010(199909)79:12<1535::AID-JSFA430>3.0.CO;2-7

Guo Z, Vikbjerg AF, Xu X. 2005. Enzymatic modification of phospholipids for functional applications and human nutrition. Biotechnol. Adv. 23, 203–259. http://dx.doi.org/10.1016/j.biotechadv.2005.02.001 PMid:15763405

Hara S, Hasuo H, Nakasat, M, Higaki Y, Totani Y. 2002. Modification of soybean phospholipids by enzymatic transacylation. J. Oleo Sci. 51, 417–422. http://dx.doi.org/10.5650/jos.51.417

Haraldsson GG, Thorarenson A. 1999. Preparation of phospholipids highly enriched with n-3 polyunsaturated fatty acids by lipase. J. Am. Oil. Chem. Soc. 76, 1143–1149. http://dx.doi.org/10.1007/s11746-999-0087-2

Holub DJ, Holub BJ. 2004. Omega-3 fatty acids from fish oils and cardiovascular disease. Mol. Cell. Biochem. 263, 217–225. http://dx.doi.org/10.1023/B:MCBI.0000041863.11248.8d PMid:15524182

Huge-Jensen B, Galluzzo DR, Jensen RG. 1987. Partial purification and characterization of free and immobilized lipases from Mucor miehei. Lipids, 22, 559–565. http://dx.doi.org/10.1007/BF02537281

Kiełbowicz G, Gładkowski W, Chojnacka A, Wawrzenczyk C. 2012. A simple method for positional analysis of phosphatidylcholine. Food Chem. 135, 2542–2548. http://dx.doi.org/10.1016/j.foodchem.2012.07.005 PMid:22980840

Kim I-H, Garcia HS, Hill Jr. CG. 2010. Synthesis of Structured Phosphatidylcholine Containing n-3 PUFA Residues via Acidolysis Mediated by Immobilized Phospholipase A1. J. Am. Oil. Chem. Soc. 87, 1293–1299. http://dx.doi.org/10.1007/s11746-010-1609-7

Kim I-H, Garcia HS, Hill Jr. CG. 2007. Phospholipase A1-catalyzed synthesis of phospholipids enriched in n−3 polyunsaturated fatty acid residues. Enzyme Microb. Tech. 40, 1130–1135. http://dx.doi.org/10.1016/j.enzmictec.2006.08.018

Kris-Etherton PM, Hecker KD, Binkoski AE. 2004. Polyunsaturated fatty acids and cardiovascular health. Nutr. Rev. 62, 414–426. http://dx.doi.org/10.1111/j.1753-4887.2004.tb00013.x PMid:15622714

Lee K-T, Akoh CC. 1998. Solvent-free enzymatic synthesis of structured lipids from peanut oil and caprylic acid in a stirred tank batch reactor. J. Am. Oil. Chem. Soc. 75, 1533–1537. http://dx.doi.org/10.1007/s11746-998-0090-z

Lewis NM, Seburg S, Flanagan NL. 2000. Enriched eggs as a source of n-3 polyunsaturated fatty acids for humans. Poultr. Sc. 79, 971–974. http://dx.doi.org/10.1093/ps/79.7.971 PMid:10901195

Lyberg A-M, Adlercreutz D, Adlercreutz P. 2005 Enzymatic and chemical synthesis of phosphatidylcholine regioisomers containing eicosapentaenoic acid or docosahexaenoic acid. Eur. J Lipid Sci. Tech. 107, 279–290.

Muggli R. 2005. Systemic evening primrose oil improves the biophysical skin parameters of healthy adults. Int. J. Cosmetic Sci. 27, 243–249. http://dx.doi.org/10.1111/j.1467-2494.2005.00274.x PMid:18492193

Mutua LN, Akoh CC. 1993. Lipase–catalyzed modification of phospholipids: incorporation of n-3 fatty acids into biosurfactants. J. Am. Oil Chem. Soc. 70, 125–128. http://dx.doi.org/10.1007/BF02542613

Nagao K, Yanagita T. 2008. Bioactive lipids in metabolic syndrome. Prog. Lipid Res. 47, 127–146. http://dx.doi.org/10.1016/j.plipres.2007.12.002 PMid:18177744

Palacios LE, Wang T. 2005. Egg-yolk lipid fractionation and lecithin characterization. J. Am. Oil Chem. Soc. 82, 571–578. http://dx.doi.org/10.1007/s11746-005-1111-4

Park CW, Kwon SJ, Han JJ, Rhee JS. 2000. Transesterification of phosphatidylcholine with eicosapentaenoic acid ethyl ester using phospholipase A2 in organic solvent. Biotechnol. Lett. 22, 147–150. http://dx.doi.org/10.1023/A:1005626508891

Peng L, Xu X, Mu H, Høy C-E, Adler-Nissen J. 2002. Production of structured phospholipids by lipase-catalyzed acidolysis: optimization using response surface methodology. Enzyme Microb. Technol. 31, 523–532. http://dx.doi.org/10.1016/S0141-0229(02)00147-3

Rodrigues RC, Fernandez-Lafuente R. 2010. Lipase from Rhizomucor miehei as an industrial biocatalyst in chemical process. J. Mol. Catal. B: Enzym, 64, 1–22. http://dx.doi.org/10.1016/j.molcatb.2010.02.003

Simopoulos AP. 2002. The importance of the ratio of omega-6/omega-3 essential fatty acids. Biomed. Pharmacother. 56, 365–379. http://dx.doi.org/10.1016/S0753-3322(02)00253-6

Schneider M. 2001. Phospholipids for functional food. Eur. J. Lipid Sci. Tech. 104, 98–101. http://dx.doi.org/10.1002/1438-9312(200102)103:2<98::AID-EJLT98>3.0.CO;2-G

Uauy RMD, Dangour AD. 2006. Nutrition in Brain Development and Aging: Role of Essential Fatty Acids. Nutr. Rev. 64, 24–33. http://dx.doi.org/10.1301/nr.2006.may.S24-S33

Uppenberg J, Patkar S, Bergfors T, Jones TA. 1994. Crystallization and Preliminary X-ray Studies of Lipase B from Candida antarctica. J. Mol. Biol. 235, 790–792. http://dx.doi.org/10.1006/jmbi.1994.1035 PMid:8289302

Vessby B. 2003. Dietary fat, fatty acid composition in plasma and the metabolic syndrome. Curr. Opin. Lipidol. 14, 15–19. http://dx.doi.org/10.1097/00041433-200302000-00004 PMid:12544656

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 36, 14–21. http://dx.doi.org/10.1016/j.molcatb.2005.07.002

Virto C, Adlecreutz P. 2000. Lysophosphatidylcholine synthesis with Candida antarctica lipase B (Novozymes 435). Enzyme Microb. Tech. 26, 630–635. http://dx.doi.org/10.1016/S0141-0229(00)00147-2




Copyright (c) 2014 Consejo Superior de Investigaciones Científicas (CSIC)

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.


Contact us grasasyaceites@ig.csic.es

Technical support soporte.tecnico.revistas@csic.es