Abstract
The transesterification of soybean lecithin with methyl esters of EPA and DHA in an organic solvent (hexane) using various commercially available lipases was studied. Lipases produced by Candida antarctica, Pseudomonas fluorescens, Burkholderia cepacia, Mucor miehei, Thermomyces lanuginosus and Rhizomucor miehei were compared, in the absence or presence of histidine, arginine, urea, Ca2+, Mg2+, or a combination of urea and divalent cations (additives at 5 % of the total lipid mass). Transesterification using the R. miehei enzyme reached 11.32 and 12.30 % in the presence of Ca2+ or Mg2+ respectively, and 8.58 and 9.31 % when urea was also added. These were the greatest degrees of transesterification obtained. The results suggest the potential use of this immobilized lipase as a catalyst for interesterification reactions in organic solvent systems with low water content.
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References
Akoh CC, Lee KT, Fomuso LB (1998) Synthesis of positional isomers of structured lipids with lipases as biocatalyst. In: Christophe AB (ed) Structural modified food fats: synthesis, biochemistry, and use. AOCS Press, Champaign, IL, pp 46–72
Arpigny JL, Jaeger KE (1999) Bacterial lipolytic enzymes: classification and properties. Biochemistry 343:177–183
Bruheim I, Hallaraker H, Griinari M, Fuglseth E, Saebo PC (2006) Enzymatically synthesized marine phospholipids. US Patent Application Publication. 2006, US 2006/0177486 A1
Chakraborty K, Vijayagopal P, Chakraborty RD, Vijayan KK (2010) Preparation of eicosapentaenoic acid concentrates from sardine oil by Bacillus circulans lipase. Food Chem 120:433–442
Chojnacka A, Gładkowski W, Kiełbowicz G, Wawrzeńczyk C (2009) Enzymatic enrichment of egg-yolk phosphatidylcholine with alpha-linolenic acid. Biotechnol Lett 31:705–709
Christie WW (2003) Analysis of conjugated linoleic acid: an overview. Adv Conj Linoleic Acid Res 2:1–12
Galli C, Sirtori CR, Mosconi C, Medini L, Gianfranceschi G, Vaccarino V, Scolastico C (1992) Prolonged retention of doubly labeled phosphatidylcholine in human plasma and erythrocytes after oral administration. Lipids 27:1005–1012
Ghazali HM, Hamidah S, Che Man YBJ (1995) Enzymatic transesterification of palm olein with nonspecific and 1,3-specific lipases. JAOCS 72:633–639
Gilbert EJ, Cornish A, Jones CW (1991) Purification and properties of extracellular lipase from Pseudomonas aeruginosa EF2. J Gen Microbiol 137:2223–2229
Guo Z, Vikbjerg AF, Xu X (2005) Enzymatic modification of phospholipids for functional applications and human nutrition. Biotech Adv 23:203–259
Gupta R, Gupta N, Rathi P (2004) Bacterial lipases: an overview of production, purification and biochemical properties. Appl Microbiol Biotechnol 64:763–781
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
Haraldsson GG (1999) The application of lipase for preparing various lipids enriched with omega-3 fatty acids. Rit Fiskideildar 16:97–105
Haraldsson GG, Thorarensen A (1999) Preparation of phospholipids highly enriched with n-3 polyunsaturated fatty acids by lipase. JAOCS 76:1143–1149
Haraldsson GG, Kristinsson B, Sigurdardottir R, Gudmundsson GG, Breivik H (1997) The preparation of concentrates of eicosapentaenoic acid and docosahexaenoic acid by lipase-catalyzed transesterification of fish oil with ethanol. JAOCS 74:1419–1423
Hernández JA, Aguilar AB, Portillo B, López-Gómez E, Beneyto JM, Gárcia-Legaz MF (2003) The effect of calcium on the antioxidant enzymes from salt-treated loquat and anger plants. Funct Plant Biol 30:1127–1137
Hibbeln JR, Nieminen LR, Blasbalg TL, Riggs J (2006) Healthy intakes of n-3 and n-6 fatty acids: estimations considering worldwide diversity. Am J Clin Nutr 83:1483–1493
Hita E, Robles A, Camacho B, González PA, Esteban L, Jiménez MJ, Munío MM, Molina E (2009) Production of structured triacylglycerols by acidolysis catalyzed by lipases immobilized in a packed bed reactor. Biochem Eng J 46:257–264
Kidd PM (2007) Omega-3 DHA and EPA for cognition, behavior, and mood: clinical findings and structural-functional synergies with cell membrane phospholipids. Altern Med Rev 12:207–227
Kim H, Choi H, Kim M, Sohn C, Oh T (2002) Expression and characterization of Ca2+ independent lipase from Bacillus pumilus B26. Biochim Biophys Acta 1583:205–212
Kim IH, Garcia HS, Hill CG Jr (2007) Phospholipase A1-catalyzed synthesis of phospholipids enriched in n-3 polyunsaturated fatty acid residues. Enz Microb Technol 40:1130–1135
Kris-Etherton PM, Harris WS, Appel LJ (2002) Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation 106:2747–2757
Lesuisse E, Schanck K, Colson C (1993) Purification and preliminary characterization of the extracellular lipase of Bacillus subtilis 168, an extremely basic pH-tolerant enzyme. Eur J Biochem 216:155–160
Lyberg AM, Adlercreutz P (2008) Lipase specificity towards eicosapentaenoic acid and docosahexaenoic acid depends on substrate structure. Bioch Biophys Acta 1784:343–350
Lyberg AM, Adlercreutz D, Adlercreutz P (2005) Enzymatic and chemical synthesis of phosphatidylcholine regioisomers containing eicosapentaenoic acid or docosahexaenoic acid. Eur J Lipid Sci Technol 107:279–290
Mutua LN, Akoh CC (1993) Lipase-catalyzed modification of phospholipids: incorporation of n-3 fatty acids into biosurfactants. JAOCS 70:125–128
Na A, Eriksson C, Eriksson SG, österber E, Holmberg K (1990) Synthesis of phosphatidylcholine with (n-3) fatty acids by phospholipase A2 in microemulsion. JAOCS 67:766–770
Nelson LA, Foglia A, Marman WN (1996) Lipase-catalyzed production of biodiesel. JAOCS 73:1191–1195
Osório NM, Dubreucq E, Manuela R, da Fonseca M, Ferreira-Dias S (2009) Lipase/acyltransferase-catalysed interesterification of fat blends containing n-3 polyunsaturated fatty acids. Eur J Lipid Sci Technol 111:120–134
Otero C, Lopez-Hernandez A, Garcia HS, Hernandez-Martın ECG, Hill CG Jr (2006) Continuous enzymatic transesterification of sesame oil and a fully hydrogenated fat: effects of reaction conditions on product characteristics. Biotechnol Bioeng 94:877–887
Peng L, Xu X, Mu H, Hby 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
Rodrigues RC, Fernandez-Lafuente R (2010) Lipase from Rhizomucor miehei as an industrial biocatalyst in chemical process. J Mol Catal B Enzym 64:18–22
Rodriguez-Fernandez C, Berasategui J, Villafafila A (1993) Role of bivalent cations on the catalytic properties of an extracellular lipase of Pseudomonas fluorescens. LWT Food Sci Technol 26:422–425
Rønne TH, Pedersen LS, Xu X (2005) Triglyceride selectivity of immobilized Thermomyces lanuginosa lipase in interesterification. JAOCS 82:737–743
Ruxton CHS, Reed SC, Simpson MJA, Millington KJ (2004) The health benefits of omega-3 polyunsaturated fatty acids: a review of the evidence. J Hum Nutr Dietet 17:449–459
Schuchardt JP, Schneider I, Meyer H, Neubronner J, von Schacky C, Hahn A (2011) Incorporation of EPA and DHA into plasma phospholipids in response to different omega-3 fatty acid formulations—a comparative bioavailability study of fish oil vs. krill oil. Lipids Health Dis 10:145
Snellman EA, Sullivan ER, Colwell RR (2002) Purification and properties of the extracellular lipase, Lip A, of Acinetobacter sp. RAG-1. Eur J Biochem 269:5771–5779
Snijder HJ, Dijkstra BW (2000) Bacterial phospholipase A: structure and function of an integral membrane phospholipase. Biochim Biophys Acta 1488:91–101
Softly BJ, Huang AS, Finley JW, Petersheim M, Yarger RG, Chrysam MM, Wieczorek RL, Otterburnm MS, Manz A, Templeman GJ (1994) Composition of representative SALATRIM fat preparations. J Agric Food Chem 42:461–467
Tanaka A, Sugimoto H, Muta Y, Mizuno T, Senoo K, Obata H (2003) Differential scanning calorimetry of the effects of Ca2+ on the thermal unfolding of Pseudomonas cepacia lipase. Biosci Biotechnol Biochem 67:207–210
Totani Y, Hara S (1991) Preparation of polyunsaturated phospholipids by lipase catalyzed transesterification. JAOCS 68:848–851
Van Oort MG, Deever AMTJ, Dijkman R, Tjeenk ML, Verheij HM, de Haas GH, Wenzig E, Gotz F (1989) Purification and substrate specificity of Staphylococcus hyicus lipase. Biochemistry 28:9278–9285
Vikbjerg AF, Mu H, Xu X (2005) Lipase-catalyzed acyl exchange of soybean phosphatidylcholine in n-hexane: a critical evaluation of both acyl incorporation and product recovery. Biotechnol Prog 21:397–404
Vikbjerg AF, Mu H, Xu X (2006) Elucidation of acyl migration during lipase-catalyzed production of structured phospholipids. JAOCS 83:607–614
Wang X (2000) Multiple forms of phospholipase D in plants: the gene family, catalytic and regulatory properties, and cellular functions. Prog Lipid Res 39:109–149
Xu X (2000) Production of specific-structured triacylglycerols by lipase-catalyzed reactions: a review. Eur J Lipid Sci Technol 102:287–303
Yang G, Song L, Li K, Hu C (2003) Studies on chemical constituents of polygonum orientale. Zhongguo Yao Za Zhi 38:338–340
Zainal Z, Yusoff MSA (1999) Enzymatic interesterification of palm stearin and palm Kernel olein. JAOCS 76:1003–1008
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Marsaoui, N., Laplante, S., Raies, A. et al. Incorporation of omega-3 polyunsaturated fatty acids into soybean lecithin: effect of amines and divalent cations on transesterification by lipases. World J Microbiol Biotechnol 29, 2233–2238 (2013). https://doi.org/10.1007/s11274-013-1388-z
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DOI: https://doi.org/10.1007/s11274-013-1388-z