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Enhancement of both reaction yield and rate of synthesis of structured triacylglycerol containing eicosapentaenoic acid under vacuum with water activity control

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Lipids

Abstract

Production of structured triacylglycerols (sTAG) containing eicosapentaenoic acid (EPA) at the sn-1 (or 3) position using Lipozyme in a solvent-free system was studied. Optimal water activity (a w) for the synthesis of the sTAG was investigated. Vacuum was applied to shift reaction equilibrium toward the synthesis reaction by removing by-products. During vacuum application, the water level of the reaction system was controlled at the optimal level by addition of a suitable amount of water at a predetermined interval. Intermittent periodic addition of a suitable amount of water into the reaction mixture made the reaction rate faster than that without adding water. A molar yield of 89.7% of the targeted sTAG was obtained after 16 h reaction with a w control during the vacuum application as compared with the yield of 87.0% after 24 h of reaction without a w control during the vacuum application.

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Abbreviations

C8EE:

caprylic acid ethylester

DHA:

docosahexaenoic acid

EPA:

elcosapentaenoic acid

EPA-C8-C8:

1-eicosapentaenoyl-2,3-dicaprylin and/or 1,2-dicapryl-3-eicosapentaenoin

EPAEE:

EPA ethyl ester

MCFA:

medium-chain fatty acids

PUFA:

polyunsaturated fatty acids

sTAG:

structured triacylglycerols

TAG:

triacylglycerols

References

  1. Gill, I., and Valivety, R. (1997) Polyunsaturated Fatty Acids, Part 1: Occurrence, Biological Activities and Applications, TIBTECH 15, 401–408.

    CAS  Google Scholar 

  2. Jandacek, R.J., Whiteside, J.A., Holcombe, B.N., Volpenhein, R.A., and Taulbee, J.D. (1987) The Rapid Hydrolysis and Efficient Absorption of Triacylglycerols with Octanoic Acid in the 1 and 3 Positions and Long Chain Fatty Acid in the 2 Position, Am. J. Clin. Nutr. 45, 940–945.

    PubMed  CAS  Google Scholar 

  3. Akoh, C.C. (1995) Structured Lipids—Enzymatic Approach, INFORM 6, 1055–1061.

    Google Scholar 

  4. Lee, K.T., and Akoh, C.C. (1996) Immobilized Lipase-Catalyzed Production of Structured Lipids with Eicosapentaenoic Acid at Specific Positions, J. Am. Oil Chem. Soc. 73, 611–615.

    CAS  Google Scholar 

  5. Soumanou, M.M., Bornscheuer, U.T., Menge, U., and Schmid, R.D. (1997) Synthesis of Structured Triglycerides from Peanut Oil with Immobilized Lipase, J. Am. Oil Chem. Soc. 74, 427–433.

    CAS  Google Scholar 

  6. Hamosh, M., and Hamosh, P. (1996) Specificity of Lipases: Developmental Physiology Aspects—The Role of Lipase Selectivity in the Digestion of Milk Fat, in Enzyme Engineering of/with Lipases (Malcata, F.X., ed.) pp. 31–49, Kluwer Academic Publishers, Dordrecht.

    Google Scholar 

  7. Iverson, S.J., Kirk, C.L., Harmosh, M., and Newsome, J. (1991) Milk Lipid Digestion in the Neonatal Dog: The Combined Actions of Gastric and Bile Salt Stimulated Lipases, Biochim. Biophys. Acta 1083, 109–119.

    PubMed  CAS  Google Scholar 

  8. Christensen, M.S., Høy, C.-E., Becker, C.C., and Redgrave, T.G. (1995) Intestinal Absorption and Lymphatic Transport of Eicosapentaenoic (EPA), Docosahexaenoic (DHA), and Decanoic Acids: Dependence on Intramolecular Triacylglycerol Structure, Am. J. Clin. Nutr. 61, 56–61.

    PubMed  CAS  Google Scholar 

  9. Innis, S.M. (1992) n−3 Fatty Acid Requirements of the Newborn, Lipids 27, 879–885.

    PubMed  CAS  Google Scholar 

  10. Iverson, S., Sampugna, J.J., and Oftedal, O.T. (1992) Positional Specificity of Gastric Hydrolysis of Long Chain n−3 Polyunsaturated Fatty Acids of Seal Milk Triglycerides, Lipids 27, 870–878.

    PubMed  CAS  Google Scholar 

  11. Tanaka, Y., Fukuda, T., Hirano, J., and Hashizume, R. (1993) Triglyceride Specificity of Candida cylindracea Lipase: Effect of Docosahexaenoic Acid on Resistance of Triglyceride to Lipase. J. Am. Oil Chem. Soc. 70, 1031–1034.

    CAS  Google Scholar 

  12. Han, J.J., Iwasaki, Y., and Yamane, T. (1999) Monitoring of Lipase-Catalyzed Transesterification Between Eicosapentaenoic Acid Ethyl Ester and Tricaprylin by Silver Ion High-Performance Liquid Chromatography and High-Temperature Gas Chromatography, J. Am. Oil Chem. Soc. 76, 31–39.

    CAS  Google Scholar 

  13. Han, J.J., Iwasaki, Y., and Yamane, T. (1999) Use of Isopropanol as a Modifier in a Hexane-Acetonitrile Based Mobile Phase for the Separation of Positional Isomers of Triacylglycerols Containing Long Chain Polyunsaturated Fatty Acids in Silver Ion HPLC Method, J. High Resolut. Chromatogr. 22, 357–361.

    Article  CAS  Google Scholar 

  14. Yamane, T. (1988) Importance of Moisture Content Control for Enzymatic Reactions in Organic Solvents: A Novel Concept of “Microaqueous”, Biocatalysis 2, 1–9.

    CAS  Google Scholar 

  15. Zaks, A., and Klibanov, A. (1988) The Effect of Water on Enzyme Action in Organic Media, J. Biol. Chem. 263, 8017–8021.

    PubMed  CAS  Google Scholar 

  16. Goldberg, M., Thomas, D., Legoy, M.D. (1990) Water Activity as a Key Parameter of Synthesis Reactions: The Example of Lipase in Biphasic (liquid/solid) Media, Enzyme Microb. Technol 12, 976–981.

    Article  PubMed  CAS  Google Scholar 

  17. Han, J.J., and Rhee, J.S. (1998) Effect of Salt Hydrate Pairs for Water Activity Control on Lipase-Catalyzed Synthesis of Lysophospholipids in a Solvent Free System, Enzyme Microb. Technol. 22, 158–164.

    Article  CAS  Google Scholar 

  18. Kwon, S.J., and Rhee, J.S. (1998) On-Off Dewatering Control for Lipase-Catalyzed Synthesis of n-Butyl Oleate in n-Hexane by Tubular Type Pervaporation System, J. Microbiol. Biotechnol. 8, 165–170.

    Article  CAS  Google Scholar 

  19. Mensah, P., Gainer, J.L., and Carta, G. (1998) Adsorptive Control of Water in Esterification with Immobilized Enzymes: I. Batch Reactor Behavior. Biotechnol. Bioeng. 60, 434–444.

    Article  PubMed  CAS  Google Scholar 

  20. Clapes, P., Valencia, G., and Adlercreutz, P. (1992) Influence of Solvent and Water Activity on Kinetically Controlled Peptide Synthesis, Enzyme Microb. Technol. 14, 575–580.

    Article  PubMed  CAS  Google Scholar 

  21. Kvittinggen, L., Sjursnes, B., Anthonsen, T., and Halling, P.J. (1992) Use of Salt Hydrates to Buffer Optimal Water Level During Lipase-Catalyzed Synthesis in Organic Media: A Practical Procedure for Organic Chemists, Tetrahedron 48, 2793–2802.

    Article  Google Scholar 

  22. Halling, P.J. (1994) Thermodynamic Predictions for Biocatalysis in Nonconventional Media: Theory, Tests, and Recommendations for Experimental Design and Analysis, Enzyme Microb. Technol. 16, 178–206.

    Article  PubMed  CAS  Google Scholar 

  23. Valivety, R.H., Halling, P.J., and Macrae, A.R. (1992) Reaction Rate with Suspended Lipase Catalyst Shows Similar Dependence on Water Activity in Different Organic Solvents, Biochim. Biophys. Acta 1118, 218–222.

    PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Molecular Biotechnology, Department of Biological Mechanisms and Functions, Graduate School of Bio- and Agro-Sciences, Nagoya University, 464-8601, Nagoya, Japan

    Jeong Jun Han & Tsuneo Yamane

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  1. Jeong Jun Han
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  2. Tsuneo Yamane
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Correspondence to Tsuneo Yamane.

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Han, J.J., Yamane, T. Enhancement of both reaction yield and rate of synthesis of structured triacylglycerol containing eicosapentaenoic acid under vacuum with water activity control. Lipids 34, 989–995 (1999). https://doi.org/10.1007/s11745-999-0449-6

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  • DOI: https://doi.org/10.1007/s11745-999-0449-6

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