Synthesis of 2-monoacylglycerols and structured triacylglycerols rich in polyunsaturated fatty acids by enzyme catalyzed reactions

Enzyme and Microbial Technology

Volumn 51, Issue 3, 2012, Pages 148-155

  Rodríguez, Alicia ^a   Esteban, Luis ^a   Martín, Lorena ^a   Jiménez, María José ^a   Hita, Estrella ^a   Castillo, Beatriz ^a   González, Pedro A ^a   Robles, Alfonso ^a  

^a UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

2 Monoacylglycerol; Alcoholysis; Esterification; Lipase; Stirred tank reactor (STR); Structured lipid

Indexed keywords

1-BUTANOL; 2-MONOACYLGLYCEROL; ABSOLUTE ETHANOL; ALCOHOLYSIS; ALCOHOLYSIS REACTIONS; ANTARTICA; CAPRYLIC ACID; COD LIVER OIL; ENZYME CATALYZED REACTION; LOW TOXICITY; NOVOZYM435; OPERATIONAL CONDITIONS; OPTIMAL CONDITIONS; RECOVERY YIELD; RHIZOPUS ORYZAE; STIRRED TANK REACTORS; STRUCTURED LIPIDS; STRUCTURED TRIACYLGLYCEROLS;

CATALYSIS; ESTERIFICATION; ESTERS; ETHANOL; GLYCEROL; HEXANE; LIPASES; OPTIMIZATION; POLYUNSATURATED FATTY ACIDS; PURIFICATION; SATURATED FATTY ACIDS; SOLVENT EXTRACTION;

ORGANIC SOLVENTS;

BUTANOL; COD LIVER OIL; DOCOSAHEXAENOIC ACID; HEXANE; POLYUNSATURATED FATTY ACID; TRIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE;

ALCOHOLYSIS; ARTICLE; CANDIDA; CATALYSIS; ENZYME MECHANISM; ESTERIFICATION; LIPID COMPOSITION; NONHUMAN; RHIZOPUS ORYZAE; SOLVENT EXTRACTION; SYNTHESIS;

BIOTECHNOLOGY; CANDIDA; CATALYSIS; COD LIVER OIL; ESTERIFICATION; ETHANOL; FATTY ACIDS, UNSATURATED; LIPASE; MONOGLYCERIDES; RHIZOPUS; TRIGLYCERIDES;

CANDIDA; RHIZOPUS ORYZAE;

EID: 84863083791     PISSN: 01410229     EISSN: 18790909     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2012.05.006     Document Type: Article

References (29)

1. Simopoulos A.P. Omega-3 fatty acids in health and disease and in growth and development. American Journal of Clinical Nutrition 1991, 54:438-463.
2. Nettleton J.A. Are n-3 fatty acids essential nutrients for fetal and infant development?. Journal of the American Dietetic Association 1993, 93:58-64.
3. Mu H., Porsgaard T. The metabolism of structured triacylglycerols. Progress in Lipid Research 2005, 44:430-448.
4. Xu X., Hoy C.-E.S., Balchen S., Adler-Nissen J. Specific-structured lipid: nutritional perspectives and production potentials. Proceedings of international symposium on the approach to functional cereals and oils 1997, 806-813. CCOA, Beijing.
5. Akoh C.C., Huang K.H. Enzymatic synthesis of structured lipids: transesterification of triolein and caprylic acid. Journal of Food Lipids 1995, 2:219-230.
6. Shimada Y., Sugihara A., Maruyama K., Nagao T., Nakayama S., Nakano H., et al. Production of structured lipids containing docosahexaenoic and caprylic acids using immobilized Rhizopus delemar lipase. Journal of Fermentation and Bioengineering 1996, 81:299-303.
7. Shimada Y., Suenaga M., Sugihara A., Nakai S., Tominaga Y. Continuous production of structured lipid containing γ-linolenic and caprylic acids by immobilised Rhizopus delemar lipase. Journal of the American Oil Chemists Society 1999, 76:189-193.
8. Xu X., Balchen S., Hoy C.-E., Adler-Nissen J. Pilot batch production of specific-structured triacylglycerols by lipase-catalyzed interesterification in a laboratory-scale continuous reactor. Journal of the American Oil Chemists Society 1998, 75:301-308.
9. Camacho Páez B., Robles Medina A., Camacho Rubio F., González Moreno P.A., Molina Grima E. Production of structured triglycerides rich in n-3 polyunsaturated fatty acids by the acidolysis of cod liver oil and caprylic acid in a packed-bed reactor: equilibrium and kinetics. Chemical Engineering Science 2002, 57:1237-1249.
10. Hita E., Robles A., Camacho B., Ramírez A., Esteban L., Jiménez M.J., et al. Production of structured triacylglycerols (STAG) rich in docosahexaenoic acid (DHA) in position 2 by acidolysis of tuna oil catalyzed by lipases. Process Biochemistry 2007, 42:415-422.
11. Schmid U., Bornscheuer U.T., Soumanou M.M., McNeil F.P., Schmid R.D. Optimization of the reaction conditions in the lipase-catalyzed synthesis of structured triglycerides. Journal of the American Oil Chemists Society 1998, 75:1527-1531.
12. Soumanou M.M., Bornscheuer U.T., Schmid R.D. Two-step enzymatic reaction for the synthesis of pure structured triacylglycerides. Journal of the American Oil Chemists Society 1998, 75:703-710.
13. Irimescu R., Furihata K., Hata Y., Iwasaki Y., Yamane T. Utilization of reaction medium-dependent regiospecificity of C. antarctica lipase (Novozym 435) for the synthesis of 1,3-dicapryloyl-2-docosahexanoyl (or eicosapentanoyl) glycerol. Journal of the American Oil Chemists Society 2001, 78:285-289.
14. Irimescu R., Furihata K., Hata Y., Iwasaki Y., Yamane T. Two-step enzymatic synthesis of docosahexaenoic acid-rich symmetrically structured triacylglycerols via 2-monoacylglycerols. Journal of the American Oil Chemists Society 2001, 78:743-748.
15. Millqvist Fureby A., Virton C., Adlercreutz P., Mattiasson B Acyl group migration in 2-monoolein. Biocatalysis and Biotransformation 1996, 14:89-111.
16. Watanabe Y., Shimada Y., Sugihara A., Tominaga Y. Stepwise ethanolysis of tuna oil using immobilized Candida antarctica lipase. Journal of Bioscience and Bioengineering 1999, 88:622-626.
17. Deng L., Xu X., Haraldsson G., Tan T., Wang F. Enzymatic production of alkyl esters through alcoholysis: a critical evaluation of lipases and alcohols. Journal of the American Oil Chemists Society 2005, 82:341-347.
18. Muñío M.M., Esteban L., Robles A., Hita E., Jiménez M.J., González P.A., et al. Synthesis of 2-monoacylglycerols rich in polyunsaturated fatty acids by ethanolysis of fish oil catalyzed by 1,3 specific lipases. Process Biochemistry 2008, 43:1033-1039.
19. Hita E., Robles A., Camacho B., González P.A., Esteban L., Jiménez M.J., et al. Production of structured triacylglycerols by acidolysis catalyzed by lipases immobilized in a packed bed reactor. Biochemical Engineering Journal 2009, 46:257-264.
20. Esteban Cerdán L., Robles Medina A., Giménez Jiménez A., Ibáñez González M.J., Molina Grima E. Synthesis of polyunsaturated fatty acid-enriched triglycerides by lipase-catalyzed esterification. Journal of the American Oil Chemists Society 1998, 75:1329-1337.
21. Lepage G., Roy C. Improved recovery of fatty acid through direct transesterification without prior extraction or purification. Journal of Lipid Research 1984, 25:1391-1396.
22. Rodríguez-Ruiz J., Hassan Belarbi E., García Sánchez J.L., López Alonso D. Rapid simultaneous lipid extraction and transesterification for fatty acid analysis. Biotechnology Techniques 1999, 12:689-691.
23. Robles Medina A., Esteban Cerdán L., Giménez Giménez A., Camacho Páez B., Ibáñez González M.J., Molina Grima E. Lipase-catalyzed esterification of glycerol and polyunsaturated fatty acids from fish and microalgae oils. Journal of Biotechnology 1999, 70:379-391.
24. Henderson R.J., Tocher D.R. Thin-layer chromatography. Lipids analysis: a practical approach 1992, 65-111. IRL Press, Oxford. R.J. Hamilton, S. Hamilton (Eds.).
25. Shimada Y., Ogawa J., Watanabe Y., Nagao T., Kawashima A., Kobayashi T., et al. Regiospecific analysis by ethanolysis of oil with immobilized Candida antarctica lipase. Lipids 2003, 38:1281-1286.
26. Shen Z., Wijasundera C. Evaluation of ethanolysis with immobilized Candida antarctica lipase for regiospecific analysis of triacylglycerols containing highly unsaturated fatty acids. Journal of the American Oil Chemists Society 2006, 83:923-927.
27. Muñío M.M., Robles A., Esteban L., González P.A., Molina E. Synthesis of structured lipids by two enzymatic steps: ethanolysis of fish oils and esterification of 2-monoacylglycerols. Process Biochemistry 2009, 44:723-730.
28. Esteban L., Muñío M.M., Robles A., Hita E., Jiménez M.J., González P.A., et al. Synthesis of 2-monoacylglycerols (2-MAG) by enzymatic alcoholysis of fish oils using different reactor types. Biochemical Engineering Journal 2009, 44:271-279.
29. González Moreno P.A., Robles Medina A., Camacho Rubio F., Camacho Páez B., Molina Grima E. Production of structured lipids by acidolysis of an EPA-enriched fish oil and caprylic acid in a packed bed reactor: analysis of three different operation modes. Biotechnology Progress 2004, 20:1044-1052.