Lipase-catalyzed synthesis of structured phenolic lipids in solvent-free system using flaxseed oil and selected phenolic acids as substrates

Journal of Biotechnology

Volumn 158, Issue 3, 2012, Pages 128-136

  Sorour, Noha ^a   Karboune, Salwa ^a   Saint Louis, Richard ^b   Kermasha, Selim ^a  

^a MCGILL UNIVERSITY   (Canada)

^b UNIVERSITÉ DU QUÉBEC À RIMOUSKI   (Canada)

Author keywords

Flaxseed oil; Phenolic acids; Phenolic lipids; Solvent free system; Transesterification

Indexed keywords

APCI-MS; BENZOIC ACID; BIOCONVERSION YIELDS; ENZYMATIC ACTIVITIES; FLAXSEED OIL; HEXADECYLTRIMETHYLAMMONIUM BROMIDE; LIPASE-CATALYZED; LIPASE-CATALYZED SYNTHESIS; ORGANIC SOLVENT SYSTEM; PHENOLIC ACIDS; PHENOLIC LIPIDS; REACTION MIXTURE; SOLVENT-FREE SYSTEM; SULFOSUCCINATE; VOLUMETRIC PRODUCTIVITY;

ACETIC ACID; ANIONIC SURFACTANTS; BROMINE COMPOUNDS; CARBOXYLIC ACIDS; CATALYSIS; FLAX; LIPIDS; OILSEEDS; ORGANIC SOLVENTS; SOLVENTS; TRANSESTERIFICATION;

PHENOLS;

3,4 DIHYDROXYPHENYLACETIC ACID; ACETIC ACID DERIVATIVE; ANIONIC SURFACTANT; BENZOIC ACID DERIVATIVE; CATION; CETRIMIDE; CINNAMIC ACID DERIVATIVE; DIHYDROCAFFEIC ACID; DILINOLENYLACETIC ACID; ENZYME; FERULIC ACID; LINOLEYLACETIC ACID; LINSEED OIL; LIPID; MONOLINOLENYLACETIC ACID; NONIONIC SURFACTANT; OLEYLLINOLENYLDIHYDROXYPHENYLACETIC ACID; PHENOL DERIVATIVE; PHENOLIC LIPID; PHENYLACETIC ACID DERIVATIVE; SINAPIC ACID; SODIUM BIS 2 ETHYLHEXYL SULFOSUCCINATE; SOLVENT; SUCCINIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VERATRIC ACID;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SYNTHESIS; HYDROXYLATION; LINSEED; MASS SPECTROMETRY; NONHUMAN; ORGANIC SOLVENT SYSTEM; PRIORITY JOURNAL; SOLID STATE; SOLVENT EFFECT; SOLVENT FREE SYSTEM; TRANSESTERIFICATION;

ENZYMES, IMMOBILIZED; HYDROXYBENZOIC ACIDS; HYDROXYLATION; LINSEED OIL; LIPASE;

SANDFLY FEVER SICILIAN VIRUS;

EID: 84858282157     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2011.12.002     Document Type: Article

References (39)

1. Akoh C.C., Lee K.T., Fomuso L.B. Synthesis of positional isomers of structured lipids with lipases as biocatalyst. Structural Modified Food Fats: Synthesis, Biochemistry, and Use 1998, 46-72. AOCS Press, Champaign, IL. A.B. Christophe (Ed.).
2. Bellot J.C., Choisnard L., Castillo E., Marty A. Combining solvent engineering and thermodynamic modeling to enhance selectivity during monoglyceride synthesis by lipase-catalysed esterification. Enzyme Microb. Technol. 2001, 28:362-369.
3. Buisman G.J., Van Helteren C.T., Kramer G.F., Veldsink J.W., Derksen J.T., Cuperus F.P. Enzymatic esterification of functionalized phenols for the synthesis of lipophilic antioxidants. Biotechnol. Lett. 1998, 20:131-136.
4. Dordick J.S. Designing enzymes for use in organic solvents. Biotechnol. Prog. 1992, 8:259-267.
5. Dossat V., Combes D., Marty A. Lipase catalyzed transesterification of high oleic sunflower oil: a kinetic study. Enzyme Microb. Technol. 2002, 30:90-94.
6. Dossat V., Combes D., Marty A. Efficient lipase catalyzed production of a lubricant and surfactant formulation using a continuous solvent-free process. J. Biotechnol. 2002, 97:117-124.
7. Duan Z.-Q., Du W., Liu De-H. The pronounced effect of water activity on the positional selectivity of Novozym 435 during 1,3-diolein synthesis by esterification. Catal. Commun. 2010, 11:56-358.
8. Fitzpatrick P.A., Klibanov A.M. How can the solvent affect enzyme enantioselectivity?. J. Am. Oil Chem. Soc. 1991, 113:3166-3171.
9. Fregolente P., Fregolente L., Pinto G., Batistella B., Wolf-Maciel M., Filho R. Monoglycerides and diglycerides synthesis in a solvent-free system by lipase-catalyzed glycerolysis. Appl. Biochem. Biotechnol. 2008, 146:165-172.
10. Garcia Y., Sanchez N., Martinez M., Aracil J. Enzymatic synthesis of fatty esters Part I. Kinetic approach. Enzyme Microb. Technol. 1999, 25:584-590.
11. Goto M., Kamiya N., Miyata M., Nakashio F. Enzymatic esterification by surfactant-coated lipase in organic media. Biotechnol. Prog. 1994, 10:263-268.
12. Halling P.J. Thermodynamic predictions for biocatalysis in nonconventional media: theory, tests, and recommendations for experimental design and analysis. Enzyme Microb. Technol. 1994, 16:178-206.
13. Ito N., Hirose M., Fukushima S., Tsuda H., Shirai H., Tatematsu M. Studies on autooxidants their carcinogenic and modifying effects on chemical carcinogenesis. Food Chem. Toxicol. 1986, 24:1071-1076.
14. Kamiya N., Goto M., Nakashio A. Surfactant coated lipase suitable for the enzymatic resolution of menthol as a biocatalyst in organic media. Biotechnol. Prog. 1995, 11:270-275.
15. Karam R., Karboune S., St-Louis R., Kermasha S. Lipase-catalyzed acidolysis of fish liver oil with dihydroxyphenylacetic acid in organic solvent media. Process Biochem. 2009, 44:1193-1199.
16. Karboune S., Safari M., Lue B.-M., Yebaoh F.K., Kermasha S. Lipase-catalyzed biosynthesis of cinnamoylated lipids in a selected organic solvent medium. J. Biotechnol. 2005, 119:281-290.
17. Karboune S., St-Louis R., Kermasha S. Enzymatic synthesis of structured phenolic lipids by acidolysis of flaxseed oil with selected phenolic acids. J. Mol. Catal. B: Enz. 2008, 52:96-105.
18. Kazlauskas R.J. Elucidating structure-mechanism relationships in lipases: prospects for predicting and engineering catalytic properties. Trends Biotechnol. 1994, 12:464-472.
19. Klibanov A.M. Why are enzymes less active in organic solvents than in water?. Trends Biotechnol. 1997, 15:97-101.
20. Lee K.-T., Akoh C.C. Solvent-free enzymatic synthesis of structured lipids from peanut oil and caprylic acid in a stirred tank batch reactor. J. Am. Oil Chem. Soc. 1998, 75:1533-1537.
21. Lee C.-H., Parkin K.L. Effect of water activity and immobilization on fatty acid selectivity for esterification reactions mediated by lipases. Biotechnol. Bioeng. 2001, 75:219-227.
22. Liu Y.Y., Xu J.H., Hu Y. Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester. J. Mol. Catal. B: Enz. 2000, 10:523-529.
23. Lue B.-M., Karboune S., Yebaoh F.K., Kermasha S. Lipase-catalyzed esterification of cinnamic acid and oleyl alcohol in organic solvent media. J. Chem. Technol. Biotechnol. 2005, 80:462-468.
24. Martinez I., Markovitis A., Chamy R., Markovitis A. Lipase-catalyzed solvent-free transesterification of wood sterols. Appl. Biochem. Biotechnol. 2004, 112:55-62.
25. Pencreach G., Baratti J.C. Activity of Pseudomonas cepacia lipase in organic media is greatly enhanced after immobilization on a polypropylene support. Appl. Microbiol. Biotechnol. 1997, 47:630-635.
26. Pires-Cabral P., Da Fonseca M.R., Ferreira-Dias S. Modelling the micro-environment of a lipase immobilized in polyurethane foams. Biocatal. Biotransform. 2005, 23:363-373.
27. Roche H.M. Unsaturated fatty acids. Proc. Nutr. Soc. 1999, 58:397-401.
28. Sabally K., Karboune S., St-Louis R., Kermasha S. Enzymatic structuring of trilinolein and trilinolenin with selected phenolic acids in organic solvent media. J. Am. Oil Chem. Soc. 2006, 83:101-107.
29. Sabally K., Karboune S., St-Louis R., Kermasha S. Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids. J. Biotechnol. 2006, 127:167-176.
30. Sabally K., Karboune S., St-Louis R., Kermasha S. Lipase-catalyzed synthesis of phenolic lipids from fish liver oil and dihydrocaffeic acid. Biocatal. Biotransform. 2007, 25:211-218.
31. Safari M., Karboune S., St-Louis R., Kermasha S. Enzymatic synthesis of structured phenolic lipids by incorporation of selected phenolic acids into triolein. Biocatal. Biotransform. 2006, 24:272-279.
32. SAS Version 9.2 of the SAS System for Windows 2009, SAS Institute Inc., Cary, NC, USA.
33. Shahidi F., Naczk M. Antioxidant properties of food phenolics. Food Phenolics: Sources, Chemistry, Effects Applications 1995, Technomic Publishing Co. Inc., Lancaster, PA, pp. 235-277.
34. Silva F.A., Borges F., Guimarã L.F., Matus C., Reis S. Phenolic antioxidants and derivatives: studies on the relationship among structure, radical scavenging activity and physicochemical parameters. J. Agric. Food Chem. 2000, 48:2122-2126.
35. Stamatis H., Sereti V., Kolisis F. Enzymatic synthesis of hydrophilic and hydrophobic derivatives of natural phenolic acids and in organic media. J. Mol. Catal. B: Enz. 2001, 11:323-328.
36. Torres de Pinedo A., Penalver P., Morales J. Synthesis and evaluation of new phenolic-based antioxidants: structure-activity relationship. Food Chem. 2007, 103:55-61.
37. Wei L., Wei D., Liu D., Yao Y. Study on factors influencing stability of whole cell during biodiesel production in solvent-free and tert-butanol system. J. Biochem. Eng. 2008, 41:111-115.
38. Xia J., Chen X., Nnanna I.A. Activity and stability of Penicillium cyclopium lipase in surfactant and detergent solutions. J. Am. Oil Chem. Soc. 1996, 73:115-120.
39. Yadav G., Lathi P. Kinetics and mechanism of synthesis of butyl isobutyrate over immobilized lipases. J. Biochem. Eng. 2003, 16:245-252.