Enzymatic synthesis of phenolic lipids using flaxseed oil and ferulic acid in supercritical carbon dioxide media

Journal of Supercritical Fluids

Volumn 72, Issue , 2012, Pages 255-262

  Ciftci, Deniz ^a   Saldaña, Marleny D A ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Enzymatic reaction; Flaxseed oil; Lipase; Response surface methodology; Supercritical carbon dioxide

Indexed keywords

CANDIDA ANTARCTICA; CENTRAL COMPOSITE ROTATABLE DESIGN; ENZYMATIC REACTION; ENZYMATIC SYNTHESIS; FERULIC ACIDS; FLAXSEED OIL; GREEN SOLVENTS; HIGHER YIELD; IMMOBILIZED LIPASE; MODERATE PRESSURES; MOLAR RATIO; OPTIMUM REACTION CONDITIONS; PHENOLIC LIPIDS; PREDICTED YIELD; REACTION CONDITIONS; RESPONSE SURFACE METHODOLOGY; SUPERCRITICAL CARBON DIOXIDES;

CARBON DIOXIDE; FLAX; LIPASES; LIPIDS; OILSEEDS; SUPERCRITICAL FLUID EXTRACTION; SURFACE PROPERTIES;

PHENOLS;

EID: 84868226725     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2012.09.007     Document Type: Article

References (36)

1. A. Murakami, Y. Nakamura, K. Koshimizu, D. Takahashi, K. Matsumoto, K. Hagihara, H. Taniguchi, E. Nomura, A. Hosoda, T. Tsuno, Y. Maruta, H.W. Kim, K. Kawabata, and H. Ohigashi FA15, a hydrophobic derivative of ferulic acid, suppresses inflammatory responses and skin tumor promotion: comparison with ferulic acid J. Cancer Letters 180 2002 121 129
2. F.H. Lin, J.Y. Lin, R.D. Gupta, J.A. Tournas, J.A. Burch, M.A. Selim, N.A. Monteiro-Riviere, J.M. Grichnik, J. Zielinski, and S.R. Pinnell Ferulic acid stabilizes a solution of vitamins C and E and doubles its photoprotection of skin J. Investigative Dermatology 125 2005 826 832
3. 2 J. American Oil Chemists' Society 78 2001 43 47
4. K. Sabally, S. Karboune, F.K. Yebaoh, and S. Kermasha Lipase-catalyzed esterification of linolenyl alcohol with selected phenolic acids in organic solvent media Applied Biochemistry and Biotechnology 127 2005 17 28
5. K. Sabally, S. Karboune, R. St-Louis, and S. Kermasha Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids J. American Oil Chemists' Society 83 2006 101 107
6. K. Sabally, S. Karboune, R. St-Louis, and S. Kermasha Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids J. Biotechnology 127 2006 167 176
7. K. Sabally, S. Karboune, R. St-Louis, and S. Kermasha Lipase-catalyzed synthesis of phenolic lipids from fish liver oil and dihydrocaffeic acid J. Biocatalysis and Biotransformation 25 2007 211 218
8. Y. Zheng, X.M. Wu, C. Brandford-White, X. Ning, J. Quan, and L.M. Zhu Enzymatic synthesis and characterization of novel feruloylated lipids in selected organic media J. Molecular Catalysis B: Enzymatic 58 2009 65 71
9. Z. Yang, V. Feddern, M. Glasius, Z. Guo, and X. Xu Improved enzymatic production of phenolated acylglycerols through alkyl phenolate intermediates Biotechnology Letters 33 2011 673 679
10. H. Kikuzaki, M. Hisamoto, K. Hirose, K. Akiyama, and H. Taniguchi Antioxidant properties of ferulic acid and its related compounds J. Agricultural and Food Chemistry 50 2002 2161 2168
11. S.P. Kochar Stable and healthful frying oil for the 21st century Inform 11 2000 642 647
12. D.L. Compton, J.A. Laszlo, and M.A. Berhow Lipase-catalyzed synthesis of ferulate esters J. American Oil Chemists' Society 77 2000 513 519
13. S. Kaur, and M. Das Functional foods: an overview Food Science and Biotechnology 20 2011 861 875
14. J.A. Laszlo, and D.L. Compton Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols J. American Oil Chemists' Society 83 2006 765 770
15. M. Tsuchiyama, T. Sakamoto, T. Fujita, S. Murata, and S. Kawasaki Esterification of ferulic acid with polyols using a ferulic acid esterase from Aspergillus niger Biochimica et Biophysica Acta - General Subjects 1760 2006 1071 1079
16. F.D. Gunstone Enzymes as biocatalysts in the modification of natural lipids J. Science of Food and Agriculture 79 1999 1535 1549
17. S. Karboune, R. St-Louis, and S. Kermasha Enzymatic synthesis of structured phenolic lipids by acidolysis of flaxseed oil with selected phenolic acids J. Molecular Catalysis B: Enzymatic 52-53 2008 96 105
18. R. Karam, S. Karboune, R. St-Louis, and S. Kermasha Lipase-catalyzed acidolysis of fish liver oil with dihydroxyphenylacetic acid in organic solvent media Process Biochemistry 44 2009 1193 1199
19. H. Black Supercritical carbon dioxide: the "greener" solvent Environmental Science and Technology 30 1996 124A 128A
20. J. Chalas, C. Claise, M. Edeas, C. Messaoudi, L. Vergnes, A. Abella, and A. Lindenbaum Effect of ethyl esterification of phenolic acids on low-density lipoprotein oxidation Biomedicine and Pharmacotherapy 55 2001 54 60
21. S. Kamat, G. Critchley, E.J. Beckman, and A.J. Russell Enzyme activity in supercritical fluids Critical Reviews in Biotechnology 15 1995 41 71
22. B. Seifried, and F. Temelli Interfacial tension of marine lipids in contact with high pressure carbon dioxide J. Supercritical Fluids 52 2010 203 214
23. NIST Chemistry Webbook, Available from: http://webbook.nist.gov, (accessed in March 2012).
24. 2 J. Supercritical Fluids 17 2000 35 44
25. 2 Industrial and Engineering Chemistry Research 39 2000 4450 4454
26. Y. Ikushima, N. Saito, M. Arai, and H.W. Blanch Activation of a lipase triggered by interactions with supercritical carbon dioxide in the near-critical region J. Physical Chemistry 99 1995 8941 8944
27. M. Habulin, and Z. Knez Activity and stability of lipases from different sources in supercritical carbon dioxide and near-critical propane J. Chemical Technology and Biotechnology 76 2001 1260 1266
28. S. Garcia, N.M.T. Lourenco, D. Lousa, A.F. Sequeira, P. Mimoso, J.M.S. Cabral, C.A.M. Afonso, and S. Barreiros A comparative study of biocatalysis in non-conventional solvents: ionic liquids, supercritical fluids and organic media Green Chemistry 6 2004 466 470
29. H.R. Hobbs, and N.R. Thomas Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions Chemical Reviews 107 2007 2786 2820
30. Novo Nordisk, Technical Report, A-05948 (1992).
31. C. Turner, M. Persson, L. Mathiasson, P. Adlercreutz, and J.W. King Lipase-catalyzed reactions in organic and supercritical solvents: application to fat-soluble vitamin determination in milk powder and infant formula Enzyme and Microbial Technology 29 2001 111 121
32. 2 Biotechnology Letters 21 1999 65 69
33. K.A. Rezaei, F. Temelli, and E. Jenab Effects of pressure and temperature on enzymatic reactions in supercritical fluids Biotechnology Advances 25 2007 272 280
34. O.N. Ciftci, and F. Temelli Continuous production of fatty acid methyl esters from corn oil in a supercritical carbon dioxide bioreactor J. Supercritical Fluids 58 2011 79 87
35. G.H.C. Prado, M. Khan, M.D.A. Saldaña, and F. Temelli Enzymatic hydrolysis of conjugated linoleic acid-enriched anhydrous milk fat in supercritical carbon dioxide J. Supercritical Fluids 66 2012 198 206
36. B. Seifried, and F. Temelli Viscosity and rheological behaviour of carbon dioxide-expanded fish oil triglycerides: measurement and modeling J. Supercritical Fluids 59 2011 27 35