Enzymatic synthesis of feruloylated lysophospholipid in a selected organic solvent medium

Food Chemistry

Volumn 141, Issue 4, 2013, Pages 3317-3322

  Yang, Hongli ^a   Mu, Ying ^a   Chen, Hongtao ^a   Xiu, Zhilong ^a   Yang, Tiankui ^a,b  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b GE (China) Research   (China)

Author keywords

Enzymatic modification; Ethyl ferulate; Feruloylated lysophospholipids; Lipase; Phosphatidylcholine

Indexed keywords

ACETONE; CHLORINE COMPOUNDS; LIPASES; MOLECULAR SIEVES; PHOSPHOLIPIDS; SOLVENTS; SUBSTRATES; TOLUENE;

ENZYMATIC MODIFICATION; ENZYMATIC SYNTHESIS; ETHYL FERULATE; INTERESTERIFICATION; LYSOPHOSPHOLIPIDS; OPTIMAL COMBINATION; ORGANIC SOLVENT MEDIUM; PHOSPHATIDYLCHOLINE;

ORGANIC SOLVENTS;

2 PROPANOL; ACETONE; BUTANOL; CHLOROFORM; CYCLOHEXANE; DIMETHYL SULFOXIDE; ETHYL FERULATE; FERULIC ACID; FERULOYLATED LYSOPHOSPHOLIPID; HEXANE; LYSOPHOSPHOLIPID; ORGANIC SOLVENT; PROPANOL; TERT BUTYL ALCOHOL; TOLUENE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; ENZYME SYNTHESIS; HYDROLYSIS; INTERESTERIFICATION; NONHUMAN; QUALITATIVE ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; THERMOMYCES LANUGINOSUS; WATER CONTENT;

ENZYMATIC MODIFICATION; ETHYL FERULATE; FERULOYLATED LYSOPHOSPHOLIPIDS; LIPASE; PHOSPHATIDYLCHOLINE;

BIOCATALYSIS; BIOTECHNOLOGY; CAFFEIC ACIDS; ESTERIFICATION; LIPASE; LYSOPHOSPHOLIPIDS; PHOSPHATIDYLCHOLINES;

EID: 84880182687     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.06.012     Document Type: Article

References (28)

1. Adlercreutz, D., Budde, H., & Wehtje, E. (2001). Synthesis of phosphatidylcholine with defined fatty acid in the sn-1 position by lipase-catalyzed esterification and transesterification reaction. Biochemistry and Bioengineering, 78, 403-411 (Pubitemid 34712360)
2. Arpigny, J. L., & Jaeger, K. E. (1999). Bacterial lipolytic enzymes: Classification and properties. Biochemistry Journal, 343, 177-183 (Pubitemid 29473893)
3. Caro, Y., Pina, M., Turon, F, Turon, S., Guilbert, S., Mougeot, E., et al. (2002). Plant lipases: Biocatalyst aqueous environment in relation to optimal catalytic activity in lipase-catalyzed synthesis reactions. Biotechnology and Bioengineering, 77, 693-703 (Pubitemid 34712332)
4. Chen, B., Liu, H., Guo, Z., Huang, M., Xu, X., & Zheng, L. (2011). Lipase-catalyzed esterification of ferulic acid with oleyl alcohol in ionic liquid/isooctane/binary systems. Journal of Agricultural and Food Chemistry, 59, 1256-1263
5. Compton, D. L., Laszlo, J. A., & Berhow, M. A. (2000). Lipase-catalyzed synthesis of ferulate esters. Journal of the American Oil Chemists? Society, 77, 513-519
6. Doukyu, N., & Ogino, H. (2010). Organic solvent-tolerant enzymes. Biochemical Engineering Journal, 48, 270-282
7. Guo, Z., Vikbjerg, A., & Xu, X. (2005). Enzymatic modification of phospholipids for functional applications and human nutrition. Biotechnology Advances, 23, 203-259 (Pubitemid 40346246)
8. He, W. S., Jia, C. S., Ma, Y., Yang, Y. B., Zhang, X. M., Feng, B., et al. (2010). Lipasecatalyzed synthesis of phytostanyl esters in non-aqueous medium. Journal of Molecular Catalysis B: Enzymatic, 67, 60-65
9. Kima, I. H., Yoonb, C. S., & Leec, K. W. (2001). Transesterification of conjugated linoleic acid and tricaprylin by lipases in organic solvents. Food Research International, 34, 301-306
10. Klibanov, A. M. (1997). Why are enzymes less active in organic solvents than in water? Trends in Biotechnology, 15, 97-101
11. Kuntal, M., Kakali, M., Arunava, G., Bishnu, P. S., & Pulok, K. M. (2007). Curcumin-phospholipid complex: Preparation, therapeutic evaluation and pharmacokinetic study in rats. International Journal of Pharmaceutics, 330, 155-163
12. Kuwabara, K., Watanabe, Y., Adachi, S., Nakanishi, K., & Matsuno, R. (2003). Synthesis of 6-O-unsaturated acyl L-ascorbates by immobilized lipase in acetone in the presence of molecular sieve. Biochemical Engineering Journal, 16, 17-22 (Pubitemid 37064216)
13. Lara, P. V., & Park, E. Y. (2004). Potential application of waste activated bleaching earth on the production of fatty acid alkyl esters using Candida cylindracea lipase in organic solvent system. Enzyme and Microbial Technology, 34, 270-277 (Pubitemid 38186734)
14. Laszlo, J. A., & Compton, D. L. (2006). Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols. Journal of the American Oil Chemists? Society, 83, 765-770 (Pubitemid 44562598)
15. Li, Y., Yang, D. J., Chen, S. L., Chen, S. B., & Chan, A. (2008). Process parameters and morphology in puerarin, phospholipids and their complex microparticles generation by supercritical antisolvent precipitation. International Journal of Pharmaceutics, 359, 35-45
16. Murakami, A., Nakamurab, Y., Koshimizua, K., Takahashi, D., Matsumotoa, K., Hagiharaa, K., et al. (2002). FA15, a hydrophobic derivative of ferulic acid, suppresses inflammatory responses and skin tumor promotion: Comparison with ferulic acid. Cancer Letters, 180, 121-129 (Pubitemid 34327364)
17. Nicks, F., Richel, A., Richard, G., Laurent, P., Wathelet, B., Wathelet, J. P., et al. (2012). Green synthesis and antioxidant activity of new PEGylated ferulic acids. Tetrahedron Letters, 53, 2402-2405
18. Rice-Evans, C., Miller, N., & Paganga, G. (1997). Antioxidant properties of phenolic compounds. Trends in Plant Science, 2, 152-159 (Pubitemid 27158898)
19. Srinivasan, M., Sudheer, A. R., & Menon, V. P. (2007). Ferulic acid: therapeutic potential through its antioxidant property. Journal Clinical Biochemistry & Nutrition, 40, 92-100 (Pubitemid 46623810)
20. Sun, S. D., Shan, L., Liu, Y. F., Jin, Q. Z., Zhang, L. X., & Wang, X. G. (2008). Solvent-free enzymatic preparation of feruloylated monoacylglycerols optimized by response surface methodology. Journal of Agricultural and Food Chemistry, 56, 442-447 (Pubitemid 351212569)
21. Tung, Y. T., Wu, J. H., Kuo, Y. H., & Chang, S. T. (2007). Antioxidant activities of natural phenolic compounds from Acacia confusa bark. Bioresource Technology, 98, 1120-1123
22. Xiao, Y. Y., Song, Y. M., Chen, Z. P., & Ping, Q. N. (2006). The preparation of silybin-phospholipid complex and the study on its pharmacokinetics in rats. International Journal of Pharmaceutics, 307, 77-82
23. Yang, T., Xu, X., He, C., & Li, L. (2003). Lipase-catalyzed modification of lard to produce human milk fat substitutes. Food Chemistry, 80, 473-481 (Pubitemid 36143987)
24. Yang, Z., Glasius, M., & Xu, X. (2012). Enzymatic transesterification of ethyl ferulate with fish oil and reaction optimization by response surface methodology. Food Technology Biotechnology, 50, 88-97
25. Yang, Z., Guo, Z., & Xu, X. (2012). Enzymatic lipophilisation of phenolic acids through esterification with fatty alcohols in organic solvents. Food Chemistry, 132, 1311-1315
26. Zhang, H., Xu, X., Mu, H., Nilsson, J., Adler-Nissen, J., & Høy, C. E. (2000). Lipozyme IM-catalyzed interesterification for the production of margarine fats in a 1 kg scale stirred tank reactor. European Journal of Lipid Science and Technology, 102, 411-418
27. Zheng, Y., Wu, X. M., Branford-White, C., Ning, X., Quan, J., & Zhu, L. M. (2009). Enzymatic synthesis and characterization of novel feruloylated lipids in selected organic media. Journal of Molecular Catalysis: Enzymatic, 58, 65-71
28. Zhong, N., Li, L., Xu, X., Cheong, L. Z., Li, B., Hu, S., et al. (2009). An efficient binary solvent mixture for monoacylglycerol synthesis by enzymatic glycerolysis. Journal of the American Oil Chemists? Society, 86, 783-789