Enzymatic strategies for solvent-free production of short and medium chain phytosteryl esters

European Journal of Lipid Science and Technology

Volumn 114, Issue 6, 2012, Pages 670-676

  Torrelo, Guzman ^a   Torres, Carlos F ^a   Reglero, Guillermo ^a  

^a CSIC   (Spain)

Author keywords

Butyric acid; Candida rugosa lipase; Phytosteryl ester; Pseudomonas stutzeri TL lipase; Short and medium chain fatty acids

Indexed keywords

CANDIDA RUGOSA; PSEUDOMONAS STUTZERI;

EID: 84862222381     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201100346     Document Type: Article

References (40)

1. Kritchevsky, D., Chen, S.C., Phytosterols - Health benefits and potential concerns: A review. Nutr. Res. 2005, 25, 413- 428.
2. Quílez, J., García-Lorda, P., Salas-Salvado, J., Potential uses and benefits of phytosterols in diet: Present situation and future directions. Clin. Nutr. 2003, 22, 343- 351.
3. de Jong, A., Plat, J., Mensink, R.P., Metabolic effects of plant sterols and stanols (Review). J. Nutrl. Biochem. 2003, 14, 362- 369.
4. Trautwein, E.A., Duchateau, G.S.M.J.E., Lin, Y., Mel'nikov, S.M., et al., Proposed mechanisms of cholesterol-lowering action of plant sterols. Eur. J. Lipid Sci. Technol. 2003, 105, 171- 185.
5. Mulligan, J.D., Flowers, M.T., Tebon, A., Bitgood, J.J., et al., ABCA1 is essential for efficient basolateral cholesterol efflux during the absorption of dietary cholesterol in chickens. J. Biol. Chem. 2003, 278, 13356- 13366.
6. Plat, J., Mensink, R.P., Plant stanol and sterol esters in the control of blood cholesterol levels: Mechanism and safety aspects. Am. J. Cardiol. 2005, 96, 15- 22.
7. Awad, A.B., Roy, R., Fink, C.S., Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol. Rep. 2003, 10, 497- 500.
8. Moghadasian, M.H., McManus, B.M., Pritchard, P.H., Frohlich, J.J., "Tall oil" - Derived phytosterols reduce atherosclerosis in ApoE-deficient mice. Arterioscler. Thromb. Vasc. Biol. 1997, 17, 119- 126.
9. Moghadasian, M.H., McManus, B.M., Godin, D.V., Rodrigues, B., Frohlich, J.J., Proatherogenic and antiatherogenic effects of probucol and phytosterols in apolipoprotein E-deficient mice: Possible mechanisms of action. Circulation 1999, 99, 1733- 1739.
10. Bouic, P.J.D., The role of phytosterols and phytosterolins in immune modulation: A review of the past 10 years. Curr. Opin. Clin. Nutr. Metab. Care 2001, 4, 471- 475.
11. van Rensburg, S.J., Daniels, W.M.U., van Zyl, J.M., Taljaard, J.J.F., A Comparative study of the effects of cholesterol, beta-sitosterol, beta-sitosterol glucoside, dehydro-epiandrosterone sulphate and melatonin on in vitro lipid peroxidation. Metab. Brain Dis. 2000, 15, 257- 265.
12. Rozner, S., Garti, N., The activity and absorption relationship of cholesterol and phytosterols. Colloid. Surface. A 2006, 435- 456
13. Kles, K.A., Chang, E.B., Short-chain fatty acids impact on intestinal adaptation, inflammation, carcinoma, and failure. Gastroenterology 2006, 130, S100- S105.
14. Rombeau, J.L., Investigations of short-chain fatty acids in humans. Clin. Nutr. Suppl. 2004, 1, 19- 23.
15. Scheppach, W., Christl, S.U., Bartram, H.P., Richter, F., Kasper, H., Effects of short-chain fatty acids on the inflamed colonic mucosa. Scand. J. Gastroenterol. Suppl. 1997, 222, 53- 57.
16. Vernia, P., Annese, V., Bresci, G., d'Albasio, G., et al., Topical butyrate improves efficacy of 5-ASA in refractory distal ulcerative colitis: Results of a multicentre trial. Eur. J. Clin. Investig. 2003, 33, 244- 248.
17. Hamer, H.M., Jonkers, D., Venema, K., Vanhoutvin, S., et al., Review article: The role of butyrate on colonic function. Aliment. Pharmacol. Ther. 2008, 27, 104- 119.
18. Smith, J.G., Yokoyama, W.H., German, J.B., Butyric acid from the diet: Actions at the level of gene expression. Crit. Rev. Food Sci. 1998, 38, 259- 297.
19. Yamamoto, H., Fujimoto, J., Okamoto, E., Furuyama, J-I., et al., Suppression of growth of hepatocellular carcinoma by sodium butyrate in vitro and in vivo. Int. J. Cancer 1998, 76, 897- 902.
20. Coradini, D., Biffi, A., Costa, A., Pellizzaro, C., et al., Effect of sodium butyrate on human breast cancer cell lines. Cell Prolif. 1997, 30, 149- 159.
21. Hodin, R.A., Meng, S., Archer, S., Tang, R., Cellular growth state differentially regulated enterocyte gene expression ion butyrate-treated HT29 cells. Cell Growth Differ. 1996, 7, 647- 653.
22. Egorin, M.J., Yuan, Z-M., Sentz, D.L., Plaisance, K., Eiseman, J.L., Plasma pharmacokinetics of butyrate after intravenous administration of sodium butyrate or oral administration of tributyrin or sodium butyrate to mice and rats. Cancer Chemother. Pharmacol. 1999, 43, 445- 453.
23. Ugazio, E., Marengo, E., Pellizzaro, C., Coradini, D., et al., The effect of formulation and concentration of cholesteryl butyrate solid lipid nanospheres (SLN) on NIH-H460 cell proliferation. Eur. J. Pharm. Biopharm. 2001, 52, 197- 202.
24. Demonty, I., Chan, Y-M., Pelled, D., Jones, P.J.H., Fish-oil esters of plant sterols improve the lipid profile of dyslipidemic subjects more than do fish-oil or sunflower oil esters of plant sterols. Am. J. Clin. Nutr. 2006, 84, 1534- 1542.
25. Kim, B.H., Akoh, C.C., Modeling and optimization of lipase-catalyzed synthesis of phytosteryl esters of oleic acid by response surface methodology. Food Chem. 2007, 102, 336- 342.
26. Villeneuve, P., Turon, F., Caro, Y., Escoffier, R., et al., Lipase-catalyzed synthesis of canola phytosterols oleate esters as cholesterol lowering agents. Enzyme Microb. Technol. 2005, 37, 150- 155.
27. Vu, P.L., Shin, J.A., Lim, C.H., Lee, K.T., Lipase-catalyzed production of phytosteryl esters and their crystallization behavior in corn oil. Food Res. Int. 2004, 37, 175- 180.
28. Torrelo, G., Torres, C.F., Señorans, F.J., Blanco, R.M., Reglero, G., Solvent-free preparation of phytosteryl esters with fatty acids from butterfat in equimolecular conditions in the presence of a lipase from Candida rugosa. J. Chem. Technol. Biotechnol. 2009, 84, 745- 750.
29. Torres, C.F., Torrelo, G., Senorans, F.J., Reglero, G., Supercritical fluid fractionation of fatty acid ethyl esters from butteroil. J. Dairy Sci. 2009, 92, 1840- 1845.
30. Torres, C., Tenllado, D., Señorans, F., Reglero, G., A versatile GC method for the analysis of alkylglycerols and other neutral lipid classes. Chromatographia 2009, 69, 729- 734.
31. Weber, N., Weitkamp, P., Mukherjee, K.D., Cholesterol-lowering food additives: Lipase-catalysed preparation of phytosterol and phytostanol esters. Food Res. Int. 2002, 35, 177- 181.
32. Weber, N., Weitkamp, P., Mukherjee, K.D., Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst. J. Agric. Food Chem. 2001, 49, 67- 71.
33. Lyberg, A-M., Adlercreutz, P., Lipase specificity towards eicosapentaenoic acid and docosahexaenoic acid depends on substrate structure BBA Proteins Proteomic. 2008, 1784, 343- 350.
34. Scott, C.D., Scott, T.C., Blanch, H.W., Klibanov, A.M., Russell, A.J., Bioprocessing in nonaqueous media: Critical needs and opportunities. 1996, Oak Ridge National Laboratory, Report ORNL/TM -12849, 5.
35. de Castro, H.F., de Oliveira, P.C., Pereira, E.B., Evaluation of different approaches for lipase catalysed synthesis of citronellyl acetate. Biotechnol. Lett. 1997, 19, 229- 232.
36. Razafindralambo, H., Blecker, C., Lognay, G., Marlier, M., et al., Improvement of enzymatic synthesis yields of flavour acetates: The example of the isoamyl acetate. Biotechnol. Lett. 1994, 16, 247- 250.
37. Prapulla, S.G., Karanth, N.G., Engel, K.H., Tressl, R., Production of 6-pentyl-α-pyrone by Trichoderma viride. Flavour Frag. J. 1992, 7, 231- 234.
38. Welsh, F.W., Williams, R.E., Dawson, K.H., Lipase mediated synthesis of low molecular weight flavor esters. J. Food Sci. 1990, 55, 1679- 1682.
39. Martínez, I., Markovits, A., Chamy, R., Markovits, A., Lipase-catalyzed solvent-free transesterification of wood sterols. Appl. Biochem. Biotechnol. 2004, 112, 55- 62.
40. Peter J.H., Thermodynamic predictions for biocatalysis in nonconventional media: Theory, tests, and recommendations for experimental design and analysis. Enzyme. Microb. Technol. 1994, 16, 178- 206.