Structured Lipids Produced through Lipase-Catalyzed Acidolysis of Canola Oil

Authors
D. Savaghebi 1
M. Safari 2
K. Rezaei 2
P. Ashtari 3
J. Farmani 4
1 M.Sc. Graduate from the Department of Food Science, Engineering and Technology, University of Tehran
2 Department of Food Science, Engineering and Technology, University of Tehran
3 NFCS, Nuclear Science and Technology Research Institute
4 Department of Food Science and Technology, Sari Agricultural Sciences and Natural Resources University, Sari, Iran
Abstract
Enzymatic acidolysis of canola oil through caprylic acid was investigated to produce certain medium chain Ttriacyliglycerol (TAG) structured lipids (SLs). Lipozyme TL IM, an sn-1,3 specific Thermomyces lanuginosa lipase, and Novozym 435, a non-specific Candida antarctica lipase, were utilized as the biocatalysts in a batch reactor. Reaction conditions were designed according to Taguchi’s approach, considering three levels of fatty acid to oil ratio (1:1, 2:1, and 3:1), three levels of enzyme load (4, 8 and 12%, w/w), three levels of temperature (45, 55, and 65°C) as well as three levels of reaction time (15, 30 and 45 hours). Results indicated that fatty acid composition of canola oil was modified by the above acidolysis reactions. The highest mole percent of caprylic acid incorporation (37.2 mole%) was obtained after 15 hours of incubation in the presence of Lipozyme TL IM at 55°C, fatty acid to oil ratio of 3:1 and at 12% of enzyme level. However, with Novozym 435 the highest level of incorporation (38.5 mole%) was obtained after 45 hours of reaction at 45°C, fatty acid to oil ratio of 3:1, and at 8% enzyme level. Novozym 435 was able to incorporate more caprylic acid in the oil than did Lipozyme TL IM. SLs prepared using either Lipozyme TL IM or Novozym 435 differed in terms of their TAG compositions. According to the obtained results, SLs produced by use of Lipozyme TL IM lipase contained higher levels of MLM-type (Medium-Long-Medium) triacylglycerols than those produced using Novozym 435 lipase (21.2 and 9.9%, respectively).

Keywords

1. Akoh, C. C. and Moussata, C. O. 2001. Characterization and Oxidative Stability of Enzymatically Produced Fish and Canola Oil-Based Structured Lipids. J. Am. Oil Chem. Soc., 78 (1): 25-30.
2. Bray, G., Lee, M. and Bray, T. 1980. Weight Gain of Rats Fed Medium-chain Triglycerides is Less than Rats Fed Long-chain Triglycerides. Int. J. Obes., 4: 27-32.
3. Farmani, J., Hamedi, M. and Safari, M. 2008. Production of Zero Trans Iranian Vanaspati Using Chemical Transesterification and Blending Techniques from Palm Olein, Rapeseed and Sunflower Oil. Int. J. Food Sci. Technol., 43: 393-399.
4. Farmani, J., Safari, M. and Hamedi, M. 2009. Trans-free Fats through Interesterification of Canola Oil/Palm Olein or Fully Hydrogenated Soybean Oil Blend. Eur. J. Lipid Sci. Technol., 111(12): 1212- 1220.
5. Fomuso, L. B. and Akoh, C. C. 2002. Lipase-catalyzed Acidolysis of Olive Oil and Caprylic Acid in a Bench-scale Packed Bed Bioreactor. Food Res. Int., 35: 15-21.
6. Hamam, F. and Shahidi, F. 2005. Enzymatic Incorporation of Capric Acid into a Single Cell Oil Rich in Docosahexaenoic Acid and Docosapentaenoic Acid and Oxidative Stability of the Resultant Structured Lipid. Food Chem., 91: 583–591.
7. Huang, Z., Wang, B. and Crenshaw, A. A. 2006. A Simple Method for the Aanalysis of Trans Fatty Acid with GC–MS and ATe-Silar-90 Capillary Column. Food Chem., 98: 593-598.
8. Iwasaki, Y. and Yamane, T .2004. Enzymatic Synthesis of Structured Lipids. Adv. Biochem. Eng. Biotechnol., 90: 151–171.
9. Jennings, B. H. and Akoh, C. C. 2000. Lipase Catalyzed Modification of Rice Bran Oil to Incorporate Capric Acid. J. Agric. Food Chem., 48: 4439- 4443.
10. Jimenez, M. J., Esteban, L., Robles, A., Hita, E., Gonzalez, P. A., Munio, M. M. and Molina, E. 2010. Production of Triacylglycerols Rich in Palmitic Acid at sn-2 Position by Lipase-catalyzed Acidolysis. Biochem. Eng. J., 51:172–179.
11. Karabulut, I., Durmaz, G. and Hayaloglu, A. A. 2009. Fatty Acid Selectivity of Lipases during Acidolysis Reaction between Triolein and Saturated Fatty Acids Varying from Caproic to Behenic Acids. J. Agric. Food Chem., 57: 7584–7590.
12. Karabulut, I., Durmaz, G. and Hayaloglu, A. A. 2010. C18 Unsaturated Fatty Acid Selectivity of Lipases During the Acidolysis Reaction between Tripalmitin and Oleic, Linoleic, and Linolenic Acids. J. Am. Oil Chem. Soc., 87: 1301–1307.
13. Kennedy, J. P. 1991. Structured Lipids: Fats of the Future. Food Technol., 44: 76-83.
14. Kim, B. H. and Akoh, C. C. 2005. Chemical and Physical Properties of Butterfat-Vegetable Oil Blend Spread Prepared with Enzymatically Transesterified Canola Oil and Caprylic Acid. J. Agric. Food Chem., 53: 4954-4961.
15. Kim, H. R., Hou, C. T., Lee, K. T., Kim, B. H. and Kim, I. H. 2010. Enzymatic Synthesis of Structured Lipids Using a Novel Cold-active Lipase from Pichialynferdii NRRL Y-7723. Food Chem., 122: 846–849.
16. Kim, I., Kim, H., Lee, K., Chung, S. and Ko, S. 2002. Lipase-catalyzed Acidolysis of Perilla Oil with Caprylic Acid to Produce Structured Lipids. J. Am. Oil Chem. Soc., 79: 363–367.
17. Kim, I. H., Yoon, C. S., Cho, S. H., Lee, K. W., Chung, S. H. and Tae, B. S. 2001. Lipase-catalyzed Incorporation of Conjugated Linoleic Acid into Tricaprylin. J. Am. Oil Chem. Soc., 78: 547–551.
18. Long, K., Ghazali, H. M., Ariff, A. and Bucke, C. 1997. Acidolysis of Several Vegetable Oils by Mycelium-bound Lipase of Aspergillusflavus Link. J. Am. Oil Chem. Soc., 74 (9): 1121-1128.
19. Official Methods and Recommended Practices of the American Oil Chemists’ Society. 1996. 4th Edition, AOCS Press, Champaign, IL (USA).
20. Ozturk, T., Ustun, G. and Aksoy, H. A. 2010. Production of Medium-chain Triacylglycerols from Corn Oil: Optimization by Response Surface Methodology. Bioresource Technol., 101: 7456–7461.
21. Przybylski, R., Mag, T., Eskin, N. A. M. and McDonald, B. E. 2005. Canola Oil. In: "Bailey’s Industrial Oil and Fat Products". Wiley-VCH, New York, 2: 61–121.
22. Rahimi, S., Kamran Azad , S. and Karimi Torshizi, M. A. 2011. Omega-3 Enrichment of Broiler Meat by Using Two Oil Seeds. J. Agr. Sci. Tech., 13: 353-365.
23. Roy, R. K. 1990. A Primer on the Taguchi Method, Van Nostrand Reinhold, New York.
24. Senanayake, S. P. J. N. and Shahidi, F. 2002. Enzyme-catalyzed Synthesis of Structured Lipids via Acidolysis of Seal (Phocagroenlandica) Blubber Oil with Capric Acid. Food Res. Int., 35: 745-752.
25. Watkins, S. M. and German, J. B. 2008. Unsaturated Fatty Acids. In: "Food lipids: Chemistry, Nutrition, and Biotechnology", (Eds.): Akoh C. C. and Min, D. B.. Taylor and Francis Group, New York, PP. 513-538.
26. Weete, J. D., Lai O. M. and Akoh, C. C. 2008. Microbial Lipases. In: "Food lipids: Chemistry, Nutrition, and Bbiotechnology", (Eds.): Akoh C. C. and Min, D. B.. Taylor and Francis Group, New York, PP. 767-806.
27. Xu, X. 2000. Production of Specific-structured Triacylglycerols by Lipase-Catalyzed Reactions: A Review. Eur. J. Lipid Sci. Technol., 102: 287–303.
28. Xu, X., Timm-Heinrich, M., Nielsen, N. S., Porsgaard, T. and Jacobsen, C. 2005. Effects of Antioxidants on the Lipase-catalyzed Acidolysis during Production of Structured Lipids, Eur. J. Lipid Sci. Technol., 107: 464–468.
29. Xu, X., Fomuso, L.B. and Akoh, C. C. 2000. Synthesis of Structured Triacylglycerols by Lipase-catalyzed Acidolysis in a Packed Bed Bioreactor. J. Agric. Food Chem., 48: 3-10.
30. Xu, X., Jacobsen, C., Nielsen, N.S., Timm-Heinrich, M. and Zhou, D. 2002. Purification and Deodorization of Structured Lipids by Short Path Distillation. Eur. J. Lipid Sci. Technol., 104: 745–755.
31. Xu, X., Skands, A. R. H., Alder-Nissen, J. and Hoy, C. 1998. Production of Specific Structured Lipids by Enzymatic Interesterification: Optimization of the Reaction by Response Surface Design. Fett/Lipid, 100: 463-471.
32. Yankah, V. V. and Akoh, C. C. 2000. Lipase-catalyzed Acidolysis of Tristearin with Oleic or Caprylicacids to Produce Structured Lipids. J. Am. Oil Chem. Soc., 77: 495–500.
33. Zhao, H., Lu, Z., Bie, X., Lu, F. and Liu, Z. 2007. Lipase Catalyzed Acidolysis of Lard with Capric Acid in Organic Solvent. J. Food Eng., 78: 41-46.
33. Zhou, D., Xu, X., Mu, H., Hoy, C. E. and Adler-Nissen, J. 2001. Synthesis of Structured Triacylglycerols Containing Caproic Acid by Lipase-catalyzed Acidolysis: Optimization by Response Surface Methodology. J. Agric. Food Chem., 49: 5771-5777.
Journal of Agricultural Science and Technology
Volume 14, Issue 6
November and December 2012
Pages 1297-1310