Enzymatic modification of diacylglycerol with different type of fatty acids

지방산 종류에 따른 Diacylglycerol의 효소적 개질 연구

  • Lee, Mi-Young (Chungcheongnam-do Health and Environmental Research Institute) ;
  • Hong, Soon-Taek (Department of Food Science and Technology, Chungnam National University) ;
  • Lee, Ki-Teak (Department of Food Science and Technology, Chungnam National University)
  • Received : 2014.05.26
  • Accepted : 2014.06.23
  • Published : 2014.06.30


Diacylglycerol-oil (DAG oil) and four kinds of fatty acids [C16:0, C18:0, perillar oil-hydrolyzate(C18:3, 59.7%) and docosahexaenoic acid(DHA, C22:6, 63.7%)] were enzymatically esterified with 1:0.5, 1:1 and 1:1.5 molar ratio (DAG oil: fatty acids) to produce structured DAG. The reaction mixture were catalyzed by addition of sn-1,3 specific Lipozyme RMIM with 10 wt% of total substrates, and reacted for 1, 3, 6 and 24 hr at $62^{\circ}C$ with 220 rpm on the shaking water bath. The produced DAG were analyzed by TLC. In the result, the proportion of each fatty acid [(C16:0, C18:0, perilla oil-hydrolysate(C18:3, 59.7%) and DHA(C22:6, 63.7%)] on DAG products were increased as molar ratios of substrate increased. Among them, DHA showed the least reaction rate in which 24.2 % of DHA was found in the structured DAG molecules after 24 hr reaction with 1:1.5 molar substrate amount ratio.


  1. Cho EJ, Cho KH, Lee KT. 2005. Compositional changes of functional oil from algae oil during the lipase-catalyzed production. Journal of the Korean Society of Food Science and Nutrition 34(7):1059-1063. [in Korean]
  2. Fomuso LB, Akoh CC. 2002. Lipase-catalyzed acidolysis of olive oil and caprylic acid in a bench-scale packed bed bioreactor. Food Research International 35(1):15-21.
  3. Fujii A, Allen TJ, Nestel PJ. 2007. A 1,3-diacylglycerol-rich oil induces less atherosclerosis and lowers plasma cholesterol in diabetic apoE-deficient mice. Atherosclerosis 193:55-61.
  4. Jeon MS, Lee CR, Lee KT. 2010. Production of diacylglycerol from lipase by the catalyzed reaction of soybean oil and glyceryl monoleate. Korean Journal of Food Science and Technology 42(2):246-249. [in Korean]
  5. Kristensen JB, Xu X, Mu H. 2005. Diacylglycerol synthesis by enzymatic glycerolysis: Screening of commercially available lipases. Journal of the American Oil Chemists' Society 82(5): 329-334.
  6. Kristensen JB, Nielsen NS, Jacobsen C, Mu H. 2006. Oxidative stability of diacylglycerol oil and butter blends containing diacylglycerols. European Journal of Lipid Science and Technology 108:336-350.
  7. Korea Food and Drug Administration. 2011. NLS Standard Operating Procedure Analytical Methods. Osong, Korea.
  8. Mu H, Xu X, Hoy CE. 1998. Production of specific-structured triacylglycerols by lipase-catalyzed interesterification in a laboratory scale continuous reactor. Journal of the American Oil Chemists' Society 75(9):1187-1193.
  9. Park RK, Lee KT. 2004. Synthesis and characterization of mono- and diacylglycerol enriched functional oil by enzymatic glycerolysis of corn oil. Korean Journal of Food Science and Technology 36(2):211-216. [in Korean]
  10. Poisson L, Devos M, Godet S, Ergan F, Pencreac'h G. 2009. Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): An enzymatic approach for evidence and study. Biotechnology Letters 31:743-749.
  11. Shin JA, Lee KT. 2010. Production and application of structured lipids. Food Science and Industry 43(4):14-23. [in Korean]
  12. Xu X, Skands ARH, Hoy CE, Mu H, Balchen S, Nissen JA. 1998. Production of specific-structured lipids by enzymatic interesterification: Elucidation of acyl migration by response surface design. Journal of the American Oil Chemists' Society 75(9):1179-1186.
  13. Yamamoto K, Asakawa H, Tokunaga K, Watanabe H, Matsuo N, Tokimitsu I, Yagi N. 2001. Long-term ingestion of dietary diacylglycerol lowers serum triacylglycerol in type II diabetic patients with hypertriglyceridemia. Journal of Nutrition 131:3204-3207.