Enzymatic synthesis of structured lipids with behenic acid at the sn-1, 3 positions of triacylglycerols
A long chain saturated fatty acid (SFA), behenic acid, is incorporated into the sn-1, 3 positions of triacylglycerols in palm olein (POo) and high-oleic sunflower oil (HOS) by solvent-free interesterification catalyzed by Lipozyme RM IM. The enzymatic interesterified HOS (EIE-HOS) yielded 76.5% of BOO and BOB as compared to 45.6% in POo (EIE-POo). The sn-2 position of EIE-HOS displayed 5.3 mol% of SFA which is significantly lower compared to 13.5 mol% in EIE-POo (P < 0.001). The sn-1, 3 positions of EIE-POo exhibited greater amount of behenic acid (82.0 mol%) in relation to EIE-HOS (64.0 mol%) (P < 0.001). Due to the greater variety of constitutive triacylglycerol, EIE-POo showed greater differences between onset (To) and offset temperature (Tf) in the melting endotherms (76.99 °C) as compared to EIE-HOS (68.65 °C), and may offer more intensive cooling sensation and flavor release.
KeywordsEnzymatic interesterification reaction Structured lipids Behenic acid sn-1, 3 positions Lipozyme RM IM
The present study was supported by University of Malaya, Kuala Lumpur, Malaysia, through University Malaya Research Grant (RG274-14AF) and Malaysian Ministry of Education’s Fundamental Research Grant Scheme (FRGS) (FP023-2014B). The authors have no conflicts of interest to declare.
- 8.World Health Organization. Obesity and overweight. Available from: http://www.who.int/mediacentre/factsheets/fs311/en/ Accessed Jun. 27, 2013
- 15.Kaimal TNB, Kanjilal S, Prasad RBN. Enzymatic process for preparing reduced calorie fats containing behenic acid. U.S. Patent, 6, 617, 141 (2003)Google Scholar
- 16.Kojima M, Tachibana N, Yamahira T, Seino S, Izumisawa A, Sagi N, Arishima T, Kohno M, Takamatsu K, Hirotsuka M, Ikeda I. Structured triacylglycerol containing behenic and oleic acids suppresses triacylglycerol absorption and prevents obesity in rats. Lipids Health Dis. 9: 77–82 (2010)CrossRefGoogle Scholar
- 20.Christie WW. Gas Chromatography and Lipids: A Practical Guide. 3rd ed. The Oily Press Ltd, Ayr, Scotland. pp. 11–42 (1989)Google Scholar
- 21.AOCS. The Official Methods and Recommended Practices of the AOCS. 3rd ed. Method Cj 1-94. American Oil Chemists’ Society, Champaign, Illinois, USA, (1988)Google Scholar
- 22.AOCS. The Official Methods and Recommended Practices of the AOCS. 5th ed. Method Cc 3-25. American Oil Chemists’ Society, Champaign, Illinois, USA, (1997)Google Scholar
- 23.IUPAC. Standard Methods for the Analysis of Oils, Fats and Derivatives. 7th ed. Solid Fat Content 2.150(a) test method. International Union for Pure and Applied Chemistry, Oxford, UK (1986)Google Scholar
- 29.Renaud SC, Ruf JC, Petithory D. The positional distribution of fatty acids in palm oil and lard influences their biologic effects in rats. J. Nutr. 125: 229–237 (1995)Google Scholar
- 30.Arifin N, Cheong LZ, Koh SP, Long K, Tan CP, Yusoff MSA, Aini IN, Lo SK, Lai OM. Physicochemical properties and sensory attributes of medium and long-chain triacylglycerols (MLCT)-enriched bakery shortening. Food Bioprod. Process. 4: 587–596 (2011)Google Scholar