Food Science and Biotechnology

, Volume 27, Issue 2, pp 353–366 | Cite as

Enzymatic synthesis of structured lipids with behenic acid at the sn-1, 3 positions of triacylglycerols

Article
  • 34 Downloads

Abstract

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.

Keywords

Enzymatic interesterification reaction Structured lipids Behenic acid sn-1, 3 positions Lipozyme RM IM 

Notes

Acknowledgements

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.

References

  1. 1.
    Foresti ML, Ferreira ML. Lipase-catalyzed acidolysis of tripalmitin with capric acid in organic solvent medium: Analysis of the effect of experimental conditions through factorial design and analysis of multiple responses. Enzyme Microb. Technol. 46: 419–429 (2010)CrossRefGoogle Scholar
  2. 2.
    Arifin N, Koh SP, Long K, Tan CP, Yusoff MSA, Lai OM. Modeling and optimization of Lipozyme RM IM-catalyzed esterification of medium- and long-chain triacylglycerols (MLCT) using response surface methodology. Food Bioprocess Tech. 5: 216–225 (2010)CrossRefGoogle Scholar
  3. 3.
    Palla CA, Carrín ME. Kinetics modeling of the acidolysis with immobilized Rhizomucor miehei lipases for production of structured lipids from sunflower oil. Biochem. Eng. J. 90: 184–194 (2014)CrossRefGoogle Scholar
  4. 4.
    Ifebuda EA, Akoh CC. Modification of stearidonic acid soybean oil by immobilized Rhizomucor miehei lipase to incorporate caprylic acid. J. Am. Oil Chem. Soc. 91: 953–965 (2014)CrossRefGoogle Scholar
  5. 5.
    Han L, Xu ZJ, Huang JH, Meng Z, Liu YF, Wang XG. Enzymatically catalyzed synthesis of low-calorie structured lipid in a solvent-free system: optimization by response surface methodology. J. Agric. Food Chem. 59: 12635–12642 (2011)CrossRefGoogle Scholar
  6. 6.
    Wang YY, Xia L, Xu XB, Xie L, Duan ZQ. Lipase-catalyzed acidolysis of canola oil with caprylic acid to produce medium-, long- and medium-chain-type structured lipids. Food Bioprod. Process. 90: 707–712 (2012)CrossRefGoogle Scholar
  7. 7.
    Osborn HT, Akoh CC. Structured lipids- Novel fats with medical, nutraceutical, and food applications. Compr. Rev. Food Sci. F. 1: 110–120 (2002)CrossRefGoogle Scholar
  8. 8.
    World Health Organization. Obesity and overweight. Available from: http://www.who.int/mediacentre/factsheets/fs311/en/ Accessed Jun. 27, 2013
  9. 9.
    Akoh CC, Yee LN. Enzymatic synthesis of position-specific low-calorie structured lipids. J. Am. Oil Chem. Soc. 74: 1409–1413 (1997)CrossRefGoogle Scholar
  10. 10.
    Yang TH, Jang Y, Han JJ, Rhee JS. Enzymatic synthesis of low-calorie structured lipids in a solvent-free system. J. Am. Oil Chem. Soc. 78: 291–296 (2001)CrossRefGoogle Scholar
  11. 11.
    Webb DR, Sanders RA. Caprenin I. Digestion, absorption, and rearrangement in thoracic duct-cannulated rats. J. Am. Coll. Toxicol. 10: 325–340 (1991)CrossRefGoogle Scholar
  12. 12.
    Wardlaw GM, Snook JT, Park S, Patel PK, Pendley FC, Lee MS, Jandacek RJ. Relative effects on serum lipids and apolipoproteins of a caprenin-rich diet compared with diets rich in palm oil/palm-kernel oil or butter. Am. J. Clin. Nutr. 61: 535–542 (1995)CrossRefGoogle Scholar
  13. 13.
    Kanjilal S, Kaki SS, Rao BVSK, Sugasini D, Rao YP, Prasad RBN, Lokesh BR. Hypocholesterolemic effects of low calorie structured lipid on rats and rabbits fed on normal and atherogenic diet. Food Chem. 136: 259–265 (2013)CrossRefGoogle Scholar
  14. 14.
    Kanjilal S, Prasad RBN, Kaimal TNB, Ghafoorunissa, Rao SH. Synthesis and estimation of calorific value of a structured lipid-potential reduced calorie fat. Lipids. 34: 1045–1055 (1999)CrossRefGoogle Scholar
  15. 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. 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
  17. 17.
    Gouk SW, Cheng SF, Mok JSL, Ong ASH, Chuah CH. Long-chain SFA at the sn-1, 3 positions of TAG reduce body fat deposition in C57BL/6 mice. Br. J. Nutr. 110: 1987–1995 (2013)CrossRefGoogle Scholar
  18. 18.
    Stolyhwo A, Colin H, Guiochon G. Analysis of triglycerides in oils and fats by liquid chromatography with the laser light scattering detector. Anal. Chem. 57: 1342–1354 (1985)CrossRefGoogle Scholar
  19. 19.
    Gouk SW, Cheng SF, Ong ASH, Chuah CH. Rapid and direct quantitative analysis of positional fatty acids in triacylglycerols using 13C NMR. Eur. J. Lipid Sci. Tech. 114: 510–519 (2012)CrossRefGoogle Scholar
  20. 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. 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. 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. 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
  24. 24.
    Perona JS, Ruiz-Gutierrez V. Simultaneous determination of molecular species of monoacylglycerols, diacylglycerols and triacylglycerols in human very-low-density lipoproteins by reversed-phase liquid chromatography. J. Chromatogr. B. 785: 89–99 (2003)CrossRefGoogle Scholar
  25. 25.
    Fabien R, Craske JD, Wootton M. Quantitative analysis of synthetic mixtures of triacylglycerols with fatty acids from caprylic to stearic. J. Am. Oil Chem. Soc. 70: 551–554 (1993)CrossRefGoogle Scholar
  26. 26.
    Svensson J, Adlercreutz P. Effect of acyl migration in Lipozyme TL IM-catalyzed interesterification using a triacylglycerol model system. Eur. J. Lipid Sci. Tech. 113: 1258–1265 (2011)CrossRefGoogle Scholar
  27. 27.
    Berry SE. Triacylglycerol structure and interesterification of palmitic and stearic acid-rich fats: An overview and implications for cardiovascular disease. Nutr. Res. Rev. 22: 3–17 (2009)CrossRefGoogle Scholar
  28. 28.
    Kritchevsky D, Davidson LM, Weight M, Kriek NP, du Plessis JP. Influence of native and randomized peanut oil on lipid metabolism and aortic sudanophilia in the vervet monkey. Atherosclerosis, 42: 53–58 (1982)CrossRefGoogle Scholar
  29. 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. 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
  31. 31.
    Criado M, Hernández-Martín E, López-Hernández A, Otero C. Enzymatic interesterification of olive oil with fully hydrogenated palm oil: Characterization of fats. Eur. J. Lipid Sci. Tech. 110: 714–724 (2008)CrossRefGoogle Scholar
  32. 32.
    Lida HMDN, Ali AR. Physico-chemical characteristics of palm-based oil blends for the production of reduced fat spreads. J. Am. Oil Chem. Soc. 75: 1625–1631 (1998)CrossRefGoogle Scholar
  33. 33.
    Criado M, Hernández-Martín E, López-Hernández A, Otero C. Enzymatic interesterification of extra virgin olive oil with a fully hydrogenated fat: Characterization of the reaction and its products. J. Am. Oil Chem. Soc. 84: 717–726 (2007)CrossRefGoogle Scholar
  34. 34.
    Torbica A, Jovanovic O, Pajin B. The advantages of solid fat content determination in cocoa butter and cocoa butter equivalents by the Karlshamns method. Eur. Food Res. Technol. 222: 385-391 (2006)CrossRefGoogle Scholar

Copyright information

© The Korean Society of Food Science and Technology and Springer Science+Business Media B.V., part of Springer Nature 2017

Authors and Affiliations

  1. 1.Unit of Research on Lipids (URL), Department of Chemistry, Faculty of ScienceUniversity of MalayaKuala LumpurMalaysia

Personalised recommendations