Skip to main content
SpringerLink
Log in

What Is The Importance of Structured Triglycerides and Diglycerides?

  • Chapter
  • First Online:
Enzymatic Synthesis of Structured Triglycerides

Part of the book series: SpringerBriefs in Molecular Science ((BRIEFSMOLECULAR))

Abstract

This chapter reviews several important aspects of structured triglycerides (STs) and diglycerides (SDs), with the most updated literature on the topic. STs and SDs are synthesized to achieve some specific metabolic effects or to enhance physical–chemical properties of fats and oils. They comprise cocoa butter equivalents, human milk fat substitutes, low-calorie fats and oils, health-beneficial fatty acid-rich fats/oils, or diglyceride oil, and margarines or other plastic fats. A review of the metabolic fate of triglycerides and the health and nutritional properties of structured tri and diglycerides is presented.

Structured triglycerides can be synthesized by diverse routes, depending on the sort of triglycerides and the nature of the substrate. Several approaches to the productions of STs and SDs are described briefly including chemical and enzymatic interesterification (involving acidolysis and glycerolysis), hydrolysis and esterification.

In addition, the consumer market for structured di- and triglycerides is revised.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Akoh CC (2002) Structured lipids. In: Akoh CC, Min DB (eds) Food lipids. Marcel Dekker, New York, pp 877–908

    Chapter  Google Scholar 

  2. Akoh CC, Moussata CO (1998) Lipase-catalysed modification of borage oil: incorporation of capric and eicosapentanoic acids to form a strutured lipid. J Am Oil Chem Soc 75:697–701

    Article  CAS  Google Scholar 

  3. Lai O, Lo S-K (2011) Diacylglycerol oils: nutritional aspects and applications in foods. In: Talbot G (ed) reducing saturated fats in foods. Woodhead, Cambridge, pp 158–178

    Chapter  Google Scholar 

  4. Eichmann T, Lass A (2015) DAG tales: the multiple faces of diacylglycerol-stereochemistry, metabolism, and signaling. Cell Mol Life Sci 72:3931–3952

    Article  CAS  Google Scholar 

  5. Palmquist DL, Lock AL, Shingfield KJ, Bauman DE (2005) Biosynthesis of conjugated linoleic acid in ruminants and humans. In: Taylor SL (ed) Advances in food and nutrition research, vol 50. Elsevier, San Diego, pp 179–217

    Chapter  Google Scholar 

  6. Hamosh M, Burns W (1977) Lipolytic activity of human lingual glands (Ebner). Lab Invest 37:603–606

    CAS  Google Scholar 

  7. Hamosh M (1978) Rat lingual lipase. Factors affecting enzyme activity and secretion. Am J Physiol 235:416–421

    Google Scholar 

  8. Gargouri Y, Moreau H, Pieroni G, Verger R (1988) Human gastric lipase: a sulfhydryl enzyme. J Biol Chem 263:2159–2162

    CAS  Google Scholar 

  9. Small DM (1991) The effects of glyceride structure on absorption and metabolism. Annu Rev Nutr 11:412–434

    Article  Google Scholar 

  10. Brody T (1999) Nutritional biochemistry, 2nd edn. Academic, San Diego, p 320

    Google Scholar 

  11. Merolli A (1997) Medium-chain lipids: new sources and uses. Inform 8:597–603

    Google Scholar 

  12. Kubow S (1998) The influence of stereospecific saturated fatty acids in dietary triacylglycerols on lipoprotein metabolism. In: Christophe AB (ed) Structural modified food fats: synthesis, biochemistry, and use. AOCS, Champaign, pp 149–159

    Google Scholar 

  13. Carey M, Hernell OF (1992) Digestion and absorption of fats. Semin Gastrointest Dis 4:189–208

    Google Scholar 

  14. Mu H, Hoy CE (2004) The digestion of dietary triacylglycerols. Prog. Lipid Res. 43:105–133

    Article  CAS  Google Scholar 

  15. Fats and oils in human nutrition (1993) Report of a joint expert consultation, FAO food and nutrition paper (FAO) 57. http://www.fao.org/docrep/v4700e/v4700e08.htm

  16. Vasudevan DM, Sreekumari S, Vaidyanathan K (eds) (2013) Textbook of biochemistry for medical students. JP Medical Ltd, New Delhi

    Google Scholar 

  17. Havlicekova Z, Jesenak M, Banovcin P, Kuchta M (2016) Beta-palmitate a natural component of human milk in supplemental milk formulas. Nutr J 15:28. doi:10.1186/s12937-016-0145-1

    Article  Google Scholar 

  18. Breckenridge WC, Marai L, Kuksis A (1969) Triglyceride structure of human milk fat. Can J Biochem 47:761–769

    Article  CAS  Google Scholar 

  19. Jensen RG (1999) Lipids in human milk. Lipids 34:1243–1271

    Article  CAS  Google Scholar 

  20. Bar-Yoseph F, Lifshitz Y, Cohen T (2013) Review of sn-2 palmitate oil implications for infant health. Prostaglandins Leukot Essent Fatty Acids 89:139–143

    Article  CAS  Google Scholar 

  21. Innis SM (2011) Dietary triacylglycerol structure and its role in infant nutrition. Adv. Nutr 2:275–283

    Article  CAS  Google Scholar 

  22. O’Shea M, Gerristen J, Mohede I (2006) Clinical benefits of a structured lipid (Betapol™) in infant formula. In: Akoh CC (ed) Handbook of functional lipids. Taylor & Francis, Boca Raton, pp 261–278

    Google Scholar 

  23. Marten B, Pfeuffer M, Schrezenmeir J (2006) Review—medium-chain triglycerides. Int Dairy J 16:1374–1382

    Article  CAS  Google Scholar 

  24. Mumme K, Stonehouse W (2015) Effects of medium-chain triglycerides on weight loss and body composition: a meta-analysis of randomized controlled trials. J Acad Nutr Diet 115:249–263

    Article  Google Scholar 

  25. Huang C, Altimova Y, Myers T, Ebersole J (2011) Short- and medium-chain fatty acids exhibit antimicrobial activity for oral microorganisms. Arch Oral Biol 56:650–654

    Article  CAS  Google Scholar 

  26. Lee YY, Tang TK, Lai OM (2012) Health benefits, enzymatic production, and application of medium- and long-chain triacylglycerol (MLCT) in food industries: a review. J Food Sci 77:137–144

    Article  Google Scholar 

  27. Pande G, Akoh CC (2012) Structured lipids in nutraceutical formulations. Inform 23:50–64

    Google Scholar 

  28. Picq M, Bernoud-Hubac N, Lagarde M (2013) Synthesis and biological interest of structured docosahexaenoic acid-containing triacylglycerols and phospholipids. Curr Org Chem 17:841–847

    Article  CAS  Google Scholar 

  29. Wu G, Zaniolo O, Schuster H, Schlotzer E, Pradelli L (2016) Structured triglycerides versus physical mixtures of medium- and long-chain triglycerides for parenteral nutrition in surgical or critically ill adult patients: Systematic review and meta-analysis. Clin Nutr. doi:10.1016/j.clnu.2016.01.004

    Google Scholar 

  30. WHO Fact Sheet No: 311 (2015). Overweight and obesity. Updated January 2015

    Google Scholar 

  31. Hou CT (2005) Handbook of industrial biocatalysis. Taylor & Francis, Boca Raton

    Book  Google Scholar 

  32. Auerbach MH, Chang PW, Kosmark R, O’Neill JJ, Philips JC, Klemann LP (1998) Salatrim: a family of reduced-calorie structured lipids. In: Christophe AB (ed) Structural modified food fats: synthesis, biochemistry, and use. AOCS, Champaign, pp 89–116

    Chapter  Google Scholar 

  33. Wiley (2007) Kirk-othmer food and feed technology, vol 1. Wiley, New York

    Google Scholar 

  34. Kadivar S, De Clercq N, Van de Walle D, Dewettinck K (2014) Optimisation of enzymatic synthesis of cocoa butter equivalent from high oleic sunflower oil. J Sci Food Agric 94:1325–1331

    Article  CAS  Google Scholar 

  35. Smith KW (2015) Structured triacylglycerols: Properties and processing for use in food. In: Talbot G (ed) Specialty oils and fats in food and nutrition. Woodhead, Cambridge, pp 207–218

    Chapter  Google Scholar 

  36. Macrae, AR, How P (1983) Interesterification with lipase enzymes as interesterification catalyst. Unilever PLC Unilever NV, International Patent Application WO83/03844

    Google Scholar 

  37. Mohamed I (2015) Enzymatic synthesis of cocoa butter equivalent from olive oil and palmitic-stearic fatty acid mixture. Appl Biochem Biotechnol 175:757–769

    Article  CAS  Google Scholar 

  38. Zang X, Xie W (2014) Enzymatic interesterification of soybean oil and methyl stearate blends using lipase immobilized on magnetic Fe3O4/SBA-15 composites as a biocatalyst. J Oleo Sci 63:1027–1034

    Article  CAS  Google Scholar 

  39. Momeny E, Vafaei N, Ramli N (2013) Physicochemical properties and antioxidant activity of a synthetic cocoa butter equivalent obtained through modification of mango seed oil. Int J Food Sci Technol 48:1549–1555

    Article  CAS  Google Scholar 

  40. Klonoff D (2007) Replacements for trans fats—will there be an oil shortage? J Diabetes Sci Technol 1:415–422

    Article  Google Scholar 

  41. Tang L, Hu J, Zhu X, Luo L, Lei L, Deng Z, Lee K (2012) Enzymatic interesterification of palm stearin with Cinnamomum camphora seed oil to produce zero-trans medium-chain triacylglycerols-eriched plastic fat. J Food Sci 77:454–460

    Article  Google Scholar 

  42. Yuan Q, Ramprasath V, Harding S, Rideout T, Chan Y, Jones P (2010) Diacylglycerol oil reduces body fat but does not alter energy or lipid metabolism in overweight, hypertriglyceridemic women. J Nutr 140:1122–1126

    Article  CAS  Google Scholar 

  43. Hibi M, Sugiura Y, Yokoyama R, Takase H, Shiiba D, Meguro S, Katashima M, Shimizu A, Tokimitsu I (2011) The short-term effect of diacylglycerol oil consumption on total and dietary fat utilization in overweight women. Obesity (Silver Spring) 19:536–540

    Article  CAS  Google Scholar 

  44. Saito S, Yamaguchi T, Shoji K, Hibi M, Sugita T, Takase H (2010) Effect of low concentration of diacylglycerol on mildly postprandial hypertriglyceridemia. Atherosclerosis 213:539–544

    Article  CAS  Google Scholar 

  45. Jandacek R (2007) Commercial applications of fats in foods. In: Chow C (ed) Fatty acids in foods and its health implications, 3rd edn. CRC, Boca Raton, pp 473–492

    Google Scholar 

  46. Kristensen J, Jørgensen H, Mu H (2006) Diacylglycerol oil does not affect portal vein transport of nonesterified fatty acids but decreases the postprandial plasma lipid response in catheterized pigs. J Nutr 136:1800–1805

    CAS  Google Scholar 

  47. Arab-Tehrany E, Jacquot M, Gaiani C, Imran M, Desobry S, Linder M (2012) Beneficial effects and oxidative stability of omega-3 long-chain polyunsaturated fatty acids. Trends Food Sci Technol 25:24–33

    Article  CAS  Google Scholar 

  48. Rousseau D, Marangoni A (2008) Chemical interesterification of food lipids: theory and practice. In: Akoh C, Min D (eds) Food lipids: chemistry, nutrition, and biotechnology, 3rd edn. CRC, Boca Raton, pp 267–295

    Google Scholar 

  49. Gibon V (2011) Enzymatic interesterification of oils. Lipid Technol 23:274–277

    Article  CAS  Google Scholar 

  50. Kim B, Akoh C (2015) Recent research trends on the enzymatic synthesis of structured lipids. J Food Sci 80:1713–1724

    Article  Google Scholar 

  51. Phuah ET, Tang TK, Lee YY, Choong T, Tan CP, Lai OM (2015) Review on the current state of diacylglycerol production using enzymatic approach. Food Bioprocess Technol 8:1169–1186

    Article  Google Scholar 

  52. Pedersen Voll F, Zanette A, Ferreira Cabral V, Dariva C, Mendonça Alves De Souza R, Cardozo Filho L, Corazza M (2012) Kinetic modeling of solvent-free lipase-catalyzed partial hydrolysis of palm oil. Appl Biochem Biotechnol 169:1121–1142

    Article  Google Scholar 

  53. Song Z, Liu Y, Jin Q, Li L, Wang X, Huang J, Liu R (2012) Lipase-catalyzed preparation of diacylglycerol-enriched oil from high-acid rice bran oil in solvent-free system. Appl Biochem Biotechnol 168:364–374

    Article  CAS  Google Scholar 

  54. Zhong N, Gui Z, Xu L, Huang J, Hu K, Gao Y, Xu Z, Su J, Li B (2013) Solvent-free enzymatic synthesis of 1,3-diacylglycerols by direct esterification of glycerol with saturated fatty acids. Lipids Health Dis 12:65–71

    Article  CAS  Google Scholar 

  55. Duan ZQ, Fang XL, Wang ZY, Bi YH, Sun H (2015) Sustainable process for 1,3-diolein synthesis catalyzed by immobilized lipase from Penicillium expansum. ACS Sustain Chem Eng 3:2804–2808

    Article  CAS  Google Scholar 

  56. Dhara R, Singhal R (2014) Process optimization of enzyme catalyzed production of dietary diacylglycerol (DAG) using TLIM as biocatalyst. J Oleo Sci 63:169–176

    Article  CAS  Google Scholar 

  57. Monte Blanco SFM, Santos JS, Feltes MMC, Dors G, Licodiedoff S, Lerin LA, de Oliveira D, Ninow JL, Furigo A Jr (2015) Optimization of diacylglycerol production by glycerolysis of fish oil catalyzed by Lipozyme TL IM with Tween 65. Bioprocess Biosyst Eng 38:2379–2388

    Article  CAS  Google Scholar 

  58. de Deckere EAM, Verschuren PM (2000) Functional fats and spreads. In: Gibson G, Williams C (eds) Functional foods—concept to product. Woodhead, Cambridge, pp 233–257

    Google Scholar 

  59. Yoon SH (2006) Potential market for functional lipids. In: Akoh CC (ed) Handbook of functional lipids. Taylor & Francis, Boca Raton, pp 475–488

    Google Scholar 

  60. Guo M (2009) Functional foods, principles and technology. Woodhead, Cambridge

    Book  Google Scholar 

  61. Global Functional Food and Nutraceuticals Market (2014-2020) http://www.researchandmarkets.com/research/33gvv3/global_functional

  62. Dutra de Barcellos M, Laitano Lionello R (2011) Consumer market for functional foods in South Brazil. Int J Food System Dynamics 2:126–144

    Google Scholar 

  63. Functional Food Ingredients Market—Global Forecast to 2020 (2015) Report code: FB 3559 http://www.marketsandmarkets.com/Market-Reports/functional-food-ingredients-market-9242020.html

  64. Akoh C (2007) Fat-based fat substitutes. In: Chow C (ed) Fatty acids in foods and its health implications, 3rd edn. CRC, Boca Raton, pp 461–471

    Chapter  Google Scholar 

  65. Watkins C (2009) Kao suspends DAG oil shipments. Inform 20:689–690

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. PLAPIQUI-UNS-CONICET, Buenos Aires, Argentina

    María Luján Ferreira & Gabriela Marta Tonetto

Authors
  1. María Luján Ferreira
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gabriela Marta Tonetto
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 2017 The Author(s)

About this chapter

Cite this chapter

Ferreira, M.L., Tonetto, G.M. (2017). What Is The Importance of Structured Triglycerides and Diglycerides?. In: Enzymatic Synthesis of Structured Triglycerides. SpringerBriefs in Molecular Science. Springer, Cham. https://doi.org/10.1007/978-3-319-51574-8_1

Download citation

Publish with us

Policies and ethics

Search

Navigation