Skip to main content
Log in

Immobilized Talaromyces thermophilus lipase as an efficient catalyst for the production of LML-type structured lipids

  • Research Paper
  • Published:
Bioprocess and Biosystems Engineering Aims and scope Submit manuscript

Abstract

LML-type structured lipids are one type of medium- and long-chain triacylglycerols. LML was synthesized using immobilized Talaromyces thermophilus lipase (TTL)-catalyzed interesterification of tricaprylin and ethyl linoleate. The resin AB-8 was chosen, and the lipase/support ratio was determined to be 60 mg/g. Subsequently, the immobilized TTL with strict sn-1,3 regiospecificity was applied to synthesize LML. Under the optimized conditions (60 °C, reaction time 6 h, enzyme loading of 6% of the total weight of substrates, substrate of molar ratio of ethyl linoleate to tricaprylin of 6:1), Triacylglycerols with two long- and one medium-chain FAs (DL-TAG) content as high as 52.86 mol% was obtained. Scale-up reaction further verified the industrial potential of the established process. The final product contained 85.24 mol% DL-TAG of which 97 mol% was LML after purification. The final product obtained with the high LML content would have substantial potential to be used as functional oils.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

Abbreviations

TTL:

Talaromyces thermophilus lipase

TAG:

Triacylglycerol

FA:

Fatty acid

MAG:

Monoacylglycerol

DAG:

Diacylglycerol

References

  1. St-Onge MP, Jones PJH (2002) Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity. J Nutr 132:329–332

    Article  CAS  PubMed  Google Scholar 

  2. Zhao HZ, Lu ZX, Bie XM, Lu FX, Liu ZM (2007) Lipase catalyzed acidolysis of lard with capric acid in organic solvent. J Food Eng 78:41–46

    Article  CAS  Google Scholar 

  3. Marten B, Pfeuffer M, Schrezenmeir J (2006) Medium-chain triglycerides. Int Dairy J 16:1374–1382

    Article  CAS  Google Scholar 

  4. Lu JY, Jin QZ, Wang XG, Wang XS (2017) Preparation of medium and long chain triacylglycerols by lipase-catalyzed interesterification in a solvent-free system. Process Biochem 54:89–95

    Article  CAS  Google Scholar 

  5. Matulka RA, Noguchi O, Nosaka N (2006) Safety evaluation of a medium- and long-chain triacylglycerol oil produced from medium-chain triacylglycerols and edible vegetable oil. Food Chem Toxicol 44:1530–1538

    Article  CAS  PubMed  Google Scholar 

  6. Koh SP, Tan CP, Lai OM, Arifin N, Yusoff MSA, Long K (2010) Enzymatic synthesis of medium- and long-chain triacylglycerols (MLCT): optimization of process parameters using response surface methodology. Food Bioprocess Techol 3:288–299

    Article  CAS  Google Scholar 

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

    Google Scholar 

  8. Zhou S, Wang Y, Jiang Y, Yu LL (2017) Safety assessment of medium- and long-chain triacylglycerols containing 30%(w/w) medium-chain fatty acids in mice and rats. Regul Toxicol Phar 86:42–48

    Article  CAS  Google Scholar 

  9. Costa CM, Osório NM, Canet A, Rivera I, Sandoval G, Valero F, Ferreira-Dias S (2018) Production of MLM type structured lipids from grapeseed oil catalyzed by non-commercial lipases. Eur J Lipid Sci Technol 120:1700320

    Article  CAS  Google Scholar 

  10. Mu H, Porsgaard T (2005) The metabolism of structured triacylglycerols. Prog Lipid Res 44:430–448

    Article  CAS  PubMed  Google Scholar 

  11. Morales-Medina R, Munio M, Guadix A, Guadix EM (2017) Development of an up-grading process to produce MLM structured lipids from sardine discards. Food Chem 228:634–642

    Article  CAS  PubMed  Google Scholar 

  12. Babayan VK (1987) Medium chain triglycerides and structured lipids. Lipids 22:417–420

    Article  CAS  PubMed  Google Scholar 

  13. Bach AC, Ingenbleek Y, Frey A (1996) The usefulness of dietary medium-chain triglycerides in body weight control: fact or fancy? J Lipid Res 37:708–726

    CAS  PubMed  Google Scholar 

  14. Lu J, Jin QZ, Wang XG, Wang XS (2017) Preparation of medium and long chain triacylglycerols by lipase-catalyzed interesterification in a solvent-free system. Process Biochem 54:89–95

    Article  CAS  Google Scholar 

  15. Gudmundsdottir AV, Hansen KA, Magnusson CD (2015) Synthesis of reversed structured triacylglycerols possessing EPA and DHA at their terminal positions. Tetrahedron 71:8544–8550

    Article  CAS  Google Scholar 

  16. Kawashima A, Shimada Y, Yamamoto M, Sugihara A, Nagao T, Komemushi S, Tominaga Y (2001) Enzymatic synthesis of high-purity structured lipids with caprylic acid at 1, 3-positions and polyunsaturated fatty acid at 2-position. J Am Oil Chem Soc 78:611–616

    Article  CAS  Google Scholar 

  17. Zhao XY, Wang XD, Liu X, Zhu WJ, Mei YY, Li WW, Wang J (2015) Structured lipids enriched with unsaturated fatty acids produced by enzymatic acidolysis of silkworm pupae oil using oleic acid. Eur J Lipid Sci Technol 117:879–889

    Article  CAS  Google Scholar 

  18. Zhao HZ, Lu ZX, Lu FX, Bie XM, Liu ZM, Zeng XX (2006) Lipase-catalysed acidolysis of lard with caprylic acid to produce structured lipid. Int J Food Sci Technol 41:1027–1032

    Article  CAS  Google Scholar 

  19. Khodadadi M, Kermasha S (2014) Modeling lipase-catalyzed interesterification of flaxseed oil and tricaprylin for the synthesis of structured lipids. J Mol Catal B-Enzym 102:33–40

    Article  CAS  Google Scholar 

  20. Nunes PA, Pires-Cabral P, Guillén M, Valero F, Ferreira-Dias S (2012) Optimized production of MLM triacylglycerols catalyzed by immobilized heterologous Rhizopus oryzae lipase. J Am Oil Chem Soc 89:1287–1295

    CAS  Google Scholar 

  21. Chen B, Zhang H, Cheong LZ, Tan T, Xu X (2012) Enzymatic production of ABA-type structured lipids containing omega-3 and medium-chain fatty acids: effects of different acyl donors on the acyl migration rate. Food Bioprocess Technol 5:541–547

    Article  CAS  Google Scholar 

  22. Romdhane IBB, Fendri A, Gargouri Y, Gargouri A, Belghith H (2010) A novel thermoactive and alkaline lipase from Talaromyces thermophilus fungus for use in laundry detergents. Biochem Eng J 53:112–120

    Article  CAS  Google Scholar 

  23. Romdhane IBB, Frikha F, Maalej-Achouri I, Gargouri A, Belghith H (2012) Gene cloning and molecular characterization of the Talaromyces thermophilus lipase catalyzed efficient hydrolysis and synthesis of esters. Gene 494:112–118

    Article  CAS  PubMed  Google Scholar 

  24. Romdhane IBB, Romdhane ZB, Bouzid M, Gargouri A, Belghith H (2013) Application of a chitosan-immobilized Talaromyces thermophilus lipase to a batch biodiesel production from waste frying oils. Appl Biochem Biote 171:1986–2002

    Article  CAS  Google Scholar 

  25. Wang XM, Li DM, Qu M, Durrani R, Yang B, Wang YH (2017) Immobilized MAS1 lipase showed high esterification activity in the production of triacylglycerols with n-3 polyunsaturated fatty acids. Food Chem 216:260–267

    Article  CAS  PubMed  Google Scholar 

  26. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254

    Article  CAS  PubMed  Google Scholar 

  27. Li DM, Qin XL, Wang JR, Yang B, Wang WF, Huang WL, Wang YH (2015) Hydrolysis of soybean oil to produce diacylglycerol by a lipase from Rhizopus oryzae. J Mol Catal B-Enzym 115:43–50

    Article  CAS  Google Scholar 

  28. Ota Y, Itabashi Y, Hasuo M (1996) Measurement of positional specificity index of microbial lipases by chiral phase high-pressure liquid chromatography. Biosci Biotechnol Biochem 60:145–146

    Article  CAS  Google Scholar 

  29. Sahin N, Akoh CC, Karaali A (2005) Lipase-catalyzed acidolysis of tripalmitin with hazelnut oil fatty acids and stearic acid to produce human milk fat substitutes. J Agric Food Chem 53:5779–5783

    Article  CAS  PubMed  Google Scholar 

  30. Wang YH, Mai QY, Qin XL, Yang B, Wang ZL, Chen HT (2009) Establishment of an evaluation model for human milk fat substitutes. J Agric Food Chem 58:642–649

    Article  CAS  Google Scholar 

  31. Li DM, Wang WF, Qin XL, Li XX, Yang B, Wang YH (2016) A novel process for the synthesis of highly pure n-3 polyunsaturated fatty acid (PUFA)-enriched triglycerides by combined transesterification and ethanolysis. J Agric Food Chem 64:6533–6538

    Article  CAS  PubMed  Google Scholar 

  32. Basso A, Froment L, Hesseler M, Serban S (2013) New highly robust divinyl benzene/acrylate polymer for immobilization of lipase CALB. Eur J Lipid Sci Technol 115:468–472

    Article  CAS  Google Scholar 

  33. Cai CS, Gao YQ, Liu Y, Zhong NJ, Liu N (2016) Immobilization of Candida antarctica lipase B onto SBA-15 and their application in glycerolysis for diacylglycerols synthesis. Food Chem 212:205–212

    Article  CAS  PubMed  Google Scholar 

  34. Li DM, Wang WF, Liu PZ, Xu L, Faiza M, Yang B, Wang YH (2017) Immobilization of Candida antarctica lipase B onto ECR1030 resin and its application in the synthesis of n-3 PUFA-rich triacylglycerols. Eur J Lipid Sci Technol 119:1700266

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Outstanding Youth Science Foundation of China (31725022), Molecular Enzyme and Engineering International Cooperation Base of South China University of Technology (2017A050503001), Special Program of Guangdong Province for Leader Project in Science and Technology Innovation: Development of New Partial Glycerin Lipase (2015TX01N207), and Science and Technology Planning project of Guangdong province (2016B090920082).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yonghua Wang.

Ethics declarations

Conflict of interest

The authors have declared no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lian, W., Wang, W., Tan, C.P. et al. Immobilized Talaromyces thermophilus lipase as an efficient catalyst for the production of LML-type structured lipids. Bioprocess Biosyst Eng 42, 321–329 (2019). https://doi.org/10.1007/s00449-018-2036-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00449-018-2036-7

Keywords

Navigation