Czech J. Food Sci., 2025, 43(4):291-299 | DOI: 10.17221/143/2024-CJFS

Immobilised Aspergillus niger lipase synthesises sn-1,3-dioleoyl-2-palmitoylglycerolOriginal Paper

Shanhui Chen ORCID...1, Renbin Liu1, Dong Wang1, Shiyou Li1, Zhirong Yang1
1 Lipid Biosynthetic Engineering Center (LBEC), Chengdu Skuny Biotechnology Co., Ltd., Chengdu, P.R. China

sn-1,3-Dioleoyl-2-palmitoylglycerol (OPO) is a structural triglyceride with a specific distribution of fatty acids, which is an important component of breast milk fat and which can better promote the absorption of minerals and energy in infants. In this study, a lab-made immobilised Aspergillus niger lipase (IM-ANL), which is more economical than a commercial lipase, was used for hydrolysis to produce free fatty acids (FFA) and acidolysis interesterification to produce OPO. The enzyme was used for multiple purposes, reducing the cost of enzymatic production. The optimum conditions for hydrolysis were determined by experiments: the amount of IM-ANL enzyme dosage was 3%, the reaction temperature was 45 °C, and the reaction time was 48 h. The optimum conditions for acidolysis interesterification were as follows: the amount of IM-ANL enzyme dosage was 4%, the molar ratio of tripalmitin to oleic acid was 1 : 8, the reaction temperature was 55 °C, and the reaction time was 3 h. In this study, economical palm stearin and high oleic acid sunflower seed oil were selected as reaction raw materials, and the reaction temperature was moderate, the safety risk was low, the energy consumption was reduced, the process was more economical, and the economic value of high oleic acid vegetable oil was improved, which was conducive to the further promotion of OPO production.

Keywords: lipase immobilised enzyme; hydrolysis; acidolysis; interesterification; sn-1,3-dioleoyl-2-palmitoylglycerol

Received: July 15, 2024; Revised: May 30, 2025; Accepted: June 4, 2025; Prepublished online: August 7, 2025; Published: August 31, 2025  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Chen S, Liu R, Wang D, Li S, Yang Z. Immobilised Aspergillus niger lipase synthesises sn-1,3-dioleoyl-2-palmitoylglycerol. Czech J. Food Sci. 2025;43(4):291-299. doi: 10.17221/143/2024-CJFS.
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Cai H., Li Y., Zhao M., Fu G., Lai J., Feng F. (2015): Immobilization, regiospecificity characterization and application of Aspergillus oryzae lipase in the enzymatic synthesis of the structured lipid 1,3-dioleoyl-2-palmitoylglycerol. PLOS ONE, 10: e0133857. Go to original source... Go to PubMed...
    2. Chakraborty A., Bhowal J. (2023): Bioconversion of jackfruit seed waste to fungal biomass protein by submerged fermentation. Applied Biochemistry and Biotechnology, 195: 2158-2171. Go to original source... Go to PubMed...
    3. Chen J., Zhao Y., Wu R., Yin T., You J., Hu B., Jia C., Rong J., Liu R., Zhang B., Zhao S. (2023): Changes in the quality of high-oleic sunflower oil during the frying of shrimp (Litopenaeus vannamei). Foods, 12: 1332. Go to original source... Go to PubMed...
    4. Chen Y., Liu K., Yang Z., Chang M., Wang X., Wang X. (2023): Lipase-catalyzed two-step hydrolysis for concentration of acylglycerols rich in ω-3 polyunsaturated fatty acids. Food Chemistry, 400: 134115. Go to original source... Go to PubMed...
    5. Dimitroglou M., Iliodromiti Z., Christou E., Volaki P., Petropoulou C., Sokou R., Boutsikou T., Iacovidou N. (2022): Human breast milk: The key role in the maturation of immune, gastrointestinal and central nervous systems: A narrative review. Diagnostics, 12: 2208. Go to original source... Go to PubMed...
    6. Druteika G., Sadauskas M., Malunavicius V., Lastauskiene E., Statkeviciute R., Savickaite A., Gudiukaite R. (2020): New engineered Geobacillus lipase GD-95RM for industry focusing on the cleaner production of fatty esters and household washing product formulations. World Journal of Microbiology & Biotechnology, 36: 41. Go to original source... Go to PubMed...
    7. El-Ghonemy D.H., Ali T.H., Hassanein N.M., Abdellah E.M., Fadel M., Awad, G.E.A., Abdou D.A.M. (2021): Thermo-alkali-stable lipase from a novel Aspergillus niger: statistical optimization, enzyme purification, immobilization and its application in biodiesel production. Preparative Biochemistry & Biotechnology, 51: 225-240. Go to original source... Go to PubMed...
    8. Fan X., Zhang P., Fan M., Jiang P., Leng Y. (2023): Immobilized lipase for sustainable hydrolysis of acidified oil to produce fatty acid. Bioprocess and Biosystems Engineering, 46: 1195-1208. Go to original source... Go to PubMed...
    9. Fenton T.R., Elmrayed S. (2021): The importance of reporting energy values of human milk as metabolizable energy. Frontiers in Nutrition, 8: 655026. Go to original source... Go to PubMed...
    10. Gao L., Cheng X., Yu X., Wang X., Jin Q., Wang X. (2020): Lipase-mediated production of 1-oleoyl-2-palmitoyl-3-linoleoylglycerol by a two-step method. Food Bioscience, 36: 100678. Go to original source...
    11. Ghide M.K., Yan Y. (2021): 1,3-Dioleoyl-2-palmitoyl glycerol (OPO)-Enzymatic synthesis and use as an important supplement in infant formulas. Journal of Food Biochemistry, 45: e13799. Go to original source... Go to PubMed...
    12. Ghide M.K., Li K., Wang J., Abdulmalek S.A., Yan Y. (2022): Immobilization of Rhizomucor miehei lipase on magnetic multiwalled carbon nanotubes towards the synthesis of structured lipids rich in sn-2 palmitic acid and sn-1,3 oleic acid (OPO) for infant formula use. Food Chemistry, 390: 133171. Go to original source... Go to PubMed...
    13. Hasibuan H.A., Sitanggang A.B., Andarwulan N., Hariyadi P. (2021): Enzymatic synthesis of human milk fat substitute - A review on technological approaches. Food Technology and Biotechnology, 59: 475-495. Go to original source... Go to PubMed...
    14. Innis S.M. (2011): Dietary triacylglycerol structure and its role in infant nutrition. Advances in Nutrition, 2: 275-283. Go to original source... Go to PubMed...
    15. Kallio H., Nylund M., Boström P., Yang B. (2017): Triacylglycerol regioisomers in human milk resolved with an algorithmic novel electrospray ionization tandem mass spectrometry method. Food Chemistry, 233: 351-360. Go to original source... Go to PubMed...
    16. Kumar A., Mukhia S., Kumar N., Acharya V., Kumar S., Kumar R. (2020): A broad temperature active lipase purified from a psychrotrophic bacterium of Sikkim Himalaya with potential application in detergent formulation. Frontiers in Bioengineering and Biotechnology, 8: 642. Go to original source... Go to PubMed...
    17. Li C., Zhou J., Du G., Chen J., Takahashi S., Liu S. (2020): Developing Aspergillus niger as a cell factory for food enzyme production. Biotechnology Advances, 44: 107630. Go to original source... Go to PubMed...
    18. Li Y., Zhang Y., Zhou Y., Zhang Y., Zheng M. (2023): A novel and controllable method for simultaneous preparation of human milk fat substitutes (OPL, OPO and LPL): two-step enzymatic ethanolysis-esterification strategy. Food Research International, 163: 112168. Go to original source... Go to PubMed...
    19. Martins A.B., da Silva A.M., Schein M.F., Garcia-Galan C., Ayub M.A.Z., Fernandez-Lafuente R., Rodrigues R.C. (2014): Comparison of the performance of commercial immobilized lipases in the synthesis of different flavor esters. Journal of Molecular Catalysis B: Enzymatic, 105: 18-25. Go to original source...
    20. National standard for food safety, Food nutrition fortifier, 1,3-dioleoyl-2-palmitate triglyceride (2015): GB30604-2015, National Health and Family Planning Commission of the People's Republic of China. Available at https://std.samr.gov.cn/ (accessed Oct 15, 2023).
    21. Miles E.A., Calder P.C. (2017): The influence of the position of palmitate in infant formula triacylglycerols on health outcomes. Nutrition Research, 44: 1-8. Go to original source... Go to PubMed...
    22. Peng L., Xu X., Mu H., Høy C.E., Adler-Nissen J. (2002): Production of structured phospholipids by lipase-catalyzed acidolysis: optimization using response surface methodology. Enzyme and Microbial Technology, 31: 523-532. Go to original source...
    23. Ramiro-Cortijo D., Singh P., Liu Y., Medina-Morales E., Yakah W., Freedman S.D., Martin C.R. (2020): Breast milk lipids and fatty acids in regulating neonatal intestinal development and protecting against intestinal injury. Nutrients, 12: 534. Go to original source... Go to PubMed...
    24. Wei W., Jin Q., Wang X. (2019): Human milk fat substitutes: Past achievements and current trends. Progress in Lipid Research, 74: 69-86. Go to original source... Go to PubMed...
    25. Wei W., Sun C., Wang X., Jin Q., Xu X., Akoh C.C., Wang X. (2020): Lipase-catalyzed synthesis of sn-2 palmitate: A review. Engineering, 6: 406-414. Go to original source...
    26. Zhu S.Y., Xu Y., Yu X.W. (2020): Improved Homologous Expression of the Acidic Lipase from Aspergillus niger. Journal of microbiology and biotechnology, 30: 196-205. Go to original source... Go to PubMed...

    This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY NC 4.0), which permits non-comercial use, distribution, and reproduction in any medium, provided the original publication is properly cited. No use, distribution or reproduction is permitted which does not comply with these terms.


    Return to the content