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An Effective Strategy for the Production of Lauric Acid–Enriched Monoacylglycerol via Enzymatic Glycerolysis from Black Soldier Fly (Hermetia illucens) Larvae (BSFL) Oil

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Abstract

Here, we developed an efficient strategy for the production of lauric acid–enriched monoacylglycerol (MAG) via enzymatic glycerolysis using black soldier fly (Hermetia illucens) larvae (BSFL) oil. The effects of the substrate molar ratio, reaction temperature, type of immobilized lipase, and organic solvent on the MAG content and conversion degree of BSFL oil were optimized. The maximum substrate conversion rate (97.88%) and MAG content (70.84%) were obtained in a tert-butanol system at 50 °C with a glycerol/BSFL oil molar ratio of 4:1 by using immobilized MAS1 lipase as a catalyst. The MAG content in the purified product reached 97.7%, with lauric acid accounting for 50.2%. Improved oxidation stability was observed after glycerolysis. Overall, this study provides a new strategy for the preparation of lauric acid–enriched MAG from BSFL oil.

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References

  1. Hobuss, C. B., da Silva, F. A., dos Santos, M. A. Z., de Pereira, C. M. P., Schulz, G. A. S., & Bianchini, D. (2020). Synthesis and characterization of monoacylglycerols through glycerolysis of ethyl esters derived from linseed oil by green processes. Rsc Advances, 10(4), 2327–2336.

    Article  CAS  Google Scholar 

  2. Monteiro, J. B., Nascimento, M. G., & Ninow, J. L. (2003). Lipase-catalyzed synthesis of monoacylglycerol in a homogeneous system. Biotechnology Letters, 25(8), 641–644.

    Article  CAS  Google Scholar 

  3. Ham, Y., & Kim, T. J. (2016). Inhibitory activity of monoacylglycerols on biofilm formation in Aeromonas hydrophila, Streptococcus mutans, Xanthomonas oryzae, and Yersinia enterocolitica. Springerplus, 5(1), 1526.

    Article  Google Scholar 

  4. Schlievert, P. M., Kilgore, S. H., Seo, K. S., & Leung, D. Y. M. (2019). Glycerol monolaurate contributes to the anti-microbial and anti-inflammatory activity of human milk. Scientific Reports, 9, 9.

    Article  Google Scholar 

  5. Guebara, S. A. B., Ract, J. N. R., & Vitolo, M. (2018). Conversion of caprylic acid into mono-, di- and triglycerides using immobilized lipase. Arabian Journal for Science and Engineering, 43(7), 3631–3637.

    Article  CAS  Google Scholar 

  6. Zha, B., Chen, Z., Wang, L., Wang, R., Chen, Z., & Zheng, L. (2014). Production of glycerol monolaurate-enriched monoacylglycerols by lipase-catalyzed glycerolysis from coconut oil. European Journal of Lipid Science and Technology, 116(3), 328–335.

    Article  CAS  Google Scholar 

  7. Sun, S. D., & Hu, B. X. (2017). A novel method for the synthesis of glyceryl monocaffeate by the enzymatic transesterification and kinetic analysis. Food Chemistry, 214, 192–198.

    Article  CAS  Google Scholar 

  8. Eyres, L., Eyres, M. F., Chisholm, A., & Brown, R. C. (2016). Coconut oil consumption and cardiovascular risk factors in humans. Nutrition Reviews, 74(4), 267–280.

    Article  Google Scholar 

  9. Cammack, J. A., & Tomberlin, J. K. (2017). The impact of diet protein and carbohydrate on select life-history traits of the black soldier fly Hermetia illucens (L.) (Diptera: Stratiomyidae). Insects, 8(2), 56.

    Article  Google Scholar 

  10. Ishak, S., & Kamari, A. (2019). Biodiesel from black soldier fly larvae grown on restaurant kitchen waste. Environmental Chemistry Letters, 17(2), 1143–1150.

    Article  CAS  Google Scholar 

  11. Beskin, K. V., Holcomb, C. D., Cammack, J. A., Crippen, T. L., Knap, A. H., Sweet, S. T., & Tomberlin, J. K. (2018). Larval digestion of different manure types by the black soldier fly (Diptera: Stratiomyidae) impacts associated volatile emissions. Waste Management, 74, 213–220.

    Article  CAS  Google Scholar 

  12. Ewald, N., Vidakovic, A., Langeland, M., Kiessling, A., Sampels, S., & Lalander, C. (2020). Fatty acid composition of black soldier fly larvae (Hermetia illucens) - Possibilities and limitations for modification through diet. Waste Management, 102, 40–47.

    Article  CAS  Google Scholar 

  13. Barragan-Fonseca, K. B., Dicke, M., & van Loon, J. J. A. (2017). Nutritional value of the black soldier fly (Hermetia illucens L.) and its suitability as animal feed - A review. J Insects Food Feed, 3(2), 105–120.

    Article  Google Scholar 

  14. Wang, X., Li, D., Qu, M., Durrani, R., Yang, B., & Wang, Y. (2017). Immobilized MAS1 lipase showed high esterification activity in the production of triacylglycerols with n-3 polyunsaturated fatty acids. Food Chemistry, 216, 260–267.

    Article  CAS  Google Scholar 

  15. Basso, A., Froment, L., Hesseler, M., & Serban, S. (2013). New highly robust divinyle benzene/acrylate polymer for immobilization of lipase CALB. European Journal of Lipid Science and Technology, 115(4), 468–472.

    Article  CAS  Google Scholar 

  16. Li, D., Qin, X., Wang, J., Yang, B., Wang, W., Huang, W., & Wang, Y. (2015). Hydrolysis of soybean oil to produce diacylglycerol by a lipase from Rhizopus oryzae. Journal of Molecular Catalysis B: Enzymatic, 115, 43–50.

    Article  CAS  Google Scholar 

  17. Qin, X., Lan, D., Zhong, J., Liu, L., Wang, Y., & Yang, B. (2014). Fatty acid specificity of T1 lipase and its potential in acylglycerol synthesis. Journal of the Science of Food and Agriculture, 94(8), 1614–1621.

    Article  CAS  Google Scholar 

  18. Cai, C. S., Gao, Y. Q., Liu, Y., Zhong, N. J., & Liu, N. (2016). Immobilization of Candida antarctica lipase B onto SBA-15 and their application in glycerolysis for diacylglycerols synthesis. Food chemistry, 212, 205–212.

    Article  CAS  Google Scholar 

  19. Palacios, D., Ortega, N., Rubio-Rodriguez, N., & Busto, M. D. (2019). Lipase-catalyzed glycerolysis of anchovy oil in a solvent-free system: Simultaneous optimization of monoacylglycerol synthesis and end-product oxidative stability. Food Chemistry, 271, 372–379.

    Article  CAS  Google Scholar 

  20. Duan, Z., Du, W., & Liu, D. H. (2010). The pronounced effect of water activity on the positional selectivity of Novozym 435 during 1,3-diolein synthesis by esterification. Catalysis Communications, 11(5), 356–358.

    Article  CAS  Google Scholar 

  21. Du, W., Wang, L., & Liu, D. (2007). Improved methanol tolerance during Novozym 435-mediated methanolysis of SODD for biodiesel production. Green Chemistry, 9(2), 173–176.

    Article  CAS  Google Scholar 

  22. Jeong, G. T., & Park, D. H. (2008). Lipase-catalyzed transesterification of rapeseed oil for biodiesel production with tert-butanol. Applied Biochemistry and Biotechnology, 148(1-3), 131–139.

    Article  CAS  Google Scholar 

  23. Zeng, F. K., Yang, B., Wang, Y. H., Wang, W. F., Ning, Z. X., & Li, L. (2010). Enzymatic production of monoacylglycerols with camellia oil by the glycerolysis reaction. Journal of the American Oil Chemists Society, 87(5), 531–537.

    Article  CAS  Google Scholar 

  24. Damstrup, M. L., Jensen, T., Sparsø, F. V., Kiil, S. Z., Jensen, A. D., & Xu, X. (2005). Solvent optimization for efficient enzymatic monoacylglycerol production based on a glycerolysis reaction. Journal of the American Oil Chemists Society, 82(8), 559–564.

    Article  CAS  Google Scholar 

  25. Kaewthong, W., & H-Kittikun, A. (2004). Glycerolysis of palm olein by immobilized lipase PS in organic solvents. Enzyme and Microbial Technology, 35(2-3), 218–222.

    Article  CAS  Google Scholar 

  26. Krüger, R. L., Valério, A., Balen, M., Ninow, J. L., Oliveira, N., de Oliveira, D., & Corazza, L. M. (2010). Improvement of mono and diacylglycerol production via enzymatic glycerolysis in tert-butanol system. European Journal of Lipid Science and Technology, 112(8), 921–927.

    Article  Google Scholar 

  27. Galúcio, C. S., Souza, R. A., Stahl, M. A., Sbaite, P., Benites, C. I., & Maciel, M. R. W. (2011). Physicochemical characterization of monoacylglycerols from sunflower oil. Procedia Food Science, 1, 1459–1464.

    Article  Google Scholar 

  28. Nitbani, F. O., Tjitda, P. J. P., Nurohmah, B. A., & Wogo, H. E. (2020). Preparation of fatty acid and monoglyceride from vegetable oil. Journal of Oleo Science, 69(4), 277–295.

    Article  CAS  Google Scholar 

  29. Gold, M., Tomberlin, J. K., Diener, S., Zurbrugg, C., & Mathys, A. (2018). Decomposition of biowaste macronutrients, microbes, and chemicals in black soldier fly larval treatment: A review. Waste Management, 82, 302–318.

    Article  CAS  Google Scholar 

  30. Surendra, K. C., Olivier, R., Tomberlin, J. K., Jha, R., & Khanal, S. K. (2016). Bioconversion of organic wastes into biodiesel and animal feed via insect farming. Renewable Energy, 98, 197–202.

    Article  CAS  Google Scholar 

  31. Nakatsugawa, K., Ohashi, K., & Shimada, A. (2001). Comparison of oxidative stability of diacylglycerol and triacylglycerol. Journal of the Japanese Society for Food Science and Technology, 48(6), 429–436.

    Article  CAS  Google Scholar 

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Funding

This work was financially supported by the China Agriculture Research System (CARS-18-ZJ0503), the Science and Technology Planning Project of Guangdong Province (2019A050503002), the National Science Fund for Distinguished Young Scholars of China (31725022), the Key Program of National Natural Science Foundation of China (31930084), and the National Key R&D Program of China (2019YFD1002405).

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Authors and Affiliations

  1. School of Food Science and Engineering, South China University of Technology, Guangzhou, 510640, China

    Wanli Xu, Long Xu, Xuan Liu, Shi He, Yingrui Ji & Fanghua Wang

  2. Sericultural and Agri-food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, 510610, China

    Weifei Wang

Authors
  1. Wanli Xu
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  2. Long Xu
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  3. Xuan Liu
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  4. Shi He
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  5. Yingrui Ji
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  6. Weifei Wang
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  7. Fanghua Wang
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Contributions

Conceptualization: Wanli Xu; Material preparation: Wanli Xu; Data collection and analysis: Wanli Xu; Writing—original draft preparation: Wanli Xu; Writing—review and editing: Long Xu and Xuan Liu; Formal analysis and investigation: Shi He and Yingrui Ji; Funding acquisition: Weifei Wang and Fanghua Wang; Resources: Weifei Wang

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Correspondence to Weifei Wang or Fanghua Wang.

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Xu, W., Xu, L., Liu, X. et al. An Effective Strategy for the Production of Lauric Acid–Enriched Monoacylglycerol via Enzymatic Glycerolysis from Black Soldier Fly (Hermetia illucens) Larvae (BSFL) Oil. Appl Biochem Biotechnol 193, 2781–2792 (2021). https://doi.org/10.1007/s12010-021-03565-1

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