Skip to main content
Log in

Lysozyme-(-)-epigallocatechin gallate covalent conjugates: preparation, structure and functional properties

  • Original Paper
  • Published:
Journal of Food Measurement and Characterization Aims and scope Submit manuscript

Abstract

The development of multi-functional preservatives is a promising solution to food waste caused by microbial spoilage. Therefore, in the present study, lysozyme - (-)-epigallocatechin gallate (Ly-EGCG) covalent conjugates were prepared by a free radical grafting approach. The effects of EGCG concentration on the physicochemical, structural, antioxidant, and antibacterial properties of Ly-EGCG conjugates were investigated. The covalent coupling of Ly with EGCG was confirmed by the generation of new bands in sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) profiles, the decrease in fluorescence intensity (> 85%) shown by multispectral techniques, and the shift of the amide I band in the Fourier transform infrared (FTIR) spectra. Compared to Ly, after adding 0.7 mM EGCG, the thermal denaturation temperature of the Ly-EGCG conjugates was decreased to 68.84 °C, whereas the DPPH scavenging capacity (88.84 ± 0.42%) and total antioxidant capacity (0.94 ± 0.06 U/mL) were remarkably enhanced. The inhibitory effect of Ly-EGCG conjugates on E. coli and S. aureus could be effectively regulated by modifying the EGCG concentration. Furthermore, Pearson correlation analysis revealed a correlation between the structural and functional properties of Ly-EGCG conjugates. These results provide potential strategies for the development of food-grade, multi-functional preservatives.

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.

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

Similar content being viewed by others

References

  1. J.J. Silva, M.R. de Miranda, P.F. Souza, Curr. Opin. Food Sci. 54, 101089 (2023)

    Article  CAS  Google Scholar 

  2. L. Zhang, X. Gao, Y. Feng, Y. Yan, H. Zhu, S. Liu, Y. Yu, B. Yu, ACS Appl. Mater. Interfaces. 15(37), 44097–44108 (2023)

    Article  CAS  PubMed  Google Scholar 

  3. M.A. Shabkhiz, M. Khalil Pirouzifard, S. Pirsa, G.R. Mahdavinia, J. Mol. Liq. 344, 117738 (2021)

    Article  CAS  Google Scholar 

  4. M. Yan, S. Dong, X. Shen, C. Lu, H. Ye, T. Zhang, Food Funct. 12(22), 11165–11173 (2021)

    Article  CAS  PubMed  Google Scholar 

  5. Y. Yu, Y. Shi, J. Food Meas. Charact. 17(6), 5594–5605 (2023)

    Article  Google Scholar 

  6. B. Ben Akacha, M. Michalak, B. Najar, F. Venturi, I. Taglieri, M. Kačániová, R. Ben Saad, W. Mnif, S. Garzoli, Ben Hsouna Foods. 12(8), 1647 (2023)

    Article  CAS  PubMed  Google Scholar 

  7. N. Nawaz, S. Wen, F. Wang, S. Nawaz, J. Raza, M. Iftikhar, M. Usman, Molecules. 27(19), 6305 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Z. Wei, S. Wu, J. Xia, P. Shao, P. Sun, N. Xiang, Biomacromolecules. 22(2), 890–897 (2021)

    Article  CAS  PubMed  Google Scholar 

  9. Q. Zhang, Y. Zhao, Y. Yao, N. Wu, S. Chen, L. Xu, Y. Tu, Food Res. Int. 181, 114114 (2024)

    Article  CAS  PubMed  Google Scholar 

  10. B. Masoumi, M. Tabibiazar, Z. Golchinfar, M. Mohammadifar, H. Hamishehkar, Crit. Rev. Food Sci. Nutr. 1–17 (2022)

  11. Y. Meng, C. Li, Food Chem. 364, 129622 (2021)

    Article  CAS  PubMed  Google Scholar 

  12. S. Yan, Q. Wang, J. Yu, Y. Li, B. Qi, Ultrason. Sonochem. 100, 106645 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. J. Zheng, N. Xiao, Y. Li, X. Xie, L. Li, LWT. 153, 112438 (2022)

    Article  CAS  Google Scholar 

  14. S. Dai, P. Liao, Y. Wang, T. Tian, X. Tong, B. Lyu, L. Cheng, L. Miao, W. Qi, L. Jiang, H. Wang, Food Hydrocoll. 135, 108108 (2023)

    Article  CAS  Google Scholar 

  15. H. Li, Y. Pan, C. Li, Z. Yang, J. Rao, B. Chen, Food Chem. 370, 131032 (2022)

    Article  CAS  PubMed  Google Scholar 

  16. H. Li, Y. Pan, C. Li, Z. Yang, J. Rao, B. Chen, Food Chem. 406, 135070 (2023)

    Article  CAS  PubMed  Google Scholar 

  17. Y. Li, X. Liu, F. Yin, D. Li, P. Jiang, L. Song, Y. Nakamura, D. Zhou, Food Biosci. 51, 102215 (2023)

    Article  CAS  Google Scholar 

  18. Z. Han, Z. Chen, X. Xu, S. Lin, Y. Wang, L. Wang, D. Niu, X. Zeng, M. Woo, R. Wang, Food Hydrocoll. 151, 109826 (2024)

    Article  CAS  Google Scholar 

  19. Z. He, H. Luo, Z. Wang, D. Chen, Q. Feng, X. Cao, Carbohydr. Polym. 299, 120180 (2023)

    Article  CAS  PubMed  Google Scholar 

  20. X. Han, Z. Liang, S. Tian, L. Liu, S. Wang, Food Res. Int. 158, 111534 (2022)

    Article  CAS  PubMed  Google Scholar 

  21. X. Li, M. Li, T. Zhang, D.J. McClements, X. Liu, X. Wu, F. Liu, J. Agric. Food Chem. 69, 6291 (2021)

    Article  CAS  PubMed  Google Scholar 

  22. J. Han, Y. Du, W. Shang, J. Yan, H. Wu, B. Zhu, H. Xiao, Food Funct. 10, 6752 (2019)

    Article  CAS  PubMed  Google Scholar 

  23. Y. Zheng, B. Chen, X. Huang, H. Teng, C. Ai, L. Chen, Ultrason. Sonochem. 95, 106396 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. S. Daei, F. Mohtarami, S. Pirsa, Polym. Bull. 79(12), 11317–11338 (2022)

    Article  CAS  Google Scholar 

  25. S. Pirsa, Int. J. Biol. Macromol. 193, 300–310 (2021)

    Article  CAS  PubMed  Google Scholar 

  26. W. Xu, W. Jin, Y. Wang, J. Li, K. Huang, B.R. Shah, B. Li, J. Food Sci. Technol. 55(8), 3056–3064 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. S. Pirsa, M. Mahmudi, A. Ehsani, Int. J. Biol. Macromol. 224, 1588–1599 (2023)

    Article  CAS  PubMed  Google Scholar 

  28. R.A. Yorghanlu, H. Hemmati, S. Pirsa, A. makhani, Polym. Bull. 79(10), 8217–8240 (2022)

    Article  CAS  Google Scholar 

  29. S. Pirsa, B. Mohammadi, Main Group. Chem. 20(2), 133–147 (2021)

    Article  CAS  Google Scholar 

  30. L. Sheng, P. Su, K. Han, J. Chen, A. Cao, Z. Zhang, Y. Jin, M. Ma, Food Hydrocoll. 71, 1 (2017)

    Article  CAS  Google Scholar 

  31. Y. Wang, Y. Chen, J. Lv, C. Li, F. Wang, J. Food Sci. Technol. 60, 2454–2467 (2023)

    Article  CAS  PubMed  Google Scholar 

  32. J. Feng, H. Cai, H. Wang, C. Li, S. Liu, Food Chem. 241, 60–69 (2018)

    Article  CAS  PubMed  Google Scholar 

  33. Y. Jia, X. Yan, X. Li, S. Zhang, Y. Huang, D. Zhang, Y. Li, B. Qi, Food Chem. 404, 134610 (2023)

    Article  CAS  PubMed  Google Scholar 

  34. Y. Ma, S. Zhang, Y. Feng, H. Wang, Y. Liu, C. Wang, Foods 12(11), 2091 (2023)

  35. W. Gong, H. Huang, X. Wang, W. He, Y. Hou, J. Hu, Biomater. Sci. 10(23), 6836–6849 (2022)

    Article  CAS  PubMed  Google Scholar 

  36. X. Pi, Y. Sun, J. Liu, X. Wang, W. Hong, J. Cheng, M. Guo, Food Hydrocoll. 134, 108107 (2023)

    Article  CAS  Google Scholar 

  37. B. Zhang, H. Tao, X. Niu, S. Li, H. Chen, Food Chem. 227, 137–141 (2017)

    Article  CAS  PubMed  Google Scholar 

  38. L. Pan, J. Chen, H. Fu, N. Wang, J. Zhou, S. Zhang, S. Lu, J. Dong, Q. Wang, H. Yan, Food Biosci. 52, 102375 (2023)

    Article  CAS  Google Scholar 

  39. S. Yan, F. Xie, S. Zhang, L. Jiang, B. Qi, Y. Li, Colloids Surf. A 609, 125641 (2021)

    Article  CAS  Google Scholar 

  40. Y. Lu, S. Li, H. Xu, T. Zhang, X. Lin, X. Wu, J. Agric. Food Chem. 66, 9794–9800 (2018)

    Article  CAS  PubMed  Google Scholar 

  41. W. He, T. Zhang, T.C. Velickovic, S. Li, Y. Lyu, L. Wang, J. Yi, Z. Liu, Z. He, X. Wu, Food Chem. 331, 127355 (2020)

    Article  CAS  PubMed  Google Scholar 

  42. Y. Wang, J. Zhou, X. Tian, L. Bai, C. Ma, Y. Chen, Y. Li, W. Wang, J. Agric. Food Chem. 71(48), 19020 (2023)

    Article  CAS  PubMed  Google Scholar 

  43. S. Yu, P. Yao, M. Jiang, G. Zhang, Biopolymers. 83(2), 148–158 (2006)

    Article  CAS  PubMed  Google Scholar 

  44. C. Ren, W. Xiong, B. Li, Food Biophys. 18(3), 402–410 (2023)

    Article  Google Scholar 

  45. J. Yang, Y. Zhao, B. Shan, Y. Duan, J. Zhou, M. Cai, H. Zhang, Int. J. Biol. Macromol. 250, 126006 (2023)

    Article  CAS  PubMed  Google Scholar 

  46. W. Xu, Y. Jia, J. Wei, Y. Ning, H. Sun, L. Jiang, L. Chai, D. Luo, S. Cao, B.R. Shah, RSC Adv. 12(49), 32061–32069 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. J. Liu, Y. Wang, J. Lv, Y. Wu, Y. Guo, C. Sun, X. Li, Food Packag Shelf Life. 38, 101098 (2023)

    Article  CAS  Google Scholar 

  48. R. Cegielska-Radziejewska, G. Lesnierowski, T. Szablewski, J. Kijowski, Eur. Food Res. Technol. 231(6), 959–964 (2010)

    Article  CAS  Google Scholar 

  49. L. Wang, L. Li, N. Xu, W. Sun, B. Ding, W. Xu, Z. Li, Food Hydrocoll. 98, 105263 (2020)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the Hubei Key Laboratory for processing and Transformation of Agricultural Products (Grant No. 2018HBSQGDKFB03), Natural Science Foundation of Henan province (Grant No. 162300410229), Natural Science Foundation of Henan (Grant No. 222103810071), National Natural Science Foundation of China (Grant No. U2004160), and Nanhu Scholars Program for Young Scholars of XYNU.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Denglin Luo, Weiping Jin or Wei Xu.

Ethics declarations

Conflict of interest

No conflict of interest is reported.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yin, Y., Luo, D., Jin, W. et al. Lysozyme-(-)-epigallocatechin gallate covalent conjugates: preparation, structure and functional properties. Food Measure (2024). https://doi.org/10.1007/s11694-024-02530-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s11694-024-02530-w

Keywords

Navigation