Skip to main content
SpringerLink
Log in

Improving interface-related functions and antioxidant activities of soy protein isolate by covalent conjugation with chlorogenic acid

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

Abstract

The conjugation of protein and chlorogenic acid was expected to change protein structure and improve protein functional properties. The study investigated the effect of covalent interactions of soy protein isolate (SPI) and chlorogenic acid (CA) at different concentrations (20, 40, 60, 80, 100 μmol/g protein) on the interface-related functions and antioxidant activities. The results showed that the conjugation rate was directly proportional to the CA concentration. The results of SDS-PAGE analysis revealed that covalent complexes were formed. The intrinsic fluorescence spectroscopy and ultraviolet spectroscopy indicated that CA tended to unfold the structure of SPI. Correspondingly, the flexibility was greatly enhanced by 183.06%, and a significant decrease (26.06%) in the surface hydrophobicity was caused. In addition, the DPPH and ABTS radical scavenging activities constantly increased by 10.87% and 33.08 μmol Trolox Equivalent (TE)/g protein with CA of 100 μmol/g protein. However, the solubility, emulsifying stability and foaming properties increased first and then decreased with the increase of CA concentration. They all reached the maximum when CA was 80 μmol/g protein, respectively, 47.77 ± 0.15%, 39.55 ± 1.27 min, and 3155.76 ± 52.02%. And the particle size was the smallest at this time, particles smaller than 10 nm had the largest volume fraction. In summary, SPI had the greatest improvement in the interface-related functional properties and excellent antioxidant activities with CA of 80 μmol/g protein. This work elucidates that SPI-CA covalent conjugates can be used as a new food ingredient in emulsion food systems to improve food quality.

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

Access this article

Log in via an institution

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

Similar content being viewed by others

References

  1. C.H. Tang, X.Y. Wang, X.Q. Yang, L. Lin, Formation of soluble aggregates from insoluble commercial soy protein isolate by means of ultrasonic treatment and their gelling properties. J Food Eng. 92(4), 432–437 (2009)

    Article  CAS  Google Scholar 

  2. B. Grazyna, P. Bartłomiej, R.R. Danuta, O. Joanna, Z. Donata, B. Sylwia, N. Inmaculada, M.V.M. Josefina, P. Horacio, Effect of inclusion of hydroxycinnamic and chlorogenic acids from green coffee bean in b-cyclodextrin on their interactions with whey, egg white and soy protein isolates. Food Chem. 168, 276–287 (2015)

    Article  Google Scholar 

  3. D. Li, Y. Zhao, X. Wang, H. Tang, N. Wu, F. Wu, D.Y. Yu, W. Elfalleh, Effects of (+)-catechin on a rice bran protein oil-in-water emulsion: droplet size, zeta-potential, emulsifying properties, and rheological behavior. Food Hydrocoll. 98, 105306 (2019)

    Article  Google Scholar 

  4. J. Jiang, Z.P. Zhang, J. Zhao, Y.F. Liu, The effect of non-covalent interaction of chlorogenic acid with whey protein and casein on physicochemical and radical-scavenging activity of in vitro protein digests. Food Chem. 268, 334–341 (2018)

    Article  CAS  PubMed  Google Scholar 

  5. M.N. Ju, G. Zhu, G. Huang, X.C. Shen, Y. Zhang, L.Z. Jiang, X.N. Sui, A novel pickering emulsion produced using soy protein-anthocyanin complex nanoparticles. Food Hydrocoll. 99, 105329 (2020)

    Article  CAS  Google Scholar 

  6. R. Yang, J. Tian, Y. Liu, L. Zhu, J. Sun, D. Meng, Z. Wang, C. Wang, Z. Zhou, L. Chen, Interaction mechanism of ferritin protein with chlorogenic acid and iron ion: the structure, iron redox, and polymerization evaluation. Food Chem. 349(11), 129144 (2021)

    Article  CAS  PubMed  Google Scholar 

  7. L. Sęczyk, M. Świeca, I. Kapusta, U. Gawlik-Dziki, Protein-phenolic interactions as a factor affecting the physicochemical properties of white bean proteins. Molecules 24(3), 408 (2019)

    Article  PubMed Central  Google Scholar 

  8. T.H. Quan, S. Benjakul, T. Sae-Leaw, A.K. Balange, S. Maqsood, Protein-polyphenol conjugates: antioxidant property, functionalities and their applications. Trends Food Sci. Technol. 91, 507–517 (2019)

    Article  CAS  Google Scholar 

  9. T. Narges, T. Mahboubeh, M. Isabelle, E. Paul, The potential effects of chlorogenic acid, the main phenolic components in coffee, on health: a comprehensive review of the literature. Eur J. Nutr. 56, 2215–2244 (2017)

    Article  Google Scholar 

  10. M.T. Huang, R.C. Smart, C.Q. Wong, A.H. Conney, Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res. 48(21), 5941–5946 (1988)

    CAS  PubMed  Google Scholar 

  11. H.X. Xu, T.T. Zhang, Y.Q. Lu, X. Lin, X.P. Hu, L.Z. Liu, Z.D. He, X.L. Wu, Effect of chlorogenic acid covalent conjugation on the allergenicity, digestibility and functional properties of whey protein. Food Chem. 298, 125024 (2019)

    Article  CAS  PubMed  Google Scholar 

  12. J. Sun, H. Jing, Y.Y. Mu, D.J. McClements, S.J. Dong, B. Xu, Fabrication of antioxidant emulsifiers from natural ingredients: conjugation of egg white proteins with catechin and chlorogenic acid. Food Hydrocoll. 108, 106019 (2020)

    Article  CAS  Google Scholar 

  13. W. Herchi, I. Bouali, S. Bahashwan, S. Rochut, S. Boukhchina, H. Kallel, C. Pepe, Changes in phospholipid composition, protein content and chemical properties of flaxseed oil during development. Plant Physiol. Biochem. 54, 1–5 (2012)

    Article  CAS  PubMed  Google Scholar 

  14. X.L. Wu, Y.Q. Lu, H.X. Xu, D.X. Lin, Z.D. He, H.Q. Wu, L.Z. Liu, Z.M. Wang, Reducing the allergenic capacity of beta-lactoglobulin by covalent conjugation with dietary polyphenols. Food Chem. 256, 427–434 (2018)

    Article  CAS  PubMed  Google Scholar 

  15. S. Hayakawa, S. Nakai, Relationships of hydrophobicity and net charge to the solubility of milk and soy proteins. J. Food Sci. 50(2), 486–491 (1985)

    Article  CAS  Google Scholar 

  16. M. Jouki, N. Khazaei, S. Rashidi-Alavijeh, S. Ahmadi, Encapsulation of lactobacillus casei in quince seed gum-alginate beads to produce a functional synbiotic drink powder by agro-industrial by-products and freeze-drying. Food Hydrocoll. 120, 106895 (2021)

    Article  CAS  Google Scholar 

  17. A. Kato, H.R. Ibrahim, H. Watanabe, K. Honma, K. Kobayashi, Structure and gelling properties of dry-heating egg white proteins. J. Agric. Food Chem. 38(1), 32–37 (1990)

    Article  CAS  Google Scholar 

  18. U.K. Laemmli, Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227(5259), 680–685 (1970)

    Article  CAS  PubMed  Google Scholar 

  19. F.G. Liu, C.C. Ma, D.J. Mcclements, Y.X. Gao, A comparative study of covalent and non-covalent interactions between zein and polyphenols in ethanol-water solution. Food Hydrocoll. 63, 625–634 (2017)

    Article  CAS  Google Scholar 

  20. M. Jouki, S.A. Mortazavi, F.T. Yazdi, A. Koocheki, Optimization of extraction, antioxidant activity and functional properties of quince seed mucilage by rsm. Int. J. Biol. Macromol. 66(5), 113–124 (2014)

    Article  CAS  PubMed  Google Scholar 

  21. M.B. Bera, R.K. Mukherjee, Solubility, emulsifying, and foaming properties of rice bran protein concentrates. J. Food Sci. 54(1), 142–145 (1989)

    Article  CAS  Google Scholar 

  22. X.Q. Huang, Z.C. Tu, H. Wang, Q.T. Zhang, Y. Shi, H. Xiao, Increase of ovalbumin glycation by the maillard reaction after disruption of the disulfide bridge evaluated by liquid chromatography and high resolution mass spectrometry. J. Agric. Food Chem. 61(9), 2253–2262 (2013)

    Article  CAS  PubMed  Google Scholar 

  23. F. Alipoorfard, M. Jouki, H. Tavakolipour, Application of sodium chloride and quince seed gum pretreatments to prevent enzymatic browning, loss of texture and antioxidant activity of freeze dried pear slices. J. Food Sci. Technol. 57, 3165 (2020)

    Article  PubMed  PubMed Central  Google Scholar 

  24. M.S. Coelho, S.D.A. Aquino, J.M. Latorres, M.D.L.M. Salas-Mellado, In vitro and in vivo antioxidant capacity of chia protein hydrolysates and peptides. Food Hydrocoll. 91, 19–25 (2019)

    Article  Google Scholar 

  25. S.D. Rodriguez, M. Von Staszewski, A.M.R. Pilosof, Green tea polyphenols-whey proteins nanoparticles: bulk, interfacial and foaming behavior. Food Hydrocoll. 50, 108–115 (2015)

    Article  CAS  Google Scholar 

  26. T. Aewsiri, S. Benjakul, W. Visessanguan, P.A. Wierenga, H. Gruppen, Emulsifying property and antioxidative activity of cuttle fish skin gelatin modified with oxidized linoleic acid and oxidized tannic acid. Food Bioprocess Technol. 6, 870–881 (2013)

    Article  CAS  Google Scholar 

  27. Y.C. Chen, C. Wang, H.T. Liu, Q. Liu, B.H. Kong, Enhanced physical and oxidative stability of porcine plasma protein hydrolysates based oil-in-water emulsions by adding oxidized chlorogenic acid. Colloids Surf. A 558, 330–337 (2018)

    Article  CAS  Google Scholar 

  28. L. Razumovsky, S. Damodaran, Surface activity compressibility relationship of proteins at the airwater interface. Langmuir 15(4), 1392–1399 (1999)

    Article  CAS  Google Scholar 

  29. S. Gorinstein, M. Zemser, O. Paredes-López, Structural stability of globulins. J. Agric. Food Chem. 44(1), 100–105 (1996)

    Article  CAS  Google Scholar 

  30. A. Mostafa, H. Thomas, K. Mahmoud, K. Hans-Peter, R. Harshadrai, Milk whey protein modification by coffee-specific phenolics: effect on structural and functional properties. J. Agric. Food Chem. 61(28), 6911–6920 (2013)

    Article  Google Scholar 

  31. H.M. Rawel, D. Czajka, S. Rohn, J. Kroll, Interactions of different phenolic acids and flavonoids with soy proteins. Int. J. Biol. Macromol. 30(3–4), 137–150 (2002)

    Article  CAS  PubMed  Google Scholar 

  32. Y. Cao, Y.L. Xiong, Chlorogenic acid-mediated gel formation of oxidatively stressed myofibrillar protein. Food Chem. 180, 235–243 (2015)

    Article  CAS  PubMed  Google Scholar 

  33. Y.M. Zhang, L. Chen, Y.Q. Lv, S.X. Wang, Z.Y. Suo, X.G. Cheng, X.L. Xu, G.H. Zhou, Z.X. Li, X.C. Feng, Inhibition of interaction between epigallocatechin-3-gallate and myofibrillar protein by cyclodextrin derivatives improves gel quality under oxidative stress. Food Res. Int. 108, 8–17 (2018)

    Article  CAS  PubMed  Google Scholar 

  34. M.X. Xie, M. Long, Y. Liu, C. Qin, Y.D. Wang, Characterization of the interaction between human serum albumin and morin. Biochim. Biophys. Acta 1760(8), 1184–1191 (2006)

    Article  CAS  PubMed  Google Scholar 

  35. W.Y. He, H.X. Xu, Y.Q. Lu, T.T. Zhang, S.M. Li, X. Lin, B.Q. Xu, X.L. Wu, Function, digestibility and allergenicity assessment of ovalbumin-EGCG conjugates. J. Funct. Foods. 61, 103490 (2019)

    Article  CAS  Google Scholar 

  36. F. Liu, C. Sun, W. Yang, F. Yuan, Y. Gao, Structural characterization and functional evaluation of lactoferrin-polyphenol conjugates formed by free-radical graft copolymerization. RSC Adv. 5(20), 15641–15651 (2015)

    Article  CAS  Google Scholar 

  37. T. Ozdal, E. Capanoglu, F. Altay, A review on protein-phenolic interactions and associated changes. Food Res. Int. 51(2), 954–970 (2013)

    Article  CAS  Google Scholar 

  38. N. Maruyama, M.R.M. Salleh, K. Takahashi, K. Yagasaki, H. Goto, N. Hontani, S. Nakagawa, S. Utsumi, Structure-physicochemical function relationships of soybean beta-conglycinin heterotrimers. J. Agric. Food Chem. 50(15), 4323–4326 (2002)

    Article  CAS  PubMed  Google Scholar 

  39. M.A. Bos, T.V. Vliet, Interfacial rheological properties of adsorbed protein layers and surfactants: a review. Adv. Colloid Interface Sci. 91(3), 437–471 (2001)

    Article  CAS  PubMed  Google Scholar 

  40. X. Wang, J. Zhang, F. Lei, C. Liang, F. Yuan, Y. Gao, Covalent complexation and functional evaluation of (-)-epigallocatechin gallate and α-lactalbumin. Food Chem. 150, 341–347 (2014)

    Article  CAS  PubMed  Google Scholar 

  41. A. Townsend, S. Nakai, Relationships between hydrophobicity and foaming characteristics of food proteins. J. Food Sci. 48(2), 588–594 (1983)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The project was funded by Heilongjiang Province Engineering Science and Technology Major Special Project (2019ZX08B01) and National Soybean Industrial Technology System of China (CARS-04-PS28).

Author information

Authors and Affiliations

  1. College of Food Science, Northeast Agricultural University, Harbin, 150030, Heilongjiang, China

    Kaiyan Guo, Guowei Zhou, Uh Song Lok, Xibo Wang & Lianzhou Jiang

Authors
  1. Kaiyan Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Guowei Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Uh Song Lok
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xibo Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lianzhou Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xibo Wang.

Ethics declarations

Conflict of interest

No conflicts of interest are declared in regards to the publication of this work for any of the authors.

Additional information

Publisher's Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Guo, K., Zhou, G., Lok, U.S. et al. Improving interface-related functions and antioxidant activities of soy protein isolate by covalent conjugation with chlorogenic acid. Food Measure 16, 202–213 (2022). https://doi.org/10.1007/s11694-021-01148-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11694-021-01148-6

Keywords

Search

Navigation