Abstract
In order to explore the structures and combination mechanism of wheat gluten peptides-calcium chelate (WOP-Ca) in depth, WOP-Ca were prepared by chelating wheat gluten peptides (WOP) with calcium. The yield of WOP-Ca was determined to be 51.2 ± 2.12 %, and it exhibited a calcium-chelating rate of 58.96 ± 1.38 %. The structural differences between WOP-Ca and WOP were characterized using various analytical techniques, and the results revealed that WOP-Ca and WOP differed in their microstructure, characteristic group absorption peaks, changes in electron cloud distribution, and thermal stability. WOP-Ca demonstrated remarkable stability and resistance to changes in pH, temperature, and in vitro digestion with gastric protease. After undergoing various treatments, the molecular weight distribution in each interval changed very little. Identification of the peptides in WOP-Ca was achieved by utilizing a mass spectrometer, and a total of 39 peptides were identified in WOP-Ca. Among these, 14 peptides with Score ≥ 30 and Coverage ≥ 20 showed bioavailability percentages exceeding 30 %, with half surpassing 50 %. The binding mode between the 14 peptides and Ca2+ was determined to be α linkage. The Ca–O bond lengths ranged from 2.40 to 3.20 Å, indicating the formation of structurally stable complexes. The carboxyl oxygen atoms played a crucial role in binding with Ca2+, with bond lengths ranging from 2.41 to 2.49 Å and 2.43 to 2.46 Å, respectively. The finding suggested that WOP-Ca prepared by chelation may be used as a calcium supplement that could serve as food additives, dietary nutrients, and pharmaceutical agents.
Funding source: Ningxia Natural Science Foundation Project
Award Identifier / Grant number: 2021BEG02027
Funding source: Technology Beijing Leading Talent Project
Award Identifier / Grant number: Z191100002819001
Acknowledgments
This research was supported by the Key Research and Development Plan Project of Ningxia Hui Autonomous Region (No. 2021BEG02027) and the Special Project for Cultivation and Development of Beijing Science and Technology Innovation Base (No. Z191100002819001).
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Research ethics: Not applicable.
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Author contributions: The authors have accepted responsibility for the entire content of this manuscript and approved its submission.
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Competing interests: The authors state no conflict of interest.
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Research funding: The Key Research and Development Plan Project of Ningxia Hui Autonomous Region (No. 2021BEG02027) and the Special Project for Cultivation and Development of Beijing Science and Technology Innovation Base (No. Z191100002819001).
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Data availability: Not applicable.
References
1. Zhao, L, Huang, S, Cai, X, Hong, J, Wang, S. A specific peptide with calcium chelating capacity isolated from whey protein hydrolysate. J Funct Foods 2014;10:46–53, https://doi.org/10.1016/j.jff.2014.05.013.Search in Google Scholar
2. Daengprok, W, Garnjanagoonchorn, W, Naivikul, O, Pornsinlpatip, P, Issigonis, K, Mine, Y. Chicken eggshell matrix proteins enhance calcium transport in the human intestinal epithelial cells, Caco-2. J Agric Food Chem 2003;51:6056–61, https://doi.org/10.1021/jf034261e.Search in Google Scholar PubMed
3. Huang, G, Ren, L, Jiang, J. Purification of a histidine-containing peptide with calcium binding activity from shrimp processing byproducts hydrolysate. Eur Food Res Tech 2011;232:281–7.10.1007/s00217-010-1388-2Search in Google Scholar
4. Pan, DD, Lu, HQ, Zeng, XQ. A newly isolated Ca binding peptide from whey protein. Int J Food Prop 2013;16:1127–34.10.1080/10942912.2011.576361Search in Google Scholar
5. Montserrat-de la Paz, S, Rodriguez-Martin, NM, Villanueva, A, Pedroche, J, Cruz-Chamorro, I, Millan, F, et al.. Evaluation of anti-inflammatory and atheroprotective properties of wheat gluten protein hydrolysates in primary human monocytes. Foods 2020;9:854.10.3390/foods9070854Search in Google Scholar PubMed PubMed Central
6. Liu, WY, Lu, J, Gao, F, Gu, RZ, Lin, F, Ren, DF, et al.. Preparation, characterization and identification of calcium-chelating Atlantic salmon (Salmo salar L.) ossein oligopeptides. Eur Food Res Tech 2015;241:851–60.10.1007/s00217-015-2510-2Search in Google Scholar
7. AOAC. Official methods of analysis of the Association of Official Analytical Chemists. Washington DC: Association of Official Analytical Chemists; 2002.Search in Google Scholar
8. Liu, WY, Feng, XW, Cheng, QL, Zhao, XH, Li, GM, Gu, RZ. Identification and action mechanism of low-molecular-weight peptides derived from the Atlantic salmon (Salmo salar L.) skin inhibiting angiotensin I-converting enzyme. Lebensm Wiss Technol 2021;150:111911.10.1016/j.lwt.2021.111911Search in Google Scholar
9. Yuan, B, Zhao, C, Cheng, C, Huang, DC, Cheng, SJ, Cao, CJ, et al.. A peptide-Fe(II) complex from Grifola frondosa protein hydrolysates and its immunomodulatory activity. Food Biosci 2019;32:100459, https://doi.org/10.1016/j.fbio.2019.100459.Search in Google Scholar
10. Wu, J, Ding, X. Characterization of inhibition and stability of soy-protein-derived angiotensin I-converting enzyme inhibitory peptides. Food Res Int 2002;35:367–75, https://doi.org/10.1016/s0963-9969(01)00131-4.Search in Google Scholar
11. Liu, WY, Zhang, JT, Miyakawa, T, Li, GM, Gu, RZ, Tanokura, M. Antioxidant properties and inhibition of angiotensin-converting enzyme by highly active peptides derived from wheat gluten. Sci Rep 2021;11:5206, https://doi.org/10.1038/s41598-021-84820-7.Search in Google Scholar PubMed PubMed Central
12. Lao, L, He, J, Liao, W, Zeng, C, Liu, G, Cao, Y, et al.. Casein calcium-binding peptides: preparation, characterization, and promotion of calcium uptake in Caco-2 cell monolayers. Process Biochem 2023;130:78–86.10.1016/j.procbio.2023.03.031Search in Google Scholar
13. Huang, W, Lan, Y, Liao, W, Lin, L, Liu, G, Xu, H, et al.. Preparation, characterization and biological activities of egg white peptides-calcium chelate. LWT - Food Sci Technol 2021;149:112035.10.1016/j.lwt.2021.112035Search in Google Scholar
14. Wang, X, Gao, A, Chen, Y, Zhang, X, Li, S, Chen, Y. Preparation of cucumber seed peptide-calcium chelate by liquid state fermentation and its characterization. Food Chem 2012;229:487–494.10.1016/j.foodchem.2017.02.121Search in Google Scholar PubMed
15. Hou, H, Wang, SK, Zhu, X, Li, QQ, Fan, Y, Cheng, D, et al.. A novel calcium-binding peptide from Antarctic krill protein hydrolysates and identification of binding sites of calcium-peptide complex. Food Chem 2018;243:389–95, https://doi.org/10.1016/j.foodchem.2017.09.152.Search in Google Scholar PubMed
16. Invernici, M, Trindade, IB, Cantini, F, Piccioli, M. Measuring transverse relaxation in highly paramagnetic systems. J Biomol NMR 2020;74:431–42.10.1007/s10858-020-00334-wSearch in Google Scholar PubMed PubMed Central
17. Akhtar, HMS, Riaz, A, Hamed, YS, Abdin, A, Chen, GJ, Wan, P, et al.. Production and characterization of CMC-based antioxidant and antimicrobial films enriched with chickpea hull polysaccharides. Int J Biol Macromol 2018;118:469–77, https://doi.org/10.1016/j.ijbiomac.2018.06.090.Search in Google Scholar PubMed
18. Wang, XZ, Zhang, Z, Xu, HY, Li, XY, Hao, XD. Preparation of sheep bone collagen peptide–calcium chelate using enzymolysis-fermentation methodology and its structural characterization and stability analysis. RSC Adv 2020;10:11624–33, https://doi.org/10.1039/d0ra00425a.Search in Google Scholar PubMed PubMed Central
19. Hu, G, Wang, D, Su, R, Corazzin, M, Liu, X, Sun, X, et al.. Calcium‑binding capacity of peptides obtained from sheep bone and structural characterization and stability of the peptide‑calcium chelate. J Food Meas Charact 2022;16:4934–4946.10.1007/s11694-022-01580-2Search in Google Scholar
20. Luo, JQ, Yao, XT, Soladoye, OP, Zhang, HY, Fu, Y. Phosphorylation modification of collagen peptides from fish bone enhances their calcium-chelating and antioxidant activity. Lwt 2022;155:112978, https://doi.org/10.1016/j.lwt.2021.112978.Search in Google Scholar
21. Sun, R, Liu, X, Yu, Y, Miao, J, Leng, K, Gao, H. Preparation process optimization, structural characterization and in vitro digestion stability analysis of Antarctic krill (Euphausia superba) peptides-zinc chelate. Food Chem 2021;340:128056, https://doi.org/10.1016/j.foodchem.2020.128056.Search in Google Scholar PubMed
22. Liu, FR, Wang, L, Wang, R, Chen, ZX. Calcium-binding capacity of wheat germ protein hydrolysate and characterization of peptide–calcium complex. J Agric Food Chem 2013;61:7537–44.10.1021/jf401868zSearch in Google Scholar PubMed
23. Shu, GW, Zhang, BW, Zhang, Q, Wan, HC, Li, H. Effect of temperature, pH, enzyme to substrate ratio, substrate concentration and time on the antioxidative activity of hydrolysates from goat milk casein by alcalase. AUCFT 2016;20:29–38, https://doi.org/10.1515/aucft-2016-0013.Search in Google Scholar
24. Bao, XL, Yuan, XY, Feng, GX, Zhang, ML, Ma, S. Structural characterization of calcium-binding sunflower seed and peanut peptides and enhanced calcium transport by calcium complexes in Caco-2 cells. J Sci Food Agric 2021;101:794–804.10.1002/jsfa.10800Search in Google Scholar PubMed
25. Vo, TDL, Pham, KT, Le, VMV, Lam, HH, Huynh, ON, Vo, BC. Evaluation of iron-binding capacity, amino acid composition, functional properties of Acetes japonicus proteolysate and identification of iron-binding peptides. Process Biochem 2020;91:374–86, https://doi.org/10.1016/j.procbio.2020.01.007.Search in Google Scholar
26. Peng, Z, Hou, H, Zhang, K, Li, BF. Effect of calcium-binding peptide from Pacific cod (Gadus macrocephalus) bone on calcium bioavailability in rats. Food Chem 2017;221:373–8, https://doi.org/10.1016/j.foodchem.2016.10.078.Search in Google Scholar PubMed
27. Bao, ZJ, Zhang, PL, Sun, N, Lin, SY. Elucidating the calcium-binding site, absorption activities, and thermal stability of egg white peptide-calcium chelate. Foods 2021;10:2565.10.3390/foods10112565Search in Google Scholar PubMed PubMed Central
28. Xu, Z, Zhu, ZX, Chen, H, Han, LY, Shi, PJ, Dong, XF, et al.. Application of a Mytilus edulis-derived promoting calcium absorption peptide in calcium phosphate cements for bone. Biomaterials 2022;282:121390, https://doi.org/10.1016/j.biomaterials.2022.121390.Search in Google Scholar PubMed
29. Kong, X, Xiao, ZQ, Chen, YH, Du, MD, Zhang, ZH, Wang, ZH, et al.. Calcium-binding properties, stability, and osteogenic ability of phosphorylated soy peptide-calcium chelate. Front Nutr 2023;10:1129548.10.3389/fnut.2023.1129548Search in Google Scholar PubMed PubMed Central
30. Sharma, VS. The stability constants of metal complexes of serine and threonine. BBA-Gen Subjects 1967;148:37–41, https://doi.org/10.1016/0304-4165(67)90276-0.Search in Google Scholar PubMed
31. Thompson, CC, Lai, RY. Threonine phosphorylation of an electrochemical peptide-based sensor to achieve improved uranyl ion binding affinity. Biosensors 2022;12:961, https://doi.org/10.3390/bios12110961.Search in Google Scholar PubMed PubMed Central
32. Neelam, C, Devi, TG, Karlo, T. Synthesis and characterization of metal complex amino acid using spectroscopic methods and theoretical calculation. J Mol Struct 2022;1250:131670.10.1016/j.molstruc.2021.131670Search in Google Scholar
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