Characterization of binding interactions between selected phenylpropanoid glycosides and trypsin

Food Chemistry

Volumn 243, Issue , 2018, Pages 118-124

  Feng, Yue ^a   Lv, Moyang ^b   Lu, YuQin ^a   Liu, Ke ^c   Liu, Lizhong ^a   He, Zhendan ^a   Wu, Kaimin ^a   Wang, Xinrong ^a   Zhang, Baoshuang ^a   Wu, Xuli ^a  

^a Shenzhen University School of Medicine   (China)

^b Shenzhen Foreign Languages School   (China)

^c XIAMEN UNIVERSITY   (China)

Author keywords

Inhibitory activity; Phenol protein binding; Phenylpropanoid glycoside; Secondary structure; Trypsin

Indexed keywords

BINDING ENERGY; BIOCHEMISTRY; HYDROGEN BONDS; POLYPHENOLIC COMPOUNDS; SPECTROSCOPIC ANALYSIS;

INHIBITORY ACTIVITY; PHENYLPROPANOID GLYCOSIDES; PROTEIN BINDING; SECONDARY STRUCTURES; TRYPSIN;

SUGARS;

ACTEOSIDE; GLYCOSIDE; LIPEDOSIDE A I; OSMANTHUSIDE B; PHENOL; PHENYLPROPANOID GLYCOSIDE DERIVATIVE; PLANT EXTRACT; POLYPHENOL DERIVATIVE; SYRINGALIDE A; SYRINGALIDE A 3' ALPHA LEVO RHAMNOPYRANOSIDE; TRYPSIN; UNCLASSIFIED DRUG; 1-PHENYLPROPANOL; PROPANOL; PROTEIN BINDING;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG BINDING SITE; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; IC50; LIPOPHILICITY; MOLECULAR DOCKING; PROTEIN CONFORMATION; PROTEIN CONTENT; PROTEIN INTERACTION; PROTEIN SECONDARY STRUCTURE;

GLYCOSIDES; PROPANOLS; PROTEIN BINDING; TRYPSIN;

EID: 85030154878     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2017.09.118     Document Type: Article

References (34)

1. Beauchemin, R., Soukpoékossi, C.N., Thomas, T.J., Thomas, T., Carpentier, R., Tajmirriahi, H.A., Polyamine analogues bind human serum albumin. Biomacromolecules 8:10 (2007), 3177–3183.
2. Brandl, T., Simic, O., Skaanderup, P.R., Namoto, K., Berst, F., Ehrhardt, C., Woelcke, J., Trypsin inhibitors for the treatment of pancreatitis. Bioorganic & Medicinal Chemistry Letters 26 (2016), 4340–4344.
3. Cao, H., Chen, X., Structures required of flavonoids for inhibiting digestive enzymes. Anti-cancer Agents in Medicinal Chemistry 12 (2012), 929–939.
4. Chen, R.C., Su, J.H., Yang, S.M., Li, J., Wang, T.J., Zhou, H., Effect of isoverbascoside, a phenylpropanoid glycoside antioxidant, on proliferation and differentiation of human gastric cancer cell. Acta Pharmacologica Sinica 23 (2002), 997–1001.
5. Cohen, S.D., Kennedy, J.A., Plant metabolism and the environment: implications for managing phenolics. Critical Reviews in Food Science & Nutrition 50 (2010), 620–643.
6. Díaz, A.M., Abad, M.J., Fernández, L., Silván, A.M., De Santos, J., Bermejo, P., Phenylpropanoid glycosides from Scrophularia scorodonia: In vitro anti-inflammatory activity. Life Sciences 74 (2004), 2515–2526.
7. He, Z.D., Lau, K.M., But, P.P., Jiang, R.W., Dong, H., Ma, S.C., Sun, H.D., Antioxidative glycosides from the leaves of Ligustrum robustum. Journal Of Natural Products 66:6 (2003), 851–854.
8. Kanakis, C.D., Hasni, I., Bourassa, P., Tarantilis, P.A., Polissiou, M.G., Tajmir-Riahi, H.A., Milk β-lactoglobulin complexes with tea polyphenols. Food Chemistry 127:3 (2011), 1046–1055.
9. Kang, H.M., Kim, J.H., Lee, M.Y., Son, K.H., Yang, D.C., Baek, N.I., Kwon, B.M., Relationship between flavonoid structure and inhibition of farnesyl protein transferase. Natural Product Research 18 (2004), 349–356.
10. Krimm, S., Bandekar, J., Vibrational spectroscopy and conformation of peptides, polypeptides, and proteins. Advances In Protein Chemistry 38 (1986), 181–364.
11. Leung, D., Abbenante, G., Fairlie, D.P., Protease inhibitors: Current status and future prospects. Cheminform 31 (2000), 305–341.
12. Liu, B., Xiao, H., Li, J., Geng, S., Ma, H., Liang, G., Interaction of phenolic acids with trypsin: Experimental and molecular modeling studies. Food Chemistry 228 (2017), 1–6.
13. Liu, Y., Zhang, G., Zeng, N., Hu, S., Interaction between 8-methoxypsoralen and trypsin: Monitoring by spectroscopic, chemometrics and molecular docking approaches. Spectrochimica Acta Part A Molecular & Biomolecular Spectroscopy 173 (2017), 188–195.
14. Mushtaq, M., Wanim, S.M., Polyphenols and human health – A review. International Journal of Pharma & Bio Sciences 4 (2013), 338–360.
15. Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J., AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry 30 (2009), 2785–2791.
16. National Center for Biotechnology Information (NCBI). (2017). PubChem Compound Database. https://pubchem.ncbi.nlm.nih.gov/compound.
17. Ozdal, T., Capanoglu, E., Altay, F., A review on protein–phenolic interactions and associated changes. Food Research International 51 (2013), 954–970.
18. Pan, J., Yuan, C., Lin, C., Jia, Z., Zheng, R., Pharmacological activities and mechanisms of natural phenylpropanoid glycosides. Pharmazie 58 (2004), 767–775.
19. Prigent, S.V., Gruppen, H., Visser, A.J., Van Koningsveld, G.A., De Jong, G.A., Voragen, A.G., Effects of non-covalent interactions with 5-O-caffeoylquinic acid (chlorogenic acid) on the heat denaturation and solubility of globular proteins. Journal of Agricultural & Food Chemistry 51 (2003), 5088–5095.
20. Rohn, S., Rawel, H.M., Kroll, J., Inhibitory effects of plant phenols on the activity of selected enzymes. Journal of Agriculture & Food Chemistry 50 (2002), 3566–3571.
21. Shi, W., Wang, Y., Zhang, H., Liu, Z., Fei, Z., Probing deep into the binding mechanisms of folic acid with a-amylase, pepsin and trypsin: An experimental and computational study. Food Chemistry 226 (2017), 128–134.
22. Susi, H., Examination of the secondary structure of proteins by deconvolved FTIR spectra. Biopolymers 25 (1986), 469–487.
23. Susi, H., Byler, D.M., Resolution-enhanced Fourier transform infrared spectroscopy of enzymes. 1986, MTP Press.
24. Tayeh, N., Rungassamy, T., Albani, J.R., Fluorescence spectral resolution of tryptophan residues in bovine and human serum albumins. Journal of Pharmaceutical & Biomedical Analysis 50 (2009), 107–116.
25. Wang, J., Liu, R., Qin, P., Toxic interaction between acid yellow 23 and trypsin: spectroscopic methods coupled with molecular docking. Journal of Biochemical & Molecular Toxicology 26:9 (2012), 360–367.
26. Wang, W.X., Li, T.X., Ma, H., Zhang, J.F., Jia, A.Q., Tumoral cytotoxic and antioxidative phenylpropanoid glycosides in Smilax riparia A. DC. Journal of Ethnopharmacology 149 (2013), 527–532.
27. Whitmore, L., DICHROWEB, an online server for protein secondary structure analyses from circular dichroism spectroscopic data. Nucleic Acids Research 32:1 (2004), 668–673.
28. Wu, X., He, W., Yao, L., Zhang, H., Liu, Z., Wang, W., Cao, J., Characterization of binding interactions of (-)-epigallocatechin-3-gallate from green tea and lipase. Journal of Agricultural & Food Chemistry 61 (2013), 8829–8835.
29. Wu, X., Wang, W.P., Zhu, T., Liang, T., Lu, F.Q., He, W., Gao, K., Phenylpropanoid glycoside inhibition of pepsin, trypsin and α-chymotrypsin enzyme activity in Kudingcha leaves from Ligustrum purpurascens. Food Research International 54 (2013), 1376–1382.
30. Wu, X., Raje, D., Wu, H., Liu, Z., He, Q., Zeng, X., Studies on the interaction of -epigallocatechin-3-gallate from green tea with bovine β-lactoglobulin by spectroscopic methods and docking. International Journal Of Dairy Technology 66 (2013), 7–13.
31. Xiao, J., Ni, X., Kai, G., Chen, X., A review on structure-activity relationship of dietary polyphenols inhibiting α-amylase. Critical Reviews In Food Science And Nutrition 53 (2013), 497–506.
32. Xiao, J., Shi, J., Cao, H., Wu, S., Ren, F.L., Xu, M., Analysis of binding interaction between puerarin and bovine serum albumin by multi-spectroscopic method. Journal of Pharmaceutical and Biomedical Analysis 45 (2007), 609–615.
33. Zeng, H.J., Wang, Y.P., Yang, R., You, J., Qu, L.B., Inhibitory effects of daidzein and genistein on trypsin: insights from spectroscopic and molecular docking studies. International Journal of Biological Macromolecules 89 (2016), 336–343.
34. Zhang, L., Liao, C.C., Huang, H.C., Shen, Y.C., Yang, L.M., Kuo, Y.H., Antioxidant phenylpropanoid glycosides from Smilax bracteata. Phytochemistry 69:6 (2008), 1398–1404.