Characterization of binding interactions of (-)-epigallocatechin-3-gallate from green tea and lipase

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 37, 2013, Pages 8829-8835

  Wu, Xuli ^a   He, Weiyi ^a   Yao, Li ^a   Zhang, Haiping ^b   Liu, Zhigang ^a   Wang, Wenpu ^a   Ye, Ye ^a   Cao, Jijuan ^c  

^a Shenzhen University   (China)

^b XIAMEN UNIVERSITY   (China)

^c Liaoning Entry Exit Inspection and Quarantine Bureau   (China)

Author keywords

epigallocatechin gallate; green tea; interaction; lipase; obesity

Indexed keywords

EPIGALLOCATECHIN GALLATE; EPIGALLOCATECHIN-3-GALLATE; GREEN TEA; HYDROGEN BONDING INTERACTIONS; INTERACTION; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR CONFORMATION; OBESITY;

BINDING ENERGY; FLUORESCENCE SPECTROSCOPY; LIPASES;

HYDROGEN BONDS;

CATECHIN; DRUG DERIVATIVE; EPIGALLOCATECHIN GALLATE; PLANT EXTRACT; TRIACYLGLYCEROL LIPASE;

ANIMAL; ARTICLE; CAMELLIA SINENSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; KINETICS; PROTEIN BINDING; SWINE; THERMODYNAMICS;

ANIMALS; CAMELLIA SINENSIS; CATECHIN; HYDROGEN BONDING; KINETICS; LIPASE; MODELS, MOLECULAR; PLANT EXTRACTS; PROTEIN BINDING; SWINE; THERMODYNAMICS;

EID: 84884468885     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf401779z     Document Type: Article

References (49)

1. Cheng, T. O. Obesity crisis comprised of danger and opportunity J. Am. Diet. Assoc. 2004, 104, 1546
2. Wolfram, S.; Wang, Y.; Thielecke, F. Anti-obesity effects of green tea: from bedside to bench mol Nutr. Food Res. 2006, 50, 176-187
3. Kavanagh, K. T.; Hafer, L. J.; Kim, D. W.; Mann, K. K.; Sherr, D. H.; Rogers, A. E.; Sonenshein, G. E. Green tea extracts decrease carcinogen-induced mammary tumor burden in rats and rate of breast cancer cell proliferation in culture J. Cell Biochem. 2001, 82, 387-398
4. Sueoka, N.; Suganuma, M.; Sueoka, E.; Okabe, S.; Matsuyama, S.; Imai, K.; Nakachi, K.; Fujiki, H. A new function of green tea: prevention of lifestyle related diseases Ann. N. Y. Acad. Sci. 2001, 928, 274-280
5. Dona, M.; Dell'Aica, I.; Calabrese, F.; Benelli, R.; Morini, M.; Albini, A.; Garbisa, S. Neutrophil restraint by green tea: inhibition of inflammation, associated angiogenesis, and pulmonary fibrosis J. Immunol. 2003, 170, 4335-4341
6. Haqqi, T. M.; Anthony, D. D.; Gupta, S.; Ahmad, N.; Lee, M. S.; Kumar, G. K.; Mukhtar, H. Prevention of collagen-induced arthritis in mice by a polyphenolic fraction from green tea Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4524-4529
7. Sudano, R. A.; Blanco, A. R.; Giuliano, F.; Rusciano, D.; Enea, V. Epigallocatechin-gallate enhances the activity of tetracycline in staphylococci by inhibiting its efflux from bacterial cells Antimicrob. Agents Chemother. 2004, 48, 1968-1973
8. Sartippour, M. R.; Shao, Z. M.; Heber, D.; Beatty, P.; Zhang, L.; Liu, C.; Ellis, L.; Liu, W.; Go, V. L.; Brooks, M. N. Green tea inhibits vascular endothelial growth factor (VEGF) induction in human breast cancer cells J. Nutr. 2002, 132, 2307-2311
9. Osada, K.; Takahashi, M.; Hoshina, S.; Nakamura, M.; Nakamura, S.; Sugano, M. Tea catechins inhibit cholesterol oxidation accompanying oxidation of low density lipoprotein in vitro Comp. Biochem. Physiol. Part C: Toxicol. Pharmacol. 2001, 128, 153-164
10. Ho, C. T.; Chen, Q. Y.; Shi, H.; Zhang, K.-Q.; Rosen, R. T. Antioxidant effect of polyphenol extract prepared from various Chinese teas Prev. Med. 1992, 21, 520-525
11. Graham, H. N. Green tea composition, consumption, and polyphenol chemistry Prev. Med. 1992, 21, 334-350
12. Kilmartin, P. A.; Hsu, C. F. Characterisation of polyphenols in green, oolong,and black teas, and in coffee, using cyclic voltammetry Food Chem. 2003, 82, 501-512
13. By, Y. S.; Noriyuki, M.; Mamoru, I. Health-promoting effects of green tea Proc. Jpn. Acad. Ser. B: Phys. Biol. Sci. 2012, 88, 88-101
14. Sabu, M. C.; Priya, T. T.; Ramadasan, K.; Ikuo, N. Beneficial effects of green tea: a literature review Chinese Med. 2010, 5, 13-22
15. Sae-tan, S.; Grove, K. A.; Lambert, J. D. Weight control and prevention of metabolic syndrome by green tea Pharmacol. Res. 2011, 64, 146-154
16. Basu, A.; Sanchez, K.; Leyva, M. J.; Wu, M.; Betts, N. M.; Aston, C. E.; Lyons, T. J. Green tea supplementation affects body weight, lipids, and lipid peroxidation in obese subjects with metabolic syndrome J. Am. Coll. Nutr. 2010, 29, 31-40
17. Kao, Y. H.; Chang, H. H.; Lee, M. J.; Chen, C. L. Tea, obesity, and diabetes Mol. Nutr. Food Res. 2006, 50, 188-210
18. Thielecke, F.; Boschmann, M. The potential role of green tea catechins in the prevention of the metabolic syndrome-a review Phytochemistry 2009, 70, 11-24
19. Juhel, C.; Armand, M.; Pafumi, Y.; Rosier, C.; Vandermander, J.; Lairon, D. Green tea extract (ar25) inhibits lipolysis of triglycerides in gastric and duodenal medium in vitro J. Nutr. Biochem. 2000, 11, 45-51
20. Shishikura, Y.; Khokhar, S.; Murray, B. S. Effects of tea polyphenols on emulsification of olive oil in a small intestine model system J. Agric. Food Chem. 2006, 54, 1906-1913
21. Armand, M.; Pasquier, B.; André, M.; Borel, P.; Senft, M.; Peyrot, J.; Salducci, J.; Portugal, H.; Jaussan, V.; Lairon, D. Digestion and absorption of 2 fat emulsions with different droplet sizes in the human digestive tract Am. J. Clin. Nutr. 1999, 70, 1096-1106
22. Shi, B.; He, X. Q.; Haslam, E. Gelatin-polyphenol interaction Am. Leather Chem. Assoc. 1994, 89, 98-104
23. Siebert, K. J.; Troukhanova, N. V.; Lynn, P. Y. Nature of polyphenol-protein interactions J. Agric. Food Chem. 1996, 44, 80-85
24. He, Q.; Lv, Y. P.; Yao, K. Effects of tea polyphenols on the activities of α-amylase, pepsin, trypsin and lipase Food Chem. 2006, 101, 1178-1182
25. Koo, S. I.; Sang, K. Green tea as inhibitor of the intestinal absorption of lipids: potential mechanism for its lipid-lowering effect J. Nutr. Biochem 2007, 18, 179-183
26. Mosmuller, E. W. J.; Van Heemst, J. D. H.; Van Delden, C. J.; Franssen, M. C. R.; Engbersen, J. F. J. A new spectrophotometric method for the detection of lipase activity using 2,4-dinitrophenyl butyrate as a substrate Biocatalysis 1992, 5, 279-287
27. Whitmore, L.; Wallace, B. A. DICHROWEB, an online server for protein secondary structure analyses from circular dichroism spectroscopic data Nucleic Acids Res. 2004, 32, 668-673
28. Charlton, A. J.; Baxter, N. J.; Khan, M. L.; Moir, A. J.; Haslam, E.; Davies, A. P.; Williamson, M. P. Polyphenols/peptide binding and precipitation J. Agric. Food Chem. 2002, 50, 1593-1601
29. Wu, X. L.; Wu, H.; Liu, M. X.; Liu, Z. G.; Xu, H.; Lai, F. R. Analysis of binding interaction between (-)-epigallocatechin (EGC) and β-lactoglobulin by multi-spectroscopic method Spectrochim. Acta A 2011, 82, 164-168
30. Gokara, M.; Sudhamalla, B.; Amooru, D. G.; Subramanyam, R. Molecular interaction studies of trimethoxy flavone with human serum albumin PLoS One 2010, 5, e8834
31. Frazier, R. A.; Papadopoulou, A.; Green, R. J. Isothermal titration calorimetry study of epicatechin binding to serum albumin J. Pharm. Biomed. Anal. 2006, 41, 1602-1605
32. Ross, P. D.; Subramanian, S. Thermodynamics of protein association reactions: forces contributing to stability Biochemistry 1981, 20, 3096-3102
33. 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 Chem. 2011, 127, 1046-1055
34. Tushar, K. M.; Kalyan, S. G.; Swagata, D. Interaction of (-)-epigallocatechin-3-gallate with humanserum albumin: fluorescence, fourier transform infrared,circular dichroism, and docking studies Proteins 2006, 64, 355-362
35. Zerrin, Y.; Elif, A.; Yasar, K. E. Characterization of binding interactions between green tea flavanoids and milk proteins Food Chem. 2010, 121, 450-456
36. Wu, X. L.; Dey, R.; Wu, H.; Liu, Z. G.; He, Q. Q.; Zeng, X. J. Studies on the interaction of EGCG with bovine β-lactoglobulin by spectroscopic methods and docking Int. J. Dairy Technol. 2013, 65, 7-13
37. Venyaminov, S. Y.; Vassilenko, K. S. Determination of protein tertiary structure class from circular dichroism spectra Anal. Biochem. 1994, 222, 176-184
38. Krejci, E.; Duval, N.; Chatonnet, A.; Vincens, P.; Massoulie, J. Cholinesterase-like domains in enzymes and structure proteins: functional and evolutionary relationships and identification of a catalytically essential aspartic acid Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6647-6651
39. Piekarska, B.; Skowronek, M.; Rybarska, J.; Stopa, B.; Roterman, I.; Konieczny, L. Congo red-stabilized intermediates in the lambda light chain transition from native to molten state Biochimie 1996, 78, 183-189
40. Andras, F. S.; Brian, C. B.; Takuji, T.; Yada, R. Y. Understanding the structure-function role of specific catalytic residues in a model food related enzyme: pepsin Enzyme Microb. Technol. 2007, 40, 1175-1180
41. Suzuki, Y.; Miyoshi, N.; Isemura, M. Health-promoting effects of green tea Proc. Jpn. Acad. Ser. B: Phys. Biol. Sci. 2012, 88, 88-101
42. 19F NMR Biochemistry 2013, 52, 1903-1912
43. 19F nuclear magnetic resonance-detected kinetics of monomer consumption Biochemistry 2012, 51, 8154-8162
44. DeToma, A. S.; Salamekh, S.; Ramamoorthy, A.; Lim, M. H. Misfolded proteins in Alzheimer's disease and type II diabetes Chem. Soc. Rev. 2012, 21, 608-621
45. Brender, J.; Salamekh, S.; Ramamoorthy, A. Membrane-disruption and early events in the aggregation of the diabetes related peptide IAPP from a molecular perspective Acc. Chem. Res. 2012, 116, 3650-3658
46. Popovych, N.; Brender, J. R.; Soong, R.; Vivekanandan, S.; Hartman, K.; Basrur, V.; Macdonald, P. M.; Ramamoorthy A site specific interaction of the polyphenol EGCG with the SEVI amyloid precursor peptide PAP(248-286) J. Phys. Chem. B 2012, 116, 3650-3658
47. Hyung, S. J.; DeToma, A. S.; Brender, J. R.; Lee, S.; Vivekanandan, S.; Kochi, A.; Choi, J. S.; Ramamoorthy, A.; Ruotolo, B. T.; Lim, M. H. Insights into antiamyloidogenic properties of the green tea extract (-)-epigallocatechin- 3-gallate toward metal-associated amyloid-β species Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 3743-3748
48. Huang, R.; Vivekanandan, S.; Brender, J. R.; Abe, Y.; Naito, A.; Ramamoorthy, A. NMR characterization of monomeric and oligomeric conformations of human calcitonin and its interaction with EGCG J. Mol. Biol. 2012, 416, 108-120
49. Porat, Y.; Abramowitz, A.; Gazit, E. Inhibition of amyloid fibril formation by polyphenols: structural similarity and aromatic interactions as a common inhibition mechanism Chem. Biol. Drug Des. 2006, 671, 27-37