Evaluation of epigallocatechin gallate (EGCG) to remove Pb(II) using spectroscopic and quantum chemical calculation method

  • Dongfang Wang
  • Daeik Kim
  • Chul-Ho Shin
  • Yufeng Zhao
  • Joon-Seok ParkEmail author
  • Moonhee RyuEmail author
Thematic Issue


Recently, (−)-epigallocatechin-3-gallate (EGCG) has been highly reviewed for its beneficial chemical properties. In this study, the formation mechanism of the complexes obtained by EGCG and Pb(II) was investigated in an aqueous solution, using a molar ratio method with the verification of UV–Vis spectrometry, scanning electron microscope (SEM), quantum calculation, and Fourier transform infrared spectrometry (FTIR). The SEM results showed that the morphology of EGCG changed from spherical or approximately spherical shapes to massive structures. The molar ratio method and the UV–Vis absorption spectroscopy were effective in determining the complex composition, and the resulting data indicated that the EGCG–Pb(II) complex was formed with an optimum EGCG:Pb molar ratio of 1:2 at pH 5.0. A quantum computation with Parametric Method 7 (PM7) and FTIR spectra were useful to identify the molecular structure of the complex. The results evidently exhibited the changes of molecular structure of EGCG before versus after the complexation reaction, and a complex formation was observed. In general, this work would be favorable to the further research on complexation of EGCG with other metal ions. Such complexes will make a reference for treating wastewater streams polluted by toxic metals.


Epigallocatechin gallate (EGCG) Lead Complexation Stoichiometry Crosslink 



  1. Abib RT, Peres KC, Barbosa AM et al (2011) Epigallocatechin-3-gallate protects rat brain mitochondria against cadmium-induced damage. Food Chem Toxicol 49:2618–2623CrossRefGoogle Scholar
  2. Baes CF, Mesmer RE (1976) The hydrolysis of cations. Wiley, New YorkGoogle Scholar
  3. Bansal S, Choudhary S, Sharma M et al (2013) Tea: a native source of antimicrobial agents. Food Res Int 53:568–584CrossRefGoogle Scholar
  4. Bartholome A, Kampkötter A, Tanner S, Sies H, Klotz LO (2010) Epigallocatechin gallate-induced modulation of FoxO signaling in mammalian cells and C. elegans: FoxO stimulation is masked via PI3K/Akt activation by hydrogen peroxide formed in cell culture. Arch Biochem Biophys 501:58–64CrossRefGoogle Scholar
  5. Bazinet L, Arayafarias M, Doyen A, Trudel D, Têtu B (2010) Effect of process unit operations and long-term storage on catechin contents in EGCG-enriched tea drink. Food Res Int 43:1692–1701CrossRefGoogle Scholar
  6. Boudet AC, Cornard JP, Merlin JC (2000) Conformational and spectroscopic investigation of 3-hydroxyflavone–aluminium chelates. Spectrochim Acta A 56:829–839CrossRefGoogle Scholar
  7. Cabrera C, Artacho R, Giménez R (2006) Beneficial effects of green tea—a review. J Am Coll Nutr 25:79–99CrossRefGoogle Scholar
  8. Chang JH, Chang SL, Hong PD, Chen PN, Hsu CH, Lu YY, Chen YC (2017) Epigallocatechin-3-gallate modulates arrhythmogenic activity and calcium homeostasis of left atrium. Int J Cardiol 236:174–180CrossRefGoogle Scholar
  9. Chen L, Yang X, Jiao H, Zhao B (2004) Effect of Tea Catechins on the Change of Glutathione Levels Caused by Pb++ in PC12 Cells. Chem Res Toxicol 17:922–928CrossRefGoogle Scholar
  10. Ghosh KS, Maiti TK, Mandal A, Dasgupta S (2006) Copper complexes of (−)-epicatechin gallate and (−)-epigallocatechin gallate act as inhibitors of `Ribonuclease A. Febs Lett 580:4703–4708CrossRefGoogle Scholar
  11. Ghosh KS, Sahoo BK, Jana D, Dasgupta S (2008) Studies on the interaction of copper complexes of (−)-epicatechin gallate and (−)-epigallocatechin gallate with calf thymus DNA. J Inorg Biochem 102:1711–1718CrossRefGoogle Scholar
  12. Holten-Andersen N, Harrington MJ, Birkedal H, Lee BP, Messersmith PB, Lee KYC, Waite JH (2011) pH-induced metal-ligand cross-links inspired by mussel yield self-healing polymer networks with near-covalent elastic moduli. P Natl Acad Sci USA 108:2651–2655CrossRefGoogle Scholar
  13. Kanakis CD, Hasni I, Bourassa P, Tarantilis PA, Polissiou MG, Tajmir-Riahi HA (2011) Milk β-lactoglobulin complexes with tea polyphenols. Food Chem 127:1046–1055CrossRefGoogle Scholar
  14. Kao YH, Chang HH, Lee MJ, Chen CL (2006) Tea, obesity, and diabetes. Mol Nutr Food Res 50:188–210CrossRefGoogle Scholar
  15. Kim D, Lai H-T, Chilingar GV, Yen TF (2006) Geopolymer formation and its unique properties. Environ Geol 51:103–111CrossRefGoogle Scholar
  16. Kim D, Quinlan M, Yen TF (2009) Encapsulation of lead from hazardous CRT glass wastes using biopolymer cross-linked concrete systems. Waste Manag 29:321–328CrossRefGoogle Scholar
  17. Kim D, Park JS, Yen TF (2012) Feasibility study on cross-linked biopolymeric concrete encapsulating selenium glass wastes. J Air Waste Manage 62:898–904CrossRefGoogle Scholar
  18. Kuo CY, Lin HY (2009) Adsorption of aqueous cadmium (II) onto modified multi-walled carbon nanotubes following microwave/chemical treatment. Desalination 249:792–796CrossRefGoogle Scholar
  19. Kushiyama M, Shimazaki Y, Murakami M, Yamashita Y (2009) Relationship between intake of green tea and periodontal disease. J Periodontol 80:372–377CrossRefGoogle Scholar
  20. Lavelli V, Vantaggi C, Corey M, Kerr W (2010) Formulation of a dry green tea-apple product: study on antioxidant and color stability. J Food Sci 75:184–190CrossRefGoogle Scholar
  21. Lee BS, Lee CC, Lin HP et al (2016) A functional chitosan membrane with grafted epigallocatechin-3-gallate and lovastatin enhances periodontal tissue regeneration in dogs. Carbohyd Polym 151:790–802CrossRefGoogle Scholar
  22. Li MJ, Yin YC, Wang J, Jiang YF (2014) Green tea compounds in breast cancer prevention and treatment. World J Clin Oncol 5:520–528CrossRefGoogle Scholar
  23. Li Z, Kong Y, Ge Y (2015) Synthesis of porous lignin xanthate resin for Pb2+ removal from aqueous solution. Chem Eng J 270:229–234CrossRefGoogle Scholar
  24. Liu Y, Liu Z, Gao J et al (2011) Selective adsorption behavior of Pb(II) by mesoporous silica SBA-15-supported Pb(II)-imprinted polymer based on surface molecularly imprinting technique. J Hazard Mater 186:197–205CrossRefGoogle Scholar
  25. Lu LL, Li YH, Lu XY (2009) Kinetic study of the complexation of gallic acid with Fe (II). Spectrochim Acta A 74:829–834CrossRefGoogle Scholar
  26. Nagle DG, Ferreira D, Zhou YD (2006) Epigallocatechin-3-gallate (EGCG): Chemical and biomedical perspectives. Phytochemistry 67:1849–1855CrossRefGoogle Scholar
  27. Pirker KF, Baratto MC, Basosi R, Goodman BA (2012) Influence of pH on the speciation of copper (II) in reactions with the green tea polyphenols, epigallocatechin gallate and gallic acid. J Inorg Biochem 112:10–16CrossRefGoogle Scholar
  28. Qiu Y, Cheng H, Xu C, Sheng GD (2008) Surface characteristics of crop-residue-derived black carbon and lead(II) adsorption. Water Res 42:567–574CrossRefGoogle Scholar
  29. Rahmani AH, Al-shabrmi FM, Allemailem KS, Aly SM, Khan MA (2015) Implications of green tea and its constituents in the prevention of cancer via the modulation of cell signalling pathway. Biomed Res Int 2015:1–12Google Scholar
  30. Ren Y, Li N, Feng J, Luan T, Wen Q, Li Z, Zhang M (2012) Adsorption of Pb(II) and Cu(II) from aqueous solution on magnetic porous ferrospinel MnFe2O4. J Colloid Interf Sci 367:415–421CrossRefGoogle Scholar
  31. Sang S, Lambert JD, Ho CT, Yang CS (2011) The chemistry and biotransformation of tea constituents. Pharmacol Res 64:87–99CrossRefGoogle Scholar
  32. Schramm L (2013) Going green: the role of the green tea component EGCG in chemoprevention. J Carcinogene Mutagene 4:1000142CrossRefGoogle Scholar
  33. Sedó J, Saiz-Poseu J, Busqué F, Ruiz-Molina D (2013) Catechol-based biomimetic functional materials. Adv Mater 25:653–701CrossRefGoogle Scholar
  34. Severino JF, Goodman BA, Kay CWM, Stolze K, Tunega D, Reichenauer TG, Pirker KF (2009) Free radicals generated during oxidation of green tea polyphenols: electron paramagnetic resonance spectroscopy combined with density functional theory calculations. Free Radical Bio Med 46:1076–1088CrossRefGoogle Scholar
  35. Siddiqui IA, Adhami VM, Bharali DJ et al (2009) Introducing nanochemoprevention as a novel approach for cancer control: proof of principle with green tea polyphenol epigallocatechin-3-gallate. Cancer Res 69:1712–1716CrossRefGoogle Scholar
  36. Siripatrawan U, Noipha S (2012) Active film from chitosan incorporating green tea extract for shelf life extension of pork sausages. Food Hydrocolloid 27:102–108CrossRefGoogle Scholar
  37. Tang DW, Yu SH, Ho YC (2013) Characterization of tea catechins-loaded nanoparticles prepared from chitosan and an edible polypeptide. Food Hydrocolloid 30:33–41CrossRefGoogle Scholar
  38. Vuong QV, Durel M, Roach PD, Stathopoulos CE (2011) Preliminary study on the fortification of tofu with green tea catechins. Int Food Res J 18:1553–1557Google Scholar
  39. Wang R, Zhou W, Jiang X (2008) Reaction kinetics of degradation and epimerization of epigallocatechin gallate (EGCG) in aqueous system over a wide temperature range. J Agr Food Chem 56:2694–2701CrossRefGoogle Scholar
  40. Wang D, Taylor EW, Wang Y, Wan X, Zhang J (2012) Encapsulated nanoepigallocatechin-3-gallate and elemental selenium nanoparticles as paradigms for nanochemoprevention. Int J Nanomed 7:1711–1721Google Scholar
  41. Wang K, Chen Q, Lin Y, Yu S, Lin H, Huang J, Liu Z (2016) Separation of catechins and O-methylated (−)-epigallocatechin gallate using polyamide thin-layer chromatography. J Chromatogr B 1017:221–225CrossRefGoogle Scholar
  42. Wei H, Meng Z (2011) Protective effects of epigallocatechin-3-gallate against lead-induced oxidative damage. Hum Exp Toxicol 30:1521–1528CrossRefGoogle Scholar
  43. Wei Y, Chen P, Ling T et al (2016) Certain (−)-epigallocatechin-3-gallate (EGCG) auto-oxidation products (EAOPs) retain the cytotoxic activities of EGCG. Food Chem 204:218–226CrossRefGoogle Scholar
  44. Weng CH, Huang CP (2004) Adsorption characteristics of Zn(II) from dilute aqueous solution by fly ash. Colloid Surfaces A 247:137–143CrossRefGoogle Scholar
  45. Xu D, Tan X, Chen C, Wang X (2008) Removal of Pb(II) from aqueous solution by oxidized multiwalled carbon nanotubes. J Hazard Mater 154:407–416CrossRefGoogle Scholar
  46. Yang CS, Hong J (2013) Prevention of chronic diseases by tea: possible mechanisms and human relevance. Annu Rev Nutr 33:161–181CrossRefGoogle Scholar
  47. Yang CS, Lambert JD, Sang S (2009) Antioxidative and anti-carcinogenic activities of tea polyphenols. Arch Toxicol 83:11–21CrossRefGoogle Scholar
  48. Yang W, Liu F, Xu C, Yuan F, Gao Y (2014) Molecular interaction between (–)-epigallocatechin-3-gallate and bovine lactoferrin using multi-spectroscopic method and isothermal titration calorimetry. Food Res Int 64:141–149CrossRefGoogle Scholar
  49. Zhang H, Luo R, Li W et al (2015) Epigallocatechin gallate (EGCG) induced chemical conversion coatings for corrosion protection of biomedical MgZnMn alloys. Corros Sci 94:305–315CrossRefGoogle Scholar
  50. Zhou L, Elias RJ (2013) Antioxidant and pro-oxidant activity of (−)-epigallocatechin-3-gallate in food emulsions: Influence of pH and phenolic concentration. Food Chem 138:1503–1509CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Division of Biotechnology, College of Environmental and Bioresource SciencesChonbuk National UniversityIksanSouth Korea
  2. 2.Seohae Environment Science InstituteJeonjuSouth Korea
  3. 3.EST & ES, Inc.FullertonUSA
  4. 4.Division of Semiconductor and Chemical EngineeringChonbuk National UniversityJeonjuSouth Korea
  5. 5.Department of Earth and Environmental EngineeringKangwon National UniversitySamcheokSouth Korea

Personalised recommendations