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Journal of Food Science and Technology

, Volume 54, Issue 3, pp 770–777 | Cite as

The effective and selective separation of (−)-epigallocatechin gallate by molecularly imprinted chitosan beads

Original Article

Abstract

The ()-epigallocatechin gallate (EGCG) imprinted chitosan beads (EICBs) were fabricated for the effective and selective separation of EGCG. The EGCG molecules interacted with the amino groups of chitosan in the imprinting process, resulting in a highly porous structure of EICBs and more adsorption sites. Consequently, EICBs exhibited better adsorption performance than non-imprinted chitosan beads. The maximum adsorption capacity of EGCG onto EICBs reached 135.50 mg/g at 313 K. The imprinting factor of EICBs was 4.22, indicating that EICBs possess good recognition ability and selectivity for EGCG. After five cycles of reuse, only a slight decrease (7.77%) in the adsorption capacity was observed, demonstrating the satisfactory reusability of EICBs. Furthermore, the adsorption of EGCG onto EICBs is deduced to be the monolayer adsorption on an energetically homogeneous surface; the hydrogen bonding between EGCG and EICBs is the main driving force for the adsorption. Our studies suggest that EICBs have a great potential for the effective and selective separation of EGCG.

Keywords

()-Epigallocatechin gallate Chitosan Molecular imprinting technique Adsorption 

Notes

Acknowledgements

This work was supported by the Natural Science Foundation of Hebei Province (No. B2016202111).

References

  1. Babel S, Kurniawan TA (2003) Low-cost adsorbents for heavy metals uptake from contaminated water: a review. J Hazard Mater 97:219–243CrossRefGoogle Scholar
  2. Bansal S et al (2013) Tea: a native source of antimicrobial agents. Food Res Int 53:568–584CrossRefGoogle Scholar
  3. Chen CY, Yang CY, Chen AH (2011) Biosorption of Cu(II), Zn(II), Ni(II) and Pb(II) ions by cross-linked metal-imprinted chitosans with epichlorohydrin. J Environ Manag 92:796–802CrossRefGoogle Scholar
  4. Chen S, Luo ZM, Ma XL, Xue LQ, Lan HX, Zhang WB (2012) Efficient separation and purification of epigallocatechin gallate (EGCG) based on EGCG-imprinted polymer prepared with chitosan as matrix. Anal Lett 45:2300–2309CrossRefGoogle Scholar
  5. Crini G (2006) Non-conventional low-cost adsorbents for dye removal: a review. Bioresour Technol 97:1061–1085CrossRefGoogle Scholar
  6. Dube A, Nicolazzo JA, Larson I (2010) Chitosan nanoparticles enhance the intestinal absorption of the green tea catechins (+)-catechin and (−)-epigallocatechin gallate. Eur J Pharm Sci 41:219–225CrossRefGoogle Scholar
  7. Dube A, Nicolazzo JA, Larson I (2011) Chitosan nanoparticles enhance the plasma exposure of (−)-epigallocatechin gallate in mice through an enhancement in intestinal stability. Eur J Pharm Sci 44:422–426CrossRefGoogle Scholar
  8. Gadkari PV, Balarman M, Kadimi US (2015) Polyphenols from fresh frozen tea leaves (Camellia assamica L.), by supercritical carbon dioxide extraction with ethanol entrainer—application of response surface methodology. J Food Sci Technol 52:720–730CrossRefGoogle Scholar
  9. Gao R, Liu H, Peng Z, Wu Z, Wang Y, Zhao G (2012) Adsorption of (−)-epigallocatechin-3-gallate (EGCG) onto oat β-glucan. Food Chem 132:1936–1943CrossRefGoogle Scholar
  10. Ho YS (2006) Review of second-order models for adsorption systems. J Hazard Mater 136:681–689CrossRefGoogle Scholar
  11. Jiang R, Fu Y-Q, Zhu H-Y, Yao J, Xiao L (2012) Removal of methyl orange from aqueous solutions by magnetic maghemite/chitosan nanocomposite films: adsorption kinetics and equilibrium. J Appl Polym Sci 125:E540–E549CrossRefGoogle Scholar
  12. Kim J-H, Lee K-H (1998) Effect of PEG additive on membrane formation by phase inversion. J Membr Sci 138:153–163CrossRefGoogle Scholar
  13. Liu Y (2009) Is the free energy change of adsorption correctly calculated? J Chem Eng Data 54:1981–1985CrossRefGoogle Scholar
  14. Liu Y 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
  15. Liu Y, Bai Q, Lou S, Di D, Li J, Guo M (2012) Adsorption characteristics of (−)-epigallocatechin gallate and caffeine in the extract of waste tea on macroporous adsorption resins functionalized with chloromethyl, amino, and phenylamino groups. J Agric Food Chem 60:1555–1566CrossRefGoogle Scholar
  16. López de Lacey AM, Pérez-Santín E, López-Caballero ME, Montero P (2014) Survival and metabolic activity of probiotic bacteria in green tea. LWT-Food Sci Technol 55:314–322CrossRefGoogle Scholar
  17. Min K-j, Kwon TK (2014) Anticancer effects and molecular mechanisms of epigallocatechin-3-gallate. Integr Med Res 3:16–24CrossRefGoogle Scholar
  18. Nantasenamat C, Isarankura-Na-Ayudhya C, Naenna T, Prachayasittikul V (2007) Quantitative structure-imprinting factor relationship of molecularly imprinted polymers. Biosens Bioelectron 22:3309–3317CrossRefGoogle Scholar
  19. Ngah WS, Fatinathan S (2010) Adsorption characterization of Pb(II) and Cu(II) ions onto chitosan-tripolyphosphate beads: kinetic, equilibrium and thermodynamic studies. J Environ Manage 91:958–969CrossRefGoogle Scholar
  20. Oepen Bv, Kördel W, Klein W (1991) Sorption of nonpolar and polar compounds to soils: processes, measurements and experience with the applicability of the modified OECD-Guideline 106. Chemosphere 22:285–304CrossRefGoogle Scholar
  21. Reygaert WC (2014) The antimicrobial possibilities of green tea. Front Microbiol 5:434CrossRefGoogle Scholar
  22. Saklar S, Ertas E, Ozdemir IS, Karadeniz B (2015) Effects of different brewing conditions on catechin content and sensory acceptance in Turkish green tea infusions. J Food Sci Technol 52:6639–6646CrossRefGoogle Scholar
  23. Sarbon NM, Sandanamsamy S, Kamaruzaman SF, Ahmad F (2015) Chitosan extracted from mud crab (Scylla olivicea) shells: physicochemical and antioxidant properties. J Food Sci Technol 52:4266–4275CrossRefGoogle Scholar
  24. Singh SK, Townsend TG, Mazyck D, Boyer TH (2012) Equilibrium and intra-particle diffusion of stabilized landfill leachate onto micro- and meso-porous activated carbon. Water Res 46:491–499CrossRefGoogle Scholar
  25. Song X, Li C, Xu R, Wang K (2012) Molecular-ion-imprinted chitosan hydrogels for the selective adsorption of Silver(I) in aqueous solution. Ind Eng Chem Res 51:11261–11265CrossRefGoogle Scholar
  26. Suc NV, Ly HTY (2013) Lead (II) removal from aqueous solution by chitosan flake modified with citric acid via crosslinking with glutaraldehyde. J Chem Technol Biotechnol 88:1641–1649CrossRefGoogle Scholar
  27. Tang D-W et al (2013) Characterization of tea catechins-loaded nanoparticles prepared from chitosan and an edible polypeptide. Food Hydrocolloids 30:33–41CrossRefGoogle Scholar
  28. Wu L, Sun B, Li Y, Chang W (2003) Study properties of molecular imprinting polymer using a computational approach. Analyst 128:944–949CrossRefGoogle Scholar
  29. Wu L, Melton LD, Sanguansri L, Augustin MA (2014) The batch adsorption of the epigallocatechin gallate onto apple pomace. Food Chem 160:260–265CrossRefGoogle Scholar
  30. Wu L, Sanguansri L, Augustin MA (2015) Processing treatments enhance the adsorption characteristics of epigallocatechin-3-gallate onto apple pomace. J Food Eng 150:75–81CrossRefGoogle Scholar
  31. Wu L-Y et al (2016) Application of NaOH-HCl-modified apple pomace to binding epigallocatechin gallate. Food Bioprocess Technol 9:917–923CrossRefGoogle Scholar
  32. Yan H, Dai J, Yang Z, Yang H, Cheng R (2011) Enhanced and selective adsorption of copper(II) ions on surface carboxymethylated chitosan hydrogel beads. Chem Eng J 174:586–594CrossRefGoogle Scholar
  33. Yang S, Wang Y, Xu M, He M, Zhang M, Ran D, Jia X (2013) Synthesis of modified chitosan-based molecularly imprinted polymers for adsorptive protein separation. Anal Methods 5:5471–5477CrossRefGoogle Scholar
  34. Zhang H et al (2013) Selective adsorption and separation of (−)-epigallocatechin gallate (EGCG) based on silica gel surface molecularly imprinted polymers. IERI Procedia 5:339–343CrossRefGoogle Scholar
  35. Zhao F, Yu B, Yue Z, Wang T, Wen X, Liu Z, Zhao C (2007) Preparation of porous chitosan gel beads for copper(II) ion adsorption. J Hazard Mater 147:67–73CrossRefGoogle Scholar
  36. Zuo X (2014) Preparation and evaluation of novel thiourea/chitosan composite beads for Copper(II) removal in aqueous solutions. Ind Eng Chem Res 53:1249–1255CrossRefGoogle Scholar

Copyright information

© Association of Food Scientists & Technologists (India) 2017

Authors and Affiliations

  1. 1.School of Chemical Engineering and TechnologyHebei University of TechnologyTianjinChina

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