Separation of epigallocatechin-3-gallate from crude tea polyphenols by using Cellulose diacetate graft <italic><bold>BoldItalic</bold></italic>-cyclodextrin copolymer asymmetric membrane

doi:10.1007/s11705-010-1104-6

Front Chem Sci Eng

2011, Vol. 5

Issue (3) : 330-338 https://doi.org/10.1007/s11705-010-1104-6

RESEARCH ARTICLE

Separation of epigallocatechin-3-gallate from crude tea polyphenols by using Cellulose diacetate graft BoldItalic-cyclodextrin copolymer asymmetric membrane

Hong ZHU, Peiyong QIN(

)

Beijing Key Laboratory of Bioprocess, Beijing University of Chemical Technology, Beijing 100029, China

Download: PDF(380 KB) HTML
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract

This study demonstrates a new Cellulose diacetate graft β-cyclodextrin (CDA-β-CD) copolymer asymmetric membrane prepared by a phase inversion technique for the separation of (-)-epigallocatechin-3-gallate (EGCG) from other polyphenols in crude tea. The graft copolymer, CDA-β-CD, was synthesized by prepolymerization of cellulose diacetate (CDA) and 1,6-hexamethylene-diisocyanate (HDI), which was then grafted with β-cyclodextrin (β-CD). Surface and cross-section morphologies of the CDA-β-CD membranes were analyzed by using scanning electron microscopy (SEM). Fourier transform infrared spectroscopy (FT-IR) indicated that the β-CD was grafted onto the CDA by chemical bonding. The influences of the HDI/CDA mass ratio and the catalyst mass fraction on the β-CD graft yield were investigated. The optimum conditions of a HDI/CDA mass ratio of 0.35 g·g^-1 and a catalyst mass fraction of 0.18 wt-% produced a β-CD graft yield of 26.51 wt-%. The effects of the β-CD graft yield and the concentration of the polymer cast solution on the separation of EGCG were also investigated. Under optimum conditions of a β-CD graft yield of 24.21 wt-% and a polymer concentration of 13 wt-%, the purity of EGCG increased from 26.51 to 86.91 wt-%.

Keywords (-)-epigallocatechin-3-gallate (EGCG) tea polyphenols CDA-β-CD

Corresponding Author(s): QIN Peiyong,Email:qinpeiyong@tsinghua.org.cn

Issue Date: 05 September 2011

Cite this article:

Hong ZHU,Peiyong QIN. Separation of epigallocatechin-3-gallate from crude tea polyphenols by using Cellulose diacetate graft BoldItalic-cyclodextrin copolymer asymmetric membrane[J]. Front Chem Sci Eng, 2011, 5(3): 330-338.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-010-1104-6
https://academic.hep.com.cn/fcse/EN/Y2011/V5/I3/330

Fig.1 Structure of (–)-epicatechin (a), (–)-epicatechin-3-gallate (b), (–)-epigallocatechin (c), (–)-epigallocatechin-3-gallate (d)

Fig.2 Synthesis of CDA--CD

Fig.3 Effect of the HDI/CDA mass ratio on the -CD graft yield

Fig.4 Effects of the catalyst mass fraction on the -CD graft yield

Fig.5 FT-IR spectra of the CDA membrane (a) and the CDA--CD membrane (b)

Fig.6 SEM micrographs of various surfaces and cross-sections. (a) Surface SEM of the CDA membrane; (b) Surface SEM of the CDA--CD membrane; (c) Cross-section SEM of the CDA membrane; (d) Cross-section SEM of the CDA--CD membrane

Fig.7 Effect of the -CD graft yield on the adsorption capacity for EGCG

Fig.8 Effect of the -CD graft yield on the purity of EGCG

Fig.9 Effect of the concentration of the polymer cast solution on the adsorption capacity for EGCG

Fig.10 Effect of the concentration of the polymer cast solution on the purity of EGCG

Fig.11 HPLC chromatograms of crude polyphenols (a) and purified EGCG (b)

1	Nagle D G, Ferreira D, Zhou Y D. Epigallocatechin-3-gallate (EGCG): chemical and biomedical perspectives. Phytochemistry , 2006, 67(17): 1849–1855
2	Xu J, Sandstr?m C, Janson J C, Tan T. Chromatographic retention of epigallocatechin gallate on oligo-b-cyclodextrin coupled sepharose media investigated using NMR. Chromatographia , 2006, 64(1-2): 7–11
3	Xu J, Zhang G F, Tan T W, Janson J C. One-step purification of epigallocatechin gallate from crude green tea extracts by isocratic hydrogen bond adsorption chromatography on b-cyclodextrin substituted agarose gel media. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences , 2005, 824(1-2): 323–326
4	Kumamoto M, Sonda T, Takedomi K, Tabata M. Enhanced separation and elution of catechins in HPLC using mixed-solvents of water, acetonitrile and ethyl acetate as the mobile phase. Analytical Sciences , 2000, 16(2): 139–144
5	Amarowicz R, Maryniak A, Shahidi F. TLC separation of methylated (–)-epigallocatechin-3-gallate. Czech Journal of Food Sciences , 2005, 23: 36–39
6	Kim J I, Hong S B, Row K H. Effect of particle size in preparative reversed-phase high-performance liquid chromatography on the isolation of epigallocatechin gallate from Korean green tea. Journal of Chromatography. A , 2002, 949(1-2): 275–280
7	Sharma V, Gulati A, Ravindranath S D, Kumar V. A simple and convenient method for analysis of tea biochemicals by reverse phase HPLC. Journal of Food Composition and Analysis , 2005, 18(6): 583–594
8	Yanagida A, Shoji A, Shibusawa Y, Shindo H, Tagashira M, Ikeda M, Ito Y. Analytical separation of tea catechins and food-related polyphenols by high-speed counter-current chromatography. Journal of Chromatography. A , 2006, 1112(1-2): 195–201
9	Kartsova L A, Ganzha O V. Electrophoretic separation of tea flavanoids in the modes of capillary (zone) electrophoresis and micellar electrokinetic chromatography. Russian Journal of Applied Chemistry , 2006, 79(7): 1110–1114
10	Bazinet L, Labbe D, Tremblay A. Production of green tea EGC- and EGCG- enriched fractions by a two-step extraction procedure. Separation and Purification Technology , 2007, 56(1): 53–56
11	Chang C J, Chiu K L, Chen Y L, Chang C Y. Separation of catechins from green tea using carbon dioxide extraction. Food Chemistry , 2000, 68(1): 109–113
12	Wu X H. Application of membrane-separation in food technology. Food Research and Development , 2005, 26: 11–13 (in Chinese)
13	Kim H J, Tyagi R K, Fouda A E, Ionasson K. The kinetic study for asymmetric membrane formation via phase-inversion process. Journal of Applied Polymer Science , 1996, 62(4): 621–629
14	Wilbert M C, Pellegrino J, Zydney A. Bench-scale testing of surfactant-modified reverse osmosis/nanofiltration membranes. Desalination , 1998, 115(1): 15–32
15	Sivakumar M, Malaisamy R, Sajitha C J, Mohan D, Mohan V, Rangarajan R. Ultrafiltration application of cellulose acetate-polyurethane blend membranes. European Polymer Journal , 1999, 35(9): 1647–1651
16	Kozlowski C A, Sliwa W. The use of membranes with cyclodextrin units in separation processes: Recent advances. Carbohydrate Polymers , 2008, 74(1): 1–9
17	Schneiderman E, Stalcup A M. Cyclodextrins: a versatile tool in separation science. J Chromatography B. Biomedical Science Application , 2000, 745(1): 83–102
18	Tan Y, Hu A, Xia L, You T, Cao J. Synthesis and application of CDA-beta-CD in controlling release of drug. Journal of Applied Polymer Science , 2009, 113(3): 1811–1815
19	Lee J W, Hua F J, Lee D S. Thermoreversible gelation of biodegradable poly(e-caprolactone) and poly(ethylene glycol) multiblock copolymers in aqueous solutions. Journal of Controlled Release , 2001, 73(2-3): 315–327
20	Pan X, Niu G, Liu H. Microwave-assisted extraction of tea polyphenols and tea caffeine from green tea leaves. Chemical Engineering and Processing , 2003, 42(2): 129–133
21	Richter R, Muller H P U S. Patent, 5045226, 1991-09-03
22	Ishizu T, Hirata C, Yamamoto H, Harano K. Structure and intramolecular flexibility of β-cyclodextrin complex with (-)-epigallocatechin gallate in aqueous solvent. Magnetic Resonance in Chemistry , 2006, 44(8): 776–783
23	Ismail A F, Hassan A R. Effect of additive contents on the performances and structural properties of asymmetric polyethersulfone (PES) nanofiltration membranes. Separation and Purification Technology , 2007, 55(1): 98–109 doi: 10.1016/j.seppur.2006.11.002
24	Strathmann H, Kock K, Amar P, Baker R W. The formation mechanism of asymmetric membranes. Desalination , 1975, 16(2): 179–203 doi: 10.1016/S0011-9164(00)82092-5

Viewed

Full text

Abstract

Cited

Shared

Discussed