CN102276570A - Method for purifying epigallo catechin gallate (EGCG) - Google Patents
Method for purifying epigallo catechin gallate (EGCG) Download PDFInfo
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Abstract
The invention discloses a method for separating and purifying epigallo catechin gallate (EGCG) by using a simulated moving bed (SMB) chromatography. The method is characterized in that: a tea leaf extract, which is tea polyphenol, is adopted as a raw material; EGCG is separated and purified by using an SMB chromatography system. According to the method, fundamental zones of the SMB are set as an eluting zone, a refining zone and an absorbing zone. The eluting zone is independent. Octadecylsilane chemically bonded silica ODS is adopted as a stationary phase, a mixed solution of alcohol and water is adopted as a mobile phase, and SMB separation are carried out two times upon a tea polyphenol raw material liquid, wherein one time is for removing impurities which are hard to elute, and the other time is for removing impurities which are easy to elute. The product is processed through a solvent removing process, such that the EGCG product is obtained. With the method, EGCG can be stably, continuously, and automatically purified from tea polyphenol in large scale, and with high efficiency. The recycling rate of the product is above 94%, and the purity of the product is above 96%. According to the invention, the stationary phase and the mobile phase can be repeatedly utilized, such that the cost is reduced. The invention belongs to green and environment-friendly separation engineering.
Description
Technical field
The present invention relates to the separating and purifying method of natural phant active principle, especially a kind of method of utilizing three-section simulated moving bed chromatography purification NVP-XAA 723 (EGCG).
Background technology
NVP-XAA 723 (is called for short EGCG, to call EGCG in the following text) be a kind of oxidation-resistance and the very strong active substance of removing free radical function, as the new drug of a kind of antitumor, anti-mutation, purposes such as hypotensive, it extracts with application and is subjected to domestic and international extensive concern.EGCG is that the Polyphenols mixture that tealeaves extracts is the main component of tea-polyphenol, in tea-polyphenol, also has other flavanols compounds very close with character with the EGCG chemical structure, as: l-Epicatechol (EC); L-Epicatechin gallate (ECG); Epigallocatechin (EGC); Nutgall catechin gallic acid ester (GCG); DL-catechin (DL-C), and the very easily oxidation of these flavanols compounds, poly-(contracting) closes, and makes separation and purification EGCG monomer difficulty.
At present, the major technique that obtains high purity EGCG monomer (being higher than 95%) is the preparative chromatography partition method, as: CN1319597 (separation method of catechin compounds in a kind of tea-polyphenol), CN1603319 (separation purification method of catechin monomers) and CN1465572 (epi-nutgall catechin gallic acid ester monomer purifying method) adopt the chromatography of dextrane gel SephadexLH-20 post; CN101381359 (a kind of method of extracting high-purity epigallocatechin-3-gallate from green tea) adopts the chromatography of flicker silicagel column, CN101723927A (a kind of method for batch production, separation and purification of catechin monomers EGCG) adopts the chromatography of KR100-5C18 post, though these methods can be used for the industrial production high purity EGCG, but all be that batch process is the purifying technique at intermittence, can not produce automatically continuously, and the utilization ratio of sorbent material is low, the eluent consumption is big, the treatment capacity of raw material is less, consuming time, production efficiency is low.
Simulated moving bed chromatography is the powerful separation means with advantage of of purification compound.Simulated moving bed chromatography has been introduced special operating mechanism on the basis of preparative chromatography, make chromatographic separation process from intermittently becoming continuously, can carry out high efficiency automatization and separate with mass-producing.Still do not have at present and adopt the report of simulated moving bed chromatography technical point from purification EGCG.
Summary of the invention
The invention provides the method for a kind of simulation moving-bed (being called for short SMB, to call SMB in the following text) chromatographic purification NVP-XAA 723 (being called for short EGCG, to call EGCG in the following text), EGCG continuously, automatically, efficiently can purify.
The method of purification EGCG is characterized in that with the tea leaf extract tea-polyphenol be raw material, adopts SMB chromatographic purification EGCG, and the technical scheme of this method is as follows:
(1) SMB equipment
SMB equipment consists of chromatographic column, elutriant transferpump, feeding liquid transferpump, internally piloted valve, micro-chip, automatic control system, many logical, pipelines, joint, container for storing liquid, computer;
The chromatographic column specification is column length 10~50cm, and column length is 8~20 with the diameter ratio;
Stationary phase uses octadecylsilane chemically bonded silica ODS, 10~60 μ m;
Internally piloted valve is made up of magnetic valve and non-return valve.
(2) SMB working conditions
SMB operational mode: the chromatographic column number sum N of SMB system is set, 3≤N≤8, the base region band that SMB is set is an elution band, refining band and adsorption zone, each band is in series by 1~4 identical chromatographic column, and a is an elution band chromatographic column number, b is refining band chromatographic column number, c is an adsorption zone chromatographic column number, a+b+c=N, and operational mode is expressed as a-b-c;
Moving phase is formed: the moving phase D of refining band and adsorption zone is alcohol and water blended homogeneous phase solution, the volumn concentration C of alcohol
DBe 10~40%; The moving phase P of elution band is alcohol and water blended homogeneous phase solution, the volumn concentration C of alcohol
PBe C
D~100%;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 1~20cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 1~15cm/min, sample introduction liquid F flow velocity U
FBe 0.1~6cm/min, raffinate R flow velocity U
R=U
D+ U
FU
D≤ U
p≤ 3U
DU
F<2U
D
Simulation moving-bed service temperature: room temperature.
(3) separating step
Use as (1) as described in SMB equipment as (2) described condition under, carry out twice SMB separation: once be to remove difficult wash-out impurity from extraction liquid E, switching time t
S: 5~30min; Another time removed easy wash-out impurity from raffinate R, switching time t
S: 3~25min;
Tea-polyphenol is the dissolving of 0~100% the aqueous solution with pure content, and configuration concentration is the homogeneous phase stock liquid of 10~100mg/mL, as the isolating sample introduction liquid of SMB first time F; The first time, SMB separated raffinate R or the concentrated back of process or direct as the isolating sample introduction liquid of SMB second time F that obtains;
The EGCG solution of removing impurity after removing solvent treatment, is obtained the EGCG product.
(4) detection method
Adopt Tianjin, island LC-10AT chromatogram pump, SPD-10A UV-detector, Agilent Extend chromatographic column, 4.6 * 150mm, the ODS filler, particle diameter 5 μ m, moving phase is acetonitrile and water, volume ratio is 15: 85, Glacial acetic acid volumn concentration 0.1%, flow velocity 1.0mL/min detects wavelength 278nm.Demarcate the content of EGCG in the product by the EGCG standard substance.
The method of described SMB chromatographic purification EGCG, the alcohol in the moving phase are methyl alcohol, ethanol.
The method of described SMB chromatographic purification EGCG, stationary phase ODS, 20~30 μ m; The moving phase D of refining band and adsorption zone adopts methanol aqueous solution, wherein methyl alcohol volumn concentration C
DBe 25~35%.
The method of described SMB chromatographic purification EGCG, stationary phase ODS, 20~30 μ m; The moving phase D of refining band and adsorption zone adopts aqueous ethanolic solution, wherein ethanol volumn concentration C
DBe 10~20%.
The method of described SMB chromatographic purification EGCG is separated the process that the EGCG solution obtain removes solvent by SMB and is: perhaps lyophilize or recrystallization or vacuum-drying or pressure reducing film distillation.
Method with simulated moving bed chromatography separation purification EGCG provided by the invention is compared with existing preparative chromatography isolation technique; its significant advantage is can mass-producing, EGCG steadily and surely, continuously, automatically and efficiently purifies from tea-polyphenol; product recovery rate surpasses 94%; purity surpasses 96%; stationary phase and mobile being on good terms are recycled; reduce cost, belong to the environmental protection separation engineering.
Description of drawings
Fig. 1 is twice simulation moving-bed sepn process synoptic diagram;
Fig. 2 is the HPLC spectrogram of tea polyphenol raw materials liquid;
Fig. 3 is the SMB separating resulting first time, the HPLC spectrogram of difficult wash-out impurity;
Fig. 4 is the SMB separating resulting first time, removes the HPLC spectrogram of the EGCG of difficult wash-out impurity;
Fig. 5 is the SMB separating resulting second time, easily the HPLC spectrogram of wash-out impurity;
Fig. 6 is the SMB separating resulting second time, removes the HPLC spectrogram of the EGCG of impurity.
Embodiment
(1) SMB equipment
8 root chromatogram columns, moving phase D transferpump flow 0-10mL/min, pressure 0-10Mpa; Stock liquid F pumping capacity 0-30mL/h, pressure 0-8Mpa; Moving phase P transferpump flow 0-10mL/min, pressure 0-10Mpa, 48 internally piloted valves, a cover single chip computer automatic control system, 5 container for storing liquids (each needs a container for storing liquid moving phase D, stock liquid F, moving phase P, extraction liquid E, raffinate R), many logical, pipelines, joint, computer; Chromatographic column is specification 10cm * 1cm; Stationary phase uses octadecylsilane chemically bonded silica ODS, 20~30 μ m.
(2) SMB working conditions
The SMB working conditions is as follows for the first time:
The SMB operational mode: the chromatographic column number sum N=4 of SMB system is set, SMB elution band 1 root chromatogram column is set, make with extra care and be with 1 root chromatogram column, adsorption zone 2 root chromatogram columns, operational mode is 1-1-2;
Moving phase is formed: the moving phase D of refining band and adsorption zone is the mixing solutions of methyl alcohol and water, the volumn concentration C of methyl alcohol
DBe 30%; The moving phase P of elution band is the mixing solutions of methyl alcohol and water, the volumn concentration C of alcohol
PBe 80%;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 3.2cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 1.9cm/min, sample introduction liquid F flow velocity U
FBe 0.13cm/min, raffinate R flow velocity U
R=U
D+ U
F
Be switching time: 15min.
Simulation moving-bed service temperature: 15-20 ℃.
The SMB working conditions is as follows for the second time:
The SMB operational mode: the chromatographic column number sum N=4 of SMB system is set, SMB elution band 1 root chromatogram column is set, make with extra care and be with 1 root chromatogram column, adsorption zone 2 root chromatogram columns, operational mode is 1-1-2;
Moving phase is formed: the moving phase D of refining band and adsorption zone is the mixing solutions of methyl alcohol and water, the volumn concentration C of methyl alcohol
DBe 30%; The moving phase P of elution band is the mixing solutions of methyl alcohol and water, the volumn concentration C of alcohol
PBe 60%;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 3.8cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 1.9cm/min, sample introduction liquid F flow velocity U
FBe 0.13cm/min, raffinate R flow velocity U
R=U
D+ U
F
Be switching time: 10min.
Simulation moving-bed service temperature: 15-20 ℃.
(3) separating step
Use as (1) as described in SMB equipment as (2) described condition under, carry out twice SMB separation, as shown in Figure 1.SMB separation for the first time is to remove difficult wash-out impurity from extraction liquid E, get 5 gram tea polyphenol raw materials (EGCG purity 55.5%), with the methyl alcohol volumn concentration is the dissolving of 30% the aqueous solution, 0.45 μ m membrane filtration, configuration concentration is the solution of 5g/100mL, as the isolating sample introduction liquid of SMB first time F, EGCG is 22.3mg/mL, its HPLC spectrogram as shown in Figure 2, with moving phase P difficult wash-out impurity is removed in extraction liquid E, its HPLC spectrogram is obtained to contain the raffinate R of easy wash-out impurity and EGCG as shown in Figure 3 by moving phase D, its HPLC spectrogram as shown in Figure 4, the purity of EGCG is 92.19%, and yield 99.7% concentrates this raffinate rotary evaporation, EGCG is 18mg/mL, as the isolating sample introduction liquid of SMB second time F.SMB separation for the second time is to remove easy wash-out impurity, with moving phase D easy wash-out impurity is removed in raffinate R, and its HPLC spectrogram as shown in Figure 5, obtain the extraction liquid E of EGCG by moving phase P, its HPLC spectrogram as shown in Figure 6, the purity of EGCG is 97.8%, yield 99.8%.The extraction liquid of EGCG is behind rotary evaporation, and lyophilize obtains the EGCG product.
(4) detection method
Adopt Tianjin, island LC-10AT chromatogram pump, SPD-10A UV-detector, Agilent Extend chromatographic column, 4.6 * 150mm, the ODS filler, particle diameter 5 μ m, moving phase is acetonitrile and water, volume ratio is 15: 85, Glacial acetic acid volumn concentration 0.1%, flow velocity 1.0mL/min detects wavelength 278nm.Demarcate the content of EGCG in the product by the EGCG standard substance.
(1) SMB equipment: with embodiment 1.
(2) SMB working conditions
The SMB working conditions is as follows for the first time:
The SMB operational mode: the chromatographic column number sum N=5 of SMB system is set, SMB elution band 1 root chromatogram column is set, make with extra care and be with 2 root chromatogram columns, adsorption zone 2 root chromatogram columns, operational mode is 1-2-2;
Moving phase is formed: the moving phase D of refining band and adsorption zone is the mixing solutions of ethanol and water, alcoholic acid volumn concentration C
DBe 15%; The moving phase P of elution band is an ethanol;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 3.8cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 2.9cm/min, sample introduction liquid F flow velocity U
FBe 0.25cm/min, raffinate R flow velocity U
R=U
D+ U
F
Be switching time: 14min.
Simulation moving-bed service temperature: 10-15 ℃.
The SMB working conditions is as follows for the second time:
The SMB operational mode: the chromatographic column number sum N=5 of SMB system is set, SMB elution band 1 root chromatogram column is set, make with extra care and be with 2 root chromatogram columns, adsorption zone 2 root chromatogram columns, operational mode is 1-2-2;
Moving phase is formed: the moving phase D of refining band and adsorption zone is the mixing solutions of ethanol and water, alcoholic acid volumn concentration C
DBe 15%; The moving phase P of elution band is an ethanol;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 3.8cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 1.3cm/min, sample introduction liquid F flow velocity U
FBe 1.9cm/min, raffinate R flow velocity U
R=U
D+ U
F
Be switching time: 4min.
Simulation moving-bed service temperature: 10-15 ℃.
(3) separating step
Use as (1) as described in SMB equipment as (2) described condition under, carry out twice SMB separation.SMB separation for the first time is to remove difficult wash-out impurity from extraction liquid E, get 5 gram tea polyphenol raw materials (EGCG purity 65.8%), with the ethanol volumn concentration is the dissolving of 15% the aqueous solution, 0.45 μ m membrane filtration, configuration concentration is the solution of 5g/100mL, SMB separates sample introduction liquid F as the first time, EGCG is 28.9mg/mL, with moving phase P difficult wash-out impurity is removed in extraction liquid E, obtained to contain the raffinate R of easy wash-out impurity and EGCG by moving phase D, the purity of EGCG is 92.43%, yield 99.2%, this raffinate rotary evaporation is concentrated, and EGCG is 8.3mg/mL, as the isolating sample introduction liquid of SMB second time F.SMB separation for the second time is to remove easy wash-out impurity, with moving phase D easy wash-out impurity is removed in raffinate R, and by the extraction liquid E of moving phase P acquisition EGCG, the purity of EGCG is 96.5%, yield 99.4%.The extraction liquid of EGCG is behind rotary evaporation, and lyophilize obtains the EGCG product.
(4) detection method is with embodiment 1
(1) SMB equipment: with embodiment 1.
(2) SMB working conditions
The SMB working conditions is as follows for the first time:
The SMB operational mode: the chromatographic column number sum N=6 of SMB system is set, SMB elution band 1 root chromatogram column is set, make with extra care and be with 3 root chromatogram columns, adsorption zone 2 root chromatogram columns, operational mode is 1-3-2;
Moving phase is formed: the moving phase D of refining band and adsorption zone is the mixing solutions of ethanol and water, alcoholic acid volumn concentration C
DBe 15%; The moving phase P of elution band is an ethanol;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 5.1cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 2.9cm/min, sample introduction liquid F flow velocity U
FBe 0.25cm/min, raffinate R flow velocity U
R=U
D+ U
F
Be switching time: 6min.
Simulation moving-bed service temperature: 10-15 ℃.
The SMB working conditions is as follows for the second time:
The SMB operational mode: the chromatographic column number sum N=7 of SMB system is set, SMB elution band 1 root chromatogram column is set, make with extra care and be with 3 root chromatogram columns, adsorption zone 3 root chromatogram columns, operational mode is 1-3-3;
Moving phase is formed: the moving phase D of refining band and adsorption zone is the mixing solutions of ethanol and water, alcoholic acid volumn concentration C
DBe 15%; The moving phase P of elution band is an ethanol;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 5.1cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 2.0cm/min, sample introduction liquid F flow velocity U
FBe 1.1cm/min, raffinate R flow velocity U
R=U
D+ U
F
Be switching time: 5min.
Simulation moving-bed service temperature: 10-15 ℃.
(3) separating step
Use as (1) as described in SMB equipment as (2) described condition under, carry out twice SMB separation.SMB separation for the first time is to remove difficult wash-out impurity from extraction liquid E, get 5 gram tea polyphenol raw materials (EGCG purity 65.8%), with the ethanol volumn concentration is the dissolving of 15% the aqueous solution, 0.45 μ m membrane filtration, configuration concentration is the solution of 5g/100mL, SMB separates sample introduction liquid F as the first time, EGCG is 28.9mg/mL, with moving phase P difficult wash-out impurity is removed in extraction liquid E, obtained to contain the raffinate R of easy wash-out impurity and EGCG by moving phase D, the purity of EGCG is 94.4%, yield 97.5%, this raffinate rotary evaporation is concentrated, and EGCG is 11.3mg/mL, as the isolating sample introduction liquid of SMB second time F.SMB separation for the second time is to remove easy wash-out impurity, with moving phase D easy wash-out impurity is removed in raffinate R, and by the extraction liquid E of moving phase P acquisition EGCG, the purity of EGCG is 98.9%, yield 97.4%.The extraction liquid of EGCG is behind rotary evaporation, and lyophilize obtains the EGCG product.
(4) detection method is with embodiment 1.
Claims (5)
1. a purification NVP-XAA 723 (is called for short EGCG, to call EGCG in the following text) method, it is characterized in that with the tea leaf extract tea-polyphenol be raw material, adopt and simulation moving-bedly (be called for short SMB, to call SMB in the following text) chromatographic purification EGCG, the technical scheme of this method is as follows:
(1) SMB equipment
SMB equipment consists of chromatographic column, elutriant transferpump, feeding liquid transferpump, internally piloted valve, micro-chip, automatic control system, many logical, pipelines, joint, container for storing liquid, computer;
The chromatographic column specification is column length 10~50cm, and column length is 8~20 with the diameter ratio;
Stationary phase uses octadecylsilane chemically bonded silica ODS, 10~60 μ m;
Internally piloted valve is made up of magnetic valve and non-return valve;
(2) SMB working conditions
SMB operational mode: the chromatographic column number sum N of SMB system is set, 3≤N≤8, the base region band that SMB is set is an elution band, refining band and adsorption zone, each band is in series by 1~4 identical chromatographic column, and a is an elution band chromatographic column number, b is refining band chromatographic column number, c is an adsorption zone chromatographic column number, a+b+c=N, and operational mode is expressed as a-b-c;
Moving phase is formed: the moving phase D of refining band and adsorption zone is alcohol and water blended homogeneous phase solution, the volumn concentration C of alcohol
DBe 10~40%; The moving phase P of elution band is alcohol and water blended homogeneous phase solution, the volumn concentration C of alcohol
PBe C
D~100%;
Flow rate of mobile phase: in elution band, elutriant P flow velocity U
pBe 1~20cm/min, extraction liquid E flow velocity U
E=U
pIn refining band and adsorption zone, elutriant D flow velocity U
DBe 1~15cm/min, sample introduction liquid F flow velocity U
FBe 0.1~6cm/min, raffinate R flow velocity U
R=U
D+ U
FU
D≤ U
p≤ 3U
DU
F<2U
D
Simulation moving-bed service temperature: room temperature;
(3) separating step
Use as (1) as described in SMB equipment as (2) described condition under, carry out twice SMB separation: once be to remove difficult wash-out impurity from extraction liquid E, switching time t
S: 5~30min; Another time removed easy wash-out impurity from raffinate R, switching time t
S: 3~25min;
Tea-polyphenol is the dissolving of 0~100% the aqueous solution with pure volumn concentration, and configuration concentration is the homogeneous phase stock liquid of 10~100mg/mL, as the isolating sample introduction liquid of SMB first time F; The first time, SMB separated raffinate R or the concentrated back of process or direct as the isolating sample introduction liquid of SMB second time F that obtains;
The EGCG solution of removing impurity after removing solvent treatment, is obtained the EGCG product;
(4) detection method
Adopt Tianjin, island LC-10AT chromatogram pump, the SPD-10A UV-detector, Agilent Extend chromatographic column, 4.6 * 150mm, the ODS filler, particle diameter 5 μ m, moving phase is acetonitrile and water, volume ratio is 15: 85, Glacial acetic acid volumn concentration 0.1%, flow velocity 1.0mL/min detects wavelength 278nm, is demarcated the content of EGCG in the product by the EGCG standard substance.
2. the method for SMB chromatographic purification EGCG according to claim 1 is characterized in that: the alcohol in the moving phase is methyl alcohol, ethanol.
3. according to claim 1 and the method that requires 2 described SMB chromatographic purification EGCG, it is characterized in that: stationary phase ODS, 20~30 μ m; The moving phase D of refining band and adsorption zone adopts methanol aqueous solution, wherein methyl alcohol volumn concentration C
DBe 25~35%.
4. according to claim 1 and the method that requires 2 described SMB chromatographic purification EGCG, it is characterized in that: stationary phase ODS, 20~30 μ m; The moving phase D of refining band and adsorption zone adopts aqueous ethanolic solution, wherein ethanol volumn concentration C
DBe 10~20%.
5. the method for SMB chromatographic purification EGCG according to claim 1 is characterized in that: separating the process that the EGCG solution obtain removes solvent by SMB is: perhaps lyophilize or recrystallization or vacuum-drying or pressure reducing film distillation.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102643260A (en) * | 2012-04-25 | 2012-08-22 | 中国农业科学院茶叶研究所 | Method for separating epigallocatechin gallate by continuous column chromatography |
CN106986851A (en) * | 2017-05-04 | 2017-07-28 | 广西轻工业科学技术研究院 | A kind of preparation method of high purity EGCG |
CN111315391A (en) * | 2017-10-31 | 2020-06-19 | 株式会社爱茉莉太平洋 | Composition for improving circulatory system diseases comprising tea extract having different component contents |
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CN1286252A (en) * | 1999-08-16 | 2001-03-07 | 弗·哈夫曼-拉罗切有限公司 | Process for preparing epigallocatechin gallate |
CN1546485A (en) * | 2003-12-12 | 2004-11-17 | 贵州家诚药业有限责任公司 | Method for separating tea polyphenol mixture |
CN101732890A (en) * | 2009-12-08 | 2010-06-16 | 辽宁科技大学 | Three-section simulated moving bed chromatography device |
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2011
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CN1286252A (en) * | 1999-08-16 | 2001-03-07 | 弗·哈夫曼-拉罗切有限公司 | Process for preparing epigallocatechin gallate |
CN1546485A (en) * | 2003-12-12 | 2004-11-17 | 贵州家诚药业有限责任公司 | Method for separating tea polyphenol mixture |
CN101732890A (en) * | 2009-12-08 | 2010-06-16 | 辽宁科技大学 | Three-section simulated moving bed chromatography device |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102643260A (en) * | 2012-04-25 | 2012-08-22 | 中国农业科学院茶叶研究所 | Method for separating epigallocatechin gallate by continuous column chromatography |
CN106986851A (en) * | 2017-05-04 | 2017-07-28 | 广西轻工业科学技术研究院 | A kind of preparation method of high purity EGCG |
CN111315391A (en) * | 2017-10-31 | 2020-06-19 | 株式会社爱茉莉太平洋 | Composition for improving circulatory system diseases comprising tea extract having different component contents |
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