CN104356105B - A kind of preparation method of EGCG - Google Patents
A kind of preparation method of EGCG Download PDFInfo
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- CN104356105B CN104356105B CN201410562697.1A CN201410562697A CN104356105B CN 104356105 B CN104356105 B CN 104356105B CN 201410562697 A CN201410562697 A CN 201410562697A CN 104356105 B CN104356105 B CN 104356105B
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- egcg
- silica gel
- chromatographic column
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- ethanol water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
Abstract
The invention discloses the preparation method of a kind of EGCG, the preparation method of described EGCG uses the tea polyphenol extract thing containing EGCG to be raw material, through raw material pre-treatment, dress post, upper prop, eluting, concentrating, crystallize and the step such as purification obtains powder high-load EGCG, its EGCG monomer mass mark is more than 99%.The invention have the benefit that and production process effectively prevent a large amount of toxic solvents of use, production process is more environmentally-friendly, and solvent treating capacity is little, and operation is simple, ester catechin EGCG and ECG that difficulty is separated, can accomplish disposably to separate, good separating effect, separation efficiency is high, purify thing content high, crystallization time is short, and product is the most oxidizable, and product color is good, purity is high.
Description
Technical field
The present invention relates to natural product chemical technology field, it particularly relates to the preparation side of a kind of high-load EGCG
Method.
Background technology
Catechin includes nutgall catechin (GC), L-Epicatechin gallate (ECG), epigallo catechin
(EGC), epicatechin (EC) and EGCG (EGCG).Wherein, EGCG is green
The main component of tea catechin class, is also the composition that mainly comprises of Green Tea Polyphenols simultaneously, and EGCG has the most multiple biology
Activity, strong anti-oxidative activity, it is possible to protection cell and DNA are from infringement.These effects of EGCG are derived mainly from it to oxygen
The Scavenging activity of free radical, i.e. oxidation resistance.EGCG has important function in terms for the treatment of cancer and cardiovascular disease, it
Can interfere with cancer cell signals transmission, the activity of carcinogen in suppression diet, and can inverse as multi-drug resistance of the tumor
Turn agent, improve the cancerous cell sensitivity to chemotherapy, alleviate the medicine toxicity to heart simultaneously.EGCG can also stop oils and fats mistake
Oxidation, reduces low density cholesterol, extremely-low density cholesterol and the content of triglyceride in serum, suppression virus, resists radiation
And ultraviolet, prevent and treat skin aging and wrinkling.
In isolated and purified tea polyphenols, the key difficulties of EGCG is, the chemical constitution of the multiple tea polyphenols component in Folium Camelliae sinensis and
Character is the most quite similar, and wherein EGCG is the most oxidized during isolated and purified.And the production rank of batch production scale is wanted
Ask, should reach to separate efficiently, be easy to plant operation, avoid the problem of oxidation of EGCG in production process again.
The method of existing isolated and purified EGCG generally exists that method is loaded down with trivial details, time-consuming, product purity is the highest, solvent processes
Difficulty and be difficult to shortcomings such as popularizing.Existing method refers to the Chinese patent of bulletin on June 9th, 2010
200910273058.2, it discloses the batch production extracting method of a kind of high-load EGCG catechin, it uses KR-100-5
C18 is column packing, respectively with 25%, 75% ethanol water as eluant, carries out column chromatography, temporally or volume collection
Theine monomer EGCG target liquid, carries out target liquid reclaiming concentration, crystallizing to obtain catechin EGCG monomer, but this invention is deposited
At complex operation, solvent treating capacity is big and method for crystallising is simply easily caused oxidation and makes the problems such as color and luster intensification, it is impossible to ensure to obtain
Obtain quality, coloury EGCG product.Chinese patent with reference to bulletin on November 21st, 2007
200710090211.9, it is with tea polyphenols as raw material, through dissolving, column chromatography, concentrates, crystallizes and obtain EGCG monomer, but institute
EGCG content of monomer to only have amount amount at 90%, and solvent big.
In sum, although existing method can reach the extraction of the EGCG monomer of certain purity, but it is numerous to there is operation
Trivial, EGCG is oxidizable, solvent treating capacity is big and purifies the problems such as thing content is low.
Summary of the invention
It is an object of the invention to provide the preparation method of a kind of high-load EGCG, to overcome EGCG in existing correlation technique
The complex operation that exists of purification process, solvent treating capacity purification process big, EGCG is oxidizable and to purify thing content low etc.
The deficiency of problem.
It is an object of the invention to be achieved through the following technical solutions:
The preparation method of a kind of high-load EGCG, comprises the following steps:
Step 1: the tea polyphenol extract raw material containing EGCG being pre-selected is carried out dissolution process, and solvent is pure water, obtains
Tea polyphenol extract thing solution；
Step 2: silica gel is added in 1% (volume fraction) ethanol water prepared in advance in right amount, described silica gel and 1% ethanol
After aqueous solution is sufficiently mixed uniformly, add in the chromatographic column being pre-configured with；
Step 3: use wet method upper prop, adds the tea polyphenol extract thing solution obtained by step 1 to described chromatographic column, described tea
Polyphenol extract solution is adsorbed on the silica gel in described chromatographic column；
Step 4: utilize 1% ethanol water prepared in advance that the silica gel in the chromatographic column that step 3 processes is carried out eluting, and
And, when this 1% ethanol water flow to the Silica Surface in described chromatographic column, utilize and prepare 10-20% (volume integral in advance
Number) ethanol water continues the silica gel in chromatographic column described in eluting；
Step 5: when described 10-20% ethanol water flow to described chromatographic column post mouth, collects eluent, and is collecting 4-6
In the case of the eluent of described chromatographic column volume, stop described chromatographic column is carried out eluting；
Step 6: the described eluent obtaining step 5 carries out concentrating under reduced pressure process, the 3% of its volume concentration to original volume, in institute
The concentrated solution obtained adds the organic acid prepared in advance, and the mixed liquor after adding organic acid is carried out crystallization treatment, wherein,
In described mixed liquor, the concentration of organic acid is 0.1-1.0% (mass concentration)；
Step 7: be rinsed the crystallization obtained by step 6, filter, freezing and be dried, obtains powder high-load EGCG,
More than 99%, (HPLC method measures its EGCG monomer mass mark: High Performance Liquid
Chromatography, high performance liquid chromatography).
Further, in described step 1, the mode of dissolution process is ultrasonic or heating, described ultrasonic or heat time heating time is equal
For 30min, described heating-up temperature is 60 DEG C.
Further, in described step 2,1% ethanol water is 1:3 with the volume ratio of silica gel.
Further, in described step 2, the silica gel of employing is the reverse silica gel of C18, and its mesh number is 100 mesh.
Further, in described step 2, silica gel and the well-mixed wet apparent density of 1% ethanol water are 0.75kg/L.
Further, in described step 3, tea polyphenol extract thing solution is 30min-60min with the adsorption time of silica gel.
Further, in described step 4, the volume of 1% ethanol water is tea polyphenol extract thing solution in described step 3
1-2 times of volume.
Further, in described step 6, organic acid is at least one in citric acid, oxalic acid and tartaric acid.
Further, in described step 6, method for crystallising uses hot saturated solution the crystallizing process under low temperature, and crystallization temperature is 4 DEG C.
The invention have the benefit that and production process effectively prevent a large amount of toxic solvents of use, production process more ring
Protecting, solvent treating capacity is little, and operation is simple, ester catechin EGCG and ECG separated for difficulty, can accomplish once
Property separate, good separating effect, separation efficiency is high, purifies thing content high, and crystallization time is short, and product is the most oxidizable, product color
Good, purity height.
Detailed description of the invention
Technical scheme in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment is only
It is a part of embodiment of the present invention rather than whole embodiments.Based on the embodiment in the present invention, ordinary skill people
The every other embodiment that member is obtained, broadly falls into the scope of protection of the invention.
Embodiment 1:
The preparation method of a kind of high-load EGCG of 1 according to embodiments of the present invention, comprises the following steps:
Step 1: with the tea polyphenol extract thing containing EGCG 90% as raw material, the quality that feeds intake is 2 kilograms, will be containing EGCG 90%
Tea polyphenol extract raw material carry out dissolution process, solvent is pure water, obtains tea polyphenol extract thing solution, described dissolution process
Mode is ultrasonic or heating, and described ultrasonic or be 30min heat time heating time, described heating-up temperature is 60 DEG C；
Step 2: add in 1% ethanol water by reverse for C18 silica gel, described reverse silica gel is to carry out on the basis of purification on normal-phase silica gel
Chemical reaction, is substituted by OR OH, and wherein R is the silica gel of carbochain, and it is 18 that C18 reverse phase silica gel is carbon containing numerical value
Reverse phase silica gel, the mesh number of described C18 reverse phase silica gel is 100 mesh, and the addition of described C18 reverse phase silica gel regards the rule of chromatographic column
Depending on lattice, the column volume of described C18 reverse phase silica gel is 47L, and the reverse silica gel of described C18 and 1% ethanol water are the most mixed
Closing, mixed wet apparent density is 0.75kg/L, and 1% ethanol water is 1:3 with the volume ratio of the reverse silica gel of C18, will fill
1% ethanol water dividing the mixing reverse silica gel of C18 adds in the chromatographic column being pre-configured with, and pressurization makes the anti-phase silicon of C18 repeatedly
Glue is piled up more firm；
Step 3: use wet method upper prop, adds the tea polyphenol extract thing solution obtained by step 1 to described chromatographic column, described tea
Polyphenol extract solution is adsorbed on the C18 reverse phase silica gel in described chromatographic column, and its adsorption time is 30min-60min；
Step 4: utilize 1% ethanol water prepared in advance that the C18 reverse phase silica gel in the chromatographic column that step 3 processes is carried out
Eluting, the volume of described 1% ethanol water is 1 times of tea polyphenol extract thing liquor capacity, and this elution fractions is not collected,
Elution process can remove the impurity that part non-ester catechin, part chromatic number and polysaccharide isopolarity are bigger, when 1% ethanol is water-soluble
When liquid stream is to C18 reverse phase silica gel surface 5cm, 20% ethanol water prepared in advance is utilized to continue in chromatographic column described in eluting
C18 reverse phase silica gel；
Step 5: when described 20% ethanol water flow to chromatographic column mouth, starts to collect eluent, and is collecting 4 described layers
In the case of the eluent of analysis post column volume, stopping described chromatographic column is carried out eluting, eluent collecting amount is 188L；
Step 6: the eluent of 4 column volumes will collected in step 5, is reduced pressure by concentrating under reduced pressure pot or single effect evaporator
Concentrate, the 3% of its volume concentration to original volume, obtain 6 liters of concentrated solutions, add in obtained concentrated solution and to prepare in advance
Organic acid, described organic acid is citric acid, and the mixed liquor after adding citric acid is carried out crystallization treatment, wherein, described mixing
In liquid, citric acid mass concentration is 0.1%, uses hot saturated solution the crystallizing process under low temperature to crystallize, and its crystallization temperature is 4 DEG C, stands
72h；
Step 7: the crystal appropriate amount of purified water obtained in step 6 rinsed, centrifuge filters, then cold by freezer dryer
Lyophilizing is dry, obtains the EGCG of powder, and its quality is 1.4 kilograms, and its EGCG content of monomer is more than 99%.
Embodiment 2:
The preparation method of a kind of high-load EGCG of 2 according to embodiments of the present invention, comprises the following steps:
Step 1: with the tea polyphenol extract thing containing EGCG 60% as raw material, i.e. low content tea polyphenol extract thing, select low content tea
Polyphenol extract is as raw material, it is to avoid the loaded down with trivial details technique directly extracted from natural plants, farthest controls cost,
More embody the superiority of this technique simultaneously.The quality that feeds intake is 2 kilograms, is carried out at dissolving by low content tea polyphenol extract thing
Reason, solvent is pure water, obtains tea polyphenol extract thing solution, described dissolution process mode be ultrasonic or heating, described ultrasonic or
Being 30min heat time heating time, described heating-up temperature is 60 DEG C；
Step 2: add in 1% ethanol water by reverse for C18 silica gel, described reverse silica gel is to carry out on the basis of purification on normal-phase silica gel
Chemical reaction, is substituted by OR OH, and wherein R is the silica gel of carbochain, and it is 18 that C18 reverse phase silica gel is carbon containing numerical value
Reverse phase silica gel, the mesh number of described C18 reverse phase silica gel is 100 mesh, and the addition of described C18 reverse phase silica gel regards the rule of chromatographic column
Depending on lattice, the column volume of described C18 reverse phase silica gel is 47L, and the reverse silica gel of described C18 and 1% ethanol water are the most mixed
Closing, mixed wet apparent density is 0.75kg/L, and 1% ethanol water is 1:3 with the volume ratio of the reverse silica gel of C18, will fill
1% ethanol water dividing the mixing reverse silica gel of C18 adds in the chromatographic column being pre-configured with, and pressurization makes the anti-phase silicon of C18 repeatedly
Glue is piled up more firm；
Step 3: use wet method upper prop, adds the tea polyphenol extract thing solution obtained by step 1 to described chromatographic column, described tea
Polyphenol extract solution is adsorbed on the C18 reverse phase silica gel in described chromatographic column, and its adsorption time is 30min-60min；
Step 4: utilize 1% ethanol water prepared in advance that the C18 reverse phase silica gel in the chromatographic column that step 3 processes is carried out
Eluting, the volume of described 1% ethanol water is 1 times of tea polyphenol extract thing liquor capacity, and this elution fractions is not collected,
Elution process can remove the impurity that part non-ester catechin, part chromatic number and polysaccharide isopolarity are bigger, when 1% ethanol is water-soluble
When liquid stream is to C18 reverse phase silica gel surface 5cm, 15% ethanol water prepared in advance is utilized to continue in chromatographic column described in eluting
C18 reverse phase silica gel；
Step 5: when described 15% ethanol water flow to chromatographic column mouth, starts to collect eluent, and is collecting 5 described layers
In the case of the eluent of analysis post column volume, stopping described chromatographic column is carried out eluting, eluent collecting amount is 235 liters；
Step 6: the eluent of 5 column volumes will collected in step 5, is reduced pressure by concentrating under reduced pressure pot or single effect evaporator
Concentrate, the 3% of its volume concentration to original volume, obtain 7 liters of concentrated solutions, add in obtained concentrated solution and to prepare in advance
Organic acid, described organic acid is citric acid, and the mixed liquor after adding citric acid is carried out crystallization treatment, wherein said mixed liquor
Middle citric acid mass concentration is 1%, uses hot saturated solution the crystallizing process under low temperature to crystallize, and crystallization temperature is 4 DEG C, stands 168h；
Step 7: the crystal appropriate amount of purified water obtained in step 6 rinsed, centrifuge filters, then cold by freezer dryer
Lyophilizing is dry, obtains the EGCG of powder, and its quality is 0.5 kilogram, and its EGCG content of monomer is more than 99%.
In specific implementation process, the preparation method of above-mentioned high-load EGCG is not limited only to laboratory implementation, it is also possible in work
Factory's metaplasia is implemented in producing, and the volume of involved quality of material and required solvent need to be proportionally enlarged by implementation process, by
Processing quantity of solvent in this preparation method little, purification efficiency is high, therefore, in factorial praluction, and the factor such as remover apparatus fault,
The daily output of described high-load EGCG up to tonne.
In sum, by means of the technique scheme of the present invention, production process effectively prevent use a large amount of poisonous molten
Agent, production process is more environmentally-friendly, and solvent treating capacity is little, and operation is simple, the ester catechin EGCG separated for difficulty
And ECG, can accomplish disposably to separate, good separating effect, separation efficiency is high, purifies thing content high, and crystallization time is short, produces
Product are the most oxidizable, and product color is good, purity is high.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all spirit in the present invention
Within principle, any modification, equivalent substitution and improvement etc. made, should be included within the scope of the present invention.
Claims (7)
1. the preparation method of an EGCG, it is characterised in that including:
Step 1: the tea polyphenol extract raw material containing EGCG being pre-selected is carried out dissolution process, and solvent is pure water, obtains tea polyphenol extract thing solution；
Step 2: added by silica gel in appropriate 1% ethanol water prepared in advance, after being sufficiently mixed uniformly, adds the chromatographic column being pre-configured with；Wherein, 1% ethanol water is 1:3 with the volume ratio of silica gel；Silica gel and the well-mixed wet apparent density of 1% ethanol water are 0.75kg/L；
Step 3: being added to described chromatographic column by the tea polyphenol extract thing solution obtained by step 1, described tea polyphenol extract thing solution is adsorbed on the silica gel in described chromatographic column；
Step 4: utilize 1% ethanol water prepared in advance, silica gel in the chromatographic column that step 3 processes is carried out eluting, and, when this 1% ethanol water flow to the Silica Surface 5cm in described chromatographic column, the 10-20% ethanol water prepared in advance is utilized to continue the silica gel in chromatographic column described in eluting；
Step 5: when described 10-20% ethanol water flow to described chromatographic column post mouth, collects eluent, and in the case of collecting 4-6 the long-pending eluent of described chromatographic column cylinder, stops described chromatographic column is carried out eluting；
Step 6: the described eluent obtaining step 5 carries out concentrating under reduced pressure process, the organic acid prepared in advance is added in obtained concentrated solution, and the mixed liquor after adding organic acid is carried out crystallization treatment, wherein, in described mixed liquor, organic acid mass concentration is 0.1-1.0%；
Step 7: be rinsed the crystallization obtained by step 6, filter, freezing and be dried, prepares powder EGCG, and its EGCG monomer mass percent is more than 99%.
The preparation method of EGCG the most according to claim 1, it is characterised in that in described step 1, the mode of dissolution process is ultrasonic or heating, and described ultrasonic or be heat time heating time 30 minutes, described heating-up temperature is 60 DEG C.
The preparation method of EGCG the most according to claim 1, it is characterised in that in described step 2, the silica gel of employing is the reverse silica gel of C18, and its mesh number is 100 mesh.
The preparation method of EGCG the most according to claim 1, it is characterised in that in described step 3, tea polyphenol extract thing solution is 30-60 minute with the adsorption time of silica gel.
The preparation method of EGCG the most according to claim 1, it is characterised in that in described step 4, the volume of 1% ethanol water is in described step 3 1-2 times of tea polyphenol extract thing liquor capacity.
The preparation method of EGCG the most according to claim 1, it is characterised in that at least one during organic acid is citric acid, oxalic acid and tartaric acid in described step 6.
The preparation method of EGCG the most according to claim 6, it is characterised in that in described step 6, method for crystallising uses hot saturated solution the crystallizing process under low temperature, and crystallization temperature is 4 DEG C.
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| CN106168608A (en) * | 2016-08-25 | 2016-11-30 | 江苏天晟药业股份有限公司 | The detection method of EGCG content in a kind of tea polyphenols |
| CN106749150A (en) * | 2016-11-27 | 2017-05-31 | 湖北中鑫生物科技有限公司 | A kind of preparation method of high content EGCG |
| CN113546014B (en) * | 2021-07-26 | 2023-06-02 | 广州市百益康生物科技发展有限公司 | Extraction method of dissolved tea polyphenol and Bos safflower fat and skin-moistening oil thereof |
| CN114230542A (en) * | 2021-12-24 | 2022-03-25 | 浙江天草生物科技股份有限公司 | Method for extracting EGCG from fresh tea leaves |
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| CN1197857C (en) * | 2003-06-25 | 2005-04-20 | 张守政 | Method for extracting tea polyhenols and tea pigment |
| CN101074224A (en) * | 2007-04-13 | 2007-11-21 | 桂林莱茵生物科技股份有限公司 | Production of high-content EGCG |
| CN101643466B (en) * | 2009-06-02 | 2011-12-14 | 江苏天晟药业有限公司 | Epigallo-catechin gallate (EGCG) with high purity and preparation method thereof |
| CN101723927B (en) * | 2009-12-02 | 2015-05-13 | 宜昌绿源生物技术有限公司 | Method for batch production, separation and purification of catechin monomers EGCG |
| CN102311419A (en) * | 2011-09-09 | 2012-01-11 | 四川天予植物药业有限公司 | Refining and purification method of high content EGCG |
| CN102603699A (en) * | 2012-02-29 | 2012-07-25 | 桂林三宝药业有限公司 | Method for extracting epigallocatechin gallate from oil-tea-cake |
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