CN104356105A - Preparation method for high-content EGCG - Google Patents
Preparation method for high-content EGCG Download PDFInfo
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- CN104356105A CN104356105A CN201410562697.1A CN201410562697A CN104356105A CN 104356105 A CN104356105 A CN 104356105A CN 201410562697 A CN201410562697 A CN 201410562697A CN 104356105 A CN104356105 A CN 104356105A
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- C07—ORGANIC CHEMISTRY
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- 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
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- 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
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Abstract
The invention discloses a preparation method for high-content EGCG (Epigallocatechin Gallate). In the preparation method, a tea polyphenol extract of the EGCG is taken as a raw material, the powdery high-content EGCG is prepared by the step of performing preprocessing, column packing, column feeding, eluting, concentrating, crystallizing, purifying and the like on raw materials, and the mass fraction of an EGCG monomer is more than 99%. The preparation method has the benefits that a large quantity of toxic solvents are avoided in the production process, the production process is more environmentally-friendly, the amount of the required solvent dealt is small, the operation is simple and feasible, the ester catechins EGCG which is hard to separate is separated at one time, the separation effect is good, the separation efficiency is high, the content of the purified matter is high, the crystallization time is short, and the product is difficult to be oxidized, and is good in color and luster as well as high in purity.
Description
Technical field
The present invention relates to natural product chemical technology field, specifically, relate to the preparation method of a kind of high-content EGCG.
Background technology
Catechin comprises l-Epigallocatechol (GC), L-Epicatechin gallate (ECG), epigallocatechin (EGC), l-Epicatechol (EC) and EGCG (EGCG).Wherein, EGCG is the main component of green tea catechins class, and be also simultaneously the main moiety of Green Tea Polyphenols, EGCG has multiple biological activity widely, strong anti-oxidative activity, can Cell protection and DNA from infringement.These effects of EGCG are mainly derived from its Scavenging activity to oxyradical, i.e. resistance of oxidation.EGCG has vital role in Therapeutic cancer and cardiovascular disorder, it can interfere with cancer cells signal transmission, suppresses the activity of the carcinogenic substance in diet, and can be used as the reversal agent of multi-drug resistance of the tumor, improve cancer cells to the susceptibility of chemotherapy, alleviate the toxicity of medicine to heart simultaneously.EGCG can also stop oil peroxidation, reduces the content of low density cholesterol, extremely-low density cholesterol and triglyceride level in serum, suppresses virus, resists radiation and ultraviolet, control skin aging and wrinkling.
In separation and purification tea-polyphenol, the key difficulties of EGCG is, chemical structure and the character of the multiple tea-polyphenol component in tealeaves are all quite similar, and wherein EGCG is very easily oxidized in separation and purification process.And the production levels necessitate of batch production scale, efficient separation should be reached, be convenient to factory's operation, avoid the problem of oxidation of EGCG in production process again.
The shortcomings such as the method ubiquity method of existing separation and purification EGCG is loaded down with trivial details, time-consuming, product purity is not high, solvent treatment is difficult and not easily popularize.Existing method can with reference to the Chinese patent 200910273058.2 of bulletin on June 9th, 2010, it discloses a kind of batch production extracting method of high-content EGCG catechin, it adopts KR-100-5 C18 to be column packing, respectively with 25%, 75% aqueous ethanolic solution is eluent, carry out column chromatography, temporally or volume collection catechin monomers EGCG target liquid, carry out recovery to target liquid to concentrate, crystallization obtains catechin EGCG monomer, but there is complex operation in this invention, large and the crystallization method of solvent treatment amount simply easily causes oxidation to make the problems such as color and luster intensification, can not ensure to obtain quality, coloury EGCG product.Simultaneously with reference to the Chinese patent 200710090211.9 of bulletin on November 21st, 2007, it take tea-polyphenol as raw material, through dissolvings, column chromatography, concentrate, crystallization obtains EGCG monomer, but gained EGCG monomer content only has 90%, and solvent place amount amount is large.
In sum, although existing method can reach the extraction of the EGCG monomer of certain purity, the problem such as have that complex operation, EGCG are oxidizable, solvent treatment amount large and purification thing content is low.
Summary of the invention
The object of this invention is to provide the preparation method of a kind of high-content EGCG, the deficiency of the problems such as the oxidizable and purification thing content of the complex operation existed with the purification process overcoming EGCG in existing correlation technique, solvent treatment amount purification process that is large, EGCG is low.
The object of the invention is to be achieved through the following technical solutions:
A preparation method of high-content EGCG, comprises the following steps:
Step 1: carry out dissolution process to the tea polyphenol extract raw material containing EGCG selected in advance, solvent is pure water, obtains tea polyphenol extract thing solution;
Step 2: silica gel is added in 1% (volume fraction) aqueous ethanolic solution prepared in advance in right amount, after described silica gel fully mixes with 1% aqueous ethanolic solution, add in pre-configured chromatography column;
Step 3: adopt wet method upper prop, tea polyphenol extract thing solution step 1 obtained is added in described chromatography column, on the silica gel of described tea polyphenol extract thing solution absorbs in described chromatography column;
Step 4: utilize 1% aqueous ethanolic solution prepared in advance to carry out wash-out to the silica gel in the chromatography column processed through step 3, and, when this 1% aqueous ethanolic solution flow to the Silica Surface in described chromatography column, utilize the silica gel prepared in advance in chromatography column described in 10-20% (volume fraction) aqueous ethanolic solution continuation wash-out;
Step 5: when described 10-20% aqueous ethanolic solution flow to described chromatography column post mouth, collects elutriant, and when collecting the elutriant of 4-6 described chromatography column volume, stops carrying out wash-out to described chromatography column;
Step 6: concentrating under reduced pressure process is carried out to the described elutriant that step 5 obtains, its volume concentration is to 3% of original volume, the organic acid prepared in advance is added in obtained concentrated solution, and carry out crystallization treatment to adding the mixed solution after organic acid, wherein, in described mixed solution, organic acid concentration is 0.1-1.0%(mass concentration);
Step 7: the crystallization obtained step 6 is rinsed, filter, freezing and dry, obtain Powdered high-content EGCG, its EGCG monomer mass mark is greater than 99% (HPLC method measures: High Performance Liquid Chromatography, high performance liquid chromatography).
Further, in described step 1, the mode of dissolution process is ultrasonic or heating, and described ultrasonic or be 30min heat-up time, described Heating temperature is 60 DEG C.
Further, in described step 2, the volume ratio of 1% aqueous ethanolic solution and silica gel is 1:3.
Further, in described step 2, the silica gel of employing is the reverse silica gel of C18, and its order number is 100 orders.
Further, in described step 2, silica gel and the well-mixed wet volume density of 1% aqueous ethanolic solution are 0.75kg/L.
Further, in described step 3, the adsorption time of tea polyphenol extract thing solution and silica gel is 30min-60min.
Further, in described step 4, the volume of 1% aqueous ethanolic solution is 1-2 times of tea polyphenol extract thing liquor capacity in described step 3.
Further, in described step 6, organic acid is at least one in citric acid, oxalic acid and tartrate.
Further, in described step 6, crystallization method adopts hot saturated solution the crystallizing process under low temperature, and Tc is 4 DEG C.
Beneficial effect of the present invention is: effectively prevent in production process and use a large amount of noxious solvent, production process is environmental protection more, and solvent treatment amount is little, and operation is simple, for ester catechin EGCG and ECG that difficulty is separated, can accomplish disposable separation, good separating effect, separation efficiency is high, purification thing content is high, crystallization time is short, and product is not oxidizable, and product color is good, purity is high.
Embodiment
Be clearly and completely described the technical scheme in the embodiment of the present invention, obviously, described embodiment is only the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, the every other embodiment that those of ordinary skill in the art obtain, all belongs to the scope of protection of the invention.
Embodiment 1:
According to the preparation method of a kind of high-content EGCG of the embodiment of the present invention 1, comprise the following steps:
Step 1: with the tea polyphenol extract thing containing EGCG 90% for raw material, the quality that feeds intake is 2 kilograms, tea polyphenol extract raw material containing EGCG 90% is carried out dissolution process, solvent is pure water, obtain tea polyphenol extract thing solution, described dissolution process mode is ultrasonic or heating, and described ultrasonic or be 30min heat-up time, described Heating temperature is 60 DEG C;
Step 2: reverse for C18 silica gel is added in 1% aqueous ethanolic solution, described reverse silica gel carries out chemical reaction on the basis of purification on normal-phase silica gel, OH is substituted by OR, wherein R is the silica gel of carbochain, C18 reverse phase silica gel is the reverse phase silica gel that carbon containing numerical value is 18, the order number of described C18 reverse phase silica gel is 100 orders, the add-on of described C18 reverse phase silica gel is depending on the specification of chromatography column, the column volume of described C18 reverse phase silica gel is 47 L, the reverse silica gel of described C18 fully mixes with 1% aqueous ethanolic solution, mixed wet volume density is 0.75kg/L, the volume ratio of 1% aqueous ethanolic solution and the reverse silica gel of C18 is 1:3, 1% aqueous ethanolic solution of reverse for abundant mixed C 18 silica gel is added in pre-configured chromatography column, pressurization makes the accumulation of C18 reverse phase silica gel more firm repeatedly,
Step 3: adopt wet method upper prop, tea polyphenol extract thing solution step 1 obtained is added in described chromatography column, and on the C18 reverse phase silica gel of described tea polyphenol extract thing solution absorbs in described chromatography column, its adsorption time is 30min-60min;
Step 4: utilize 1% aqueous ethanolic solution prepared in advance to carry out wash-out to the C18 reverse phase silica gel in the chromatography column processed through step 3, the volume of described 1% aqueous ethanolic solution is 1 times of tea polyphenol extract thing liquor capacity, this elution fractions is not collected, elution process can the larger impurity of remove portion non-ester catechin, part chromatic number and polysaccharide isopolarity, when 1% aqueous ethanolic solution flow to C18 reverse phase silica gel surface 5cm, 20% aqueous ethanolic solution that utilization is prepared in advance continues the C18 reverse phase silica gel in chromatography column described in wash-out;
Step 5: when described 20% aqueous ethanolic solution flow to chromatography column mouth, start to collect elutriant, and in the elutriant situation that collection 4 described chromatographic column cylinders are long-pending, stop carrying out wash-out to described chromatography column, elutriant collecting amount is 188 L;
Step 6: by the elutriant of 4 column volumes collected in step 5, concentrating under reduced pressure is carried out by concentrating under reduced pressure pot or single-effect evaporator, its volume concentration is to 3% of original volume, obtain 6 liters of concentrated solutions, the organic acid prepared in advance is added in obtained concentrated solution, described organic acid is citric acid, and carry out crystallization treatment to adding the mixed solution after citric acid, wherein, in described mixed solution, citric acid mass concentration is 0.1%, adopt the crystallization of hot saturated solution the crystallizing process under low temperature, its Tc is 4 DEG C, leaves standstill 72h;
Step 7: the crystallisate appropriate amount of purified water flushing obtained in step 6, whizzer are filtered, then by freeze drier lyophilize, obtain pulverous EGCG, its quality is 1.4 kilograms, and its EGCG monomer content is greater than 99%.
Embodiment 2:
According to the preparation method of a kind of high-content EGCG of the embodiment of the present invention 2, comprise the following steps:
Step 1: with the tea polyphenol extract thing containing EGCG 60% for raw material, i.e. low levels tea polyphenol extract thing, select low levels tea polyphenol extract thing as raw material, avoid the loaded down with trivial details technique directly extracted from natural phant, farthest control cost, more embody the superiority of this technique simultaneously.The quality that feeds intake is 2 kilograms, and low levels tea polyphenol extract thing is carried out dissolution process, and solvent is pure water, obtain tea polyphenol extract thing solution, described dissolution process mode is ultrasonic or heating, and described ultrasonic or be 30min heat-up time, described Heating temperature is 60 DEG C;
Step 2: reverse for C18 silica gel is added in 1% aqueous ethanolic solution, described reverse silica gel carries out chemical reaction on the basis of purification on normal-phase silica gel, OH is substituted by OR, wherein R is the silica gel of carbochain, C18 reverse phase silica gel is the reverse phase silica gel that carbon containing numerical value is 18, the order number of described C18 reverse phase silica gel is 100 orders, the add-on of described C18 reverse phase silica gel is depending on the specification of chromatography column, the column volume of described C18 reverse phase silica gel is 47 L, the reverse silica gel of described C18 fully mixes with 1% aqueous ethanolic solution, mixed wet volume density is 0.75kg/L, the volume ratio of 1% aqueous ethanolic solution and the reverse silica gel of C18 is 1:3, 1% aqueous ethanolic solution of reverse for abundant mixed C 18 silica gel is added in pre-configured chromatography column, pressurization makes the accumulation of C18 reverse phase silica gel more firm repeatedly,
Step 3: adopt wet method upper prop, tea polyphenol extract thing solution step 1 obtained is added in described chromatography column, and on the C18 reverse phase silica gel of described tea polyphenol extract thing solution absorbs in described chromatography column, its adsorption time is 30min-60min;
Step 4: utilize 1% aqueous ethanolic solution prepared in advance to carry out wash-out to the C18 reverse phase silica gel in the chromatography column processed through step 3, the volume of described 1% aqueous ethanolic solution is 1 times of tea polyphenol extract thing liquor capacity, this elution fractions is not collected, elution process can the larger impurity of remove portion non-ester catechin, part chromatic number and polysaccharide isopolarity, when 1% aqueous ethanolic solution flow to C18 reverse phase silica gel surface 5cm, 15% aqueous ethanolic solution that utilization is prepared in advance continues the C18 reverse phase silica gel in chromatography column described in wash-out;
Step 5: when described 15% aqueous ethanolic solution flow to chromatography column mouth, start to collect elutriant, and in the elutriant situation that collection 5 described chromatographic column cylinders are long-pending, stop carrying out wash-out to described chromatography column, elutriant collecting amount is 235 liters;
Step 6: by the elutriant of 5 column volumes collected in step 5, concentrating under reduced pressure is carried out by concentrating under reduced pressure pot or single-effect evaporator, its volume concentration is to 3% of original volume, obtain 7 liters of concentrated solutions, the organic acid prepared in advance is added in obtained concentrated solution, described organic acid is citric acid, and carry out crystallization treatment to adding the mixed solution after citric acid, in wherein said mixed solution, citric acid mass concentration is 1%, adopt the crystallization of hot saturated solution the crystallizing process under low temperature, Tc is 4 DEG C, leaves standstill 168h;
Step 7: the crystallisate appropriate amount of purified water flushing obtained in step 6, whizzer are filtered, then by freeze drier lyophilize, obtain pulverous EGCG, its quality is 0.5 kilogram, and its EGCG monomer content is greater than 99%.
In specific implementation process, the preparation method of above-mentioned high-content EGCG is not limited only to laboratory implementation, also can implement in factorial praluction, the volume of involved quality of material and required solvent need proportionally expand by implementation process, and because this preparation method's process quantity of solvent is little, purification efficiency is high, therefore, in factorial praluction, the factors such as remover apparatus fault, the day output of described high-content EGCG can reach tonne.
In sum, by means of technique scheme of the present invention, effectively prevent in production process and use a large amount of noxious solvent, production process is environmental protection more, and solvent treatment amount is little, and operation is simple, for ester catechin EGCG and ECG that difficulty is separated, can accomplish disposable separation, good separating effect, separation efficiency is high, purification thing content is high, crystallization time is short, and product is not oxidizable, and product color is good, purity is high.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (9)
1. a preparation method of high-content EGCG, is characterized in that, comprising:
Step 1: carry out dissolution process to the tea polyphenol extract raw material containing EGCG selected in advance, solvent is pure water, obtains tea polyphenol extract thing solution;
Step 2: silica gel is added in appropriate 1% aqueous ethanolic solution prepared in advance, after fully mixing, add pre-configured chromatography column;
Step 3: tea polyphenol extract thing solution step 1 obtained is added in described chromatography column, on the silica gel of described tea polyphenol extract thing solution absorbs in described chromatography column;
Step 4: utilize 1% aqueous ethanolic solution prepared in advance, wash-out is carried out to the silica gel in the chromatography column processed through step 3, and, when this 1% aqueous ethanolic solution flow to the Silica Surface in described chromatography column, the 10-20% aqueous ethanolic solution that utilization is prepared in advance continues the silica gel in chromatography column described in wash-out;
Step 5: when described 10-20% aqueous ethanolic solution flow to described chromatography column post mouth, collects elutriant, and collecting in the long-pending elutriant situation of the individual described chromatographic column cylinder of 4-6, stops carrying out wash-out to described chromatography column;
Step 6: concentrating under reduced pressure process is carried out to the described elutriant that step 5 obtains, the organic acid prepared in advance is added in obtained concentrated solution, and carry out crystallization treatment to adding the mixed solution after organic acid, wherein, in described mixed solution, organic acid mass concentration is 0.1-1.0%;
Step 7: the crystallization obtained step 6 is rinsed, filter, freezing and dry, obtained Powdered high-content EGCG, its EGCG monomer mass percentage ratio is greater than 99%.
2. the preparation method of high-content EGCG according to claim 1, is characterized in that, in described step 1, the mode of dissolution process is ultrasonic or heating, and described ultrasonic or be 30 minutes heat-up time, described Heating temperature is 60 DEG C.
3. the preparation method of high-content EGCG according to claim 2, is characterized in that, in described step 2, the volume ratio of 1% aqueous ethanolic solution and silica gel is 1:3.
4. the preparation method of high-content EGCG according to claim 3, is characterized in that, in described step 2, the silica gel of employing is the reverse silica gel of C18, and its order number is 100 orders.
5. the preparation method of high-content EGCG according to claim 4, is characterized in that, in described step 2, silica gel and the well-mixed wet volume density of 1% aqueous ethanolic solution are 0.75kg/L.
6. the preparation method of high-content EGCG according to claim 5, is characterized in that, in described step 3, the adsorption time of tea polyphenol extract thing solution and silica gel is 30-60 minute.
7. the preparation method of high-content EGCG according to claim 6, is characterized in that, in described step 4, the volume of 1% aqueous ethanolic solution is 1-2 times of tea polyphenol extract thing liquor capacity in described step 3.
8. the preparation method of high-content EGCG according to claim 7, is characterized in that, in described step 6, organic acid is at least one in citric acid, oxalic acid and tartrate.
9. the preparation method of high-content EGCG according to claim 8, is characterized in that, in described step 6, crystallization method adopts hot saturated solution the crystallizing process under low temperature, and Tc is 4 DEG C.
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Cited By (4)
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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 |
| CN113546014A (en) * | 2021-07-26 | 2021-10-26 | 广州市百益康生物科技发展有限公司 | Method for extracting dissolved tea polyphenol and Perilla oil 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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| WO2023116209A1 (en) * | 2021-12-24 | 2023-06-29 | 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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