CN109810116A - A method of ellagic acid in purifying Chinese chestnut hair shell extracting solution - Google Patents
A method of ellagic acid in purifying Chinese chestnut hair shell extracting solution Download PDFInfo
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- CN109810116A CN109810116A CN201910140586.4A CN201910140586A CN109810116A CN 109810116 A CN109810116 A CN 109810116A CN 201910140586 A CN201910140586 A CN 201910140586A CN 109810116 A CN109810116 A CN 109810116A
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- ellagic acid
- chinese chestnut
- hair shell
- chestnut hair
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Abstract
Using the complexing of ionizable metal salt and ellagic acid, ellagic acid is purified.Method is as follows: the polyphenols such as ellagic acid in the Chinese chestnut hair shell extracting solution of extract by solvents can form co-ordination complex with ionizable metal salt under alkaline condition；Isolate complex compound；Addition and the stronger substance of ionizable metal salt sequestering power, such as EDTA, acid make metal salt-polyphenol complex compound solution complexing, release polyphenols.Pass through the different phenolic substancess purpose for realizing purifying ellagic acid different from metal ion chelating capacity.This method is easy to operate, efficient, low in cost, and pollution burden is small.
Description
Technical field
The present invention provides a kind of methods of ellagic acid in purifying Chinese chestnut hair shell extracting solution, belong to native compound purifying neck
Domain.
Background technique
Contain gallic acid, ellagic acid, shikimic acid, Quercetin, former catechin, oleanolic acid, malol in Chinese chestnut hair shell
Etc. a variety of polyphenol components.Natural plant polyphenols can improve the metabolic condition of body, reduce the morbidity of cardiovascular and cerebrovascular disease
Rate, at the same antitumor, antiviral, anti-aging, in terms of have good effect.
Containing a variety of lifes such as Polyphenols, flavonoids and carbohydrates in the extracting solution obtained using extract by solvents Chinese chestnut hair shell
Active substances, wherein ellagic acid is the maximum ingredient of content in the polyphenols of Chinese chestnut hair shell extracting solution, accounts for total phenol and contains
50% or so of amount.Therefore polyphenols in Chinese chestnut hair shell extracting solution is isolated and purified, to obtain the ellagic acid of high-purity,
Be conducive to improve the utility value of Chinese chestnut hair shell.
Ellagic acid is a kind of polyphenol dilactone, is the dimerization derivative of gallic acid.Intramolecular has big pi bond conjugated system
And the Molecular Geometries of the double hydroxyls in ortho position, determine the ability that ellagic acid phenolic hydroxyl group has very strong chelated metal ions
(the complexed-precipitation method such as Long Chunmei prepare complexing agent in Tea Polyphenols recycle and Fe3+[J] applied chemistry is influenced,
2005,22(12):1387-1389.).Under alkaline condition, phenolic hydroxyl group meeting and OH-Ion react generate accordingly bear from
Son, so that ability of the polyphenols with the complexing of very high and ionizable metal salt in alkaline medium, to generate metal salt
Ionm(phenol)nLigand, it is possible to utilize the complexing power of the phenolic substancess such as ellagic acid in extracting solution and ionizable metal salt
Difference achievees the purpose that isolate and purify ellagic acid in Chinese chestnut hair shell extracting solution.Ethylenediamine tetra-acetic acid (EDTA) is the strong of metal ion
Chelating agent, when EDTA being added in polyphenol-ionizable metal salt complex compound sediment, due to the complexing energy of EDTA and metal ion
Power is stronger, can generate (metal ion)m-EDTAnComplex compound, thus with polyphenols compete, make complexing metal ion from
The complexing of polyphenol transfers to be complexed with EDTA, and releases polyphenols.In addition, acidic environment can also destroy polyphenol-metal salt
Ionic complex, due to there is a large amount of H in acidic environment+, Polyphenols molecule is re-formed, coordinate bond is opened.Therefore it uses
EDTA can make to release polyphenols in polyphenol-metal complex in acidic environment, realize the purifying of ellagic acid.?
It can be solution with hydrochloric acid, acetic acid and ethylenediamine tetra-acetic acid (EDTA) using zinc, copper ion as complex ion in complex compound forming process
Complexing agent.
Therefore, the present invention devises a kind of utilization and forms polyphenol-ionizable metal salt complex compound, then opens complexing object space
Method, for purifying ellagic acid in Chinese chestnut hair shell extracting solution.
Summary of the invention
The purpose of the present invention is easily forming complex compound with ionizable metal salt using polyphenols, and can be deposited in decomplexing agents
When discharge the characteristic of polyphenols, develop a kind of easy, quickly and efficiently ellagic acid in purifying Chinese chestnut hair shell extracting solution
Method.
The present invention has during purifying ellagic acid without using poisonous and harmful reagent, without the dangerous behaviour such as high temperature and pressure
The characteristics of making.
The purpose of the present invention is implemented by the following technical solutions: a kind of side purifying ellagic acid in Chinese chestnut hair shell extracting solution
Method is mainly complexed using polyphenols in ionizable metal salt and Chinese chestnut hair shell extracting solution, and realizes purifying ellagic acid purpose,
Steps are as follows:
A. with 80% ethanol water extract by solvents Chinese chestnut hair shell, Chinese chestnut hair shell alcohol aqueous extract is obtained.It measures certain
The Chinese chestnut hair shell alcohol aqueous extract of amount, adjusts pH value with alkaline solution；A certain amount of ionizable metal salt solution is added, additive amount guarantees
Ellagic acid can be complexed completely, generate precipitating after being centrifugated complex reaction.The complex reaction time is 30min.Complex reaction
Temperature is 30-50 DEG C, preferably 30 DEG C；PH value used is 9-12, and preferred pH value is 9.5.Ionizable metal salt used
For zinc ion salt or copper ion salt, preferably zinc ion salt.
B. a certain amount of decomplexing agents are added in above-mentioned precipitating, additive amount guarantees that polyphenol-metal complex is dissociated, releases
Polyphenols is released, the precipitating that removal reaction generates is evaporated supernatant, obtains ellagic acid product.
Hydrochloric acid, EDTA or acetic acid, preferably hydrochloric acid can be selected in the decomplexing agents used solved in complex reaction.To plate
Solution is through efficient after supernatant and addition decomplexing agents solution are complexed after ellagic acid and zinc salt are complexed in chestnut hair shell extracting solution, extracting solution
Liquid-phase chromatographic analysis obtains chromatogram and sees attached drawing.The chromatographic condition of use are as follows: chromatographic column is Agilent Eclipse Plus
C18 (4.6mm × 250mm, 5 μm), mobile phase are -0.1% aqueous formic acid of methanol, carry out gradient elution (0min, 15:85v/
v；10min, 30:70v/v；15min, 45:55v/v；18min, 65:35v/v；30min, 15:85v/v；), flow velocity is 1.0m L/
Min, Detection wavelength 254nm, 10 μ L of sample volume, column temperature is room temperature.
The present invention achieves following beneficial achievement:
1, in Chinese chestnut hair shell of the invention ellagic acid purification process, it is cheap using reagent price, without poisonous and harmful reagent,
The burden caused by environment is small；
2, purification process of the invention is easy to operate, is being simply mixed and separating for room temperature, no high temperature and pressure operation, peace
Good perfection.
Detailed description of the invention
Fig. 1 is ellagic acid structural formula.
Fig. 2 is ellagic acid complexing zinc salt ionic structure formula.
Fig. 3 is extracting solution, supernatant and solution after the complexing of hydrochloric acid solution is added after ellagic acid and zinc salt complexing in extracting solution
High-efficient liquid phase chromatogram.
Fig. 4 is extracting solution, supernatant and solution after the complexing of hydrochloric acid solution is added after ellagic acid and mantoquita complexing in extracting solution
High-efficient liquid phase chromatogram.
Specific embodiment:
With reference to the accompanying drawing with specific embodiment to ellagic acid in a kind of purifying Chinese chestnut hair shell extracting solution of the invention
Method further illustrates, so that those skilled in the art becomes more apparent upon the present invention, but does not limit the present invention with this.
Case study on implementation 1
A. 10mL Chinese chestnut hair shell extracting solution is measured, adjusting pH value is 9.5, and certain mass concentration ZnSO is added4Solution, addition
Amount guarantees that can (molar ratio 1:1) be complexed completely in ellagic acid.After addition, the complex reaction time is 30min.Complex reaction temperature
Degree is 30 DEG C, generates precipitating after being centrifugated complex reaction；
B. 200 μ L hydrochloric acid being added in above-mentioned precipitating, additive amount guarantees that complex compound is hydrolyzed, after ultrasound solution complexing, centrifugation
The precipitating generated after separation solution complex reaction, is evaporated supernatant, obtains ellagic acid product.Through detecting, the tan flower in purification process
Acid content in extract is improved from 2.59% to 10.01%, and the ellagic acid rate of recovery is 82.83%.
Case study on implementation 2
A. 10mL Chinese chestnut hair shell extracting solution is measured, adjusting pH value is 9.5, and certain mass concentration ZnSO is added4Solution, addition
Amount guarantees that can (molar ratio 1:1) be complexed completely in ellagic acid.After addition, the complex reaction time is 30min.Complex reaction temperature
Degree is 40 DEG C, generates precipitating after being centrifugated complex reaction；
B. 400 μ L acetic acid are added in above-mentioned precipitating, guarantee that complex compound is hydrolyzed, after ultrasound solution complexing, centrifuge separation solution
The precipitating generated after complex reaction is evaporated supernatant, obtains ellagic acid product.Through detecting, ellagic acid is being mentioned in purification process
Content in object is taken to improve from 2.59% to 9.51%, the ellagic acid rate of recovery is 81.54%.
Case study on implementation 3
A. 10mL Chinese chestnut hair shell extracting solution is measured, adjusting pH value is 9.5, and certain mass concentration ZnSO is added4Solution, addition
Amount guarantees that can (molar ratio 1:1) be complexed completely in ellagic acid.After addition, the complex reaction time is 30min.Complex reaction temperature
Degree is 50 DEG C, generates precipitating after being centrifugated complex reaction；
B. the EDTA of molar ratio (1:1) is added in above-mentioned precipitating, after ultrasound solution complexing, after centrifuge separation solution complex reaction
The precipitating of generation is evaporated supernatant, obtains ellagic acid product.Through detecting, ellagic acid content in extract in purification process
It improves from 2.59% to 9.58%, the ellagic acid rate of recovery is 83.73%.
Case study on implementation 4
A. 10mL Chinese chestnut hair shell extracting solution is measured, adjusting pH value is 12, and certain mass concentration ZnSO is added4Solution, addition
Amount guarantees that can (molar ratio 1:1) be complexed completely in ellagic acid.After addition, the complex reaction time is 30min.Complex reaction temperature
Degree is 50 DEG C, generates precipitating after being centrifugated complex reaction；
B. the EDTA of molar ratio (1:1) is added in above-mentioned precipitating, after ultrasound solution complexing, after centrifuge separation solution complex reaction
The precipitating of generation is evaporated supernatant, obtains ellagic acid product.Through detecting, ellagic acid content in extract in purification process
It improves from 2.59% to 8.41%, the ellagic acid rate of recovery is 75.11%.
Case study on implementation 5
A. 10mL Chinese chestnut hair shell extracting solution is measured, adjusting pH value is 12, and certain mass concentration ZnCl is added2Solution, addition
Amount guarantees that can (molar ratio 1:1) be complexed completely in ellagic acid.After addition, the complex reaction time is 30min.Complex reaction temperature
Degree is 30 DEG C, generates precipitating after being centrifugated complex reaction；
B. molar ratio: the EDTA of (1:1) is added in above-mentioned precipitating, after ultrasound solution complexing, centrifuge separation solution complex reaction
The precipitating generated afterwards is evaporated supernatant, obtains ellagic acid product.Through detecting, ellagic acid contains in extract in purification process
Amount is improved from 2.59% to 9.56%, and the ellagic acid rate of recovery is 72.98%.
Case study on implementation 6
A. 10mL Chinese chestnut hair shell extracting solution is measured, adjusting pH value is 9.5, and certain mass concentration C uSO is added4Solution, addition
Amount guarantees that can (molar ratio 1:1) be complexed completely in ellagic acid.After addition, the complex reaction time is 30min.Complex reaction temperature
Degree is 30 DEG C, generates precipitating after being centrifugated complex reaction；
B. the hydrochloric acid of 200 μ L is added in above-mentioned precipitating, guarantees that complex compound is hydrolyzed, it is raw after centrifuge separation solution complex reaction
At precipitating, be evaporated supernatant, obtain ellagic acid product.Through detecting, in purification process ellagic acid in extract content from
2.59% improves to 5.23%, and the ellagic acid rate of recovery is 81.88%.
Case study on implementation 7
A. 10mL Chinese chestnut hair shell extracting solution is measured, adjusting pH value is 9.5, and certain mass concentration C uSO is added4Solution, addition
Amount guarantees that can (molar ratio 1:1) be complexed completely in ellagic acid.After addition, the complex reaction time is 30min.Complex reaction temperature
Degree is 30 DEG C, generates precipitating after being centrifugated complex reaction；
B. 200 μ L acetic acid are added in above-mentioned precipitating, after ultrasound solution complexing, it is heavy to generate after centrifuge separation solution complex reaction
It forms sediment, is evaporated supernatant, obtain ellagic acid product.Through detecting, in purification process ellagic acid in extract content from 2.59%
It improves to 7.35%, the ellagic acid rate of recovery is 17.13%.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (5)
1. a kind of method of ellagic acid in purifying Chinese chestnut hair shell extracting solution, it is characterised in that:
A. Chinese chestnut hair shell is extracted with alcohol water-soluble fluorine, obtains Chinese chestnut hair shell alcohol aqueous extract, alcohol solution used is 80% second
Alcohol solution；
B. a certain amount of Chinese chestnut hair shell alcohol aqueous extract is measured, adjusts pH value with alkaline solution；A certain amount of ionizable metal salt is added
Solution, additive amount guarantee that ellagic acid can be complexed completely, generate precipitating after being centrifugated complex reaction, the complex reaction time is
30min；
C. a certain amount of decomplexing agents are added in above-mentioned precipitating, additive amount guarantees that polyphenol-metal complex is dissociated, releases
Polyphenols, the precipitating that removal reaction generates, is evaporated supernatant, obtains ellagic acid product.
2. the method for ellagic acid in a kind of purifying Chinese chestnut hair shell extracting solution according to claim 1, it is characterised in that: complexing
Reaction solution pH be 9-12, preferably 9.5.
3. the method for ellagic acid in a kind of purifying Chinese chestnut hair shell extracting solution according to claim 1, it is characterised in that: complexing
Zinc ion salt or copper ion salt, preferably zinc ion salt can be selected in ionizable metal salt in reaction.
4. the method for ellagic acid in a kind of purifying Chinese chestnut hair shell extracting solution according to claim 1, it is characterised in that: complexing
The temperature of reaction can be 30-50 DEG C, preferably 30 DEG C.
5. the method for ellagic acid in a kind of purifying Chinese chestnut hair shell extracting solution according to claim 1, it is characterised in that: decomplexing
Hydrochloric acid, EDTA, acetic acid, preferably hydrochloric acid can be selected in the decomplexing agents closed in reaction.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112891442A (en) * | 2021-03-27 | 2021-06-04 | 广州础研网络科技有限公司 | Method for extracting polyphenol substances from plantain leaf and stem scales |
| CN114605427A (en) * | 2022-03-25 | 2022-06-10 | 大连理工大学盘锦产业技术研究院 | Method for extracting and preparing raspberry ellagic acid |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1478523A (en) * | 1966-03-11 | 1967-04-28 | Prod Chim Et Celluloses Rey | Ellagic acid purification process |
| CN1429097A (en) * | 2000-05-18 | 2003-07-09 | 欧莱雅 | Use of ellagic acid as anti-pollution cosmetic agent |
| CN102579516A (en) * | 2012-03-07 | 2012-07-18 | 齐齐哈尔大学 | Method for separating purified seabuckthorn flavonoid from large berry seabuckthorn marc |
| CN107759648A (en) * | 2017-11-02 | 2018-03-06 | 北京理工大学 | A kind of method that Hyperoside and isoquercitrin are isolated and purified from Golden flower |
| CN108101924A (en) * | 2018-01-03 | 2018-06-01 | 北京理工大学 | A kind of method that ellagic acid is extracted in the hair shell from Chinese chestnut |
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2019
- 2019-02-26 CN CN201910140586.4A patent/CN109810116B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1478523A (en) * | 1966-03-11 | 1967-04-28 | Prod Chim Et Celluloses Rey | Ellagic acid purification process |
| CN1429097A (en) * | 2000-05-18 | 2003-07-09 | 欧莱雅 | Use of ellagic acid as anti-pollution cosmetic agent |
| CN102579516A (en) * | 2012-03-07 | 2012-07-18 | 齐齐哈尔大学 | Method for separating purified seabuckthorn flavonoid from large berry seabuckthorn marc |
| CN107759648A (en) * | 2017-11-02 | 2018-03-06 | 北京理工大学 | A kind of method that Hyperoside and isoquercitrin are isolated and purified from Golden flower |
| CN108101924A (en) * | 2018-01-03 | 2018-06-01 | 北京理工大学 | A kind of method that ellagic acid is extracted in the hair shell from Chinese chestnut |
Non-Patent Citations (1)
| Title |
|---|
| S.R. PRZEWLOKA等: "The Further Chemistry of Ellagic Acid II. Ellagic Acid and Water-Soluble Ellagates as Metal Precipitants", 《HOLZFORSCHUNG》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112891442A (en) * | 2021-03-27 | 2021-06-04 | 广州础研网络科技有限公司 | Method for extracting polyphenol substances from plantain leaf and stem scales |
| CN114605427A (en) * | 2022-03-25 | 2022-06-10 | 大连理工大学盘锦产业技术研究院 | Method for extracting and preparing raspberry ellagic acid |
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