CN101712669A - Method for separating and purifying luteolin - Google Patents
Method for separating and purifying luteolin Download PDFInfo
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- CN101712669A CN101712669A CN200910004229A CN200910004229A CN101712669A CN 101712669 A CN101712669 A CN 101712669A CN 200910004229 A CN200910004229 A CN 200910004229A CN 200910004229 A CN200910004229 A CN 200910004229A CN 101712669 A CN101712669 A CN 101712669A
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Abstract
The invention aims to provide a material for preparing a molecular imprinted polymer by taking luteolin as a template and adopting a molecular imprinting technique method, and a method for separating and purifying the luteolin in a natural product, and belongs to the field of separation and purification of effective components from the natural product. The method comprises the following steps: (1) crude extraction, namely sequentially washing, drying, crushing and sieving peanut shells, extracting the peanut shell powder with 70 percent ethanol time by time under the assistance of ultrasonic waves, and concentrating and drying the extract; (2) preparation of the polymer, namely weighing the pure luteolin, a functional monomer, a cross-linking agent and an initiating agent in proportion, dissolving the materials in a solvent, performing ultrasonic processing, degassing and polymerization on the solution to obtain the block polymer, and sequentially grinding, sieving and eluting the block polymer to obtain the molecular imprinted polymer of the luteolin; and (3) purification, namely loading the prepared molecular imprinted polymer into a solid-phase extraction column, loading the crude extract, washing off the luteolin left on the column after removing impurities by eluting, concentrating and drying the luteolin to obtain the pure product of the luteolin.
Description
Affiliated technical field:
What patent of the present invention related to is the separation and the purifying of luteolin in the natural phant, belongs to active ingredient of natural product separation and purification field.
Luteolin is a kind of very representative natural flavone, belongs to slightly acidic kaempferol compounds, and is distributed more widely in vegitabilia, has very high biological activity.
Luteolin has very strong anti-oxidant activity, has effect antibiotic, antiviral and blood fat reducing and cholesterol in vivo; Luteolin also is antineoplastic startup factor, studies confirm that it has remarkable restraining effect to multiple solid tumor, ascites carcinoma and leukemia cell; Luteolin can also the multiple antiapoptotic factors that causes of enhanced sensitivity, has the antineoplastic potentiality of many target spots.
Inflammation plays an important role in many neurodegenerative disorders, studies show that luteolin (can hinder the inflammatory reaction of neural system several cells in addition, thereby reduce the forgetful and fragmentation that the inflammatory reaction in the brain relevant with aging causes because of aging with improvement.This discovery may exert an influence to the disease as senile dementia and multiple sclerosis and so on.
Luteolin extracts from plant, and the purity of the luteolin that conventional separation method obtains is not high, and medicinal luteolin requires purity very high, and therefore, it is just extremely important to set up separation purification method efficient and luteolin cheaply.
Background technology:
Luteolin belongs to flavonoid, Flavonoid substances has the natural product that the C6-C3-C6 structure is basic parent nucleus, they have similar physicochemical property, they are present in the natural phant simultaneously, as also contain Flavonoid substances (see figure 1)s such as eriodictyol, dihydroxyl chromone in the Pericarppium arachidis hypogaeae except that containing luteolin.
The method of extracting luteolin from natural phant has lixiviate, ooze cross, refluxing extraction, Soxhlet extraction, supercritical fluid extraction, enzymolysis, ultrasonic extraction, the microwave extracting etc. of helping.But the extraction product that adopts above-mentioned each method to obtain is a total flavonoid, can't obtain the higher luteolin of purity.Method to the further separation and purification of luteolin has high performance liquid chromatography and chromatography at present, though these two kinds of methods have higher separation efficiency, the liquid chromatography instrument costliness that liquid phase chromatography needs, extracted amount is limited, chromatographically pure moving phase consumption is big, and working cost is very high.The silica gel of chromatography can't be reused, and needs a large amount of solvents, so separation costs is also very high.
Molecular imprinting is in the presence of linking agent, to have the free radical polymerization of uv-radiation or heat effect, function monomer carries out polymerization round template molecule or microsphere, after polyreaction is finished, or with hydrolysis or carry out gentleness extraction with suitable solvent and remove covalent linkage or non covalent bond bonded template molecule, the polymkeric substance of the tridimensional network that obtains, i.e. molecularly imprinted polymer (MIPs) with special identification hole.Hole or the trace stayed on the polymkeric substance are complementary with template molecule on shape, size and function, and permanent memory effect is arranged.Molecularly imprinted polymer has the special recognition site of affinity structure for the template molecule that is adopted, and can with template molecule with the mode of action of host-guest bonding again optionally.Therefore this polymkeric substance has good effect for template molecule is separated from the complex system that contains template molecule.Separating or analyze medium and compare with conventional and traditional, is that separated object or analyte are had selectivity highly based on the outstanding feature of the molecularly imprinted polymer of molecular recognition.Simultaneously molecularly imprinted polymer prepares easyly, has good physical and chemical stability, can withstand high temperatures, high pressure, soda acid organic solvent etc., preserve easily, and under conventional envrionment temperature, can preserve several years and do not reduce post and imitate.Therefore, polymkeric substance can reuse up to a hundred times and preserve " memory " effect, has unique advantage.Be easy to realize suitability for industrialized production.
Summary of the invention:
The purpose of this invention is to provide a kind of molecular imprinting method that adopts is the material that template prepares molecularly imprinted polymer with the luteolin, and with this plant extraction liquid that contains luteolin is carried out the separation and purification luteolin.
Technical scheme of the present invention is:
This is used to separate, the moiety and the weight proportion of the molecular engram material of purifying luteolin are as follows:
Template molecule is a luteolin: 2～3%;
Function monomer is acrylamide (2.5～3.0%), also can adopt 4-vinylpridine (4.0～4.5%), 2-vinylpyridine (4.0～4.5%) or 2, and 6-diacrylamine pyridine (3.0～4.0%) etc. are as function monomer of the present invention.
Linking agent is an ethylene glycol dimethacrylate (EDMA) (30～35%), also can adopt N, N '-methylene diacrylamine (23～27%), divinylbenzene (20～25%), pentaerythritol triacrylate (PETRA) (30～35%) and trimethoxy propane trimethyl acrylic ester (TRIM) materials such as (28～33%) also can be used as linking agent of the present invention.
Initiator can be selected Diisopropyl azodicarboxylate (AIBN), 2,2'-Azobis(2,4-dimethylvaleronitrile) or benzoyl peroxide for use, and consumption all is about 0.1%.
Solvent is selected acetone or acetonitrile for use, and after the content of above-mentioned each composition was determined, adding solvent was 100%.
Specific embodiments:
1, the pre-treatment of raw material
(1) Pericarppium arachidis hypogaeae is cleaned up back oven dry, pulverizing, cross 40 mesh sieves, be stored in the dry environment, standby.
(2) take by weighing peanut hull meal, get 70% ethanol that 10-15 doubly measures, at normal temperatures, adopt the ultrasonic wave auxiliary law, divide three subgradients to extract, each 15min through 45min as extracting solvent.
(3) three ethanol extracts of collecting are evaporated near doing with rotatory evaporator,, get the Pericarppium arachidis hypogaeae ethanol extraction, put into moisture eliminator after the sealing and preserve concentrated solution nature or vacuum-drying.
2, the preparation of luteolin molecularly imprinted polymer
In container (test tube), take by weighing luteolin, function monomer, linking agent and initiator by the above-mentioned proportioning raw materials that provides, fully be dissolved in the solvent, it was carried out ultrasonic 10-30 minute; To fill the container sealing of above-mentioned solution then, logical argon gas or nitrogen carry out deoxidation, with the container of good seal 60 ℃ of following constant temperature polymerizations 24 hours; After polymerization is finished, bulk polymer in the container is ground, sieves, use 90% (v/v) methanol acetic acid solvent elution to remove template molecule, do not have polymeric function monomer, linking agent and initiator then, obtain luteolin molecularly imprinted polymer (MIP).
The process of the preparation of non-template imprinted polymer (NMIP) as a comparison is not except that adding the luteolin template molecule, and other step is identical with the preparation of imprinted polymer (MIP).
3, separation and the purifying to containing the luteolin crude extract
With the molecularly imprinted polymer dress post that makes, and use wetted with methanol.The plant extraction liquid upper prop that will contain luteolin, and the impurity in the crude extract is eluted (checking with thin-layer chromatography) fully with 10% methanol aqueous solution, use methyl alcohol then: the luteolin that the solution of acetate (9: 1) will be retained on the post elutes (checking with thin-layer chromatography), obtains the luteolin straight product through concentrated, drying.
The present invention has following advantage:
1, molecularly imprinted polymer of the present invention is the template preparation with the luteolin, the hole of polymkeric substance and luteolin bulk of molecule are consistent, its binding site also is complementary with the luteolin molecule, has very high selectivity, can reach good separating effect.
2, Zhi Bei polymkeric substance has very high intensity and stability, can reuse.Avoided the mass consumption problem of the silica gel in the silica gel separation and purification.
3, because the molecularly imprinted polymer of preparation has good recognition performance to luteolin, the solvent load of drip washing and wash-out also greatly reduces, and has reduced separation costs.
Example 1
1, the preparation of luteolin molecularly imprinted polymer
Taking by weighing 0.731g luteolin, 0.706g acrylamide, 10g pentaerythritol triacrylate (PETRA) and 0.03g 2,2'-Azobis(2,4-dimethylvaleronitrile) is dissolved in the 20ml acetone, ultrasonic in beaker, solution is poured in the sealable container (test tube) then, sealed, logical Ar
260 ℃ water bath with thermostatic control polymerization is put into the container of good seal in deoxidation.The preparation of blank polymkeric substance (NMIPs) is not except that adding the template molecule luteolin, and other is all identical.After polymerization is finished, the bulk polymer in the container is pounded into fritter, and grinding, obtaining particulate polymers.Use methyl alcohol: the solution of acetate (9: 1) carries out wash-out to be removed and does not participate in polymeric solvent, initiator and template molecule, obtains the luteolin molecularly imprinted polymer.
2, the separation of luteolin concentrated solution and purifying
The good luteolin imprinted polymer that takes by weighing the 3g wash-out is packed in the solid-phase extraction column, adds a little quartz sand on the post upper strata after having adorned post, uses the wetting pillar of amount of methanol then.Pipette 15ml Pericarppium arachidis hypogaeae ethanol extract (0.5g/ml) upper prop, and pressurize to post, add leacheate (10% methyl alcohol) when treating liquid level and carry out drip washing, until the impurity in the Pericarppium arachidis hypogaeae ethanol extraction is eluted (checking with thin-layer chromatography) fully a little more than solidus surface.Use methyl alcohol then: acetate (9: 1) eluant solution is adsorbed on the luteolin (checking with thin-layer chromatography) on the column extractor, obtains the luteolin straight product through concentrated, drying.
Example 2
1, the preparation of luteolin molecularly imprinted polymer
Take by weighing 0.713g luteolin, 0.883g 2,6-diacrylamine pyridine, 10g EDMA and 0.03g AIBN are dissolved in the 20ml acetone, and be ultrasonic in beaker, then solution poured in the sealable container (flask at the bottom of the garden), seals, logical Ar
260 ℃ water bath with thermostatic control polymerization is put into the container of good seal in deoxidation.The preparation of blank polymkeric substance (NMIPs) is not except that adding the template molecule luteolin, and other is all identical.After polymerization is finished, the bulk polymer in the container is pounded into fritter, and grinding, obtaining particulate polymers.Use methyl alcohol: the solution of acetate (9: 1) carries out wash-out to be removed and does not participate in polymeric solvent, initiator and template molecule, obtains the luteolin molecularly imprinted polymer.
2, the separation of luteolin concentrated solution and purifying
The good luteolin imprinted polymer that takes by weighing the 2g wash-out is packed in the solid-phase extraction column, adds a little quartz sand on the post upper strata after having adorned post, uses the wetting pillar of amount of methanol then.Pipette 10ml Pericarppium arachidis hypogaeae ethanol extract (0.6g/ml) upper prop, and, when treating liquid level, carry out drip washing, until the impurity in the Pericarppium arachidis hypogaeae ethanol extraction is eluted (checking with thin-layer chromatography) fully with 10% methyl alcohol leacheate a little more than solidus surface to the post pressurization.Use methyl alcohol then: acetate (9: 1) eluant solution is adsorbed on the luteolin (checking with thin-layer chromatography) on the column extractor, obtains the luteolin straight product through concentrated, drying.
Description of drawings:
The structure of letones in Fig. 1 Pericarppium arachidis hypogaeae
The basic parent nucleus b of a, Flavonoid substances, the structure of luteolin
The structure of the structure d of c, eriodictyol, dihydroxyl chromone
The synthetic synoptic diagram of the plain molecularly imprinted polymer of Fig. 2 rhinoceros grass
The mode of appearance sem photograph of Fig. 3 polymkeric substance
A and c, luteolin imprinted polymer b and d, non-imprinted polymer
The equilibrium adsorption figure of Fig. 4 polymkeric substance
A, imprinted polymer absorption b, the absorption of non-imprinted polymer
The ultraviolet-visible spectrogram of Fig. 5 luteolin in 0.01% methanol solution solution
The luteolin that a, luteolin standard substance b, separation obtain
Fig. 6 separates the infrared spectrogram of the luteolin that obtains.
Claims (10)
1. the purpose of this invention is to provide a kind of molecular imprinting method that adopts is the material that template prepares molecularly imprinted polymer with the luteolin, and carry out the separation and purification of luteolin with this extracting solution to the natural product that contains luteolin, it is characterized in that, may further comprise the steps:
(1) slightly carries: Pericarppium arachidis hypogaeae is cleaned, dries, pulverizes, sieve; Down auxiliary in ultrasonic wave, extract with 70% ethanol gradation; Extracting solution is concentrated, dry, slightly carried product.
(2) polymer manufacture: take by weighing pure product luteolin, function monomer, linking agent and initiator by proportioning, be dissolved in the solvent, obtain bulk polymer, it is ground, sieves through ultrasonic, the degassing, polymerization, wash-out obtains the luteolin molecularly imprinted polymer.
(3) purifying: with the molecularly imprinted polymer that the makes solid-phase extraction column of packing into, with sample on the crude extract, after wash-out was removed impurity, the luteolin that will be retained in again on the post washed, through concentrating, drying obtains the luteolin straight product.
2. according to the requirement of claim 1, Pericarppium arachidis hypogaeae is cleaned up the back oven dry, pulverizes, cross 40 mesh sieves, be stored in the dry environment, standby.
3. according to the requirement of claim 1, take by weighing peanut hull meal, get 70% ethanol that 10-15 doubly measures, at normal temperatures, adopt the ultrasonic wave auxiliary law, divide three subgradients to extract, each 15min through 45min as extracting solvent.
4. according to the requirement of claim 1, the template template molecule of molecularly imprinted polymer adopts luteolin, and weight proportion is 2～3%.
5. according to the requirement of claim 1, the function monomer of polymkeric substance adopts acrylamide (2.5～3.0%), also can adopt 4-vinylpridine (4.0～4.5%), 2-vinylpyridine (4.0～4.5%) or 2,6-diacrylamine pyridine (3.0～4.0%) etc. are as function monomer of the present invention.
6. according to the requirement of claim 1, the polymeric linking agent is an ethylene glycol dimethacrylate (EDMA) (30～35%), also can adopt N, N '-methylene diacrylamine (23～27%), divinylbenzene (20～25%), pentaerythritol triacrylate PETRA) (30～35%) and trimethoxy propane trimethyl acrylic ester (TRIM) materials such as (28～33%) also can be used as linking agent of the present invention.
7. according to the requirement of claim 1, initiator can be selected Diisopropyl azodicarboxylate (AIBN), 2,2'-Azobis(2,4-dimethylvaleronitrile) or benzoyl peroxide for use, and consumption all is about 0.1%.
8. according to the requirement of claim 1, the polymeric solvent can be selected acetone or acetonitrile for use.
9. according to the requirement of claim 1, the methanol aqueous solution wash-out of employing 10% is removed the impurity in the crude extract in the Solid-Phase Extraction.
10. according to the requirement of claim 1, use methyl alcohol in the Solid-Phase Extraction: the eluant solution of acetate (9: 1) is retained in the luteolin on the post.
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| CN2009100042291A CN101712669B (en) | 2009-02-13 | 2009-02-13 | Method for separating and purifying luteolin |
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| CN2009100042291A CN101712669B (en) | 2009-02-13 | 2009-02-13 | Method for separating and purifying luteolin |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102040579A (en) * | 2011-01-25 | 2011-05-04 | 彭国平 | Method for extracting luteolin from peanut roots, stems, leaves and shells |
| CN102659982A (en) * | 2012-05-24 | 2012-09-12 | 国际竹藤中心 | Flavone magnetic molecularly imprinted polymer, preparation of flavone magnetic molecularly imprinted polymer, and application of flavone magnetic molecularly imprinted polymer to bamboo-leaf flavone separation |
| CN102671639A (en) * | 2012-05-24 | 2012-09-19 | 国际竹藤中心 | Bamboo-leaf-flavonoids molecular imprinted solid-phase extraction column, preparation and application thereof |
| CN103524677A (en) * | 2013-09-30 | 2014-01-22 | 山西医科大学 | Galangin molecular imprinting polymer, and preparation method and application thereof |
| CN103933111A (en) * | 2013-05-02 | 2014-07-23 | 杭州耐奇睿生物医药科技有限公司 | Application of peanut extract |
| CN104546997A (en) * | 2013-10-16 | 2015-04-29 | 浙江中医药大学 | Method for extracting and purifying effective parts of peanut shells |
| CN104906171A (en) * | 2015-04-13 | 2015-09-16 | 沈阳北苑医药有限公司 | Process for extracting total flavonoids from peanut shells |
| CN105130939A (en) * | 2015-08-31 | 2015-12-09 | 桂林三宝生物科技有限公司 | Method for extracting luteolin from peanut shells |
| CN106588848A (en) * | 2016-11-15 | 2017-04-26 | 浙江工业大学 | Method for extracting luteolin from peanut shells |
| CN108864022A (en) * | 2017-10-13 | 2018-11-23 | 昌邑市银江生物科技有限公司 | A method of high-purity luteolin is prepared using ferrous salt |
| CN108864021A (en) * | 2017-10-13 | 2018-11-23 | 昌邑市银江生物科技有限公司 | A method of high-purity luteolin is prepared using zinc salt |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1919843A (en) * | 2006-09-19 | 2007-02-28 | 天津大学 | Preparation method of siliceous inorganic flavonoid molecular engram microsphere |
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2009
- 2009-02-13 CN CN2009100042291A patent/CN101712669B/en not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102040579A (en) * | 2011-01-25 | 2011-05-04 | 彭国平 | Method for extracting luteolin from peanut roots, stems, leaves and shells |
| CN102659982A (en) * | 2012-05-24 | 2012-09-12 | 国际竹藤中心 | Flavone magnetic molecularly imprinted polymer, preparation of flavone magnetic molecularly imprinted polymer, and application of flavone magnetic molecularly imprinted polymer to bamboo-leaf flavone separation |
| CN102671639A (en) * | 2012-05-24 | 2012-09-19 | 国际竹藤中心 | Bamboo-leaf-flavonoids molecular imprinted solid-phase extraction column, preparation and application thereof |
| CN102659982B (en) * | 2012-05-24 | 2014-09-10 | 国际竹藤中心 | Flavone magnetic molecularly imprinted polymer, preparation of flavone magnetic molecularly imprinted polymer, and application of flavone magnetic molecularly imprinted polymer to bamboo-leaf flavone separation |
| CN103933111A (en) * | 2013-05-02 | 2014-07-23 | 杭州耐奇睿生物医药科技有限公司 | Application of peanut extract |
| CN103524677A (en) * | 2013-09-30 | 2014-01-22 | 山西医科大学 | Galangin molecular imprinting polymer, and preparation method and application thereof |
| CN104546997A (en) * | 2013-10-16 | 2015-04-29 | 浙江中医药大学 | Method for extracting and purifying effective parts of peanut shells |
| CN104906171A (en) * | 2015-04-13 | 2015-09-16 | 沈阳北苑医药有限公司 | Process for extracting total flavonoids from peanut shells |
| CN105130939A (en) * | 2015-08-31 | 2015-12-09 | 桂林三宝生物科技有限公司 | Method for extracting luteolin from peanut shells |
| CN106588848A (en) * | 2016-11-15 | 2017-04-26 | 浙江工业大学 | Method for extracting luteolin from peanut shells |
| CN106588848B (en) * | 2016-11-15 | 2019-10-18 | 浙江工业大学 | The method of luteolin is extracted in a kind of peanut shell |
| CN108864022A (en) * | 2017-10-13 | 2018-11-23 | 昌邑市银江生物科技有限公司 | A method of high-purity luteolin is prepared using ferrous salt |
| CN108864021A (en) * | 2017-10-13 | 2018-11-23 | 昌邑市银江生物科技有限公司 | A method of high-purity luteolin is prepared using zinc salt |
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| CN101712669B (en) | 2012-01-18 |
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