CN103224590B - Glabridin molecularly imprinted polymer, as well as preparation method and application thereof - Google Patents
Glabridin molecularly imprinted polymer, as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a glabridin molecularly imprinted polymer, as well as a preparation method and application thereof. The preparation method comprises the following steps of: taking glabridin as a template, adding the template, functional monomers, a cross-linking agent, an initiator and a solvent into a reaction kettle according to the mass ratio of (1-3): (2-8): (15-30): (0.05-0.2): (20-50), mixing, performing ultrasonic degassing, then charging nitrogen, removing oxygen, sealing, and then polymerizing for 10-24h in a constant-temperature water bath at the temperature of 40-60 DEG C to obtain the glabridin molecularly imprinted polymer with template molecules; and grinding, eluting and drying the obtained polymer to obtain the molecularly imprinted polymer for purifying the glabridin. The obtained glabridin molecularly imprinted polymer can be used as column chromatography packing for column packing so as to be applied in extraction of the glabridin from glycyrrhiza glabra, and the glabridin molecularly imprinted polymer has the advantages of strong selectivity, high adsorption capacity and high purity of the obtained glabridin.
Description
Technical field
The invention belongs to the preparation field of natural product or bioactive ingredients, particularly a kind of molecularly imprinted polymer for glabridin of purifying and its preparation method and application.
Background technology
Glabridin (Glabridin) molecular formula is C
20h
20o
4, molecular weight 324.37 is a kind of natural antioxidantss, and it is the flavanone compound of separation and Extraction from medicinal plant glycyrrhiza glabra (Glycyrrhiza Glabra L.).It demonstrates very strong Green Tea Extract oxygenizement in Cytochrome P450/NADPH oxidation system, obviously can suppress the free radical produced in body intracellular metabolic process, with from the biomacromolecule (low-density lipoprotein LDL, DNA) to oxidation-sensitive and cell walls etc. by Free radicals injury.Thus some pathological change relevant with free-radical oxidn can be prevented and treated, and as atherosclerosis, cell aging etc.Meanwhile, glabridin still has certain reducing blood-fat and hypotensive activity.In addition, at makeup circle, be called as the deep enough skin inside of glabridin energy of " whitening gold " and keep high reactivity, the activity of multiple enzyme in effective check melanin generative process, particularly suppressing Tyrosine enzyme activity.There is whitening, high-efficiency antioxidant, prevent pachylosis, anti-inflammatory, antibacterial effect.Glabridin safety non-toxic, even if life-time service, also harmless.Industrially glabridin is typically used as cosmetics additive and medical material.
The traditional technology many employings organic reagent producing glabridin extracts, and extraction, the operations such as column chromatography for separation, the glabridin content obtained like this is low, and cost is high.And high-purity glabrene purification step is comparatively loaded down with trivial details, the production cycle is long, and preparation amount is little, and organic solvent consumption is large, causes commodity price to remain high.If Okada etc. is at " Chemical & PharmaceuticalBulletin " (Vol.37, No.9, 1989, 2528 ~ 2530) delivered on " Identification of antimicrobial andantioxidant constituents from licorice of Russian and Xinjiang origin. ", glycyrrhiza glabra root methylene dichloride room temperature is extracted by author, extracting solution is concentrated into dry brown medicinal extract, silica gel column chromatography is separated rough segmentation, reverse silica gel column chromatography is separated again, benzol-cyclohexane recrystallization, obtain glabridin sterling.Ma Shuyan etc. deliver on " research and development of natural products " (Vol.19,2007,675 ~ 677) " in Radix Glycyrrhizae the extraction of glabridin and anti-oxidant activity research ", and this research acetone extraction glycyrrhiza glabra, after evaporate to dryness acetone, gained medicinal extract is through Al
2o
3post, preparative thin layer plate is separated, and finally obtains high-purity glabrene with benzol-cyclohexane recrystallization.
Molecular imprinting is also called molecular imprinting technique, belongs to an interdisciplinary field between polymer chemistry, Materials science, biological chemistry, analytical chemistry etc.Molecular imprinting is the experiment technology of preparing for obtaining the polymkeric substance mated completely with certain a part (being commonly referred to template molecule) on space structure and binding sites.Molecularly imprinted polymer refers to target molecule to be template molecule, the functionalized polymer monomer with complementary structure is combined with template molecule by mode covalently or non-covalently, add linking agent and carry out polyreaction, after having reacted, template molecule being extracted a kind of of rear formation has fixed cavitation size and shape and has the cross-linked high polymer determining that arranging functional is rolled into a ball.Why molecular imprinting develops so rapidly, mainly because it has precordainment, identity and practicality.Because MIPs has the ability of anti-adverse environment, show the advantages such as the strong and long service life of stability, therefore to its synthesis and applied research very active, the wide range related to, as chiral material is separated, biosensor, analog antibody and acceptor, mimetic enzyme catalysis, the isolation and purification of the biomacromolecule such as amino acid and polypeptide metal ion, drug molecule, natural product etc.
The preparation method of current glabridin molecularly imprinted polymer has no report, and glabridin molecular imprinting also has no report for extraction purification.
Summary of the invention
The object of the invention is to fill up technological gap, a kind of glabridin molecularly imprinted polymer and its preparation method and application, the method is simple to operate, and the polymkeric substance alternative absorption glabridin of preparation, has the advantages such as selectivity is strong, adsorptive capacity is large, renewable.
The technical scheme that the present invention takes is:
A preparation method for glabridin molecularly imprinted polymer, comprises step as follows:
(1) take glabridin as template, with acrylamide, methacrylic acid, 4-vinylpridine, vinyl imidazole, N-phenyl methyl acrylate chloride or thanomin carboxylate (NOBE) for function monomer, be that 1 ~ 3:2 ~ 8:15 ~ 30:0.05 ~ 0.2:20 ~ 50 add in reactor and mix in mass ratio by template, function monomer, linking agent, initiator, solvent, ultrasonic degas 5 ~ 25min, then nitrogen deoxygenation is filled, in 40 ~ 60 DEG C of water bath with thermostatic control polymerizations 10 ~ 24 hours after sealing, obtain the molecularly imprinted polymer with template molecule glabridin;
(2) polymer abrasive that step (1) obtains is crossed 60 ~ 200 mesh sieves, obtain evenly with the molecularly imprinted polymer particle of template molecule glabridin, with the molecularly imprinted polymer particle with template molecule glabridin that the acetic acid methanol eluant solution that volume fraction is 10% ~ 20% obtains, under vacuum, 50 ~ 65 DEG C of oven dry, namely obtain the molecularly imprinted polymer for glabridin of purifying.
Function monomer preferable methyl vinylformic acid described in above-mentioned steps (1).
Linking agent described in step (1) is N, N-dimethyl diacrylamine, Ethylene glycol dimethacrylate or Vinylstyrene.Described initiator is Diisopropyl azodicarboxylate.Described solvent is selected from acetonitrile/chloroform (v/v=1:1 ~ 3), N, dinethylformamide/chloroform (v/v=1:1 ~ 2), methyl-sulphoxide/chloroform (v/v=1:1 ~ 2.5), tetrahydrofuran (THF)/chloroform (v/v=1:1 ~ 3), preferred acetonitrile/chloroform (v/v=1).
The glabridin molecularly imprinted polymer that above-mentioned preparation method obtains.
Described glabridin molecularly imprinted polymer is extracting the application in glabridin from glycyrrhiza glabra.
Application method is: preparation-obtained glabridin molecularly imprinted polymer is done column chromatography filler dress post, then fruit licorice extract upper prop is used up, use the acetonitrile solution drip washing of the methyl alcohol of volume fraction 5% ~ 15% again, the acetic acid methanol eluant solution of last chromatography column mass concentration 10% ~ 20%, reclaims elutriant and obtains glabridin.
The present invention uses glabridin as template in the molecularly imprinted polymer building-up process of purification glabridin, molecular imprinting is utilized to make identification material to measure for glabridin, elute glabridin template, material leaves and the hole of glabridin molecular volume, structure, matched polarity (or being called trace).This molecularly imprinted polymer for purify glabridin time, only have glabridin molecule can enter in the middle of trace, and other impurity molecule can not enter trace, make this molecularly imprinted polymer primary attachment glabridin, other impurity absorption little, the purity of glabridin is improved greatly, can 90% be reached.
The present invention is not limited to certain simple function monomer (as 4-vinylpridine) preparing in glabridin molecularly imprinted polymer process, to the several functions monomer selected, adopts preparation method of the present invention, all can obtain the good molecularly imprinted polymer of identity.In preparation technology, the present invention adopts traditional mass polymerization, and comparatively additive method (as suspension polymerization, dispersion polymerization) has better technology stability and controllability.
The present invention has following advantage and beneficial effect relative to prior art:
1. the molecularly imprinted polymer selectivity for glabridin of purifying of the present invention is strong, applies the glabridin purity that this material purification glabridin obtains high.
2. the molecularly imprinted polymer adsorptive capacity for glabridin of purifying of the present invention is large, is 4 ~ 10 times of conventional resins.
3. the molecularly imprinted polymer production cost for glabridin of purifying of the present invention is low, and elutriant consumption is few.
4. present device less investment, production cost reduces greatly.
5. the molecularly imprinted polymer for glabridin of purifying of the present invention is renewable after being applied to glabridin of purifying from glycyrrhiza glabra crude extract, and its renovation process is simple.
Accompanying drawing explanation
Fig. 1 is the schema of the Synthesis and applications of the molecularly imprinted polymer for glabridin of purifying of the present invention.
Fig. 2 is the molecular structural formula of function monomer NOBE used in the present invention.
Fig. 3 is that the application molecularly imprinted polymer for glabridin of purifying of the present invention is purified the purity detecting figure of the glabridin obtained, and its content is 90.10g/100g.
Fig. 4 is the glabridin proton nmr spectra that application the present invention extracts.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but working of an invention mode is not limited thereto.
Embodiment 1
(1) get the raw materials ready
The each component of the present embodiment is by following consumption proportion batching: template molecule (glabridin) 0.97g, function monomer (methacrylic acid) 1.63g, linking agent (Ethylene glycol dimethacrylate) 19.00g, initiator (Diisopropyl azodicarboxylate) 0.10g, solvent (weight ratio of acetonitrile and chloroform is the mixed solvent of 1:1) 42.00g.
(2) preparation is with the molecularly imprinted polymer of template molecule glabridin
The template molecule glabridin got ready in (1), methacrylic acid, Ethylene glycol dimethacrylate, Diisopropyl azodicarboxylate, acetonitrile are added in reactor with the mixed solvent of chloroform and mixes, ultrasonic degas 15min, then nitrogen deoxygenation is filled, 24 hours are polymerized in 60 DEG C of waters bath with thermostatic control after sealing, obtain the molecularly imprinted polymer with template molecule glabridin, then by its milled 60 orders and 100 mesh sieves, the molecularly imprinted polymer particle of 60 ~ 100 orders with template molecule glabridin is namely obtained.
(3) purify with the molecularly imprinted polymer of template molecule glabridin
Be the molecularly imprinted polymer particle with template molecule glabridin of 10% methanol solution wash-out obtained by (2) by acetic acid volume fraction, after 60 DEG C of vacuum-drying, namely obtain the described molecularly imprinted polymer 18.4g for glabridin of purifying.
(4) dress of the molecularly imprinted polymer for glabridin of the purifying post obtained by 15 grams of steps (2) is got.Taking 300g glycyrrhiza glabra to pulverize, add 4L95%(v/v) alcohol heating reflux extracts after 2h, filters, filtrate evaporate to dryness, upper prop after 1L chloroform redissolves.After upper prop solution flows to end, drip washing is carried out with the acetonitrile solution 300 milliliters that methyl alcohol volume fraction is 5%, chromatography column acetic acid volume fraction is 10% methanol solution wash-out, collect elutriant, namely obtain high-purity glabrene after evaporate to dryness, its purity is 90.10g/100g (see accompanying drawing 3) after testing.
1H NMR(DMSO-d
6,600MHz):δ9.39(s,1H),9.11(s,1H),6.86(d,1H,J=7.8Hz),6.83(d,1H,J=8.4Hz),6.54(d,1H,J=9.6Hz),6.33(s,1H),6.29(d,1H,J=8.4Hz),6.19(d,1H,J=8.4Hz),5.64(d,1H,J=10.2Hz),4.23(d,1H,J=10.2Hz),3.93(t,1H,J=10.2Hz),3.29(t,1H,J=10.2Hz),2.89(dd appeared t,1H,J=11.4Hz),2.69(dd,1H,J=16.2and4.2Hz),1.76(s,6H)
(5) regeneration of molecularly imprinted polymer
By the above-mentioned molecularly imprinted polymer washing away glabridin, use 95% ethanol elution, namely renewable for extracting use next time.
Embodiment 2
(1) get the raw materials ready
The each component of the present embodiment is by following consumption proportion batching: template molecule (glabridin) 0.97g, function monomer (4-vinylpridine) 1.83g, linking agent (N, N-dimethyl diacrylamine) 21.00g, initiator (Diisopropyl azodicarboxylate) 0.16g, solvent (weight ratio of DMF and chloroform is the mixed solvent of 2:1) 45.00g.
(2) preparation is with the molecularly imprinted polymer of template molecule glabridin
By the template molecule glabridin, 4-vinylpridine, the N that get ready in (1), N-dimethyl diacrylamine, Diisopropyl azodicarboxylate and N, the mixed solvent of dinethylformamide and chloroform adds in reactor and mixes, ultrasonic degas 15min, then nitrogen deoxygenation is filled, 24 hours are polymerized in 60 DEG C of waters bath with thermostatic control after sealing, obtain the molecularly imprinted polymer with template molecule glabridin, then by its milled 100 orders and 150 mesh sieves, the molecularly imprinted polymer particle of 100 ~ 150 orders with template molecule glabridin is namely obtained.
(3) purify with the molecularly imprinted polymer of template molecule glabridin
Be the molecularly imprinted polymer particle with template molecule glabridin of 10% methanol solution wash-out obtained by (2) by acetic acid volume fraction, after 60 DEG C of vacuum-drying, namely obtain the described molecularly imprinted polymer 20.1g for glabridin of purifying.
(4) dress of the molecularly imprinted polymer for glabridin of the purifying post obtained by 15 grams of steps (2) is got.Taking 300g glycyrrhiza glabra to pulverize, add 4L95%(v/v) alcohol heating reflux extracts after 2h, filters, filtrate evaporate to dryness, upper prop after 1L chloroform redissolves.After upper prop solution flows to end, carry out drip washing with the acetonitrile solution 300 milliliters that methyl alcohol volume fraction is 5%, chromatography column acetic acid volume fraction is 10% methanol solution wash-out, and collect elutriant, namely obtain glabridin after evaporate to dryness, its purity is 89.25g/100g after testing.
(5) regeneration of molecularly imprinted polymer
By the above-mentioned molecularly imprinted polymer washing away glabridin, use 95% ethanol elution, namely renewable for extracting use next time.
Embodiment 3
(1) get the raw materials ready
The each component of the present embodiment is by following consumption proportion batching: template molecule (glabridin) 0.97g, function monomer (vinyl imidazole) 1.60g, linking agent (Ethylene glycol dimethacrylate) 21.00g, initiator (benzoyl peroxide) 0.16g, solvent (weight ratio of tetrahydrofuran (THF) and chloroform is the mixed solvent of 2:1) 42.00g.
(2) preparation is with the molecularly imprinted polymer of template molecule glabridin
The mixed solvent of template molecule glabridin, vinyl imidazole, Ethylene glycol dimethacrylate, Diisopropyl azodicarboxylate, tetrahydrofuran (THF) and the chloroform got ready in (1) is added in reactor and mixes, ultrasonic degas 15min, then nitrogen deoxygenation is filled, 24 hours are polymerized in 60 DEG C of waters bath with thermostatic control after sealing, obtain the molecularly imprinted polymer with template molecule glabridin, then by its milled 100 orders and 150 mesh sieves, the molecularly imprinted polymer particle of 100 ~ 150 orders with template molecule glabridin is namely obtained.
(3) purify with the molecularly imprinted polymer of template molecule glabridin
Be the molecularly imprinted polymer particle with template molecule glabridin of 10% methanol solution wash-out obtained by (2) by acetic acid volume fraction, after 60 DEG C of vacuum-drying, namely obtain the described molecularly imprinted polymer 19.8g for glabridin of purifying.
(4) dress of the molecularly imprinted polymer for glabridin of the purifying post obtained by 15 grams of steps (2) is got.Take 300g glycyrrhiza glabra to pulverize, after adding 4L95% ethanol (v/v) heating and refluxing extraction 2h, filter, filtrate evaporate to dryness, upper prop after 1L chloroform redissolves.After upper prop solution flows to end, carry out drip washing with the acetonitrile solution 300 milliliters that methyl alcohol volume fraction is 5%, chromatography column acetic acid volume fraction is 10% methanol solution wash-out, and collect elutriant, namely obtain glabridin after evaporate to dryness, its purity is 85.28g/100g after testing.。
(5) regeneration of molecularly imprinted polymer
By the above-mentioned molecularly imprinted polymer washing away glabridin, use 95% ethanol elution, namely renewable for extracting use next time.
Embodiment 4
The function monomer that the present embodiment uses is acrylamide, linking agent is N, N-dimethyl diacrylamine, solvent is the weight ratio of methyl-sulphoxide and chloroform is the mixed solvent of 1:1, initiator is Diisopropyl azodicarboxylate, other is all identical with embodiment 1, gained glabridin, and its purity is 85.60g/100g after testing.
Embodiment 5
The function monomer that the present embodiment uses is N-phenyl methyl acrylate chloride, linking agent is Ethylene glycol dimethacrylate, solvent is the weight ratio of tetrahydrofuran (THF) and chloroform is the mixed solvent of 2:1, initiator is Diisopropyl azodicarboxylate, other is all identical with embodiment 1, gained glabridin, its purity is 75.35g/100g after testing.
Embodiment 6
The function monomer that the present embodiment uses is NOBE, and linking agent is Vinylstyrene, and solvent is the mixed solvent of the weight ratio 1:1 of methyl-sulphoxide and chloroform, initiator is Diisopropyl azodicarboxylate, other is all identical with embodiment 1, gained glabridin, and its purity is 88.80g/100g after testing.
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from spirit of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (6)
1. a preparation method for glabridin molecularly imprinted polymer, is characterized in that, comprises step as follows:
(1) take glabridin as template, with acrylamide, methacrylic acid, 4-vinylpridine, vinyl imidazole, N-phenyl methyl acrylate chloride or thanomin carboxylate (NOBE) for function monomer, be that 1 ~ 3:2 ~ 8:15 ~ 30:0.05 ~ 0.2:20 ~ 50 add in reactor and mix in mass ratio by template, function monomer, linking agent, initiator, solvent, ultrasonic degas 5 ~ 25min, then nitrogen deoxygenation is filled, in 40 ~ 60 DEG C of water bath with thermostatic control polymerizations 10 ~ 24 hours after sealing, obtain the molecularly imprinted polymer with template molecule glabridin; Described linking agent is N, N-dimethyl diacrylamine, Ethylene glycol dimethacrylate or Vinylstyrene; Described solvent is acetonitrile/chloroform, v/v=1:1;
(2) polymer abrasive that step (1) obtains is crossed 60 ~ 200 mesh sieves, obtain evenly with the molecularly imprinted polymer particle of template molecule glabridin, with the molecularly imprinted polymer particle with template molecule glabridin that the acetic acid methanol eluant solution that volume fraction is 10% ~ 20% obtains, under vacuum, 50 ~ 65 DEG C of oven dry, namely obtain the molecularly imprinted polymer for glabridin of purifying.
2. according to the preparation method of a kind of glabridin molecularly imprinted polymer described in claim 1, it is characterized in that, the function monomer described in step (1) is methacrylic acid.
3. according to the preparation method of a kind of glabridin molecularly imprinted polymer described in claim 1, it is characterized in that, described initiator is Diisopropyl azodicarboxylate.
4. the glabridin molecularly imprinted polymer that the preparation method described in any one of claim 1-3 obtains.
5. the glabridin molecularly imprinted polymer described in claim 4 is extracting the application in glabridin from glycyrrhiza glabra.
6. the application as described in claim 5, it is characterized in that, described application method is: the glabridin molecularly imprinted polymer obtained is done column chromatography filler dress post, then fruit licorice extract upper prop is used up, use the acetonitrile solution drip washing of the methyl alcohol of volume fraction 5% ~ 15% again, the methanol solution wash-out of the acetic acid of last chromatography column volume fraction 10% ~ 20%, reclaims elutriant and obtains glabridin.
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