CN110117342A - A kind of benzyl carbinol glycoside molecularly imprinted polymer and its preparation method and application - Google Patents
A kind of benzyl carbinol glycoside molecularly imprinted polymer and its preparation method and application Download PDFInfo
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- CN110117342A CN110117342A CN201910299049.4A CN201910299049A CN110117342A CN 110117342 A CN110117342 A CN 110117342A CN 201910299049 A CN201910299049 A CN 201910299049A CN 110117342 A CN110117342 A CN 110117342A
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- benzyl carbinol
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/268—Polymers created by use of a template, e.g. molecularly imprinted polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/042—Elimination of an organic solid phase
- C08J2201/0422—Elimination of an organic solid phase containing oxygen atoms, e.g. saccharose
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2335/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
- C08J2335/02—Characterised by the use of homopolymers or copolymers of esters
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Abstract
The invention discloses a kind of preparation methods of benzyl carbinol glycoside molecularly imprinted polymer, it is characterized in that, include the following steps: that (1) 1:8~1:30 is added in solvent in molar ratio by benzyl carbinol glycoside template molecule, function monomer, carries out prepolymerization, obtains prepolymerization liquid after mixing；(2) for the prepolymerization liquid for obtaining step (1) with after crosslinking agent, initiator mixing deoxygenation, heating carries out polymerization reaction, obtains polymer, and the molar ratio of the function monomer in step (1) and the crosslinking agent is 1:3；(3) polymer that step (2) obtains is ground and is sieved, collected the part that granularity is 45~100 μm, eluted with eluent, obtain benzyl carbinol glycoside molecularly imprinted polymer；And polymer and application according to this method preparation.This have the advantages that efficiently, preparation process it is simple, benzyl carbinol glycoside substance process is easy to operate for isolating and purifying in Cistanche tubulosa for gained benzyl carbinol glycoside molecularly imprinted polymer, and low energy consumption.
Description
Technical field
The invention belongs to natural materials separating and purifying technology fields, and in particular to a kind of benzyl carbinol glycoside molecular engram polymerization
Object and its preparation method and application.
Background technique
Cistanche tubulosa be Orobanchaceae Herba Cistanches plant, be rare one of help Chinese herbal medicine, be known as " desert ginseng " and
The good reputation of " treasure in medicine ".Cistanche tubulosa main product is a kind of desert parasitic plant, host red building, sacsaoul in Xinjiang South Sinkiang
There is unique effect in terms of checking winds and fixing drifting sand with environmental protection, and artificial cultivation is easier to.Studies have shown that cultivation and wild pipe
The content of active constituent benzyl carbinol glycosides is almost the same in flower herba cistanches.Studies have shown that benzyl carbinol glycosides have protection liver, antioxygen
Change, anti-aging, adjusting nerve cell, strengthen immunity, raising memory and other effects.
The isolation and purification method of existing natural products active principle specifically includes that molecular imprinting technology, Amberlyst process
With membrane separation process etc..Wherein, molecular imprinting technology is a kind of efficient molecular recognition technology, it can be prepared in compatible degree and ruler
Very little size and template compound fit like a glove, the molecularly imprinted polymer with specific recognition performance.Molecular imprinting technology has
Selectivity is high, molecularly imprinted polymer is reusable, high-efficient, easy to operate, be separating natural product active principle more
One of ideal method.
Summary of the invention
The first purpose of this invention is to provide for a kind of preparation method of benzyl carbinol glycoside molecularly imprinted polymer.
A second object of the present invention is to provide according to polymer obtained by the above method.
Third object of the present invention is to provide the purposes of above-mentioned polymer.
The purpose of the present invention is achieved by the following technical scheme:
A kind of preparation method of benzyl carbinol glycoside molecularly imprinted polymer, includes the following steps:
(1) by benzyl carbinol glycoside template molecule, function monomer, 1:8~1:30 is added in solvent in molar ratio, is mixed laggard
Row prepolymerization obtains prepolymerization liquid；
(2) with after crosslinking agent, initiator mixing deoxygenation, heating is polymerize the prepolymerization liquid for obtaining step (1)
Reaction, obtains polymer, and the molar ratio of the function monomer in step (1) and the crosslinking agent is 1:3；
(3) polymer that step (2) obtains is ground and is sieved, collected the part that granularity is 45~100 μm, use eluent
It is eluted, obtains benzyl carbinol glycoside molecularly imprinted polymer.
Further, in step (1), the benzyl carbinol glycoside template molecule be echinacoside or acteoside, it is described
Function monomer is 4-vinylpridine or methacrylic acid；The solvent is methanol or the acetonitrile of volume ratio 1:1.5: DMF；
The prepolymerization carries out under conditions of 25 DEG C, 150rpm, prepolymerization time 30min.
Further, in step (2), the crosslinking agent is ethylene glycol dimethacrylate, and the initiator is azo
Bis-isobutyronitrile；
The temperature of the polymerization reaction is 60~68 DEG C, and the time is for 24 hours.
Further, in step (3), the eluent is the methanol of volume ratio 9:1: acetic acid.
The benzyl carbinol glycoside molecularly imprinted polymer obtained according to any of the above-described method.
Above-mentioned benzyl carbinol glycoside molecularly imprinted polymer is used to isolate and purify the benzyl carbinol glycosides in Cistanche tubulosa.
The invention has the following advantages:
The preparation method of benzyl carbinol glycoside molecularly imprinted polymer provided by the invention, with efficient, preparation process is simple
The advantages of, gained benzyl carbinol glycoside molecularly imprinted polymer is for isolating and purifying benzyl carbinol glycoside substance process in Cistanche tubulosa
Easy to operate, low energy consumption, efficiently separates for benzyl carbinol glycoside in active ingredient of natural product and provides new method.
Detailed description of the invention
Fig. 1 is the infrared figure of molecularly imprinted polymer obtained by the embodiment of the present invention 1.
Fig. 2 is the infrared figure of molecularly imprinted polymer obtained by the embodiment of the present invention 2.
Fig. 3 is the infrared figure of molecularly imprinted polymer obtained by the embodiment of the present invention 3.
Fig. 4 is the infrared figure of molecularly imprinted polymer obtained by the embodiment of the present invention 4.
Specific embodiment
Hereinafter, preferred embodiments of the present invention will be described, it should be understood that preferred embodiment described herein is only used
In the description and interpretation present invention, it is not intended to limit the present invention.
Each raw material of the embodiment of the present invention is that market can obtain product, wherein acteoside producer: the auspicious chemical industry of ancient cooking vessel (on
Sea) Co., Ltd, purity >=98%.
The preparation method of Cistanche tubulosa extracting solution: the ethanol water of 50vt% is added in Cistanche tubulosa powder, adds
For heat to 70 DEG C, powder and ethanol mass volume ratio are 1:9 (g/ml), are extracted at 70 DEG C using high shear homogeneous emulsifying machine
2min is extracted 1 time, and it is 16000rpm that revolving speed is extracted in high shear, is stood, is taken supernatant liquor, obtain Cistanche tubulosa extracting solution, Mao Rui
The purity of flower glucosides is 1.8%.
Embodiment 1
Prepare benzyl carbinol glycoside molecularly imprinted polymer: using acteoside as template molecule, 4-vinylpridine is function
Energy monomer, acetonitrile: DMF (1:1.5, v/v) is solvent, and ethylene glycol dimethacrylate is crosslinking agent, and azodiisobutyronitrile is
Initiator.125mg (0.2mmol) acteoside is accurately weighed, 210mg (2mmol) 4-vinylpridine is placed in 50mL round bottom
In flask, 1mL acetonitrile and 1.5mL DMF is added, is put into constant temperature oscillator, 150rpm, 25 DEG C of oscillation 20min carry out prepolymerization
Afterwards, it takes out and 1189mg (6mmol) ethylene glycol dimethacrylate and 15mg azodiisobutyronitrile is added, filled using ATRP device
Enter nitrogen and remove oxygen, is put into 60 DEG C of constant temperature oil baths and polymerize for 24 hours.Polymer is taken out from round-bottomed flask, is ground, sieving,
Collect the part that granularity is 45~100 μm, reuse methanol: acetic acid (9:1, v/v) is used as eluent ultrasound eluted template molecule,
Obtain benzyl carbinol glycoside molecularly imprinted polymer.
Static Adsorption and desorption of the benzyl carbinol glycoside molecularly imprinted polymer to Cistanche tubulosa extracting solution: 100mg is weighed
Extracting solution is added in 50mL conical flask in molecularly imprinted polymer, and sealing is placed on 200rpm shaking table, will after 60 DEG C of concussion 12h
It adsorbs sufficient molecularly imprinted polymer to be cleaned with 90vt% ethyl alcohol, washes and be placed in 50mL conical flask, eluent is added
50vt% ethanol elution 12h.The content of acteoside after purification is measured using HPLC.The absorption of acteoside after purification
Amount reaches 64.1mg/g, and the rate of recovery is up to 90.1%, and purity is up to 27.9%.
Embodiment 2
Prepare benzyl carbinol glycoside molecularly imprinted polymer, with embodiment 1 except that: acteoside dosage is
156mg (0.25mmol), methacrylic acid are function monomer, and dosage is 172mg (2mmol).
Static Adsorption and desorption of the benzyl carbinol glycoside molecularly imprinted polymer to Cistanche tubulosa extracting solution: 100mg is weighed
Extracting solution is added in 50mL conical flask in molecularly imprinted polymer, and sealing is placed on 200rpm shaking table, will after 60 DEG C of concussion 12h
It adsorbs sufficient molecularly imprinted polymer to be cleaned with 90vt% ethyl alcohol, washes and be placed in 50mL conical flask, eluent is added
50vt% ethanol elution 12h.The content of acteoside after purification is measured using HPLC.The absorption of acteoside after purification
Amount reaches 30.8mg/g, and the rate of recovery is up to 92.1%, and purity is up to 20.9%.
Embodiment 3
Prepare benzyl carbinol glycoside molecularly imprinted polymer, with embodiment 1 except that: acteoside dosage be 42mg
(0.067mmol), solvent are methanol.
Static Adsorption and desorption of the benzyl carbinol glycoside molecularly imprinted polymer to Cistanche tubulosa extracting solution: 100mg is weighed
Extracting solution is added in 50mL conical flask in molecularly imprinted polymer, and sealing is placed on 200rpm shaking table, will after 60 DEG C of concussion 12h
It adsorbs sufficient molecularly imprinted polymer to be cleaned with 90vt% ethyl alcohol, washes and be placed in 50mL conical flask, eluent is added
50vt% ethanol elution 12h.The content of acteoside after purification is measured using HPLC.The absorption of acteoside after purification
Amount reaches 17.2mg/g, and the rate of recovery is up to 88.9%, and purity is up to 18.9%.
Embodiment 4
Prepare benzyl carbinol glycoside molecularly imprinted polymer, with embodiment 1 except that: methacrylic acid be function list
Body, dosage are 172mg (2mmol), and solvent is methanol.
Static Adsorption and desorption of the benzyl carbinol glycoside molecularly imprinted polymer to Cistanche tubulosa extracting solution: 100mg is weighed
Extracting solution is added in 50mL conical flask in molecularly imprinted polymer, and sealing is placed on 200rpm shaking table, will after 60 DEG C of concussion 12h
It adsorbs sufficient molecularly imprinted polymer to be cleaned with 90% ethyl alcohol, washes and be placed in 50mL conical flask, eluent is added
50% ethanol elution 12h.The content of acteoside after purification is measured using HPLC.The adsorbance of acteoside after purification
Up to 55.1mg/g, the rate of recovery is up to 92.1%, and purity is up to 20.7%.
Comparative example 1
Prepare Cistanche tubulosa extracting solution.100mg HPD300 macroreticular resin is weighed in 50mL conical flask, is added and extracts
Liquid, sealing are placed on 200rpm shaking table, and 60 DEG C of concussions will adsorb sufficient HPD300 macroreticular resin afterwards for 24 hours and be placed in 50mL conical flask
In, addition eluent, which is placed on 200rpm shaking table, to be desorbed.Using acteoside after HPLC measurement HPD300 macroporous resin purification
Content.The adsorbance of acteoside reaches 30.6mg/g, and desorption efficiency is up to 98.6%, and purity is up to 10.8%.
The molecularly imprinted polymer specific surface area that the embodiment of the present invention obtains reaches 191.3m2/ g, aperture are 3.6~3.9nm.
The molecularly imprinted polymer of embodiment 1 is applied to acteoside in separation Cistanche tubulosa, acteoside after purification
Adsorbance reaches 64.1mg/g, and for the rate of recovery up to 90.1%, purity is increased to 27.9% by 1.8% before purification.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, although referring to aforementioned reality
Applying example, invention is explained in detail, for those skilled in the art, still can be to aforementioned each implementation
Technical solution documented by example is modified or equivalent replacement of some of the technical features.It is all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (6)
1. a kind of preparation method of benzyl carbinol glycoside molecularly imprinted polymer, which comprises the steps of:
(1) by benzyl carbinol glycoside template molecule, function monomer, 1:8~1:30 is added in solvent in molar ratio, is carried out after mixing pre-
Polymerization, obtains prepolymerization liquid；
(2) for the prepolymerization liquid for obtaining step (1) with after crosslinking agent, initiator mixing deoxygenation, heating carries out polymerization reaction,
Polymer is obtained, the molar ratio of the function monomer in step (1) and the crosslinking agent is 1:3；
(3) polymer that step (2) obtains is ground and is sieved, collected the part that granularity is 45~100 μm, carried out with eluent
Elution, obtains benzyl carbinol glycoside molecularly imprinted polymer.
2. the preparation method of benzyl carbinol glycoside molecularly imprinted polymer according to claim 1, which is characterized in that step
(1) in, the benzyl carbinol glycoside template molecule is echinacoside or acteoside, and the function monomer is 4-vinylpridine
Or methacrylic acid；The solvent is methanol or the acetonitrile of volume ratio 1:1.5: DMF；
The prepolymerization carries out under conditions of 25 DEG C, 150rpm, prepolymerization time 30min.
3. the preparation method of benzyl carbinol glycoside molecularly imprinted polymer according to claim 1, which is characterized in that step
(2) in, the crosslinking agent is ethylene glycol dimethacrylate, and the initiator is azodiisobutyronitrile；
The temperature of the polymerization reaction is 60~68 DEG C, and the time is for 24 hours.
4. the preparation method of benzyl carbinol glycoside molecularly imprinted polymer according to claim 1, which is characterized in that step
(3) in, the eluent is the methanol of volume ratio 9:1: acetic acid.
5. the benzyl carbinol glycoside molecularly imprinted polymer obtained according to claim 1-4 either method.
6. benzyl carbinol glycoside molecularly imprinted polymer described in claim 5 is used to isolate and purify the benzyl carbinol in Cistanche tubulosa
Glycosides.
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Cited By (3)
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| CN110862568A (en) * | 2019-12-04 | 2020-03-06 | 石河子大学 | Preparation method and application of molecularly imprinted membrane for separating phenylethanoid glycosides |
| CN112619435A (en) * | 2020-12-02 | 2021-04-09 | 石河子大学 | Preparation method of molecularly imprinted hybrid membrane for separating phenylethanoid glycosides |
| WO2023006895A1 (en) * | 2021-07-30 | 2023-02-02 | Ecole Superieure De Physique Et De Chimie Industrielles De La Ville De Paris | Molecular imprinted polymer and use thereof in quantifying a pesticide in a sample |
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| CN110862568A (en) * | 2019-12-04 | 2020-03-06 | 石河子大学 | Preparation method and application of molecularly imprinted membrane for separating phenylethanoid glycosides |
| CN112619435A (en) * | 2020-12-02 | 2021-04-09 | 石河子大学 | Preparation method of molecularly imprinted hybrid membrane for separating phenylethanoid glycosides |
| WO2023006895A1 (en) * | 2021-07-30 | 2023-02-02 | Ecole Superieure De Physique Et De Chimie Industrielles De La Ville De Paris | Molecular imprinted polymer and use thereof in quantifying a pesticide in a sample |
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