CN110801820A - Preparation method and application of iridoid multi-component imprinted composite material - Google Patents
Preparation method and application of iridoid multi-component imprinted composite material Download PDFInfo
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- CN110801820A CN110801820A CN201911165691.XA CN201911165691A CN110801820A CN 110801820 A CN110801820 A CN 110801820A CN 201911165691 A CN201911165691 A CN 201911165691A CN 110801820 A CN110801820 A CN 110801820A
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- 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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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
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Abstract
The invention discloses a preparation method of iridoid multicomponent simultaneous imprinting composite material microspheres and a solid phase extraction method applied to blood pressure reducing active compounds in eucommia crude extracts. According to the invention, a sulfonic group modified metal organic framework is used as a carrier, and multi-component iridoid compounds, namely pinoresinol diglucoside, aucubin and geniposide, are used as a common template to prepare the imprinted composite material microsphere with the particle size of 20-50 microns.
Description
Technical Field
The invention belongs to the field of new materials, and particularly relates to a preparation method of a novel imprinted microsphere with high selective adsorption capacity on eucommia ulmoides iridoid multicomponent compounds, and solid-phase extraction separation and purification.
Background
Eucommia bark is a famous and precious Chinese medicinal material, has biological activities such as blood pressure reduction and the like, wherein iridoid compounds such as pinoresinol diglucoside and the like are typical blood pressure reduction biomasses, and meanwhile, the compounds also have the effects of increasing cerebral blood flow, improving immunity, improving learning and memory, resisting tumors, reducing blood sugar, relieving alcoholism and the like, and are very wide in clinical application. Extraction and separation from eucommia ulmoides plants are the main approaches for obtaining iridoid compounds. However, some existing extraction technologies have low selectivity to target compounds, which often makes the extraction process very complicated and the extraction cost is high. The research on the enrichment material with high selectivity to the compounds and the separation method has very important significance for realizing the high-efficiency extraction of the plant bioactive compounds.
The molecular imprinting technology is a technology that chemists synthesize molecular imprinting polymers by using some natural compounds as templates and perform molecular recognition. The basic principle of the polymer which is synthesized by the molecular imprinting technology and has the specificity recognition and the selective adsorption is a theory formed by simulating the process of the specificity recognition of an antigen and an antibody in an organism and synthesizing the antibody by taking the antigen as a template. The template molecule and the functional monomer are subjected to polymerization reaction under the action of a cross-linking agent and an initiator, and the template molecule is eluted by some means to obtain the polymer with a specific hole similar to the structure of the template molecule. The molecularly imprinted polymer has higher specific recognition and selective adsorption capacity on target molecules, is widely applied to the fields of solid phase extraction, adsorption, catalysis and the like, and has the main characteristics that: (1) the selectivity is predetermined. The molecularly imprinted polymer MIPs can be prepared according to different target compounds, has wide adaptability and can meet various different requirements; 2. high selective recognition. The molecular engram polymer is tailored according to the size, shape and chemical functional group of the template molecule, so that the engram molecule can be specifically identified; 3. the molecular imprinting polymer has wide practicability, the selective recognition capability of the molecular imprinting polymer can be compared with that of a natural biological molecular recognition system, such as enzyme and substrate, antigen and antibody, and receptor and hormone, but has the capability of resisting severe environments, such as high temperature, acid and alkali, and the like, which are not possessed by the natural molecular recognition system, so that the molecular imprinting polymer has high stability and long service life. The molecularly imprinted polymer obtained by the conventional imprinting technology has a great limitation in application because the molecular recognition and mass transfer process is slow due to the deep burial of the binding sites therein. The surface imprinting technology can effectively solve the problem of deeper burying of the binding sites. In the surface imprinting technology, a carrier is firstly subjected to surface modification to obtain a functional group capable of bonding a compound, and then the surface imprinted polymer is prepared through surface grafting.
As a high-efficiency carrier, a Metal Organic Framework (MOFS) is a novel porous material, has the characteristics of ultra-large specific surface area, ultra-high and adjustable porosity and the like, and is widely used in the fields of gas storage, adsorption separation, catalysis and the like. Among them, the metal organic framework material is used for chromatographic fixation as a current research focus, but the research for preparing the imprinted polymer by using the metal organic framework material as a carrier is less. The advantages of the metal organic framework material and the molecularly imprinted polymer can be fully exerted by combining the high adsorption effect of the metal organic framework material and the high selectivity of the molecularly imprinted polymer, the high-selectivity and high-capacity adsorption requirement of the novel imprinted material on a target compound is greatly improved, and high technical requirements are provided for the separation and purification of plant bioactive compounds and the industrial development of medicinal components.
Disclosure of Invention
In order to overcome the defects of the prior art, the method takes a metal organic framework subjected to surface sulfonylation modification as a carrier, takes a multi-component iridoid compound as a composite template molecule, and adopts a surface imprinting and precipitation polymerization composite technology to prepare the iridoid multi-component imprinting composite material microsphere.
In order to obtain the molecularly imprinted composite material microspheres, the invention adopts the following process steps:
(1) preparing MIL-101 and carrying out sulfonylation modification: adding 1.0mmol of chromium nitrate nonahydrate and 1.0-3.0mmol of terephthalic acid into 50mL of deionized water, adding 0.2-0.5mL of hydrofluoric acid, ultrasonically stirring, uniformly mixing, pouring the mixed solution into a 100mL hydrothermal reaction kettle, and sealingSealing and reacting for 10-12 hours at the temperature of 493K, cooling, performing suction filtration, sequentially washing solids with deionized water and N, N-Dimethylformamide (DMF), transferring the solids to a reaction kettle, adding 50mL of ethanol, reacting for 16-20 hours at the temperature of 373K, filtering, repeatedly washing with ethanol, performing vacuum drying, and grinding and sieving to obtain green solid powder MIL-101 (A); 4.0g of MIL-101 was charged into a 250mL flask, and 100mL of CH was added3NO2After stirring evenly, adding 5.0 mmol of concentrated sulfuric acid and 5.0-10.0mmol of trifluromethyl glycoside, reacting for 6-10 hours at the temperature of 308K, filtering, repeatedly washing the solid for 3 times by using 50mL of absolute ethyl alcohol and deionized water in sequence, and drying in vacuum to obtain the solid B.
(2) Preparing an iridoid multi-component simultaneous imprinting composite material: weighing 0.4-0.6g of the solid B, adding the solid B into 30-45mL of acetonitrile-dimethyl sulfoxide-methanol (volume ratio is 2:2: 1) mixed solvent, adding 0.6-1.0mmol of geniposide-aucubin-pinoresinol diglucoside (molar ratio is 1:1: 1) mixture, 6.0-10mmol of divinylbenzene and 25.0mg of azobisisobutyronitrile, ultrasonically mixing for 5min, introducing argon for 15min, sealing the reaction container, placing the reaction container in 333K oil bath, controlling the rotating speed of the reaction vessel to be 10-20r/min, pouring the reaction mixture into 50.0mL of methanol solution after reacting for 12 hours, and (3) settling for 4h, sucking out the upper-layer liquid, then repeatedly settling for two times by using 50.0mL of water and acetonitrile respectively, 4h each time, sucking out the upper-layer liquid, filtering, and vacuum-drying the solid at 60 ℃ for 12h to obtain the imprinted composite material microspheres with the particle size of 20-50 microns.
The molecular imprinting composite material microsphere has high selective adsorption capacity on blood pressure reducing compounds in the eucommia seed meal methanol extract, such as pinoresinol diglucoside, aucubin, geniposide and the like, can be used for selective adsorption and solid phase extraction separation and purification of certain blood pressure reducing active compounds in eucommia, and has good application efficiency.
The molecular imprinted polymer obtained by the invention is used as an adsorbent, and has the characteristic of simple extraction and separation process when the antihypertensive compound in the eucommia ulmoides crude extract is extracted, separated and purified in a solid phase, the target compound with higher purity can be obtained by single-step operation, the product recovery rate is high, and the imprinted polymer can be repeatedly used.
For example, 1.5 g of molecularly imprinted polymer powder is loaded into a solid phase extractor, 20mL of methanol and 20mL of acetonitrile are used for washing residual compounds and are balanced by acetonitrile, 10-15mL of eucommia ulmoides oliv seed meal methanol extract is injected into the solid phase extractor, and 5-10mL of acetonitrile and 5-10mLH are firstly used2Washing with O as solvent, sequentially adding 5-20 mL of methanol and 5-10mL of 0.002 mol L-1Na2HPO4-NaH2PO4Eluting with buffer solution and 5-10mL of methanol-acetic acid mixed solution (volume ratio of 8: 2), collecting eluates, and freeze drying or distilling under reduced pressure to remove solvent to obtain aucubin with purity of 75.2-80.7%, geniposide with purity of 70.3-85.5%, and pinoresinol diglucoside with purity of 72.6-83.5%.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a preparation method of novel surface imprinted microspheres of multi-component iridoid compounds by taking a sulfonylation modified metal organic framework as a carrier, wherein the imprinted microspheres combine the high specific surface property of a metal organic framework material with the high selectivity of a molecular imprinted material, have high-efficiency separation capacity on target compounds, can be used for extracting and purifying antihypertensive active compounds in plants, can be recycled after recovery treatment, and reduce the production cost.
Detailed Description
The preparation method and application of the iridoid multicomponent imprinted microsphere are explained in detail below.
Example 1:
(1) preparing MIL-101 and carrying out sulfonylation modification: adding 1.0mmol of chromium nitrate nonahydrate and 1.5mmol of terephthalic acid into 50mL of deionized water, adding 0.3mL of hydrofluoric acid, ultrasonically stirring and uniformly mixing, pouring the mixed solution into a 100mL hydrothermal reaction kettle, sealing and reacting at the temperature of 493K for 10.5 hours, cooling and filtering, sequentially washing the solid with deionized water and N, N-Dimethylformamide (DMF), transferring the solid into the reaction kettle, adding 50mL of ethanol, reacting at the temperature of 373K for 17 hours, filtering and repeatedly washing with ethanol, and drying in vacuumGrinding and sieving after drying to obtain green solid powder MIL-101 (A); 4.0g of MIL-101 was charged into a 250mL flask, and 100mL of CH was added3NO2And after stirring uniformly, adding 5.0 mmol of concentrated sulfuric acid and 6.0mmol of trifluoromethanesulfonic acid glycoside, reacting at 308K for 7 hours, filtering, repeatedly washing the solid for 3 times with 50mL of absolute ethyl alcohol and deionized water in sequence, and drying in vacuum to obtain solid B.
(2) Preparing an iridoid multi-component simultaneous imprinting composite material: weighing 0.42g of the solid B, adding the solid B into 33mL of acetonitrile-dimethyl sulfoxide-methanol (volume ratio is 2:2: 1) mixed solvent, adding 0.7mmol of geniposide-aucubin-pinoresinol diglucoside (molar ratio is 1:1: 1) mixture, 7.0mmol of divinylbenzene and 25.0mg of azobisisobutyronitrile, ultrasonically mixing for 5min, introducing argon for 15min, sealing the reaction container, placing the reaction container in 333K oil bath, controlling the rotating speed of the reaction container to be 12r/min, after reacting for 12 hours, pouring the reaction mixture into 50.0mL of methanol solution, settling for 4 hours, sucking out the upper-layer liquid, repeatedly settling for two times by using 50.0mL of water and acetonitrile respectively, each time for 4 hours, sucking out the upper-layer liquid, filtering, and vacuum drying the solid at 60 ℃ for 12 hours to obtain the molecular imprinting composite microspheres with the particle size of 20-50 mu m.
The molecular imprinting composite material microsphere has high selective adsorption capacity on blood pressure reducing compounds in the eucommia seed meal methanol extract, such as pinoresinol diglucoside, aucubin, geniposide and the like, can be used for selective adsorption and solid phase extraction separation and purification of certain blood pressure reducing active compounds in eucommia, and has good application efficiency.
The molecular imprinted polymer obtained by the invention is used as an adsorbent, and has the characteristic of simple extraction and separation process when the antihypertensive compound in the eucommia ulmoides crude extract is extracted, separated and purified in a solid phase, the target compound with higher purity can be obtained by single-step operation, the product recovery rate is high, and the imprinted polymer can be repeatedly used.
Loading 1.5 g of molecularly imprinted polymer powder into a solid phase extractor, washing residual compounds with 20mL of methanol and 20mL of acetonitrile, balancing with acetonitrile, injecting 12mL of eucommia seed meal methanol extract into the solid phase extractor, and first using 6mL of acetonitrile and 7mLH2In an O solventWashing, then using 6mL of methanol and 7mL of 0.002 mol L in sequence-1Na2HPO4-NaH2PO4Eluting with buffer solution and 7mL of methanol-acetic acid mixed solution (volume ratio of 8: 2), collecting eluates, and freeze drying or distilling under reduced pressure to remove solvent to obtain aucubin with purity of 77.3%, geniposide with purity of 75.6% and pinoresinol diglucoside with purity of 81.1%.
Example 2:
(1) preparing MIL-101 and carrying out sulfonylation modification: adding 1.0mmol of chromium nitrate nonahydrate and 2.3mmol of terephthalic acid into 50mL of deionized water, adding 0.4mL of hydrofluoric acid, ultrasonically stirring and uniformly mixing, pouring the mixed solution into a 100mL hydrothermal reaction kettle, sealing, reacting at the temperature of 493K for 11.5 hours, cooling, performing suction filtration, sequentially washing solids with deionized water and N, N-Dimethylformamide (DMF), transferring the solids into the reaction kettle, adding 50mL of ethanol, reacting at the temperature of 373K for 19 hours, filtering, repeatedly washing with ethanol, performing vacuum drying, grinding and sieving to obtain green solid powder MIL-101 (A); 4.0g of MIL-101 was charged into a 250mL flask, and 100mL of CH was added3NO2After stirring uniformly, adding 5.0 mmol of concentrated sulfuric acid and 9.0mmol of trifluoromethanesulfonic acid glycoside, reacting at 308K for 8.5 hours, filtering, repeatedly washing the solid with 50mL of absolute ethyl alcohol and deionized water for 3 times, and vacuum drying to obtain solid B.
(2) Preparing an iridoid multi-component simultaneous imprinting composite material: weighing 0.55g of the solid B, adding the solid B into 42mL of acetonitrile-dimethyl sulfoxide-methanol (volume ratio is 2:2: 1) mixed solvent, adding 0.8mmol of geniposide-aucubin-pinoresinol diglucoside (molar ratio is 1:1: 1) mixture, 8.5mmol of divinylbenzene and 25.0mg of azobisisobutyronitrile, ultrasonically mixing for 5min, introducing argon for 15min, sealing the reaction container, placing the reaction container in 333K oil bath, controlling the rotating speed of the reaction container to be 18r/min, after reacting for 12 hours, pouring the reaction mixture into 50.0mL of methanol solution, settling for 4 hours, sucking out the upper-layer liquid, repeatedly settling for two times by using 50.0mL of water and acetonitrile respectively, each time for 4 hours, sucking out the upper-layer liquid, filtering, and vacuum drying the solid at 60 ℃ for 12 hours to obtain the composite imprinting material microspheres with the particle size of 20-50 mu m.
The molecular imprinting composite material microsphere has high selective adsorption capacity on blood pressure reducing compounds in the eucommia seed meal methanol extract, such as pinoresinol diglucoside, aucubin, geniposide and the like, can be used for selective adsorption and solid phase extraction separation and purification of certain blood pressure reducing active compounds in eucommia, and has good application efficiency.
The molecular imprinted polymer obtained by the invention is used as an adsorbent, and has the characteristic of simple extraction and separation process when the antihypertensive compound in the eucommia ulmoides crude extract is extracted, separated and purified in a solid phase, the target compound with higher purity can be obtained by single-step operation, the product recovery rate is high, and the imprinted polymer can be repeatedly used.
For example, 1.5 g of molecularly imprinted polymer powder is loaded into a solid phase extractor, 20mL of methanol and 20mL of acetonitrile are used to wash residual compounds and acetonitrile is used for balancing, 14mL of eucommia ulmoides seed meal methanol extract is injected into the solid phase extractor, and 8mL of acetonitrile and 9mLH are used firstly2Washing with O solvent, and sequentially washing with 15mL of methanol and 14mL of 0.002 mol L-1Na2HPO4-NaH2PO4Eluting with buffer solution and 7mL of methanol-acetic acid mixed solution (volume ratio of 8: 2), collecting eluates, and freeze drying or distilling under reduced pressure to remove solvent to obtain aucubin with purity of 77.4%, geniposide with purity of 79.5%, and pinoresinol diglucoside with purity of 81.5%.
The above-described embodiments are not intended to limit the present invention in any manner, and those skilled in the art can make many possible variations and modifications to the technical solution of the present invention using the above-disclosed technical contents, or modify equivalent embodiments with equivalent variations, without departing from the scope of the technical solution of the present invention. Therefore, any simple modification, equivalent change and modification made to the above embodiments according to the technical spirit of the present invention should fall within the protection scope of the technical scheme of the present invention, unless the technical spirit of the present invention departs from the content of the technical scheme of the present invention.
Claims (3)
1. A preparation method of a iridoid multicomponent simultaneous imprinting composite material is characterized by comprising the following steps:
(1) preparing MIL-101 and carrying out sulfonylation modification: adding 1.0mmol of chromium nitrate nonahydrate and 1.0-3.0mmol of terephthalic acid into 50mL of deionized water, adding 0.2-0.5mL of hydrofluoric acid, ultrasonically stirring and uniformly mixing, pouring the mixed solution into a 100mL hydrothermal reaction kettle, sealing and reacting at the temperature of 493K for 10-12 hours, cooling and carrying out suction filtration, sequentially washing solids with deionized water and N, N-Dimethylformamide (DMF), transferring the solids into the reaction kettle, adding 50mL of ethanol, reacting at the temperature of 373K for 16-20 hours, filtering and repeatedly washing with ethanol, grinding and sieving after vacuum drying to obtain green solid powder MIL-101 (A); 4.0g of MIL-101 was charged into a 250mL flask, and 100mL of CH was added3NO2Adding 5.0 mmol of concentrated sulfuric acid and 5.0-10.0mmol of trifluromethyl glycoside after stirring uniformly, reacting for 6-10 hours at the temperature of 308K, filtering, repeatedly washing the solid for 3 times by using 50mL of absolute ethyl alcohol and deionized water in sequence, and drying in vacuum to obtain a solid B;
(2) preparing an iridoid multi-component simultaneous imprinting composite material: weighing 0.4-0.6g of solid B, adding the solid B into 30-45mL of acetonitrile-dimethyl sulfoxide-methanol (volume ratio is 2:2: 1) mixed solvent, adding 0.6-1.0mmol of geniposide-aucubin-pinoresinol diglucoside (molar ratio is 1:1: 1) mixture, 6.0-10mmol of divinylbenzene and 25.0mg of azobisisobutyronitrile, ultrasonically mixing for 5min, introducing argon for 15min, sealing a reaction container, placing the reaction container in 333K oil bath, controlling the rotating speed of the reaction container to be 10-20r/min, pouring the reaction mixture into 50.0mL of methanol solution after 12 hours of reaction, settling for 4 hours, sucking out the upper-layer liquid, repeatedly settling for two times by using 50.0mL of water and acetonitrile respectively, repeating for 4 hours each time, sucking out the upper-layer liquid, filtering, and vacuum drying the solid at 60 ℃ for 12 hours to obtain the composite imprinting material.
2. The imprinted composite material obtained by the preparation method according to claim 1, characterized in that: the imprinting composite material is microspheres with the particle size of 20-50 mu m, has high selective adsorption capacity on blood pressure reducing compounds in the methanol extract of eucommia seed meal, such as pinoresinol diglucoside, aucubin, geniposide and the like, can be used for selective adsorption and solid-phase extraction separation and purification of certain blood pressure reducing active compounds in eucommia, and has better application efficiency.
3. A method for simultaneously separating and purifying pinoresinol diglucoside, aucubin and geniposide in eucommia meal methanol extract is characterized by comprising the following steps: loading the iridoid multicomponent simultaneous imprinting composite material prepared according to claim 1 into a solid phase extractor, washing residual compounds with methanol and acetonitrile, balancing with acetonitrile, injecting the methanol extractive solution of eucommia seed meal into the solid phase extractor, and mixing with acetonitrile and H2Washing with O as solvent, and sequentially washing with methanol and 0.002 mol L-1Na2HPO4-NaH2PO4Eluting with buffer solution and methanol-acetic acid mixed solution (volume ratio of 8: 2), collecting eluates, freeze drying or distilling under reduced pressure to remove solvent, and separating high purity aucubin, geniposide and pinoresinol diglucoside.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113101903A (en) * | 2021-04-25 | 2021-07-13 | 李辉 | Novel method for separating and purifying geniposide by composite imprinted microspheres |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113101903A (en) * | 2021-04-25 | 2021-07-13 | 李辉 | Novel method for separating and purifying geniposide by composite imprinted microspheres |
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Application publication date: 20200218 |