CN115246936B - Preparation method and application of hesperidin molecularly imprinted material based on MOFs - Google Patents
Preparation method and application of hesperidin molecularly imprinted material based on MOFs Download PDFInfo
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- 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
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
- B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
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- 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
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- C07—ORGANIC CHEMISTRY
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- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
Abstract
The preparation method of the hesperidin molecularly imprinted material based on MOFs is simple to operate, has the advantages of controllable scale, large specific surface area and stable performance, improves the exclusive selectivity of flavone separation, improves the extraction efficiency, is efficient and low in energy consumption, has a development significance, provides systematic theoretical support for industrial popularization by exploring the relation between the structure of MOFs and the extraction separation efficiency of plant active ingredients, and simultaneously provides possibility for on-line detection of the content of flavone substances in traditional Chinese medicines and Chinese patent medicines; by adopting rare earth yttrium (Y) as a ligand in MOFs metal organic frameworks, a plurality of active coordination points exist, stokes displacement is large, stability of the metal frameworks in water is improved, chemical stability and thermal stability of the metal frameworks are enhanced, and service life of the metal frameworks is prolonged.
Description
Technical Field
The invention relates to the technical field of plant extraction, in particular to a preparation method and application of a MOFs-based hesperidin molecularly imprinted material.
Background
The flavonoid compounds widely exist in plants, have strong biological activity and a plurality of potential values, and have the functions of resisting cancer, resisting tumor, resisting aging and the like. However, the flavone compounds are low in content in plants and various in variety and similar in structure, so that the extraction and separation of the flavone compounds are difficult. Therefore, how to establish efficient and highly selective rapid extraction and separation of flavonoids is a current urgent problem, and hesperidin belongs to citrus bioflavonoids, which comprises flavone glycosides and consists of flavone and rutin. Lemon and capsicum contain a large amount of hesperidin and are mainly concentrated on the pericarp and film. The sweet orange is one of the most abundant food sources, the flavonoid compounds in the pulp of the sweet orange are more abundant, and animal experiments show that the hesperidin is favorable for treating vascular diseases, cancers and some autoimmune diseases, and can be used as an antiallergic agent for people. It is an important nutrient substance, and together with vitamin C, it keeps collagen healthy, and avoids skin sagging and wrinkles caused by collagen rupture.
The prior art has been silent about the extraction of hesperidin, such as alcohol extraction, water extraction, continuous countercurrent extraction, etc., and the use of MOFs as separation and adsorption material.
Disclosure of Invention
The invention provides a preparation method of MOFs-based hesperidin molecularly imprinted material, which aims to solve the problems that the existing method for separating and extracting hesperidin from flavonoid plants has low extraction efficiency, difficult effect to be expected and difficult separation, and provides a specific hesperidin separation material with flavonoid substances with controllable scale, large specific surface area and stable performance, so as to improve the specific selectivity of hesperidin extraction and separation and the extraction efficiency.
The second object of the invention is to provide an application of MOFs-based hesperidin molecularly imprinted material in extracting hesperidin from flavonoid plants.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a preparation method of a MOFs-based hesperidin molecularly imprinted material comprises the following steps:
a1, adding hesperidin into a reaction container filled with a solution containing N, N-dimethylformamide, dissolving, and adding methanol and an acrylamide solution for prepolymerization for 2-5 hours to obtain a prepolymerized liquid;
a2, adding a cross-linking agent and an initiator into the prepolymerization liquid, adding rare earth-MOFs, performing ultrasonic degassing for 20-40min, filling nitrogen for 10-20min, and performing constant-temperature water bath reaction for 24h at the temperature of 60 ℃ to obtain a semi-finished product;
a3, eluting the semi-finished product by using a mixed solution of glacial acetic acid and methanol in a volume ratio of 2:8, then washing by using a methanol solution, and drying the obtained solid in vacuum at 50-70 ℃ for 10-14h to obtain the solid.
According to the preparation method of the MOFs-based hesperidin molecularly imprinted material, the adding ratio of the hesperidin to the N, N-dimethylformamide solution is 10-15:1-6mg/mL; the addition ratio of the acrylamide to the methanol is 10-30:5-15mg/mL.
According to the preparation method of the MOFs-based hesperidin molecularly imprinted material, the adding ratio of the initiator to the cross-linking agent is 20-40:0.1-1mg/mL.
The preparation method of the hesperidin molecularly imprinted material based on MOFs comprises the step of preparing an initiator, wherein the initiator is AIBN; the cross-linking agent is EDGMA.
The preparation method of the hesperidin molecularly imprinted material based on MOFs comprises the following steps: placing 1-4g of yttrium nitrate hexahydrate in a container, adding N, N dimethylformamide solution for dissolution, adding 1-2g of terephthalic acid powder for full mixing, and reacting for 24 hours at 150 ℃ to obtain mixed liquid; repeatedly washing the solid matter with N, N dimethylformamide solution and absolute ethanol solution respectively until the supernatant is colorless, filtering, and drying at 70deg.C for 12 hr to obtain the final product; by adopting the rare earth element yttrium (Y), a plurality of active coordination points exist, the Stokes displacement is larger, the stability of the metal framework in water is improved, the chemical stability and the thermal stability of the metal framework are enhanced, and the service life of the metal framework is prolonged.
According to the preparation method of the MOFs-based hesperidin molecularly imprinted material, in the step A1, the volume ratio of methanol to dimethylformamide in the methanol solution is 1:1.
According to the preparation method of the MOFs-based hesperidin molecularly imprinted material, the adsorption capacity of the MOFs-based hesperidin molecularly imprinted material on hesperidin is less than or equal to 56.00mg/g.
In order to achieve the second object, the present invention adopts the following technical scheme:
an application of MOFs-based hesperidin molecularly imprinted material in extracting hesperidin from flavonoid compounds comprises the following steps:
b1, adding a plant extraction solution into the MOFs-based hesperidin molecularly imprinted material obtained by the preparation method according to any one of the above, placing the plant extraction solution in a water bath constant temperature oscillator at room temperature for oscillation for 1h, centrifuging, and stirring for 5-15min at a stirring rate of 4000 rpm;
b2, filtering and separating the solution in the step B1 by using a 0.22 mu m microporous filter membrane to obtain MOFs hesperidin molecularly imprinted material after the solution is extracted by adsorbing plants;
b3, adding the MOFs hesperidin molecularly imprinted material obtained in the step B1 into a mixed solution of methanol and acetic acid with a volume ratio of 9:1, centrifuging for 10min at a speed of 4000rpm under the assistance of ultrasonic waves, and finally filtering with a 0.22 mu m microporous filter membrane to obtain a filtrate containing hesperidin.
The application of MOFs-based hesperidin molecularly imprinted material in extracting hesperidin from flavonoid compounds is characterized in that the ratio of the hesperidin molecularly imprinted material to the plant extraction solution is 15-30:1mg/mL.
Compared with the prior art, the invention has the following advantages:
1. the preparation method of the hesperidin molecularly imprinted material based on MOFs is simple to operate, has the advantages of controllable scale, large specific surface area and stable performance, improves the exclusive selectivity of flavone separation, improves the extraction efficiency, is efficient and low in energy consumption, has a development significance, provides systematic theoretical support for industrial popularization by exploring the relation between the structure of MOFs and the extraction separation efficiency of plant active ingredients, and simultaneously provides possibility for on-line detection of the content of flavone substances in traditional Chinese medicines and Chinese patent medicines; by adopting rare earth yttrium (Y) as a ligand in MOFs metal organic frameworks, a plurality of active coordination points exist, stokes displacement is large, stability of the metal frameworks in water is improved, chemical stability and thermal stability of the metal frameworks are enhanced, and service life of the metal frameworks is prolonged.
2. The application of the MOFs-based hesperidin molecularly imprinted material has the advantages of specific selectivity on hesperidin, high extraction efficiency, high purity, stable performance, repeated use for a plurality of times, maximum adsorption capacity of hesperidin reaching 56.00mg/g, and capability of being used for establishing an efficient, quick and sensitive molecularly imprinted system, so that hesperidin can be extracted from flavonoid compounds quickly, simply and conveniently.
Detailed Description
The following describes the specific technical scheme of the present invention in connection with specific examples 1 to 3:
example 1:
a preparation method of a MOFs-based hesperidin molecularly imprinted material comprises the following steps:
(1) Preparation of MOFs materials
Placing 3.46g of yttrium nitrate hexahydrate in a 100mL beaker, adding an N, N dimethylformamide solution for dissolution, adding 1.66g of terephthalic acid powder for full mixing, and reacting for 24 hours at 150 ℃ to obtain a mixed liquid; repeatedly washing the solid matter with N, N dimethylformamide solution and absolute ethanol solution respectively until the supernatant is colorless, filtering, and drying at 70 ℃ for 12 hours to obtain the Y-MOFs.
(2) Preparation of MOFs-based hesperidin molecularly imprinted material
50mg of hesperidin is added into a reaction vessel filled with 4mL of N, N-dimethylformamide solution for dissolution, 10mL of methanol solution is added, 23.3mgAM is added for prepolymerization for 5 hours, 0.4672mL of EDGMA and 30mg of initiator AIBN are then added, 100mg of Y-MOFs are added, ultrasonic degassing is carried out for 30min, nitrogen is filled for 15min, and a constant-temperature water bath kettle is used for reacting for 24 hours at 60 ℃.
Eluting the reaction product by using a mixed solution of glacial acetic acid and methanol in a volume ratio of 2:8, then washing the reaction product by using a methanol solution, and drying the obtained solid at 60 ℃ in vacuum for 14 hours to obtain the hesperidin molecularly imprinted material based on MOFs.
Example 2:
a preparation method of a MOFs-based hesperidin molecularly imprinted material comprises the following steps:
(1) Preparation of MOFs materials
Placing 1g of yttrium nitrate hexahydrate in a 100mL beaker, adding an N, N dimethylformamide solution for dissolution, adding 1.5g of terephthalic acid powder for full mixing, and reacting for 24 hours at 150 ℃ to obtain a mixed liquid; repeatedly washing the solid matter with N, N dimethylformamide solution and absolute ethanol solution respectively until the supernatant is colorless, filtering, and drying at 70 ℃ for 12 hours to obtain the Y-MOFs.
(2) Preparation of MOFs-based hesperidin molecularly imprinted material
100mg of hesperidin is added into a reaction vessel filled with 10mL of N, N-dimethylformamide solution for dissolution, 5mL of methanol solution is added, 28mgAM is added for prepolymerization for 5 hours, then 0.8mL of EDGMA and 20mg of initiator AIBN are added, 100mg of Y-MOFs are added, ultrasonic degassing is carried out for 30min, nitrogen is filled for 15min, and a constant-temperature water bath kettle is used for carrying out constant-temperature water bath reaction for 24h at 60 ℃.
Eluting the reaction product by using a mixed solution of glacial acetic acid and methanol in a volume ratio of 2:8, then washing the reaction product by using a methanol solution, and drying the obtained solid at 60 ℃ in vacuum for 14 hours to obtain the hesperidin molecularly imprinted material based on MOFs.
Example 3:
a preparation method of a MOFs-based hesperidin molecularly imprinted material comprises the following steps:
(1) Preparation of MOFs materials
2g of yttrium nitrate hexahydrate is placed in a 100mL beaker, N dimethylformamide solution is added for dissolution, 2g of terephthalic acid powder is added for full mixing, and the mixture is reacted for 24 hours at 150 ℃ to obtain mixed liquid; repeatedly washing the solid matter with N, N dimethylformamide solution and absolute ethanol solution respectively until the supernatant is colorless, filtering, and drying at 70 ℃ for 12 hours to obtain the Y-MOFs.
(2) Preparation of MOFs-based hesperidin molecularly imprinted material
150mg of hesperidin is added into a reaction vessel filled with 60mL of N, N-dimethylformamide solution for dissolution, 15mL of methanol solution is added, 10mgAM is added for prepolymerization for 5 hours, then 0.1mL of EDGMA and 40mg of initiator AIBN are added, 100mg of Y-MOFs are added, ultrasonic degassing is carried out for 30min, nitrogen is filled for 15min, and a constant-temperature water bath kettle is used for carrying out constant-temperature water bath reaction for 24 hours at 60 ℃.
Eluting the reaction product by using a mixed solution of glacial acetic acid and methanol in a volume ratio of 2:8, then washing the reaction product by using a methanol solution, and drying the obtained solid at 60 ℃ in vacuum for 14 hours to obtain the hesperidin molecularly imprinted material based on MOFs.
The MOFs-based hesperidin molecularly imprinted material prepared in the above examples 1-3 is respectively used for extracting hesperidin in a small citrus fruit extraction solution, the small citrus fruit extraction solution is added, the mixture is placed in a water bath at room temperature and a constant temperature oscillator for shaking for 1h, the mixture is centrifuged and stirred for 10min at a stirring rate of 4000rpm, the filtrate is analyzed and measured by a high performance liquid chromatography, then the mixture is filtered and separated by a 0.22 mu m microporous filter membrane, the MOFs-based hesperidin molecularly imprinted material after adsorbing the plant extraction solution is obtained, a mixed solution of methanol and acetic acid with a volume ratio of 9:1 is added, the mixture is centrifuged for 10min at a rate of 4000rpm under the assistance of ultrasonic waves, and finally the mixture is filtered by a 0.22 mu m microporous filter membrane, and the content of the hesperidin in the filtrate is analyzed and measured by the high performance liquid chromatography.
Table 1: MOFs-based hesperidin molecular imprinting Material of examples 1-3 adsorbed and desorbed amounts of hesperidin in the Small citrus fruit extraction solution
| Test item | Example 1 | Example 2 | Example 3 |
| Adsorption quantity | 40.46mg/g | 56.00mg/g | 54.90mg/g |
| Amount of desorption | 40.44mg/g | 55.89mg/g | 54.87mg/g |
As can be seen from the table, the adsorption quantity of the MOFs-based hesperidin molecularly imprinted material prepared in the embodiment 2 to hesperidin reaches the highest 56mg/g, so the preparation method of the MOFs-based hesperidin molecularly imprinted material is simple to operate, has the advantages of controllable scale, large specific surface area and stable performance, improves the exclusive selectivity of flavone separation, improves the extraction efficiency, is efficient, has low energy consumption, has low experimental material price, and has development significance; by adopting rare earth yttrium (Y) as a ligand in MOFs metal organic frameworks, a plurality of active coordination points exist, stokes displacement is large, stability of the metal frameworks in water is improved, chemical stability and thermal stability of the metal frameworks are enhanced, and service life of the metal frameworks is prolonged.
The foregoing description of the preferred embodiments of the present application is not intended to be limiting, but is intended to cover any and all modifications, equivalents, and alternatives falling within the spirit and principles of the present application.
Claims (8)
1. The preparation method of the hesperidin molecularly imprinted material based on MOFs is characterized by comprising the following steps of:
a1, adding hesperidin into a reaction container filled with a solution containing N, N-dimethylformamide, dissolving, and adding methanol and an acrylamide solution for prepolymerization for 2-5 hours to obtain a prepolymerized liquid;
a2, adding a cross-linking agent and an initiator into the prepolymerization liquid, adding rare earth-MOFs, performing ultrasonic degassing for 20-40min, filling nitrogen for 10-20min, and performing constant-temperature water bath reaction for 24h at the temperature of 60 ℃ to obtain a semi-finished product;
a3, eluting the semi-finished product by using a mixed solution of glacial acetic acid and methanol in a volume ratio of 2:8, then cleaning by using a methanol solution, and vacuum drying the obtained solid for 10-14h at 50-70 ℃ to obtain the solid;
the preparation method of the rare earth-MOFs comprises the following steps: placing 1-4g of yttrium nitrate hexahydrate in a container, adding N, N dimethylformamide solution for dissolution, adding 1-2g of terephthalic acid powder for full mixing, and reacting for 24 hours at 150 ℃ to obtain mixed liquid; repeatedly washing the solid with N, N dimethylformamide solution and absolute ethanol solution to obtain supernatant, filtering, and oven drying at 70deg.C for 12 hr.
2. The preparation method of the MOFs-based hesperidin molecularly imprinted material according to claim 1, wherein the preparation method comprises the following steps: the adding ratio of the hesperidin to the N, N-dimethylformamide solution is 10-15:1-6mg/mL; the addition ratio of the acrylamide to the methanol is 10-30:5-15mg/mL.
3. The preparation method of the MOFs-based hesperidin molecularly imprinted material according to claim 1 or 2, wherein the preparation method is characterized in that: the adding ratio of the initiator to the crosslinking agent is 20-40:0.1-1mg/mL.
4. The preparation method of the MOFs-based hesperidin molecularly imprinted material according to claim 3, wherein the preparation method comprises the following steps: the initiator is AIBN; the cross-linking agent is EDGMA.
5. The preparation method of the MOFs-based hesperidin molecularly imprinted material according to claim 1, wherein the preparation method comprises the following steps: in the step A1, the volume ratio of methanol to N, N-dimethylformamide in the methanol solution is 1:1.
6. The preparation method of the MOFs-based hesperidin molecularly imprinted material according to claim 1, wherein the preparation method comprises the following steps: the adsorption capacity of the MOFs-based hesperidin molecularly imprinted material to hesperidin is less than or equal to 56.00mg/g.
7. The application of MOFs-based hesperidin molecularly imprinted material in extracting hesperidin from flavonoid compounds is characterized by comprising the following steps:
b1, adding a plant extraction solution into the MOFs-based hesperidin molecularly imprinted material obtained by the preparation method according to any one of claims 1-6, placing the plant extraction solution in a water bath constant temperature oscillator for oscillation for 1h at room temperature, and centrifuging and stirring for 5-15min at a stirring rate of 4000 rpm;
b2, filtering and separating the solution in the step B1 by using a 0.22 mu m microporous filter membrane to obtain MOFs hesperidin molecularly imprinted material after the solution is extracted by adsorbing plants;
and B3, adding the MOFs hesperidin molecularly imprinted material obtained in the step B2 into a mixed solution of methanol and acetic acid with a volume ratio of 9:1, centrifuging for 10min at a speed of 4000rpm under the assistance of ultrasonic waves, and finally filtering with a 0.22 mu m microporous filter membrane to obtain a filtrate containing hesperidin.
8. The application of MOFs-based hesperidin molecularly imprinted material in extracting hesperidin from flavonoid compounds, which is characterized in that: the ratio of the hesperidin molecularly imprinted material to the plant extraction solution is 15-30:1mg/mL.
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