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CN-117797782-B - Enrichment purification material for flavonoid compounds, and preparation method and application thereof

CN117797782BCN 117797782 BCN117797782 BCN 117797782BCN-117797782-B

Abstract

The invention discloses an enrichment and purification material for flavonoid compounds, a preparation method and application thereof, wherein the enrichment and purification material is a magnetic covalent organic polymer material and comprises a magnetic core and a nano shell, wherein the nano shell is composed of repeated multi-ring units and has a structure shown in a formula (I). The magnetic covalent organic polymer material can be used for rapid and efficient purification and enrichment of flavonoid compounds in foods and traditional Chinese medicines, and has the advantages of high efficiency, small dosage, good stability, large adsorption capacity, easy separation and the like.

Inventors

  • ZHANG FENG
  • XIE YUN
  • LIU TONG
  • XU XIULI

Assignees

  • 中国检验检疫科学研究院

Dates

Publication Date
20260508
Application Date
20231207

Claims (20)

  1. 1. An enrichment and purification material for flavonoid compounds, which is characterized by comprising: A magnetic core formed of ferroferric oxide; A nano shell which covers at least part of the surface of the magnetic core, wherein the nano shell is composed of repeated multi-ring units and has a structural formula (I), the nano shell is of a porous structure, the average pore diameter is 2-4 nm, the thickness is 25-35 nm, Wherein the flavone is at least one selected from hesperetin, naringenin, glycitein, glycyrrhizin, pinocembrin and formononetin; 。
  2. 2. the enrichment purification material of claim 1, wherein the enrichment purification material has a specific surface area and a pore volume of 60-100 m 2 /g and 0.02-0.08 cm 3 /g, respectively.
  3. 3. The enrichment purification material according to claim 1, wherein the particle size of the magnetic core is 50-100 nm.
  4. 4. The enrichment and purification material according to claim 1, wherein the saturation adsorption amount of the enrichment and purification material to flavone is 90-210 mg.g -1 .
  5. 5. The enrichment purification material of claim 1, wherein the enrichment purification material has an adsorption equilibration time for flavonoids of 10-20 minutes.
  6. 6. The enrichment purification material of claim 1, wherein the enrichment purification material has a water contact angle of 55-65 °.
  7. 7. The enriched purification material of claim 1, wherein the surface of the enriched purification material comprises two binding sites.
  8. 8. A method of making the enriched purification material of any of claims 1-7, comprising: Dissolving Fe 3 O 4 nanoparticles and aldehyde monomer in organic solvent to obtain solution, and And dissolving amino monomers in the dissolving solution, and performing polymerization reaction to obtain the enrichment purifying material.
  9. 9. The method of claim 8, wherein the aldehyde-based monomer is 4,4',4 "(1, 3, 5-triazin-2, 4, 6-triyl) trityl aldehyde (TFPB).
  10. 10. The method of claim 8, wherein the amino monomer is tetrakis (4-aminophenyl) methane (TAPM).
  11. 11. The method of claim 8, wherein the molar ratio of the amino monomer to the aldehyde monomer is from 3:4 to 5.
  12. 12. The method of claim 8, wherein the polymerization reaction is conducted under catalyst conditions, wherein the catalyst is acetic acid.
  13. 13. The method according to claim 8, wherein the dissolution treatment is carried out under ultrasound for a period of 15-25 minutes.
  14. 14. The method according to claim 8, wherein the polymerization is carried out at 60-70 ℃ at 400-1000 rpm for 2-4 hours.
  15. 15. The method of claim 14, wherein the polymerization speed is 500 to 600 rpm.
  16. 16. The method of claim 8, wherein the organic solvent is tetrahydrofuran.
  17. 17. A method for adsorbing flavonoids, characterized in that it is carried out with the enrichment purification material according to any of claims 1-7.
  18. 18. The method of claim 17, wherein the saturated adsorption capacity of the enrichment and purification material is 90-210 mg-g -1 .
  19. 19. The method of claim 17, wherein the enrichment purification material has an adsorption equilibration time for flavonoids of between 10 and 20 minutes.
  20. 20. The method of claim 17, wherein the flavonoid is at least one selected from the group consisting of hesperetin, naringenin, glycitein, glycyrrhizin, pinocembrin and formononetin.

Description

Enrichment purification material for flavonoid compounds, and preparation method and application thereof Technical Field The invention relates to the field of chemistry, in particular to an enrichment and purification material, a preparation method and application thereof. Background Magnetic solid phase extraction (Magnetic solid phase extraction, MSPE) is a dispersive solid phase extraction technique with magnetic or magnetizable material as adsorbent. Compared with the traditional solid phase extraction technology, the MSPE is simple to operate, the adsorbent is not required to be filled in a solid phase extraction column, but is directly dispersed in a sample solution for adsorption, then the separation of the magnetic solid phase extraction material and the sample is realized by means of the action of an external magnetic field, and the separation and the enrichment of the target object are realized by eluting with an organic solvent. MSPE has the characteristics of high extraction efficiency, simple operation steps, wide application range and the like, and is an emerging effective sample pretreatment means. The flavonoid compound is one of main bioactive components in various foods and traditional Chinese medicines, and has various pharmacological and biochemical effects of resisting oxidation, bacteria, vascular diseases, inflammation and the like. However, extraction and separation of trace amounts of flavonoids from complex food or chinese medicine matrices still face a number of technical challenges, and development of efficient and selective enrichment purification materials is of paramount importance. Therefore, the magnetic enrichment purification material for extracting flavonoid compounds from different sample matrixes is required to be further studied. Disclosure of Invention The present invention aims to solve at least one of the technical problems existing in the prior art. Therefore, the invention aims to provide an enrichment purification material which has the advantages of good stability, large adsorption capacity, easiness in adsorption separation and the like. The inventor takes covalent organic polymer (Covalent Organic Polymers, COPs) as raw material, coats the surface of magnetic ferroferric oxide (Fe 3O4) to form an organic nano shell with a porous structure, and adopts the enrichment purification material to efficiently enrich flavonoid compounds in complex samples, and has strong adsorption capacity and rapidness. Covalent Organic Polymers (COPs) are porous organic polymers based on C, H, N, O and other light elements, and have wide application in the fields of separation, catalysis, sensing, drug delivery, energy collection and the like. In addition, the magnetic material provides a simpler and more effective substitute for the traditional solid-phase extraction adsorbent, can quickly realize the separation of the target in the complex sample, and overcomes the defect that the covalent organic polymer material is difficult to separate and recycle. Thus, according to one aspect of the present invention, there is provided an enriched purification material. According to the embodiment of the invention, the enrichment purification material comprises a magnetic core and a nano shell, wherein the magnetic core is formed by Fe 3O4, and the nano shell is covered on at least part of the surface of the magnetic core and is formed by repeated multi-ring units, and has the structural formula (I). According to the enrichment purification material provided by the embodiment of the invention, ferroferric oxide is used as a magnetic core, has magnetism, is easy to adsorb and separate, so that the problems that covalent organic polymers are inconvenient to use and operate, difficult to recycle and the like are solved, and the nano shell is a covalent organic polymer material, has a large specific surface area and good stability, and has a wide application prospect in the aspect of adsorption of flavonoid compounds. The enrichment purification material is used for adsorbing the flavonoid compounds, has strong specificity and short adsorption time, can adsorb and desorb the flavonoid compounds in a few minutes by using a very small amount of organic reagent, has the advantages of simple operation, time saving, high efficiency, environment friendliness and the like, and is particularly suitable for enrichment adsorption of the flavonoid compounds in complex samples, such as foods and traditional Chinese medicines. In addition, the enrichment and purification material according to the above embodiment of the present invention may further have the following additional technical features: according to the embodiment of the invention, the average pore diameter of the nanoshell is 2-4 nm, and the thickness is 30nm. According to an embodiment of the invention, the specific surface area and pore volume of the enrichment purification material are 60-100m 2/g and 0.02-0.08cm 3/g, respectively. According t