CN114805842B - Natural macromolecular polyanion derivative and green preparation method and application thereof - Google Patents
Natural macromolecular polyanion derivative and green preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H1/00—Macromolecular products derived from proteins
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/12—Preparation of cellulose esters of organic acids of polybasic organic acids
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Abstract
The invention discloses a natural macromolecular polyanion derivative, a green preparation method and application thereof. The natural macromolecular polyanion derivative is obtained by dissolving natural macromolecules in a solvent, adding modified molecules for reaction, separating ionic liquid after the reaction, and dialyzing and spin-drying. The invention introduces special groups into natural macromolecules to form natural macromolecule polyanion derivatives through specific green conditions, and can directly act on the surfaces of microorganisms through negative charges carried by the natural macromolecules, thereby inhibiting the infection ability of the microorganisms or directly killing the microorganisms to lose the infection ability. Because of its unique antimicrobial pathway, it is not afraid of including inherent variation of viruses and sources of different microbial varieties, and has been studied to have broad spectrum antimicrobial activity.
Description
Technical Field
The invention belongs to the field of natural macromolecule modification, and in particular relates to a natural macromolecule polyanion derivative, a green preparation method and application thereof.
Technical Field
The carbon-to-peak carbon neutralization is a multidimensional, stereoscopic and complete system engineering. Renewable resources such as animals and plants are utilized to replace petrochemical materials which are widely used at present to become the sustainable development direction of human beings, and meanwhile, the method is a way for eliminating chemical pollution, protecting ecological environment and promoting the harmonious development of human society and environment. Gluten protein is a byproduct of cereal starch processing, is a natural plant protein produced by plant metabolism, and is a natural polymer which is low in cost, biodegradable and renewable. Due to the unique physical properties and the like, the modified material can be modified in multiple aspects and is more and more valued by people. Cellulose is the most abundant natural organic matter in the world and accounts for more than 50% of the carbon content in the plant kingdom. Natural macromolecules are sustainable resources of human independent ore resources, and their utilization is consistent with the development of carbon-to-peak carbon neutralization. Antimicrobial substances, such as bleach, ethanol, etc., are generally capable of destroying microorganisms upon contact, but are extremely toxic to the human body, cannot be taken, or are administered to the human body. Current antiviral drugs act by inhibiting the growth of viruses, but they are not always effective for some time because viruses can become mutated and become resistant to them.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention provides a natural macromolecular polyanion derivative, a green preparation method and application.
The invention is realized by the following technical scheme:
the invention discloses a natural macromolecular polyanion derivative, which is characterized in that the tail end of a natural macromolecular with double-bond alkyl is carboxyl.
The invention also discloses a green preparation method of the natural macromolecular polyanion derivative, which comprises the following steps: dissolving natural macromolecular in solvent, adding modified molecule for reaction, separating ionic liquid after reaction, dialyzing, spin-drying to obtain natural macromolecular polyanion derivative.
As a further improvement, the molar ratio of the average molecular weight of the natural macromolecular monomer to the modified molecule is 6-2: 1, a step of; the solvent is ionic liquid, and the mass ratio of the natural macromolecule to the ionic liquid is 1: 15-25; the reaction time is 24-36 hours, the ionic liquid is used for recycling after separation, the dialysis time of the modified natural macromolecules is 72-96 hours, and the natural macromolecule polyanion derivatives are characterized by infrared and the like.
As a further improvement, the modified molecule is characterized in that the tail end of the hydrocarbon group is carboxyl on the long chain of the natural macromolecule to form a natural macromolecule polyanion derivative, the anion modified molecule is preferably citraconic anhydride and itaconic anhydride, the unique hydrocarbon group with double bonds changes the space configuration and conformation of the natural macromolecule, and the polarity, hydrophobicity and charge condition of the original macromolecule are changed.
As a further improvement, the natural macromolecules of the invention are preferably gluten and cellulose, and the ionic liquid is preferably 1-ethyl-3-methylimidazole tetrafluoroborate.
The invention also discloses application of the natural macromolecular polyanion derivative in resisting fungi, wherein the fungi comprise aspergillus niger, aureobasidium pullulans and penicillium pinophilum.
The invention also discloses biological application of the natural macromolecular polyanion derivative in resisting bacteria, wherein the bacteria comprise escherichia coli, staphylococcus aureus and bacillus subtilis.
The invention also discloses an application of the natural macromolecular polyanion derivative in resisting viruses, including DNA viruses, RNA viruses and DNA-RNA retroviruses.
The invention also discloses biological application of the natural macromolecular polyanion derivative in anti-tumor and drug delivery. Improving the water solubility of the medicine, slowly releasing the medicine, promoting absorption and targeting transfer of medicine auxiliary agent.
The invention also discloses application of the natural macromolecular polyanion derivative in agriculture, literature and environmental protection antimicrobial auxiliary agents, disinfection, washing, adsorptive protection and antimicrobial fabrics.
The beneficial effects of the invention are as follows:
the natural macromolecule is introduced into the natural macromolecule polyanion derivative through a specific green condition, and negative charges carried by the natural macromolecule polyanion derivative directly act on the surface of the microorganism, so that the infection capacity of the microorganism is inhibited, or the microorganism is directly killed to lose the infection capacity. Because of its unique antimicrobial pathway, it is not afraid of including inherent variation of viruses and sources of different microbial varieties, and has been studied to have broad spectrum antimicrobial activity.
The present patent relates to the use of natural macromolecular polyanion derivatives for simultaneous antifungal and antibacterial applications.
This patent relates to the simultaneous use of natural macromolecular polyanionic derivatives for inhibiting viruses including: DNA viruses such as Herpes Simplex Virus (HSV) and Human Papilloma Virus (HPV); RNA viruses such as influenza virus (IAV), dengue virus (DENV), human Rhinovirus (HRV), and Tobacco Mosaic Virus (TMV); DNA-RNA retroviruses such as Human Immunodeficiency Virus (HIV) and Hepatitis B Virus (HBV). And include unknown viruses that occur from new coronaviruses and the like.
The patent relates to the use of natural macromolecular polyanion derivatives for anti-tumor biological applications.
This patent relates to the use of natural macromolecular polyanionic derivatives for drug delivery biological applications at the same time. Improving the water solubility of the medicine, slowly releasing the medicine, promoting absorption and targeting transfer of medicine auxiliary agent.
This patent relates to the use of natural macromolecular polyanionic derivatives for simultaneous use in supramolecular chemistry.
The patent relates to the use of natural macromolecular polyanion derivatives in food additives, agriculture and environmental protection additives.
The present patent relates to the use of natural macromolecular polyanion derivatives for both sanitizing, adsorptive protection and antimicrobial fabric applications.
This patent relates to the use of natural macromolecular polyanionic derivatives MC for antimicrobial applications. If MC molecules are used to destroy the glycoprotein outer shell of microorganisms, this would destroy the infectious microorganisms when in contact, rather than just limiting their growth, would prevent the development of drug resistance, would have broad spectrum efficacy, would be non-toxic to humans, and would be important to be able to face the variations of known microorganisms, including viruses, and would also be able to break their glycoprotein outer shell in the face of unknown microorganisms.
The viral life cycle has interspecies variability, essentially consisting of viral adsorption, invasion, uncoating, transcription and replication, viral assembly and viral release processes. Possible pathways for inhibition of viruses by the natural macromolecular polyanionic derivative MC: the negative charge carried by the virus can be directly used with the surface of the virus, so that the infection capacity of the virus can be inhibited, or the virus can be directly killed to lose the infection capacity.
In the process of modifying natural macromolecules, the patent adopts green solvent ionic liquid aiming at the characteristics of rich natural macromolecule hydrogen bond network and the like, and has the advantages of non-volatility, incombustibility, good thermal stability, strong dissolving capacity, recycling and the like compared with the conventional organic solvent. In the process of selecting the ionic liquid, the ionic liquid is optimized for reaction promotion, price and post-treatment factors, and preferably 1-ethyl-3-methylimidazole tetrafluoroborate is used as a solvent. In natural macromolecular research, ionic liquids are commonly used in extraction or solubility research.
Detailed Description
The technical scheme of the invention is further described below with reference to specific embodiments.
Example 1
The natural macromolecular gluten 4 g is dissolved in ionic liquid 1-ethyl-3-methylimidazole tetrafluoroborate 80 g, and citraconic anhydride 0.58 g is added for reaction at room temperature for 24 hours. And separating the ionic liquid by utilizing different substrate solubilities, and recycling the ionic liquid. The modified natural macromolecule was dialyzed against a molecular weight 2000 dialysis membrane for 72 hours and rotary evaporated to give 3.5 g of the product MC1. The natural macromolecular polyanion derivative is characterized by infrared and the like.
Example 2
4 g of natural macromolecular soybean protein is dissolved in 90 g of ionic liquid 1-ethyl-3-methylimidazole tetrafluoroborate, 0.7 g of itaconic anhydride is added, and the mixture is reacted for 24 hours at room temperature. Separating the ionic liquid, and recycling the ionic liquid. The modified natural macromolecule is dialyzed by a molecular weight 2000 dialysis membrane for 72 hours, and 3.8 g of product MC2 is obtained by rotary evaporation. The natural macromolecular polyanion derivative is characterized by infrared and the like.
Example 3
4 g of natural macromolecular cellulose is dissolved in 85 g of ionic liquid 1-ethyl-3-methylimidazole tetrafluoroborate, 1.0 g of itaconic anhydride is added, and the mixture is reacted for 24 hours at room temperature. Separating the ionic liquid, and recycling the ionic liquid. The modified natural macromolecule was dialyzed against a molecular weight 2000 dialysis membrane for 72 hours and rotary evaporated to give 4.3 g of product MC3. The natural macromolecular polyanion derivative is characterized by infrared and the like.
1. Characterization method of natural macromolecular polyanion derivative
1.1 IR Spectroscopy testing the MC product structure was characterized by a Fourier transform IR spectrometer. Wavenumber from 400cm －1 To 4000cm －1 The scanning times are 32 times, and the resolution is 4cm －1 。
1.2 determination of protein derivative hydrophobicity (endogenous fluorescence) 100 μl of MC1 or MC2 samples at a concentration of 10mg/mL were accurately removed, added with 20.0mL deionized water and mixed well. The fluorescence emission spectrum is measured by a fluorescence spectrophotometer at room temperature, the excitation wavelength is set to 280nm, the acquisition range of the emission spectrum is 290-450 nm, the slits of the excitation wavelength and the emission wavelength are both 5.0nm, and the scanning speed is 240nm/min.
2. Conclusion(s)
2.1 Infrared results
2.2.1 MC1 or MC2 analysis: the infrared of MC1 or MC2 is distinguished from the protein material. In particular 1700-1660 cm -1 Is beta-corner 1652-1649 cm -1 Is alpha-helix 1648-1641 cm -1 Is randomly curled, 1640-1600 cm -1 Is beta-sheet. Analysis of the increase in random coil shows that acylation increases net negative charge and proximity repulsion in place of remote attraction opens the protein structure and also weakens the attraction between amino and carbonyl groups in the protein moleculeThe degree of aggregation of the protein molecules.
2.1.2 MC3 analysis: 3400cm －1 The absorption peak is the stretching vibration of O-H, corresponding to the hydroxyl in the molecular chain of cellulose, compared with the cellulose raw material, MC3 is 1735cm －1 There was a very pronounced absorption peak, which corresponds to a c=o stretching vibration peak, the absence of c=o in the cellulose raw material, indicating that the prepared sample was successfully grafted.
2.2 protein derivative hydrophobicity analysis: the maximum fluorescence emission intensity of gluten protein and soybean protein is 671.22 and 623.23, the maximum fluorescence emission intensity is reduced to 429.12 and 412.33 after acylation, the maximum emission wavelength is red shifted and is increased from 339nm to 346nm, and therefore, the acylation obviously changes the microenvironment of tryptophan residues of the protein, and the hydrophobicity of the protein is reduced. Prior to the acylation modification, gluten λmax was 339nm, indicating that the amino acid residue was in a hydrophobic environment. After the acylation modification, the maximum fluorescence emission intensity is reduced, and the microenvironment hydrophobicity of the amino acid residue is reduced.
Screening experiments and results of 3 MC cell activities against RSV, HSV-2, HSV-1, H3N2A3 virus strains
1. Experiment: 3 MC cell activity screens against RSV, HSV-2, HSV-1, H3N2A3 virus strains were performed. Vero cells were used as test model, and the test concentrations of the samples were 300, 150, 75, 37.5, 19ug/ml. After 1 hour incubation of MC with cells, virus infection was performed for 2 hours, virus solution was removed, fresh medium was changed, and cytopathic rate CPE (scoring 0, 25%,50%,75%,100% based on the diseased cells) was evaluated for 72 hours to determine the inhibition of MC virus.
2 results: sample antiviral induced Cytopathic (CPE) evaluation: the samples CM1, CM2 and CM3 have remarkable inhibition effect on cytopathic effect induced by Respiratory Syncytial Virus (RSV), and the IC50 is 106.73 mug/mL, 53.17 mug/mL and 120.17 mug/mL respectively; CM1, CM2 and CM3 have remarkable inhibition effect on the cytopathic effect induced by type 2-herpes simplex virus HSV-II, and IC50 is 106.73 mug/mL, 127.52 mug/mL and 150.67 mug/mL respectively; CM1, CM2 and CM3 have remarkable inhibition effect on induced cytopathic effect of type 1-herpes simplex virus (HSV-1), and IC50 is 86.72 mug/mL, 97.43 mug/mL and 140.13 mug/mL respectively; inhibition of induced cytopathic effects of CM1, CM2 and CM3 on influenza virus (H3N 2A 3) with IC50 of 156.48. Mu.g/mL, 187.28. Mu.g/mL, 170.51. Mu.g/mL, respectively.
In conclusion, the protein polyanionic derivatives CM1, CM2 have a stronger antiviral effect than the polysaccharide polyanionic derivatives CM 3. The inhibition of different viruses by the same derivative is different.
Experiment for inhibiting fungi and bacteria
Oxford cup method (1) sterilizing oxford cup at 121 ℃ with high-pressure steam for 20min, and placing the oxford cup in an ultra clean bench for standby. The sterilized solid medium was cooled to about 60℃and added to sterile plates, each of which was about 20mL, and placed in an ultra-clean bench to be coagulated. (2) Marking strain, oxford cup placement position and medicine concentration. (3) sucking 500. Mu.L of the bacterial liquid, and uniformly coating by using a coating rod. (4) Sterile oxford cups are taken by sterile forceps, placed vertically on the surface of a culture medium, lightly pressurized to enable the oxford cups to be in contact with the culture medium, 200 mu L of liquid medicine is added into the cups, a sample solvent (sterile physiological saline) is used as a negative control, a plate after sample addition cannot move at will, the movement is slow when the plates are transferred to a constant-temperature incubator, and the culture position is flat. After the sample is added, placing the plane in a constant temperature incubator, culturing for 48 hours at 28 ℃, and observing the result, determining the size of the antibacterial circle by a colony counter, and considering that the detection sample has antibacterial effect when the diameter of the antibacterial circle is larger than 6 mm. The test concentration of the sample was 0.1%,0.2%,0.5%,0.7%. The experimental determination standard of the inhibition zone is that the inhibition zone is larger than 20mm and extremely sensitive; 15-20 mm, high sensitivity; 10-15 mm, and is sensitive; 7-10 mm, low sensitivity; less than 7mm, and is insensitive.
2 results:
TABLE 1 diameter of fungal circle and bacteriostatic Effect (0.5% CM)
The inhibiting effect of CM1, CM2 and CM3 on Aspergillus niger is more obvious than other fungi, and the inhibiting effect on Aureobasidium pullulans is the next more. CM1, CM2 and CM3 showed a mesosensitization to inhibition by aureobasidium pullulans, bursa of cristata and penicillium pinophilum. The inhibition effect of CM1 on four fungi is better than that of CM2 and CM 3. Preferably 0.5% in the test concentration of the sample.
TABLE 2 diameter of antibacterial ring and antibacterial effect (0.5% CM)
CM1, CM2 and CM3 showed inhibitory effects on three bacteria. The inhibition of CM1 expression is more prominent. CM1 and CM2 are protein derivatives, but they are also different in protein structure and different in inhibition. CM1, CM2 and CM3 are all polyanion derivatives, but the main chains are different, the acid anhydride reaction positions are different, and the derivative structures are different; for example, the main chain of CM3 is polysaccharide, and the structure of CM is different from that of CM1 and CM2, so that the total inhibition of CM3 on microorganisms is obviously different from that of CM1 and CM 2.
CM in Xuan paper antifungal Performance test
1CM test of antifungal Properties on Xuan paper: the experiment used a wet room suspension method.
Cutting rice paper into small paper strips of about 1X 5cm, uniformly coating 0.5% of CM1, CM2 and CM3 and paste on the paper strips, and sticking another paper strip. 1ml of 1X 10 was accurately measured by a 200. Mu.l-1000. Mu.l pipette 7 Aspergillus niger, aureobasidium pullulans and Eurotium cristatum bacterial liquid with left and right concentrations are respectively and uniformly dripped on the prepared paper strips. The strips were suspended in an incubator at 28℃with 90% humidity for 28 days, during which time the growth of mold on the strips was continuously observed.
2 results
Table 3 CM results of antifungal application to Xuan paper
| Growth status of 28-day fungus | Aspergillus niger | Aureobasidium pullulans | Penicillium pinophilum |
| CM1 | 1 | 2 | 1 |
| CM2 | 2 | 3 | 3 |
| CM3 | 2 | 3 | 2 |
Evaluation of mildew-proof Effect
| Mold growth condition | Mildew resistant grade |
| No obvious mould growth under magnifying glass | 0 |
| Mold growth is rare or local, and the coverage area on the surface of the sample is less than 10 percent | 1 |
| Mold coating on sample surfaceThe cover area is less than 30 percent (10 to 30 percent) | 2 |
| The coverage area of the mould on the surface of the sample is less than 60 percent (30 to 60 percent) | 3 |
| The coverage area of mould on the surface of the sample reaches or exceeds 60 percent | 4 |
Agricultural product preservation application experiment
1. And (3) agricultural product preservation application experiments. The preservation object is fresh garlic. CM1, CM2, CM3 were prepared as 0.1%,0.3%,0.5%,0.7% aqueous solutions, 50ML per kg was sprayed, and the mixture was left at 0 ℃ for one month with fresh garlic blank, and the mildew effect was observed.
2. Results: CM1 and CM2 were observed to be mildew-proof at a concentration of 0.3% or more, with 0% and 0.1%, and 0.3% CM1 and CM2 being mildew-proof. CM2 is mildewproof at a concentration of 0.5% or more. Considering economic benefits, CM1 and CM2 are applied at 0.3% and CM3 is applied at 0.5%.
Project funding: 2013C14012 is special for international technological cooperation in Zhejiang province; thirteen-five national emphasis development planning project 2020YFC1521800; natural science foundation LQY B060002 of Zhejiang province; the Zhejiang province cultural relics protection technology project 2020011; jiangsu province scientific and technological project XZ-SZ202027
The above description is not intended to limit the invention, and it should be noted that: it will be apparent to those skilled in the art that various changes, modifications, additions or substitutions can be made without departing from the spirit and scope of the invention and these modifications and variations are therefore considered to be within the scope of the invention.
Claims (3)
1. The application of a natural macromolecular polyanion derivative in preparing an antifungal agent is characterized in that fungi comprise aspergillus niger and aureobasidium pullulans, and the preparation method of the natural macromolecular polyanion derivative comprises the following steps: the natural macromolecules are dissolved in the ionic liquid, modified molecules are added for reaction, the ionic liquid is separated after the reaction, and natural macromolecular polyanion derivatives are obtained through dialysis and spin drying, wherein the modified molecules are citraconic anhydride or itaconic anhydride, and the natural macromolecules are gluten.
2. The application of the natural macromolecular polyanion derivative in preparing an antibacterial agent is characterized in that bacteria comprise staphylococcus aureus and bacillus subtilis, and the preparation method of the natural macromolecular polyanion derivative comprises the following steps: the natural macromolecules are dissolved in the ionic liquid, modified molecules are added for reaction, the ionic liquid is separated after the reaction, and natural macromolecular polyanion derivatives are obtained through dialysis and spin drying, wherein the modified molecules are citraconic anhydride or itaconic anhydride, and the natural macromolecules are gluten.
3. The application of natural macromolecular polyanion derivatives in preparing antiviral agents is characterized in that the viruses comprise HSV-2 virus, HSV-1 virus and H3N2A3 virus, and the preparation method of the natural macromolecular polyanion derivatives comprises the following steps: the natural macromolecules are dissolved in the ionic liquid, modified molecules are added for reaction, the ionic liquid is separated after the reaction, and natural macromolecular polyanion derivatives are obtained through dialysis and spin drying, wherein the modified molecules are citraconic anhydride or itaconic anhydride, and the natural macromolecules are gluten.
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