Preparation and application of antibacterial and antioxidant plant extract compound
By modifying lignin solubilizing luteolin, stable nanocomposite antibacterial materials were prepared, which solved the problem of poor water solubility of luteolin, significantly improved its antioxidant and antibacterial properties, and promoted the healing of chronic wound wounds.
Patent Information
- Application Number
- CN202411806378.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-10
- Publication Date
- 2025-03-14
AI Technical Summary
The small molecules of luteolin have poor water solubility, which makes it unable to fully exert its antibacterial and antioxidant efficiency and is difficult to promote the healing of chronic wound wounds.
Solute the luteolin by solubilizing the luteolin with different degrees of substitution, and a stable lignin-luteolin nanocomposite antibacterial material is prepared, which utilizes its stability and antioxidant properties in water to promote wound healing.
The stable solubilization of luteolin in water has been achieved, which significantly improves its antioxidant and antibacterial properties, and effectively promotes the healing of chronic wound wounds.
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Figure CN119606944A_ABST
Abstract
Description
Technical Field
[0001] The invention relates to the field of chemistry and nanomaterials, and to a chemically modified preparation of lignin, and in particular to the preparation and application of a composite of plant-extracted lignin and luteolin. Background Art
[0002] The treatment of chronic wound bacterial infection is a clinical and research challenge. Bacteria and bacterial metabolites continuously stimulate the patient to produce an inflammatory response, causing the wound to stagnate in the inflammatory response period for a long time and delaying healing. The detection rate of multidrug resistance to antibiotics is as high as 36.8%, which has evolved into a serious social problem and poses a major threat to public health and safety. The killing effect of conventional antibiotics on drug-resistant bacteria continues to weaken, and the indiscriminate abuse of antibiotics in the medical process makes this problem more serious. Therefore, there is an urgent need to develop a new antibacterial strategy with potential.
[0003] Generally, new antibacterial strategies can clear bacteria from chronic wounds. However, in wound repair, there are three overlapping stages: inflammation, proliferation, and remodeling. The metabolic imbalance of immune cells represented by macrophages leads to the explosive release of proinflammatory factors and reactive oxygen species (ROS), which will hinder the proliferation and remodeling of skin tissue, making the wound still unable to be repaired. Mediating the reprogramming of M1 macrophages to M2 is conducive to promoting the transition of wounds from inflammation to proliferation and remodeling stages, and is an effective strategy to promote wound healing. Studies have shown that the removal of ROS in the wound microenvironment is one of the most effective immunoregulatory methods to regulate the polarization of macrophages to the M2 phenotype.
[0004] Natural medicines are gaining more and more attention in China and around the world because of their low toxicity, environmental protection, safety, and effectiveness. Luteolin belongs to the flavonoids. It was originally a golden needle-shaped substance isolated from the leaves, stems, and branches of the herbaceous plant Luteolin. It is a natural pigment component. However, it is slightly soluble in hot water, difficult to dissolve in cold water, and not stable enough, resulting in extremely low bioavailability and great waste. It is of great significance to fully tap its bioavailability.
[0005] Lignin is an important component of plant cell walls, accounting for 10-35wt% of their dry weight. It has the advantages of low cost, eco-friendliness and renewable. Lignin is rich in active groups such as benzene ring structures, aliphatic and aromatic hydroxyl groups. Due to its excellent biocompatibility, lignin has been widely used in the preparation of biomaterials. In addition, the abundant benzene ring structures in lignin can interact with drug molecules through π-π stacking, thereby self-assembling to form nanomaterials, showing good application prospects in the field of drug solubilization and sustained release. The structural formula of the natural monomer luteolin is as follows:
[0006] Summary of the invention
[0007] The purpose of the present invention is to overcome the fact that the current luteolin small molecule has poor water solubility and cannot fully exert its antibacterial and antioxidant efficiency, and to provide a method for preparing an antibacterial and antioxidant plant extract complex. The present invention uses modified lignin with different degrees of substitution to solubilize luteolin, synergistically antibacterial, and prepares a luteolin nanocomposite with the best degree of substitution and antibacterial and antioxidant water solution stability under the guiding principle of green chemistry, which cascades to promote the healing of chronic wounds.
[0008] In order to achieve the above object, the present invention adopts the following technical solution:
[0009] A method for preparing an antibacterial and antioxidant plant extract complex comprises the following steps:
[0010] (1) Weigh lignin into a round-bottom flask and add pyridine solution to completely dissolve the lignin;
[0011] (2) adding p-toluenesulfonyl chloride solution to the lignin solution of step (1), reacting in an ice-water bath for a certain period of time, adding hydrochloric acid solution after the reaction, washing with water and an organic solvent in sequence, and finally settling in an alcohol / water mixed solution, centrifuging, drying, and collecting the product to obtain lignin acid ester;
[0012] (3) dissolving the lignin ester obtained in step (2) in DMSO, adding ethylenediamine, reacting in an oil bath for a certain period of time, adding deionized water, collecting the precipitate by centrifugation, dissolving the precipitate with hydrochloric acid solution, dialyzing, and freeze-drying to obtain amino-modified lignin;
[0013] (4) dispersing the amino-modified lignin of step (3) in deionized water to obtain a lignin solution; dissolving luteolin in an organic solvent to obtain a luteolin solution; adding the luteolin solution dropwise to the lignin solution under stirring, and stirring the reaction at room temperature; dialyzing the obtained solution to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0014] Preferably, in step (1), the lignin is a mixture of one or more of kraft lignin, organic solvent lignin, alkali lignin, formaldehyde protected lignin, and enzyme hydrolyzed lignin.
[0015] Preferably, in step (2), the mass ratio of lignin to p-toluenesulfonyl chloride is 4:1-1:3, and the reaction time is 12-24h.
[0016] Preferably, in step (3), the mass ratio of ethylenediamine to lignin acid ester is 1:1-1:3, and the reaction time is 6-24h.
[0017] Preferably, in step (4), the mass ratio of the amino-modified lignin to luteolin is 2:1-10:1.
[0018] Preferably, in step (4), the organic solvent is a mixture of one or more of dimethyl sulfoxide, dimethylformamide, methanol and ethanol.
[0019] The present invention also provides a modified lignin luteolin nano-composite antibacterial material prepared by the above preparation method.
[0020] Furthermore, the present invention also provides the use of the modified lignin luteolin nanocomposite antibacterial material in the preparation of antibacterial and antioxidant preparations.
[0021] Preferably, the application is to prepare the amino-modified lignin luteolin into a nanoparticle dispersion for use as an antibacterial and antioxidant preparation.
[0022] The present invention also provides application of the modified lignin luteolin nanocomposite antibacterial material in preparing products for treating bacterially infected wounds.
[0023] Preferably, the bacteria include Methicillin-resistant Staphylococcus aureus.
[0024] The present invention has the following beneficial effects:
[0025] The present invention utilizes ethylenediamine to modify lignin to obtain amino-modified lignin with different substitution degrees. The amino-modified lignin can effectively solubilize luteolin. Luteolin and the amino-modified lignin are reacted to obtain a modified lignin luteolin nanocomposite antibacterial material that can form a stable nanoparticle dispersion in water, exerts significant antioxidant and antibacterial properties, can effectively promote the healing of chronic wounds, and has broad application prospects. BRIEF DESCRIPTION OF THE DRAWINGS
[0026] Figure 1 It is an amino-modified lignin prepared by reacting p-toluenesulfonyl chloride with different degrees of substitution with lignin and then further reacting with ethylenediamine.
[0027] Figure 2 It is Luteolin-ML UV Full Spectrum.
[0028] Figure 3 is the Luteolin-ML hydrated particle size.
[0029] Figure 4 The antibacterial activity of Luteolin at different concentrations against methicillin-resistant Staphylococcus aureus.
[0030] Figure 5 The antibacterial activity of Luteolin-ML at a concentration gradient against methicillin-resistant Staphylococcus aureus.
[0031] Figure 6 The relative turbidity of Luteolin and Luteolin-ML with concentration gradient on methicillin-resistant Staphylococcus aureus at 24h.
[0032] Figure 7 Figure 1 is the scavenging efficiency of ABTS by Luteolin-ML at different concentrations and commercial antioxidants, VC: ascorbic acid, EGCG: epigallocatechin gallate, TA: tannic acid. DETAILED DESCRIPTION
[0033] In order to better illustrate the purpose, technical solutions and advantages of the present invention, the technical solutions of the present invention are further described below in conjunction with the accompanying drawings and specific embodiments, but they should not be construed as limiting the protection scope of the present invention.
[0034] Example 1
[0035] (1) Weigh 1 g of organic solvent lignin into a 250 mL round-bottom flask and add 10 mL of pyridine solution to completely dissolve the lignin.
[0036] (2) Add p-toluenesulfonyl chloride solution to the lignin solution of step (1), the mass ratio of lignin to p-toluenesulfonyl chloride is 4:1, and react in an ice-water bath for 12 hours. After the reaction, add 0.1M hydrochloric acid solution, wash with water and acetone in sequence, and finally precipitate in 100mL of isopropanol / water (1:1, volume ratio) mixed solution, wash with deionized water 3 times, centrifuge, dry, collect the product, and obtain lignin acid ester.
[0037] (3) Weigh lignin ester, dissolve it in DMSO, add ethylenediamine solution, the mass ratio of ethylenediamine to lignin ester is 1:1, react in an oil bath for 12 hours, add deionized water, collect the precipitate by centrifugation, dissolve the precipitate with 1M hydrochloric acid solution, dialyze in a 3500Da molecular weight cutoff dialysis bag, and freeze-dry the solution after the dialysis to obtain amino-modified lignin.
[0038] (4) Weigh the amino-modified lignin and dissolve it in 10 mL of deionized water to obtain a lignin solution; weigh luteolin and dissolve it in 5 mL of dimethylformamide solution to obtain a luteolin solution. The mass ratio of amino-modified lignin to luteolin is 10:1. Then, at a speed of 300 rpm, the luteolin solution is added dropwise to the lignin solution, and the reaction is stirred at room temperature for 30 minutes. The obtained solution is dialyzed for 48 hours, and the molecular weight cutoff of the dialysis bag is 3500 Da. The solution after the dialysis is freeze-dried to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0039] Example 2
[0040] (1) Weigh 1 g of formaldehyde-protected lignin into a 250 mL round-bottom flask and add 10 mL of pyridine solution to completely dissolve the lignin.
[0041] (2) Add p-toluenesulfonyl chloride solution to the lignin solution of step (1), the mass ratio of lignin to p-toluenesulfonyl chloride is 2:1, and react in an ice-water bath for 24 hours. After the reaction, add 0.1M hydrochloric acid solution, wash with water and acetone in sequence, and finally precipitate in 100mL of isopropanol / water (1:1, volume ratio) mixed solution, wash with deionized water 3 times, centrifuge, dry, collect the product, and obtain lignin acid ester.
[0042] (3) Weigh lignin ester, dissolve it in DMSO, add ethylenediamine solution, the mass ratio of ethylenediamine to lignin ester is 1:1, react in an oil bath for 12 hours, add deionized water, collect the precipitate by centrifugation, dissolve the precipitate with 1M hydrochloric acid solution, dialyze in a 3500Da molecular weight cutoff dialysis bag, and freeze-dry the solution after the dialysis to obtain amino-modified lignin.
[0043] (4) Weigh the amino-modified lignin and dissolve it in 10 mL of deionized water to obtain a lignin solution; weigh luteolin and dissolve it in 5 mL of dimethylformamide solution to obtain a luteolin solution. The mass ratio of amino-modified lignin to luteolin is 10:1. Then, at a speed of 300 rpm, the luteolin solution is added dropwise to the lignin solution, and the reaction is stirred at room temperature for 30 minutes. The obtained solution is dialyzed for 48 hours, and the molecular weight cutoff of the dialysis bag is 3500 Da. The solution after the dialysis is freeze-dried to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0044] Example 3
[0045] (1) Weigh 1 g of alkali lignin into a 250 mL round-bottom flask and add 10 mL of pyridine solution to completely dissolve the lignin.
[0046] (2) Add p-toluenesulfonyl chloride solution to the lignin solution of step (1), the mass ratio of lignin to p-toluenesulfonyl chloride is 1:1, and react in an ice-water bath for 24 hours. After the reaction, add 0.1M hydrochloric acid solution, wash with water and acetone in sequence, and finally precipitate in 100mL of isopropanol / water (1:1, volume ratio) mixed solution, wash with deionized water 3 times, centrifuge, dry, collect the product, and obtain lignin acid ester.
[0047] (3) Weigh lignin ester, dissolve it in DMSO, add ethylenediamine solution, the mass ratio of ethylenediamine to lignin ester is 1:2, react in an oil bath for 24 hours, add deionized water, collect the precipitate by centrifugation, dissolve the precipitate with 1M hydrochloric acid solution, dialyze in a 3500Da molecular weight cutoff dialysis bag, and freeze-dry the solution after the dialysis to obtain amino-modified lignin.
[0048] (4) Weigh the amino-modified lignin and dissolve it in 10 mL of deionized water to obtain a lignin solution; weigh luteolin and dissolve it in 5 mL of methanol solution to obtain a luteolin solution. The mass ratio of amino-modified lignin to luteolin is 5:1. Then, at a speed of 300 rpm, the luteolin solution is added dropwise to the lignin solution, and the reaction is stirred at room temperature for 30 minutes. The obtained solution is dialyzed for 48 hours, and the molecular weight cutoff of the dialysis bag is 3500 Da. The solution after the dialysis is freeze-dried to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0049] Example 4
[0050] (1) Weigh 2 g of formaldehyde-protected lignin into a 250 mL round-bottom flask and add 20 mL of pyridine solution to completely dissolve the lignin.
[0051] (2) Add p-toluenesulfonyl chloride solution to the lignin solution of step (1), the mass ratio of lignin to p-toluenesulfonyl chloride is 1:2, and react in an ice-water bath for 12 hours. After the reaction, add 0.1M hydrochloric acid solution, wash with water and acetone in sequence, and finally precipitate in 100mL of isopropanol / water (1:1, volume ratio) mixed solution, wash with deionized water 3 times, centrifuge, dry, collect the product, and obtain lignin acid ester.
[0052] (3) Weigh lignin ester, dissolve it in DMSO, add ethylenediamine solution, the mass ratio of ethylenediamine to lignin ester is 1:2, react in an oil bath for 6 hours, add deionized water, collect the precipitate by centrifugation, dissolve the precipitate with 1M hydrochloric acid solution, dialyze in a 3500Da molecular weight cutoff dialysis bag, and freeze-dry the solution after the dialysis to obtain amino-modified lignin.
[0053] (4) Weigh the amino-modified lignin and dissolve it in 10 mL of deionized water to obtain a lignin solution; weigh luteolin and dissolve it in 5 mL of ethanol solution to obtain a luteolin solution. The mass ratio of amino-modified lignin to luteolin is 10:1. Then, the luteolin solution is added dropwise to the lignin solution at a speed of 300 rpm, and the reaction is stirred at room temperature for 30 minutes. The obtained solution is dialyzed for 48 hours, and the molecular weight cutoff of the dialysis bag is 3500 Da. The solution after the dialysis is freeze-dried to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0054] Example 5
[0055] (1) Weigh 2 g of enzymatically hydrolyzed lignin into a 250 mL round-bottom flask and add 20 mL of pyridine solution to completely dissolve the lignin.
[0056] (2) Add p-toluenesulfonyl chloride solution to the lignin solution of step (1), the mass ratio of lignin to p-toluenesulfonyl chloride is 1:3, and react in an ice-water bath for 24 hours. After the reaction, add 0.1M hydrochloric acid solution, wash with water and acetone in sequence, and finally precipitate in 100mL of isopropanol / water (1:1, volume ratio) mixed solution, wash with deionized water 3 times, centrifuge, dry, collect the product, and obtain lignin acid ester.
[0057] (3) Weigh lignin ester, dissolve it in DMSO, add ethylenediamine solution, the mass ratio of ethylenediamine to lignin ester is 1:3, react in an oil bath for 24 hours, add deionized water, collect the precipitate by centrifugation, dissolve the precipitate with 1M hydrochloric acid solution, dialyze in a 3500Da molecular weight cutoff dialysis bag, and freeze-dry the solution after the dialysis to obtain amino-modified lignin.
[0058] (4) Weigh the amino-modified lignin and dissolve it in 10 mL of deionized water to obtain a lignin solution; weigh luteolin and dissolve it in 5 mL of dimethylformamide solution to obtain a luteolin solution. The mass ratio of amino-modified lignin to luteolin is 2:1. Then, at a speed of 300 rpm, the luteolin solution is added dropwise to the lignin solution, and the reaction is stirred at room temperature for 30 minutes. The obtained solution is dialyzed for 48 hours, and the molecular weight cutoff of the dialysis bag is 3500 Da. The solution after the dialysis is freeze-dried to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0059] Example 6
[0060] (1) Weigh 2 g of kraft lignin into a 250 mL round-bottom flask and add 20 mL of pyridine solution to completely dissolve the lignin.
[0061] (2) Add p-toluenesulfonyl chloride solution to the lignin solution of step (1), the mass ratio of lignin to p-toluenesulfonyl chloride is 1:2, and react in an ice-water bath for 24 hours. After the reaction, add 0.1M hydrochloric acid solution, wash with water and acetone in sequence, and finally precipitate in 100mL of isopropanol / water (1:1, volume ratio) mixed solution, wash with deionized water 3 times, centrifuge, dry, collect the product, and obtain lignin acid ester.
[0062] (3) Weigh lignin ester, dissolve it in DMSO, add ethylenediamine solution, the mass ratio of ethylenediamine to lignin ester is 1:3, react in an oil bath for 24 hours, add deionized water, collect the precipitate by centrifugation, dissolve the precipitate with 1M hydrochloric acid solution, dialyze in a 3500Da molecular weight cutoff dialysis bag, and freeze-dry the solution after the dialysis to obtain amino-modified lignin.
[0063] (4) Weigh the amino-modified lignin and dissolve it in 10 mL of deionized water to obtain a lignin solution; weigh luteolin and dissolve it in 5 mL of dimethylformamide solution to obtain a luteolin solution. The mass ratio of amino-modified lignin to luteolin is 10:1. Then, at a speed of 300 rpm, the luteolin solution is added dropwise to the lignin solution, and the reaction is stirred at room temperature for 30 minutes. The obtained solution is dialyzed for 48 hours, and the molecular weight cutoff of the dialysis bag is 3500 Da. The solution after the dialysis is freeze-dried to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0064] Example 7
[0065] (1) Weigh 12 g of kraft lignin into a 250 mL round-bottom flask and add 120 mL of pyridine solution to completely dissolve the lignin.
[0066] (2) Add p-toluenesulfonyl chloride solution to the lignin solution of step (1), the mass ratio of lignin to p-toluenesulfonyl chloride is 1:3, and react in an ice-water bath for 24 hours. After the reaction, add 0.1M hydrochloric acid solution, wash with water and acetone in sequence, and finally centrifuge and wash in an alcohol / water (v / v 1:1) mixed solution, collect the product by centrifugation, and obtain lignin acid ester.
[0067] (3) Weigh lignin ester, dissolve it in DMSO, add ethylenediamine solution, the mass ratio of ethylenediamine to lignin ester is 1:1, react in an oil bath for 6 hours, add deionized water, collect the precipitate by centrifugation, dissolve the precipitate with 1M hydrochloric acid solution, dialyze in a 3500Da molecular weight cutoff dialysis bag, and freeze-dry the solution after the dialysis to obtain amino-modified lignin.
[0068] (4) Weigh the amino-modified lignin and dissolve it in 10 mL of deionized water to obtain a lignin solution; weigh luteolin and dissolve it in 5 mL of dimethylformamide solution to obtain a luteolin solution. The mass ratio of amino-modified lignin to luteolin is 10:1. Then, at a speed of 300 rpm, the luteolin solution is added dropwise to the lignin solution, and the reaction is stirred at room temperature for 30 minutes. The obtained solution is dialyzed for 48 hours, and the molecular weight cutoff of the dialysis bag is 3500 Da. The solution after the dialysis is freeze-dried to obtain a modified lignin luteolin nanocomposite antibacterial material (Luteolin-ML).
[0069] The amino-modified lignin with different degrees of substitution prepared by the present invention is as follows: Figure 1 As shown, the degree of substitution increases from left to right. Figure 2 As shown, the average hydrated particle size of the nanospheres is about 186 nm. Figure 3 As shown, the corresponding polydispersity index (PDI) is 0.1659, the corresponding zeta potential is 23.41 mV, and the zeta potential of MRSA is -30.24 mV.
[0070] Example 8
[0071] The antibacterial activity of Luteolin-ML and Luteolin in Example 6 was investigated by turbidimetry. 100 μL of Luteolin-ML and Luteolin with different concentration gradients were added to a 96-well plate. Then, 100 μL of 5×10 6 CFU / mL of bacteria, continue to culture for 24 hours. OD600 is measured every hour using a microplate reader (Synergy H1, BioTek, USA). Figure 4-6 It shows that compared with Luteolin, Luteolin-ML can effectively improve the activity of the nanodrug delivery system against methicillin-resistant Staphylococcus aureus.
[0072] Example 9
[0073] Weigh 81.2 mg of 2,2-azo-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and dissolve it in 20 mL of water to prepare an ABTS stock solution. Then weigh 14.1 mg of potassium persulfate and dissolve it in 20 mL of water to prepare a solution. Take a certain amount of ABTS stock solution and react it with potassium persulfate solution for 12-16 hours to prepare an ABTS cation radical solution. Take 1 mL of ABTS solution cation radical solution and dilute it with methanol so that its absorbance at 734 nm is close to 0.70. Then, 50 μL of sample solution and 950 μL of ABTS solution are reacted in the dark for 2 hours (37°C incubator), and a control group without sample is set (supplemented with 50 μL of water), and the absorbance of the solution at 734 nm is measured. Figure 7 It was shown that compared with commercial ascorbic acid (VC), epigallocatechin gallate (EGCG), and tannic acid (TA), Luteolin-ML can effectively resist oxidation and thus promote the healing of chronic wounds.
[0074] The above description is only a preferred embodiment of the present invention and is used to limit the present invention. Any modification, equivalent substitution, improvement, etc. made within the principle and content of the present invention should be included in the protection scope of the present invention.
Claims
1. A method for preparing an antibacterial and antioxidant plant extract complex, characterized in that: The following steps are involved: (1) Weigh lignin into a round-bottom flask and add pyridine solution to completely dissolve the lignin; (2) adding p-toluenesulfonyl chloride solution to the lignin solution of step (1), reacting in an ice-water bath for a certain period of time, adding hydrochloric acid solution after the reaction, washing with water and an organic solvent in sequence, and finally settling in an alcohol / water mixed solution, centrifuging, drying, and collecting the product to obtain lignin acid ester; (3) dissolving the lignin ester obtained in step (2) in DMSO, adding ethylenediamine, reacting in an oil bath for a certain period of time, adding deionized water, collecting the precipitate by centrifugation, dissolving the precipitate with hydrochloric acid solution, dialyzing, and freeze-drying to obtain amino-modified lignin; (4) dispersing the amino-modified lignin of step (3) in deionized water to obtain a lignin solution; dissolving luteolin in an organic solvent to obtain a luteolin solution; adding the luteolin solution dropwise to the lignin solution under stirring, and stirring the reaction at room temperature; dialyzing the obtained solution to obtain a modified lignin luteolin nanocomposite antibacterial material.
2. The preparation method according to claim 1, characterized in that: In step (1), the lignin is a mixture of one or more of kraft lignin, organic solvent lignin, alkali lignin, formaldehyde protected lignin, and enzyme hydrolyzed lignin.
3. The preparation method according to claim 1, characterized in that: In step (2), the mass ratio of lignin to p-toluenesulfonyl chloride is 4:1-1:3, and the reaction time is 12-24h.
4. The preparation method according to claim 1, characterized in that: In step (3), the mass ratio of ethylenediamine to lignin acid ester is 1:1-1:3, and the reaction time is 6-24h.
5. The preparation method according to claim 1, characterized in that: In step (4), the mass ratio of the amino-modified lignin to luteolin is 2:1-10:
1.
6. The modified lignin luteolin nanocomposite antibacterial material prepared according to the preparation method according to any one of claims 1 to 5.
7. Use of the modified lignin luteolin nanocomposite antibacterial material according to claim 6 in the preparation of antibacterial and antioxidant preparations.
8. The use according to claim 7, characterized in that: The modified lignin luteolin nano-composite antibacterial material is prepared into a nano-particle dispersion liquid for use as an antibacterial and antioxidant preparation.
9. Use of the modified lignin luteolin nanocomposite antibacterial material according to claim 6 in preparing products for treating bacterially infected wounds.
10. The use according to claim 9, characterized in that: The bacteria include Methicillin-resistant Staphylococcus aureus.