CN116370498A - Composition containing chitosan or derivative thereof, preparation method and application thereof - Google Patents
Composition containing chitosan or derivative thereof, preparation method and application thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/7024—Esters of saccharides
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention provides a composition containing chitosan or a derivative thereof, a preparation method and application thereof. The composition comprises 2.5-15 parts by weight of plant source acid based on 100 parts by weight; 5-10 parts by weight of chitosan or a derivative thereof; 0.5 parts by weight of acid liquor and the balance of deionized water; the acid liquor is acetic acid, the composition is in a semisolid or liquid state, and the pH value of the composition is 5.5-6.0. The provided composition can promote the solubility of chitosan and has high antibacterial capability.
Description
Technical Field
The invention relates to a composition containing chitosan or a derivative thereof, a preparation method and application thereof.
Background
Chitosan is the only basic polysaccharide in nature, and mainly through deacetylation treatment of chitin, the product when the deacetylation degree exceeds 55% can be called chitosan. The chitosan has unique permeability, film forming property and biocompatibility, is an environment-friendly high polymer material with biological sources, and is widely applied to industrial products, agricultural plant protection, pharmaceutical appliance development and cosmetic production processes. In the medical device sector, chitosan has been used for wound hemostasis in multiple applications and to promote wound healing.
Tannic acid, also known as tannic acid, is a plant-derived natural polyphenol, which is certified by the FDA as a safe natural polyphenol and widely distributed in roots, stems, leaves and fruits of plants, and the annual yield of tannic acid in the world is inferior to that of cellulose and chitosan. The possibility of tannic acid being a multifunctional material is given by the fact that tannic acid contains a large number of functional groups of hydroxyl groups and ester groups in the molecule. Because of wide source, low price and unique physicochemical properties, the tannic acid is widely applied to leather manufacturing, food processing, medicine and daily chemical production processes. Tannic acid has strong antioxidation property and has certain antibacterial property.
In daily life and in special environments, the skin surface and mucous membrane of a human body are inevitably wounded. The maintenance of a sterile environment of the wound site plays an important role in wound healing. The relationship between the ability of bacteria to create a stable community within a wound and the ability of the host to resist the bacterial community can affect wound healing and infection. Following bacterial invasion into a wound, the ability of the body to control these microorganisms appears to decrease as the biofilm community matures, rapidly forming its own protective microenvironment. And in a stable, very dominant community, interactions between different species of bacteria can enhance their ability to cause infections and delay healing.
The chitosan has certain antibacterial property, most microorganisms have negative surface charges, and the molecular structure of the chitosan has NH 3 + The radicals being positiveThe electricity can be adsorbed on the cell wall of the microorganism to cause cell wall damage, outflow of inner solubles and damage of cell homeostasis, and can be combined with nucleic acid in the microorganism to resist the replication and expression of the nucleic acid. However, some of the characteristics of chitosan itself have an effect on its antimicrobial ability. The deacetylation degree and the molecular weight of chitosan are in positive correlation with the antibacterial property of chitosan within a certain range. The chitosan is insoluble in water, the solubility is lower as the molecular weight is larger, and when the molecular weight of the chitosan exceeds 30.5 ten thousand, the antibacterial capability is reduced; the higher the chitosan deacetylation degree is, namely the content of free amino in the molecular structure is increased, the antibacterial efficiency is improved, and the molecular mass is increased along with the increase of the molecular mass. Chitosan itself has antibacterial properties, but its antibacterial effect is not ideal due to its physical properties.
How to improve the antibacterial effect of chitosan needs to be solved.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems in the related art to some extent. The invention provides a composition containing chitosan or a derivative thereof, a preparation method and application thereof.
Specifically, the invention provides the following technical scheme:
according to a first aspect of the present invention there is provided a composition comprising chitosan or a derivative thereof, the composition comprising 100 parts by weight of: 2.5-15 parts by weight of plant source acid; 5-10 parts by weight of chitosan or a derivative thereof; 0.5 parts by weight of an acid solution (the acid solution may be acetic acid); and the balance water, said composition being in a semi-solid or liquid state. The composition provided by the invention creatively introduces the plant source acid, the plant source acid has a phenolic hydroxyl structure, and can release hydrogen ions in water, so that the solubility of chitosan is improved, and the composition and the acid liquor provide a weakly acidic environment, so that the solubility of chitosan under weak acid condition is promoted, and the antibacterial capability of the formed composition is effectively improved. The provided composition has simple formula and simple preparation, can reduce the influence of the molecular weight and the deacetylation degree of chitosan on the antibacterial property of the chitosan, and shows good antibacterial effect. Moreover, since chitosan is usually dissolved by a large amount of acid solution, such as acetic acid solution, the product has strong acidity, and when the chitosan is applied to the surface of skin or mucosal wounds, the chitosan stimulates the skin and influences the healing of the wounds or the wounds. The acid liquor content in the composition provided by the application is small and only accounts for 0.5 weight part, the pH value is maintained at about 6 (for example, 5.5-6.0), the composition does not stimulate the wound, and the wound can heal as soon as possible.
According to an embodiment of the present invention, the composition comprising chitosan or a derivative thereof may further comprise the following technical features:
according to an embodiment of the present invention, the plant-derived acid is at least one selected from tannic acid, gallic acid, schisandra acid.
According to an embodiment of the present invention, the chitosan or the derivative thereof is selected from at least one of chitosan, carboxymethyl chitosan, quaternary ammonium salt chitosan, and carboxymethyl quaternary ammonium salt chitosan.
According to the embodiment of the invention, the deacetylation degree of the chitosan or the derivative thereof is 55-95%.
According to an embodiment of the invention, the acid solution is selected from at least one of acetic acid, hydrochloric acid, sulfuric acid. The acid solution is preferably acetic acid, and a weak acidic environment can be provided by a small amount of acetic acid solution, and the dissolution of chitosan or the derivative thereof is promoted together with plant source acid; while the surface may be irritating to the skin when applied to the skin surface.
According to the embodiment of the invention, the plant source acid is added in the form of an aqueous solution, and the content of the plant source acid in the plant source acid aqueous solution is 1-3%.
According to an embodiment of the present invention, the content of the plant-derived acid in the composition is 0.5 to 1.5 times the content of the chitosan or the derivative thereof.
According to an embodiment of the invention, the antioxidant properties of the composition are significantly improved compared to the chitosan or derivatives thereof. The antioxidant properties of the provided compositions are significantly improved compared to chitosan or derivatives thereof alone. The noted significant improvement is referred to as p <0.05.
According to a second aspect of the present invention there is provided a method of preparing a composition comprising chitosan or a derivative thereof, comprising:
providing a plant source acid aqueous solution, wherein the plant source acid aqueous solution is obtained by dissolving plant source acid in water, and the content of the plant source acid in the plant source acid aqueous solution is 1-3%;
dispersing chitosan or its derivative in water, adding plant acid aqueous solution and acid solution under stirring, respectively, until no obvious particles of chitosan or its derivative are observed in the system, so as to obtain semisolid or liquid state composition containing chitosan or its derivative.
According to a third aspect of the present invention there is provided the use of a composition comprising chitosan or a derivative thereof as described in the first aspect or a composition comprising chitosan or a derivative thereof prepared according to the method of the second aspect in the antibacterial field.
According to an embodiment of the invention, the bacterium is escherichia coli or staphylococcus aureus.
The beneficial effects obtained by the invention are as follows:
according to the invention, plant sources such as tannic acid are introduced in the process of dissolving chitosan, so that the water solubility of chitosan is improved, meanwhile, the chitosan has remarkable inhibition effect on the growth of various pathogenic bacteria, particularly the antibacterial effect on escherichia coli and staphylococcus aureus can reach 98.26%, and the chitosan has better oxidation resistance compared with the chitosan or derivatives thereof. The main components of the composition provided are plant source acid, chitosan or derivatives thereof and a small amount of acid liquor, so that the composition has no irritation to skin and mucous membrane, and future products can be used for disinfecting and resisting skin wounds in multiple scenes and reduce the influence of microorganisms on wound healing.
Drawings
Fig. 1 is a statistical chart of DPPH radical scavenging rate provided in accordance with example 2 of the present invention.
Fig. 2 is a graph of the results of the IC50 value significance analysis provided in example 2 according to the present invention, where p < 0.01 is represented and p <0.05 is represented.
Fig. 3 is a graph showing the results of an antibacterial test against escherichia coli provided in example 3 according to the present invention.
Fig. 4 is a graph of an antibacterial test against staphylococcus aureus provided in example 4 according to the present invention.
Fig. 5 is a graph of a significance analysis of the bactericidal rates of chitosan and chitosan-tannic acid escherichia coli and staphylococcus aureus provided in examples 3 and 4 according to the invention, representing p <0.05.
FIG. 6 is a diagram showing an antibacterial test of chitosan-tannic acid with different deacetylations against E.coli according to example 5 of the present invention, wherein reference numeral 1 represents chitosan-tannic acid with a deacetylation degree of 50-55%; 2 represents chitosan-tannic acid with a deacetylation degree of 70-85%; 3 represents chitosan-tannic acid with deacetylation degree of 90-95%; * Represents p < 0.01.
Detailed Description
Reference will now be made in detail to embodiments of the present invention, examples of which are illustrated in the accompanying drawings. The embodiments described below by referring to the drawings are illustrative and intended to explain the present invention and should not be construed as limiting the invention.
Aiming at the problem that the solubility of chitosan in aqueous solution is poor and the antibacterial ability is affected, the invention provides a composition for enhancing the water solubility of chitosan and improving the antibacterial ability and the antioxidant ability of chitosan, and the provided composition can be prepared by a simple method, so that the solubility of chitosan and the antibacterial ability can be improved.
"plant-derived acids" as referred to herein are polyphenols derived from plant sources. The plant-derived acids mentioned include, but are not limited to, tannic acid, gallic acid, schisandra acid, and the like. According to a preferred embodiment, the mentioned plant-derived acids are in particular tannins, which have a phenolic hydroxyl structure that releases hydrogen ions in water, so that the solubility of chitosan is improved, and together with the acid solution, a weakly acidic environment is provided, which promotes the solubility of chitosan in weak acid conditions, and the antimicrobial capacity of the resulting composition is effectively improved.
The invention provides a composition containing chitosan or a derivative thereof, which comprises the following components in 100 parts by weight: 2.5-15 parts by weight of a plant source acid; 5-10 parts by weight of chitosan or a derivative thereof; 0.5 parts by weight of acid liquor; and the balance water; the composition is in a semi-solid or liquid state. The provided composition can improve the antibacterial property of chitosan. The plant source acid is added in the process of dissolving the chitosan, so that the solubility of the chitosan in a weak acid environment is enhanced, and meanwhile, the short-time antibacterial rate of escherichia coli and staphylococcus aureus reaches 98.26%; exhibits better oxidation resistance than chitosan. The provided composition has no irritation to skin and mucous membrane, and future products can be used for disinfection and antibiosis of multiple-scene skin wounds, and the influence of microorganisms on wound healing is reduced.
The chitosan or the derivative thereof in the composition is not limited to 20 ten thousand molecular weight chitosan, but also includes chitosan with various molecular weights. The chitosan related in the invention is not limited to chitosan with different molecular weights and different deacetylations, and also comprises chitosan derivatives modified by the chitosan in different modes, including but not limited to carboxymethyl chitosan, quaternary ammonium salt chitosan, carboxymethyl quaternary ammonium salt chitosan and the like. According to an embodiment, the mentioned chitosan or derivatives thereof have different degrees of deacetylation, which may be 55-95%. According to a specific embodiment, the degree of deacetylation of the chitosan or the derivative thereof may be 55 to 65%, for example, about 55%, 60%, 65%. According to a specific embodiment, the chitosan or the derivative thereof has a degree of deacetylation of 70 to 85%, for example, about 70%, about 75%, about 80% or about 85%. According to a specific embodiment, the degree of deacetylation of the chitosan or the derivative thereof is 90 to 95%, for example, 90%, 91%, 92%, 93%, 94%, 95%.
According to specific embodiments, the acid solution includes, but is not limited to, acetic acid, hydrochloric acid, sulfuric acid. According to the preferred embodiment, the acid liquid is acetic acid, the amount of acetic acid is large, the method is suitable for industrial production, the production of industrial waste liquid is reduced, a proper acidic environment can be provided, and the irritation to skin is small.
According to a specific embodiment, the plant source acid is added in the form of an aqueous solution, and the content of the plant source acid in the plant source acid aqueous solution is 1-3%. For example, it may be 1%, 2%, 3%, and too high a content of a plant-derived acid such as tannic acid may cause excessive crosslinking with chitosan or its derivatives, affecting solubility and bacteriostatic effects. The composition formed by the plant source acid and the chitosan or the derivative thereof in the content range can improve the antibacterial property of the chitosan and enhance the solubility of the chitosan in weak acid environment.
According to a specific embodiment, the content of the plant source acid in the composition is 0.5 to 1.5 times (for example, may be 0.5,1.0, or 1.5 times, etc.) the content of the chitosan or the derivative thereof, and is the most suitable mass ratio. The product formed by excessive crosslinking of the plant source acid with chitosan affects the bacteriostatic effect on microorganisms.
The invention also provides a preparation method of the composition containing chitosan or the derivative thereof, which comprises the following steps:
providing a plant source acid aqueous solution, wherein the plant source acid aqueous solution is obtained by dissolving plant source acid in water, and the content of the plant source acid in the plant source acid aqueous solution is 1-3%;
dispersing chitosan or its derivative in water, adding plant acid aqueous solution and acid solution under stirring, respectively, until no obvious particles of chitosan or its derivative are observed in the system, so as to obtain semisolid or liquid state composition containing chitosan or its derivative.
The preparation method provided by the invention does not need a heating process, and the semisolid or liquid composition containing chitosan or the derivative thereof can be obtained by stirring the mixture, so that the preparation method is simple in process and has the functions of antioxidation and antibiosis. According to a specific embodiment, the aqueous solution of plant-derived acid may be obtained under magnetic stirring. According to a specific embodiment, the aqueous solution of plant-derived acid and the acid solution may be added separately under magnetic stirring.
The invention also provides the use of the above-described composition comprising chitosan or a derivative thereof or a composition comprising chitosan or a derivative thereof prepared according to the method of the second aspect in the antibacterial field. It may be used for applications including but not limited to E.coli, or Staphylococcus aureus.
The following detailed description of the present invention is provided by way of specific examples, which should be construed as limiting the scope of the invention. The reagents or starting materials used in the examples were those commonly used in the art, and were obtained directly by purchase.
The tannic acid used was purchased from the scientific and technological company of carbofuran, beijing; chitosan was purchased from Shandong Fengtai Biotech Co.
Example 1
Example 1 a product comprising chitosan and tannic acid (chitosan-tannic acid) was obtained by the following method, comprising the steps of:
(1) Weighing a certain amount of vegetable tannic acid, and preparing into 1-3% aqueous solution, namely solution 1, under the condition of magnetic stirring;
(2) Preparing an acetic acid solution with a certain mass concentration, namely a solution 2;
(3) A certain amount of chitosan and derivatives with different molecular weights and deacetylation degree of about 90% are weighed and dispersed into double distilled water under the condition of magnetic stirring, and in the process, solution 1 and solution 2 are respectively added. When no obvious chitosan particles are seen by naked eyes in the system, the whole system is in a semisolid or liquid state.
The corresponding chitosan-tannic acid product is prepared and obtained. The pH value of the product is about 6.0 according to measurement.
Example 2
A certain amount of DPPH (commercially available from shanghai source leaf biotechnology limited) was weighed into absolute ethanol to prepare a DPPH standard solution having a mass concentration of 0.05 mg/mL. Respectively weighing a certain amount of ascorbic acid, chitosan and chitosan-tannic acid samples, dissolving the ascorbic acid, chitosan and chitosan-tannic acid samples by absolute ethyl alcohol or DMSO, and preparing sample solutions with mass concentration gradients of 0.5,1, 2, 2.5, 5, 10, 12.5 and 15 mg/mL, wherein the ascorbic acid is used as a positive control.
Accurately transferring 3.90 mL of DPPH use solution, respectively adding 100 μL of each sample solution with each concentration, developing for 30 min, taking absolute ethanol as blank control, and measuring absorbance A of each sample solution at 517 nm wavelength 1 . Meanwhile, the same amount of absolute ethyl alcohol is used for replacing a sample to be measured under the same condition, and the absorbance is recorded as A 0 3 times of parallel measurement, drawing a clearance curve, and calculating a radical half-inhibition rate IC according to the formula (1) 50 Values.
The results are shown in fig. 1, 2 and table 1. The experimental results show that: the positive control ascorbic acid shows a strong free radical scavenging efficiency, which is significantly higher than that of chitosan. The chitosan modified by tannic acid has obviously better free radical scavenging efficiency than chitosan, and the chitosan-tannic acid IC 50 The value was reduced by a factor of 1.36.
TABLE 1 DPPH radical scavenging Curve Linear analysis data sheet
Sample name | Fitting equation | R 2 | IC 50 (mg/mL) |
Ascorbic acid | y = 10.224x + 4.30 | 0.996 | 4.46 |
Chitosan | y = 6.001x - 0.2228 | 0.993 | 8.36 |
Chitosan-tannic acid | y = 7.332x + 3.4994 | 0.997 | 6.34 |
Example 3
The sterilized chitosan and chitosan-tannic acid are prepared into five solutions with different mass concentrations, and meanwhile, sterile water treatment is used as a reference, and according to the method and requirements for measuring the antibacterial/bacteriostatic action proposed in 2002 edition of national health Standard, the sterilization rate and the semi-lethal metering concentration (EC) of the chitosan and the chitosan-tannic acid on escherichia coli are tested and calculated by a carrier method and a suspension method respectively 50 mg/mL), the excellent bacterial growth is positively correlated with absorbance within a particular periphery.
The results are shown in fig. 3, 5 and table 2. Chitosan itself has NH 4 And a group exhibiting certain anti/bacteriostatic properties. The sterilization rate of the chitosan-tannic acid product is obviously better than that of chitosan in a fixed time, and the relative toxicity value of the chitosan-tannic acid is 1.75 times that of the chitosan.
TABLE 2 statistics of E.coli semi-lethal dose and relative virulence
Sample of | Fitting equation | R 2 | EC 50 (mg/mL) | Relative virulence |
Chitosan | y=0.4262x- 0.3199 | 0.995 | 5.6331 | 1.000 |
Chitosan-tannic acid | y=0.3445x- 0.2008 | 0.989 | 3.1305 | 1.791 |
Example 4
The sterilized chitosan and chitosan-tannic acid are prepared into five solutions with different mass concentrations, and meanwhile, sterile water treatment is used as a reference, according to the 2002 edition of national health Standard, the method and the requirement for measuring the antibacterial/bacteriostatic action are proposed, and the sterilization rate and the semi-lethal metering concentration (EC) of the chitosan, the chitosan-tannic acid to staphylococcus aureus are tested and calculated by a carrier method and a suspension method respectively 50 mg/mL), the excellent bacterial growth is positively correlated with absorbance within a particular periphery.
The results are shown in fig. 4, 5 and table 3. Chitosan itself has NH 4 And a group exhibiting certain anti/bacteriostatic properties. The sterilization rate of the chitosan product obtained by utilizing tannic acid modification is obviously better than that of chitosan in a fixed time,EC of chitosan 50 The value is 1.68 times that of chitosan tannic acid.
TABLE 3 statistics of semi-lethal dose and relative virulence of Staphylococcus aureus
Sample of | Fitting equation | R 2 | EC 50 (mg/mL) | Relative virulence |
Chitosan | y = 0.6462x-0.7071 | 0.986 | 12.4093 | 1.000 |
Chitosan-tannic acid | y = 0.3545x- 0.3142 | 0.989 | 7.3864 | 1.68 |
Example 5
Example 5 an antibacterial test of chitosan-tannic acid with different degrees of deacetylation against E.coli was studied. First, chitosan-tannins with different degrees of deacetylation were obtained by the procedure of example 1, wherein the tests were divided into three groups:
the deacetylation degree of the chitosan used in the group 1 is 50-55%;
the deacetylation degree of the chitosan used in the group 2 is 70-85%;
the chitosan used in group 3 has a degree of deacetylation of 90-95%.
The inhibitory effect of chitosan-tannic acid obtained by various methods on E.coli was compared, and the results are shown in FIG. 6. The test results show that: the higher the deacetylation degree of chitosan, the better the inhibition effect of the prepared chitosan-tannic acid on escherichia coli.
In the description of the present specification, a description referring to terms "one embodiment," "some embodiments," "examples," "specific examples," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms are not necessarily directed to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, the different embodiments or examples described in this specification and the features of the different embodiments or examples may be combined and combined by those skilled in the art without contradiction.
While embodiments of the present invention have been shown and described above, it will be understood that the above embodiments are illustrative and not to be construed as limiting the invention, and that variations, modifications, alternatives and variations may be made to the above embodiments by one of ordinary skill in the art within the scope of the invention.
Claims (10)
1. A composition comprising chitosan or a derivative thereof, characterized in that the composition comprises, on a 100 parts by weight basis:
2.5-15 parts by weight of plant source acid;
5-10 parts by weight of chitosan or a derivative thereof;
0.5 part by weight of acid liquor which is acetic acid; and
the balance of deionized water;
the composition is in a semi-solid or liquid state;
the pH value of the composition is 5.5-6.0.
2. The composition comprising chitosan or a derivative thereof according to claim 1, wherein the plant-derived acid is selected from at least one of tannic acid, gallic acid, schisandra acid.
3. The composition comprising chitosan or a derivative thereof according to claim 1, wherein the chitosan or a derivative thereof is selected from at least one of chitosan, carboxymethyl chitosan, quaternary ammonium salt chitosan, carboxymethyl quaternary ammonium salt chitosan.
4. The composition of claim 1, wherein the chitosan or derivative thereof has a degree of deacetylation of 55-95%.
5. The composition of claim 1, wherein the chitosan or derivative thereof has a degree of deacetylation of 90-95%.
6. The composition comprising chitosan or a derivative thereof according to claim 1, wherein the content of the plant-derived acid in the composition is 0.5 to 1.5 times the content of the chitosan or the derivative thereof.
7. The composition comprising chitosan or a derivative thereof according to claim 1, wherein the antioxidant properties of the composition are significantly improved compared to the chitosan or derivative thereof.
8. The method for producing a composition containing chitosan or a derivative thereof according to any one of claims 1 to 7, comprising:
providing a plant source acid aqueous solution, wherein the plant source acid aqueous solution is obtained by dissolving plant source acid in water, and the content of the plant source acid in the plant source acid aqueous solution is 1-3%;
dispersing chitosan or its derivative in water, adding plant acid aqueous solution and acid solution under stirring, respectively, until no obvious particles of chitosan or its derivative are observed in the system, so as to obtain the composition containing chitosan or its derivative in semisolid or liquid state.
9. Use of the composition comprising chitosan or a derivative thereof according to any one of claims 1 to 7 or the composition comprising chitosan or a derivative thereof prepared according to the method of claim 8 in the antibacterial field.
10. The use according to claim 9, wherein the bacterium is escherichia coli or staphylococcus aureus.
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101974102A (en) * | 2010-10-28 | 2011-02-16 | 浙江工业大学 | Novel water soluble chitosan derivative and preparation and application thereof |
US20110059162A1 (en) * | 2009-09-04 | 2011-03-10 | Jess Dreher Reed | Tannin-chitosan composites |
CN110227069A (en) * | 2019-06-20 | 2019-09-13 | 中国科学院海洋研究所 | A kind of pH response type tannic acid/chitosan nano capsule and preparation method thereof |
CN111588731A (en) * | 2019-02-21 | 2020-08-28 | 制药私人有限公司 | Composition for wound healing and its production method and use |
CN114129766A (en) * | 2021-12-13 | 2022-03-04 | 昆明理工大学 | Preparation method and application of nano-enzyme antibacterial hydrogel |
CN115651276A (en) * | 2022-09-29 | 2023-01-31 | 江苏省农业科学院 | Chitosan composite membrane containing protein nanoparticles and preparation method and application thereof |
-
2023
- 2023-05-18 CN CN202310560233.6A patent/CN116370498A/en active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110059162A1 (en) * | 2009-09-04 | 2011-03-10 | Jess Dreher Reed | Tannin-chitosan composites |
CN101974102A (en) * | 2010-10-28 | 2011-02-16 | 浙江工业大学 | Novel water soluble chitosan derivative and preparation and application thereof |
CN111588731A (en) * | 2019-02-21 | 2020-08-28 | 制药私人有限公司 | Composition for wound healing and its production method and use |
CN110227069A (en) * | 2019-06-20 | 2019-09-13 | 中国科学院海洋研究所 | A kind of pH response type tannic acid/chitosan nano capsule and preparation method thereof |
CN114129766A (en) * | 2021-12-13 | 2022-03-04 | 昆明理工大学 | Preparation method and application of nano-enzyme antibacterial hydrogel |
CN115651276A (en) * | 2022-09-29 | 2023-01-31 | 江苏省农业科学院 | Chitosan composite membrane containing protein nanoparticles and preparation method and application thereof |
Non-Patent Citations (2)
Title |
---|
刁羽佳: "多酚—壳聚糖缀合物的制备和应用", 河北工业大学, no. 3, 15 March 2022 (2022-03-15), pages 38 - 39 * |
胡飞等: "壳聚糖—多酚复合膜研究进展", 食品与机械, vol. 35, no. 6, 15 June 2019 (2019-06-15), pages 227 - 231 * |
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