CN109988317A - A kind of amino-acid modified lignin broad spectrum antimicrobial agent and the preparation method and application thereof - Google Patents
A kind of amino-acid modified lignin broad spectrum antimicrobial agent and the preparation method and application thereof Download PDFInfo
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- CN109988317A CN109988317A CN201910210984.9A CN201910210984A CN109988317A CN 109988317 A CN109988317 A CN 109988317A CN 201910210984 A CN201910210984 A CN 201910210984A CN 109988317 A CN109988317 A CN 109988317A
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- lignin
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- antimicrobial agent
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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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
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
Abstract
The invention belongs to natural polymer antibacterial agent technical field, a kind of amino-acid modified lignin broad spectrum antimicrobial agent and the preparation method and application thereof is disclosed.The method of the present invention is added the aldehyde of 1-5 parts by weight and the amino acid of 1-5 parts by weight and obtains amino-acid modified lignin broad spectrum antimicrobial agent after 1-6h is reacted in 40-120 DEG C of heating the following steps are included: in the aqueous slkali of the lignin of parts by weight containing 5-50.The present invention also provides the amino-acid modified lignin broad spectrum antimicrobial agents that the above method is prepared.The method of the present invention obtains amino-acid modified lignin broad spectrum antimicrobial agent by active amino acid component lignin in natural antibacterial peptide, effectively enhances the antibacterial activity of lignin, makes it have high antibacterial activity, and anti-microbial property is better than lignin；Inhibiting effect is all had to gram-positive bacteria and negative bacterium simultaneously, there is broad spectrum antibacterial；And toxicity is low, good biocompatibility, has huge application prospect in biological medicine, foods and cosmetics field.
Description
Technical field
The invention belongs to natural polymer antibacterial agent technical field, in particular to a kind of amino-acid modified lignin wide spectrum is anti-
Microbial inoculum and the preparation method and application thereof.
Background technique
In worldwide, bacterium infection remains the main reason for leading to death.In order to prevent and control because of bacterium
High incidence and high mortality caused by infection, researcher have been devoted to develop efficient anti-biotic material/surface, it is expected that
It can be eliminated before bacterium becomes danger.
After Alexandria Fleming has found penicillin, the antibiotic epoch are entered from nineteen twenty-three.However, nearly one
Century weakens the drug effect of antibiotic seriously using antibiotic without restriction.In past 20 years, bacterial drug resistance
(AMR) the phenomenon that, is all constantly rising all over the world.2014, a description generation of the World Health Organization and member state's establishment
The file of boundary's bacterial resistance implementations show antibiotic to the resistance of common bacteria as low as surprising level, serious prestige
Coerced public health security, exploitation novel antibacterial material have become prevention and treatment bacterial pathogen there is an urgent need to.
Lignin is a kind of natural polymers containing polyphenol structure, and rich reserves, chemical property is stablized, raw
Object is compatible good, can be applied to cosmetics, medicine and field of food health care.In recent years, lignin anti-biotic material is also widely studied.
Guo et al. investigation and comparison commercial water-soluble lignin and the antibacterial activity for picking up by oneself negated water-soluble lignin, discovery are water-soluble
Lignin antibacterial effect is substantially better than water-insoluble lignin (Applied Biochemistry and
Biotechnology.184(1):350-365).Dong et al. (Industrial Crops and Products.2011,34
(3): 1629-1634) increase water solubility of the lignin in culture solution by adding 5%DMSO in culture solution, minimum is anti-
Bacteria concentration (MIC) reaches 1.25mg/mL, is better than commercial water-soluble lignin (MIC=2.5mg/mL), but because lignin is whole
In elecrtonegativity, there is no insect killing effect to Gram-negative bacteria.With the continuous development of nanotechnology, researcher utilizes lignin
It is blended with inorganic nano metal and its metal oxide and prepares anti-biotic material, it is found that such material is blue to gram-positive bacteria and leather
Family name's negative bacterium is provided with certain inhibitory effect (Food Hydrocolloids.2017,7:76-84).In addition, research discoveryization
Lignin anti-microbial property can also be effectively improved by learning modification.Kaur et al. is wooden by acetylation, epoxidation, the modified alkali of methylolation
Element prepares anti-biotic material, it is found that the antibacterial effect of epoxidation modification lignin is best, to gram-positive bacteria (bacillus) and
The MIC of Gram-negative bacteria (Klebsiella) be respectively 90 and 200mu g/disc (Suger Tech.2017,19 (6):
675-680).Antibacterial film of the Ma et al. by quaternised modified lignin and with polystyrene blend preparation, because of cationic season
The presence of ammonium salt has obvious inhibiting effect (Polymer.2017,114:113-121) to Gram-negative bacteria (Escherichia coli).
In recent decades, it has been found that natural antibacterial peptide is widespread in nature, and it is congenital that they belong to bacterium infection
A part of immune response is mainly made of lysine, arginine and a certain proportion of hydrophobic residue.Different from traditional antibiosis
The metabolism of element, antibacterial peptide play its antibacterial activity by destroying cytoplasma membrane, and this antibacterial activity mode can slow down carefully
The appearance of bacterium drug resistance.However, the high toxicity of antibacterial peptide, short circulating half-life (vulnerable to protease hydrolytic) and height are produced into
This, limits its application.
Summary of the invention
In order to overcome the shortcomings and deficiencies of the prior art described above, change the primary purpose of the present invention is that providing a kind of amino acid
The preparation method of property lignin broad spectrum antimicrobial agent.
The natural polyphenol structure of lignin makes it have certain antibacterial activity；Meanwhile the method for the present invention utilizes lignin
Phenylpropyl alcohol alkane skeleton in the ortho position of phenolic hydroxyl group Mannich reaction can occur, by Mannich reaction by the work in natural antibacterial peptide
Acidic amino acid is grafted on lignin skeleton, is improved the antibacterial activity of lignin and is expanded its antibacterial type；On the other hand, this hair
Bright primary raw material lignin derives from plant, and rich reserves, good biocompatibility, toxicity can both be reduced by being grafted lignin,
It can also be with cost declining.
Another object of the present invention is to provide the amino-acid modified lignin broad spectrum antimicrobial agent that the above method is prepared.This
The amino-acid modified lignin broad spectrum antimicrobial agent of invention has high antibacterial activity, has inhibition to gram-positive bacteria and negative bacterium
Effect, while toxicity is low, good biocompatibility.
Still a further object of the present invention be to provide above-mentioned amino-acid modified lignin broad spectrum antimicrobial agent biological medicine, food and
Application in cosmetic field；Its toxicity is low, good biocompatibility, there is huge application prospect.
The purpose of the present invention is realized by following proposal:
A kind of preparation method of amino-acid modified lignin broad spectrum antimicrobial agent, comprising the following steps:
In the aqueous slkali of the lignin of parts by weight containing 5-50, the aldehyde of 1-5 parts by weight and the amino acid of 1-5 parts by weight, 40- is added
After 120 DEG C of heating reaction 1-6h, amino-acid modified lignin broad spectrum antimicrobial agent is obtained.
In the method for the present invention, it such as includes formaldehyde, glyoxal, malonaldehyde, butanedial, penta that the aldehyde, which can be formaldehyde, dialdehyde,
Dialdehyde etc.；Further preferably hypotoxicity dialdehyde such as glyoxal etc..
In the method for the present invention, the amino acid can be lysine, threonine, leucine, methionine, tryptophan, phenylpropyl alcohol
At least one of propylhomoserin, arginine, histidine etc.；Further preferably basic amino acid such as lysine, arginine and group ammonia
At least one of acid etc..
In the method for the present invention, the lignin can be organosolv lignin, enzymolysis xylogen, alkali lignin and wooden
At least one of industrial lignins such as plain sulfonate.
The alkali lignin includes wood pulp alkali lignin, bamboo pulp alkali lignin, Straw Pulp alkali lignin, reed pulp alkali wood
Quality, skin slurry alkali lignin, Dracaena straw pulp alkali lignin, cotton pulp cypress alkali lignin etc..
The lignosulfonates include bamboo pulp lignosulfonates, Straw Pulp lignosulfonates, reed lignin
Sulfonate, skin slurry lignosulfonates, Dracaena straw pulp lignosulfonates, cotton pulp cypress mahogany sulfonate etc..
The industrial lignin that the present invention uses is mainly derived from the waste water from cooking of paper-making pulping industry, according to fibrous raw material,
The difference of pulping process and extracting method etc., their physicochemical properties differ greatly, therefore its application is also very more
Sample.
Industrial lignin is generally divided into four classes: 1. hydrolytic lignin: hydrolytic lignin obtains after being saccharified with acid
Residue, it is all very poor to the dissolubility of water and solvent, and reactivity worth is also very poor, largely has occurred and that condensation, therefore multi-purpose work
Fuel.2. alkali lignin: alkali lignin mostlys come from the alkaline pulp black liquors such as sulfate process, alkane alkaline process.3. lignin sulfonic acid
Salt: lignosulfonates have water-soluble and broad application prospect well from spentsulfiteliquor.4. its
His lignin: organosolv lignin, enzymolysis xylogen etc..
In the method for the present invention, the concentration of lignin can be 2.5-50wt% in the aqueous slkali.
For the object of the invention is further better achieved, the weight ratio of the lignin, aldehyde and amino acid is preferably 20:1:
2-5:1:6。
For the object of the invention is further better achieved, the temperature of the heating reaction is preferably controlled in 60-100 DEG C；When
Between be preferably controlled in 2-4h.
In the method for the present invention, the aqueous slkali is preferably the aqueous solution of pH12-14.
In the method for the present invention, system can be by neutralization, desalination, drying after heating reaction, the product that is purified.
The neutralization refers to that regulation system pH is 6-8.
The desalination may include being dialysed using the bag filter of molecular cut off 2500Da, or utilize molecular cut off 2500Da
Ultrafiltration through membranes, or cross zwitterion resin.
The present invention also provides the amino-acid modified lignin broad spectrum antimicrobial agents that the above method is prepared.Amino of the invention
Sour modified lignin resin broad spectrum antimicrobial agent has high antibacterial activity, and anti-microbial property is better than lignin, at the same to gram-positive bacteria and
Negative bacterium is inhibited, and toxicity is low, good biocompatibility.
The present invention also provides above-mentioned amino-acid modified lignin broad spectrum antimicrobial agents in biological medicine, foods and cosmetics field
In application.Lignin is natural polyphenol polymer, inoxidizability and photostability with higher, surface aggregation it is a large amount of
Reactive oxygen species can discharge reactive oxygen species when lignin is contacted with bacterium, and response to oxidative stress occurs for Induction of bacterial, to change
The normal redox physiology course of bacterium and it is dead.Lignin is negatively charged, general only to inhibit gram-positive bacteria, blue for leather
Family name's negative bacterium is without activity.By active amino acid component in natural antibacterial peptide, the antibacterial of lignin not only can be enhanced
Activity can also make lignin inhibit Gram-negative bacteria, so that lignin is had broad spectrum antibacterial, effectively expanded natural polymer
The application field of sub- lignin has huge application prospect in biological medicine, foods and cosmetics field.
The present invention compared with the existing technology, have the following advantages and the utility model has the advantages that
1, the active amino acid constituents in natural antibacterial peptide is grafted in natural lignin by the present invention, has both been enhanced wooden
The antibacterial activity of element, also achieves the broad spectrum activity of lignin antibacterial, has inhibiting effect to Gram-positive and negative bacteria.
2, the lignin that uses of the present invention is grown, good biocompatibility altogether from plant with mankind's symbiosis, synthesis it is wooden
Plain broad spectrum antimicrobial agent had both maintained active amino acid constituents in natural antibacterial peptide, has been greatly reduced the toxicity of antibacterial peptide, has made it
It can be widely applied to biological medicine, foods and cosmetics field.
3, the present invention does not destroy lignin self character makes it can be used as one kind more such as UV resistance and antioxygenic property
Function antibacterial agent is applied in biological medicine, foods and cosmetics field.
4, the lignin and origin of amino acid that the present invention uses are abundant, cheap, safe and non-toxic, environmentally protective.
Detailed description of the invention
Fig. 1 is that the amino-acid modified lignin broad spectrum antimicrobial agent of embodiment 1 is staphylococcic to Gram-positive S
Antibacterial activity figure.
Fig. 2 is that the amino-acid modified lignin broad spectrum antimicrobial agent of embodiment 1 is living to the antibacterial of Gram-E. coli
Property figure.
Fig. 3 is the cytotoxicity figure of the amino-acid modified lignin broad spectrum antimicrobial agent of embodiment 1.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, and embodiments of the present invention are not limited thereto.
Material involved in the following example can be obtained from commercial channel.Gram-positive bacterium used in embodiment
(staphylococcus aureus) and gramnegative bacterium (Escherichia coli), human keratinous formation cell HaCat cell are purchased from
Huankai Microbes Tech Co., Ltd., Guangdong.
Embodiment 1
5 parts by weight enzymolysis xylogens are dissolved in 20 parts by weight pH=14 sodium hydrate aqueous solutions.Then, 0.5 weight is added
The glyoxal and 1.0 parts by weight arginine for measuring part, are heated to 60 DEG C under stiring.After reacting 4h, with hydrochloric acid by reaction solution pH tune
For section to 7.5, desalination of dialysing is dried to obtain amino-acid modified lignin broad spectrum antimicrobial agent.
Test the antibacterial activity for the amino-acid modified lignin broad spectrum antimicrobial agent being prepared.Firstly, antibacterial agent is dissolved
In sterile water.Then, with the serial dilution in 96 orifice plates of Muller-Hinton meat soup.Secondly, in Mueller-Hinton meat
Bacterial suspension is cultivated in soup.Further serial dilution is to final experimental concentration in 96 orifice plates.In addition, two groups of control groups of setting:
(1) pure bacterium+culture solution (no lignin broad spectrum antimicrobial agent) and (2) lignin broad spectrum antimicrobial agent+culture solution (no bacterium).It is all
After microtiter plate cultivates 18h in 37 DEG C of insulating boxs, with 2 microplate reader of Synergy Neo (Bio Tek, Germany) measurement sample
OD600Value.The lignin concentration of aqueous solution gradient is 10-1000 μ g/mL.Shown in bacterial species be Gram-positive
Bacterium (staphylococcus aureus) and gramnegative bacterium (Escherichia coli).Shown in bacterial suspension experimental concentration be 5 ×
105CFU/mL.Fig. 1 and Fig. 2 be amino-acid modified lignin broad spectrum antimicrobial agent manufactured in the present embodiment to gram-positive bacteria and
The bacteriostatic activity figure of Gram-negative bacteria.Lignin has certain activity to Gram-positive S staphylococcus itself,
When lignin concentration is 19g/L, still there is 24% staphylococcus aureus survival；And antibacterial is living after the present invention is grafted arginine
Property further promoted, lignin antimicrobial agent concentration be 19g/L when, staphylococcus aureus inactivates substantially；On the other hand, lignin
Originally there is no inhibiting effect to Gram-E. coli, lignin is positively charged after the present invention is grafted arginine, blue to leather
Family name's negative bacterium also produces good virulence, when concentration is 19g/L, Escherichia coli survival rate < 10%.
Test the biocompatibility for the amino-acid modified lignin broad spectrum antimicrobial agent being prepared.Firstly, by active human
The culture of LHC-9 culture solution is added for 24 hours on 96 orifice plates in keratinocyte HaCat cell inoculation.Then by the upper of various concentration
It states lignin to be added in above-mentioned culture medium, be incubated at 37 DEG C.After culture for 24 hours, by 3- (4, the 5- dimethyl of 100 μ L 5mg/mL
Thiazol-2-yl) -2,5- diphenyltetrazolium bromide (MTT) is added in each hole, continue constant temperature incubation 4h.It is centrifuged off culture
Dimethyl sulfoxide is added in liquid, using microplate reader test solution in OD570Absorbance.Fig. 3 is that the lignin of embodiment preparation is wide
Compose the cytotoxicity figure of antibacterial agent.For amino-acid modified lignin broad spectrum antimicrobial agent when at concentrations up to 20g/L, cell survival rate is still
More than 80%, good biocompatibility is shown.
Embodiment 2
0.5 parts by weight alkali lignin is dissolved in 10 parts by weight pH=14 sodium hydrate aqueous solutions.Then, 0.2 weight is added
The butanedial and 1.2 parts by weight histidines for measuring part, are heated to 80 DEG C under stiring.After reacting 2h, with hydrochloric acid by reaction solution pH tune
For section to 6, centrifugal ultrafiltration desalination is dried to obtain amino-acid modified lignin broad spectrum antimicrobial agent.
It is measured using antibacterial experiment same as Example 1 and cytotoxicity experiment, experimental result and the basic phase of embodiment 1
Together.
Embodiment 3
2 parts by weight solvent type lignin are dissolved in 15 parts by weight pH=13 sodium hydrate aqueous solutions.Then, it is added 0.5
The formaldehyde of parts by weight and 1.5 parts by weight lysines, are heated to 50 DEG C under stiring.After reacting 4h, with hydrochloric acid by reaction solution pH tune
For section to 7, centrifugal ultrafiltration desalination is dried to obtain amino-acid modified lignin broad spectrum antimicrobial agent.
It is measured using antibacterial experiment same as Example 1 and cytotoxicity experiment, experimental result and the basic phase of embodiment 1
Together.
Embodiment 4
1 parts by weight lignosulfonates are dissolved in 15 parts by weight pH=13 sodium hydrate aqueous solutions.Then, it is added 0.1
The formaldehyde of parts by weight and 0.5 parts by weight arginine, are heated to 40 DEG C under stiring.After reacting 8h, with hydrochloric acid by reaction solution pH tune
For section to 7, centrifugal ultrafiltration desalination is dried to obtain amino-acid modified lignin broad spectrum antimicrobial agent.
It is measured using antibacterial experiment same as Example 1 and cytotoxicity experiment, experimental result and the basic phase of embodiment 1
Together.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (10)
1. a kind of preparation method of amino-acid modified lignin broad spectrum antimicrobial agent, it is characterised in that the following steps are included: containing 5-50
In the aqueous slkali of parts by weight lignin, the aldehyde of 1-5 parts by weight and the amino acid of 1-5 parts by weight, 40-120 DEG C of heating reaction is added
After 1-6h, amino-acid modified lignin broad spectrum antimicrobial agent is obtained.
2. the preparation method of amino-acid modified lignin broad spectrum antimicrobial agent according to claim 1, it is characterised in that: described
Amino acid be lysine, threonine, leucine, methionine, tryptophan, phenylalanine, arginine, at least one in histidine
Kind.
3. the preparation method of amino-acid modified lignin broad spectrum antimicrobial agent according to claim 1, it is characterised in that: described
Amino acid be at least one of basic amino acids lysine, arginine and histidine.
4. the preparation method of amino-acid modified lignin broad spectrum antimicrobial agent according to claim 1, it is characterised in that: described
Aldehyde be at least one of formaldehyde and dialdehyde.
5. the preparation method of amino-acid modified lignin broad spectrum antimicrobial agent according to claim 1, it is characterised in that: described
Lignin include in the industrial lignin of organosolv lignin, enzymolysis xylogen, alkali lignin and lignosulfonates
It is at least one.
6. the preparation method of amino-acid modified lignin broad spectrum antimicrobial agent according to claim 5, it is characterised in that: described
Alkali lignin include wood pulp alkali lignin, bamboo pulp alkali lignin, Straw Pulp alkali lignin, reed pulp alkali lignin, skin slurry
At least one of alkali lignin, Dracaena straw pulp alkali lignin and cotton pulp cypress alkali lignin；The lignosulfonates include
Bamboo pulp lignosulfonates, Straw Pulp lignosulfonates, reed lignin sulfonate, skin slurry lignosulfonates, Dracaena
At least one of straw pulp lignosulfonates and cotton pulp cypress mahogany sulfonate.
7. the preparation method of amino-acid modified lignin broad spectrum antimicrobial agent according to claim 1, it is characterised in that: described
The concentration of lignin is 2.5-50wt% in aqueous slkali.
8. the preparation method of amino-acid modified lignin broad spectrum antimicrobial agent according to claim 1, it is characterised in that: described
The weight ratio of lignin, aldehyde and amino acid is 20:1:2-5:1:6；The temperature of the heating reaction is controlled at 60-100 DEG C；Time
Control is in 2-4h.
9. a kind of amino-acid modified lignin broad spectrum antimicrobial agent, it is characterised in that system according to claim 1-8
Preparation Method obtains.
10. amino-acid modified lignin broad spectrum antimicrobial agent as claimed in claim 9 is in biological medicine, foods and cosmetics field
Application.
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| PCT/CN2019/117839 WO2020186784A1 (en) | 2019-03-20 | 2019-11-13 | Amino acid modified lignin broad-spectrum antibacterial agent and preparation method and application thereof |
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| CN113912864B (en) * | 2021-10-26 | 2022-08-16 | 华南理工大学 | Mussel foot protein-imitated modified lignin adhesion enhancing material and preparation method and application thereof |
| CN113912864A (en) * | 2021-10-26 | 2022-01-11 | 华南理工大学 | Mussel foot protein-imitated modified lignin adhesion enhancing material and preparation method and application thereof |
| CN114177138A (en) * | 2021-12-03 | 2022-03-15 | 华南理工大学 | PH-responsive acetylated histidine modified lignin drug-loaded particle and preparation method thereof |
| CN114591514A (en) * | 2022-03-28 | 2022-06-07 | 浙江理工大学绍兴柯桥研究院有限公司 | Environment-friendly lignin-based dispersant for azo pigment and preparation method thereof |
| CN114982784A (en) * | 2022-05-24 | 2022-09-02 | 雅思汀娜（北京）科技有限公司 | Modified lignin antibacterial agent and antibacterial agent composition containing same |
| CN116120587A (en) * | 2023-02-02 | 2023-05-16 | 广东工业大学 | PH response lignin and preparation method and application thereof |
| CN116120587B (en) * | 2023-02-02 | 2024-04-26 | 广东工业大学 | PH response lignin and preparation method and application thereof |
| CN116239792A (en) * | 2023-02-15 | 2023-06-09 | 广东省科学院微生物研究所(广东省微生物分析检测中心) | Medium-chain amino lignin antibacterial agent and preparation method and application thereof |
| CN116239792B (en) * | 2023-02-15 | 2024-04-23 | 广东省科学院微生物研究所(广东省微生物分析检测中心) | Medium-chain amino lignin antibacterial agent and preparation method and application thereof |
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| CN109988317B (en) | 2020-12-22 |
| WO2020186784A1 (en) | 2020-09-24 |
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