CN109988317B - Amino acid modified lignin broad-spectrum antibacterial agent and preparation method and application thereof - Google Patents
Amino acid modified lignin broad-spectrum antibacterial agent and preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of natural polymer antibacterial agents, and discloses an amino acid modified lignin broad-spectrum antibacterial agent, and a preparation method and application thereof. The method comprises the following steps: adding 1-5 parts by weight of aldehyde and 1-5 parts by weight of amino acid into an alkaline solution containing 5-50 parts by weight of lignin, and heating at 40-120 ℃ for reaction for 1-6 hours to obtain the amino acid modified lignin broad-spectrum antibacterial agent. The invention also provides the amino acid modified lignin broad-spectrum antibacterial agent prepared by the method. According to the method, the lignin is modified by active amino acid components in the natural antibacterial peptide to obtain the amino acid modified lignin broad-spectrum antibacterial agent, so that the antibacterial activity of the lignin is effectively enhanced, the lignin has high antibacterial activity, and the antibacterial performance of the lignin is superior to that of the lignin; simultaneously has the inhibiting effect on both gram-positive bacteria and gram-negative bacteria and has broad-spectrum antibacterial property; and has low toxicity and good biocompatibility, and has great application prospect in the fields of biological medicine, food and cosmetics.
Description
Technical Field
The invention belongs to the technical field of natural polymer antibacterial agents, and particularly relates to an amino acid modified lignin broad-spectrum antibacterial agent and a preparation method and application thereof.
Background
Bacterial infections continue to be the leading cause of death worldwide. In order to prevent and control the high morbidity and mortality caused by bacterial infections, researchers have been working on developing highly effective antimicrobial materials/surfaces that are expected to be destroyed before the bacteria become dangerous.
Since 1923, the time that penicillin was discovered in alexanda fleming entered the antibiotic era. However, the unlimited use of antibiotics over the last century has severely reduced the efficacy of antibiotics. The phenomenon of bacterial resistance (AMR) has been increasing worldwide over the last 20 years. In 2014, a file describing the drug resistance of world bacteria compiled by the world health organization and member countries shows that the resistance of antibiotics to common bacteria is low to an amazing level, the public health safety is seriously threatened, and the development of novel antibacterial materials becomes an urgent need for preventing and treating bacterial pathogens.
The lignin is a natural high molecular polymer containing a polyphenol structure, has rich reserves, stable chemical properties and good biocompatibility, and can be applied to the fields of cosmetics, medicines and food health care. In recent years, lignin antibacterial materials have also been extensively studied. Guo et al compared the antibacterial activity of commercial water-soluble lignin with self-extracted water-insoluble lignin and found that the antibacterial effect of water-soluble lignin was significantly better than that of water-insoluble lignin (Applied Biochemistry and Biotechnology.184(1): 350-365). Dong et al (Industrial Crops and products.2011,34(3): 1629-. With the continuous development of nanotechnology, researchers use lignin, inorganic nano-metals and metal oxides thereof to prepare antibacterial materials in a blending mode, and find that the materials have certain inhibition effects on gram-positive bacteria and gram-negative bacteria (Food hydrocolloids.2017,7: 76-84). In addition, researches find that chemical modification can also effectively improve the antibacterial performance of lignin. Kaur et al prepared an antibacterial material by acetylating, epoxidizing, hydroxymethylating modified alkali lignin, found that the epoxidizing modified lignin had the best antibacterial effect, with MICs of 90 and 200mu g/disc for gram-positive (Bacillus) and gram-negative (Klebsiella) bacteria, respectively (Suger Tech.2017,19(6): 675-. Ma et al, an antibacterial film prepared by quaternizing the modified lignin and blending with polystyrene, because the presence of cationic quaternary ammonium salt has a significant inhibitory effect on gram-negative bacteria (E.coli) (Polymer.2017,114: 113-121).
In recent decades, natural antimicrobial peptides have been found to be widely found in nature, and they are part of the innate immune response to bacterial infections, and are composed primarily of lysine, arginine, and a proportion of hydrophobic residues. Unlike the metabolic effects of traditional antibiotics, antimicrobial peptides exert their antimicrobial activity by disrupting the cytoplasmic membrane, a mode of which can slow the emergence of bacterial resistance. However, the high toxicity, short circulating half-life (susceptible to protease hydrolysis) and high production cost of antimicrobial peptides limit their application.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention mainly aims to provide a preparation method of an amino acid modified lignin broad-spectrum antibacterial agent.
The natural polyphenol structure of the lignin enables the lignin to have certain antibacterial activity; meanwhile, the method of the invention utilizes the ortho position of the phenolic hydroxyl group in the phenylpropane skeleton of the lignin to generate Mannich reaction, and active amino acid in the natural antibacterial peptide is grafted to the lignin skeleton through the Mannich reaction, thereby improving the antibacterial activity of the lignin and expanding the antibacterial variety of the lignin; on the other hand, the main raw material lignin of the invention is derived from plants, the reserves are abundant, the biocompatibility is good, and the grafted lignin can reduce the toxicity and the cost.
The invention also aims to provide the amino acid modified lignin broad-spectrum antibacterial agent prepared by the method. The amino acid modified lignin broad-spectrum antibacterial agent has high antibacterial activity, has an inhibiting effect on gram-positive bacteria and gram-negative bacteria, and is low in toxicity and good in biocompatibility.
The invention also aims to provide the application of the amino acid modified lignin broad-spectrum antibacterial agent in the fields of biological medicines, foods and cosmetics; it has low toxicity, good biocompatibility and great application prospect.
The purpose of the invention is realized by the following scheme:
a preparation method of an amino acid modified lignin broad-spectrum antibacterial agent comprises the following steps:
adding 1-5 parts by weight of aldehyde and 1-5 parts by weight of amino acid into an alkaline solution containing 5-50 parts by weight of lignin, and heating at 40-120 ℃ for reaction for 1-6 hours to obtain the amino acid modified lignin broad-spectrum antibacterial agent.
In the method of the present invention, the aldehyde may be formaldehyde, dialdehyde, such as formaldehyde, glyoxal, malondialdehyde, succindialdehyde, glutaraldehyde, etc.; further preferred are dialdehydes with low toxicity such as glyoxal and the like.
In the method of the present invention, the amino acid may be at least one of lysine, threonine, leucine, methionine, tryptophan, phenylalanine, arginine, histidine, etc.; further preferred is at least one of basic amino acids such as lysine, arginine, histidine and the like.
In the method, the lignin can be at least one of solvent lignin, enzymatic lignin, alkali lignin, lignosulfonate and other industrial lignin.
The alkali lignin comprises wood pulp alkali lignin, bamboo pulp alkali lignin, wheat straw pulp alkali lignin, reed pulp alkali lignin, bark residue pulp alkali lignin, asparagus pulp alkali lignin, cotton pulp cedar alkali lignin and the like.
The lignosulfonate comprises bamboo pulp lignosulfonate, wheat straw pulp lignosulfonate, reed lignosulfonate, bark residue pulp lignosulfonate, asparagus pulp lignosulfonate, cotton pulp cedar lignosulfonate and the like.
The industrial lignin adopted by the invention is mainly derived from cooking wastewater in the paper-making and pulping industry, and the physical and chemical properties of the industrial lignin are greatly different according to different fiber raw materials, pulping processes, extraction methods and the like, so that the application of the industrial lignin is also very diversified.
Industrial lignin is generally divided into four categories: hydrolyzing lignin: hydrolyzed lignin is a residue obtained by saccharification with an acid, and is poor in solubility in water and solvents, poor in reactivity, and mostly condensed, and thus is frequently used as a fuel. Alkali lignin: the alkali lignin is mainly from waste liquid of alkaline pulping such as sulfate method and alkyl alkali method. ③ lignosulfonate: the lignosulfonate is derived from sulfite pulping waste liquor, and has good water solubility and wide application prospect. Fourthly, other lignin: solvent lignin, enzymatic lignin, and the like.
In the process of the invention, the concentration of lignin in the alkali solution may be 2.5-50 wt%.
To further better achieve the object of the present invention, the weight ratio of the lignin, the aldehyde and the amino acid is preferably 20:1:2 to 5:1: 6.
To further better achieve the object of the present invention, the temperature of the heating reaction is preferably controlled to be 60 to 100 ℃; the time is preferably controlled to be 2-4 h.
In the process of the present invention, the alkali solution is preferably an aqueous solution having a pH of 12-14.
In the method, the system after the heating reaction can obtain a purified product through neutralization, desalting and drying.
The neutralization means that the pH value of the system is adjusted to be 6-8.
The desalting can include dialysis with a dialysis bag with a cut-off of 2500Da, ultrafiltration with a filter membrane with a cut-off of 2500Da, or resin exchange with cation and anion exchange resin.
The invention also provides the amino acid modified lignin broad-spectrum antibacterial agent prepared by the method. The amino acid modified lignin broad-spectrum antibacterial agent has high antibacterial activity, better antibacterial performance than lignin, inhibition effect on gram-positive bacteria and gram-negative bacteria, low toxicity and good biocompatibility.
The invention also provides application of the amino acid modified lignin broad-spectrum antibacterial agent in the fields of biological medicines, foods and cosmetics. The lignin is a natural polyphenol polymer, has high oxidation resistance and light stability, is gathered with a large number of active oxygen clusters on the surface, and can release the active oxygen clusters when the lignin is contacted with bacteria to induce the bacteria to generate oxidative stress reaction, thereby changing the normal oxidation-reduction physiological process of the bacteria and leading the bacteria to die. Lignins are negatively charged and generally inhibit only gram-positive bacteria, while being inactive against gram-negative bacteria. Through modification of active amino acid components in the natural antibacterial peptide, the antibacterial activity of lignin can be enhanced, the lignin can inhibit gram-negative bacteria, the lignin has broad-spectrum antibacterial property, the application field of the natural high-molecular lignin is effectively expanded, and the lignin has a huge application prospect in the fields of biological medicines, foods and cosmetics.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. according to the invention, the active amino acid component in the natural antibacterial peptide is grafted to the natural lignin, so that the antibacterial activity of the lignin is enhanced, the antibacterial broad-spectrum property of the lignin is realized, and the antibacterial lignin has an inhibiting effect on gram-positive bacteria and gram-negative bacteria.
2. The lignin used by the invention is derived from plants, grows with human beings in a symbiotic way, has good biocompatibility, and the synthesized lignin broad-spectrum antibacterial agent not only keeps the active amino acid components in the natural antibacterial peptide, but also greatly reduces the toxicity of the antibacterial peptide, so that the lignin can be widely applied to the fields of biological medicines, foods and cosmetics.
3. The invention does not destroy the characteristics of lignin, such as ultraviolet resistance and oxidation resistance, so that the lignin can be used as a multifunctional antibacterial agent to be applied to the fields of biological medicines, foods and cosmetics.
4. The lignin and amino acid used by the invention have rich sources, low price, safety, no toxicity, greenness and environmental protection.
Drawings
FIG. 1 is a graph showing the antibacterial activity of the amino acid-modified lignin broad-spectrum antibacterial agent of example 1 against gram-positive Staphylococcus aureus.
FIG. 2 is a graph showing the antibacterial activity of the amino acid-modified lignin broad-spectrum antibacterial agent of example 1 against gram-negative Escherichia coli.
FIG. 3 is a cytotoxicity diagram of amino acid-modified lignin broad spectrum antibacterial agent of example 1.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
The materials referred to in the following examples are commercially available. Gram-positive bacteria (Staphylococcus aureus) and gram-negative bacteria (Escherichia coli), human keratinocytes HaCat cells used in the examples were purchased from Kyork, Guangdong, Inc.
Example 1
5 parts by weight of enzymatically hydrolyzed lignin were dissolved in 20 parts by weight of an aqueous sodium hydroxide solution having a pH of 14. Subsequently, 0.5 part by weight of glyoxal and 1.0 part by weight of arginine were added and heated to 60 ℃ with stirring. After reacting for 4 hours, adjusting the pH of the reaction solution to 7.5 by using hydrochloric acid, dialyzing to remove salt, and drying to obtain the amino acid modified lignin broad-spectrum antibacterial agent.
And testing the antibacterial activity of the prepared amino acid modified lignin broad-spectrum antibacterial agent. First, the antibacterial agent is dissolved in sterile water. Then, serial dilutions were made in 96-well plates with Muller-Hinton broth. Next, the bacterial suspension was cultured in Mueller-Hinton broth. Further serial dilutions were made in 96-well plates to final experimental concentrations. In addition, two control groups were set: (1) pure bacteria + culture fluid (lignin-free broad-spectrum antimicrobial agent) and (2) lignin broad-spectrum antimicrobial agent + culture fluid (bacteria-free). After incubation of all microtiter plates for 18h at 37 ℃ in a incubator, OD of the samples was measured with a Synergy Neo 2 microplate reader (Bio Tek, Germany)600The value is obtained. The concentration gradient of the lignin aqueous solution is 10-1000 mug/mL. The bacterial species shown are gram-positive bacteria (staphylococcus aureus) and gram-negative bacteria (escherichia coli). The experimental concentration of the bacterial suspension shown is 5X 105CFU/mL. Fig. 1 and fig. 2 are graphs showing the bacteriostatic activity of the amino acid-modified lignin broad-spectrum antibacterial agent prepared in this example on gram-positive bacteria and gram-negative bacteria. The lignin has certain activity on gram-positive staphylococcus aureus, and when the concentration of the lignin is 19g/L, 24 percent of staphylococcus aureus still survive; the antibacterial activity is further improved after the arginine is grafted, and when the concentration of the lignin antibacterial agent is 19g/L, staphylococcus aureus is basically inactivated; on the other hand, lignin has no inhibitory effect on gram-negative escherichia coli, the lignin is positively charged after the arginine is grafted by the method, good killing activity is also generated on the gram-negative escherichia coli, and when the concentration is 19g/L, the survival rate of the escherichia coli is less than 10%.
Testing the biocompatibility of the prepared amino acid modified lignin broad-spectrum antibacterial agent. Firstly, active human keratinocyte HaCat cells are inoculated on a 96-well plate, and LHC-9 culture solution is added for culturing for 24 hours. Then, the lignin was added to the above medium at various concentrations and incubated at 37 ℃. After 24h incubation, 100. mu.L of 5mg/mL 3- (4, 5-dimethylthiazol-2-yl) -2, 5-diphenyltetrazolium bromide (MTT) was added to each well and incubation continued for 4 h. Centrifuging to remove the culture solution, adding dimethyl sulfoxide, and testing the solution at OD with enzyme-labeling instrument570Absorbance of (b). FIG. 3 is a cytotoxicity diagram of the broad-spectrum lignin antibacterial agent prepared in the example. When the concentration of the amino acid modified lignin broad-spectrum antibacterial agent is as high as 20g/L, the cell survival rate still exceeds 80%, and good biocompatibility is shown.
Example 2
0.5 part by weight of alkali lignin was dissolved in 10 parts by weight of an aqueous sodium hydroxide solution having a pH of 14. Subsequently, 0.2 parts by weight of succinaldehyde and 1.2 parts by weight of histidine were added and heated to 80 ℃ with stirring. After reacting for 2h, regulating the pH of the reaction solution to 6 by hydrochloric acid, centrifuging, ultrafiltering, desalting, and drying to obtain the amino acid modified lignin broad-spectrum antibacterial agent.
The results of the tests are substantially the same as example 1, as determined by the same antibacterial test and cytotoxicity test as example 1.
Example 3
2 parts by weight of solvent-based lignin were dissolved in 15 parts by weight of an aqueous sodium hydroxide solution having a pH of 13. Subsequently, 0.5 parts by weight of formaldehyde and 1.5 parts by weight of lysine were added and heated to 50 ℃ with stirring. After reacting for 4 hours, adjusting the pH of the reaction solution to 7 by using hydrochloric acid, performing centrifugal ultrafiltration to remove salt, and drying to obtain the amino acid modified lignin broad-spectrum antibacterial agent.
The results of the tests are substantially the same as example 1, as determined by the same antibacterial test and cytotoxicity test as example 1.
Example 4
1 part by weight of lignosulfonate was dissolved in 15 parts by weight of aqueous sodium hydroxide solution having a pH of 13. Subsequently, 0.1 part by weight of formaldehyde and 0.5 part by weight of arginine were added and heated to 40 ℃ with stirring. After 8 hours of reaction, the pH value of the reaction solution is adjusted to 7 by hydrochloric acid, and the amino acid modified lignin broad-spectrum antibacterial agent is obtained by centrifugal ultrafiltration desalination and drying.
The results of the tests are substantially the same as example 1, as determined by the same antibacterial test and cytotoxicity test as example 1.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (7)
1. The amino acid modified lignin broad-spectrum antibacterial agent is characterized by being prepared by the following steps: adding 1-5 parts by weight of aldehyde and 1-5 parts by weight of amino acid into an alkaline solution containing 5-50 parts by weight of lignin, and heating at 40-120 ℃ for reaction for 1-6 hours to obtain an amino acid modified lignin broad-spectrum antibacterial agent;
the amino acid is at least one of basic amino acids lysine, arginine and histidine.
2. The amino acid modified lignin broad spectrum antibacterial agent of claim 1, wherein: the aldehyde is at least one of formaldehyde and dialdehyde.
3. The amino acid modified lignin broad spectrum antibacterial agent of claim 1, wherein: the lignin comprises at least one of solvent lignin, enzymatic lignin, alkali lignin and industrial lignin of lignosulfonate.
4. The amino acid-modified lignin broad-spectrum antibacterial agent according to claim 3, wherein the amino acid-modified lignin broad-spectrum antibacterial agent comprises: the alkali lignin comprises at least one of wood pulp alkali lignin, bamboo pulp alkali lignin, wheat straw pulp alkali lignin, reed pulp alkali lignin, bark residue pulp alkali lignin, asparagus pulp alkali lignin and cotton pulp cypress alkali lignin; the lignosulfonate comprises at least one of bamboo pulp lignosulfonate, wheat straw pulp lignosulfonate, reed lignosulfonate, bark residue pulp lignosulfonate, asparagus pulp lignosulfonate and cotton pulp cedar lignosulfonate.
5. The amino acid modified lignin broad spectrum antibacterial agent of claim 1, wherein: the concentration of lignin in the alkali solution is 2.5-50 wt%.
6. The amino acid modified lignin broad spectrum antibacterial agent of claim 1, wherein: the weight ratio of the lignin to the aldehyde to the amino acid is 20:1:2-5:1: 6; the temperature of the heating reaction is controlled to be 60-100 ℃; the time is controlled to be 2-4 h.
7. The use of the amino acid-modified lignin broad-spectrum antibacterial agent of claim 1 in the fields of biomedicine, food and cosmetics.
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| CN109988317B (en) * | 2019-03-20 | 2020-12-22 | 华南理工大学 | Amino acid modified lignin broad-spectrum antibacterial agent and preparation method and application thereof |
| CN112375231A (en) * | 2020-11-12 | 2021-02-19 | 齐鲁工业大学 | High-antibacterial-property modified nano lignin and preparation method and application thereof |
| CN112359638A (en) * | 2020-11-12 | 2021-02-12 | 齐鲁工业大学 | High-hydrophobicity antibacterial starch sized paper and preparation method thereof |
| CN112646197B (en) * | 2020-12-23 | 2023-02-21 | 浙江理工大学 | Aminated lignin and preparation method and application thereof |
| CN112772643B (en) * | 2020-12-23 | 2022-07-08 | 浙江理工大学 | Preparation method and application of stable high internal phase emulsion |
| CN112806433A (en) * | 2021-01-08 | 2021-05-18 | 安徽丰絮农业科技股份有限公司 | Sweet potato preservation method |
| CN113698623A (en) * | 2021-08-06 | 2021-11-26 | 江南大学 | High-biological-activity lignin and preparation method thereof |
| 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 |
| CN114177138B (en) * | 2021-12-03 | 2023-03-17 | 华南理工大学 | PH-responsive acetylated histidine modified lignin drug-loaded particle and preparation method thereof |
| CN114591514B (en) * | 2022-03-28 | 2023-04-28 | 浙江理工大学绍兴柯桥研究院有限公司 | Environment-friendly lignin-based dispersing agent for azo pigment and preparation method thereof |
| CN114982784B (en) * | 2022-05-24 | 2023-05-16 | 雅思汀娜（北京）科技有限公司 | Modified lignin antibacterial agent and antibacterial agent composition containing same |
| CN116120587B (en) * | 2023-02-02 | 2024-04-26 | 广东工业大学 | PH response lignin 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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