CN106117392A - A kind of chitosan graft vanilloyl derivant and its preparation method and application - Google Patents
A kind of chitosan graft vanilloyl derivant and its preparation method and application Download PDFInfo
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- CN106117392A CN106117392A CN201610599981.5A CN201610599981A CN106117392A CN 106117392 A CN106117392 A CN 106117392A CN 201610599981 A CN201610599981 A CN 201610599981A CN 106117392 A CN106117392 A CN 106117392A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
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Abstract
The invention discloses a kind of chitosan graft vanilloyl derivant and its preparation method and application.The present invention, with vanillic acid as raw material, is reacted with thionyl chloride by vanillic acid and is prepared as aroyl chloride；The amido protecting product N phthalyl chitosan of chitosan; first with aroyl chloride generation nucleophilic substitution; generating acylate 2 N phthalyl 6 O vanilloyl chitosan, product is sloughed amido protecting in hydrazine hydrate solution and is prepared into product 6 O vanilloyl chitosan.Gained target product also retains the active amine groups of chitosan while introducing vanilloyl, improves the original physicochemical property of chitosan, improves dissolubility；Improve biological activity simultaneously, expand antimicrobial spectrum, enhance antibacterial activity, these will expand its range of application.
Description
Technical field
The present invention relates to antibacterial technology, be specifically related to a kind of chitosan graft vanilloyl derivant and preparation method thereof
And application.
Background technology
Along with improving constantly of expanding economy and living standards of the people, people's health consciousness constantly strengthens, food safety
The highest attention of the public has been caused with problem of environmental pollution.It is chemical pesticide due to be agriculturally used mostly at present, because of pesticide
Food safety and problem of environmental pollution that residual causes become increasingly conspicuous, and harmful pesticide residues have had a strong impact on the sustainable development of agricultural
Exhibition and human health.Therefore, cry efficient, low toxicity, low-residual biological pesticide is developed more and more higher.
China is a large agricultural country, simultaneously Ye Shiyige ocean big country, utilizes abundant living marine resources, and exploitation is new
Type marine organisms source pesticide, is a new research field having a extensive future.Chitin is derived from shrimp, Eriocheir sinensis, insecticide etc.
Arthropodan shell or molluscan shell and fungus, the cell wall of lower algae.Chitin content enriches, and is content
It is only second to the second largest natural biological polysaccharide of cellulose.Chitosan, as the deacetylated product of chitin, has nontoxic, biofacies
Capacitive is good, can the feature such as natural degradation.Chitosan can suppress plant pathogenic fungi and induction plant to produce disease resistance, with shell
Polysaccharide, oligochitosan are that the existing multiple products of marine organisms source pesticide of raw material development appear on the market.
Chitosan and oligosaccharide preparation generally exist that antibacterial activity is low and the deficiency of the aspect such as poorly water-soluble, by chitosan
Carry out the means such as locator qualification, graft copolymerization, click chemistry and carry out chemical modification, import antibacterial activity group, it is possible to obtain tool
There is the chitosan derivative of relatively high antibacterial activity.Aromatic substance in plant, a portion activity comes from fragrance
Acid, it is widely present in plant, and particularly in plants essential oil, many natural carboxylic acids are pharmaceutically being commonly used for medicine intermediate；With
Time aromatic carboxylic acids there is good antibacterial activity more, various pathogenic bacteria is all shown certain inhibition.
Summary of the invention
Not enough in order to solve prior art, the invention provides a kind of chitosan graft vanilloyl derivant and preparation thereof
Methods and applications.
The technical scheme is that a kind of chitosan graft vanilloyl derivant, its structure such as formula I, wherein R is Rhizoma et radix valerianae
Acyl group, the structure of its acid is shown in Formula II；N is the degree of polymerization >=2；
Another object of the present invention is to provide the preparation method of a kind of chitosan graft vanilloyl derivant, by inciting somebody to action
The amido protecting thing of vanilloyl and chitosan reacts and is prepared.
Described method, Rhizoma et radix valerianae acyl chlorides generates with the amido protecting product N-phthalyl chitosan reaction of chitosan
2-N-phthalyl-6-O-vanilloyl chitosan, product is sloughed phthalyl in hydrazine hydrate solution and is obtained 6-O-perfume
Oxalyl chitosan.
Described method, the amido protecting of described chitosan uses and generates N-phthalyl with phthalic anhydride
Base enclosure polysaccharide；Wherein the chitosan molecule degree of polymerization is not less than 2, deacetylation >=80%.
Described method, the preparation of described vanilloyl chlorine is with vanillic acid as raw material, with dichloromethane as solvent, dropping
The thionyl chloride of 3～10 times of equivalents, in 40 DEG C of back flow reaction, monitors reaction process by thin layer chromatography, and product decompression is steamed
Evaporate, obtain Rhizoma et radix valerianae acyl chlorides.If raw material is vanillin or cephrol palpus initial oxidation generation vanillic acid.
Described method, the amido protecting of chitosan is with chitosan as raw material, in aqueous DMF
Swelling dispersion, add about 3 times of equivalents phthalic anhydride, 120 DEG C be stirred at reflux 8h after be cooled to room temperature, product pours into ice
In water, filtration under diminished pressure with distilled water wash, after filtration, product is scattered in ethanol fully wash, be centrifuged, lyophilization obtains
To N-phthalyl chitosan.
Described method, is scattered in N-phthalyl chitosan in DMF, stirs at 60 DEG C
Mix swelling 30min, after temperature is down to room temperature, is added dropwise over the DMF solution containing excess vanilloyl chlorine, in
10h is reacted at 35 DEG C.Reactant liquor is poured in 4 times amount dehydrated alcohol, precipitates 1h in 4 DEG C, be centrifuged 3 times with absolute ethanol washing,
Lyophilization obtains light brown product, is acylate 2-N-phthalyl-6-O-vanilloyl chitosan.
Described method, takes described 2-N-phthalyl-6-O-vanilloyl chitosan and adds the pyrrole of equal-volume mixing
In pyridine and hydrazine hydrate, 80 DEG C of backflow 6h, reactant liquor pours in 4 times of volume dehydrated alcohol and precipitates, and centrifugal, solid ethanol is fully washed
Washing, low temperature is frozen into solid, last lyophilization, obtains khaki powdered product, i.e. 6-O-vanilloyl chitosan.
Another object of the present invention is to provide chitosan graft vanilloyl derivant in preparing water base antibacterial
Application.
Invention further provides chitosan graft vanilloyl derivant at preparation suppression botrytis cinerea, Semen Tritici aestivi
Application in gibberellic hypha, P. capsici or rhizoctonia cerealis medicine.
The present invention proposes to access in chitosan molecule using vanillic acid as active group, maintains chitosan to spread out to the full extent
Produce the active group of thing, make chitosan produce synergism with antibacterial activity group, enable synthetic keep shell to gather simultaneously
Nontoxic, the degradable and feature of good biocompatibility of sugar, lays the foundation for development of new marine organisms pesticide.The present invention is with Rhizoma et radix valerianae
Acid is raw material, is prepared as aroyl chloride by reacting with thionyl chloride；The amido protecting product N-O-phthalic of chitosan
Acyl chitosan, first with aroyl chloride generation nucleophilic substitution, generates acylate 2-N-phthalyl-6-O-
Vanilloyl chitosan, product is sloughed amido protecting in hydrazine hydrate solution and is prepared into product 6-O-vanilloyl chitosan.Gained mesh
Mark product also retains the active amine groups of chitosan while introducing vanilloyl, changes the original physics and chemistry of chitosan
Matter, improves dissolubility；Improving the biological activity of chitosan simultaneously, expand antimicrobial spectrum, strengthen antibacterial activity, these will expand it
Range of application.
Have the feature that of the present invention:
1. after the present invention introduces aromatic acid active structure in chitosan structure, can improve chitosan water dissolution performance and
Biological activity to microorganism.
2. the chitosan graft vanilloyl derivant that prepared by the present invention has good water solublity and antibacterial activity, overcomes
The shortcoming of chitosan self water-soluble difference, has expanded its application, has led at disinfectant use in agriculture, veterinary drug, medicine, cosmetics etc.
There is potential using value in territory.
Accompanying drawing explanation
Fig. 1 is the infrared spectrum that the present invention implements products therefrom 6-O-vanilloyl chitosan.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is elaborated.
The preparation of embodiment 1 Rhizoma et radix valerianae acyl chlorides
Prepared carboxylic acid product is placed in 250mL round-bottomed flask, adds 10mL thionyl chloride, instill 3 dimethyl methyls
Amide (DMF), as catalysts and solvents, is heated to reflux 8h, the more rotated thionyl chloride evaporating excess, gained at 40 DEG C
Product is Rhizoma et radix valerianae acyl chlorides.
The preparation of embodiment 2 amido protecting 6-O-vanilloyl chitosan
2g N-phthalyl chitosan is scattered in the DMF of 40mL, is put in magnetic force heating
In agitator, stir 30min at 60 DEG C, after temperature reduces to room temperature, be added dropwise over 37mL Rhizoma et radix valerianae acyl chlorides, react at 35 DEG C
10h, pours in the dehydrated alcohol of 4 times of volumes by reactant liquor, and precipitates overnight at 4 DEG C is centrifuged 3 times with absolute ethanol washing, Gu
Body lyophilization obtains amido protecting 6-O-vanilloyl chitosan.
The preparation of embodiment 3 6-O-vanilloyl chitosan
Being put into by the Rhizoma et radix valerianae acyl chlorides chitosan of 2g amido protecting in the flask of 500mL, add pyridine and hydrazine hydrate, 80 DEG C are returned
Stream 6h, reactant liquor is poured in the dehydrated alcohol of 4 times of volumes, pelleting centrifugation, and solid dehydrated alcohol fully washs, and collects solid,
Last lyophilization obtains 6-O-vanilloyl chitosan.
Embodiment 4 solubility test
Weigh 0.2g sample and put into centrifuge tube, add 25mL distilled water, put in magnetic force heating stirrer, 37 DEG C of reactions
24h, is then centrifuged for, and by solid lyophilization, of poor quality calculates dissolubility according to twice.
Embodiment 5 infrared spectrum structural characterization
Taking the potassium bromide ground and mixed of 1mg chitosan and 100mg, then tabletted on tablet machine, pressure is at 10-
Between 12MPa, stop about 10 seconds, then take out, observe compression molding, the potassium bromide sample strip pressed is put into Fourier
In infrared spectrometer, detection makes collection of illustrative plates.The potassium bromide taking 1mg dried 6-O-vanilloyl chitosan and 100mg the most again grinds
Mill mixing, repeats aforesaid operations and obtains the IR spectrogram (seeing Fig. 1) of sample.6-O-vanilloyl chitosan infrared signature absorbs (cm
-1): 3473 (ν O-H, ν N-H), 1713 and 1776 (ν C=O), 1546 (ν N-H), 1390 (C-O-C), 1119 (ν C3-OH)、1060
(νC6-OH), 900-500 (phenyl ring absorption).
Embodiment 6 Determination of Antibacterial Activity
Weigh chitosan, each 0.1g of 6-O-vanilloyl chitosan, put in 50mL sterilizing small beaker, add 10mL aquesterilisa
It is placed on magnetic force heating stirrer and disperses, then measure the addition of 40ul glacial acetic acid with liquid-transfering gun, continue stirring, then add
10mL aquesterilisa continues to stir obtaining the chitosan acetic acid of 0.1g/mL and 6-O-vanilloyl chitosan-acetic acid solution.Use aquesterilisa again
Above solution is diluted to 5mg/mL, for Determination of Antibacterial Activity.
Superclean bench carries out the switching of strain, measures the acetum of 1mL 5mg/mL with liquid-transfering gun, add PDA
To 10mL, shake up on device shaking up, obtain the antibacterial activity concentration of 0.5mg/mL, pour culture dish into and make flat board, will with card punch
The most cultured confession examination strain breaks into bacterium cake, is inverted in media surface central authorities, and 3 repetitions, 25 DEG C of constant temperature are done in each process
Cultivate, measure the colony diameter of 72h by decussation method, calculate the most as follows for examination growth suppression ratio.
The bacteriostatic activity of table 1 chitosan graft vanilloyl derivant
Note: supplying examination concentration is 0.5mg/mL.
The ultimate principle of the present invention and principal character and advantages of the present invention have more than been shown and described.The technology of the industry
Personnel, it should be appreciated that the present invention is not restricted to the described embodiments, simply illustrating this described in above-described embodiment and description
The principle of invention, without departing from the spirit and scope of the present invention, the present invention also has various changes and modifications, and these become
Change and improvement both falls within scope of the claimed invention.Claimed scope by appending claims and
Equivalent defines.
Claims (10)
1. a chitosan graft vanilloyl derivant, it is characterised in that its structure such as formula I, wherein R is vanilloyl；N is poly-
Right >=2；
。
2. the preparation method of a chitosan graft vanilloyl derivant, it is characterised in that by by vanilloyl and chitosan
Amido protecting thing reaction be prepared.
Method the most according to claim 3, it is characterised in that Rhizoma et radix valerianae acyl chlorides and amido protecting product N-neighbour's benzene of chitosan
Diformyl chitosan reaction generates 2-N-phthalyl-6-O-vanilloyl chitosan, and product is de-in hydrazine hydrate solution
Phthalyl is gone to obtain 6-O-vanilloyl chitosan.
Method the most according to claim 4, it is characterised in that the amido protecting of described chitosan uses and phthalic acid
Anhydride reactant generates N-phthalyl chitosan；Wherein the chitosan molecule degree of polymerization is not less than 2, deacetylation >=80%.
Method the most according to claim 4, it is characterised in that the preparation of described vanilloyl chlorine is to be former with vanillic acid
Material, with dichloromethane as solvent, the thionyl chloride of 3～10 times of equivalents of dropping, in 40 DEG C of back flow reaction, monitored by thin layer chromatography
Reaction process, product decompression distillation, obtain Rhizoma et radix valerianae acyl chlorides.
Method the most according to claim 4, it is characterised in that the amido protecting of chitosan is with chitosan as raw material,
Swelling dispersion in aqueous DMF, adds the phthalic anhydride of about 3 times of equivalents, after 120 DEG C are stirred at reflux 8h
Being cooled to room temperature, product pours in frozen water, filtration under diminished pressure with distilled water wash, is scattered in ethanol by product and fills after filtration
Point washing, centrifugal, lyophilization obtain N-phthalyl chitosan.
Method the most according to claim 4, it is characterised in that N-phthalyl chitosan is scattered in N, N-diformazan
In base Methanamide, at 60 DEG C, stir swelling 30min, after temperature is down to room temperature, is added dropwise over the excess N containing vanilloyl chlorine,
Dinethylformamide solution, reacts 10h at 35 DEG C.Reactant liquor is poured in 4 times amount dehydrated alcohol, at 4 DEG C, precipitates 1h,
Being centrifuged 3 times with absolute ethanol washing, lyophilization obtains light brown product, is acylate 2-N-phthalyl-6-O-
Vanilloyl chitosan.
Method the most according to claim 4, it is characterised in that take described 2-N-phthalyl-6-O-vanilloyl shell
Polysaccharide, adds in pyridine and the hydrazine hydrate of equal-volume mixing, and 80 DEG C of backflow 6h, it is heavy that reactant liquor is poured in 4 times of volume dehydrated alcohol
Forming sediment, centrifugal, solid ethanol fully washs, and low temperature is frozen into solid, last lyophilization, obtains khaki powdered product, i.e. 6-
O-vanilloyl chitosan.
9. chitosan graft vanilloyl derivant application in preparing water base antibacterial.
10. chitosan graft vanilloyl derivant is in preparation suppression botrytis cinerea, fusarium graminearum, Phytophthora capsici disease
Application in bacterium or rhizoctonia cerealis medicine.
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Cited By (3)
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| CN107619446A (en) * | 2017-09-26 | 2018-01-23 | 西南石油大学 | A kind of preparation method of maleylation phthalyl chitosan |
| CN108559009A (en) * | 2017-09-26 | 2018-09-21 | 西南石油大学 | A kind of preparation method of phthaloyl chitosan |
| CN113429493A (en) * | 2021-06-29 | 2021-09-24 | 吉祥三宝高科纺织有限公司 | Preparation method of non-release type high-molecular antibacterial anti-mite agent |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107619446A (en) * | 2017-09-26 | 2018-01-23 | 西南石油大学 | A kind of preparation method of maleylation phthalyl chitosan |
| CN108559009A (en) * | 2017-09-26 | 2018-09-21 | 西南石油大学 | A kind of preparation method of phthaloyl chitosan |
| CN113429493A (en) * | 2021-06-29 | 2021-09-24 | 吉祥三宝高科纺织有限公司 | Preparation method of non-release type high-molecular antibacterial anti-mite agent |
| CN113429493B (en) * | 2021-06-29 | 2022-06-17 | 吉祥三宝高科纺织有限公司 | Preparation method of non-release type high-molecular antibacterial anti-mite agent |
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| CN106117392B (en) | 2021-02-09 |
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