CN109369828A - A kind of synthetic method of anti-lung cancer activity bagasse xylan caffeic acid ester-g-AM - Google Patents
A kind of synthetic method of anti-lung cancer activity bagasse xylan caffeic acid ester-g-AM Download PDFInfo
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- CN109369828A CN109369828A CN201811225985.2A CN201811225985A CN109369828A CN 109369828 A CN109369828 A CN 109369828A CN 201811225985 A CN201811225985 A CN 201811225985A CN 109369828 A CN109369828 A CN 109369828A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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Abstract
The invention discloses the synthetic methods of bagasse xylan caffeic acid ester-g-AM a kind of.Using natural macromolecule biological activity bagasse xylan as primary raw material, using ammonium persulfate and sodium hydrogensulfite as initiation system, N, N '-methylene-bisacrylamide for crosslinking agent, synthesizes bagasse xylan-g-AM first in aqueous phase solution；Again using bagasse xylan-g-AM as raw material, caffeic acid is esterifying agent, and cerous sulfate and ammonium persulfate are composite catalyst, and bagasse xylan caffeic acid ester-g-AM is synthesized in dichloromethane solvent.Product prepared by the present invention is that esterification is carried out on the basis of grafting, and the bagasse xylan caffeic acid ester-g-AM of synthesis improves the water solubility of bagasse xylan, expands its application field.Meanwhile introducing acrylamide (AM) and caffeinic active group further improve the bioactivity of bagasse xylan.
Description
Technical field
The present invention relates to polymeric material field, especially a kind of anti-lung cancer activity bagasse xylan caffeic acid ester-g-AM
Synthetic method.
Background technique
Xylan in bagasse can be converted into value product by physics and chemical modification.In recent years, both at home and abroad
Scholar increases the active group of xylan by a series of chemical modifications such as etherificate, oxidation, amination, esterification, graft copolymerizations,
It is set to obtain higher bioactivity.But research at present is mostly the simple or step modification of xylan, to composite modified xylan
Research just start to walk.
Xylan is by being that grafted monomers progress graft copolymerization product can not only improve it with acrylamide (AM)
Bioactivity, moreover it is possible to improve other performances of graft polymers.Polymer containing coffee acid groups have anti-oxidant, anticancer,
The pharmacological actions such as immunological regulation, antiviral.If coffee acid groups can be introduced on the pendant hydroxyl group of xylan, in conjunction with the two
The antitumaous effect of xylan derivative can be improved in performance characteristics.Thus the present invention is on the basis of designing bagasse xylan-g-AM
The bioactivity of bagasse xylan is further increased by introducing coffee acid groups.
The present invention is using natural macromolecule biological activity bagasse xylan as primary raw material, with ammonium persulfate and bisulfite
Sodium is initiation system, and N, N '-methylene-bisacrylamide are crosslinking agent, synthesizes bagasse xylan-g- first in aqueous phase solution
AM；Again using bagasse xylan-g-AM as raw material, caffeic acid is esterifying agent, and cerous sulfate and ammonium persulfate are composite catalyst, two
Bagasse xylan caffeic acid ester-g-AM is synthesized in chloromethane alkane solvents.
Summary of the invention
The purpose of the invention is to enhance the bioactivity of bagasse xylan, it is poly- to provide a kind of anti-lung cancer activity bagasse wood
The preparation method of sugared caffeic acid ester-g-AM.
Specific steps of the invention are as follows:
(1) 5~10g bagasse xylan is obtained into butt sugarcane to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Slag xylan.
(2) butt bagasse xylan obtained by 3~5g step (1) is weighed to be added in 250mL four-hole boiling flask, add 15~
20mL deionized water stirs 20~25 minutes at 40~50 DEG C.
(3) 0.5~0.8g ammonium persulfate and 0.02~0.05g sodium hydrogensulfite are successively weighed in 100mL beaker, then
10~20mL deionized water is added and is made into initiator solution, it is spare.
(4) 2~5gAM is weighed in 100mL beaker, and 20~30mL deionized water, stirring and dissolving are then added into beaker
It is uniform to obtain monomer solution, it pours into 100mL constant pressure funnel, it is spare.
(5) monomer solution is added dropwise into the reaction system of step (2), control temperature was added dropwise in 40~50 DEG C, 5~6 hours
It finishes；When adding to the 1/2 of monomer solution volume, 0.1~0.2g N, N '-methylene-bisacrylamide is added.Meanwhile in batches
Initiator solution obtained by step (3) is added, every 10~15 minutes 0.3~0.6mL of additions, is added dropwise afterwards that the reaction was continued 2~4
Hour.To which after reaction, system is cooled to room temperature.
(6) 20~30mL is added into step (5) resulting material to analyze pure acetone precipitating 20~30 minutes, filters and with 10
The washing of~20mL dehydrated alcohol filters 2~3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24
Hour is to constant weight to get bagasse xylan-g-AM.
(7) intermediate product bagasse xylan-g-AM obtained by 1~2g step (6) is weighed to be added in 250mL four-hole boiling flask,
Then 0.5~2g caffeic acid is sequentially added, 1~2g N, N- dicyclohexylcarbodiimide, 0.05~0.15g cerous sulfate, 0.05~
0.12g ammonium persulfate and 15~20mL analyze absolute dichloromethane, control reaction temperature at 70~80 DEG C, it is small to be stirred to react 7~9
When, system is cooled to room temperature.
(8) step (7) gained reactant material is successively washed with 20~25mL dehydrated alcohol, 20~25mL analysis pure acetone
It washs, filter 2~3 times, filter cake is put into surface plate, is placed in 50 DEG C of thermostatic drying chambers dry 24 hours to constant weight to get final
Target product bagasse xylan caffeic acid ester-g-AM.
(9) measurement of esterification degree of substitution is carried out to bagasse xylan caffeic acid ester obtained by step (8) using acid-base titration,
Specific method and steps are as follows: accurate weighing 0.5g sample is placed in 50mL slot conical flask, and 10mL deionized water is added, shakes
It is even, add the phenolphthalein indicator of 3 drops.Concentration is used to titrate above-mentioned solution to light red for the NaOH standard solution of 0.1mol/L
(color is not taken off in 30 seconds).The NaOH standard solution that 2.5mL concentration is 0.5mol/L is added, shakes up, seals, is placed in electronic vibration
Swing concussion saponification 4 hours in device；The HCl standard solution for being finally 0.5mol/L with concentration is titrated to colourless, as titration end-point.
The calculating formula for being esterified degree of substitution (DS) is as follows:
In formula:
Wc--- the mass fraction of coffee acyl, % in target product；
V0--- titration bagasse xylan uses the amount of HCI standard solution, Unit/mL；
V1--- the standard solution amount of hydrochloric acid used in titration final product, Unit/mL；
CHCl--- the concentration of hydrochloric acid standard solution, unit mol/L；
M --- the quality of target product sample, unit g；
The relative molecular mass of M --- coffee acyl；
132 --- the relative molecular mass of bagasse xylan dewatering unit；
DS --- the degree of substitution of bagasse xylan caffeic acid ester.
(10) monomer grafting rate and grafting efficiency in determination step (8) products therefrom, specific method and steps are as follows: will be thick
After graft copolymer acetone precipitation, pure dehydrated alcohol is analyzed with 10~20mL respectively and is washed 2~3 times, is dried in vacuo at 55 DEG C
It dries in case to constant weight, obtains graft copolymerization crude product.Then, use analysis pure acetone will be thick as solvent in Soxhlet extractor
Product extracts 24 hours, and the taking-up of sample after extracting is put into 60 DEG C of vacuum ovens dry 24 hours and obtains pure grafting to constant weight
Copolymer.The calculation method of grafting rate and grafting efficiency is as follows:
In formula:
Wg--- the quality of graft esterification copolymer, g；
W0--- the quality of former bagasse xylan, g；
W1--- the quality of grafted branches, g；
W2--- the quality of monomer, g；
G --- grafting rate, %；
GE --- grafting efficiency, %.
The water solubility of bagasse xylan is not only improved using the target product that this technique synthesizes, introduces AM and caffeinic
Active group further improves the anticancer bioactive of bagasse xylan.
Detailed description of the invention
Fig. 1 is the SEM photograph of bagasse xylan.
Fig. 2 is the SEM photograph of bagasse xylan caffeic acid ester-g-AM.
Fig. 3 is original bagasse xylan IR figure.
The IR that Fig. 4 is bagasse xylan caffeic acid ester-g-AM schemes.
Fig. 5 is the XRD diagram of former bagasse xylan.
Fig. 6 is the XRD diagram of bagasse xylan caffeic acid ester-g-AM.
Fig. 7 is TG the and DTG curve of former bagasse xylan.
Fig. 8 is TG the and DTG curve of bagasse xylan caffeic acid ester-g-AM.
Specific embodiment
Embodiment:
(1) 6g bagasse xylan is obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Glycan.
(2) it weighs butt bagasse xylan obtained by 4g step (1) to be added in 250mL four-hole boiling flask, adds 15mL and go
Ionized water stirs 20 minutes at 45 DEG C.
(3) 0.6g ammonium persulfate and 0.03g sodium hydrogensulfite are successively weighed in 100mL beaker, 15mL is then added and goes
Ionized water is made into initiator solution, spare.
(4) 3gAM is weighed in 100mL beaker, the deionized water of 20mL is then added into beaker, stirring and dissolving is uniform
Monomer solution is obtained, is poured into 100mL constant pressure funnel, it is spare.
(5) monomer solution is added dropwise into the reaction system of step (2), controls temperature at 45 DEG C, is added dropwise within 5 hours；When
When adding to the 1/2 of monomer solution volume, 0.15g N, N '-methylene-bisacrylamide is added.Meanwhile step (3) are added portionwise
Gained initiator solution, every 10 minutes addition 0.5mL, the reaction was continued 3 hours after being added dropwise.To after reaction, cool down
To room temperature.
(6) 30mL is added into step (5) resulting material to analyze pure acetone precipitating 25 minutes, filters and with the anhydrous second of 20mL
Alcohol washing filters 3 times, and filter cake is put into surface plate, be placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get
Bagasse xylan-g-AM.
(7) it weighs intermediate product bagasse xylan-g-AM obtained by 1g step (6) to be added in 250mL four-hole boiling flask, then
Sequentially add 1.5g caffeic acid, 1g N, N- dicyclohexylcarbodiimide, 0.1g cerous sulfate, 0.08g ammonium persulfate and 15mL analysis
Absolute dichloromethane controls reaction temperature at 70 DEG C, is stirred to react 7 hours, system is cooled to room temperature.
(8) step (7) gained reactant material successively washed with 25mL dehydrated alcohol, 25mL analysis pure acetone, filter 3
Secondary, filter cake is put into surface plate, is placed in 50 DEG C of thermostatic drying chambers dry 24 hours to constant weight to get final goal product bagasse
Xylan caffeic acid ester-g-AM.
(9) caffeic acid esterification degree of substitution measurement is carried out to step (10) products therefrom using acid-base titration, obtains DS=
0.089。
(10) monomer grafting rate is 76.3% in determination step (9) products therefrom, grafting efficiency 80.4%.
Product bagasse xylan caffeic acid ester-g-AM is analyzed through IR, and the modified product of graft esterification is in 1706.77cm-1
There is the carbonyl eigen vibration absorption peak of AM and ester bond, 1665.52cm-1Place is amide stretching vibration absworption peak, 1504.20cm-1
Place is phenyl ring skeleton stretching vibration absworption peak.Through XRD analysis it is found that product after esterification modification powder angle be 17.33 °,
Peak crystallization increases at 20.09 °, 21.46 °, 24.92 °, 26.69 °, and peak type is stronger, illustrates that crystalline content is more, crystal region is complete.
Sem analysis show by reaction after, surface is uneven, have sheet packed structures, have obviously gap and
Damaged rill, it was demonstrated that sent out change by modified body structure surface.TG the and DTG curve for analyzing graft esterification product, at 200 DEG C
To 250 DEG C of stages, mass loss has reached 23%, mainly caused by the decomposition of bagasse xylan caffeic acid ester-g-AM itself,
Product thermal stability compared with former bagasse xylan at 800 DEG C significantly improves.
Claims (1)
1. a kind of synthetic method of anti-lung cancer bagasse xylan caffeic acid ester-g-AM, it is characterised in that specific steps are as follows:
(1) 5 ~ 10g bagasse xylan it is poly- to be obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Sugar；
(2) it weighs butt bagasse xylan obtained by 3 ~ 5g step (1) to be added in 250mL four-hole boiling flask, adds 15 ~ 20mL and go
Ionized water stirs 20 ~ 25 minutes at 40 ~ 50 DEG C；
(3) 0.5 ~ 0.8g ammonium persulfate and 0.02 ~ 0.05g sodium hydrogensulfite are successively weighed in 100mL beaker, is then added 10
~ 20mL deionized water is made into initiator solution, spare；
(4) 2 ~ 5gAM is weighed in 100mL beaker, 20 ~ 30mL deionized water is then added into beaker, and stirring and dissolving is uniform to be obtained
Monomer solution pours into 100mL constant pressure funnel, spare；
(5) monomer solution is added dropwise into the reaction system of step (2), controls temperature at 40 ~ 50 DEG C, is added dropwise within 5 ~ 6 hours；When
When adding to the 1/2 of monomer solution volume, 0.1 ~ 0.2g N, N '-methylene-bisacrylamide is added；Meanwhile step is added portionwise
(3) gained initiator solution, every 10 ~ 15 minutes 0.3 ~ 0.6mL of addition, the reaction was continued 2 ~ 4 hours after being added dropwise；Wait react
After, system is cooled to room temperature；
(6) 20 ~ 30mL is added into step (5) resulting material to analyze pure acetone precipitating 20 ~ 30 minutes, filters and with 10 ~ 20mL
Dehydrated alcohol washing filters 2 ~ 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours extremely
Constant weight is to get bagasse xylan-g-AM；
(7) intermediate product bagasse xylan-g-AM obtained by 1 ~ 2g step (6) is weighed to be added in 250mL four-hole boiling flask, then according to
0.5 ~ 2g of secondary addition caffeic acid, 1 ~ 2g N, N- dicyclohexylcarbodiimide, 0.05 ~ 0.15g cerous sulfate, 0.05 ~ 0.12g over cure
Sour ammonium and 15 ~ 20mL analyze absolute dichloromethane, control reaction temperature at 70 ~ 80 DEG C, are stirred to react 7 ~ 9 hours, system is cooled to
Room temperature；
(8) step (7) gained reactant material successively washed with 20 ~ 25 mL dehydrated alcohols, 20 ~ 25 mL analysis pure acetone, taken out
Filter 2 ~ 3 times, filter cake is put into surface plate, is placed in 50 DEG C of thermostatic drying chambers dry 24 hours to constant weight to get bagasse xylan
Caffeic acid ester-g-AM.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175140A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active BX/SGPS quaternary graft copolymerization derivative |
| CN112175142A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of bagasse xylan bromopyruvate-g-AM/MA |
| CN112175141A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM |
| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
| CN112250797A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Synthesis method of active bagasse xylan bromopyruvate-g-AM/MA/BzA |
| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN112175141A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM |
| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
| CN112250797A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Synthesis method of active bagasse xylan bromopyruvate-g-AM/MA/BzA |
| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
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Application publication date: 20190222 |