CN115463622A - Gel based on oxidized pectin and preparation method thereof - Google Patents
Gel based on oxidized pectin and preparation method thereof Download PDFInfo
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0052—Preparation of gels
- B01J13/0065—Preparation of gels containing an organic phase
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- 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
- C08B37/0045—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Galacturonans, e.g. methyl ester of (alpha-1,4)-linked D-galacturonic acid units, i.e. pectin, or hydrolysis product of methyl ester of alpha-1,4-linked D-galacturonic acid units, i.e. pectinic acid; Derivatives thereof
Abstract
The invention belongs to the technical field of biochemistry, and particularly relates to gel based on oxidized pectin and a preparation method thereof. The preparation method comprises the steps of adjusting the pH value of a pectin solution to be below 5.0, then adding an oxidizing agent for oxidation modification, adding a terminator for termination reaction, adjusting the pH value to be below 5.0 after redissolving the oxidized pectin, then adding a chemical cross-linking agent and a physical cross-linking agent, fully mixing, standing and gelling. According to the invention, a dialdehyde structure with higher activity is introduced into pectin molecules through oxidation modification, so that the oxidized pectin has the capability of covalent crosslinking with amino compounds, a double-gel network jointly stabilized by covalent bonds and ionic bonds is constructed by crosslinking the oxidized pectin molecules with multi-amino compounds and multivalent cations, and the prepared pectin gel has the characteristics of simple gel conditions and stronger gel elasticity, and has an application prospect in the field of biomedicine.
Description
Technical Field
The invention belongs to the technical field of biochemistry, and particularly relates to gel based on oxidized pectin and a preparation method thereof.
Background
Pectin molecules are anionic heteropolysaccharides that are commonly distributed in the cell walls of higher plants and are widely used in the food industry as gelling agents, and the main gelling mechanisms thereof can be classified into ionic gelling mechanisms (low ester pectins) and acid + sugar gelling mechanisms (high ester pectins) according to the degree of methyl esterification. The two gel systems are based on ionic bonds between carboxyl and cations and hydrogen bonds between hydroxyl respectively, belong to weak interaction, and limit the gel strength and application range of pectin.
CN109046190A discloses a pectin composite silicon dioxide aerogel and a preparation method and application thereof, and particularly discloses a pectin composite silicon dioxide aerogel comprising the following steps: step 1: adjusting pH of sodium silicate solution to 3-4, adding pectin and silicon dioxide, and mixing to obtain a mixture; step 2: mixing the mixture with calcium ion-containing compound, and adjusting pH to 5-6 to obtain gel; and 3, step 3: and (3) sequentially carrying out aging, solvent replacement and freeze drying on the gel to obtain the pectin composite silicon dioxide aerogel. The calcium ions are used in the technical scheme, the pectin in the aerogel can be well stabilized, the aerogel keeps a mesoporous structure, the network framework of the aerogel can not be damaged by overlarge surface tension in the drying process, excessive toxic and harmful inorganic matters are used, and an improvement space is reserved.
CN 113731307B discloses an ammonium sulfate-containing high-ester pectin gel and a preparation method and application thereof, specifically discloses 1) dissolving high-ester pectin in water, adjusting pH to 4-7, and obtaining a high-ester pectin solution; mixing ammonium sulfate or an ammonium sulfate aqueous solution with a high-ester pectin solution to obtain a mixed solution containing ammonium sulfate; 2) Adjusting the pH of the mixed solution containing ammonium sulfate to be less than or equal to 3.5, homogenizing, and standing to obtain high-ester pectin gel; in the step 1), the mass concentration of ammonium sulfate in the mixed solution containing ammonium sulfate is 25-30%, and the mass concentration of high ester pectin is 0.2-1.5%. The technical scheme successfully realizes the gelation of the high ester pectin under an ammonium sulfate + acid system, but the technical scheme is pure physical crosslinking and has no chemical modification,
in review, the prior art is still lacking a method of increasing the gel strength of pectin.
Disclosure of Invention
Aiming at the defects or improvement requirements of the prior art, the invention provides gel based on oxidized pectin and a preparation method thereof, aiming at introducing a higher-activity dialdehyde structure into pectin molecules for oxidative modification, so that the oxidized pectin has the capability of covalent crosslinking with amino compounds, thereby solving the technical problem of insufficient gel strength of the existing pectin.
The periodate oxidation can oxidize adjacent hydroxyl groups into a dialdehyde structure, and the introduction of active aldehyde groups into pectin molecules can further enrich the gel mechanism. The Schiff base reaction is a chemical process that amino and aldehyde groups are crosslinked to form dynamic covalent imine bonds, different types of Schiff base gels are prepared by taking polysaccharide as a raw material, adjustable mechanical properties and chemical stability can be obtained, and the Schiff base gel has wide application prospects in medical fields of biological materials, tissue repair, drug sustained release and the like.
To achieve the above objects, according to one aspect of the present invention, there is provided a method for preparing an oxidized pectin-based gel, comprising the steps of:
(1) Preparing oxidized pectin: adjusting the pH value of the pectin solution to be below 5.0, adding an oxidizing agent for oxidation modification, adding a terminator for terminating the reaction, then carrying out alcohol precipitation on the reaction solution to obtain a precipitate, and separating an alcohol solvent in the precipitate to obtain oxidized pectin;
(2) Re-dissolving the oxidized pectin, adjusting the pH value to be below 5.0, adding a chemical cross-linking agent and a physical cross-linking agent, fully mixing, standing for gelation, wherein the chemical cross-linking agent is used for performing Schiff base reaction with the oxidized pectin to form co-bond cross-linking, and the physical cross-linking agent is used for forming ionic cross-linking with the oxidized pectin.
Preferably, the aldehyde group content of the pectin oxide is more than 0.75mmol/g.
Preferably, the oxidizing agent is at least one of sodium periodate, hydrogen peroxide and sodium hypochlorite, preferably sodium periodate.
Preferably, the terminating agent includes at least one of polyethylene glycol, ascorbic acid, and sodium thiosulfate.
Preferably, the chemical crosslinking agent is at least one of adipic Acid Dihydrazide (ADH),. And. Includes polyamino compounds, and preferably adipic acid dihydrazide.
Preferably, the physical crosslinking agent is at least one of calcium chloride, zinc chloride, ferric chloride, magnesium sulfate and magnesium chloride.
Preferably, the pectin raw material in the step (1) is at least one of lemon peel pectin, orange peel pectin and apple peel pectin.
Preferably, alkali is added in the step (1) and the step (2) to adjust the pH value to be 4.0-5.0.
Preferably, the reaction temperature in the step (1) and the step (2) is 20 ℃ to 30 ℃.
According to another aspect of the present invention, there is provided a gel of oxidized pectin prepared by the method for preparing a gel based on oxidized pectin.
The pectin polysaccharide contains a large amount of hydroxyl and carboxyl, the gel is mainly stabilized by ionic bonds and hydrogen bonds, the defect of weak gel strength is caused, and the gel condition needs extra high-temperature boiling and a large amount of co-solute. This not only complicates the gel preparation process and increases energy consumption, but also limits the application of pectin gels.
According to the invention, a dialdehyde structure with higher activity is introduced into pectin molecules through oxidation modification, so that the oxidized pectin has the capability of covalent crosslinking with amino compounds. By controlling the dosage of the oxidant, the proportion of the oxidant to the pectin and the oxidation time, the pectin with different oxidation degrees can be prepared; subsequently, the oxidized pectin molecules are crosslinked by polyamino compounds and multivalent cations, and a double gel network stabilized by covalent bonds and ionic bonds is constructed. The pectin gel prepared by the method has the characteristics of simple gel condition and stronger gel elasticity, and has application prospects in the field of biomedicine. The preparation method of the pectin gel provided by the invention is simple to operate, the gel strength and elasticity are far higher than those of the traditional pectin gel based on physical interaction, and the gel strategy and application scene of pectin are enriched.
In general, compared with the prior art, the above technical solution conceived by the present invention can achieve the following beneficial effects:
(1) The invention prepares the pectin oxide containing dialdehyde structure in ADH and Ca 2+ Gelation is easily achieved under double crosslinking.
(2) The invention can control the pectin oxidation degree according to the oxidant dosage, proportion and oxidation time, further control the mechanical performance of the pectin gel according to the oxidation degree and content of the oxidized pectin and the dosage of the cross-linking agent, and broaden the application range of the pectin gel.
(3) The pectin gel prepared by the invention is jointly stabilized by ionic bonds and covalent bonds, and the gel strength and elasticity are obviously superior to those of the traditional physically crosslinked pectin gel.
(4) The imine bond formed in the gel of the pectin oxide prepared in the invention has reversibility.
Drawings
FIG. 1 is a graph showing the gel morphology and rheological property tests of example 1 and comparative examples 1 to 2.
FIG. 2 is the gel rheology strength of comparative example 3 and examples 1-3.
FIG. 3 is a gel morphology chart of comparative examples 1 to 3 and examples 1 to 3.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. In addition, the technical features involved in the embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
Examples
Comparative example 1
(1) Adding 2.5g of pectin into 100mL of distilled water, stirring in a magnetic stirrer at 30 ℃ until the pectin is fully dissolved to obtain a pectin solution, and adjusting the pH value to 5.0; adding no sodium periodate, stirring for 12 hr, adding 10mL ethylene glycol, adding the pectin solution into 3 times volume of anhydrous ethanol for precipitation, repeating the steps for 3 times, and finally freeze-drying to remove ethanol to obtain pectin.
(2) Weighing 1g of the pectin, dissolving in 20mL of distilled water, adjusting the pH of the pectin solution to 5.0, and adding 2mL of CaCl to the pectin solution 2 (0.1M), mixed well and left to stand for gelation.
Comparative example 2
This example differs from example 1 in that pectin is oxidatively modified in step (1), as described below.
(1) Adding 2.5g of pectin into 100mL of distilled water, stirring in a magnetic stirrer at 30 ℃ until the pectin is fully dissolved to obtain a pectin solution, and adjusting the pH value to 5.0; adding solid sodium periodate into a pectin solution, wherein the mass ratio of pectin to periodic acid in the solution is 10:1, adding periodic acid while continuously stirring the pectin solution, reacting for 12 hours, adding 10mL of ethylene glycol to stop the oxidation reaction, pouring the pectin solution into 3 times of volume of absolute ethyl alcohol for precipitation, repeating the steps for 3 times, and finally freeze-drying to remove the ethyl alcohol to obtain the oxidized pectin. The aldehyde group content of the pectin oxide is 0.75mmol/g through testing.
(2) Weighing 1g of pectin oxide, dissolving in 20mL of distilled water, adjusting pH of the pectin solution to 5.0, adding 2mL of CaCl into the pectin solution 2 (0.1M), mixed well and left to gel.
Comparative example 3
This example differs from comparative example 2 in that no oxidative modification of the pectin was carried out in step (1) and in step (2) a chemical cross-linking agent, adipic Dihydrazide (ADH), was added as follows.
(1) Adding 2.5g of pectin into 100mL of distilled water, stirring in a magnetic stirrer at 30 ℃ until the pectin is fully dissolved to obtain a pectin solution, and adjusting the pH value to 5.0; stirring for 12 hr, adding 10mL ethylene glycol, precipitating the pectin solution with 3 times volume of anhydrous ethanol, repeating the above steps for 3 times, and lyophilizing to remove ethanol to obtain pectin.
(2) 1g of pectin was weighed and dissolved in 20mL of distilled water, the pH of the pectin solution was adjusted to 5.0, and 0.8mL of adipic Acid Dihydrazide (ADH) solution (0.5M) and 2mL of CaCl2 (0.1M) were added to the pectin solution, followed by thorough mixing and gelation by standing.
Example 1
This example differs from comparative example 3 in that pectin is oxidatively modified in step (1), as described below.
(1) Adding 2.5g of pectin into 100mL of distilled water, stirring in a magnetic stirrer at 30 ℃ until the pectin is fully dissolved to obtain a pectin solution, and adjusting the pH value to 5.0; adding solid sodium periodate into a pectin solution, wherein the mass ratio of pectin to periodic acid in the solution is 50:1, adding periodic acid while continuously stirring the pectin solution, reacting for 12 hours, adding 10mL of ethylene glycol, pouring the pectin solution into 3 times of volume of absolute ethyl alcohol for precipitation, repeating the operation for 3 times, and finally freeze-drying to remove the ethanol to obtain the oxidized pectin. Through testing, the aldehyde group content of the pectin oxide is 0.35mmol/g.
(2) 1g of oxidized pectin was weighed out and dissolved in 20mL of distilled water, the pH of the pectin solution was adjusted to 5.0, and then 0.8mL of adipic Acid Dihydrazide (ADH) solution (0.5M) and 2mL of CaCl2 (0.1M) were added to the pectin solution, followed by thorough mixing and gelation by standing.
Example 2
This example is different from example 1 in the amount of the oxidizing agent used in step (1), and is specifically described below.
(1) Adding 2.5g of pectin into 100mL of distilled water, stirring in a magnetic stirrer at 30 ℃ until the pectin is fully dissolved to obtain a pectin solution, and adjusting the pH value to 5.0; adding solid sodium periodate into a pectin solution, wherein the mass ratio of pectin to periodic acid in the solution is 10:1, adding periodic acid while continuously stirring the pectin solution, reacting for 12 hours, adding 10mL of ethylene glycol, pouring the pectin solution into 3 times of volume of absolute ethyl alcohol for precipitation, repeating the operation for 3 times, and finally freeze-drying to remove the ethanol to obtain the oxidized pectin. The aldehyde group content of the pectin oxide is 0.75mmol/g through testing.
(2) 1g of oxidized pectin was weighed out and dissolved in 20mL of distilled water, the pH of the pectin solution was adjusted to 5.0, and then 0.8mL of adipic Acid Dihydrazide (ADH) solution (0.5M) and 2mL of CaCl2 (0.1M) were added to the pectin solution, followed by thorough mixing and gelation by standing.
Example 3
This example is different from example 1 in the amount of the oxidizing agent used in step (1), and is specifically described below.
(1) Adding 2.5g of pectin into 100mL of distilled water, stirring in a magnetic stirrer at 30 ℃ until the pectin is fully dissolved to obtain a pectin solution, and adjusting the pH value to 5.0; adding solid sodium periodate into a pectin solution, wherein the mass ratio of pectin to periodic acid in the solution is 8:1, adding periodic acid while continuously stirring the pectin solution, reacting for 12 hours, adding 10mL of ethylene glycol, pouring the pectin solution into 3 times of volume of absolute ethyl alcohol for precipitation, repeating the operation for 3 times, and finally freeze-drying to remove the ethanol to obtain the oxidized pectin. The aldehyde group content of the pectin oxide is 1mmol/g through testing.
(2) 1g of oxidized pectin was weighed out and dissolved in 20mL of distilled water, the pH of the pectin solution was adjusted to 5.0, and then 0.8mL of adipic Acid Dihydrazide (ADH) solution (0.5M) and 2mL of CaCl2 (0.1M) were added to the pectin solution, followed by thorough mixing and gelation by standing.
Test examples
The high esterified orange peel pectin used in the following manufacturing examples was purchased from lime biotech limited, guangzhou.
The apparatus used in the examples: the homogenizer model was T10 homogenizer (IkA).
And (3) determining the aldehyde group content of pectin:
referring to the literature "Liuwenying, preparation of the oxidized cellulose/chitosan composite hemostatic material and performance research [ D ]", weighing a certain amount of oxidized pectin, adding a certain volume of 0.25M hydroxylamine hydrochloride-methyl orange solution, and fully stirring for 4 hours. Finally, titration with 0.1M standard NaOH solution until the solution changes color from pink to yellow, which titrates the head office to solution pH =5.0. The calculation formula of the aldehyde group content [ CHO ] is as follows:
[CHO]＝(V 2 -V 1 )×c/m
wherein the aldehyde group content [ CHO]The unit is mmol/g; c: naOH solubility, mol/L; v 2 : the titration end point needs NaOH volume, mL; v 1 : blank titration of the consumed NaOH volume, mL; m: oxidized pectin mass, g.
1. Rheological testing of pectin gels:
the pectin gel is tested on a rheometer by adopting parallel plates with the diameter of 35mm according to the research on the influence of environmental conditions and glycosylation on the oil-water interface property of soybean 7S protein and an emulsification mechanism [ D ]. The set spacing was 1mm and the test temperature was 25 ℃. The fixed shear frequency is 5rad/s and strain sweep is performed (0.1% to 1000%).
Fig. 1 is the gel rheology strength of comparative example 1 and comparative example 2.
FIG. 2 is the gel rheology strength of comparative example 3 and examples 1-3.
FIG. 3 is a gel morphology chart of comparative examples 1 to 3 and examples 1 to 3
As can be seen from FIG. 1, the method of the present invention employs ADH + Ca 2+ The cross-linked pectin oxide can form a stable gel structure. From comparative examples 1 and 2 (fig. 1), it is known that oxidation results in the cleavage of pectin molecular chains and is not suitable for physical crosslinking mode based on ionic bonds. From comparative example 3 and examples 1 to 3 (FIG. 2), ADH + Ca is known 2+ In the crosslinking mode, pectin with lower oxidation degree (aldehyde group content less than 0.75 mmol/g) has reduced molecular weight and insufficient aldehyde group content, and the gel strength of the formed pectin is not as strong as Ca 2+ Cross-linked is pectin oxide; and with oxidationIncrease in degree based on ADH + Ca 2+ The strength of the cross-linked pectin gel is gradually increased and is increased by ADH + Ca 2+ The cross-linked pectin oxide gel can resist stronger denaturation and keep the gel structure stable, which shows that the pectin oxide gel prepared by the invention has unique gel property.
It will be understood by those skilled in the art that the foregoing is only an exemplary embodiment of the present invention, and is not intended to limit the invention to the particular forms disclosed, and all changes, equivalents and modifications that fall within the spirit and scope of the invention are therefore intended to be embraced therein.
Claims (10)
1. A method for preparing a gel based on oxidized pectin, comprising the steps of:
(1) Preparing oxidized pectin: adjusting the pH value of the pectin solution to be below 5.0, adding an oxidant for oxidation modification, adding a terminator for terminating the reaction, then carrying out alcohol precipitation on the reaction solution to obtain a precipitate, and separating an alcohol solvent in the precipitate to obtain oxidized pectin;
(2) Re-dissolving the oxidized pectin, adjusting the pH value to be below 5.0, adding a chemical cross-linking agent and a physical cross-linking agent, fully mixing, standing for gelation, wherein the chemical cross-linking agent is used for performing Schiff base reaction with the oxidized pectin to form co-bond cross-linking, and the physical cross-linking agent is used for forming ionic cross-linking with the oxidized pectin.
2. The method according to claim 1, wherein the aldehyde group content of the pectin oxide is 0.75mmol/g or more.
3. The method according to claim 1 or 2, wherein the oxidizing agent is at least one of sodium periodate, hydrogen peroxide and sodium hypochlorite, preferably sodium periodate.
4. The method according to claim 3, wherein the terminating agent includes at least one of polyethylene glycol, ascorbic acid, and sodium thiosulfate.
5. The method according to claim 1, wherein the chemical crosslinking agent is at least one of adipic acid dihydrazide, chitosan, and ethylenediamine, preferably adipic acid dihydrazide.
6. The method according to claim 5, wherein the physical crosslinking agent is at least one of calcium chloride, zinc chloride, ferric chloride, magnesium sulfate, and magnesium chloride.
7. The preparation method according to claim 2, wherein the pectin material in step (1) is at least one of lemon peel pectin, orange peel pectin, and apple peel pectin.
8. The method according to claim 1, wherein a base is added in the steps (1) and (2) to adjust the pH to 4.0 to 5.0.
9. The method according to claim 1, wherein the reaction temperature in the step (1) and the step (2) is 20 ℃ to 30 ℃.
10. A gel of oxidized pectin prepared according to the method of preparing a gel based on oxidized pectin of any of claims 1-9.
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