CN115160452A - High-ester pectin containing active aldehyde group structure and preparation method thereof - Google Patents
High-ester pectin containing active aldehyde group structure and preparation method thereof Download PDFInfo
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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 biological pharmacy, and particularly relates to high-ester pectin containing an active aldehyde group structure and a preparation method thereof. The method comprises the following steps: (1) Fully dissolving pectin to obtain pectin solution, and adding alkali to adjust pH to below 5.0; (2) Adding a specific oxidant for light-shielding reaction, wherein the specific oxidant can selectively oxidize the o-dihydroxy of the non-esterified galacturonic acid, promote the degradation of the non-esterified galacturonic acid and break the molecular chain skeleton of the pectin to obtain the high-ester pectin containing an active aldehyde group structure; (3) Adding a terminator to terminate the reaction, then carrying out alcohol precipitation on the reaction solution through ethanol, separating an alcohol precipitation product, and freeze-drying to obtain the pectin oxide. According to the invention, the o-dihydroxy of the non-esterified galacturonic acid is selectively oxidized by a specific oxidant, so that the non-esterified galacturonic acid is degraded, the molecular chain skeleton of pectin is broken, and low-molecular-weight high-esterification pectin with higher methyl-esterified galacturonic acid content is formed.
Description
Technical Field
The invention belongs to the technical field of biological pharmacy, and particularly relates to high-ester pectin containing an active aldehyde group structure and a preparation method thereof.
Background
Pectin molecules are an anionic heteropolysaccharide that is ubiquitously distributed in the cell walls of higher plants. Pectin can be classified into high esterification degree pectin (DM > 50%) and low esterification degree pectin (DM < 50%) according to the extent of galacturonic acid esterification in pectin. The degree of esterification of pectin is a key parameter affecting the functionality of pectin, especially the gelling mechanism and the gelling properties. In addition, the high-ester pectin contains a high proportion of hydrophobic methyl esterification groups, so that the emulsifying capacity of the molecule is enhanced. The traditional preparation of high ester pectin is based on heat/acid extraction, which limits the saponification of methyl esterified galacturonic acid, but the esterification degree of the obtained pectin is generally about 70%. To further increase the methyl esterification degree of pectin, methanol is generally used for esterification with the carboxyl groups of pectin.
CN113731307A discloses an ammonium sulfate-containing high-ester pectin gel, and a preparation method and application thereof, specifically disclosing the following methods: 1) Dissolving high-ester pectin in water, and adjusting the pH value to 4-7 to obtain 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 uses ammonium sulfate, so that the product has great limitation and space for improvement is provided.
CN102643366A discloses a method for intermittently extracting high ester pectin precipitated by ethanol with acid, which specifically discloses a method for soaking dried orange peel in warm water at 45 ℃ for 30min to make it fully absorb water and soften to remove soluble impurities, draining the orange peel, putting the dried orange peel into boiling water to inactivate enzyme, rinsing the orange peel after inactivation of enzyme in running water to colorless, then crushing the orange peel by a crusher, and mixing the crushed orange peel particles and water according to the mass ratio, namely the orange peel particles: 1 part of water: 5-20, controlling the pH value to be 1.0-3.0, controlling the temperature to be 50-90 ℃, extracting for 30-90min, filtering, performing vacuum rotary evaporation on the filtrate, adding absolute ethanol into the obtained concentrated solution, precipitating, performing suction filtration, and drying the obtained filter cake at 40 ℃ to obtain the high-ester pectin. The preparation method of the technical scheme is simple, but the esterification degree of the obtained pectin is not high, and the improvement space exists.
In review, the prior art is still lacking in a process for preparing oxidized pectin having a high degree of simple esterification.
Disclosure of Invention
Aiming at the defects or the improvement requirements of the prior art, the invention provides high-ester pectin containing an active aldehyde group structure and a preparation method thereof, aiming at selectively oxidizing ortho-dihydroxy of non-esterified galacturonic acid by using a specific oxidant, so that the non-esterified galacturonic acid is degraded, the molecular chain skeleton of the pectin is broken, low-molecular-weight high-esterification pectin with higher methyl-esterified galacturonic acid content is formed, and finally the high-esterification-degree oxidized pectin is obtained by the simple preparation method.
In order to achieve the above object, according to one aspect of the present invention, there is provided a method for preparing a high ester pectin containing an active aldehyde structure, comprising the steps of:
(1) Fully dissolving pectin to obtain pectin solution, and adding alkali to adjust pH to below 5.0;
(2) Adding a specific oxidant for light-resistant reaction, wherein the specific oxidant can selectively oxidize the o-dihydroxy of the non-esterified galacturonic acid, promote the degradation of the non-esterified galacturonic acid and break the molecular chain skeleton of the pectin to obtain the high-ester pectin containing an active aldehyde group structure;
(3) Adding a terminator to terminate the reaction, then carrying out alcohol precipitation on the reaction solution through ethanol, separating an alcohol precipitation product, and freeze-drying to obtain the pectin oxide.
Preferably, the specific oxidizer is at least one of sodium periodate, hydrogen peroxide, sodium hypochlorite and potassium chlorate.
Preferably, the specific oxidizing agent is sodium periodate.
Preferably, the mass ratio of the specific oxidant to pectin is (0.01-0.1): 1, preferably 0.04:1.
preferably, the mass concentration of the pectin solution in the step (1) is 1.0-2.5%.
Preferably, the pH of the pectin solution in step (1) is 4.0-5.0.
Preferably, the pectin is at least one of lemon peel pectin, orange peel pectin and apple peel pectin.
Preferably, the terminator is ethylene glycol or polyethylene glycol.
Preferably, the reaction time is preferably 12h to 24h.
According to another aspect of the present invention, there is provided a method for preparing oxidized pectin, which has the following beneficial effects:
(1) The invention selects periodate as oxidant, has high specific selective oxidation ability, has no obvious side reaction, and can make C on galacturonic acid 2 -C 3 The bond is broken to convert the original ortho-dihydroxy group into a dialdehyde group with high reducibility. The non-esterified galacturonic acid becomes more prone to oxidation sites, which in turn leads to a change in the degree of esterification. Therefore, the method can prepare aldehyde pectin with higher activity, reduce the molecular weight and improve the esterification degree of pectin.
(2) The esterification degree of the oxidized pectin obtained by the method can be higher than 94%, and the method does not need complex esterification reaction, thereby greatly enriching the application range of the pectin.
Drawings
FIG. 1 is a graph showing the molecular weight distribution test of pectins of examples 1 to 2 and comparative example;
FIG. 2 molecular morphology test charts of pectin of examples 1-2 and comparative example;
FIG. 3 is a graph showing the results of the degree of esterification and the aldehyde group content tests of examples 1-2 and comparative example.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further 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 respective embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
Examples
The high esterified orange peel pectin used in the following manufacturing example was purchased from lime biotech ltd, guangzhou. The apparatus used in the examples: scanning probe atomic force microscope Multi-mode 8 and HPLC Waters e2695.
1. And (3) determining the aldehyde group content of pectin: reference "modified pectin" Molecular characterization, qualitative change and gel property "aqueous pectin solution (2.0%, pH 3.0) or ethanolic pectin solution (25%, v/v) was diluted to 5. Mu.g/mL with the corresponding solvent. mu.L of the above solution was applied to a clean mica plate and thoroughly dried in a desiccator.
The experimental conditions are as follows: the scanning speed is 1.0Hz, and the driving frequency is 300KHz. Sample images were obtained in the tracking mode and processed with Nano Analysis software. Rheological testing of pectin gels
2. And (3) measuring the molecular weight: the reference "Structural characterization, antigenic and immunological activities of a polysaccharide from Boletus leculae". Dissolving pectin sample in 20mm KH 2 PO 4 And (3) fully dissolving the buffer solution, and filtering by using a 0.22 mu m microporous filter membrane to obtain a pectin solution with the concentration of 2-5 mg/mL. The molecular weight of the pectin sample was identified by testing the pectin sample with dextran standards (4.4, 9.9,21.4,43.5,124,196,277, and 401 kDa) in a Waters gel permeation chromatography system and plotting a molecular weight standard curve based on the molecular weight and the time to peak of the dextran standard.
The chromatographic method comprises the following steps: the Ultra hydrogel 1000 (7.8X 300 mm) and the Ultra hydrogel500 (7.8X 300 mm) were connected in series, the mobile phase was 20mm KH2PO4 buffer solution, the flow rate was 0.8mL/min, the detection was performed by a Waters 2414 differential detector, and the column temperature was 35 ℃.
3. And (3) measuring the degree of esterification: reference is made to "Lenprine. Degree of esterification and molecular weight of pectin versus Pb 2+ Influence of adsorption Properties [ D]"proceed, weigh 50mg of pectin sample into 250mL Erlenmeyer flask, add 100mL CO-free 2 The bottle stopper is tightly plugged with the water, and the water is continuously shaken to completely dissolve the pectin sample. Then phenolphthalein indicator was added, and the solution was titrated to reddish with 0.02mol/L NaOH standard solution, and the volume of NaOH consumed (V1) was recorded. Further, 20.00mL of a 0.5mol/L NaOH standard solution was added, the stopper was tightly closed, and the mixture was shaken for 15min, followed by adding an equimolar 0.5mol/L HCl standard solution and sufficiently shaking again. Finally phenolphthalein indicator was added, titrated to reddish with 0.02mol/L NaOH standard solution, and the volume of NaOH consumed (V2) was recorded. The pectin esterification degree is calculated as follows:
esterification du (%) = V2/(V1 + V2) × 100
4. And (3) determining the aldehyde group content: according to the reference of the document "Liuwenyin, preparation of the oxidized cellulose/chitosan composite hemostatic material and performance research [ D ]", a certain amount of oxidized pectin is weighed, a certain volume of 0.25M hydroxylamine hydrochloride-methyl orange solution is added, and the mixture is fully stirred for 4 hours. Finally, titration with 0.1M standard NaOH solution until the solution color changes from pink to yellow, which titrates the global pH 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 unit of aldehyde group content [ CHO ] 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.
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;
(2) Adding solid sodium periodate into the pectin solution under the condition of keeping out of the sun, so that the mass concentration of pectin and periodic acid in the solution reaches 50:1, adding periodic acid and continuously stirring pectin solution to react;
(3) After reacting for 12h, 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 obtain the oxidized pectin.
Example 2
This example differs from example 1 in the quality comparison of the oxidizing agent and pectin.
(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 4.0;
(2) Adding solid sodium periodate into the pectin solution under the condition of keeping out of the light, so that the concentration of pectin and periodic acid in the solution reaches 10:1, adding periodic acid and continuously stirring pectin solution to react;
(3) After reacting for 12h, adding 10mL of ethylene glycol to terminate 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 obtain the oxidized pectin.
Example 3
This example differs from example 1 in the quality comparison of the oxidizing agent and pectin.
(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 4.0;
(2) Adding solid sodium periodate into the pectin solution under the condition of keeping out of the light, so that the concentration of pectin and periodic acid in the solution reaches 100:1, adding periodic acid and continuously stirring pectin solution to react;
(3) After reacting for 12h, adding 10mL of ethylene glycol to terminate 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 obtain the oxidized pectin.
Example 4
This example differs from example 1 in the quality comparison of the oxidizing agent and pectin.
(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 4.0;
(2) Adding solid sodium periodate into the pectin solution under the condition of keeping out light, so that the concentration of pectin and periodic acid in the solution reaches 25:1, adding periodic acid and continuously stirring pectin solution to react;
(3) After reacting for 12h, 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 obtain the oxidized pectin.
Example 5
This example differs from example 1 in that the oxidizing agent is different.
(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 4.0;
(2) Adding hydrogen peroxide into the pectin solution under the condition of keeping out light, so that the concentration of pectin and periodic acid in the solution reaches 10:1, adding periodic acid and continuously stirring pectin solution to react;
(3) After reacting for 12h, adding 10mL of ethylene glycol to terminate 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 obtain the oxidized pectin.
Example 6
This example differs from example 5 in the quality comparison of the oxidizing agent and pectin.
(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 4.0;
(2) Adding hydrogen peroxide into the pectin solution under the condition of keeping out of the light, so that the concentration of the pectin and periodic acid in the solution reaches 100:1, adding periodic acid and continuously stirring pectin solution to react;
(3) After reacting for 12h, adding 10mL of ethylene glycol to terminate 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 obtain the oxidized pectin.
Example 7
This example differs from example 1 in that the oxidizing agent is different.
(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 4.0;
(2) Adding sodium hypochlorite into the pectin solution under the condition of keeping out of the light, so that the concentration of pectin and periodic acid in the solution reaches 10:1, adding periodic acid and continuously stirring pectin solution for reaction;
(3) After reacting for 12h, 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 obtain the oxidized pectin.
Example 8
This example differs from example 7 in the quality comparison of the oxidizing agent and pectin.
(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 4.0;
(2) Adding sodium hypochlorite into the pectin solution under the condition of keeping out of the light, so that the concentration of pectin and periodic acid in the solution reaches 100:1, adding periodic acid and continuously stirring pectin solution for reaction;
(3) After reacting for 12h, 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 obtain the oxidized pectin.
Comparative example
This example differs from example 1 in that no oxidant was added.
(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 4.0;
(2) Adding no sodium periodate, stirring for 12h, adding 10mL of ethylene glycol to terminate oxidation reaction, pouring the pectin solution into 3 times volume of absolute ethyl alcohol for precipitation, repeating the steps for 3 times, and finally freeze-drying to obtain the oxidized pectin.
TABLE 1 esterification degree test results for examples 1-8
| Examples | Oxidizing agent | Mass ratio (pectin: oxidant) | Degree of esterification |
| Example 1 | Sodium periodate | 50：1 | 94.52％ |
| Example 2 | Sodium periodate | 10：1 | 86.03％ |
| Example 3 | Sodium periodate | 100：1 | 94.70％ |
| Example 4 | Sodium periodate | 25：1 | 94.13％ |
| Example 5 | Hydrogen peroxide | 10：1 | 63.98％ |
| Example 6 | Hydrogen peroxide | 100：1 | 56.53％ |
| Example 7 | Sodium hypochlorite | 10：1 | 64.64％ |
| Example 8 | Sodium hypochlorite | 100：1 | 57.85％ |
| Comparative example | Is composed of | \ | 58.97％ |
Analyzing the data in table 1 shows that: the oxidant of the present invention has high specific selective oxidation capacity and no obvious side reaction, and can break the C2-C3 bond of galacturonic acid to convert the original ortho-dihydroxy into dialdehyde radical with high reducibility. The non-esterified galacturonic acid becomes more prone to oxidation sites, which in turn leads to a change in the degree of esterification. Therefore, the method can prepare aldehyde pectin with higher activity, reduce the molecular weight and improve the esterification degree of the pectin.
The periodate has the best effect, the esterification degree of the obtained oxidized pectin can be higher than 94%, complex esterification reaction is not needed, and the application range of the pectin is greatly expanded.
FIG. 1 is a molecular weight distribution test chart of pectins of examples 1 to 2 and a comparative example;
FIG. 2 molecular morphology test charts of pectins of examples 1 to 2 and comparative example;
FIG. 3 is a graph showing the results of the degree of esterification and the aldehyde group content tests of examples 1-2 and comparative example.
As can be seen from FIGS. 1 and 2, the molecular chains of the oxidized pectins prepared according to the invention (examples 1 and 2) are significantly shorter and the molecular weights are significantly lower than those of the unoxidized pectins (comparative examples). While figure 3 shows that the oxidative modification of the present invention significantly increases the aldehyde content and the degree of esterification of pectin, and that the degree of esterification decreases at higher oxidation levels, the preferred oxidation conditions for this study can produce low molecular weight, high ester pectins containing active aldehyde groups.
It will be understood by those skilled in the art that the foregoing is only a preferred embodiment of the present invention, and is not intended to limit the invention, and that any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. A preparation method of high ester pectin containing an active aldehyde group structure is characterized by comprising the following steps:
(1) Fully dissolving pectin to obtain pectin solution, and adding alkali to adjust pH to below 5.0;
(2) Adding a specific oxidant for light-resistant reaction, wherein the specific oxidant can selectively oxidize the o-dihydroxy of the non-esterified galacturonic acid, promote the degradation of the non-esterified galacturonic acid and break the molecular chain skeleton of the pectin to obtain the high-ester pectin containing an active aldehyde group structure;
(3) Adding a terminator to terminate the reaction, then carrying out alcohol precipitation on the reaction solution through ethanol, separating an alcohol precipitation product, and freeze-drying to obtain the pectin oxide.
2. The method for preparing oxidized pectin according to claim 1, wherein the specific oxidizing agent is at least one of sodium periodate, hydrogen peroxide, sodium hypochlorite and potassium chlorate.
3. A method of preparing oxidized pectin according to claim 2, characterized in that said specific oxidizing agent is sodium periodate.
4. A method of preparing oxidized pectin according to claim 2, wherein the mass ratio of said specific oxidizing agent to pectin is (0.01-0.1): 1, preferably 0.04:1.
5. the method for preparing oxidized pectin according to claim 1, wherein the mass concentration of the pectin solution in step (1) is 1.0% -2.5%.
6. A process for the preparation of oxidized pectin according to claim 1 or 5, wherein the pH of the pectin solution in step (1) is between 4.0 and 5.0.
7. A method of preparing oxidized pectin according to claim 1, wherein the pectin is at least one of lemon peel pectin, orange peel pectin and apple peel pectin.
8. The method for preparing oxidized pectin according to claim 1, wherein the terminator is ethylene glycol or polyethylene glycol.
9. A process for the preparation of oxidized pectin according to claim 1, characterized in that the reaction time is preferably 12-24 h.
10. A high ester pectin containing an active aldehyde group structure prepared by the method for preparing oxidized pectin according to any one of claims 1-9.
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|---|---|---|---|---|
| JP2001335532A (en) * | 2000-05-23 | 2001-12-04 | Seiko Epson Corp | Method for producing polygalacturonic acid |
| CN106118560A (en) * | 2016-07-03 | 2016-11-16 | 陈毅忠 | A kind of preparation method of high cohesive force paper-plastic stick adhesive |
| CN106835367A (en) * | 2017-02-23 | 2017-06-13 | 东北师范大学 | A kind of cross-linked polysaccharides fiber and preparation method thereof |
| CN113015800A (en) * | 2018-08-17 | 2021-06-22 | 塞弗德公司 | Nucleic acid isolation and related methods |
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- 2022-08-03 CN CN202210928451.6A patent/CN115160452A/en active Pending
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|---|---|---|---|---|
| JP2001335532A (en) * | 2000-05-23 | 2001-12-04 | Seiko Epson Corp | Method for producing polygalacturonic acid |
| CN106118560A (en) * | 2016-07-03 | 2016-11-16 | 陈毅忠 | A kind of preparation method of high cohesive force paper-plastic stick adhesive |
| CN106835367A (en) * | 2017-02-23 | 2017-06-13 | 东北师范大学 | A kind of cross-linked polysaccharides fiber and preparation method thereof |
| CN113015800A (en) * | 2018-08-17 | 2021-06-22 | 塞弗德公司 | Nucleic acid isolation and related methods |
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