CN116003883B - Beta-cyclodextrin coated chitosan oligosaccharide and preparation method thereof - Google Patents
Beta-cyclodextrin coated chitosan oligosaccharide and preparation method thereof Download PDFInfo
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- CN116003883B CN116003883B CN202310070855.0A CN202310070855A CN116003883B CN 116003883 B CN116003883 B CN 116003883B CN 202310070855 A CN202310070855 A CN 202310070855A CN 116003883 B CN116003883 B CN 116003883B
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Abstract
The invention belongs to the field of beta-cyclodextrin inclusion compound preparation, and discloses beta-cyclodextrin coated chitosan oligosaccharide and a preparation method thereof. The preparation method comprises the following steps of firstly facing the mass percentAdding beta-cyclodextrin into chitosan hydrochloride solution with the specific concentration of 2.0% -5.0%, so that the mass percentage concentration ratio of the chitosan hydrochloride solution to the beta-cyclodextrin in the mixed solution is 1:1; and adding chitosanase to obtain the beta-cyclodextrin coated chitosan oligosaccharide. The preparation method has simple operation and low risk, and the used medicine is nontoxic and harmless, can effectively inhibit the brown stain of chitosan oligosaccharide, and avoids Mn in the prior art 2+ The injury to human body is suitable for large-scale application in industrial production. The beta-cyclodextrin coated chitosan oligosaccharide obtained by the preparation method has low color value, high yield, no toxicity and no harm, and effectively solves the problems of low general purity, poor quality and low biological activity of the chitosan oligosaccharide.
Description
Technical Field
The invention belongs to the field of beta-cyclodextrin inclusion compound preparation, and in particular relates to beta-cyclodextrin coated chitosan oligosaccharide and a preparation method thereof.
Background
The chitosan oligosaccharide, also called as chitosan oligosaccharide and oligomeric chitosan, is an oligosaccharide product with polymerization degree of 2-10 obtained by a special biological enzyme degradation technology, a chemical degradation technology or a microwave degradation technology, and is a low molecular weight product with good water solubility, large function and high bioactivity. Compared with chitosan, the chitosan oligosaccharide has higher solubility and is easy to be absorbed and utilized by organisms.
However, since the chitosan oligosaccharide is an oligosaccharide with positive charge and positive cation basic amino groups, and the structure of the chitosan oligosaccharide contains a large amount of amino groups, maillard reaction is easy to occur, so that the color of the chitosan oligosaccharide solution is gradually deepened along with the increase of reaction time, and the browning degree is continuously increased. The brown stain of chitosan oligosaccharide can reduce the purity of the chitosan oligosaccharide, affect the quality of products, and reduce the bioactivity of the chitosan oligosaccharide. The chitosan oligosaccharide sold in the market at present has the common problems of over-high browning degree, over-deep color of products and the like, and the popularization and application of the chitosan oligosaccharide and related products are limited, so that how to inhibit the browning of the chitosan oligosaccharide becomes a key problem. The addition of Mn-containing solutions to chitosan oligosaccharide solutions has been reported in the prior art 2+ When the concentration of the chitosan oligosaccharide solution reaches a range, the browning of the chitosan oligosaccharide can be effectively inhibited. But the obtained chitosan oligosaccharide contains Mn 2+ Belongs to heavy metal ions, has potential safety risk, and can cause chronic poisoning after long-term intake, thereby causing injury to human bodies.
Disclosure of Invention
The invention aims to solve the defects in the prior art and provides beta-cyclodextrin coated chitosan oligosaccharide and a preparation method thereof, and the preparation method specifically adopts the following technical scheme:
the preparation method of the beta-cyclodextrin coated chitosan oligosaccharide comprises the following steps:
firstly, adding beta-cyclodextrin into a chitosan hydrochloride solution with the mass percent concentration of 2.0% -5.0%, and uniformly mixing to ensure that the mass percent concentration ratio of the chitosan hydrochloride solution to the beta-cyclodextrin in a mixed solution is 1:1; and adding chitosan enzyme, stirring until the enzymolysis is sufficient, inactivating the enzyme, filtering and drying to obtain the beta-cyclodextrin coated chitosan oligosaccharide.
The inventor of the invention provides a method for preparing beta-cyclodextrin coated chitosan oligosaccharide, which ensures that chitosan oligosaccharide generated in the enzymolysis process of chitosan hydrochloride is immediately coated by beta-cyclodextrin in a ratio of 1:1 by reasonably setting the mass percent concentration of chitosan hydrochloride and beta-cyclodextrin, thereby effectively inhibiting the browning of the chitosan oligosaccharide and preparing the beta-cyclodextrin coated chitosan oligosaccharide with low color value. The stabilizer adopted by the invention is beta-cyclodextrin, so that Mn in the method used in the prior art is avoided 2+ The preparation method is simple to operate, low in risk, and the used beta-cyclodextrin is low in price, safe and easy to obtain as a food additive, and is more suitable for being applied to industrial production on a large scale.
The chitosan hydrochloride is adopted in the invention, and various chitosan organic acid salts are not selected, because various organic acids contain carbonyl groups and easily undergo Maillard reaction with amino groups of chitosan oligosaccharide; and other chitosan inorganic acid salts are not selected, because the salts formed by chitosan and divalent or higher inorganic acid are generally difficult to dissolve in water and cannot be used as a proper enzymolysis substrate, the chitosan monovalent inorganic acid salt, in particular the chitosan hydrochloride, is used as the optimal choice. The beta-cyclodextrin adopted by the method is a cyclic compound formed by combining 7 glucose residues through beta-1, 4-glycosidic bonds, and has the advantages of no toxicity, no harm, no side effect and the like. The mass percentage concentration ratio of the chitosan hydrochloride solution and the beta-cyclodextrin in the mixed solution is controlled to be 1:1, so that the beta-cyclodextrin molecules coat the chitosan oligosaccharide molecules 1:1 generated by enzymolysis, and the sufficient coating of the chitosan oligosaccharide can be realized. If the concentration of chitosan hydrochloride is too high, the viscosity of a reaction system is too high, insufficient enzymolysis is easily caused, and the quality of chitosan oligosaccharide is reduced; if the concentration of chitosan hydrochloride is too low, the concentration of chitosan oligosaccharide which is an enzymolysis product can be reduced, and the time and energy consumption of subsequent spray drying can be increased. If the concentration of beta-cyclodextrin is too high, the quantity of beta-cyclodextrin is too high, and an excessive part of beta-cyclodextrin does not actually coat chitosan oligosaccharide, so that the waste of beta-cyclodextrin is caused; if the concentration of beta-cyclodextrin is too low, the dosage of beta-cyclodextrin is insufficient, and complete coating of all chitosan oligosaccharide molecules can not be realized, and the part of chitosan oligosaccharide which is not coated is still easy to brown.
Therefore, the mass percent concentration of the chitosan hydrochloride and the beta-cyclodextrin is regulated to be in a proper range, and a reasonable proportion is achieved, so that the browning of the chitosan oligosaccharide can be effectively inhibited, and the yield of the chitosan oligosaccharide can be improved.
Preferably, the chitosan hydrochloride is low-viscosity chitosan hydrochloride, medium-viscosity chitosan hydrochloride or high-viscosity chitosan hydrochloride. More preferably, the chitosan hydrochloride is a low viscosity chitosan hydrochloride having a viscosity of less than 200 mpa.s. The reason why the low-viscosity chitosan hydrochloride with the viscosity lower than 200 mPas is most preferred in the invention is that the polymerization degree and the molecular weight are lower compared with the high-viscosity chitosan hydrochloride with the viscosity higher than 400 mPas and the medium-viscosity chitosan hydrochloride with the viscosity between 200 mPas and 400 mPas, so that the chitosan oligosaccharide can be obtained more rapidly under the same enzymolysis condition, the enzymolysis time is shortened, and the browning degree is reduced.
Preferably, the chitosan hydrochloride is derived from shrimp, crab or insect shells. A large amount of chitin exists in the crustaceans of shrimps, crabs and insects, the product obtained by removing more than 55% of N-acetyl groups from the chitin is chitosan, and then the chitosan is dissolved in hydrochloric acid with a certain concentration and dried to obtain chitosan hydrochloride.
Preferably, after the chitosanase is added into the mixed solution, the mass percentage concentration of the chitosanase is 0.002% -0.005%. The chitosan enzyme has high price, and the addition amount of the chitosan enzyme is reasonably set, so that the full enzymolysis of chitosan hydrochloride can be realized, and the production cost can be controlled.
Preferably, the stirring is carried out at a constant temperature of 30-50 ℃. The optimum temperature of chitosanase is 65 ℃, but the research shows that the generated chitosan oligosaccharide is easy to brown at the too high enzymolysis temperature, so that the enzymolysis temperature is most suitable to be controlled at 30-50 ℃.
Preferably, the chitosan oligosaccharide solution obtained after enzymolysis is heated to 80 ℃ to inactivate enzyme, filtered while hot, and spray-dried after removing suspended matters.
The invention also provides the beta-cyclodextrin coated chitosan oligosaccharide prepared by the preparation method, which has the color value lower than 240IU, can reach the color value level of secondary white granulated sugar, has the yield of more than 90 percent, and is a chitosan oligosaccharide product with good stability, no toxicity and harm and good quality.
The beneficial effects of the invention are as follows: the preparation method adopted in the invention has simple operation and low risk, and the used medicines have low price, are nontoxic and harmless, can effectively inhibit the brown stain of chitosan oligosaccharide, and avoid Mn in the methods used in the prior art 2+ The injury to human body is suitable for large-scale application in industrial production. The beta-cyclodextrin coated chitosan oligosaccharide obtained by the preparation method has low color value, high yield, no toxicity and no harm, and effectively solves the problems of low general purity, poor quality and low biological activity of the chitosan oligosaccharide.
Detailed Description
The conception and technical effects of the present invention will be clearly and completely described in conjunction with examples below to fully understand the objects, aspects and effects of the present invention. It should be noted that, in the case of no conflict, the embodiments and features in the embodiments may be combined with each other.
Example 1
The preparation method of the beta-cyclodextrin coated chitosan oligosaccharide specifically comprises the following steps:
s1, weighing 10g of chitosan hydrochloride, wherein the chitosan hydrochloride is derived from crayfish shells, adding 500mL of deionized water to enable the mass percentage of a chitosan hydrochloride solution to be 2%, and placing the chitosan hydrochloride into a water bath kettle with a constant temperature of 40 ℃ to be stirred until the chitosan hydrochloride is completely dissolved to form a clear chitosan hydrochloride solution;
s2, adding 10g of beta-cyclodextrin solid powder into the chitosan hydrochloride solution obtained in the S1, enabling the mass percentage of the beta-cyclodextrin to be 2%, and stirring for 2 hours at a constant temperature of 40 ℃ to enable the beta-cyclodextrin to be fully dissolved, so as to obtain a mixed solution of chitosan hydrochloride and beta-cyclodextrin;
s3, adding chitosan enzyme into the mixed solution of chitosan hydrochloride and beta-cyclodextrin obtained in the S2, and stirring at the constant temperature of 40 ℃ for 12 hours until the chitosan enzyme is fully hydrolyzed to generate a chitosan oligosaccharide solution, wherein the mass percentage concentration of the chitosan enzyme is 0.003%;
s4, heating the chitosan oligosaccharide solution obtained in the step S3 to 80 ℃ to inactivate enzyme, filtering while the chitosan oligosaccharide solution is hot, and removing suspended matters to obtain a clarified chitosan oligosaccharide solution;
s5, spray drying to obtain 18.06g of beta-cyclodextrin coated chitosan oligosaccharide, wherein the yield is 90.3%.
The color value of the beta-cyclodextrin-coated chitosan oligosaccharide obtained in this example was determined according to the following procedure:
(1) 10.00g of the beta-cyclodextrin coated chitosan oligosaccharide sample is weighed into a 250mL beaker, 200mL of distilled water is added, the mixture is stirred until the mixture is completely dissolved, the mixture is transferred to a 250mL volumetric flask, and distilled water is used for volume fixing.
(2) Pouring into a filter with a pore size of 0.45 μm, vacuum filtering, discarding about 50mL of the first filtrate, and collecting filtrate with a concentration of not less than 50mL.
(3) The filtrate was placed in a cuvette, zeroed with distilled water, and its absorbance was measured on a spectrophotometer at a wavelength of 420 nm. The color value of the sample is calculated as IU according to the following formula.
Wherein CV is a color value (IU), A is absorbance of the filtrate measured at a wavelength of 420nm, b is cuvette thickness (cm), and c is sample solution concentration (g/mL).
The measurement result shows that the color value of the beta-cyclodextrin coated chitosan oligosaccharide obtained in the embodiment is 195IU.
Example 2
The preparation method of the beta-cyclodextrin coated chitosan oligosaccharide changes the dosage and the source of chitosan hydrochloride, the mass percent concentration of the beta-cyclodextrin and the stirring temperature and the stirring time, and specifically comprises the following steps:
s1, weighing 15g of chitosan hydrochloride, wherein the chitosan hydrochloride is derived from Alaska snow crab shells, adding 500mL of deionized water to enable the mass percentage of a chitosan hydrochloride solution to be 3%, placing the chitosan hydrochloride into a water bath kettle with a constant temperature of 45 ℃, and stirring until the chitosan hydrochloride is completely dissolved to form a clear chitosan hydrochloride solution;
s2, adding 15g of beta-cyclodextrin solid powder into the chitosan hydrochloride solution obtained in the S1, enabling the mass percentage of the beta-cyclodextrin solution to be 3%, and stirring for 2 hours at the constant temperature of 45 ℃ to enable the beta-cyclodextrin to be fully dissolved, so as to obtain a mixed solution of the chitosan hydrochloride and the beta-cyclodextrin;
s3, adding chitosan enzyme into the mixed solution of chitosan hydrochloride and beta-cyclodextrin obtained in the S2, and stirring at the constant temperature of 45 ℃ for 12 hours until the chitosan enzyme is fully hydrolyzed to obtain a chitosan oligosaccharide solution, wherein the mass percentage concentration of the chitosan enzyme is 0.003%;
s4, heating the chitosan oligosaccharide solution obtained in the step S3 to 80 ℃ to inactivate enzyme, filtering while the chitosan oligosaccharide solution is hot, and removing suspended matters to obtain a clear chitosan oligosaccharide solution;
s5, spray drying to obtain 27.24g of beta-cyclodextrin coated chitosan oligosaccharide, wherein the yield is 90.8%.
The color value of the beta-cyclodextrin-coated chitosan oligosaccharide obtained in this example was determined according to the following procedure:
(1) 10.00g of the beta-cyclodextrin coated chitosan oligosaccharide sample is weighed into a 250mL beaker, 200mL of distilled water is added, the mixture is stirred until the mixture is completely dissolved, the mixture is transferred to a 250mL volumetric flask, and distilled water is used for volume fixing.
(2) Pouring into a filter with a pore size of 0.45 μm, vacuum filtering, discarding about 50mL of the first filtrate, and collecting the filtrate.
(3) The filtrate was placed in a cuvette, zeroed with distilled water, and its absorbance was measured on a spectrophotometer at a wavelength of 420 nm. The color value of the sample is calculated as IU according to the following formula.
Wherein CV is a color value (IU), A is absorbance of the filtrate measured at a wavelength of 420nm, b is cuvette thickness (cm), and c is sample solution concentration (g/mL).
The measurement result shows that the color value of the beta-cyclodextrin coated chitosan oligosaccharide obtained in the example is 189IU.
Example 3
The preparation method of the beta-cyclodextrin coated chitosan oligosaccharide changes the dosage and the source of chitosan hydrochloride, the mass percent concentration of the beta-cyclodextrin and the chitosan enzyme, and the stirring temperature and the stirring time, and specifically comprises the following steps:
s1, weighing 20g of chitosan hydrochloride, wherein the chitosan hydrochloride is derived from cicada slough, adding 500mL of deionized water to enable the mass percentage of a chitosan hydrochloride solution to be 4%, placing the chitosan hydrochloride into a water bath kettle with a constant temperature of 45 ℃, and stirring until the chitosan hydrochloride is completely dissolved to form a clear chitosan hydrochloride solution;
s2, adding 20g of beta-cyclodextrin solid powder into the chitosan hydrochloride solution obtained in the S1 to enable the mass percentage of the beta-cyclodextrin solution to be 4%, and continuously stirring at the constant temperature of 45 ℃ for 2 hours to enable the beta-cyclodextrin to be fully dissolved to obtain a mixed solution of the chitosan hydrochloride and the beta-cyclodextrin;
s3, adding chitosan enzyme into the mixed solution of chitosan hydrochloride and beta-cyclodextrin obtained in the S2, and stirring at the constant temperature of 45 ℃ for 12 hours until the enzymolysis is complete, so as to obtain a chitosan oligosaccharide solution, wherein the mass percentage concentration of the chitosan enzyme is 0.004%;
s4, heating the chitosan oligosaccharide solution obtained in the step S3 to 80 ℃ to inactivate enzyme, filtering while the chitosan oligosaccharide solution is hot, and removing suspended matters to obtain a clarified chitosan oligosaccharide solution;
s5, spray drying to obtain 36.65g of beta-cyclodextrin coated chitosan oligosaccharide, wherein the yield is 91.6%.
The color value of the beta-cyclodextrin-coated chitosan oligosaccharide obtained in this example was determined according to the following procedure:
(1) 10.00g of the beta-cyclodextrin coated chitosan oligosaccharide sample is weighed into a 250mL beaker, 200mL of distilled water is added, the mixture is stirred until the mixture is completely dissolved, the mixture is transferred to a 250mL volumetric flask, and distilled water is used for volume fixing.
(2) Pouring into a filter with a pore size of 0.45 μm, vacuum filtering, discarding about 50mL of the first filtrate, and collecting filtrate with a concentration of not less than 50mL.
(3) The filtrate was placed in a cuvette, zeroed with distilled water, and its absorbance was measured on a spectrophotometer at a wavelength of 420 nm. The color value of the sample is calculated as IU according to the following formula.
Wherein CV is a color value (IU), A is absorbance of the filtrate measured at a wavelength of 420nm, b is cuvette thickness (cm), and c is sample solution concentration (g/mL).
The measurement result shows that the color value of the beta-cyclodextrin coated chitosan oligosaccharide obtained in the example is 203IU.
Comparative example 1
The preparation method of the beta-cyclodextrin coated chitosan oligosaccharide is different from example 2 in that the mass percent concentration of the chitosan hydrochloride solution and the beta-cyclodextrin is increased, and specifically comprises the following steps:
s1, weighing 30g of chitosan hydrochloride, wherein the chitosan hydrochloride is derived from Alaska snow crab shells, adding 500mL of deionized water to enable the mass percentage of a chitosan hydrochloride solution to be 6%, placing the chitosan hydrochloride into a water bath kettle with a constant temperature of 45 ℃, and stirring until the chitosan hydrochloride is completely dissolved to form a clear chitosan hydrochloride solution;
s2, adding 30g of beta-cyclodextrin solid powder into the chitosan hydrochloride solution obtained in the S1, wherein the mass percent of the beta-cyclodextrin solution is 6%, stirring for 2 hours at the constant temperature of 45 ℃, and a large amount of suspended matters exist, so that the content of the beta-cyclodextrin is too high, the beta-cyclodextrin exceeds the saturation degree, the beta-cyclodextrin cannot be fully dissolved, and the experiment fails.
Comparative example 2
The preparation method of the beta-cyclodextrin coated chitosan oligosaccharide is different from the embodiment 1 in that the mass percentage concentration ratio of the chitosan hydrochloride solution to the beta-cyclodextrin is changed to 2:1, specifically comprising the following steps:
s1, weighing 10g of chitosan hydrochloride, wherein the chitosan hydrochloride is derived from Alaska snow crab shells, adding 500mL of deionized water to enable the mass percentage of a chitosan hydrochloride solution to be 2%, and placing the chitosan hydrochloride into a water bath kettle with the constant temperature of 45 ℃ to be stirred until the chitosan hydrochloride is completely dissolved to form a clear chitosan hydrochloride solution;
s2, adding 5g of beta-cyclodextrin solid powder into the chitosan hydrochloride solution obtained in the S1, enabling the mass percentage of the beta-cyclodextrin solution to be 1%, and stirring for 2 hours at the constant temperature of 45 ℃ to enable the beta-cyclodextrin to be fully dissolved, so as to obtain a mixed solution of the chitosan hydrochloride and the beta-cyclodextrin;
s3, adding chitosan enzyme into the mixed solution of chitosan hydrochloride and beta-cyclodextrin obtained in the S2, and stirring at the constant temperature of 45 ℃ for 12 hours until the chitosan enzyme is fully hydrolyzed to obtain a chitosan oligosaccharide solution, wherein the mass percentage concentration of the chitosan enzyme is 0.003%;
s4, heating the chitosan oligosaccharide solution obtained in the step S3 to 80 ℃ to inactivate enzyme, filtering while the chitosan oligosaccharide solution is hot, and removing suspended matters to obtain a clear chitosan oligosaccharide solution;
s5, spray drying to obtain 13.42g of beta-cyclodextrin coated chitosan oligosaccharide, wherein the yield is 89.47%.
The color value of the beta-cyclodextrin-coated chitosan oligosaccharide obtained in this example was determined according to the following procedure:
(1) 10.00g of the beta-cyclodextrin coated chitosan oligosaccharide sample is weighed into a 250mL beaker, 200mL of distilled water is added, the mixture is stirred until the mixture is completely dissolved, the mixture is transferred to a 250mL volumetric flask, and distilled water is used for volume fixing.
(2) Pouring into a filter with a pore size of 0.45 μm, vacuum filtering, discarding about 50mL of the first filtrate, and collecting the filtrate.
(3) The filtrate was placed in a cuvette, zeroed with distilled water, and its absorbance was measured on a spectrophotometer at a wavelength of 420 nm. The color value of the sample is calculated as IU according to the following formula.
Wherein CV is a color value (IU), A is absorbance of the filtrate measured at a wavelength of 420nm, b is cuvette thickness (cm), and c is sample solution concentration (g/mL).
The measurement result shows that the color value of the beta-cyclodextrin coated chitosan oligosaccharide obtained in the comparative example is 785IU.
While the present invention has been described in considerable detail and with particularity with respect to several described embodiments, it is not intended to be limited to any such detail or embodiments or any particular embodiment, but is to be construed as providing broad interpretation of such claims by reference to the appended claims in view of the prior art so as to effectively encompass the intended scope of the invention. Furthermore, the foregoing description of the invention has been presented in its embodiments contemplated by the inventors for the purpose of providing a useful description, and for the purposes of providing a non-essential modification of the invention that may not be presently contemplated, may represent an equivalent modification of the invention.
Claims (10)
1. The preparation method of the beta-cyclodextrin coated chitosan oligosaccharide comprises the following steps:
firstly, adding beta-cyclodextrin into a chitosan hydrochloride solution with the mass percent concentration of 2.0% -5.0%, and uniformly mixing to ensure that the mass percent concentration ratio of the chitosan hydrochloride solution to the beta-cyclodextrin in a mixed solution is 1:1; and adding chitosan enzyme, stirring until the enzymolysis is sufficient, inactivating the enzyme, filtering and drying to obtain the beta-cyclodextrin coated chitosan oligosaccharide.
2. The preparation method according to claim 1, wherein the chitosan hydrochloride is a low-viscosity chitosan hydrochloride having a viscosity of less than 200 mPa-s, a medium-viscosity chitosan hydrochloride having a viscosity of 200 mPa-s to 400 mPa-s, or a high-viscosity chitosan hydrochloride having a viscosity of more than 400 mPa-s.
3. The method of claim 2, wherein the chitosan hydrochloride is a low viscosity chitosan hydrochloride.
4. A method of preparation according to claim 3 wherein the chitosan hydrochloride is derived from shrimp, crab or insect shells.
5. The preparation method according to claim 1, wherein the mass percentage concentration of the chitosanase is 0.002% -0.005% after the chitosanase is added to the mixed solution.
6. The method according to claim 1, wherein the stirring is performed at a constant temperature of 30 ℃ to 50 ℃.
7. The method of claim 1, wherein the temperature of enzyme deactivation is 80 ℃.
8. The method of claim 1, wherein the drying is spray drying.
9. A beta-cyclodextrin coated chitosan oligosaccharide, characterized by being prepared by the preparation method of any one of claims 1-8.
10. The beta-cyclodextrin coated chitosan oligosaccharide of claim 9, wherein the beta-cyclodextrin coated chitosan oligosaccharide has a color value of less than 240IU.
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