CN110511135B - Method for adsorbing-separating shikimic acid by adopting chitosan - Google Patents
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Abstract
The invention discloses an adsorption-separation method of shikimic acid, belonging to the technical field of plant purification. The method is implemented according to the following steps: preparing shikimic acid extracting solution from natural plants containing shikimic acid; performing ultrafiltration on shikimic acid extracting solution, and treating by a cation resin column to obtain shikimic acid upper column solution; adding a continuous flow of shikimic acid solution on a column into a chitosan adsorption column for adsorption, washing with 40-80% ethanol solution, eluting with 40-80% ethanol-containing sodium hydroxide solution with the pH value of 8-12 to obtain shikimic acid eluent, treating with a cationic resin column, concentrating, and drying to obtain shikimic acid. According to the invention, under the condition that chitosan does not swell in a shikimic acid solution containing 60% ethanol, shikimic acid in natural plants is effectively adsorbed, and the shikimic acid adsorbed by chitosan is eluted by sodium hydroxide containing ethanol, so that adsorption and separation of shikimic acid are realized, and shikimic acid with purity of 72-82% is finally obtained.
Description
Technical Field
The invention belongs to the technical field of plant purification, and particularly relates to a method for adsorbing and separating shikimic acid by using chitosan.
Background
Shikimic Acid (Shikimic Acid,3R,4S,5R-E-3,4,5-Trihydroxy-l-cyclohexenecarboxylic Acid, CARSN 138-59-0) is a cyclic alcohol derivative, a chiral compound with a single configuration. Shikimic acid has important biological activities of oxidation resistance, bacteriostasis, tumor resistance, inflammation resistance, thrombus resistance, brain nerve cell apoptosis inhibition and the like, and is mainly applied to the following aspects: (1) developing antiviral drugs. Shikimic acid is an intermediate of oseltamivir phosphate which is the main component of an antiviral drug for treating avian influenza. (2) Developing antibacterial and antitumor preparations. The glyoxalase inhibitor analogue synthesized by using shikimic acid methyl ester has obvious inhibition effect on Hela cell strain and Eichiesis ascites carcinoma. (3) Developing the preparation for treating cardiovascular diseases. Shikimic acid has significant antithrombotic effect, and can inhibit formation of thrombus, venous thrombosis and cerebral thrombosis. (4) The development of anti-inflammatory drugs. Shikimic acid can inhibit the expression of inflammatory factors and has an inhibiting effect on inflammatory response.
Currently, shikimic acid is mainly extracted from natural plants although it can be prepared by chemical synthesis or by microbial fermentation. In the prior art, shikimic acid is mainly extracted from the star anise, but the star anise has limited raw material supply, high price, complex production process and low production rate. In addition, a large amount of dangerous chemicals are used, so that serious environmental pollution is caused, and supply and demand of shikimic acid in the market are insufficient, so that a new shikimic acid extraction raw material is imperative to be searched.
Chitosan is a polymer of glucosamine, which is obtained by deacetylation of chitin (chitin) widely existing in nature. Each monomer (glucosamine) of chitosan has a free amino group, the chitosan is insoluble in water, but the free amino group can react with acid (inorganic acid or organic acid) to form salt, so the chitosan has an adsorption effect on the acid, and the molecular weight of each monomer (glucosamine) is close to that of most organic acids, so the chitosan has a strong adsorption capacity on the organic acids. However, chitosan is easily swollen in an acidic aqueous solution and forms a colloidal compound, so that the adsorbed acidic substances (organic acids or inorganic acids) are difficult to separate, and chitosan is also difficult to regenerate, thereby limiting the application thereof in the separation of acidic substances. Therefore, the invention aims to solve the problem that chitosan swells in an acidic aqueous solution and forms a colloidal compound, and the chitosan is used for organic acid adsorption, so that a method for extracting shikimic acid with higher purity is developed, and a technical way is provided for preparing high-purity shikimic acid.
Disclosure of Invention
The invention provides a method for absorbing-separating shikimic acid by chitosan, when absorbing-separating shikimic acid by chitosan, the chitosan is not swelled and does not form colloidal compound, thus leading the absorption-separation of organic acid and the regeneration of chitosan to be possible.
The first purpose of the invention is to provide a method for adsorbing-separating shikimic acid by using chitosan, which is implemented by the following steps:
step 1, preparing shikimic acid extracting solution from natural plants containing shikimic acid;
step 2, treating shikimic acid extracting solution by using a cation resin column to obtain a pretreatment solution; adding the pretreatment solution into an ethanol solution with the volume concentration of 95% to obtain a shikimic acid solution on a column; wherein the volume ratio of the pretreatment solution to the ethanol solution is 37-42%: 58 to 63 percent;
step 3, adding the shikimic acid solution into a chitosan adsorption column, washing the chitosan adsorption column by using an ethanol solution with the volume concentration of 40-80% when the pH value of the effluent is 4.5-5.5, eluting the chitosan adsorption column adsorbed with shikimic acid by using an ethanol-containing sodium hydroxide solution with the pH value of 8-12 when the effluent is washed to be neutral, and collecting the eluent, namely shikimic acid eluent; wherein ethanol in the ethanol-containing sodium hydroxide solution accounts for 40-80% of the total volume;
and 4, treating the shikimic acid eluent by using a cation resin column to obtain a purified treatment solution, and concentrating and drying the purified treatment solution to obtain shikimic acid.
Preferably, the natural plant containing shikimic acid is star anise, pine needle or ginkgo leaf.
Preferably, when the shikimic acid-containing natural plant is star anise, the preparation of shikimic acid extract comprises the following steps: pulverizing fructus Anisi Stellati, sieving, distilling to obtain oleum Foeniculi, cooling the residual solution, concentrating, and diluting to desired volume to obtain shikimic acid extractive solution; wherein, every 100g of the distilled residual solution of the star anise should be metered to 500 mL;
when the natural plant containing shikimic acid is pine needles to prepare shikimic acid extracting solution, the method comprises the following steps: pulverizing folium Pini, adding distilled water, heating under reflux, filtering, and collecting filtrate to obtain shikimic acid extractive solution; wherein, 7500mL of distilled water is needed for heating and refluxing every 300g of pine needles;
when the natural plant containing shikimic acid is ginkgo leaf, the shikimic acid extracting solution is prepared, which comprises the following steps: heating and refluxing folium Ginkgo with 70 vol% ethanol solution, filtering, concentrating, adding distilled water, centrifuging, collecting supernatant, loading onto macroporous resin column, and collecting filtrate to obtain shikimic acid extractive solution, wherein the amount of distilled water is 3L per 1kg of folium Ginkgo put into the tank.
Preferably, in step 2 and step 4, the cation resin column is an LX-04 ion exchange resin column.
Preferably, the preparation method of the chitosan adsorption column comprises the following steps: taking natural cationic polymer chitosan with deacetylation degree of 82-92% and granularity of 40-100 meshes, wetting with 40-95% ethanol solution, and packing to obtain chitosan adsorption column.
Preferably, in step 2, before the shikimic acid extracting solution is treated by the cation resin column, the shikimic acid extracting solution is ultrafiltered by an ultrafiltration membrane of 200 KDa.
Compared with the prior art, the invention has the beneficial effects that:
1) the method utilizes natural cationic polymer chitosan with deacetylation degree of 82-92% and particle size of 40-100 meshes as an adsorbent of shikimic acid, and in order to avoid that the chitosan and organic acid form a colloidal compound in the presence of water and the organic acid is difficult to separate, the volume ratio of a pretreatment solution containing shikimic acid is 37-42%: 58-63% of the shikimic acid is added into 95% of ethanol, so that the chitosan is not swelled in the process of absorbing shikimic acid, and the shikimic acid is ensured to be effectively absorbed on the chitosan;
2) adding shikimic acid solution into a chitosan adsorption column, washing the chitosan adsorption column by using ethanol solution with volume concentration of 40-80% when the pH value of effluent is detected to be 4.5-5.5, and effectively removing other impurities until the effluent is detected to be neutral; and finally, eluting with an ethanol-containing sodium hydroxide solution with the pH value of 8-12 and collecting the eluate, thereby realizing the adsorption and separation of shikimic acid. In addition, in order to avoid swelling of chitosan in the washing and elution processes, ethanol in the washing liquid and the eluent accounts for 40-80% of the volume; meanwhile, the chitosan adsorption column after elution is convenient to regenerate and utilize.
According to the invention, the shikimic acid extracting solution is treated by the LX-04 cation exchange resin column, so that cationic substances such as metal ions, proteins and the like can be effectively removed, and the shikimic acid is completely free; collecting eluent in the elution process of the sodium hydroxide solution containing ethanol, and treating the eluent by an LX-04 cation exchange resin column to effectively remove sodium ions and obtain shikimic acid with the purity of 72-82%.
The method for adsorbing and separating shikimic acid by chitosan can be well applied to the recovery of other organic acids in fermentation liquor and industrial waste liquid.
Detailed Description
In order to make the technical solutions of the present invention better understood and enable those skilled in the art to practice the present invention, the following examples are provided for further illustration, but the present invention is not limited thereto.
The experimental methods described in the following examples are all conventional methods unless otherwise specified; the materials used are commercially available, unless otherwise specified.
Example 1
A method for adsorbing-separating shikimic acid by adopting chitosan is implemented according to the following steps:
step 1, preparing shikimic acid extracting solution from star anise: pulverizing 100g dried fructus Anisi Stellati, sieving with 60 mesh sieve, placing into a distillation flask, adding distilled water, heating, distilling with steam to extract oleum Foeniculi, cooling water extractive solution in the distillation flask, ultrafiltering with 200KDa ultrafiltration membrane, concentrating, and diluting to 500ml to obtain shikimic acid extractive solution;
step 2, treating the shikimic acid extracting solution by an LX-04 ion exchange resin column to obtain a pretreatment solution, and adding the pretreatment solution into an ethanol solution with the volume concentration of 95% to obtain a shikimic acid upper column solution; wherein the volume ratio of the pretreatment solution to the ethanol solution is 37: 63; detecting shikimic acid solution on the column by HPLC, wherein the concentration of shikimic acid is 9.1 mg/mL;
step 3, continuously feeding the shikimic acid solution into a chitosan adsorption column at the flow rate of 5ml/min, washing the chitosan adsorption column by using an ethanol solution with the volume concentration of 40% when the pH value of the effluent is 4.5, eluting the chitosan adsorption column adsorbed with shikimic acid by using an ethanol-containing sodium hydroxide solution with the pH value of 8 when the effluent is neutral, and collecting the eluate, namely shikimic acid eluate;
wherein, ethanol in the sodium hydroxide solution containing ethanol accounts for 40 percent of the total volume; the chitosan adsorption column is prepared by wetting natural cationic polymer chitosan with deacetylation degree of 82% and granularity of 40 meshes by 40% ethanol water solution and then loading the chitosan adsorption column on a column.
Step 4, processing the shikimic acid eluent by using an LX-04 cation resin column to obtain a purified treatment solution, and detecting by HPLC, wherein the shikimic acid content is 8.2mg/ml, and the yield is 90%; finally, concentrating and drying the purified treatment solution to obtain shikimic acid with the purity of 75%.
Example 2
A method for adsorbing-separating shikimic acid by adopting chitosan is implemented according to the following steps:
step 1, preparing shikimic acid extracting solution from pine needles: pulverizing 300g of fresh Pinus koraiensis needle, adding 4500mL of distilled water, heating and refluxing for 2h, filtering, continuously adding 3000mL of distilled water, heating and refluxing for 2h, filtering, and combining the two filtrates to obtain shikimic acid extract;
step 2, performing ultrafiltration on shikimic acid extracting solution by using an ultrafiltration membrane adopting 200KDa, treating the shikimic acid extracting solution by using an LX-04 ion exchange resin column, concentrating the solution to a constant volume of 1000ml to obtain a pretreatment solution, and adding the pretreatment solution into an ethanol solution with a volume concentration of 95% to obtain a shikimic acid upper column solution; wherein the volume ratio of the pretreatment solution to the ethanol solution is 42: 58; detecting shikimic acid solution on the column by HPLC, wherein the concentration of shikimic acid is 8.8 mg/mL;
step 3, continuously feeding the shikimic acid solution into a chitosan adsorption column at the flow rate of 5ml/min, washing the chitosan adsorption column by using an ethanol solution with the volume concentration of 80% when the pH value of the effluent is 5.5, eluting the chitosan adsorption column adsorbed with shikimic acid by using an ethanol-containing sodium hydroxide solution with the pH value of 12 when the effluent is neutral, and collecting the eluate, namely shikimic acid eluate;
wherein, the volume of the ethanol in the sodium hydroxide solution containing the ethanol accounts for 80 percent of the volume; the chitosan adsorption column is prepared by wetting a natural cationic polymer chitosan with deacetylation degree of 95% and granularity of 100 meshes by using 95% ethanol water solution and then loading the chitosan adsorption column on a column.
And 4, treating the shikimic acid eluate by using an LX-04 cation resin column to obtain a purified treatment solution, detecting by HPLC (high performance liquid chromatography) to obtain the shikimic acid with the content of 7.7mg/ml and the yield of 82%, and finally concentrating and drying the purified treatment solution to obtain the shikimic acid with the purity of 72%.
Example 3
A method for adsorbing-separating shikimic acid by adopting chitosan is implemented according to the following steps:
step 1, preparing shikimic acid extracting solution from ginkgo leaves: putting folium Ginkgo into an extraction tank, adding 70% ethanol solution 8 times the volume concentration of folium Ginkgo, heating and refluxing for 2h, filtering, adding 70% ethanol solution 6 times the volume concentration of folium Ginkgo, heating and refluxing for 2h, mixing the two ethanol extractive solutions, and concentrating to remove ethanol to obtain concentrated solution; adding distilled water into the concentrated solution, centrifuging, collecting supernatant, adsorbing with macroporous resin column to remove flavonol glycoside and lactone, and collecting filtrate to obtain shikimic acid extractive solution, wherein the amount of the added distilled water is 3L per 1kg of folium Ginkgo put into the tank;
step 2, ultrafiltering shikimic acid extracting solution by adopting an ultrafiltration membrane of 200KDa, treating the shikimic acid extracting solution by using an LX-04 ion exchange resin column to obtain a pretreatment solution, and adding 1200ml of the pretreatment solution into an ethanol solution with the volume concentration of 95% to obtain a shikimic acid upper column solution; wherein the volume ratio of the pretreatment solution to the ethanol solution is 40: 60, adding a solvent to the mixture; detecting shikimic acid solution on the column by HPLC, wherein the concentration of shikimic acid is 9.1 mg/mL;
step 3, continuously feeding the shikimic acid solution into a chitosan adsorption column at the flow rate of 5ml/min, washing the chitosan adsorption column by using an ethanol solution with the volume concentration of 60% when the pH value of the effluent is detected to be 5.0, eluting the chitosan adsorption column adsorbed with shikimic acid by using an ethanol-containing sodium hydroxide solution with the pH value of 10 when the effluent is neutral, and collecting the eluate, namely shikimic acid eluate;
wherein, ethanol accounts for 60% of the volume of the sodium hydroxide solution containing ethanol; the chitosan adsorption column is prepared by wetting natural cationic polymer chitosan with deacetylation degree of 85% and granularity of 50 meshes with 60% ethanol water solution, and then loading on a column.
And 4, treating the shikimic acid eluate by using an LX-04 cation resin column to obtain a purified treatment solution, wherein the content of shikimic acid is 8.5mg/ml and the yield is 93% through HPLC detection. Finally, concentrating and drying the purified treatment solution to obtain shikimic acid with the purity of 82%.
In addition, after the adsorption columns in the above examples 1 to 3 are all eluted, 70% ethanol solution is used to wash the adsorption columns until the effluent liquid is neutral, thereby completing the regeneration of the adsorption columns, which can be reused.
Comparative example 1
Test without ethanol: 10g of chitosan with deacetylation degree of 88% 100 meshes is added into shikimic acid solution (containing shikimic acid 840mg) which is diluted by one time with pure water, and the chitosan is stirred by a glass rod at room temperature to form a paste, wherein the pH is neutral and cannot be further treated.
In order to further illustrate that chitosan as a natural cationic polymer can swell and form a colloidal compound in an acidic aqueous solution, which makes the operation of adsorbed acidic substances (organic acid or inorganic acid) difficult and makes the acidic substances difficult to separate, the invention mixes a shikimic acid solution with ethanol, compares the change of the volume of the chitosan when the ethanol concentration is different, finds that the chitosan hardly swells when the ethanol concentration of the shikimic acid solution is about 60 percent, and realizes the adsorption and separation of shikimic acid by the chitosan. The specific implementation is as follows:
firstly, a chitosan swelling experiment is as follows:
taking 6 10ml centrifuge tubes, accurately adding 0.5g (+ -0.0005 g) chitosan powder (100 meshes) with deacetylation degree of 88% into each tube, marking, carefully adding 10ml shikimic acid solution with ethanol volume content of 10%, 20%, 30%, 40%, 60% and 80% (after the shikimic acid solution is ultrafiltered, treating with cationic resin), adding 10ml 95% ethanol into the other tube as a control, standing for 1h, centrifuging at 4000r/min for 5min, taking out a test tube, and measuring the deposition height of chitosan at the bottom of the centrifuge tube, wherein the table 1 shows.
TABLE 1 influence of shikimic acid solutions containing ethanol at different concentrations on the swelling of chitosan
As can be seen from Table 1, the chitosan hardly swells when the volume content of ethanol in the shikimic acid solution is about 60%, and the technical scheme of the invention is fully proved to be feasible and has excellent effect.
Secondly, the adsorption rate of the chitosan to shikimic acid is implemented according to the following steps:
taking 3.0g (+ -0.0005 g) of chitosan with deacetylation degree of 88% of 60 meshes, adding 200ml of absolute ethyl alcohol and 100ml of shikimic acid solution subjected to ultrafiltration and cation resin column treatment, stirring for 4h by using a magnetic stirrer at room temperature, taking supernatant, and detecting the concentration of shikimic acid by using HPLC, wherein each gram of chitosan can absorb 0.16g of shikimic acid, namely the absorption rate is 16%.
The invention can also be used for recovering other organic acids in fermentation liquor and industrial waste liquid.
It should be noted that, when the present invention relates to numerical ranges, it should be understood that two endpoints of each numerical range and any value between the two endpoints can be selected, and since the steps and methods adopted are the same as those of the embodiments 1 to 3, the present invention describes the preferred embodiments in order to prevent the redundancy, but once the basic inventive concept is known, those skilled in the art can make other changes and modifications to the embodiments. Therefore, it is intended that the appended claims be interpreted as including preferred embodiments and all such alterations and modifications as fall within the scope of the invention.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include such modifications and variations.
Claims (4)
1. A method for adsorbing-separating shikimic acid by adopting chitosan is characterized by comprising the following steps:
step 1, preparing shikimic acid extracting solution from natural plants containing shikimic acid;
step 2, treating shikimic acid extracting solution by using a cation resin column to obtain a pretreatment solution; adding the pretreatment solution into an ethanol solution with the volume concentration of 95% to obtain a shikimic acid solution on a column; wherein the volume ratio of the pretreatment solution to the ethanol solution is 37-42%: 58 to 63 percent;
step 3, adding the shikimic acid solution into a chitosan adsorption column, washing the chitosan adsorption column by using an ethanol solution with the volume concentration of 40-80% when the pH value of the effluent is 4.5-5.5, eluting the chitosan adsorption column adsorbed with shikimic acid by using an ethanol-containing sodium hydroxide solution with the pH value of 8-12 when the effluent is washed to be neutral, and collecting the eluent, namely shikimic acid eluent; wherein ethanol in the ethanol-containing sodium hydroxide solution accounts for 40-80% of the total volume;
step 4, treating shikimic acid eluent by using a cation resin column to obtain purified treatment liquid, and concentrating and drying the purified treatment liquid to obtain shikimic acid;
the preparation method of the chitosan adsorption column comprises the following steps: wetting natural cationic polymer chitosan with deacetylation degree of 82-92% and granularity of 40-100 meshes with 40-95% ethanol solution, and loading into column to obtain chitosan adsorption column;
in step 2, before the shikimic acid extracting solution is treated by a cation resin column, an ultrafiltration membrane of 200KDa is adopted to carry out ultrafiltration on the shikimic acid extracting solution.
2. The method for adsorbing-separating shikimic acid using chitosan as claimed in claim 1, wherein the natural plant containing shikimic acid is star anise, pine needle or ginkgo leaf.
3. The method for adsorbing-separating shikimic acid with chitosan according to claim 2, wherein when preparing shikimic acid extract with aniseed, it comprises the following steps: distilling fructus Anisi Stellati to obtain oleum Foeniculi, and diluting the residual liquid with water to desired volume to obtain shikimic acid extractive solution; wherein the mass ratio of the star anise to the shikimic acid extracting solution obtained after constant volume is 100 g: 500 mL;
when the shikimic acid extracting solution is prepared by pine needles, the method comprises the following steps: reflux-extracting folium Pini with distilled water to obtain shikimic acid extractive solution; wherein the dosage ratio of the pine needles to the distilled water is 300 g: 7500 ml;
when the folium ginkgo is used for preparing shikimic acid extracting solution, the method comprises the following steps: extracting folium Ginkgo with ethanol under reflux, filtering, concentrating, adding distilled water into the concentrated solution, centrifuging, precipitating, collecting supernatant, and treating with macroporous resin to obtain shikimic acid extractive solution, wherein the dosage ratio of folium Ginkgo to distilled water is 1 kg: 3L.
4. The method for adsorbing-separating shikimic acid using chitosan according to claim 1 wherein in step 2 and step 4, said cation resin column is LX-04 ion exchange resin column.
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