CN113512084B - Method for extracting stigmasterol from coix seed stems and leaves by combining ultrasonic countercurrent with biological enzyme - Google Patents
Method for extracting stigmasterol from coix seed stems and leaves by combining ultrasonic countercurrent with biological enzyme Download PDFInfo
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- CN113512084B CN113512084B CN202110327520.3A CN202110327520A CN113512084B CN 113512084 B CN113512084 B CN 113512084B CN 202110327520 A CN202110327520 A CN 202110327520A CN 113512084 B CN113512084 B CN 113512084B
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Abstract
The invention discloses a method for extracting stigmasterol from coix stems and leaves by combining ultrasonic countercurrent with biological enzyme, which comprises the steps of adding coix seed powder into a solution containing quicklime and sodium thiosulfate for soaking, filtering, putting coix seed powder and water into an ultrasonic countercurrent extraction tank, adding biological enzyme, carrying out ultrasonic countercurrent extraction at different temperatures, and filtering to obtain leaching liquor; concentrating the leaching solution under reduced pressure, dissolving the extract in an organic solvent containing sodium hydroxide and sodium tripolyphosphate, and performing saponification reaction; extracting the saponified product with PBS buffer solution and acetonitrile, discarding the water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract; and filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering and crystallizing the obtained stigmasterol product to obtain the stigmasterol product. The method has the advantages of high extraction rate, high extraction efficiency, simpler process, low production cost, product purity reaching more than 99 percent, and the like.
Description
Technical Field
The invention relates to the technical field of extraction of plant active ingredients, in particular to a method for extracting stigmasterol from coix stems and leaves by combining ultrasonic countercurrent with biological enzyme.
Background
Coix lacryma-jobi L.is of Gramineae, has sweet and light taste and slightly cold nature, has effects of invigorating spleen, nourishing lung, clearing heat, and promoting diuresis, and has the reputation of "nourishing and health promoting king". At present, the research on chemical components of coix seeds is less, more coix seeds are concentrated, the literature report on the pharmacological activity research is not much, the basis of bioactive substances is not clear, and the clinical application of coix seeds is limited. Researches prove that the coix leaves also contain chemical components such as steroids, polysaccharide, flavone, organic acid, sphingoid, triterpene and the like, so that the research on how to extract stigmasterol from the coix leaves can change waste into valuable, and the value of the whole coix plants is improved.
Stigmasterol (stigmaster 01), C29H450. Molecular weight 412, also known as stigmasterol-5, 22-dien-3B-ol or 24R-ethyl cholest-5, 22-dien-3B-ol, is a phytosterol, which is widely found in a variety of plants. Stigmasterol has remarkable antioxidant, antitumor, cardiovascular disease resisting and other pharmacological activities, is also the starting material for synthesizing steroid medicines, and has application in the industries of medicine, food, chemical industry and the like. In recent years, with the discovery of new steroid drugs, the development of production, the expansion of production scale, and the increase of raw material requirements; on the other hand, due to unreasonable extraction, resources are in shortage, the content of saponin in plants is reduced, so that contradiction between supply and demand of international markets occurs, and how to obtain more stigmasterols with higher purity is an important direction of stigmasterol research.
The applicant provides a method for extracting stigmasterol from coix seed stems, which comprises the steps of enzymolysis, ultrasonic extraction, saponification, urea column chromatography, crystallization and the like. However, in the test process, the applicant finds that the method for extracting stigmasterol from coix leaves has the defects of more impurities, lower product purity, lower extraction rate, low production efficiency and the like. Therefore, the invention improves the original technology better.
Disclosure of Invention
The invention aims to provide a method for extracting stigmasterol from coix stems and leaves by combining ultrasonic countercurrent with biological enzyme. The method for extracting stigmasterol by combining ultrasonic countercurrent with biological enzyme has the advantages of high extraction rate, high product purity, high extraction efficiency, simpler process, low production cost and the like.
In order to achieve the above object, the present invention adopts the following technical scheme:
a method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme comprises the following steps:
(1) Cleaning Coicis semen stem or leaf, crushing to 40-100 mesh, sieving to obtain Coicis semen powder, adding Coicis semen powder into solution containing quick lime and sodium thiosulfate, soaking for 30-60min, filtering, adding Coicis semen powder and water into ultrasonic countercurrent extraction tank, adding biological enzyme, ultrasonic countercurrent extracting at different temperatures, and filtering to obtain extractive solution; the biological enzyme consists of cellulase, pectase and xylanase;
(2) Concentrating the leaching solution under reduced pressure to obtain extract, dissolving the extract in organic solvent containing sodium hydroxide and sodium tripolyphosphate, heating to 50-70deg.C, and saponifying for 60-90min to obtain saponified product;
(3) Extracting the saponified product with PBS buffer solution and acetonitrile, discarding the water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract;
(4) Filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering and crystallizing the obtained stigmasterol product to obtain the stigmasterol product.
Further, the mass ratio of the quicklime to the sodium thiosulfate is 2-4:1; the addition amount is 3-5% of the mass concentration of the prepared soaking solution.
Further, the ultrasonic countercurrent extraction is carried out for 1-2 hours at the temperature of 50-60 ℃, the temperature is raised to 65-70 ℃ for 1.0-1.5 hours, and finally the temperature is raised to 75-80 ℃ for 0.5-1.0 hour.
Further, the addition amount of the biological enzyme is 0.5-1.5% of the weight of the coix seed powder.
Further, the mass ratio of the cellulase to the pectase to the xylanase in the biological enzyme is 3-5:1-3:0.5-1.
Further, the addition amounts of the sodium hydroxide and the sodium tripolyphosphate in the step (2) are respectively 10-15% and 3-5% of the mass of the organic solvent.
Further, the organic solvent consists of tetrahydrofuran and ethanol in a volume ratio of 1:3-5.
Further, the volume ratio of the PBS buffer solution to the acetonitrile is 1:5-10.
Further, the pH of the PBS buffer was 5.8.
Further, the eluent consists of phosphoric acid solution and ethyl acetate in a volume ratio of 1:10-15.
Compared with the prior art, the invention has the advantages that:
1. the invention takes coix stems or leaves as raw materials, firstly, quick lime and sodium thiosulfate are used for soaking, an ultrasonic countercurrent extraction tank is added, biological enzyme is combined for extracting extractum, and then, the stigmasterol is extracted through steps of saponification reaction, column chromatography and the like.
2. According to the method, before ultrasonic countercurrent, the coix seed powder is added into the quicklime and sodium thiosulfate solution for soaking, so that the breakage of the cell walls of coix seed stems or leaves can be promoted, stigmasterol can be extracted more easily, and the extraction rate is improved.
3. The method comprises the steps of carrying out saponification reaction in sodium hydroxide and sodium tripolyphosphate solution, extracting by using PBS buffer solution and acetonitrile, and adding sodium tripolyphosphate to promote the saponification reaction and further play a role in purifying adsorbed impurities; extraction with PBS buffer can neutralize the alkali in the saponification reaction and moreover, stigmasterol is more easily separated.
4. The invention adopts polyacrylamide gel column chromatography, so that the stigmasterol is easier to separate, the effect of adsorbing impurities and purifying can be achieved, and the purity of the stigmasterol is improved.
Detailed Description
The present invention will be described in further detail with reference to the following embodiments. It should be emphasized that the following description is merely exemplary in nature and is in no way intended to limit the scope of the invention or its applications.
Example 1
A method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme comprises the following steps:
(1) Cleaning stems or leaves of coix seeds, crushing to 60 meshes, sieving to obtain coix seed powder, adding the coix seed powder into a solution containing quicklime and sodium thiosulfate in a mass ratio of 3:1 (the mass concentration of the solution is 4%) for soaking for 60min, filtering, putting the coix seed powder and water into an ultrasonic countercurrent extraction tank, and adding cellulase, pectase and xylanase biological enzyme in a mass ratio of 4:1:1, wherein the adding amount of the biological enzyme is 1.2% of the weight of the coix seed powder. Extracting with ultrasonic countercurrent at 60deg.C for 2 hr, heating to 70deg.C for 1.0 hr, heating to 75deg.C for 1.0 hr, and filtering to obtain extractive solution.
(2) Concentrating the leaching solution under reduced pressure at-0.06 MPa and 80 ℃ to obtain an extract, dissolving the extract in an organic solvent added with sodium hydroxide and sodium tripolyphosphate, wherein the addition amount of the sodium hydroxide and the sodium tripolyphosphate is 13% and 3% of the mass of the organic solvent respectively, the organic solvent consists of tetrahydrofuran and ethanol in a volume ratio of 1:3, and heating to 60 ℃ for saponification reaction for 80min to obtain a saponified product;
(3) Extracting the saponified product with PBS buffer solution (pH 5.8) and acetonitrile at volume ratio of 1:8, discarding water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract;
(4) Filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent composed of phosphoric acid solution and ethyl acetate in a volume ratio of 1:12, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering the obtained stigmasterol product, and crystallizing to obtain the stigmasterol product.
The detection shows that the yield of stigmasterol in the example is 93.18%, and the purity of stigmasterol is 99.48%.
Example 2
A method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme comprises the following steps:
(1) Cleaning Coicis semen stem or leaf, crushing to 40 mesh, sieving to obtain Coicis semen powder, adding Coicis semen powder into solution containing quicklime and sodium thiosulfate (the mass concentration of the solution is 4.5%) at a mass ratio of 2:1, soaking for 50min, filtering, adding Coicis semen powder and water into ultrasonic countercurrent extraction tank, adding cellulase, pectase and xylanase biological enzyme at a mass ratio of 5:1.5:0.5, and the amount of biological enzyme is 1.4% of the weight of Coicis semen powder. Extracting at 55deg.C under ultrasonic countercurrent for 1.5 hr, heating to 65deg.C for 1.5 hr, heating to 75deg.C for 0.5 hr, and filtering to obtain extractive solution.
(2) Concentrating the leaching solution under reduced pressure at the pressure of-0.07 MPa and the temperature of 75 ℃ to obtain an extract, dissolving the extract in an organic solvent added with sodium hydroxide and sodium tripolyphosphate, wherein the addition of the sodium hydroxide and the sodium tripolyphosphate is 15% and 3% of the mass of the organic solvent respectively, the organic solvent consists of tetrahydrofuran and ethanol in a volume ratio of 1:4, and heating to 70 ℃ for saponification reaction for 90min to obtain a saponified product;
(3) Extracting the saponified product with PBS buffer solution (pH of 5.8) and acetonitrile at volume ratio of 1:5, discarding water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract;
(4) Filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent composed of phosphoric acid solution and ethyl acetate in a volume ratio of 1:15, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering the obtained stigmasterol product, and crystallizing to obtain the stigmasterol product.
The detection shows that the yield of stigmasterol in this example is 90.47%, and the purity of stigmasterol is 99.32%.
Example 3
A method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme comprises the following steps:
(1) Cleaning stems or leaves of coix seeds, crushing to 100 meshes, sieving to obtain coix seed powder, adding the coix seed powder into a solution containing quicklime and sodium thiosulfate in a mass ratio of 3:1 (the mass concentration of the solution is 5%) for soaking for 40min, filtering, putting the coix seed powder and water into an ultrasonic countercurrent extraction tank, and adding cellulase, pectase and xylanase biological enzyme in a mass ratio of 5:2:1, wherein the adding amount of the biological enzyme is 1.2% of the weight of the coix seed powder. Extracting at 60deg.C under ultrasonic countercurrent for 1.5 hr, heating to 70deg.C for 1.5 hr, heating to 75deg.C for 1.0 hr, and filtering to obtain extractive solution.
(2) Concentrating the leaching solution under reduced pressure at-0.06 MPa and 80 ℃ to obtain an extract, dissolving the extract in an organic solvent added with sodium hydroxide and sodium tripolyphosphate, wherein the addition amount of the sodium hydroxide and the sodium tripolyphosphate is respectively 10% and 5% of the mass of the organic solvent, the organic solvent consists of tetrahydrofuran and ethanol in a volume ratio of 1:4, and heating to 70 ℃ for saponification reaction for 70min to obtain a saponified product;
(3) Extracting the saponified product with PBS buffer solution (pH of 5.8) and acetonitrile at volume ratio of 1:10, discarding water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract;
(4) Filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent composed of phosphoric acid solution and ethyl acetate in a volume ratio of 1:10, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering the obtained stigmasterol product, and crystallizing to obtain the stigmasterol product.
The detection shows that the yield of stigmasterol in this example is 89.65%, and the purity of stigmasterol is 99.38%.
Example 4
A method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme comprises the following steps:
(1) Cleaning stems or leaves of Coicis semen, crushing to 60 mesh, sieving to obtain Coicis semen powder, adding Coicis semen powder into solution containing quicklime and sodium thiosulfate at a mass ratio of 4:1 (the mass concentration of the solution is 4.0%) for soaking for 45min, filtering, adding Coicis semen powder and water into an ultrasonic countercurrent extraction tank, adding cellulase, pectase and xylanase biological enzyme at a mass ratio of 4:1:1, and adding biological enzyme at an amount of 0.9% of the weight of Coicis semen powder. Extracting with ultrasonic countercurrent at 60deg.C for 2 hr, heating to 70deg.C for 1.0 hr, heating to 75deg.C for 1.0 hr, and filtering to obtain extractive solution.
(2) Concentrating the leaching solution under reduced pressure at the pressure of-0.07 MPa and the temperature of 75 ℃ to obtain an extract, dissolving the extract in an organic solvent added with sodium hydroxide and sodium tripolyphosphate, wherein the addition of the sodium hydroxide and the sodium tripolyphosphate is respectively 12% and 3% of the mass of the organic solvent, the organic solvent consists of tetrahydrofuran and ethanol in a volume ratio of 1:4, and heating to 70 ℃ for saponification reaction for 60min to obtain a saponified product;
(3) Extracting the saponified product with PBS buffer solution (pH of 5.8) and acetonitrile at volume ratio of 1:10, discarding water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract;
(4) Filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent composed of phosphoric acid solution and ethyl acetate in a volume ratio of 1:12, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering the obtained stigmasterol product, and crystallizing to obtain the stigmasterol product.
The detection shows that the yield of stigmasterol in this example is 89.65%, and the purity of stigmasterol is 99.19%.
Example 5
A method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme comprises the following steps:
(1) Cleaning Coicis semen stem or leaf, crushing to 80 mesh, sieving to obtain Coicis semen powder, adding Coicis semen powder into solution containing quicklime and sodium thiosulfate (3.6% of the mass concentration of the solution) at a mass ratio of 2:1, soaking for 40min, filtering, adding Coicis semen powder and water into ultrasonic countercurrent extraction tank, adding cellulase, pectase and xylanase biological enzyme at a mass ratio of 3:1:1, and adding biological enzyme at an amount of 1.5% of the weight of Coicis semen powder. Extracting with ultrasonic countercurrent at 55deg.C for 2 hr, heating to 70deg.C for 1.5 hr, heating to 75deg.C for 0.5 hr, and filtering to obtain extractive solution.
(2) Concentrating the leaching solution under reduced pressure at-0.06 MPa and 80 ℃ to obtain an extract, dissolving the extract in an organic solvent added with sodium hydroxide and sodium tripolyphosphate, wherein the addition amount of the sodium hydroxide and the sodium tripolyphosphate is 13% and 4% of the mass of the organic solvent respectively, the organic solvent consists of tetrahydrofuran and ethanol in a volume ratio of 1:4, and heating to 70 ℃ for saponification reaction for 60min to obtain a saponified product;
(3) Extracting the saponified product with PBS buffer solution (pH of 5.8) and acetonitrile at volume ratio of 1:7, discarding water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract;
(4) Filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent composed of phosphoric acid solution and ethyl acetate in a volume ratio of 1:15, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering the obtained stigmasterol product, and crystallizing to obtain the stigmasterol product.
The detection shows that the yield of stigmasterol in this example is 91.57%, and the purity of stigmasterol is 99.27%.
The foregoing is a further detailed description of the invention in connection with specific/preferred embodiments, and is not intended to limit the practice of the invention to such description. It will be apparent to those skilled in the art that several alternatives or modifications can be made to the described embodiments without departing from the spirit of the invention, and these alternatives or modifications should be considered to be within the scope of the invention.
Claims (4)
1. A method for extracting stigmasterol from coix seed leaves by combining ultrasonic countercurrent with biological enzyme is characterized in that: the method comprises the following steps:
(1) Cleaning Coicis semen stem or leaf, crushing to 40-100 mesh, sieving to obtain Coicis semen powder, adding Coicis semen powder into solution containing quick lime and sodium thiosulfate, soaking for 30-60min, filtering, adding Coicis semen powder and water into ultrasonic countercurrent extraction tank, adding biological enzyme, ultrasonic countercurrent extracting at different temperatures, and filtering to obtain extractive solution; the biological enzyme consists of cellulase, pectase and xylanase;
(2) Concentrating the leaching solution under reduced pressure to obtain extract, dissolving the extract in organic solvent containing sodium hydroxide and sodium tripolyphosphate, heating to 50-70deg.C, and saponifying for 60-90min to obtain saponified product;
(3) Extracting the saponified product with PBS buffer solution and acetonitrile, discarding the water phase, concentrating under reduced pressure, and recovering acetonitrile to obtain crude extract;
(4) Filling the crude extract into polyacrylamide gel column chromatography, eluting with an eluent, collecting stigmasterol eluent, concentrating and recovering the eluent, filtering and crystallizing the obtained stigmasterol product to obtain a stigmasterol product;
the mass ratio of the quicklime to the sodium thiosulfate is 2-4:1; the addition amount is 3-5% of the mass concentration of the prepared soaking solution;
the ultrasonic countercurrent extraction is carried out for 1-2 hours at 50-60 ℃, the temperature is raised to 65-70 ℃ for 1.0-1.5 hours, and finally the temperature is raised to 75-80 ℃ for 0.5-1.0 hour;
the addition amount of the biological enzyme is 0.5-1.5% of the weight of the coix seed powder;
the mass ratio of the cellulase to the pectase to the xylanase in the biological enzyme is 3-5:1-3:0.5-1;
the addition amounts of the sodium hydroxide and the sodium tripolyphosphate in the step (2) are respectively 10-15% and 3-5% of the mass of the organic solvent;
the organic solvent consists of tetrahydrofuran and ethanol in the volume ratio of 1:3-5.
2. The method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme according to claim 1, wherein: the volume ratio of the PBS buffer solution to the acetonitrile is 1:5-10.
3. The method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme according to claim 1, wherein: the pH of the PBS buffer was 5.8.
4. The method for extracting stigmasterol from coix seed leaves by ultrasonic countercurrent combination with biological enzyme according to claim 1, wherein: the eluent consists of phosphoric acid solution and ethyl acetate in the volume ratio of 1:10-15.
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