CN113480585B - Preparation method of cornus officinalis new glycoside bulk drug - Google Patents
Preparation method of cornus officinalis new glycoside bulk drug Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The application provides a preparation method of a cornus officinalis neoglycoside bulk drug, which comprises the following steps: pulverizing Corni fructus fruit to obtain Corni fructus powder, adding extraction solvent into Corni fructus powder, reflux extracting to obtain extractive solution, filtering, and concentrating under reduced pressure to obtain concentrated solution; extracting the concentrated solution by using an organic solvent, and concentrating under reduced pressure to obtain an extracted water concentrated solution; sequentially subjecting the extracted water concentrate to macroporous adsorbent resin column chromatography and polyamide resin column chromatography, then performing gradient elution by using an eluting solvent, checking by silica gel thin layer chromatography or HPLC, collecting and combining the eluates containing the cornuside, and concentrating under reduced pressure to obtain the cornuside concentrate; and finally, recrystallizing the concentrated solution of the cornus officinalis neoside, and then drying to obtain the cornus officinalis neoside. The method has the advantages of simple and practical process flow, low toxicity and environmental protection, and high yield and high purity of the cornus officinalis neoglycoside is obtained due to the adoption of specific process conditions in each step.
Description
Technical Field
The application relates to the technical field of biological medicine, in particular to a preparation method of a cornus officinalis neoside bulk drug.
Background
At present, cornuside is an iridoid glycoside compound contained in dried mature fruits of Cornus officinalis (et zucc.) which is a cornaceae plant, and has the following structural formula:
【CAS】131189-57-6
[ molecular formula and molecular weight ] C 24 H 30 O 14 ；542.49
White powder is easily dissolved in methanol, ethanol, acetone, dimethyl sulfoxide, slightly dissolved in diethyl ether, hardly dissolved in ethyl acetate, and not dissolved in petroleum ether. Specific rotation: -91 (c=1.0 methanol); melting point: 108-109 ℃.
Cornus i de is iridoid glycoside compound, which is one of main components of traditional Chinese medicine cornus officinalis, and has pharmacological activities of reducing blood sugar, resisting arrhythmia, inhibiting cytotoxicity, etc.
CN104147079a discloses a method for extracting cornus officinalis iridoid glycoside by ultrasonic-microwave synergy, which comprises the following steps: soaking in boiled water, removing shell, drying, pulverizing to obtain coarse powder, dissolving the coarse powder with solvent, ultrasonic treating, vacuum filtering, and filtering to obtain cornus iridoid glycoside. The method has the defects that: 1) The pure cornus officinalis neoside is not separated, and the crude extract of cornus officinalis iridoid glycoside is obtained, wherein the crude extract also comprises some large iridoid components such as morroniside, loganin, swertiamarin and the like; 2) The preparation process has high requirements on equipment, large equipment investment and high cost; 3) Ultrasonic extraction has no industrial equipment and cannot be produced in a large scale and in an industrial manner.
Disclosure of Invention
The application aims to provide a preparation method of a cornus officinalis neoside bulk drug, which takes cornus officinalis fruits which are traditional Chinese medicines and are rich in cornus officinalis neoside as raw materials, and has the characteristics of low production cost, simple process flow, high product yield and purity and the like.
In order to solve the technical problems, the preparation method of the cornus officinalis new glycoside bulk drug provided by the application comprises the following steps:
step one: pulverizing Corni fructus fruit to obtain Corni fructus powder, adding extraction solvent into Corni fructus powder, reflux extracting to obtain extractive solution, filtering, and concentrating under reduced pressure to obtain concentrated solution;
step two: extracting the concentrated solution by using an organic solvent, and concentrating under reduced pressure to obtain an extracted water concentrated solution;
step three: sequentially subjecting the extracted water concentrate to macroporous adsorbent resin column chromatography and polyamide resin column chromatography, then performing gradient elution by using an eluting solvent, checking by silica gel thin layer chromatography or HPLC, collecting and combining the eluates containing the cornuside, and concentrating under reduced pressure to obtain the cornuside concentrate;
step four: recrystallizing the concentrated solution of cornus officinalis neoside with dichloromethane, chloroform, ethyl acetate, propyl acetate, acetone, n-butanol, ethanol, methanol or their mixture, and drying to obtain cornus officinalis neoside.
Further, the eluting solvent in step three is selected from water, methanol, ethanol, acetone or mixtures thereof.
In the second step, extracting the concentrated solution with an organic solvent for 3-5 times, combining the water phases, and concentrating under reduced pressure to obtain an extracted water concentrated solution; the organic solvent is petroleum ether, cyclohexane, dichloromethane, chloroform, ethyl acetate or propyl acetate; the dosage of the organic solvent is 1-3 times of the volume of the concentrated solution; the density of the water concentrate after extraction is 1.05-1.30.
In the first step, the adding amount of the extraction solvent is 8-15 times of the mass of the dogwood powder, the reflux extraction is carried out for 2-4 times, the extraction time is 2-3 hours each time, the extraction solutions are combined, filtered and concentrated under reduced pressure to obtain concentrated solution.
Further, the extraction solvent in step one is selected from water, methanol, ethanol or a mixture thereof; the extraction temperature is 70 ℃ to the boiling point temperature of the extraction solvent; the density of the obtained concentrated solution is 1.00-1.30.
Further, when the extraction solvent in the first step is a mixture of water and ethanol, the concentration of ethanol is 0-90%.
Preferably, in the first step, the extraction solvent is a mixture of water and ethanol, and the concentration range of the ethanol after mixing is 35-60%; preferably, the amount of the extraction solvent is 10 times of the mass of the dogwood powder.
Preferably, in the second step, the organic solvent is ethyl acetate.
Preferably, in step three, the macroporous adsorbent resin is preferably D101; the polyamide resin is preferably an alcohol-soluble polyamide resin;
preferably, in the third step, the eluting solvent is a mixture of water and ethanol, and the concentration range of the ethanol after mixing is 30-80%;
preferably, in the fourth step, the solvent for recrystallization is ethyl acetate or ethanol or a mixture of the two; the drying mode is reduced pressure drying, freeze drying or spray drying.
The production process of Cornus officinalis neoside uses dried mature fruits of Cornus officinalis (Cornus officinalis Sieb. Et Zucc.) as raw materials, and obtains Cornus officinalis neoside through the steps of solvent extraction, organic solvent extraction, macroporous adsorption resin column chromatography, polyamide resin column chromatography, recrystallization, drying and the like.
During extraction, the specific solvent disclosed by the application is selected from water, methanol, ethanol or a mixture thereof for extraction, so that the extraction has the characteristic of high extraction rate; in particular, a specific extraction solvent (i.e., a 35-65% ethanol-water mixture) is preferred for extraction, since ethanol and water are solvents with less toxicity that can be tolerated by the human body, a 35% ethanol-water mixture can give an extract rich in cornuside, whereas when the ethanol concentration increases to 65%, the probability of introducing small polar impurities increases greatly, so that in order to enrich a large amount of pure cornuside, both the operability, cost and efficiency of mass production are compromised, a 35-65% ethanol-water mixture is preferred as the extraction solvent.
In the extraction of the second step, the compatibility of the cornus officinalis neoglycoside and the organic solvent is fully considered. The extraction with the specific organic solvents before macroporous adsorption resin column chromatography is a key step superior to the traditional column chromatography, and the step can remove nonpolar and small polar impurities so as to simplify the subsequent column chromatography steps.
The method of combining macroporous adsorption resin column chromatography with polyamide resin column chromatography is favorable for gradual enrichment and purification of cornus officinalis neoside. And (3) carrying out macroporous adsorption resin column chromatography to obtain a crude sample containing the cornuside, and selecting a polyamide resin column to further enrich and purify the cornuside for further removing impurities. In consideration of the fact that the polarity of the cornus officinalis neoside is unified, the ethanol water solution is adopted as the gradient elution solvent, the production cost is reduced, and the environmental pollution is reduced.
For further purification and impurity removal after extraction, a recrystallization method is adopted, and the cornus officinalis neoglycoside is screened out through a preliminary experiment, is easy to recrystallize in ethyl acetate, ethanol or a mixture thereof, has a good crystal form, and is also preferred because more ethyl acetate and ethanol are applied in mass production and have low toxicity.
By adopting the technical scheme, the application has the following beneficial effects:
the method adopts the steps of solvent extraction, organic solvent extraction, chromatographic separation, recrystallization, drying and the like which are commonly used in industrialization, has simple and practical process flow, low toxicity and environmental protection, and can obtain the cornus officinalis neoside with high yield and high purity due to the adoption of specific process conditions in each step, thereby producing the effect more suitable for industrialized production, the yield of the cornus officinalis neoside is up to 0.11 percent, the purity is up to 99.0 percent, and the cornus officinalis neoside can be directly used as a raw material medicine.
Drawings
FIG. 1: high performance liquid chromatogram of cornus officinalis new glycoside raw material medicine.
Detailed Description
Embodiments of the present application will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only for illustrating the present application and should not be construed as limiting the scope of the present application. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The application is further illustrated with reference to specific embodiments.
Example 1
(1) Pulverizing Corni fructus fruit into powder, reflux-extracting with 50% ethanol for several times (for example 2-4 times, each for 2-4 hr), mixing extractive solutions, filtering, and concentrating under reduced pressure until no ethanol smell exists to obtain concentrated solution;
(2) Dispersing the concentrated solution in water, extracting with ethyl acetate for several times (for example, 2-4 times), mixing the water phases, and concentrating under reduced pressure to obtain water concentrated solution after extraction;
(3) Slowly loading the extracted water concentrate into a D101 macroporous adsorption resin column, loading the column by a wet method (the ratio of the sample amount to the column loading resin amount is 1:5), eluting with 35% ethanol for 6BV, and discarding; eluting with 55% ethanol for 5BV, collecting eluate in one third or one fourth as a fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure to obtain concentrated solution (relative density of 1.15); loading the concentrated solution into 60-100 mesh alcohol-soluble polyamide resin column, wet packing (sample amount and column packing resin amount ratio is 1:8), eluting with 30% ethanol for 4BV, and discarding; eluting with 50% ethanol for 5BV, collecting eluate with one half or one third as a fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure until no ethanol smell exists to obtain cornuside concentrate;
fig. 1 is a high performance liquid chromatogram of a cornus officinalis new glycoside bulk drug, and the determination method comprises the following steps: the detection system comprises: agi l ent Techno l ogies 1260I nfity II HPLC apparatus; chromatographic column: sonoma C18 (2) (250×4.6mm,5 μm); mobile phase: methanol/water (50:50-95:5, V/V,50 mi); sample injection amount: 20. Mu.L; flow rate: 1.0 mL/min; detection wavelength: 280nm; column temperature: 25 ℃.
(4) Dissolving the concentrated solution of cornus officinalis neoside with proper amount of ethyl acetate-ethanol (3:7), standing for crystallization, washing off impurities on the surface of the crystal with proper amount of ethanol, recrystallizing for several times (for example, 2-4 times) to obtain cornus officinalis neoside with purity of 99.5%, and drying under reduced pressure to obtain cornus officinalis neoside raw material medicine of about 0.55g with yield of 0.11%.
The preparation method of the cornus officinalis novel glycoside has been described by specific examples, and the person skilled in the art can properly change links of raw materials, process conditions and the like to achieve other corresponding purposes by referring to the content of the cornus officinalis novel glycoside, and all similar substitutions and modifications are obvious to those skilled in the art and are considered to be included in the scope of the present application.
Example two
(1) Pulverizing Corni fructus fruit into powder, reflux-extracting with 40% ethanol for several times (for example 2-4 times, each for 2-4 hr), mixing extractive solutions, filtering, and concentrating under reduced pressure until no ethanol smell exists to obtain concentrated solution;
(2) Dispersing the concentrated solution in water, extracting with ethyl acetate for several times (for example, 2-4 times), mixing the water phases, and concentrating under reduced pressure to obtain water concentrated solution after extraction;
(3) Slowly loading the extracted water concentrate into an AB-8 macroporous adsorption resin column, loading the column by a wet method (the ratio of the sample amount to the column loading resin amount is 1:5), eluting with 35% ethanol for 6BV, and discarding; eluting with 55% ethanol for 5BV, collecting eluate in one third or one fourth as a fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure to obtain concentrated solution (density 1.10); loading the concentrated solution into 60-100 mesh alcohol-soluble polyamide resin column, wet packing (sample amount and column packing resin amount ratio is 1:8), eluting with 30% ethanol for 4BV, and discarding; eluting with 50% ethanol for 5BV, collecting eluate with one half or one third as a fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure until no ethanol smell exists to obtain cornuside concentrate;
(4) Dissolving the concentrated solution of cornus officinalis neoside with appropriate amount of ethyl acetate-ethanol (4:6), standing for crystallization, washing off impurities on the surface of the crystal with appropriate amount of ethanol, recrystallizing for several times (for example, 2-4 times) to obtain cornus officinalis neoside with purity of 99.2%, and lyophilizing to obtain cornus officinalis neoside raw material medicine about 0.50g with yield of 0.10%.
Example III
(1) Pulverizing Corni fructus fruit into coarse powder, reflux-extracting with 60% ethanol for several times (for example, 2-4 times for 3 hr each time), mixing extractive solutions, filtering, and concentrating under reduced pressure until no ethanol smell exists to obtain concentrated solution;
(2) Dispersing the concentrated solution in water, extracting with ethyl acetate for several times (for example, 2-4 times), mixing the water phases, and concentrating under reduced pressure to obtain water concentrated solution after extraction;
(3) Slowly loading the extracted water concentrate into an HP-20 macroporous adsorption resin column, loading the column by a wet method (the ratio of the sample amount to the column loading resin amount is 1:5), eluting with 35% ethanol for 6BV, and discarding; eluting with 55% ethanol for 5BV, collecting eluate in one third or one fourth as a fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure to obtain concentrated solution (relative density 1.13); loading the concentrated solution into 60-100 mesh alcohol-soluble polyamide resin column, wet packing (sample amount and column packing resin amount ratio is 1:8), eluting with 30% ethanol for 4BV, and discarding; eluting with 50% ethanol for 5BV, collecting eluate with one half or one third as a fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure until no ethanol smell exists to obtain cornuside concentrate;
(4) Dissolving the concentrated solution of cornus officinalis neoside with proper amount of ethyl acetate-ethanol (2:8), standing for crystallization, washing off impurities on the surface of the crystal with proper amount of ethanol, recrystallizing for several times (for example, 2-4 times) to obtain cornus officinalis neoside with purity of 99.0%, and spray drying to obtain cornus officinalis neoside raw material medicine with yield of 0.09%.
In addition, in order to further compare the effect of selecting a specific preparation method according to the present application, the following comparative examples are specially set to compare with the first embodiment of the present application, and specific results are shown in table 1 below, because the yield of cornus officinalis neoside in the first embodiment is as high as 0.11%, and the purity is as high as 99.5%. Wherein, the dosage of the dogwood powder is the same in all the examples and the comparative examples.
Comparative example 1: the procedure of example I was followed except that no organic solvent extraction was used before the macroporous adsorbent resin column. The comparative example shows that the purity of the cornus officinalis neoside finally obtained by extraction without adopting an organic solvent before the macroporous adsorption resin column is only 80.3%, and the effect is inferior to that of the cornus officinalis neoside bulk drug prepared by the application.
Comparative example 2: the first embodiment is the same as the first embodiment except that the macroporous adsorbent resin column is not used for chromatography; the comparative example shows that the purity of the cornuside finally obtained by column chromatography without macroporous adsorption resin is only 82.7%, and the effect is inferior to that of the cornuside bulk drug prepared by the application.
Comparative example 3: the procedure of example I was followed except that the column chromatography was not carried out; the comparative example shows that the purity of the cornuside finally obtained by the column chromatography without adopting the polyamide resin is only 84.5%, and the effect is inferior to the purity of the cornuside raw material medicine prepared by the application.
Comparative example 4: the procedure of example one was followed except that the macroporous adsorbent resin column and the polyamide resin column were eluted without using ethanol water; the comparative example shows that the purity of the finally obtained cornus officinalis neoside is only 89.5% without adopting ethanol water to elute the macroporous adsorption resin column and the polyamide resin column, and the effect is inferior to that of the cornus officinalis neoside bulk drug prepared by the application.
Comparative example 5: the procedure of example I was followed except that recrystallization was not employed; the comparative example shows that the purity of the cornus officinalis neoside finally obtained without recrystallization is only 91.8%, and the effect is inferior to the purity of the cornus officinalis neoside bulk drug prepared by the application.
Comparative example 6: the same procedure as in example one except that the extraction solvent in step one was water; the comparative example shows that the yield of the cornus officinalis neoglycoside finally obtained by extraction without adopting the preferred extraction solvent is only 0.07%, and the effect is inferior to that of the application;
comparative example 7: the procedure of example I was followed except that the extraction solvent in step I was 20% ethanol; this comparative example shows that the yield of cornus officinalis neoglycoside finally obtained by solvent extraction with a ratio lower than that of the preferred extraction solvent is only 0.06%, and the effect is inferior to that of the present application.
Comparative example 8: the procedure of example II was followed except that the organic solvent used in the second step was n-butanol; the comparative example shows that the yield of the cornus officinalis neoglycoside finally obtained without ethyl acetate extraction is only 0.05%, and the effect is inferior to that of the application.
Comparative example 9: the procedure of example three was followed except that the organic solvent for extraction in step three was methylene chloride; the comparative example shows that the yield of the cornus officinalis neoglycoside finally obtained without ethyl acetate extraction is only 0.06%, and the effect is inferior to that of the application.
Comparative example 10: the procedure of example I was followed except that the macroporous adsorbent resin column was DA 201; the comparative example shows that the yield of cornus officinalis neoside finally obtained by column chromatography without adopting the preferred macroporous adsorption resin is only 0.04%, the purity is only 95.0%, and the effect is worse than that of the application.
Table 1 comparative experiment results table
As can be seen from the table 1, the application has the advantages of simple process flow, less sample loss, less environmental pollution, solvent and time saving, high yield and purity of the cornus officinalis neoside crude drug, and suitability for industrial production; in addition, compared with comparative examples 1 to 10, the specific selection of the separation steps of solvent extraction-organic solvent extraction-macroporous adsorbent resin-polyamide resin-recrystallization, and the specific selection of the process conditions in the preparation process, etc., have important effects on the yield and purity of the final product. Wherein the effect of the first embodiment is optimal.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present application, and not for limiting the same; although the application has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the application.
Claims (1)
1. The preparation method of the cornus officinalis new glycoside bulk drug is characterized by comprising the following steps:
step one: pulverizing Corni fructus fruit to obtain Corni fructus powder, adding extraction solvent into Corni fructus powder, reflux-extracting with the amount of 8-15 times of the mass of Corni fructus powder for 2-4 times, each time for 2-3 hr, mixing the extractive solutions, filtering, and concentrating under reduced pressure to obtain concentrated solution;
the extraction solvent is a mixture of water and ethanol, and the concentration range of the ethanol after mixing is 35-60%;
the extraction temperature is 70 ℃ to the boiling point temperature of the extraction solvent; the density of the prepared concentrated solution is 1.00-1.30;
step two: extracting the concentrated solution with organic solvent for 3-5 times, mixing the water phases, and concentrating under reduced pressure to obtain water concentrated solution after extraction; the organic solvent is ethyl acetate; the dosage of the organic solvent is 1-3 times of the volume of the concentrated solution; the density of the water concentrate after extraction is 1.05-1.30;
step three: sequentially subjecting the extracted water concentrate to macroporous adsorbent resin column chromatography and polyamide resin column chromatography, then performing gradient elution by using an eluting solvent, checking by silica gel thin layer chromatography or HPLC, collecting and combining the eluates containing the cornuside, and concentrating under reduced pressure to obtain the cornuside concentrate; wherein the macroporous adsorption resin is D101; the polyamide resin is alcohol-soluble polyamide resin; the eluting solvent is a mixture of water and ethanol, and the concentration range of the ethanol after mixing is 30-80%;
step four: recrystallizing the concentrated solution of cornuside with ethyl acetate and ethanol as solvent, and drying to obtain cornuside.
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