CN113480585A - Preparation method of cornuside raw material medicine - Google Patents
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Abstract
The invention provides a preparation method of cornuside raw material medicine, which comprises the following steps: crushing dogwood fruits to obtain dogwood powder, adding an extraction solvent into the dogwood powder, performing reflux extraction to obtain an extracting solution, filtering, and performing reduced pressure concentration to obtain a concentrated solution; extracting the concentrated solution by using an organic solvent, and concentrating under reduced pressure to obtain an extracted water concentrated solution; subjecting the extracted water concentrate to macroporous adsorbent resin column chromatography and polyamide resin column chromatography in sequence, performing gradient elution with eluting solvent, performing silica gel thin layer chromatography or HPLC, collecting eluate containing cornuside, and concentrating under reduced pressure to obtain cornuside concentrate; and finally, recrystallizing the cornuside concentrated solution, and then drying to obtain the cornuside. The invention has simple and practical process flow, low toxicity and environmental protection, and obtains the cornuside with high yield and high purity because the specific process conditions are adopted in each step.
Description
Technical Field
The invention relates to the technical field of biological medicines, in particular to a preparation method of a cornuside raw material medicine.
Background
At present, cornuside is an iridoid glycoside compound contained in dried mature fruits of Cornus officinalis (Cornus officinalis sieb. et Zucc.) belonging to the family cornaceae, and its structural formula is as follows:
【CAS】131189-57-6
[ molecular formula and molecular weight ] C24H30O14；542.49
[ physicochemical properties ] white powder, easily soluble in methanol, ethanol, acetone, dimethyl sulfoxide, slightly soluble in ether, insoluble in ethyl acetate, insoluble in petroleum ether. Specific optical rotation: -91(c ═ 1.0 methanol); melting point: 108 ℃ and 109 ℃.
Cornus officinalis new glycoside (cornus i de) is iridoid glycoside compound, is one of main components of traditional Chinese medicine cornus officinalis, and has pharmacological activities of reducing blood sugar, resisting arrhythmia, inhibiting cytotoxicity and the like.
CN104147079A discloses a method for extracting cornus officinalis iridoid glycoside by ultrasonic-microwave synergy, which comprises the following steps: soaking in boiled water, removing fruit shell, drying, pulverizing to obtain coarse powder, dissolving the coarse powder in solvent, ultrasonic treating, vacuum filtering, and coating with membrane. The disadvantages of this method are: 1) pure cornuside is not separated, and crude extract of cornuside is obtained, wherein the crude extract also comprises some iridoid components with large amount such as morroniside, loganin, swertiamarin and the like; 2) the preparation process has high requirements on equipment, large equipment investment and high cost; 3) the ultrasonic extraction has no industrial equipment, and large-scale and industrial production cannot be realized.
Disclosure of Invention
The invention aims to provide a preparation method of a cornuside raw material medicine, which takes fruits of traditional Chinese medicine cornus officinalis rich in cornuside as raw materials, and has the characteristics of low production cost, simple process flow, high product yield and high purity and the like.
In order to solve the technical problems, the preparation method of the cornuside raw material medicine provided by the invention comprises the following steps:
the method comprises the following steps: crushing dogwood fruits to obtain dogwood powder, adding an extraction solvent into the dogwood powder, performing reflux extraction to obtain an extracting solution, filtering, and performing reduced pressure concentration to obtain a 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: subjecting the extracted water concentrate to macroporous adsorbent resin column chromatography and polyamide resin column chromatography in sequence, performing gradient elution with eluting solvent, performing silica gel thin layer chromatography or HPLC, collecting eluate containing cornuside, and concentrating under reduced pressure to obtain cornuside concentrate;
step four: recrystallizing with dichloromethane, chloroform, ethyl acetate, propyl acetate, acetone, n-butanol, ethanol, methanol or their mixture, and drying to obtain cornuside.
Further, the eluting solvent in step three is selected from water, methanol, ethanol, acetone or their mixture.
Further, in the second step, extracting the concentrated solution with organic solvent for 3-5 times, combining water phases, and concentrating under reduced pressure to obtain extracted water concentrated solution; the organic solvent is petroleum ether, cyclohexane, dichloromethane, trichloromethane, 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 concentrated solution after extraction is 1.05-1.30.
Further, in the first step, the addition amount of the extraction solvent is 8-15 times of the mass of the dogwood powder, reflux extraction is carried out for 2-4 times, each extraction time is 2-3 hours, the extracting solutions are combined, filtered and concentrated under reduced pressure to obtain a concentrated solution.
Further, the extraction solvent in step one is selected from water, methanol, ethanol or their mixture; the extraction temperature is 70 ℃ to the boiling temperature of the extraction solvent; the density of the prepared 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 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 step two, the organic solvent is ethyl acetate.
Preferably, in the third step, the macroporous adsorption resin is preferably D101; the polyamide resin is preferably an alcohol-soluble polyamide resin;
preferably, in the third step, the elution solvent is a mixture of water and ethanol, and the concentration 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 ethyl acetate and the ethanol; the drying method is vacuum drying, freeze drying or spray drying.
The production process of Cornus officinalis neo-glycoside uses dried mature fruit of Cornus officinalis (Cornus officinalis Sieb. Et Zucc.) as raw material, and adopts the steps of solvent extraction, organic solvent extraction, macroporous adsorption resin column chromatography, polyamide resin column chromatography, recrystallization and drying so as to obtain the Cornus officinalis neo-glycoside.
During extraction, the specific solvent is selected from water, methanol, ethanol or a mixture thereof for extraction, so that the extraction rate is high; in particular, a specific extraction solvent (i.e. a mixture of 35-65% ethanol and water) is preferred for extraction, and since ethanol and water are both solvents with low toxicity which can be tolerated by the human body, the 35% ethanol-water mixture can obtain an extract rich in cornuside, and when the ethanol concentration is increased to 65%, the probability of introducing small polar impurities is greatly increased, so that the 35-65% ethanol-water mixture is preferred as the extraction solvent in order to enrich the large amount of pure cornuside while considering the operability, cost and benefit of mass production.
And in the extraction of the second step, the compatibility of the cornuside and the organic solvent is fully considered. The specific organic solvent is used for extraction before macroporous adsorption resin column chromatography, which is a key link superior to the traditional column chromatography, and the step can remove non-polar and low-polar impurities so as to simplify the subsequent column chromatography step.
The method of combining macroporous adsorption resin column chromatography with polyamide resin column chromatography is favorable for gradual enrichment and purification of cornuside. And after macroporous adsorption resin column chromatography, preliminarily obtaining a crude sample containing cornuside, and selecting a polyamide resin column for further enriching and purifying the cornuside in order to further remove impurities. Considering that the polarity of the cornuside is unified, the ethanol water solution is used as a gradient elution solvent, and the step reduces the production cost and the environmental pollution.
In order to further purify and remove impurities after extraction, a recrystallization method is adopted, and the dogwood neoside screened by earlier experiments is easy to recrystallize and has better crystal form in ethyl acetate, ethanol or a mixture thereof, and the ethyl acetate and the ethanol are preferably selected in consideration of more application and lower toxicity in large-scale production.
By adopting the technical scheme, the invention 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 obtains the new dogwood glycoside with high yield and high purity due to the adoption of specific process conditions in each step, thereby generating the effect more suitable for industrialized production, the yield of the new dogwood glycoside reaches 0.11 percent, the purity reaches 99.0 percent, and the new dogwood glycoside can be directly used as a raw material medicine.
Drawings
FIG. 1: high performance liquid chromatogram of cornuside raw material medicine.
Detailed Description
Embodiments of the present invention 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 illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The present invention will be further explained with reference to specific embodiments.
Example one
(1) Pulverizing Corni fructus into powder, reflux-extracting with 50% ethanol for several times (such as 2-4 times, each for 2-4 hr), mixing extractive solutions, filtering, and concentrating under reduced pressure to obtain concentrated solution;
(2) dispersing the above concentrated solution in water, extracting with ethyl acetate for several times (such as 2-4 times), mixing water phases, and concentrating under reduced pressure to obtain water concentrated solution;
(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 resin amount is 1:5), eluting by 35% ethanol for 6BV, and discarding; eluting with 55% ethanol for 5BV, collecting one third or one fourth eluate as a fraction, detecting 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 (ratio of sample amount to resin amount in column is 1:8), eluting with 30% ethanol for 4BV, and discarding; eluting with 50% ethanol for 5BV, collecting the eluate by half or one third as fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure until no alcohol smell exists to obtain cornuside concentrate;
FIG. 1 is a high performance liquid chromatogram of cornuside raw material drug, and the determination method comprises: the detection system comprises: an Agi l ent Techno l ogens 1260I nfi nity type II HPLC instrument; a chromatographic column: sonoma C18(2) (250X 4.6mm, 5 μm); mobile phase: methanol/water (50:50-95:5, V/V, 50 min); sample introduction amount: 20 mu L of the solution; flow rate: 1.0 mL/min; detection wavelength: 280 nm; column temperature: at 25 ℃.
(4) Dissolving the cornuside concentrate with appropriate amount of ethyl acetate-ethanol (3:7), standing for crystallization, washing off impurities on the crystal surface with appropriate amount of ethanol, recrystallizing for several times (for example, for 2-4 times), and drying under reduced pressure to obtain cornuside raw material with a yield of 0.11% of about 0.55 g.
The preparation method of cornus officinalis neo-glycoside of the invention has been described by specific examples, and those skilled in the art can use the content of the invention to change the links of raw materials, process conditions and the like appropriately to achieve other corresponding purposes, and the related changes do not depart from the content of the invention, 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 invention.
Example two
(1) Pulverizing Corni fructus into powder, adding 40% ethanol, reflux-extracting for several times (such as 2-4 times, each for 2-4 hr), mixing extractive solutions, filtering, and concentrating under reduced pressure to obtain concentrated solution;
(2) dispersing the above concentrated solution in water, extracting with ethyl acetate for several times (such as 2-4 times), mixing water phases, and concentrating under reduced pressure to obtain water concentrated solution;
(3) slowly loading the extracted water concentrated solution into an AB-8 macroporous adsorption resin column, filling the column by a wet method (the ratio of the sample amount to the resin amount in the column is 1:5), eluting by 35% ethanol for 6BV, and discarding; eluting with 55% ethanol for 5BV, collecting one third or one fourth eluate as a fraction, detecting with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure to obtain concentrated solution (density of 1.10); loading the concentrated solution into 60-100 mesh alcohol-soluble polyamide resin column, wet-packing (ratio of sample amount to resin amount in column is 1:8), eluting with 30% ethanol for 4BV, and discarding; eluting with 50% ethanol for 5BV, collecting the eluate by half or one third as fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure until no alcohol smell exists to obtain cornuside concentrate;
(4) dissolving the cornuside concentrate with appropriate amount of ethyl acetate-ethanol (4:6), standing for crystallization, washing off impurities on the crystal surface with appropriate amount of ethanol, recrystallizing for several times (for example, for 2-4 times), and freeze drying to obtain cornuside raw material with purity of about 0.50g and yield of 0.10%.
EXAMPLE III
(1) Pulverizing Corni fructus into coarse powder, extracting with 60% ethanol under reflux for several times (such as 2-4 times, each for 3 hr), mixing extractive solutions, filtering, and concentrating under reduced pressure to obtain concentrated solution;
(2) dispersing the above concentrated solution in water, extracting with ethyl acetate for several times (such as 2-4 times), mixing water phases, and concentrating under reduced pressure to obtain water concentrated solution;
(3) slowly loading the extracted water concentrate into an HP-20 macroporous adsorption resin column, filling the column by a wet method (the ratio of the sample amount to the resin amount in the column is 1:5), eluting by 35% ethanol for 6BV, and discarding; eluting with 55% ethanol for 5BV, collecting one third or one fourth eluate as a fraction, detecting 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 1.13); loading the concentrated solution into 60-100 mesh alcohol-soluble polyamide resin column, wet-packing (ratio of sample amount to resin amount in column is 1:8), eluting with 30% ethanol for 4BV, and discarding; eluting with 50% ethanol for 5BV, collecting the eluate by half or one third as fraction, checking with silica gel thin layer chromatography or HPLC, collecting and mixing eluates containing cornuside, and concentrating under reduced pressure until no alcohol smell exists to obtain cornuside concentrate;
(4) dissolving the cornuside concentrate with appropriate amount of ethyl acetate-ethanol (2:8), standing for crystallization, washing off impurities on the crystal surface with appropriate amount of ethanol, recrystallizing for several times (for example, for 2-4 times), and spray drying to obtain cornuside raw material with purity of about 0.45g, and yield of 0.09%.
In addition, in order to further compare the effect of selecting a specific preparation method of the invention, since the yield of cornuside in example one is as high as 0.11% and the purity is as high as 99.5%, the following comparative examples are specially set for comparison with the first example of the application, and the specific results are also shown in table 1 below. Wherein, the dosage of the cornus officinalis powder in all the examples and the comparative examples is the same.
Comparative example 1: the same as the first embodiment except that the organic solvent is not used for extraction before the macroporous adsorbent resin column. The comparative example shows that the purity of the finally obtained cornuside is only 80.3% without adopting organic solvent extraction before the macroporous adsorption resin column, and the effect is not as good as the purity of the cornuside raw material medicine prepared by the invention.
Comparative example 2: the method is the same as the first embodiment except that a macroporous adsorption resin column is not adopted for chromatography; the comparative example shows that the purity of the finally obtained cornuside is only 82.7% without adopting macroporous adsorption resin column chromatography, and the effect is not as good as that of the raw material medicine of the cornuside prepared by the invention.
Comparative example 3: the method is the same as the first embodiment except that the polyamide resin column is not used for chromatography; the comparative example shows that the purity of the cornuside finally obtained without adopting polyamide resin column chromatography is only 84.5%, and the effect is not as good as that of the cornuside raw material medicine prepared by the invention.
Comparative example 4: the same as the first embodiment except that the macroporous adsorption resin column and the polyamide resin column are not eluted by ethanol water; the comparative example shows that the purity of the finally obtained cornuside is only 89.5% without adopting ethanol water to elute the macroporous adsorption resin column and the polyamide resin column, and the effect is not as good as the purity of the cornuside raw material medicine prepared by the invention.
Comparative example 5: the method is the same as the first embodiment except that recrystallization is not adopted; the comparative example shows that the purity of the finally obtained cornuside without recrystallization is only 91.8 percent, and the effect is not as good as that of the raw material medicine of the cornuside prepared by the invention.
Comparative example 6: the method is as in the first embodiment except that the extraction solvent in the first step is water; the comparative example shows that the yield of the finally obtained cornuside is only 0.07% without adopting the preferable extraction solvent, and the effect is inferior to that of the application;
comparative example 7: the same as in the first embodiment except that the extraction solvent in the first step is 20% ethanol; this comparative example shows that the yield of cornuside finally obtained by extraction with a solvent lower than the range of the preferred extraction solvent ratio is only 0.06%, and the effect is inferior to that of the present application.
Comparative example 8: the second embodiment is the same except that the organic solvent for extraction in the second step is n-butanol; the comparative example shows that the yield of cornuside finally obtained without ethyl acetate extraction is only 0.05%, and the effect is inferior to that of the application.
Comparative example 9: the same procedure as in example three except that the organic solvent used in the extraction in step three is dichloromethane; the comparative example shows that the yield of cornuside finally obtained without ethyl acetate extraction is only 0.06%, and the effect is inferior to that of the application.
Comparative example 10: the same as the first embodiment except that the macroporous adsorbent resin column is DA 201; the comparative example shows that the yield of the cornuside finally obtained by performing column chromatography without adopting the preferred macroporous adsorption resin is only 0.04%, the purity is only 95.0%, and the effect is inferior to that of the application.
Table 1 comparative experiment results table
As can be seen from the table 1, the process flow applied by the invention is simple, the sample loss is less, the environmental pollution is less, the solvent and the time are saved, the yield and the purity of the cornuside raw material medicine are high, and the method is more suitable 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 adsorption resin-polyamide resin-recrystallization, etc., and the specific selection of the process conditions during the preparation, etc., according to the present invention, have an important influence on the yield and purity of the final product. The first embodiment has the best effect.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A preparation method of cornuside raw material medicine is characterized by comprising the following steps:
the method comprises the following steps: crushing dogwood fruits to obtain dogwood powder, adding an extraction solvent into the dogwood powder, performing reflux extraction to obtain an extracting solution, filtering, and performing reduced pressure concentration to obtain a 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: subjecting the extracted water concentrate to macroporous adsorbent resin column chromatography and polyamide resin column chromatography in sequence, performing gradient elution with eluting solvent, performing silica gel thin layer chromatography or HPLC, collecting eluate containing cornuside, and concentrating under reduced pressure to obtain cornuside concentrate;
step four: recrystallizing with dichloromethane, chloroform, ethyl acetate, propyl acetate, acetone, n-butanol, ethanol, methanol or their mixture, and drying to obtain cornuside.
2. The method for preparing cornuside drug substance according to claim 1, wherein the eluting solvent in step three is selected from water, methanol, ethanol, acetone or their mixture.
3. The method for preparing cornuside bulk drug according to claim 1, wherein in the second step, the concentrated solution is extracted with organic solvent for 3-5 times, the aqueous phases are combined and concentrated under reduced pressure to obtain the extracted aqueous concentrated solution; the organic solvent is petroleum ether, cyclohexane, dichloromethane, trichloromethane, 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 concentrated solution after extraction is 1.05-1.30.
4. The method for preparing cornuside bulk drug according to claim 1, wherein in the first step, the amount of the added extraction solvent is 8-15 times of the mass of cornus officinalis powder, the reflux extraction is performed 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 the concentrated solution.
5. The method for preparing cornuside drug substance according to claim 1, wherein the extraction solvent in step one is selected from water, methanol, ethanol or their mixture; the extraction temperature is 70 ℃ to the boiling temperature of the extraction solvent; the density of the prepared concentrated solution is 1.00-1.30.
6. The method for preparing cornuside drug substance according to claim 1, wherein the concentration of ethanol is 0-90% when the extraction solvent in the first step is a mixture of water and ethanol.
7. The method for preparing cornuside bulk drug according to claim 1, wherein in the first step, the extraction solvent is a mixture of water and ethanol, and the concentration of ethanol after mixing is 35-60%; preferably, the amount of the extraction solvent is 10 times of the mass of the dogwood powder.
8. The method for preparing cornuside drug substance according to claim 1, wherein in the second step, the organic solvent is ethyl acetate.
9. The method for preparing cornuside bulk drug according to claim 1, wherein in step three, the macroporous adsorbent resin is preferably D101; the polyamide resin is preferably an alcohol-soluble polyamide resin.
10. The method for preparing cornuside drug substance according to claim 1, wherein the eluting solvent is a mixture of water and ethanol, and the concentration of ethanol after mixing is 30-80%.
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| CN115040558A (en) * | 2022-06-25 | 2022-09-13 | 浙江双糖生物科技有限公司 | Natural extract for reducing blood sugar and application thereof in preparing medicine products for treating diabetes and metabolic syndrome |
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| CN115040558A (en) * | 2022-06-25 | 2022-09-13 | 浙江双糖生物科技有限公司 | Natural extract for reducing blood sugar and application thereof in preparing medicine products for treating diabetes and metabolic syndrome |
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