CN1241904C - Method for preparing active ingredient of sinapine - Google Patents
Method for preparing active ingredient of sinapine Download PDFInfo
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- CN1241904C CN1241904C CN 200410018237 CN200410018237A CN1241904C CN 1241904 C CN1241904 C CN 1241904C CN 200410018237 CN200410018237 CN 200410018237 CN 200410018237 A CN200410018237 A CN 200410018237A CN 1241904 C CN1241904 C CN 1241904C
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Abstract
The present invention discloses a preparation method for extracting sinapine active components from radish seeds, which belongs to the technical field of natural medicament. In the preparation method, radish seeds re taken as the raw materials; sinapine active components with the purity of 80 to 99% are obtained through the steps of extraction, separation, purification, etc. The preparation method has the advantages of simple technology and abundant raw materials, and is suitable for large-scale industrialized production.
Description
Technical field:
The invention belongs to natural medicine technical field.Be specifically related to a kind of preparation method who extracts the sinapic acid choline ester active ingredient from Semen Raphani.
Background technology:
Semen Raphani (Semen Raphani) is the dry mature seed of cress radish (Raphanussativus), and Semen Raphani claims Semen Raphani again.According to successive dynasties TCM Document record, Semen Raphani has out a surname's lung qi, relaxes bowel, and regulates the effect of the whole ascending or descending movement of vital Qi of human body.Modern medicine studies show that Semen Raphani has multiple pharmacologically active effect, as antibiotic, staphylococcus and intestinal bacteria is had significant inhibitory effect, hypotensive effect and Antitussive and Expectorant Effect.Studies have shown that the hypotensive activity composition in the Semen Raphani medicinal material is sinapic acid choline ester (sinapine), and sinapic acid choline ester formation vitriol is more stable, better active, its molecular structural formula is as follows:
According to present research data, mainly lay particular emphasis on the pharmacological research aspect about the research of sinapic acid choline ester composition, the discovery sinapic acid choline esters such as Gu Ruiqi of Shanghai plant physiology institute of the Chinese Academy of Sciences have tangible radioprotective injury effect, can be used as a kind of radiation protective.But, still there is not its preparation process of clearly reporting about the sinapic acid choline ester composition at present about the Study on Preparation of sinapic acid choline ester composition.
Summary of the invention:
Technical problem to be solved by this invention is the preparation method of research and design sinapic acid choline ester active ingredient.
The invention provides a kind of preparation method from Semen Raphani extraction sinapic acid choline ester active ingredient, this method comprises the following steps:
(1) extracts: choose the Semen Raphani raw material of 500g, grind and obtain meal.The alcohol immersion three times that in meal, adds 3-4 times of 85-95% concentration, each soak time 3-4 days, obtain soak solution, merge decompression recycling ethanol, obtain Semen Raphani crude extract medicinal extract 62.45g, add the H of 300-400ml then
2SO
4Solution dissolving control pH2-3, centrifugal removal precipitation obtains centrifugal back solution 280ml;
(2) separation and purification: the solution for obtaining after the centrifugation step (1), to wherein adding perchlorate 3.5g, staticly settle, the throw out after the filtration is drained weight 22.64g.Last silicagel column (100-200 order), flow rate control is carried out wash-out at 10-20ml/min with acetone, collects elutriant to colourless, merges elutriant and is recycled to 300ml, adds 3/4～1/4 times H
2O fully stirs in 30-40 ℃, separates out fully to precipitation, filters collecting precipitation;
(3) make finished product: add anhydrous diethyl ether 100ml and dissolve in the precipitation that step (2) obtains, solvent temperature is controlled at 55-65 ℃, and lysate is placed on and refrigerates crystallization in the refrigerator-freezer, and recrystallization is carried out in the crystallization that obtains, and obtains sinapic acid choline ester 0.32g;
(4) detect:, analyze and obtain the purity of sinapic acid choline ester in the scope of 80-99% through the content detection of HPLC.
The sinapic acid choline ester active ingredient purity that makes by method of the present invention is 80～99%.
Preparation technology of the present invention is simple, the yield height, and raw material resources are abundant, and cost is low, and the product purity height is suitable for the suitability for industrialized production of scale.
The sinapic acid choline ester activeconstituents that makes by the inventive method detects the product purity height that makes through HPLC, and is 310.15 through MS detection molecules amount, conforms to theoretical value.
Description of drawings:
The HPLC of Fig. 1, sinapic acid choline ester detects figure
Sample title: sinapic acid choline ester
Chromatographic column: LiChoCART 250*4 LiChrospher 100 RP-18e (5um)
Moving phase: methyl alcohol: acetonitrile: potassium primary phosphate (0.08M)=10: 12: 78
Wavelength: 326nm
Temperature: 25 ℃
Flow velocity: 0.5 ml/min
Sensitivity: 0.005 AUFS
Method of calculation: area normalization method
Analytical results:
| Retention time | Peak area | Area content | Peak heights | Peak heights per-cent |
| 1.267 | 90647 | 1.53 | 10004 | 2.72 |
| 1.817 | 5487 | 0.09 | 452 | 0.12 |
| 2.692 | 54590 | 0.92 | 3161 | 0.86 |
| 3.558 | 9507 | 0.16 | 1184 | 0.32 |
| 3.908 | 14010 | 0.24 | 1512 | 0.41 |
| 4.342 | 6520 | 0.11 | 719 | 0.20 |
| 10.208 | 5741738 | 96.95 | 350737 | 95.37 |
| Totals | ||||
| 5922499 | 100.00 | 367769 | 100.00 |
Embodiment:
Embodiment one
Get the Semen Raphani raw material of 300g, grind and obtain meal.Add the alcohol immersion three times of 3 times of amount 85% concentration in meal, each soak time 3 days obtains soak solution, merges decompression recycling ethanol, obtains Semen Raphani crude extract medicinal extract 30.8g, adds the H of 200ml then
2SO
4(PH=2) solution dissolving, centrifugal removal precipitation obtains centrifugal back solution 180ml.
For the solution that obtains after centrifugal, to wherein adding perchlorate 2.0g, leave standstill and obtain precipitation, throw out after the filtration is drained silicagel column (100-200 order), flow rate control is carried out wash-out at 15ml/min with acetone, collects elutriant to colourless, merge elutriant and be recycled to 200ml, add the H of 100ml
2O fully stirs in 30 ℃, separates out fully to precipitation, obtains precipitation after the filtration.
Add anhydrous diethyl ether 50ml and dissolve in precipitation, solvent temperature is controlled at 55 ℃, and lysate is placed in the refrigerator-freezer and refrigerates, and leaves standstill to obtain crystallization, obtains sinapic acid choline ester finished product 0.18g, and purity is 85%.
Embodiment two
Get the Semen Raphani raw material of 1kg, grind and obtain meal.Add the alcohol immersion three times of 3 times of amount 90% concentration in meal, each soak time 4 days obtains soak solution, merges decompression recycling ethanol, obtains Semen Raphani crude extract medicinal extract 106.6g, adds the H of 500ml then
2SO
4(PH=2) solution dissolving, centrifugal removal precipitation obtains centrifugal back solution 510ml.
For the solution that obtains after centrifugal, to wherein adding perchlorate 10.0g, leave standstill and obtain precipitation, throw out after the filtration is drained silicagel column (100-200 order), flow rate control is carried out wash-out at 15ml/min with acetone, collects elutriant to colourless, merge elutriant and be recycled to 700ml, add the H of 400ml
2O fully stirs in 35 ℃, separates out fully to precipitation, obtains precipitation after the filtration.
Add anhydrous diethyl ether 200ml and dissolve in precipitation, solvent temperature is controlled at 60 ℃, and lysate is placed in the refrigerator-freezer and refrigerates, and leaves standstill crystallization, and the crystallisate that obtains carries out recrystallization, obtains sinapic acid choline ester finished product 0.58g, and purity is 95%.
Embodiment three
Get the Semen Raphani raw material of 2kg, grind and obtain meal.Add the alcohol immersion three times of 4 times of amount 95% concentration in meal, each soak time 3.5 days obtains soak solution, merges decompression recycling ethanol, obtains Semen Raphani crude extract medicinal extract 226.2g, adds the H of 900ml then
2SO
4(PH=2) solution dissolving, centrifugal removal precipitation obtains centrifugal back solution 920ml.
For the solution that obtains after centrifugal, to wherein adding perchlorate 18.0g, leave standstill and obtain precipitation, throw out after the filtration is drained silicagel column (100-200 order), flow rate control is carried out wash-out at 18ml/min with acetone solvent, collects elutriant to colourless, merge elutriant and be recycled to 1200ml, add the H of 600ml
2O fully stirs in 40 ℃, separates out fully to precipitation, obtains precipitation after the filtration.
Add anhydrous diethyl ether 350ml and dissolve in precipitation, solvent temperature is controlled at 65 ℃, and lysate is placed in the refrigerator-freezer and refrigerates, and leaves standstill crystallization, and the crystallisate that obtains carries out recrystallization, obtains sinapic acid choline ester finished product 1.02g, and content detection is 96.95%.
Claims (1)
1, a kind of preparation method from Semen Raphani extraction sinapic acid choline ester activeconstituents is characterized in that this method comprises the following steps:
(1) extracts: choose the Semen Raphani raw material of 500g, grind and obtain meal, in meal, add the alcohol immersion three times of 3-4 times of 85-95% concentration, each soak time 3-4 days, obtain soak solution, merge decompression recycling ethanol, obtain Semen Raphani crude extract medicinal extract 62.45g, add the H of 300-400ml then
2SO
4Solution dissolving control pH2-3, centrifugal removal precipitation obtains centrifugal back solution 280ml;
(2) separation and purification: for the solution that obtains after the centrifugation step (1), to wherein adding perchlorate 3.5g, staticly settle, throw out after the filtration is drained weight 22.64g, last silicagel column, and flow rate control is at 10-20ml/min, carry out wash-out with acetone, collect elutriant to colourless, merge elutriant and be recycled to 300ml, add 3/4～1/4 times H
2O fully stirs in 30-40 ℃, separates out fully to precipitation, filters collecting precipitation;
(3) make finished product: add anhydrous diethyl ether 100ml and dissolve in the precipitation that step (2) obtains, solvent temperature is controlled at 55-65 ℃, and lysate is placed on and refrigerates crystallization in the refrigerator-freezer, and recrystallization is carried out in the crystallization that obtains, and obtains sinapic acid choline ester 0.32g.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410018237 CN1241904C (en) | 2004-05-11 | 2004-05-11 | Method for preparing active ingredient of sinapine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410018237 CN1241904C (en) | 2004-05-11 | 2004-05-11 | Method for preparing active ingredient of sinapine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1569814A CN1569814A (en) | 2005-01-26 |
| CN1241904C true CN1241904C (en) | 2006-02-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410018237 Expired - Fee Related CN1241904C (en) | 2004-05-11 | 2004-05-11 | Method for preparing active ingredient of sinapine |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101606750B (en) * | 2008-06-16 | 2012-02-08 | 湖北中烟工业有限责任公司 | Radish seed extract and application thereof as tobacco product additive |
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Granted publication date: 20060215 |