CN103450212A - Preparation method of deoxyelephantopin - Google Patents
Preparation method of deoxyelephantopin Download PDFInfo
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- CN103450212A CN103450212A CN 201310343930 CN201310343930A CN103450212A CN 103450212 A CN103450212 A CN 103450212A CN 201310343930 CN201310343930 CN 201310343930 CN 201310343930 A CN201310343930 A CN 201310343930A CN 103450212 A CN103450212 A CN 103450212A
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- deoxyelephantopin
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- methanol solution
- ethyl acetate
- macroporous resin
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Abstract
The invention discloses a preparation method of deoxyelephantopin, which comprises the following steps: pulverizing a herba elephantopi raw material, adding 5-10 times of 60-90% methanol solution, and performing ultrasonic extraction 2-3 times; adding activated carbon into the extracting solution, decolorizing under reflux, filtering out the activated carbon, concentrating, and adding into a macroporous resin column for adsorption; eluting with 5-10 times (column volume) of 50-90% methanol solution, concentrating the eluate, and extracting with an ethyl acetate solution; and collecting the extract, recovering reagents, separating with a high-speed counter-current chromatographic instrument, performing on-line monitoring through an ultraviolet detector, collecting the fractions, and drying under reduced pressure. The preparation method of deoxyelephantopin is convenient in technological operation, less in pollution and suitable for preparation of high-purity deoxyelephantopin.
Description
Technical field
The invention belongs to the Natural Medicine Chemistry field, particularly a kind of preparation method of deoxyelephantopin.
Background technology
Deoxyelephantopin, CAS 29307-03-7, molecular formula C19H20O6, molecular weight 344.3, molecular structural formula is as follows:
Deoxyelephantopin belongs to sesquiterpenoids, colourless needle crystal (chloroform), fusing point > 320 ℃ (198～200 ℃ are softening).Derive from feverfew Elephantopus scaber L. (Elephantopus scaber L.) herb, experimentation on animals shows to have significant antitumour activity.
By literature search, the open silicagel columns that adopt that have the deoxyelephantopin preparation method now separate more, and because the silicagel column separation exists, sample loss is large, poor reproducibility, and seriously polluted, is not to be applicable to industrialization.
Summary of the invention
The objective of the invention is to solve shortcomings and deficiencies of the prior art, a kind of preparation method of deoxyelephantopin is provided.
To achieve these goals, the present invention is by the following technical solutions:
A kind of preparation method of deoxyelephantopin, it is characterized in that: get the Elephantopus scaber L. raw material pulverizing, add 5-10 doubly to measure 60%-90% methanol solution supersound extraction 2-3 time, extracting solution adds the gac reflux decolour, leach after gac concentrates to add in macroporous resin column and adsorb, with 5-10 times of column volume 50%-90% methanol solution wash-out, after elutriant is concentrated, with ethyl acetate solution, extract, collecting extraction liquid recovery reagent separates with high-speed counter-current chromatograph again, the UV-detector on-line monitoring, collect the flow point drying under reduced pressure and get final product.
A kind of in the optional HZ816 of described macroporous resin, HPD100, AB-8 and D101.
Described high-speed counter-current chromatograph separation condition is: get sherwood oil, ethyl acetate, methyl alcohol, water, press 1-3:2-5:5-9:3-5 and mix, get the phase that fixes mutually, lower be moving phase mutually, engine speed 700-1000rpm, flow velocity is 1-3ml/min.
Adopt this law to prepare deoxyelephantopin, easy and simple to handle, preparation amount is large, and low the pollution, is applicable to suitability for industrialized production.
Further illustrate the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to following embodiment.
Embodiment
Embodiment 1:
Getting Elephantopus scaber L. pulverizes, claim 2kg, each 10L70% methanol solution supersound extraction 30 minutes of using, extract 3 times, and extracting solution adds 200g gac reflux decolour, leaching the gac concentrating under reduced pressure adds in the HZ816 macroporous resin column and adsorbs without alcohol, with 7 times of column volumes, 60% methanol solution wash-out, elutriant is evaporated to 300ml, adds ethyl acetate solution extraction 3 times, extraction liquid reclaims reagent, obtains medicinal extract.Get sherwood oil, ethyl acetate, methyl alcohol, water, press 2:3:5:3 and mix, fully after layering, get and fill with mutually the high speed adverse current chromatogram pipe phase that fixes, open and turn main frame, rotating speed 800rpm pumps into the lower stream phasing of doing mutually simultaneously, after setting up running balance, flow rate regulation is 2ml/min, by moving phase, dissolves medicinal extract, by the sampling valve sample introduction, the UV-detector on-line monitoring, collect target component, continuous production, flow point reclaims reagent, obtains deoxyelephantopin 2.3g, through HPLC, detect, content 98.5%, through UV, IR, MS,
2hNMR,
13the data of its physical behavior of the sign such as CNMR are consistent with prior art.
Embodiment 2:
Getting Elephantopus scaber L. pulverizes, claim 2kg, each 15L90% methanol solution supersound extraction 30 minutes of using, extract 3 times, and extracting solution adds 200g gac reflux decolour, leaching the gac concentrating under reduced pressure adds in the AB-8 macroporous resin column and adsorbs without alcohol, with 8 times of column volumes, 70% methanol solution wash-out, elutriant is evaporated to 200ml, adds ethyl acetate solution extraction 3 times, extraction liquid reclaims reagent, obtains medicinal extract.Get sherwood oil, ethyl acetate, methyl alcohol, water, press 1:3:7:4 and mix, fully after layering, get and fill with mutually the high speed adverse current chromatogram pipe phase that fixes, open and turn main frame, rotating speed 850rpm pumps into the lower stream phasing of doing mutually simultaneously, after setting up running balance, flow rate regulation is 3ml/min, by moving phase, dissolves medicinal extract, by the sampling valve sample introduction, the UV-detector on-line monitoring, collect target component, continuous production, flow point reclaims reagent, obtains deoxyelephantopin 2.6g, through HPLC, detect, content 97.7%, through UV, IR, MS,
2hNMR,
13the data of its physical behavior of the sign such as CNMR are consistent with prior art.
Embodiment 3:
Getting Elephantopus scaber L. pulverizes, claim 2kg, each 10L70% methanol solution supersound extraction 30 minutes of using, extract 3 times, and extracting solution adds 200g gac reflux decolour, leaching the gac concentrating under reduced pressure adds in the D101 macroporous resin column and adsorbs without alcohol, with 5 times of column volumes, 75% methanol solution wash-out, elutriant is evaporated to 200ml, adds ethyl acetate solution extraction 4 times, extraction liquid reclaims reagent, obtains medicinal extract.Get sherwood oil, ethyl acetate, methyl alcohol, water, press 3:5:7:3 and mix, fully after layering, get and fill with mutually the high speed adverse current chromatogram pipe phase that fixes, open and turn main frame, rotating speed 900rpm pumps into the lower stream phasing of doing mutually simultaneously, after setting up running balance, flow rate regulation is 3ml/min, by moving phase, dissolves medicinal extract, by the sampling valve sample introduction, the UV-detector on-line monitoring, collect target component, continuous production, flow point reclaims reagent, obtains deoxyelephantopin 2.4g, through HPLC, detect, content 98.1%, through UV, IR, MS,
2hNMR,
13the data of its physical behavior of the sign such as CNMR are consistent with prior art.
Claims (3)
1. the preparation method of a deoxyelephantopin, it is characterized in that: get the Elephantopus scaber L. raw material pulverizing, add 5-10 doubly to measure 60%-90% methanol solution supersound extraction 2-3 time, extracting solution adds the gac reflux decolour, leach after gac concentrates to add in macroporous resin column and adsorb, with 5-10 times of column volume 50%-90% methanol solution wash-out, after elutriant is concentrated, with ethyl acetate solution, extract, collecting extraction liquid recovery reagent separates with high-speed counter-current chromatograph again, the UV-detector on-line monitoring, collect the flow point drying under reduced pressure and get final product.
2. the preparation method of deoxyelephantopin according to claim 1, is characterized in that a kind of in the optional HZ816 of described macroporous resin, HPD100, AB-8 and D101.
3. the preparation method of deoxyelephantopin according to claim 1, it is characterized in that described high-speed counter-current chromatograph separation condition is: get sherwood oil, ethyl acetate, methyl alcohol, water, pressing 1-3:2-5:5-9:3-5 mixes, get the phase that fixes mutually, lower mutually for moving phase, engine speed 700-1000rpm, flow velocity is 1-3ml/min.
Priority Applications (1)
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| CN 201310343930 CN103450212A (en) | 2013-08-09 | 2013-08-09 | Preparation method of deoxyelephantopin |
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| CN 201310343930 CN103450212A (en) | 2013-08-09 | 2013-08-09 | Preparation method of deoxyelephantopin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107072981A (en) * | 2014-06-07 | 2017-08-18 | 中央研究院 | Sesquiterpene ene derivative and its purposes in inflammation and treatment of cancer |
| CN111909165A (en) * | 2020-08-13 | 2020-11-10 | 淮安泰凯睿医药科技有限公司 | Method for simultaneously preparing elephantopin and allopatricolone |
-
2013
- 2013-08-09 CN CN 201310343930 patent/CN103450212A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107072981A (en) * | 2014-06-07 | 2017-08-18 | 中央研究院 | Sesquiterpene ene derivative and its purposes in inflammation and treatment of cancer |
| CN107072981B (en) * | 2014-06-07 | 2021-02-02 | 中央研究院 | Novel sesquiterpene derivatives and their use in the treatment and/or prevention of inflammation and in the treatment of cancer |
| CN111909165A (en) * | 2020-08-13 | 2020-11-10 | 淮安泰凯睿医药科技有限公司 | Method for simultaneously preparing elephantopin and allopatricolone |
| CN111909165B (en) * | 2020-08-13 | 2022-12-06 | 江西永通科技股份有限公司 | Method for simultaneously preparing elephantopin and allopatricolone |
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Application publication date: 20131218 |
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| WD01 | Invention patent application deemed withdrawn after publication |