CN104804011A - Method for separating and purifying isoimperatorin and imperatorin from angelica dahurica - Google Patents
Method for separating and purifying isoimperatorin and imperatorin from angelica dahurica Download PDFInfo
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- CN104804011A CN104804011A CN201510179399.9A CN201510179399A CN104804011A CN 104804011 A CN104804011 A CN 104804011A CN 201510179399 A CN201510179399 A CN 201510179399A CN 104804011 A CN104804011 A CN 104804011A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention provides a method for separating and purifying isoimperatorin and imperatorin from angelica dahurica. The method comprises the following steps: crude angelica dahurica medicine is ground, petroleum ether is added, the mixture is subjected to backheating and refluxing, and an extracting solution is filtered and subjected to pressure reduction concentration to obtain an angelica dahurica extract; the angelica dahurica extract is dissolved with methanol, the mixture is filtered, a filtering product is subjected to supercritical fluid chromatographic separation, a chromatographic column adopts the C18 chromatographic column, a mobile phase adopts a supercritical fluid, and an improving agent adopts the methanol. An organic solvent harmful to the environment is not used, the production process is environment-friendly, and a product is free of residual hazardous substances; carbon dioxide is easy to recycle, and the energy consumption and the production cost are low.
Description
Technical field
The invention belongs to chemical industry and pharmacy field, specifically relate to a kind of method of separation and purification Isoimperatorin and pentosalen from Radix Angelicae Dahuricae extract.
Background technology
The root of Dahurain angelica is conventional Chinese medicine, has the effect of the dehumidifying of loose wind, understand things pain-stopping, detumescence and apocenosis, the disease such as be widely used in treatment cold headache clinically, Supraorbital bone pain, nasal obstruction, nasosinusitis, toothache, leukorrhea and sore swell and ache.Tonka bean camphor is the main active ingredient in the root of Dahurain angelica, and what wherein content was higher has pentosalen and Isoimperatorin, and these two kinds of materials are also the leading indicators that the root of Dahurain angelica and the quality of the pharmaceutical preparations thereof control.
Traditional separation purification method of coumarins composition in the root of Dahurain angelica, adopts ether, sherwood oil equal solvent to extract, silica gel column chromatography purifying more, this method step is numerous and diverse, organic solvent consumption is large, dissolvent residual is many in product.In recent years, there is again the coumarins composition adopted in the high speed adverse current chromatogram separation and purification root of Dahurain angelica, although it is applied widely, do not need solid-state carrier, require low to the pre-treatment of sample, but its solvent systems selects difficulty large, also have that organic solvent-oil ratio is large, the shortcomings such as dissolvent residual is many in product, be difficult to realize green cleaner production.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, there is provided a kind of easy and simple to handle, fractional dose is large, comprehensive cost is low, the fast purifying from the root of Dahurain angelica of environmental protection prepares the method for Isoimperatorin and pentosalen, can obtain high purity Isoimperatorin and pentosalen monomeric compound by a step separation and purification from Radix Angelicae Dahuricae extract.
The solution of the present invention is as follows:
A method for separation and purification Isoimperatorin and pentosalen from Radix Angelicae Dahuricae extract, step is:
Step 1: angelica root is pulverized, and adds sherwood oil, backheat backflow will be extracted.Liquid filters, concentrating under reduced pressure obtains root of Dahurain angelica medicinal extract.
Step 2: by root of Dahurain angelica medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is C18 chromatographic column, and moving phase is supercutical fluid, and improving agent is methyl alcohol.Sepn process is detected by UV-detector, collects target components cut according to detection signal.
Foregoing method, preferred scheme is, the ratio that step 1 PetroChina Company Limited. ether extracts sherwood oil and medicinal material is 3:1 ~ 10:1, and optimum is 6:1; The number of times extracted is 3 times, and each return time is 0.5-5 hour, and optimum is 2 hours.
Foregoing method, preferred scheme is, filtering filter membrane used in step 2 is 0.45 μm of filter membrane.
Foregoing method, preferred scheme is, in step 2, supercutical fluid is supercritical co, and the pressure of supercritical co is 10 ~ 15MPa, and optimum is 12MPa; The flow velocity of supercritical co be 1-10 times of column volume/minute, optimum be 4 times of column volumes/minute.
Foregoing method, preferred scheme is, in step 2, chromatogram column temperature is 35 ~ 50 ° of C, and optimum is 35 ° of C.
Foregoing method, preferred scheme is, in step 2, the ratio of improving agent methyl alcohol is 0% ~ 10%, and optimum is 1.15%.
The method of the present invention a kind of separation and purification Isoimperatorin and pentosalen from the root of Dahurain angelica, has following advantage:
(1) active constituent content high (as can be seen from Figure 1) in the Radix Angelicae Dahuricae extract obtained.
(2) do not need to carry out separating for several times purifying to sample as prior art, only need a separating step can obtain two kinds of high-purity compounds, just can obtain Isoimperatorin and pentosalen through a step separation and purification.
(3) use supercritical co in purge process, do not use organic solvent environment being had to harm, production process environmental protection, products obtained therefrom unharmful substance remains.
(4) carbon dioxide recovery utilizes easily, and energy consumption is low, and production cost is low.
(5) method is simple to operate, is easy to Automated condtrol, and efficiency is high, and process cycle is short.
Accompanying drawing explanation
Fig. 1 is embodiment 1 supercritical fluid chromatography figure.
Embodiment
Describe technical scheme of the present invention in detail below in conjunction with embodiment and accompanying drawing, but protection domain is not by this restriction.In embodiment, equipment used or starting material all can obtain from market.Agents useful for same is analytical pure, and purchased from Tianjin reagent four factory, carbonic acid gas used is high-purity carbon dioxide.
Embodiment 1
Take the root of Dahurain angelica 500 grams, pulverize, put into Glass Containers, add 3000ml sherwood oil, heating and refluxing extraction 3 times with pulverizer, each backflow 2 hours, united extraction liquid, filtration, concentrating under reduced pressure obtain root of Dahurain angelica medicinal extract.
By root of Dahurain angelica medicinal extract dissolve with methanol, after filtration after (filter membrane used is 0.45 μm of filter membrane), carry out supercritical fluid chromatography separation, chromatographic column is C18 chromatographic column, and chromatogram column temperature is 35 ° of C.Moving phase is supercritical co, flow velocity be 4 times of column volumes/minute, pressure is 12MPa.Improving agent is methyl alcohol, and its ratio is 1.15%.Sepn process is detected by UV-detector, and determined wavelength is 220nm, collects target components cut, obtain Isoimperatorin and pentosalen respectively according to detection signal.
Fig. 1 is products therefrom supercritical fluid chromatography figure.It can thus be appreciated that products therefrom purity is very high.
Embodiment 2
Take the root of Dahurain angelica 500 grams, pulverize, put into Glass Containers, add 4000ml sherwood oil, heating and refluxing extraction 3 times hours with pulverizer, each backflow 1 hour, united extraction liquid, filtration, concentrating under reduced pressure obtain root of Dahurain angelica medicinal extract.
By root of Dahurain angelica medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is C18 chromatographic column, and chromatogram column temperature is 42 ° of C.Moving phase is supercritical co, flow velocity be 3.5 times of column volumes/minute, pressure is 13MPa.Improving agent is methyl alcohol, and its ratio is 1.35%.Sepn process is detected by UV-detector, and determined wavelength is 220nm, collects target components cut, obtain Isoimperatorin and pentosalen respectively according to detection signal.
Embodiment 3
Take the root of Dahurain angelica 500 grams, pulverize, put into Glass Containers, add 2200ml sherwood oil, heating and refluxing extraction 3 times hours with pulverizer, each backflow 3 hours, united extraction liquid, filtration, concentrating under reduced pressure obtain root of Dahurain angelica medicinal extract.
By root of Dahurain angelica medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is C18 chromatographic column, and chromatogram column temperature is 38 ° of C.Moving phase is supercritical co, flow velocity be 2.5 times of column volumes/minute, pressure is 11MPa.Improving agent is methyl alcohol, and its ratio is 0.95%.Sepn process is detected by UV-detector, and determined wavelength is 220nm, collects target components cut, obtain Isoimperatorin and pentosalen respectively according to detection signal.
Through HPLC area normalization method analytical test, the purity of each component that embodiment 1-3 obtains is very high, all more than 98%.
Identify through NMR, MS.In Fig. 1, A is Isoimperatorin, and B is pentosalen, and its chemical structure is as follows:
Claims (9)
1. the method for separation and purification Isoimperatorin and pentosalen from Radix Angelicae Dahuricae extract, it is characterized in that, step is:
Step 1: angelica root is pulverized, and adds sherwood oil, extracting liquid filtering, concentrating under reduced pressure are obtained root of Dahurain angelica medicinal extract by backheat backflow;
Step 2: by root of Dahurain angelica medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is C18 chromatographic column, and moving phase is supercutical fluid, and improving agent is methyl alcohol, sepn process is detected by UV-detector, collects target components cut according to detection signal.
2. method according to claim 1, is characterized in that, the ratio of step 1 PetroChina Company Limited. ether and medicinal material is 3:1 ~ 10:1, and optimum is 6:1.
3. method according to claim 1, is characterized in that, the number of times that step 1 is extracted is 3 times, and each return time is 0.5-5 hour, and optimum is 2 hours.
4. method according to claim 1, is characterized in that, filtering filter membrane used in step 2 is 0.45 μm of filter membrane.
5. method according to claim 1, is characterized in that, in step 2, supercutical fluid is supercritical co.
6. method according to claim 5, is characterized in that, the pressure of supercritical co is 10 ~ 15MPa, and optimum is 12MPa.
7. method according to claim 5, is characterized in that, the flow velocity of supercritical co be 1-10 times of column volume/minute, optimum be 4 times of column volumes/minute.
8. method according to claim 1, is characterized in that, in step 2, chromatogram column temperature is 35 ~ 50 ° of C, and optimum is 35 ° of C.
9. method according to claim 1, is characterized in that, in step 2, the ratio of improving agent methyl alcohol is 0% ~ 10%, and optimum is 1.15%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510179399.9A CN104804011A (en) | 2015-04-16 | 2015-04-16 | Method for separating and purifying isoimperatorin and imperatorin from angelica dahurica |
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| CN201510179399.9A CN104804011A (en) | 2015-04-16 | 2015-04-16 | Method for separating and purifying isoimperatorin and imperatorin from angelica dahurica |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061448A (en) * | 2015-09-08 | 2015-11-18 | 聊城大学 | Method for extracting, separating and purifying three kinds of coumarin from dahurian angelica root |
| CN105859715A (en) * | 2016-04-27 | 2016-08-17 | 聊城大学 | Critical fluid chromatographic method for separating and purifying evodiamine and rutaecarpine from fructus evodiae |
-
2015
- 2015-04-16 CN CN201510179399.9A patent/CN104804011A/en active Pending
Non-Patent Citations (4)
| Title |
|---|
| C. DESMORTREUX ET AL.: ""Improved separation of furocoumarins of essential oils by supercritical fluid chromatography"", 《JOURNAL OF CHROMATOGRAPHY A》 * |
| 孟兰贞 等: ""色谱技术在中药白芷研究中的应用进展"", 《时珍国医国药》 * |
| 李洁 等: ""香豆素类物质的色谱检测进展"", 《生命科学仪器》 * |
| 邓捷圆 等: ""HPLC 法同时测定不同产地白芷中2 种香豆素的含量"", 《沈阳药科大学学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061448A (en) * | 2015-09-08 | 2015-11-18 | 聊城大学 | Method for extracting, separating and purifying three kinds of coumarin from dahurian angelica root |
| CN105859715A (en) * | 2016-04-27 | 2016-08-17 | 聊城大学 | Critical fluid chromatographic method for separating and purifying evodiamine and rutaecarpine from fructus evodiae |
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Application publication date: 20150729 |