CN101759706B - Method for manufacturing anemonin - Google Patents
Method for manufacturing anemonin Download PDFInfo
- Publication number
- CN101759706B CN101759706B CN2009102329900A CN200910232990A CN101759706B CN 101759706 B CN101759706 B CN 101759706B CN 2009102329900 A CN2009102329900 A CN 2009102329900A CN 200910232990 A CN200910232990 A CN 200910232990A CN 101759706 B CN101759706 B CN 101759706B
- Authority
- CN
- China
- Prior art keywords
- pulsatilla
- preparation
- camphor
- crystal
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- JLUQTCXCAFSSLD-NXEZZACHSA-N Anemonin Chemical compound C1=CC(=O)O[C@]11[C@@]2(C=CC(=O)O2)CC1 JLUQTCXCAFSSLD-NXEZZACHSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- JLUQTCXCAFSSLD-UHFFFAOYSA-N Anemonin Natural products C1=CC(=O)OC11C2(C=CC(=O)O2)CC1 JLUQTCXCAFSSLD-UHFFFAOYSA-N 0.000 title abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 8
- 229940079593 drug Drugs 0.000 claims abstract description 8
- 241000206469 Pulsatilla Species 0.000 claims abstract description 6
- 238000000605 extraction Methods 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 238000001640 fractional crystallisation Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 230000006837 decompression Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 235000012054 meals Nutrition 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 238000005057 refrigeration Methods 0.000 claims description 5
- 238000000194 supercritical-fluid extraction Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 238000004064 recycling Methods 0.000 abstract 2
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- SENMPMXZMGNQAG-UHFFFAOYSA-N 3,4-dihydro-2,5-benzodioxocine-1,6-dione Chemical compound O=C1OCCOC(=O)C2=CC=CC=C12 SENMPMXZMGNQAG-UHFFFAOYSA-N 0.000 description 1
- 241000123887 Pulsatilla chinensis Species 0.000 description 1
- 241000218201 Ranunculaceae Species 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to a method for manufacturing anemonin which has simple operation, small pollution and less investment. The method comprises the steps of: adding the root of Chinese pulsatilla coarse powder into a CO2 supercritical extractor, using ethyl acetate as entrainer which occupies 2 to 6 volume percent of the total extracting solvent, extracting for 100 to 200 min under 10 to 40 MPa at 30 to 60 DEG C with the CO2 flow being 1-5 ml/g crude drug per min so as to acquire the extract, decompressing and recycling the solvent so as to acquire oily matter, refrigerating, dissolving out crystal, separating the crystal, adding heat ethanol, filtering, taking the filtrate, recycling ethanol, placing the crystal, separating the crystal and adding chloroform so as to re-crystallize. The anemonin manufactured by using the method of the invention has high purity and is easy to realize industrialization magnification.
Description
Technical field
The present invention relates to a kind of preparation method of Pulsatilla camphor, especially a kind of method of from plant, extracting Pulsatilla camphor.
Background technology
Pulsatilla camphor (Anemonin), another name: pulsatilla camphor etc.Molecular formula: C10H8O4, molecular weight: 192.171, CAS accession number: 508-44-1, structural formula is following:
Pulsatilla camphor is a kind of natural compounds, has effects such as anticancer, resisting pathogenic microbes, extensively is present in the various plants such as ranunculaceae plant Root of Chinese Pulsatilla Pulsatilla chinensis (Bge.) Regel.
In the prior art, the extraction separation of Pulsatilla camphor mainly adopts organic solvent method etc., but the content of the Pulsatilla camphor that these extraction processes obtain is low, and is seriously polluted in the production process, and unfavorable big production operation.
Summary of the invention
Technical problem to be solved by this invention provides a kind of preparation method who is beneficial to big production operation, Pulsatilla camphor that product purity is high.
For solving the problems of the technologies described above, the present invention adopts following technical proposal:
Get Root of Chinese Pulsatilla herb meal, join CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2-6%, extracting pressure 10-40MPa, temperature 30-60 ℃, CO
2Flow 1-5ml/g crude drug/min, extraction time 100-200min gets extract, decompression and solvent recovery; Get oily matter, refrigeration is separated out crystallization, fractional crystallization; Add the hot ethanol dissolving, filtered while hot is got filtrating, reclaims ethanol; Place crystallization, fractional crystallization adds the chloroform recrystallization, separates, washs, is drying to obtain.
The volume percent that entrainment agent accounts for total extraction solvent is 5%.
Extracting pressure is preferably 20MPa.
Extraction temperature is preferably 45 ℃.
CO
2Flow is preferably 2ml/g crude drug/min.
The extraction time is preferably 150min.
Adopt technique scheme to prepare Pulsatilla camphor, easy and simple to handle, pollute less, equipment drops into for a short time, is beneficial to big production operation.
To combine embodiment that the present invention is done further elaboration below, but the scope that the present invention requires to protect is not limited to following embodiment.
Embodiment
Embodiment 1
Get Root of Chinese Pulsatilla herb meal 10Kg, join CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2%, extracting pressure 10MPa, 30 ℃ of temperature, CO
2Flow 1ml/g crude drug/min, extraction time 100-200min gets extract, and decompression and solvent recovery gets oily matter; Crystallization is separated out in refrigeration, and fractional crystallization adds the hot ethanol dissolving; Filtered while hot is got filtrating, reclaims ethanol, places crystallization; Fractional crystallization adds the chloroform recrystallization, separates, washs, is drying to obtain Pulsatilla camphor 9.0g, detects through HPLC, and purity is 98.9%.
Embodiment 2
Get Root of Chinese Pulsatilla herb meal 10Kg, join CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 6%, extracting pressure 40MPa, 60 ℃ of temperature, CO
2Flow 5ml/g crude drug/min, extraction time 100-200min gets extract, and decompression and solvent recovery gets oily matter; Crystallization is separated out in refrigeration, and fractional crystallization adds the hot ethanol dissolving; Filtered while hot is got filtrating, reclaims ethanol, places crystallization; Fractional crystallization adds the chloroform recrystallization, separates, washs, is drying to obtain Pulsatilla camphor 11.7g, detects through HPLC, and purity is 98.2%.
Embodiment 3
Get Root of Chinese Pulsatilla herb meal 10Kg, join CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 5%, extracting pressure 20MPa, 45 ℃ of temperature, CO
2Flow 2ml/g crude drug/min, extraction time 150min gets extract, and decompression and solvent recovery gets oily matter; Crystallization is separated out in refrigeration, and fractional crystallization adds the hot ethanol dissolving; Filtered while hot is got filtrating, reclaims ethanol, places crystallization; Fractional crystallization adds the chloroform recrystallization, separates, washs, is drying to obtain Pulsatilla camphor 13.0g, detects through HPLC, and purity is 99.7%.
Claims (6)
1. the preparation method of a Pulsatilla camphor is characterized in that described method comprises the following steps: to get Root of Chinese Pulsatilla herb meal, joins CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2-6%, extracting pressure 10-40MPa, temperature 30-60 ℃, CO
2Flow 1-5ml/g crude drug/min, extraction time 100-200min gets extract, decompression and solvent recovery; Get oily matter, refrigeration is separated out crystallization, fractional crystallization; Add the hot ethanol dissolving, filtered while hot is got filtrating, reclaims ethanol; Place crystallization, fractional crystallization adds the chloroform recrystallization, separates, washs, is drying to obtain.
2. according to the preparation method of the said Pulsatilla camphor of claim 1, it is characterized in that the volume percent that said entrainment agent accounts for total extraction solvent is 5%.
3. according to the preparation method of the said Pulsatilla camphor of claim 1, it is characterized in that said extracting pressure is 20MPa.
4. according to the preparation method of the said Pulsatilla camphor of claim 1, it is characterized in that said extraction temperature is 45 ℃.
5. according to the preparation method of the said Pulsatilla camphor of claim 1, it is characterized in that said CO
2Flow is 2ml/g crude drug/min.
6. according to the preparation method of the said Pulsatilla camphor of claim 1, it is characterized in that the said extraction time is 150min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102329900A CN101759706B (en) | 2009-10-20 | 2009-10-20 | Method for manufacturing anemonin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102329900A CN101759706B (en) | 2009-10-20 | 2009-10-20 | Method for manufacturing anemonin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101759706A CN101759706A (en) | 2010-06-30 |
| CN101759706B true CN101759706B (en) | 2012-01-11 |
Family
ID=42491101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009102329900A Active CN101759706B (en) | 2009-10-20 | 2009-10-20 | Method for manufacturing anemonin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101759706B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109694377B (en) * | 2019-03-08 | 2020-03-31 | 重庆医药高等专科学校 | Synthesis method of Pulsatilla |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1306818A (en) * | 2000-02-04 | 2001-08-08 | 胡世卿 | Medicine for treating abacterial inflammation and its extraction method |
| CN1446818A (en) * | 2002-12-27 | 2003-10-08 | 成都和康药业有限责任公司 | Technique of preparing extract product of Radde Anemone Rhizome extract, and its application in preparing medication of treating cancer |
| CN101492489A (en) * | 2009-03-06 | 2009-07-29 | 吉林大学 | Method for extracting anemonin A and method of preparing lipid microsphere preparation |
-
2009
- 2009-10-20 CN CN2009102329900A patent/CN101759706B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1306818A (en) * | 2000-02-04 | 2001-08-08 | 胡世卿 | Medicine for treating abacterial inflammation and its extraction method |
| CN1446818A (en) * | 2002-12-27 | 2003-10-08 | 成都和康药业有限责任公司 | Technique of preparing extract product of Radde Anemone Rhizome extract, and its application in preparing medication of treating cancer |
| CN101492489A (en) * | 2009-03-06 | 2009-07-29 | 吉林大学 | Method for extracting anemonin A and method of preparing lipid microsphere preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101759706A (en) | 2010-06-30 |
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| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: CHONGQING HONOROAD ANIMAL NUTRITION CO., LTD. Free format text: FORMER OWNER: SUZHOU PAITENG BIOPHARMACEUTICAL TECHNOLOGY CO., LTD. Effective date: 20120326 |
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| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 215011 SUZHOU, JIANGSU PROVINCE TO: 401122 YUBEI, CHONGQING |
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| TR01 | Transfer of patent right |
Effective date of registration: 20120326 Address after: 401122 Chongqing City Economic Development Zone Park C40 block C building four layer Patentee after: CHONGQING HONOROAD ANIMAL HEALTH CO., LTD. Address before: Suzhou City, Jiangsu Province, 215011 Suzhou high tech Development Zone Sunshine Holiday Garden Building 63, No. 1412 Patentee before: Suzhou Paiteng Biopharmaceutical Technology Co., Ltd. |