CN102329352A - Method for extracting vernodalin from vernonia anthelmintica - Google Patents
Method for extracting vernodalin from vernonia anthelmintica Download PDFInfo
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- CN102329352A CN102329352A CN201110210040A CN201110210040A CN102329352A CN 102329352 A CN102329352 A CN 102329352A CN 201110210040 A CN201110210040 A CN 201110210040A CN 201110210040 A CN201110210040 A CN 201110210040A CN 102329352 A CN102329352 A CN 102329352A
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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
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- 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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Abstract
The invention belongs to the chemical field of natural medicines, and discloses a method for extracting vernodalin from vernonia anthelmintica. The method comprises the steps of: by taking vernonia anthelmintica as a raw material, crushing and sieving with sieves of 20-80 meshes; adding the vernonia anthelmintica in an extraction kettle, and collecting an extract liquid by taking absolute methanol as an entrainer and adopting supercritical CO2 extraction; recovering methanol to obtain extracts; degreasing through petroleum ether; then separating the extracts by taking n-hexane-ethyl acetate-methanol-water as a solvent system and adopting a high-speed countercurrent chromatography; and depressurizing and concentrating an eluate to obtain vernodalin. The method disclosed by the invention adopts the supercritical CO2 extraction and a high-speed countercurrent chromatographic separation technology, and is highly efficient, environment-friendly and suitable for industrial production.
Description
Technical field
The invention belongs to the Natural Medicine Chemistry field, particularly relate to a kind of method of from stem of Anthelmintic Ironweed, extracting vernodalin.
Background technology
Vernodalin (Vernodalin) is a sesquiterpenoid, chemical name 2-Propenoic acid, and 2-(hydroxymethyl)-, 5a-ethenyldecahy-dro-3; 9-bis (methylene)-2,8-dioxo-2H-furo [2,3-f] benzopyran-4ylester, [3aR-(3a α; 4a α, 5a α, 9a α; 9b β)-, molecular formula C19H20O7, molecular weight 360.35.The high purity vernodalin is a colorless oil, and (α) 24D+125 ° (C=1.35, chloroform) is dissolved in methyl alcohol, ethanol, acetone etc., water insoluble, sherwood oil etc.Vernodalin has antibiotic desinsection, antimalarial, anti-tumor activity effect.
Stem of Anthelmintic Ironweed is India's mountain fennel, Ai Teri pulling force again for to be the fruit of dicotyledons medicine feverfew stem of Anthelmintic Ironweed.The stem of Anthelmintic Ironweed beginning is stated from " Chinese Plants will ", and fruit bitter, cool in nature has heat clearing and inflammation relieving, and is promoting blood circulation and removing blood stasis, and parasiticidal function is used to treat skin spot, expelling parasite etc.
Mostly the existing disclosed vernodalin method of from stem of Anthelmintic Ironweed, extracting is scientific research, generally adopts alcohol extracting, degreasing and steps such as silica gel column chromatography separates.There are technological deficiencies such as sample loss is serious, poor reproducibility in silica gel column chromatography, in the suitability for industrialized production vernodalin, is difficult to realize.
Summary of the invention
The objective of the invention is to solve the deficiency and the defective of prior art, a kind of method of from stem of Anthelmintic Ironweed, extracting vernodalin is provided.
To achieve these goals, technical scheme of the present invention is following:
A kind of method of from stem of Anthelmintic Ironweed, extracting vernodalin is characterized in that may further comprise the steps: being raw material with the stem of Anthelmintic Ironweed, pulverizing the 20-80 order, add in the extraction kettle, is entrainment agent with the anhydrous methanol, adopts supercritical CO
2Extraction liquid is collected in extraction, reclaims methyl alcohol, gets extract, and petroleum ether degreasing is a solvent systems with normal hexane-ETHYLE ACETATE-methyl alcohol-water again, adopts high speed adverse current chromatogram separating and extracting thing, and the flow point concentrating under reduced pressure promptly gets vernodalin.
Said supercritical CO
2Extraction conditions is: extraction temperature is 60-65 ℃, and extracting pressure is 18-23MPa, and separating still I temperature is 50-60 ℃, and pressure is 7-9MPa, and separating still II temperature is 45-50 ℃, and pressure is 5-6MPa.Supercritical CO among the present invention
2The extraction time was controlled at 2-3 hour, CO
2Flow control is at 20-30L/h.
Described normal hexane-ETHYLE ACETATE-methyl alcohol-water solvent system ratio is 4: (6-7): (5-6): 5.During high speed adverse current chromatogram separating and extracting thing, being to be stationary phase mutually on the solution system, is moving phase down mutually, and following phased soln extract, equipment rotating speed are controlled at 700-1200r/min, and flow rate of mobile phase is 1-3ml/min.
Advantage of the present invention is: method adopts supercritical CO
2Extraction, extraction efficiency is high, low, the environmental protection of energy consumption; Method adopts high speed adverse current chromatogram to separate vernodalin, the loss of sepn process product-free, and preparation cycle is short, has overcome that sample extremely adsorbs in traditional silica gel column separation process, technology is loaded down with trivial details, the technological deficiency of poor reproducibility.
To combine embodiment to further specify the present invention below, but the scope that the present invention requires to protect is not limited to the following example.
Embodiment
Embodiment 1:
Stem of Anthelmintic Ironweed pulverizing medicinal materials 80 orders are got the 1000g raw material and are added supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 60 ℃, and extracting pressure is 23MPa, and separating still I temperature is 60 ℃, and pressure is 9MPa, and separating still II temperature is 45 ℃, and pressure is 5MPa.Feed CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 20L/h flow, and carry anhydrous methanol 300ml/h secretly, dynamic extraction 3h collects extraction liquid, reclaims methyl alcohol, and petroleum ether 3 times gets the 25g extract.Get normal hexane, ETHYLE ACETATE, methyl alcohol, water, for 4:7:5:5 mixes, get and inject the phase that fixes in the chromatotube mutually in proportion, open high-speed counter-current chromatograph; The adjusting rotating speed is 900r/min, pumps into down and does moving phase mutually, and flow rate regulation is 2ml/min, after the balance; Inject moving phase dissolved extract, the vernodalin flow point is collected in the UV-detector monitoring, merges the flow point concentrating under reduced pressure; Get the colourless liquid vernodalin, performance liquid detects, content 98.1%, yield 84.1%.
Embodiment 2:
Stem of Anthelmintic Ironweed pulverizing medicinal materials 20 orders are got the 1000g raw material and are added supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 65 ℃, and extracting pressure is 18MPa, and separating still I temperature is 50 ℃, and pressure is 7MPa, and separating still II temperature is 50 ℃, and pressure is 6MPa.Feed CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 25L/h flow, and carry anhydrous methanol 400ml/h secretly, dynamic extraction 2h collects extraction liquid, reclaims methyl alcohol, and petroleum ether 2 times gets the 22g extract.Get normal hexane, ETHYLE ACETATE, methyl alcohol, water, for 4:6:5:5 mixes, get and inject the phase that fixes in the chromatotube mutually in proportion, open high-speed counter-current chromatograph;, the adjusting rotating speed is 800r/min, flow rate of mobile phase is adjusted to 3ml/min, injects moving phase dissolved extract after the balance; The vernodalin flow point is collected in the UV-detector monitoring, merges the flow point concentrating under reduced pressure, gets the colourless liquid vernodalin; Performance liquid detects, content 97.5%, yield 86.2%.
Embodiment 3:
Stem of Anthelmintic Ironweed pulverizing medicinal materials 60 orders are got the 1000g raw material and are added supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 60 ℃, and extracting pressure is 20MPa, and separating still I temperature is 60 ℃, and pressure is 8MPa, and separating still II temperature is 45 ℃, and pressure is 5MPa.Feed CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 22L/h flow, and carry anhydrous methanol 400ml/h secretly, dynamic extraction 3h collects extraction liquid, reclaims methyl alcohol, and petroleum ether 3 times gets the 26g extract.Get normal hexane, ETHYLE ACETATE, methyl alcohol, water, for 4:7:6:5 mixes, get and inject the phase that fixes in the chromatotube mutually in proportion, open high-speed counter-current chromatograph; The adjusting rotating speed is 700r/min, and flow rate of mobile phase is adjusted to 1ml/min, injects moving phase dissolved extract after the balance, the UV-detector monitoring; Collect the vernodalin flow point, merge the flow point concentrating under reduced pressure, get the colourless liquid vernodalin; Performance liquid detects, content 98.5%, yield 80.1%.
Embodiment 4:
Stem of Anthelmintic Ironweed pulverizing medicinal materials 60 orders are got the 2000g raw material and are added supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 60 ℃, and extracting pressure is 20MPa, and separating still I temperature is 60 ℃, and pressure is 8MPa, and separating still II temperature is 45 ℃, and pressure is 5MPa.Feed CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 25L/h flow, and carry anhydrous methanol 600ml/h secretly, dynamic extraction 3h collects extraction liquid, reclaims methyl alcohol, and petroleum ether 3 times gets the 49g extract.Get normal hexane, ETHYLE ACETATE, methyl alcohol, water, for 4:6:6:5 mixes, get and inject the phase that fixes in the chromatotube mutually in proportion, open high-speed counter-current chromatograph; The adjusting rotating speed is 800r/min, and flow rate of mobile phase is adjusted to 2ml/min, injects moving phase dissolved extract after the balance, the UV-detector monitoring; Collect the vernodalin flow point, merge the flow point concentrating under reduced pressure, get the colourless liquid vernodalin; Performance liquid detects, content 98.3%, yield 84.2%.
Embodiment 5:
Stem of Anthelmintic Ironweed pulverizing medicinal materials 60 orders are got the 4g raw material and are added supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 60 ℃, and extracting pressure is 18MPa, and separating still I temperature is 60 ℃, and pressure is 9MPa, and separating still II temperature is 45 ℃, and pressure is 5MPa.Feed CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 25L/h flow, and carry anhydrous methanol 1000ml/h secretly, dynamic extraction 3h collects extraction liquid, reclaims methyl alcohol, and petroleum ether 3 times gets the 94g extract.Get normal hexane, ETHYLE ACETATE, methyl alcohol, water, for 4:7:6:5 mixes, get and inject the phase that fixes in the chromatotube mutually in proportion, open high-speed counter-current chromatograph; The adjusting rotating speed is 800r/min, and flow rate of mobile phase is adjusted to 31ml/min, injects moving phase dissolved extract after the balance, the UV-detector monitoring; Collect the vernodalin flow point, merge the flow point concentrating under reduced pressure, get the colourless liquid vernodalin; Performance liquid detects, content 97.9%, yield 82.3%.
Claims (3)
1. method of from stem of Anthelmintic Ironweed, extracting vernodalin, it is characterized in that may further comprise the steps: being raw material with the stem of Anthelmintic Ironweed, pulverizing the 20-80 order, add in the extraction kettle, is entrainment agent with the anhydrous methanol, adopts supercritical CO
2Extraction liquid is collected in extraction, reclaims methyl alcohol, gets extract, and petroleum ether degreasing is a solvent systems with normal hexane-ETHYLE ACETATE-methyl alcohol-water again, adopts high speed adverse current chromatogram separating and extracting thing, and the flow point concentrating under reduced pressure promptly gets vernodalin.
2. according to the said method of from stem of Anthelmintic Ironweed, extracting vernodalin of claim 1, it is characterized in that said supercritical CO
2Extraction conditions is: extraction temperature is 60-65 ℃, and extracting pressure is 18-23MPa, and separating still I temperature is 50-60 ℃, and pressure is 7-9MPa, and separating still II temperature is 45-50 ℃, and pressure is 5-6MPa.
3. according to the said method of from stem of Anthelmintic Ironweed, extracting vernodalin of claim 1, it is characterized in that described normal hexane-ETHYLE ACETATE-methyl alcohol-water solvent system ratio is 4: (6-7): (5-6): 5.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201110210040A CN102329352A (en) | 2011-07-26 | 2011-07-26 | Method for extracting vernodalin from vernonia anthelmintica |
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| CN201110210040A CN102329352A (en) | 2011-07-26 | 2011-07-26 | Method for extracting vernodalin from vernonia anthelmintica |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103798145A (en) * | 2014-02-28 | 2014-05-21 | 钦州市林业科学研究所 | Culture medium for tissue culture of vernonia amygdalina del. |
| CN104186572A (en) * | 2014-08-18 | 2014-12-10 | 中山市品汇创新专利技术开发有限公司 | Sustained-release calamus electric heating liquid mosquito-repellent incense and preparation method thereof |
| CN104206442A (en) * | 2014-08-18 | 2014-12-17 | 中山市品汇创新专利技术开发有限公司 | Vernonia-anthelmintica mosquito-repellent incense improving sleep quality and preparation method thereof |
| CN106083882A (en) * | 2016-06-04 | 2016-11-09 | 中国科学院新疆理化技术研究所 | Sesquiterpene dimers compounds in Caulis Vernoniae andersonii and preparation method and purposes |
| CN109010201A (en) * | 2018-10-30 | 2018-12-18 | 嘉文丽（福建）化妆品有限公司 | A kind of preparation method and application of almond ringdove chrysanthemum saponin(e |
| CN113180061A (en) * | 2021-05-24 | 2021-07-30 | 西昌市农业农村局 | Application of plant vernonia galamensis essential oil in preventing and treating red imported fire ant |
| CN114350527A (en) * | 2022-01-17 | 2022-04-15 | 中国科学院新疆理化技术研究所 | Separation and purification method of endophytic fungi in overground part tissue of Vernonia anthelmintica and application of endophytic fungi |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06192265A (en) * | 1992-12-25 | 1994-07-12 | Snow Brand Milk Prod Co Ltd | 4,15-dihydrovernodalin |
| US20020155184A1 (en) * | 2001-01-24 | 2002-10-24 | Jackson State University | Phytochemotherapy for cancer |
-
2011
- 2011-07-26 CN CN201110210040A patent/CN102329352A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06192265A (en) * | 1992-12-25 | 1994-07-12 | Snow Brand Milk Prod Co Ltd | 4,15-dihydrovernodalin |
| US20020155184A1 (en) * | 2001-01-24 | 2002-10-24 | Jackson State University | Phytochemotherapy for cancer |
Non-Patent Citations (3)
| Title |
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| IRAJ GANJIAN,等: "Insect antifeedant elemanolide lactones from vernonia amygdalina", 《PHYTOCHEMISTRY》 * |
| 吴剑飞，等: "驱虫斑鸠菊化学成分的研究", 《化学学报》 * |
| 王帅斌: "高速逆流色谱分离益智中诺卡酮香味物质的研究", 《北京工商大学硕士学位论文》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103798145A (en) * | 2014-02-28 | 2014-05-21 | 钦州市林业科学研究所 | Culture medium for tissue culture of vernonia amygdalina del. |
| CN104186572A (en) * | 2014-08-18 | 2014-12-10 | 中山市品汇创新专利技术开发有限公司 | Sustained-release calamus electric heating liquid mosquito-repellent incense and preparation method thereof |
| CN104206442A (en) * | 2014-08-18 | 2014-12-17 | 中山市品汇创新专利技术开发有限公司 | Vernonia-anthelmintica mosquito-repellent incense improving sleep quality and preparation method thereof |
| CN106083882A (en) * | 2016-06-04 | 2016-11-09 | 中国科学院新疆理化技术研究所 | Sesquiterpene dimers compounds in Caulis Vernoniae andersonii and preparation method and purposes |
| CN109010201A (en) * | 2018-10-30 | 2018-12-18 | 嘉文丽（福建）化妆品有限公司 | A kind of preparation method and application of almond ringdove chrysanthemum saponin(e |
| CN113180061A (en) * | 2021-05-24 | 2021-07-30 | 西昌市农业农村局 | Application of plant vernonia galamensis essential oil in preventing and treating red imported fire ant |
| CN114350527A (en) * | 2022-01-17 | 2022-04-15 | 中国科学院新疆理化技术研究所 | Separation and purification method of endophytic fungi in overground part tissue of Vernonia anthelmintica and application of endophytic fungi |
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Application publication date: 20120125 |