CN102850310A - Method for extracting and separating michelia lactone from michelia compressa - Google Patents
Method for extracting and separating michelia lactone from michelia compressa Download PDFInfo
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- CN102850310A CN102850310A CN2012103628329A CN201210362832A CN102850310A CN 102850310 A CN102850310 A CN 102850310A CN 2012103628329 A CN2012103628329 A CN 2012103628329A CN 201210362832 A CN201210362832 A CN 201210362832A CN 102850310 A CN102850310 A CN 102850310A
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- smile
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- lactone
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- michelia
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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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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention belongs to the field of natural pharmaceutical chemistry, which discloses a method for extracting and separating michelia lactone from michelia compressa. In the method, michelia compressa is taken as a raw material, crushed at 20 to 40 meshes and added into an extraction kettle; absolute methanol is taken as entrainer; supercritical CO2 extraction is adopted; extraction liquid is collected; methanol is recovered, so as to obtain extractive matter; sherwood oil is used for circumfluence to remove oil-soluble impurities; oil-soluble substance is dissolved through lower alcohol; active carbon is added into the oil-soluble substance to perform circumfluence destaining; destaining solution is recovered to proper volume; purification is performed through a prepared liquid phase ODSRP-C18 reversed-phase column; a mixed solution of methanol and water is used for elution; corresponding components are concentrated; and sherwood oil-acetone (2:1, V/V) is recrystallized, so that michelia lactone products are obtained.
Description
Technical field
The invention belongs to the Natural Medicine Chemistry field, particularly relate to a kind of from have a smile on one's face in Taiwan, the extraction and separate the with a smile method of lactone.
Background technology
Lactone (Micheliolide) belongs to the sesquiterpene lactones compounds with a smile, is guainane type sesquiterpene lactones compounds.Molecular formula is C
15H
20O
3, molecular weight is 248.32, is colourless crystallization, mp.142-145 ℃.Magnoliacea plant is yellow blue again
Michelia champacaL. root skin, Taiwan are with a smile
Michelia compressa(Maxim.) in the root skin of Sarg. distribution is arranged all.Have report to find that lactone almost is equal in the effect with parithenolide aspect the treatment leukemia with a smile, and its to normal cell without obvious lethal effect.Research finds that with a smile lactone and derivative thereof can be used for treating following cancer: leukemia, mammary cancer, prostate cancer, large bowel cancer or lung cancer, other have report with a smile lactone also have the purposes of Hepatoma therapy, esophagus cancer, cancer of the stomach, enteron aisle cancer, kidney, oral carcinoma, He Jiejin lymphatic cancer, carcinoma of the pancreas, carcinoma of the colon and rectum etc.
Existing preparation with a smile the method for lactone mainly by chemosynthesis, Chinese patent application numbers 201010153685.5 discloses a kind of with a smile preparation method of lactone, take parithenolide as raw material, in suitable organic solvent, prepare with a smile lactone under acid catalyst, productive rate reaches more than 60%.The method by product is more, and is not easily separated, and circulation ratio is relatively poor, is not suitable for suitability for industrialized production.
Summary of the invention
The object of the invention is to solve shortcomings and deficiencies of the prior art, provide a kind of from have a smile on one's face in Taiwan, the extraction to separate the with a smile method of lactone.
To achieve these goals, technical scheme of the present invention is as follows:
A kind of extraction from have a smile on one's face in Taiwan separated the with a smile method of lactone, it is characterized in that may further comprise the steps: be with a smile raw material take Taiwan, pulverize the 20-40 order, in the adding extraction kettle, take anhydrous methanol as entrainment agent, adopt supercritical CO
2Extraction liquid is collected in extraction, reclaims methyl alcohol, get extract, refluxing with sherwood oil removes oil-soluble impurities, again with degreasing thing low-carbon alcohol thermosol, add the gac reflux decolour, destainer reclaims solvent to an amount of volume, carries out purifying through preparation liquid phase ODS RP-C18 reversed-phase column, carries out wash-out with the mixing solutions of first alcohol and water, concentrated corresponding component, sherwood oil-acetone (2:1, V/V) recrystallization must be had a smile on one's face lactone products.
Described supercritical CO
2Extraction conditions is: extraction temperature is 45-60 ℃, and extracting pressure is 23-34MPa, and separating still I temperature is 40-50 ℃, and pressure is 8-10MPa, and separating still II temperature is 35-40 ℃, and pressure is 4-6MPa, and extraction time is 2-6h.
Described petroleum ether degreasing, the sherwood oil reflux degreasing of 2-5 times of extract volume of adding 1-3 time, centrifugal, separate solid-liquid, get the degreasing thing.
Described low-carbon alcohol is C1-C4 alcohol, preferred alcohol, methyl alcohol or Virahol.
The mixing solutions of described first alcohol and water refers to that the methyl alcohol volume percent is 83%, and the volume percent of water is 17% mixing solutions.
Advantage of the present invention is: method adopts supercritical CO
2Extraction, extraction efficiency is high, energy consumption is low, environmental protection; Go out highly purified crystal with the direct separation and purification of preparation liquid phase, for large-scale industrial production provides possibility, greatly saved disengaging time, improved separation rate.
Embodiment:
Further specify the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to the following example.
Embodiment 1:
Pulverizing medicinal materials 40 orders are had a smile on one's face in Taiwan, get the 10kg raw material and add supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 45 ℃, and extracting pressure is 34MPa, and separating still I temperature is 40 ℃, and pressure is 10MPa, and separating still II temperature is 38 ℃, and pressure is 4MPa.Pass into CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 22L/h flow, and carry anhydrous methanol 3L/h secretly, dynamic extraction 3.5h, collect extraction liquid, reclaim methyl alcohol, the sherwood oil that adds 2 times of extract volumes, heating and refluxing extraction 1 time, the centrifugal liquid of removing, again with degreasing thing methyl alcohol heating for dissolving, add the gac reflux decolour, destainer reclaims solvent to 1/3 of original volume, is mixed with the solution of 20mg/ml concentration with the methyl alcohol ultrasonic dissolution, nylon membrane with 0.45 μ m filters filter, with the separation and purification of preparative high-performance liquid chromatographic instrument, methanol-water (83:17) Gradient elution is after collection response component rotary evaporation is concentrated, obtain purity and be 95.3% with a smile in crystalline esters, again through sherwood oil-acetone (2:1, V/V) recrystallization 3 times, get purity and be 98.7% with a smile lactone products.
Embodiment 2:
Pulverizing medicinal materials 20 orders are had a smile on one's face in Taiwan, get the 10kg raw material and add supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 58 ℃, and extracting pressure is 31MPa, and separating still I temperature is 50 ℃, and pressure is 8MPa, and separating still II temperature is 40 ℃, and pressure is 6MPa.Pass into CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 22L/h flow, and carry anhydrous methanol 3L/h secretly, dynamic extraction 4h, collect extraction liquid, reclaim methyl alcohol, the sherwood oil that adds 3 times of extract volumes, heating and refluxing extraction 3 times, the centrifugal liquid of removing, again with degreasing thing Virahol heating for dissolving, add the gac reflux decolour, destainer reclaims solvent to 1/3 of original volume, is mixed with the solution of 20mg/ml concentration with the methyl alcohol ultrasonic dissolution, nylon membrane with 0.45 μ m filters filter, with the separation and purification of preparative high-performance liquid chromatographic instrument, methanol-water (83:17) Gradient elution is after collection response component rotary evaporation is concentrated, obtain purity and be 95.6% with a smile in crystalline esters, again through sherwood oil-acetone (2:1, V/V) recrystallization 2 times, get purity and be 99.2% with a smile lactone products.
Embodiment 3:
Pulverizing medicinal materials 40 orders are had a smile on one's face in Taiwan, get the 10kg raw material and add supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 46 ℃, and extracting pressure is 24MPa, and separating still I temperature is 42 ℃, and pressure is 9MPa, and separating still II temperature is 36 ℃, and pressure is 5MPa.Pass into CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 22L/h flow, and carry anhydrous methanol 3L/h secretly, dynamic extraction 5h, collect extraction liquid, reclaim methyl alcohol, the sherwood oil that adds 5 times of extract volumes, heating and refluxing extraction 2 times, the centrifugal liquid of removing, again with degreasing thing ethanol heating for dissolving, add the gac reflux decolour, destainer reclaims solvent to 1/3 of original volume, is mixed with the solution of 20mg/ml concentration with the methyl alcohol ultrasonic dissolution, nylon membrane with 0.45 μ m filters filter, with the separation and purification of preparative high-performance liquid chromatographic instrument, methanol-water (83:17) Gradient elution is after collection response component rotary evaporation is concentrated, obtain purity and be 96.1% with a smile in crystalline esters, again through sherwood oil-acetone (2:1, V/V) recrystallization 3 times, get purity and be 98.5% with a smile lactone products.
Embodiment 4:
Pulverizing medicinal materials 40 orders are had a smile on one's face in Taiwan, get the 10kg raw material and add supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 53 ℃, and extracting pressure is 27MPa, and separating still I temperature is 48 ℃, and pressure is 8MPa, and separating still II temperature is 35 ℃, and pressure is 4MPa.Pass into CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 22L/h flow, and carry anhydrous methanol 3L/h secretly, dynamic extraction 3h, collect extraction liquid, reclaim methyl alcohol, the sherwood oil that adds 4 times of extract volumes, heating and refluxing extraction 3 times, the centrifugal liquid of removing, again with degreasing thing Virahol heating for dissolving, add the gac reflux decolour, destainer reclaims solvent to 1/3 of original volume, is mixed with the solution of 20mg/ml concentration with the methyl alcohol ultrasonic dissolution, nylon membrane with 0.45 μ m filters filter, with the separation and purification of preparative high-performance liquid chromatographic instrument, methanol-water (83:17) Gradient elution is after collection response component rotary evaporation is concentrated, obtain purity and be 95.8% with a smile in crystalline esters, again through sherwood oil-acetone (2:1, V/V) recrystallization 2 times, get purity and be 98.2% with a smile lactone products.
Embodiment 5:
Pulverizing medicinal materials 40 orders are had a smile on one's face in Taiwan, get the 10kg raw material and add 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 43 ℃, and pressure is 10MPa, and separating still II temperature is 38 ℃, and pressure is 6MPa.Pass into CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 22L/h flow, and carry anhydrous methanol 3L/h secretly, dynamic extraction 6h, collect extraction liquid, reclaim methyl alcohol, the sherwood oil that adds 2 times of extract volumes, heating and refluxing extraction 2 times, the centrifugal liquid of removing, again with degreasing thing ethanol heating for dissolving, add the gac reflux decolour, destainer reclaims solvent to 1/3 of original volume, is mixed with the solution of 20mg/ml concentration with the methyl alcohol ultrasonic dissolution, nylon membrane with 0.45 μ m filters filter, with the separation and purification of preparative high-performance liquid chromatographic instrument, methanol-water (83:17) Gradient elution is after collection response component rotary evaporation is concentrated, obtain purity and be 95.5% with a smile in crystalline esters, again through sherwood oil-acetone (2:1, V/V) recrystallization 4 times, get purity and be 98.6% with a smile lactone products.
Embodiment 6:
Pulverizing medicinal materials 20 orders are had a smile on one's face in Taiwan, get the 10kg raw material and add supercritical CO
2In the extraction kettle, opening device, setup parameter: extraction temperature is 56 ℃, and extracting pressure is 33MPa, and separating still I temperature is 46 ℃, and pressure is 9MPa, and separating still II temperature is 36 ℃, and pressure is 5MPa.Pass into CO
2Fluid, reach above-mentioned parameter after, with CO
2The extraction of liquid 22L/h flow, and carry anhydrous methanol 3L/h secretly, dynamic extraction 2h, collect extraction liquid, reclaim methyl alcohol, the sherwood oil that adds 5 times of extract volumes, heating and refluxing extraction 1 time, the centrifugal liquid of removing, again with degreasing thing methyl alcohol heating for dissolving, add the gac reflux decolour, destainer reclaims solvent to 1/3 of original volume, is mixed with the solution of 20mg/ml concentration with the methyl alcohol ultrasonic dissolution, nylon membrane with 0.45 μ m filters filter, with the separation and purification of preparative high-performance liquid chromatographic instrument, methanol-water (83:17) Gradient elution is after collection response component rotary evaporation is concentrated, obtaining purity is the with a smile interior crystalline esters of 96.3 %, again through sherwood oil-acetone (2:1, V/V) recrystallization 5 times, get purity and be 99.5% with a smile lactone products.
Claims (5)
1. one kind is extracted the with a smile method of lactone of separation from have a smile on one's face in Taiwan, it is characterized in that may further comprise the steps: be with a smile raw material take Taiwan, pulverize the 20-40 order, in the adding extraction kettle, take anhydrous methanol as entrainment agent, adopt supercritical CO
2Extraction liquid is collected in extraction, reclaims methyl alcohol, get extract, refluxing with sherwood oil removes oil-soluble impurities, again with degreasing thing low-carbon alcohol thermosol, add the gac reflux decolour, destainer reclaims solvent to an amount of volume, carries out purifying through preparation liquid phase ODS RP-C18 reversed-phase column, carries out wash-out with the mixing solutions of first alcohol and water, concentrated corresponding component, sherwood oil-acetone (2:1, V/V) recrystallization must be had a smile on one's face lactone products.
2. the described method of lactone of having a smile on one's face of extracting with a smile from Taiwan according to claim 1 is characterized in that described supercritical CO
2Extraction conditions is: extraction temperature is 45-60 ℃, and extracting pressure is 23-34MPa, and separating still I temperature is 40-50 ℃, and pressure is 8-10MPa, and separating still II temperature is 35-40 ℃, and pressure is 4-6MPa, and extraction time is 2-6h.
3. describedly according to claim 1 extract the with a smile method of lactone from Taiwan with a smile, it is characterized in that described petroleum ether degreasing, add sherwood oil reflux degreasing 1-3 time of 2-5 times of extract volume, centrifugal, the separation solid-liquid gets the degreasing thing.
4. describedly according to claim 1 extract the with a smile method of lactone from Taiwan with a smile, it is characterized in that described low-carbon alcohol is that C1-C4 is pure, preferred alcohol, methyl alcohol or Virahol.
5. the described method of lactone of having a smile on one's face of extracting with a smile from Taiwan according to claim 1 is characterized in that the mixing solutions of described first alcohol and water refers to that the methyl alcohol volume percent is 83%, and the volume percent of water is 17% mixing solutions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012103628329A CN102850310A (en) | 2012-09-26 | 2012-09-26 | Method for extracting and separating michelia lactone from michelia compressa |
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|---|---|---|---|
| CN2012103628329A CN102850310A (en) | 2012-09-26 | 2012-09-26 | Method for extracting and separating michelia lactone from michelia compressa |
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| CN102850310A true CN102850310A (en) | 2013-01-02 |
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| CN2012103628329A Pending CN102850310A (en) | 2012-09-26 | 2012-09-26 | Method for extracting and separating michelia lactone from michelia compressa |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104211669A (en) * | 2013-06-05 | 2014-12-17 | 天津尚德药缘科技有限公司 | Micheliolide derivative and preparation method and use thereof |
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2012
- 2012-09-26 CN CN2012103628329A patent/CN102850310A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104211669A (en) * | 2013-06-05 | 2014-12-17 | 天津尚德药缘科技有限公司 | Micheliolide derivative and preparation method and use thereof |
| CN104211669B (en) * | 2013-06-05 | 2018-01-19 | 天津尚德药缘科技股份有限公司 | Lactone derivatives with a smile, and its production and use |
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Application publication date: 20130102 |