CN1762398A - A kind of extracting method of ferula feruloides medicinal composition - Google Patents
A kind of extracting method of ferula feruloides medicinal composition Download PDFInfo
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Abstract
The present invention relates to a kind of extracting method of ferula feruloides medicinal composition, this method is to utilize supercritical carbon dioxide extraction method that the micromolecule composition in the Resina Ferulae is extracted, simultaneously by changing the supercritical carbon dioxide extraction condition, with nonpolar or low polar compound as terpenoids such as 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, with middle polarity or high polar compound as: 2,4-resacetophenone sesquiterpene derivative, 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone, diterpene coumarin is separated into the position of two different pharmaceutical usages, and then provides an easy method for the extraction separation of ferula feruloides medicinal effective site.This method is avoided using inflammable in a large number, explosive even deleterious organic solvent, and has simplified extraction step, has avoided poisonous organic solvent residual in the extract simultaneously, meets the isolating trend of Green Chemistry of present promotion.
Description
Technical field
The present invention relates to a kind of extracting method that utilizes supercritical carbon dioxide extraction method from medicinal plants Resina Ferulae among the people (Ferula ferlaeoidis (Sted.) Korov.), to extract Pharmaceutical composition.
Background technology
Resina Ferulae ferula narthex, fragrant Resina Ferulae, three nine-day periods after the winter solstice Resina Ferulae of claiming again among the people, its root of usefulness among the people or the oozy liquid of rhizome or resin-like thing treatment digestive system disease have effects such as dysentery relieving, removing food stagnancy, detoxifcation, antiinflammatory.
The Ferula plant has 150 kinds to be distributed in vast zone, the Central Asia to Mediterranean approximately, Ferula plant pharmaceutical usage comprises: spasmolytic, treatment asthma, removing food stagnancy, anticoagulation, antifertility, antioxidation etc., and all influential to digestion, blood circulation, nerve, immune system.
Existing studies show that contained 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene in the Resina Ferulae, and 2,4-resacetophenone or 2, chemical constituents such as the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
Pharmacological research proof 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene has antitussive action.2,4-resacetophenone sesquiterpene derivative particularly Dshamirone has inhibitory action to alpha-glucosidase, can control hyperglycemia phenomenon after meal, avoids type ii diabetes late complication shape, as: symptoms such as retinopathy, nephropathy occur.The Resina Ferulae diterpene coumarin has the tumor of inhibition and suppresses the HIV (human immunodeficiency virus) (Human Immunodeficiency Virus) effect.Other 2,4-resacetophenone or 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone have antioxidation, restraint of tyrosinase, inhibition NO release action.
US6623768 has reported and has utilized supercritical carbon dioxide extraction method to extract estrogen-like product Ferutinine from Ferulahermonis.WO2004087179 has reported and has utilized organic solvent to extract the Jaeskeanadiol derivant from multiple Resina Ferulae, and gets estrogen-like product Ferutinine through alkali soap hydrolysis, purification Jaeskeanadiol, p-Hydroxybenzoateization.US20040433083 has reported organic solvents such as utilizing ethanol, ethyl acetate and extracted the coumarin composition with anti-tumor activity from Ferulaasafoetida L.Do not find that at present the patent report utilizes supercritical carbon dioxide extraction method to extract 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene and 2 respectively from Resina Ferulae, 4-resacetophenone sesquiterpene derivative, 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and diterpene coumarin report.
The present invention finds in research Resina Ferulae chemical constituent leaching process: utilize supercritical carbon dioxide extraction method easily the micromolecule composition in the Resina Ferulae to be extracted, simultaneously by changing the supercritical carbon dioxide extraction condition, can be easily with nonpolar or low polar compound as terpenoids such as 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, with middle polarity or high polar compound as: 2,4-resacetophenone sesquiterpene derivative, 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone, diterpene coumarin is separated into the position of two different pharmaceutical usages, and then provides an easy method for the extraction separation of ferula feruloides medicinal effective site.
Utilize supercritical carbon dioxide extraction method to extract in the medicinal plants effective ingredient and not only can avoid using inflammable in a large number, explosive even deleterious organic solvent, and simplified extraction step, avoid poisonous organic solvent residual in the extract simultaneously, met the isolating trend of Green Chemistry of present promotion.
Summary of the invention
The purpose of this invention is to provide a kind of 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene and 2 of from Resina Ferulae, extracting respectively, 4-resacetophenone sesquiterpene derivative, 2, the method for the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.Utilize supercritical carbon dioxide extraction method easily the micromolecule composition in the Resina Ferulae to be extracted, simultaneously by changing the supercritical carbon dioxide extraction condition, can be easily with nonpolar or low polar compound as terpenoids such as 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, with middle polarity or high polar compound as: 2,4-resacetophenone sesquiterpene derivative, 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone, diterpene coumarin is separated into the position of two different pharmaceutical usages, and then provides an easy method for the extraction separation of ferula feruloides medicinal effective site.This method is avoided using inflammable in a large number, explosive even deleterious organic solvent, and has simplified extraction step, has avoided poisonous organic solvent residual in the extract simultaneously.
The extracting method of a kind of ferula feruloides medicinal composition of the present invention follows these steps to carry out:
A, the Resina Ferulae root is crushed to the powder that granularity is the 0.1-5 millimeter, join in the supercritical carbon dioxide extraction device, carry out the supercritical extraction first time with carbon dioxide, extraction conditions is: extracting pressure: 10-30Mpa, extraction temperature: 35-75 ℃, extraction time: 0.5-6 hour, separating pressure: 3.8-6Mpa, separation temperature: 25-50 ℃, after extraction finishes, the extract of collecting in the separator gets extract I, and wherein the extract I main component is a 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene;
B, residue slag reuse carbon dioxide and 1-15% organic carried agent ethanol or ethyl acetate or acetone or methane dioxide to carry out extracting the second time, extracting pressure: 20-50Mpa, extraction temperature: 35-75 ℃, extraction time: 0.5-6 hour, separating pressure: 3.8-10Mpa, separation temperature: 25-50 ℃, after extraction finishes, collect the extract in the separator, the used agent of carrying is removed in evaporation in case of necessity, obtains extract II, and wherein the extract II main component is 2,4-resacetophenone sesquiterpene derivative and 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
Utilize the extract of gained of the present invention to can be used as oral liquid, tablet, capsule, soft capsule and cosmetics, food additive use.
The specific embodiment:
Embodiment 1
Take by weighing Resina Ferulae root 330g, through pulverizing, join in the supercritical carbon dioxide extraction device, at first carry out the extraction first time with carbon dioxide, extracting pressure: 15Mpa, extraction temperature: 50 ℃, the extraction time: 3.5 hours, separating pressure: 4.0Mpa, separation temperature: 30 ℃, after extraction finishes, collect the extract in the separator, getting extract I after the drying is 13.9 grams, extraction ratio 4.2%, wherein the extract I main component is a 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, this extract I is after placing 7 days under the room temperature, filter, get the 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene crystal;
Then with remaining slag reuse carbon dioxide with carry agent ethanol (volume ratio 10: 1) and carry out extracting second time, extracting pressure: 25MPa, extraction temperature: 50 ℃, separating pressure: 4.5MPa, separation temperature: 30 ℃, extraction time: 4 hours, after extraction finishes, collect the extract in the separator, distilling under reduced pressure goes to get extract 18.7g behind the ethanol, yield is 5.7%, wherein the extract II main component is 2,4-resacetophenone sesquiterpene derivative and 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
Embodiment 2
Take by weighing Resina Ferulae root 350g, through pulverizing, join in the supercritical carbon dioxide extraction device, at first carry out the extraction first time with carbon dioxide, extracting pressure: 10Mpa, extraction temperature: 40 ℃, the extraction time: 3.5 hours, separating pressure: 3.0Mpa, separation temperature: 40 ℃, after extraction finishes, collect the extract in the separator, get extract 13.7 grams after the drying, extraction ratio 3.9%, wherein the extract I main component is a 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, this extract I is after placing 7 days under the room temperature, filter, get the 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene crystal;
Then with remaining slag reuse carbon dioxide with carry agent ethanol (volume ratio 100: 5) and carry out extracting second time, extracting pressure: 30MPa, extraction temperature: 40 ℃, separating pressure: 7.8MPa, separation temperature: 40 ℃, extraction time: 4 hours, after extraction finishes, collect the extract in the separator, distilling under reduced pressure goes to get extract 19.3g behind the ethanol, yield is 5.5%, wherein the extract II main component is 2,4-resacetophenone sesquiterpene derivative and 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
Embodiment 3
Take by weighing Resina Ferulae root 342g,, join in the supercritical carbon dioxide extraction device, at first carry out the extraction first time with carbon dioxide through pulverizing.Extracting pressure: 20MPa, extraction temperature: 45 ℃, extraction time: 4 hours, separating pressure: 4.0MPa, separation temperature: 30 ℃.After extraction finished, the extract in the collection separator got extract 15.3 grams after the drying, extraction ratio 4.4%, and wherein the extract I main component is a 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, this extract I is filtered after placing 7 days under the room temperature, gets the 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene crystal;
Then with remaining slag reuse carbon dioxide with carry agent acetone (volume ratio 100: 5) and carry out extracting second time, extracting pressure: 40MPa, extraction temperature: 45 ℃, separating pressure: 4.5MPa, separation temperature: 35 ℃, extraction time: 4 hours, after extraction finishes, collect the extract in the separator, distilling under reduced pressure goes to get extract 18.4g behind the acetone, yield is 5.3%, wherein the extract II main component is 2,4-resacetophenone sesquiterpene derivative and 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
Embodiment 4
Take by weighing Resina Ferulae root 347g, through pulverizing, join in the supercritical carbon dioxide extraction device, at first carry out first time extraction, extracting pressure: 15MPa, extraction temperature: 50 ℃, extraction time: 3.5 hours, separating pressure: 4.0MPa, separation temperature: 30 ℃ with carbon dioxide.After extraction finished, the extract in the collection separator got extract 14.1 grams after the drying, extraction ratio 4.0%, and wherein the extract I main component is a 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, this extract I is filtered after placing 7 days under the room temperature, gets the 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene crystal;
Then with remaining slag reuse carbon dioxide with carry agent ethyl acetate (volume ratio 10: 2) and carry out extracting second time, extracting pressure: 25MPa, extraction temperature: 50 ℃, separating pressure: 4.5MPa, separation temperature: 30 ℃, extraction time: 4 hours, after extraction finishes, collect the extract in the separator, distilling under reduced pressure goes to get extract 20.5g after the ethyl acetate, yield is 5.9%, wherein the extract II main component is 2,4-resacetophenone sesquiterpene derivative and 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
Embodiment 5
Take by weighing Resina Ferulae root 345g, through pulverizing, join in the supercritical carbon dioxide extraction device, at first carry out first time extraction, extracting pressure: 15MPa, extraction temperature: 50 ℃, extraction time: 3.5 hours, separating pressure: 4.0MPa, separation temperature: 30 ℃ with carbon dioxide.After extraction finished, the extract in the collection separator got extract 14.3 grams after the drying, extraction ratio 4.1%, and wherein the extract I main component is a 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene, this extract I is filtered after placing 7 days under the room temperature, gets the 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene crystal;
Then with remaining slag reuse carbon dioxide with carry agent methane dioxide (volume ratio 10: 1) and carry out extracting second time, extracting pressure: 25MPa, extraction temperature: 50 ℃, separating pressure: 4.5MPa, separation temperature: 30 ℃, extraction time: 4 hours, after extraction finishes, collect the extract in the separator, distilling under reduced pressure goes to get extract 17.2g after the ethyl acetate, yield is 5.0%, wherein extract II main component II is 2,4-resacetophenone sesquiterpene derivative and 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
Claims (1)
1, a kind of extracting method of ferula feruloides medicinal composition is characterized in that this extracting method follows these steps to carry out:
A, the Resina Ferulae root is crushed to the powder that granularity is the 0.1-5 millimeter, join in the supercritical carbon dioxide extraction device, carry out the supercritical extraction first time with carbon dioxide, extraction conditions is: extracting pressure: 10-30Mpa, extraction temperature: 35-75 ℃, extraction time: 0.5-6 hour, separating pressure: 3.8-6Mpa, separation temperature: 25-50 ℃, after extraction finishes, the extract of collecting in the separator gets extract I, and wherein the extract I main component is a 3,8-dimethyl-5-(.alpha.-hydroxyisopropyl)-.DELTA.9-octahydroazulene;
B, residue slag reuse carbon dioxide and 1-15% organic carried agent ethanol or ethyl acetate or acetone or methane dioxide to carry out extracting the second time, extracting pressure: 20-50Mpa, extraction temperature: 35-75 ℃, extraction time: 0.5-6 hour, separating pressure: 3.8-10Mpa, separation temperature: 25-50 ℃, after extraction finishes, collect the extract in the separator, the used agent of carrying is removed in evaporation, obtains extract II, and wherein the extract II main component is 2,4-resacetophenone sesquiterpene derivative, 2, the sesquiterpene derivative of 4-dihydroxyphenyl-1-propanone and Resina Ferulae diterpene coumarin.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2005101060710A CN100388924C (en) | 2005-09-27 | 2005-09-27 | Method for extracting ferula feruloides medicinal composition |
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| CNB2005101060710A CN100388924C (en) | 2005-09-27 | 2005-09-27 | Method for extracting ferula feruloides medicinal composition |
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| CN100388924C CN100388924C (en) | 2008-05-21 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102795969A (en) * | 2011-05-23 | 2012-11-28 | 石河子大学 | Natural sesquiterpene guaiol compound and medicinal application thereof |
| CN103113382A (en) * | 2013-01-22 | 2013-05-22 | 李国玉 | Group of sesquiterpenoid coumarin and sesquiterpenoid chromone compounds |
| CN103387582A (en) * | 2012-05-07 | 2013-11-13 | 复旦大学 | Coumarin natural product, and preparation method and application thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100651650B1 (en) * | 2000-10-12 | 2006-11-30 | 한국화학연구원 | Anti-cancer composition comprising sesquiterpene compounds isolated from ferulae resina |
| US6623768B1 (en) * | 2002-04-16 | 2003-09-23 | Yousry M. A. Naguib | Pharmaceutically active composition extracted from Ferula hermonis and process of its extraction |
| CN1233316C (en) * | 2003-05-20 | 2005-12-28 | 王彦丁 | Asafetida extract and its pharmaceutical use |
| CN1237962C (en) * | 2003-08-04 | 2006-01-25 | 王彦丁 | Pharmaceutical use of Resina-Ferulae extract |
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2005
- 2005-09-27 CN CNB2005101060710A patent/CN100388924C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102795969A (en) * | 2011-05-23 | 2012-11-28 | 石河子大学 | Natural sesquiterpene guaiol compound and medicinal application thereof |
| CN103387582A (en) * | 2012-05-07 | 2013-11-13 | 复旦大学 | Coumarin natural product, and preparation method and application thereof |
| CN103113382A (en) * | 2013-01-22 | 2013-05-22 | 李国玉 | Group of sesquiterpenoid coumarin and sesquiterpenoid chromone compounds |
| CN103113382B (en) * | 2013-01-22 | 2015-09-16 | 李国玉 | One group of diterpene coumarin, sesquiterpene chromone compounds |
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| CN100388924C (en) | 2008-05-21 |
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Granted publication date: 20080521 Termination date: 20120927 |