CN103980237A - Method for separating and extracting ligustilide from radices levistici - Google Patents
Method for separating and extracting ligustilide from radices levistici Download PDFInfo
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- CN103980237A CN103980237A CN201410218763.3A CN201410218763A CN103980237A CN 103980237 A CN103980237 A CN 103980237A CN 201410218763 A CN201410218763 A CN 201410218763A CN 103980237 A CN103980237 A CN 103980237A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
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Abstract
The invention provides a method for separating and extracting ligustilide from radices levistici. The method comprises the following steps: by taking dry radices levistici as a raw material, soaking with petroleum ether, conducting ultrasonic extraction, filtering and concentration, separating through a silica gel column, thus obtaining high-purity ligustilide. The method is low in the price of raw materials, simple to operate, and low in environment pollution. The purity of the ligustilide obtained by adopting the method is greater than 98%, the ligustilide can be used as a chemical reference substance, and is used for quality control on angelica sinensis medical materials and preparations thereof.
Description
Technical field
The present invention relates to the separating and extracting method of medicinal material effective constituent, specifically a kind of from Root of Garden Lovage the method for separation and Extraction Z-ligustilide.
Technical background
Ligustilide (Z-ligustilide) is the main effective constituent in traditional Chinese medicine Radix Angelicae Sinensis, Ligusticum wallichii, and its structural formula is as follows.
Ligustilide has spasmolysis, the cholinolytic such as relieving cough and asthma is active.It has stronger pharmacological action to cardio-cerebrovascular, the recycle system and immunity system etc., is the quality control index of Radix Angelicae Sinensis medicinal material and several formulations.At present existing patent report the preparation method of ligustilide from rhizome, method used is as follows:
Patent CN101210003B discloses the mixing medicinal powder of Radix Angelicae Sinensis and Ligusticum wallichii through supercritical CO
2fluid extraction obtains the extract containing Ligustilide, then through silicagel column wash-out, obtains the Ligustilide chemical reference substance that purity is greater than 99%.Patent CN102260232A discloses Radix Angelicae Sinensis medicinal material has been extracted with petroleum ether solution soak at room temperature, then with high performance liquid phase preparation, uses appropriate extracted with diethyl ether after the methanol aqueous solution that contains Ligustilide is diluted to lower concentration, obtains the Ligustilide that purity is greater than 98%.Visible, above-mentioned two kinds of methods need adopt supercritical CO
2extraction or high performance liquid phase preparation, method is loaded down with trivial details, and the raw material using is Radix Angelicae Sinensis or Ligusticum wallichii, and price is more expensive, and preparation cost is higher.
The preparation > > (herbal medicine of Ligustilide reference substance in document < < Ligusticum wallichii, 2006,37 (1): 64-65) take Ligusticum wallichii first extracts volatile oil as raw material, then by silica gel column chromatography, obtain the Z-ligustilide that purity is greater than 98%, this method complex process, and cost of material is more expensive; Document < < Ligustilide reference substance extracts research > > (Liaoning University of TCM's journal with stability, 2008,10 (5): 162-163) take Jehol Ligusticum Rhizome as raw material, adopt chloroform extraction, and obtain by the silicagel column separation and purification of chloroform wash-out the Z-ligustilide that purity is greater than 98%, raw material and reagent that this method is used are more expensive, and production cost is higher.
In addition, patent CN102295629A discloses under vacuum state, and the heating of Radix Angelicae Sinensis oil or Rhizoma Chuanxiong oil is carried out to vacuum fractionation, collects the cut of 100～110 ℃, then carries out molecular distillation, obtains purity and be 93.2～98.8% Ligustilide; Patent CN101088996A discloses Chinese Angelica Root sherwood oil refluxing extraction, then through medium pressure liguid chromatograph, prepares more than 95% Z-ligustilide of purity; It is raw material that patent CN100351247C be take the thick oil of Z-ligustilide, prepares purity be greater than 90% Ligustilide with the separation of silica gel reduced pressure chromatography method; Patent CN100391953C discloses Radix Angelicae Sinensis pulverizing medicinal materials and in high-shear instrument, has sheared extraction volatile oil, then adopts silica gel column chromatography method separating for several times, purifying, obtains purity and reaches more than 90% Ligustilide.The Z-ligustilide purity that aforesaid method obtains is more than 90%, but do not reach 98%, can not use as the reference substance of assay.
Summary of the invention
The object of the present invention is to provide a kind of from Root of Garden Lovage the method for separation and Extraction Z-ligustilide, the method is simple to operate, cost of material is lower, the purity of Z-ligustilide, more than 98%, can be used as chemical reference substance.
Provided by the invention a kind of from Root of Garden Lovage the method for separation and Extraction Z-ligustilide, comprise the steps:
Step 1: get dry Root of Garden Lovage and pulverize, adding liquid-solid ratio is the sherwood oil of 5～10ml ∕ g, soak at room temperature 1～5h, supersound extraction 1～5 time is extracted 0.5～2h at every turn, and gained extracting solution is merged, and filters, and concentrating under reduced pressure extracting solution obtains paste;
Step 2: the paste to step 1 gained is crossed silicagel column, to add the mixed solution wash-out of 0.5～5 part of ether or ethyl acetate or acetone in 100 parts of sherwood oils of volume, thin-layer chromatography detects, and merges the stream part containing Ligustilide, be concentrated into solvent to the greatest extent, obtain highly purified Ligustilide.
Mixed solution sherwood oil in described step 2: the volume ratio of ether is preferably 100:4; Sherwood oil: the volume ratio of ethyl acetate is preferably 100:1; Sherwood oil: the volume ratio of acetone is preferably 100:0.5.
Thin-layer chromatography condition optimization sherwood oil: ethyl acetate=10:1 in described step 2.
Advantage of the present invention is: cost of material is cheap, and operation steps is simple, through simple supersound extraction, a silicagel column of mistake, can obtain purity and reach more than 98% Ligustilide.It can be used as chemical reference substance, for the quality control of Radix Angelicae Sinensis medicinal material and preparation thereof.
Accompanying drawing explanation
Fig. 1 is the HPLC collection of illustrative plates of the Ligustilide of the embodiment of the present invention 1 preparation.
Fig. 2 is the Ligustilide of the embodiment of the present invention 1 preparation
1h-NMR collection of illustrative plates.
Embodiment:
The Root of Garden Lovage adopting in following examples is taken from the Root of Garden Lovage that produce in Gansu, and its output is large, low price.
Embodiment 1
Get dry Gansu and produce Root of Garden Lovage pulverizing, take 100g powder, add 0.7L sherwood oil (60～90 ℃) soak at room temperature 2h, supersound extraction 2 times, each 1h, filters merging filtrate, and concentrating under reduced pressure extracting solution obtains paste.Then gained paste is separated with silica gel column chromatography, the solvent systems wash-out of employing sherwood oil: ethyl acetate=100:1, detects each flow point with thin-layer chromatography, and thin-layer chromatography condition is sherwood oil: ethyl acetate=10:1.Collect the stream part merging containing Ligustilide, concentrating under reduced pressure obtains Ligustilide sterling, and through high performance liquid phase, detecting its purity is 98.15%, and yield is 0.5%.
Ligustilide structural analysis:
Adopt nucleus magnetic resonance to carry out structural analysis to the Ligustilide sterling of embodiment 1, prove that it is Ligustilide, and data have been carried out to full ownership (see the following form 1, Fig. 2), with bibliographical information data consistent.
Table 1. Ligustilide
1h-NMR attribution data
The HPLC-UV liquid chromatography purity detecting of Ligustilide:
Getting aforesaid method, to prepare Ligustilide monomer appropriate, and methyl alcohol is dissolved in volumetric flask, after filtering with microporous membrane, adopts following condition to detect, and result shows that Ligustilide purity is 98.15% (seeing Fig. 1, table 2).
Table 2
| ? | Title | Retention time (minute) | Area (microvolt * second) | Highly (microvolt) |
| 1 | Peak 1 | 13.203 | 6253040 | 410461 |
| 2 | Peak 2 | 19.074 | 118087 | 6503 |
Chromatographic condition: Waters Alliance e2695HPLC instrument is (containing e2695 separating unit, 2489UV-Detector); Empower3 chromatographic working station; Chrom Matrix Innvation
tMultimate C
18(2) (5 μ m, 4.6 * 250mm) chromatographic column; Mobile phase A water, Mobile phase B acetonitrile, isocratic elution: A:B=40:60; Detect wavelength: 350nm; Flow velocity 1ml/min, 25 ℃ of column temperatures, sample size 100 μ l.
Embodiment 2
Get dry Gansu and produce Root of Garden Lovage pulverizing, take 150g powder, add 1.2L sherwood oil (60～90 ℃) soak at room temperature 3h, supersound extraction 3 times, each 1.5h, filters merging filtrate, and concentrating under reduced pressure extracting solution obtains paste.Then gained paste is separated with silica gel column chromatography, the solvent systems wash-out of employing sherwood oil: ether=100:4, detects each flow point with thin-layer chromatography, and thin-layer chromatography condition is sherwood oil: ethyl acetate=10:1.Collect the stream part merging containing Ligustilide, concentrating under reduced pressure obtains Ligustilide sterling, and through high performance liquid phase, detecting its purity is 98.59%, and yield is 0.55%.
Embodiment 3
Get dry Gansu and produce Root of Garden Lovage pulverizing, take 120g powder, add 1.1L sherwood oil (60～90 ℃) soak at room temperature 2.5h, supersound extraction 4 times, each 0.5h, filters merging filtrate, and concentrating under reduced pressure extracting solution obtains paste.Then gained paste is separated with silica gel column chromatography, the solvent systems wash-out of employing sherwood oil: acetone=100:0.5, detects each flow point with thin-layer chromatography, and thin-layer chromatography condition is sherwood oil: ethyl acetate=10:1.Collect the stream part merging containing Ligustilide, concentrating under reduced pressure obtains Ligustilide sterling, and through high performance liquid phase, detecting its purity is 98.23%, and yield is 0.52%.
Claims (5)
1. a method for separation and Extraction Ligustilide from Root of Garden Lovage, is characterized in that, comprises the steps:
Step 1: get dry Root of Garden Lovage and pulverize, adding liquid-solid ratio is the sherwood oil of 5～10ml ∕ g, soak at room temperature 1～5h, supersound extraction 1～5 time is extracted 0.5～2h at every turn, and gained extracting solution is merged, and filters, and concentrating under reduced pressure extracting solution obtains paste;
Step 2: the paste to step 1 gained is crossed silicagel column, to add the mixed solution wash-out of 0.5～5 part of ether or ethyl acetate or acetone in 100 parts of sherwood oils of volume, thin-layer chromatography detects, and merges the stream part containing Ligustilide, be concentrated into solvent to the greatest extent, obtain highly purified Ligustilide.
According to claim 1 from Root of Garden Lovage the method for separation and Extraction Ligustilide, it is characterized in that mixed solution sherwood oil in described step 2: the volume ratio of ether is 100:4.
According to claim 1 from Root of Garden Lovage the method for separation and Extraction Ligustilide, it is characterized in that mixed solution sherwood oil in described step 2: the volume ratio of ethyl acetate is 100:1.
According to claim 1 from Root of Garden Lovage the method for separation and Extraction Ligustilide, it is characterized in that mixed solution sherwood oil in described step 2: the volume ratio of acetone is 100:0.5.
According to claim 1 from Root of Garden Lovage the method for separation and Extraction Ligustilide, it is characterized in that, in described step 2, thin-layer chromatography condition is sherwood oil: ethyl acetate=10:1.
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| CN201410218763.3A CN103980237B (en) | 2014-05-22 | 2014-05-22 | A kind of method of separation and Extraction Z-ligustilide from Root of Garden Lovage |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105079059A (en) * | 2015-09-07 | 2015-11-25 | 宜诺(天津)医药工程有限公司 | Angelica sinensis extract and extraction method |
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| CN1552702A (en) * | 2003-06-03 | 2004-12-08 | 北京九龙制药厂 | Medicinal use and extraction of cis-ligusticum lactone |
| CN1778799A (en) * | 2005-07-08 | 2006-05-31 | 钱忠明 | Fast production of high-purity radix ligustici sinensis lactone |
| CN101088996A (en) * | 2007-07-18 | 2007-12-19 | 兰州大学 | Process of extracting and separating ligustilide from angelica |
| CN102260232A (en) * | 2010-05-28 | 2011-11-30 | 上海诗丹德生物技术有限公司 | Preparation method of Z-ligustilide |
| CN102813687A (en) * | 2012-10-12 | 2012-12-12 | 天津中医药大学 | Use of ligustilide in preparing anti-thrombotic medicines |
| CN102872175A (en) * | 2012-08-24 | 2013-01-16 | 天津中医药大学 | Ligusticum chuanxiong hort extract and preparation method and application thereof |
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2014
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| CN1552702A (en) * | 2003-06-03 | 2004-12-08 | 北京九龙制药厂 | Medicinal use and extraction of cis-ligusticum lactone |
| CN1778799A (en) * | 2005-07-08 | 2006-05-31 | 钱忠明 | Fast production of high-purity radix ligustici sinensis lactone |
| CN101088996A (en) * | 2007-07-18 | 2007-12-19 | 兰州大学 | Process of extracting and separating ligustilide from angelica |
| CN102260232A (en) * | 2010-05-28 | 2011-11-30 | 上海诗丹德生物技术有限公司 | Preparation method of Z-ligustilide |
| CN102872175A (en) * | 2012-08-24 | 2013-01-16 | 天津中医药大学 | Ligusticum chuanxiong hort extract and preparation method and application thereof |
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| P.LI ET AL: "Optimization of pressurized liquid extraction for Z-ligustilide, Z-butylidenephthalide and ferulic acid in Angelica sinensis", 《JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105079059A (en) * | 2015-09-07 | 2015-11-25 | 宜诺(天津)医药工程有限公司 | Angelica sinensis extract and extraction method |
| CN105079059B (en) * | 2015-09-07 | 2020-03-31 | 宜诺(天津)医药工程有限公司 | Angelica sinensis extract and extraction method thereof |
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