CN1470518A - Method for extracting quercetin-7-0-rhamnoside - Google Patents
Method for extracting quercetin-7-0-rhamnoside Download PDFInfo
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- CN1470518A CN1470518A CNA031269931A CN03126993A CN1470518A CN 1470518 A CN1470518 A CN 1470518A CN A031269931 A CNA031269931 A CN A031269931A CN 03126993 A CN03126993 A CN 03126993A CN 1470518 A CN1470518 A CN 1470518A
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Abstract
The present invention relates to a method for extracting quercetin-7-O-rhamnoside monmer from Chinese medicinal material containing quercetin-7-O-rhamnoside, which includes the following steps: pulverizing Chinese medicinal material, extracting with water for once to several times, filtering, combining filtrates, concentrating to obtain extract, alcohol precipitation, column separation at twice, eluting with organic solvent, volatilizing solvent from eluant. Its preparation process is simple, and said monomer content in its product is up to above 95%.
Description
Technical field
The present invention relates to a kind of Quercetin-7-O-rhamnoside monomer methods of from the Chinese medicinal materials Herba Hyperici Japonici, extracting.
Background technology
Quercetin-7-O-rhamnoside is a kind of flavonoid compound, is present in the Chinese medicinal materials Herba Hyperici Japonici.Herba Hyperici Japonici (Hypericum japonicum Thunb.) is used for the treatment of hepatitis, and its contained Quercetin-7-O-rhamnoside is that it mainly contains one of effective constituent.
The acquisition approach of Quercetin-7-O-rhamnoside can obtain by extracting from the medicinal material Herba Hyperici Japonici.But owing to contain various flavonoids in the Chinese medicinal materials, and polyose, tannin, materials such as coumarins, and also contain the close material of multiple structure in the Flavonoid substances.Obtain Quercetin-7-O-rhamnoside monomer, need come Quercetin-7-O-rhamnoside and other various separating substances.Research is in the past failed to provide a kind of and can be obtained the monomeric feasible extracting method that can be used for suitability for industrialized production of Quercetin-7-O-rhamnoside in a large number.
The structural formula of Quercetin-7-O-rhamnoside is shown below, R in the formula
1=rhamnosyl, R
2=H;
Quercetin-7-O-rhamnoside
Summary of the invention
The purpose of this invention is to provide a kind of Quercetin-7-O-rhamnoside monomer methods of from the Chinese medicinal materials that contains Quercetin-7-O-rhamnoside, extracting.This method has simple, is applicable to the characteristics of suitability for industrialized production.
The step of Quercetin of the present invention-7-O-rhamnoside extracting method comprises:
The medicinal material that 1. will contain Quercetin-7-O-rhamnoside through one to multiple water extraction, filters merging filtrate;
2. filtrate is condensed into medicinal extract, and upper prop or direct upper prop carry out post and separate the organic solvent wash-out behind the medicinal extract alcohol precipitation;
3. elutriant volatilizes solvent, gets Quercetin-7-O-rhamnoside crude product; Carry out the secondary post again and separate, the organic solvent wash-out, elutriant volatilizes solvent, gets Quercetin-7-O-rhamnoside monomer (pure product).
The medicinal material that contains Quercetin-7-O-rhamnoside that the inventive method is used can be a Herba Hyperici Japonici.Before the water extraction preferably earlier pulverizing medicinal materials or be cut into medicine materical crude slice.
Water extraction in the inventive method can adopt under ℃ condition of room temperature～100 or/and carry out under the ultrasonic wave condition; Extraction time is generally one to three time, and the number of times increase is not limit.The consumption of water is that water can not have medicinal material at least, and water consumption is not too much limit.Extraction time was generally 0.1-24 hour, and time lengthening is not limit.Heat or/and extract under the ultrasonic wave condition and can shorten extraction time.
The used ethanol of medicinal extract alcohol precipitation in the inventive method can be the ethanol of dehydrated alcohol or various concentration; After adding ethanol sedimentation, the ethanol ultimate density of mixing liquid can be 5% to 95% various concentration.
Post in the inventive method separates, and the column packing of employing can be silica gel, aluminum oxide, polymeric amide or macroporous resin.Usually, the isolating column packing of post can adopt polymeric amide or macroporous resin ion exchange resin first, and the isolating filler of secondary post can adopt silica gel or aluminum oxide.
Organic solvent wash-out in the inventive method, organic solvent can adopt various organic solvents commonly used such as ethanol, methyl alcohol, chloroform, ethyl acetate or sherwood oil.The concentration of organic solvent can adopt various concentration, comprises that concentration is 100% organic solvent.Usually, the used organic solvent of post separation wash-out can be and comprises that concentration is the ethanol or the methanol in water of the various concentration of 10-100% first, and the secondary post separates used organic solvent and can be chloroform, ethyl acetate, ethanol, methyl alcohol or their mixed solution.
Adopt Quercetin of the present invention-7-O-rhamnoside extracting method, extract Quercetin-7-O-rhamnoside monomer (pure product) Quercetin-7-O-rhamnoside medicinal material from different containing, extract yield all more than 80%, Quercetin in gained Quercetin-7-O-rhamnoside sample-monomeric content of 7-O-rhamnoside reaches more than 95%.
Adopt the resulting Quercetin of the inventive method-7-O-rhamnoside monomer (pure product), through measuring, and detect purity with the three-dimensional collection of illustrative plates of its high performance liquid phase by " Chinese people republic pharmacopeia " 2000 editions high performance liquid chromatography.The result shows that Quercetin in the sample-monomeric content of 7-O-rhamnoside is higher than 95%.Show feasible process of the present invention.
Quercetin of the present invention-7-O-rhamnoside extracting method, it is simple to have extraction process, and the extraction yield height extracts the Quercetin-characteristics such as 7-O-rhamnoside monomer purity height that obtain, and is applicable to suitability for industrialized production.
Description of drawings
Fig. 1 is the resulting Quercetin of the inventive method-monomeric high-efficient liquid phase chromatogram of 7-O-rhamnoside.
Fig. 2 is the resulting Quercetin of the inventive method-monomeric high performance liquid phase three dimensional chromatogram of 7-O-rhamnoside.
Embodiment
The present invention is described further below in conjunction with embodiment.
Solid in the involved solid mixture of each embodiment, the liquid in the liquid, and the solid per-cent in the liquid is respectively with wt/wt, and vol/vol, wt/vol calculates, except as otherwise noted.
Embodiment 1:
The Herba Hyperici Japonici medicinal material is cut into medicine materical crude slice, adds 8 times of amounts of water, decocts to extract three times, each one hour, filters; Filtrate is condensed into medicinal extract, crosses polyamide column, behind 40% ethanol elution, uses 70% ethanol elution again; Collect 70% ethanol eluate, elutriant reclaims ethanol, must precipitate, after precipitation is used the silica gel mixing, and last silicagel column, with eluent ethyl acetate, elutriant reclaims ethyl acetate, gets Quercetin-7-O-rhamnoside monomer.Yield is 82.3%.
Embodiment 2:
The Herba Hyperici Japonici pulverizing medicinal materials adds 100 ℃ of water and there was not medicinal material, extracts three times, each 1 hour, filters merging filtrate; Filtrate concentrates, and adding dehydrated alcohol is 70% to alcohol concn, and placement is spent the night, and filters, and supernatant liquor reclaims ethanol.Medicinal extract is crossed polyamide column, uses 40% ethanol elution earlier, uses 70% ethanol elution again; Collect 70% ethanol eluate, elutriant reclaims ethanol, must precipitate with behind the silica gel mixing, and last silicagel column, with eluent ethyl acetate, elutriant reclaims ethyl acetate, gets Quercetin-7-O-rhamnoside monomer.Yield is 84.5%.
Embodiment 3:
The Herba Hyperici Japonici medicinal material is cut into medicine materical crude slice, through 70 ℃ of floodings twice, each 3 hours, filters merging filtrate; Filtrate is condensed into medicinal extract, and it is 60% that medicinal extract adds 95% ethanol to alcohol concn, and standing over night produces precipitation, filters, and goes precipitation, filtrate recycling ethanol, and medicinal extract is crossed polyamide column, uses 40% ethanol elution earlier, uses 70% ethanol elution again; Collect 70% ethanol eluate, elutriant reclaims ethanol, must precipitate with behind the aluminum oxide mixing, and last alumina column, with ethanol elution, elutriant reclaims ethanol, gets Quercetin-7-O-rhamnoside monomer.Yield is 78.5%.
Embodiment 4:
The Herba Hyperici Japonici medicinal material is not pulverized, and through ultrasonic wave water extraction 4 times, each 30 minutes, filters merging filtrate; Concentrate, get medicinal extract, cross polyamide column, behind 40% ethanol elution, use 70% ethanol elution again; Collect 70% ethanol eluate, elutriant reclaims ethanol, must precipitate, after precipitation is used the silica gel mixing, and last silicagel column, with the chloroform wash-out, elutriant reclaims chloroform, gets Quercetin-7-O-rhamnoside monomer.Yield is 80.3%.
Embodiment 5: Quercetin-7-O-rhamnoside monomer purity determination experiment
It is an amount of to get Quercetin-7-O-rhamnoside monomer that the said extracted method prepares, the dissolve with methanol constant volume in volumetric flask, use millipore filtration (0.45um) to filter again after, inject high performance liquid chromatograph, can obtain its high-efficient liquid phase chromatogram (Fig. 1).Carry out three-dimensional collection of illustrative plates scanning, obtain high performance liquid chromatography three dimensional chromatogram (Fig. 2).Utilize its three-dimensional collection of illustrative plates (Fig. 2) to observe its purity, utilize normalization method to calculate it and extract Quercetin-monomeric content of 7-O-rhamnoside in gained Quercetin-7-O-rhamnoside sample.Going up us from its three-dimensional collection of illustrative plates (Fig. 2) can observe it and not have other materials appearance at the peak that its high-efficient liquid phase chromatogram (Fig. 1) removes Quercetin-7-O-rhamnoside.
Chromatographic condition: Agilent1100 high performance liquid chromatograph (automatic sampler, vacuum degassing machine, quaternary pump, column oven, diode-array detector); Chromatographic column: MERKER ODS post (5um, 4.0 * 250mm); Moving phase: methyl alcohol-Glacial acetic acid-water (35: 4: 61); Detect wavelength: 370nm; Column temperature: 30 ℃; Flow velocity: 1ml/min; Sample size: 5 μ l.
Find out do not have other impurity peaks in the high performance liquid phase one dimension of extraction gained sample and the three-dimensional collection of illustrative plates except that Quercetin-7-O-rhamnoside from the result, wherein Quercetin-monomeric content of 7-O-rhamnoside is higher than 95%.The resulting Quercetin of extracting method of the present invention-7-O-rhamnoside sample purity height is described.
In addition, the Quercetin-7-O-rhamnoside monomer of gained has been carried out fusing point test, its fusing point is 274.0～274.5 ℃, and its melting range has only 0.5 ℃, illustrates that also its purity is very high.
In sum, Quercetin of the present invention-7-O-rhamnoside extracting method is described, can from contain Quercetin-7-O-rhamnoside medicinal material, extract effectively and obtain Quercetin-7-O-rhamnoside monomer, gained Quercetin-7-O-rhamnoside sample purity height, content all is higher than more than 95%, and the technology simple possible.
Claims (8)
1. the extracting method of Quercetin-7-O-rhamnoside may further comprise the steps successively:
The Chinese medicinal materials that 1. will contain Quercetin-7-O-rhamnoside through one to multiple water extraction, filters merging filtrate;
2. filtrate is condensed into medicinal extract, and upper prop or direct upper prop carry out post and separate the organic solvent wash-out behind the medicinal extract alcohol precipitation;
3. elutriant volatilizes solvent, gets Quercetin-7-O-rhamnoside crude product; Quercetin-7-O-rhamnoside crude product carries out the secondary post again to be separated, the organic solvent wash-out, and elutriant volatilizes solvent, gets Quercetin-7-O-rhamnoside monomer.
2. in accordance with the method for claim 1, it is characterized in that before the water extraction earlier or be cut into medicine materical crude slice pulverizing medicinal materials.
3. according to claim 1 or 2 described methods, it is characterized in that the said Chinese medicinal materials that contains Quercetin-7-O-rhamnoside is a Herba Hyperici Japonici.
4. according to the described method of claim 1,2 or 3, it is characterized in that said water extraction is or/and carry out under the ultrasonic wave condition under room temperature to 100 ℃ condition; Extraction time is one to three time.
5. in accordance with the method for claim 4, the extraction time that it is characterized in that said water extraction is 0.1-24 hour.
6. according to the described method of claim 1,2 or 3, it is characterized in that the used ethanol of said medicinal extract alcohol precipitation is the ethanol of dehydrated alcohol or various concentration; After adding ethanol sedimentation, the ethanol ultimate density of mixing liquid is 5% to 95% various concentration.
7. according to the described method of claim 1,2 or 3, it is characterized in that it is polymeric amide or macroporous resin ion exchange resin that said post first separates the column packing that adopts, it is silica gel or aluminum oxide that the secondary post separates the filler that adopts.
8. according to claim 1,2 or 3 described methods, it is characterized in that the used organic solvent of post separation wash-out is to comprise that concentration is the ethanol or the methanol in water of the various concentration of 10-100% first, it is chloroform, ethyl acetate, ethanol, methyl alcohol or their mixed solution that the secondary post separates used organic solvent.
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| CNB031269931A CN1185246C (en) | 2003-06-26 | 2003-06-26 | Method for extracting quercetin-7-0-rhamnoside |
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| CNB031269931A CN1185246C (en) | 2003-06-26 | 2003-06-26 | Method for extracting quercetin-7-0-rhamnoside |
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| CN1185246C CN1185246C (en) | 2005-01-19 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592331A (en) * | 2015-02-03 | 2015-05-06 | 天津科技大学 | Quercetin derivative as well as preparation process and application thereof |
| CN105037466A (en) * | 2015-08-13 | 2015-11-11 | 华润三九医药股份有限公司 | Method of extracting and separating vincetoxicoside B from hypericum japonicum |
| WO2015169121A1 (en) * | 2014-05-05 | 2015-11-12 | 南京睿鹰润泽生物医药科技有限公司 | Use of quercetin-o-glycoside derivatives in treating lipid metabolism disorders |
| CN114315931A (en) * | 2022-01-18 | 2022-04-12 | 集美大学 | Method for preparing quercetin-7-O-L-rhamnoside from fructus Phyllanthi |
-
2003
- 2003-06-26 CN CNB031269931A patent/CN1185246C/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015169121A1 (en) * | 2014-05-05 | 2015-11-12 | 南京睿鹰润泽生物医药科技有限公司 | Use of quercetin-o-glycoside derivatives in treating lipid metabolism disorders |
| CN104592331A (en) * | 2015-02-03 | 2015-05-06 | 天津科技大学 | Quercetin derivative as well as preparation process and application thereof |
| CN104592331B (en) * | 2015-02-03 | 2017-03-29 | 天津科技大学 | A kind of quercetin derivative and its preparation technology and application |
| CN105037466A (en) * | 2015-08-13 | 2015-11-11 | 华润三九医药股份有限公司 | Method of extracting and separating vincetoxicoside B from hypericum japonicum |
| CN105037466B (en) * | 2015-08-13 | 2018-05-04 | 华润三九医药股份有限公司 | A kind of method of the extraction separation Quercetin-7-BETA-D-rhamnose from hypericum japonicum |
| CN114315931A (en) * | 2022-01-18 | 2022-04-12 | 集美大学 | Method for preparing quercetin-7-O-L-rhamnoside from fructus Phyllanthi |
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| CN1185246C (en) | 2005-01-19 |
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