CN1560069A - Process for extracting total flavone and total oside of astragalus from astragalus - Google Patents
Process for extracting total flavone and total oside of astragalus from astragalus Download PDFInfo
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Abstract
The invention relates to the extraction of effective components from Chinese medicinal herb, especially a method of extracting Radix astragali total flavone and total glucoside from Radix astragali, using organic solvent to extract, using absorbing resin to enrich total flavone and total glucoside, and then using ion exchange resin to separate the two from each other, the process simple, the cost low, the losses low, and the product quality high, no environmental protection. It uses multicolumn, thus heightening extracting efficiency and avoiding the losses of effective components. The used resin has stable structure and stain resistance, easy to regenerate, has very high selectivity to the total flavone and total glucoside of Radix astragali, separates the Radix astragali flavone compound and the sopanin compound from the Radix astragali at the same time, then further separating two types of compounds from each other.
Description
Technical field
The present invention relates to the extraction of Chinese herbal medicine effective ingredients, particularly from the Radix Astragali, extract the method for Radix Astragali total flavones and general glycoside.
Background technology
Radix Astragali flavone compounds (I) and oside compound (II) all are the effective chemical compositions in the Radix Astragali, and oside compound has step-down, anti-inflammatory, calm, analgesia improves plasma cAMP content, promotes the effects such as reaction immunologic function that mouse Liver Regeneration DNA is synthetic and improve the mouse lymph organ.The isoflavonoid physiologically active is remarkable, and coronary artery dilator is arranged, and increases coronary blood-flow volume, reaches the effect that reduces myocardial oxygen consumption.Have effects such as sweating, analgesic, spasmolysis on the pharmacology.The Astragalus leguminous plants, the isoflavones in the leguminous plants also has female hormone, and anti-oxidant and haemolysis and anti-cholesterol and blood fat are antibacterial, press down the enzyme isoreactivity.
R1:-O-glucose, OH, H; R2:H; R3:H, OH; R4:OH, H; R5:-O-glucose
I-R
1＝2，3-O-diacetyl-β-D-xylopyranosyl；R
2＝β-D-xylopyranosyl；
II-R
1＝2-O-acetyl-β-D-xylopyranosyl；R
2＝β-D-xylopyranosyl；
III-R
1＝R
2＝2，3，4-triacetyl-β-D-xylopyranosyl；
IV-R
1＝2，3-O-diacetyl-β-D-xylopyranosyl
The extraction of middle pharmaceutically active ingredient, separation are the committed steps that realizes the modernization of Chinese medicine, how to respect on the traditional basis of Chinese materia medica, and the extraction separation of pharmaceutically active ingredient in finishing also is the vast medical worker's of puzzlement a problem.Resin method is demonstrating special advantages really aspect the extraction separation of herbal medicine chemical ingredients.Its organic solvent consumption less, technology simple and flexible, production cost be lower.Can reach in the known effective constituent of enrichment to greatest extent, keep not principal component when abandoning known invalid components by different Choice of Resin, this separation method than other more meets the Chinese materia medica characteristic.The Radix Astragali (Astragalus mongholicus Bunge) belongs to leguminous plants, is conventional Chinese medicine, the effect that having induces sweat brings down a fever, promotes the production of body fluid to quench thirst.Flavones and saponin are two kinds of effective constituents in the Radix Astragali.All carried out the research of from the Radix Astragali, extracting total flavones and saponin at present both at home and abroad.Research to flavones only limits to the content of flavones in the Radix Astragali and analogue thereof and the research of structure thereof.Related extracting method is that chromatography method (Sun Hui, Liu Yubin etc., the Radix Astragali survive the winter on the ground the assay of Radix Astragali total flavones and total saponin in the deadwood, Transactions of the Chinese Society of Agricultural Engineering, 2000,16 (5), 117) can't be used for producing.
To the extracting method of astragaloside, Yan Qiaojuan etc. have reported [extraction and separation method of astragaloside, China Agricultural University's newspaper, 2000,5 (6), 61] water extraction; Alcohol extracting method; Extraction process; Resin adsorption method and supercritical CO
2Method.The purpose of these methods all is in order to extract saponin from the Radix Astragali, yet these methods also can extract materials such as flavones when extracting astragaloside simultaneously.Shown method is not further with oside compound and flavonoid compound separating process.So this method and imperfection, dna purity are not high yet, and the waste resource.
Jiang Yaqiang etc. [resin adsorption method extracts astragaloside, China Agricultural University's journal, 2000,5 (6), 66] have provided with resin method and have extracted astragaloside, and its technical characterictic is at first to use the extraction using alcohol saponin, are dissolved in water after concentrating, and cross post then, use ethanol elution again.There is same problem in this technology with technology shown in above-mentioned.In addition, Qi Zongshao etc. disclose the saponin structure demonstration of [Radix Astragali The Chemical Constituents overview, herbal medicine, 1987,18 (5), 41], and oside compound is soluble in ethanol and is insoluble in water, so this technology is at first used the extraction using alcohol saponin.Be difficult to guarantee in the oside compound water inlet that use ethanol elution after crossing post, the use of solvent seemingly has incompatibility with water dissolution yet concentrate the back.
Chinese patent CN1330082A[Han Lu is good, Yan Qiaojuan etc., the extraction and separation method of astragalus polysaccharides and astragaloside] there is above-mentioned problem equally in disclosed technology.
Though above-mentioned document has been reported comparatively detailed method, equally also none carries out separating process with flavonoid compound and oside compound.
Summary of the invention
The purpose of this invention is to provide a kind of method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside.The present invention is the method for purifying of separating that is used for Radix Astragali total flavones and general glycoside, and this method technology is simple, cost is low, loss is little, quality product is high.This resin structure is stable, and contamination resistance is strong, is easy to regeneration, and Radix Astragali total flavones and general glycoside are had very high selectivity, and Radix Astragali flavone compounds and oside compound are separated from the Radix Astragali simultaneously, further two compounds is separated then.
The present invention includes following steps:
1) with pulverizer dried Radix Astragali rhizome raw material is broken into coarse meal or is cut into the 2-3cm quarter butt and put into container, add organic solvent, extract at-10～70 ℃ of 1～10h that reflux, or add water extraction; Feed ratio is a raw material: organic solvent=1: 1～20.Described organic solvent is: hydro carbons, and alcohols, ethers, the ester class, ketone, all organic solvents such as haloalkane are as ethanol, methyl alcohol, propyl alcohol, acetone, butanone, ether, tetrahydrofuran (THF) or their mixing.
2) said extracted liquid is filtered, be cooled to room temperature, left standstill 2-15 days, have sucrose to separate out, the sucrose amount of separating out is the 1%-15% of astragalus weight.Sucrose contains a small amount of astragalus polysaccharides, and flavonoid and saponin class and other astragalus root components are so Radix Astragali sucrose also is a kind of good healthcare products.
Through the said extracted process, those dissolve in the material of organic solvents such as ethanol, and as flavonoid, but saponin class and other a small amount of thing major parts enter in the organic solvent solution.
3) extracting solution that will remove sucrose adds the water of 10-200%, and the scope that adds water is 10-30% preferably.
4) fractionation by adsorption, by the fractionation by adsorption post, polymeric adsorbent can use H-107 or other various polymeric adsorbents and sorbing material, preferably three post coupling (see figure 1)s with above-mentioned solution.Flow velocity 3-5mL/min, or wider, can determine as the case may be.Adsorption effect is seen Fig. 2.
5) resolve: with acetone, butanone waits other organic solvent (to comprise alcohols, ketone for resolving reagent, ethers, organic reagents such as haloalkane), resolve in room temperature and other suitable temperature, or 40～70 ℃ of ethanol, or 40～100 ℃ of water, or the mixed solution of water and organic solvent.Flow velocity is 0.2-0.6mL/min, or other is wider, can determine according to other particular case.The desorbed solution consumption is 2-6 times resin volume or bigger consumption.Resolve effect and see Fig. 3
6) ion-exchange, by negatively charged ion cross-linked resin post, flow velocity is 0.2-0.6mL/min with desorbed solution, and Flavonoid substances is stayed on the resin column, and glycoside compound is present in the effluent liquid, thereby with two kinds of materials separately.Concentrated effluent liquid gets glycoside compound.
7) with the NaOH aqueous solution of 1-10% flavonoid compound is resolved.Resolve effect and see Fig. 4.
8) with the desorbed solution of ion exchange column with hydrochloric acid or sulfuric acid acidation after, branch vibration layer, wash several all over get final product Flavonoid substances.
Except that using ethanol to do the desorbed solution, other organic solvents all can be used as desorbed solution as acetone, butanone, propyl alcohol etc.Desorbed solution also comprises 40-100 ℃ of water.The mixed solution of the mixed solution of all above-mentioned organic solvents and they and water also can be as desorbed solution.
Resolving of the present invention can be in the freezing point of desorbed solution to carrying out (room temperature to 50 ℃ best) between the boiling point, the consumption of desorbed solution is that 2 times to 6 times resin volume is advisable, or more.Speed is advisable at 0.2～0.6mL/min, or other speed.Saponin and Flavonoid substances get off resolved.Resin column is crossed water then, and after desorbed solution replacement only, resin column can continue to use.
Ion exchange process is that flavonoid compound and oside compound are separated.Its principle is that flavonoid compound contains active phenolic hydroxyl group, and this group shows acidity, thus available strong alkali ion exchange resin exchange, and oside compound do not contain can be for the active group that exchanges, so but spent ion exchange resin they are separated.Exchange mechanism is as follows:
Annotate: be to simplify expression formula, above-mentioned flavonoid compound only with wherein a kind of be representative.
After desorbed solution was crossed post, Flavonoid substances was stayed on the post, and oside compound is present in the effluent liquid.This goes on foot used resin and comprises all anionite-exchange resin.Ion exchange resin is removed oligopolymer before using, and handles with the 1-10%NaOH aqueous solution again, is washed to neutrality.
Resolving exchange column is to pass through ion exchange column with the 1-10%NaOH aqueous solution, and flavonoid compound is resolved to get off, and is present in the desorbed solution.
Exchange column is washed till neutrality with deionized water, continues to use.
Saponin that aforesaid method is obtained and Flavonoid substances with dissolve with ethanol after, remove the clear liquid of post precipitation, vapor away ethanol and can obtain highly finished product.
Adopt the H-107 resin, the H-107 resin is used acetone extraction 24 hours in the fat extraction device, to remove oligopolymer.Then resin is dosed in the adsorption column, flowed out distilled water, can use after changing acetone with suitable speed.
The design of adsorption column, except that single-column used, the multicolumn coupling was good, is preferably 3 adsorption columns and uses simultaneously, can obtain best extraction effect like this.As shown in Figure 1.Extracting solution enters 3 adsorption column models shown in Fig. 1-1 at first in turn, after the 3rd adsorption column begins to leak, begins to resolve first post, can reuse after parsing finishes.When first post was resolved, the B post became first post, and inserts a new post (D), and the rest may be inferred later on.Shown in Fig. 1-2.
The present invention is used for the method for purifying of separating of Radix Astragali total flavones and general glycoside, and technology is simple, cost is low, loss is little, quality product is high, non-environmental-pollution.The multicolumn coupling has improved the efficient of extracting, and has avoided loss of active ingredients.The resin structure that the present invention uses is stable, and contamination resistance is easy to regeneration, and Radix Astragali total flavones and general glycoside are had very high selectivity, and Radix Astragali flavone compounds and oside compound are separated from the Radix Astragali simultaneously, further two compounds is separated then.
Description of drawings
Fig. 1. three post coupling synoptic diagram.
Fig. 2. the adsorption effect curve.
Fig. 3. flavonoid and the oside compound parsing effect on adsorption column.
Fig. 4. the parsing effect of flavonoid compound on ion exchange column.
Embodiment
Embodiment
In the 5000ml there-necked flask, put into pulverizer and will do the 2-3cm quarter butt that 700g Radix Astragali rhizome is cut into, add the ethanol of 3500mL95%, at 70 ℃ of refluxing extraction 1.5h.Emit extracting solution 2500ml.Said extracted liquid is filtered, be cooled to room temperature, left standstill 5 days, have sucrose to separate out, filter, the extracting solution of removing sucrose is added 400mL water.Cross the H-107 resin column, flow velocity 4mL/min.
After the adsorption equilibrium,, resolve with the speed of 0.4mL/min at 30 ℃ with acetone, the desorbed solution consumption is 5 times a resin volume; By D-208 strong anion-exchange resin (Chemical Plant of Nankai Univ.'s production) post, flow velocity is 0.4mL/min with desorbed solution, and Flavonoid substances is stayed on the resin column, glycoside compound is present in the effluent liquid, thereby with two kinds of materials separately, vapor away solvent, get glycoside compound at 50 ℃; The NaOH aqueous solution with 5% resolves flavonoid compound get off, and flow velocity is 0.4mL/min, and the desorbed solution consumption is 4 times a resin volume, resolves effect and sees Fig. 4.
With the desorbed solution of ion exchange column with 20% hcl acidifying to pH=3, branch vibration layer is washed to pH=6, get final product Flavonoid substances.
Absorption result is plotted among Fig. 2.
Resin treatment process before use: the H-107 resin is used acetone extraction 24 hours in the fat extraction device, to remove oligopolymer.Then resin is dosed in the adsorption column, flowed out distilled water with 4mL/min, change the adsorption resin column (Fig. 1, three post couplings) of packing into behind the acetone, every post is equipped with 70mL H-107 polymeric adsorbent (used H-107 resin commercialization, Chemical Plant of Nankai Univ. produces).After the C post begins to leak, remove the A post and resolve.Add a post (D) more in addition, from the charging of B post, the B post becomes first post.After the A post is resolved and finished, continue to use, enter system from the back, as the D post.So every post all can recycle for a long time.
Assay.
The preparation of standard substance.The purity of Japan, Shandong vegetable oil mill production is 50% soybean isoflavones sample, purifies repeatedly 3 times, and liquid-phase chromatographic analysis 96.9% is a standard substance.
The drafting of typical curve.Is the solution of 0.075g/L with above-mentioned standard substance with the ethanol compound concentration, is A with this concentration, prepares 0.8A more respectively, 0.6A, the solution of 0.4A and 0.2A, drawing standard curve y=11.8x+0.008.
Adsorption effect is analyzed
A curve from Fig. 2 occurs leaking about the 9th integration greatly as can be known, and the content of the 26th integration is 2.4g/L, and the concentration well below the 5.12g/L of extracting solution illustrates that resin column does not also reach adsorption equilibrium.The solution that merges 26 integrations is crossed the B post, from the curve of the B of Fig. 2 as can be known, begin to occur leaking at the 14th integration, and the concentration of the 25th integration has only 1.2g/L, merges 25 integration liquid to cross the C post, and curve C shows the almost not leakage of 24 integrations.Three post couplings have guaranteed not loss of adsorptive.
Saponin that aforesaid method is obtained and Flavonoid substances put into the 50mL Erlenmeyer flask with a small amount of 95% dissolve with ethanol after, leave standstill, clear liquid is poured in the little weighing bottle of accurate weighing, Erlenmeyer flask is washed 3 times with a small amount of alcohol, clear liquid is poured in the weighing bottle, vapored away alcohol and promptly obtain purified saponin and flavonoid compound.Yield sees Table 1:
The lab scale yield of table 1 saponin and Flavonoid substances
| Numbering | Index | Milkvetch Root quality (g) | Thick Astragaloside (g) | Refining astragalus glucoside (g) | Thick Radix Astragali flavone class (g) | Refining astragalus flavonoid (g) |
| ??1 | Output | ????700 | ??0.3172 | ??0.2245 | ????0.6615 | ????0.4732 |
| Yield | ??0.032％ | ????0.068％ | ||||
| Purity | ??95.8％ | ????95.1％ | ||||
| ??2 | Output | ????700 | ??0.3218 | ??0.2253 | ????0.5972 | ????0.4813 |
| Yield | ??0.032％ | ????0.068％ | ||||
| Purity | ??95.6％ | ????95.4％ |
Embodiment 2 operation stepss the results are shown in Table 2 with embodiment 1.
The pilot scale yield of table 2 saponin and Flavonoid substances
| Milkvetch Root weight (kg) | Thick Astragaloside (kg) | Refining astragalus glucoside (kg) | Thick Radix Astragali ketone (kg) | Refining astragalus ketone (kg) |
| ????500 | ???0.6587 | ????0.4582 | ????1.7814 | ????1.4277 |
| Yield | ????0.09％ | ????0.29％ | ||
| Purity | ????96.1％ | ????94.2％ |
Claims (10)
1, a kind of method of extracting Radix Astragali total flavones and general glycoside from the Radix Astragali is characterized in that it comprises the steps:
1) with pulverizer Radix Astragali rhizome raw material is broken into coarse meal or is cut into the 2-3cm quarter butt and put into container, add organic solvent, extract at-10～70 ℃ of 1～10h that reflux down, or water logging is extracted; Feed ratio is a raw material: solvent=1: 1～20;
2) said extracted liquid is filtered, be cooled to room temperature, left standstill 2-15 days, have sucrose to separate out;
3) remove the water that extracting solution after the sucrose adds 10-200%;
4) fractionation by adsorption is passed through polymeric adsorbent separator column, flow velocity 3-5mL/min with above-mentioned solution;
5) at room temperature resolve to 50 ℃ as desorbed solution with organic solvent, or 40-100 ℃ of hydrolysis analyse, or the mixed solution of water and organic solvent resolves, flow velocity is 0.2-0.6mL/min, and the desorbed solution consumption is a 2-6 resin volume doubly;
6) ion-exchange, by anion-exchange resin column, flow velocity is 0.2-0.6mL/min with desorbed solution, and Flavonoid substances is stayed on the resin column, and glycoside compound is present in the effluent liquid; Concentrated effluent liquid under 40～80 ℃ gets glycoside compound;
7) with the NaOH aqueous solution of 1-10% flavonoid compound is resolved, flow velocity is 0.2-0.6mL/min, and the desorbed solution consumption is a 2-6 resin volume doubly;
8) with the desorbed solution of ion-exchange with hydrochloric acid or sulfuric acid acidation to pH≤5, till the material that no longer settles out, branch vibration layer is washed to pH=5～7, get final product Flavonoid substances.
2, according to the described method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside of claim 1, it is characterized in that described organic solvent is ethanol, methyl alcohol, propyl alcohol, acetone, butanone, ether, tetrahydrofuran (THF) or their mixing.
3, according to the described method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside of claim 2, it is characterized in that described organic solvent is 60～95% ethanol.
4, according to the described method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside of claim 1, it is characterized in that before crossing adsorption column, leaving standstill and remove sugar, the sucrose amount of separating out is the 1%-15% of astragalus weight.
5, according to the described method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside of claim 1, it is characterized in that the described extracting solution of removing sucrose adds entry 10-30%.
6, according to the described method of extracting Radix Astragali total flavones and general glycoside from the Radix Astragali of claim 1, the organic solvent desorbed solution that it is characterized in that described polymeric adsorbent separator column is ethanol, acetone, butanone or propyl alcohol, or 40-100 ℃ of water.
7, according to the described method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside of claim 6, it is characterized in that described desorbed solution is an acetone, butanone or 40～70 ℃ of ethanol.
8, according to the described method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside of claim 1, it is characterized in that described polymeric adsorbent is the H-107 polymeric adsorbent.
9, according to the described method of from the Radix Astragali, extracting Radix Astragali total flavones and general glycoside of claim 1, it is characterized in that institute's spent ion exchange resin is a strong alkali ion exchange resin.
10, the described polymeric adsorbent separator column that extracts the method for Radix Astragali total flavones and general glycoside from the Radix Astragali of claim 1 is to adopt three post couplings.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100348606C (en) * | 2005-07-08 | 2007-11-14 | 南京大学 | Preparation method of astilbin |
| CN102060825A (en) * | 2009-11-13 | 2011-05-18 | 天津市食品研究所有限公司 | Method for extracting flavone from young barley grass |
| CN101073592B (en) * | 2006-05-18 | 2011-08-10 | 天津天士力制药股份有限公司 | Method for separating and extracting Milkvetch Root |
| CN102188475A (en) * | 2011-06-21 | 2011-09-21 | 李宝生 | Application of total flavonoids of astragalus in preparing pharmaceutical for preventing and treating acute radiation pneumonitis |
| CN102266378A (en) * | 2011-08-01 | 2011-12-07 | 北京弘祥隆生物技术开发有限公司 | Method for developing and utilizing overground and underground parts of astragalus comprehensively |
| US9869736B2 (en) | 2012-04-27 | 2018-01-16 | Siemens Aktiengesellschaft | Water/fat image identification method and device, and harmonization method and device |
| CN109497348A (en) * | 2018-11-21 | 2019-03-22 | 内江师范学院 | A kind of fish meal and preparation method thereof based on Astragalus Root P.E |
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| CN101003529B (en) * | 2007-01-17 | 2010-05-19 | 河南中医学院 | Method for separating component in flavonoid from root of large-flowered skullcap |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100348606C (en) * | 2005-07-08 | 2007-11-14 | 南京大学 | Preparation method of astilbin |
| CN101073592B (en) * | 2006-05-18 | 2011-08-10 | 天津天士力制药股份有限公司 | Method for separating and extracting Milkvetch Root |
| CN102060825A (en) * | 2009-11-13 | 2011-05-18 | 天津市食品研究所有限公司 | Method for extracting flavone from young barley grass |
| CN102188475A (en) * | 2011-06-21 | 2011-09-21 | 李宝生 | Application of total flavonoids of astragalus in preparing pharmaceutical for preventing and treating acute radiation pneumonitis |
| CN102188475B (en) * | 2011-06-21 | 2012-07-25 | 李宝生 | Application of total flavonoids of astragalus in preparing pharmaceutical for preventing and treating acute radiation pneumonitis |
| CN102266378A (en) * | 2011-08-01 | 2011-12-07 | 北京弘祥隆生物技术开发有限公司 | Method for developing and utilizing overground and underground parts of astragalus comprehensively |
| US9869736B2 (en) | 2012-04-27 | 2018-01-16 | Siemens Aktiengesellschaft | Water/fat image identification method and device, and harmonization method and device |
| CN109497348A (en) * | 2018-11-21 | 2019-03-22 | 内江师范学院 | A kind of fish meal and preparation method thereof based on Astragalus Root P.E |
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