CN1923844A - Process for producing ursolic acid - Google Patents
Process for producing ursolic acid Download PDFInfo
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- CN1923844A CN1923844A CN 200610048656 CN200610048656A CN1923844A CN 1923844 A CN1923844 A CN 1923844A CN 200610048656 CN200610048656 CN 200610048656 CN 200610048656 A CN200610048656 A CN 200610048656A CN 1923844 A CN1923844 A CN 1923844A
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Abstract
The invention discloses a preparing method of ursolic acid, which comprises the following steps: extracting; separating; purifying; selecting carbohydrate gum leaf as raw material; boiling to remove soluble impurity; adding alcohol; extracting through heat for 2-4 times; combining the extract; recycling solvent to obtain concrete; adding acid water to dissolve; stirring completely; separating acid water and sediment; adding alcohol in the sediment to dissolve; crystallizing at low temperature; recrystallizing for many times to obtain different purity products.
Description
Technical field: the present invention relates to a kind of preparation method of ursolic acid, relate in particular to a kind of method by separating and preparing ursolic acid in the carbohydrate gum leaf (Alstonia scholaris).
Background technology: ursolic acid (Ursolic acid) has another name called urson, is pentacyclic triterpenoid, molecular formula C30H48O3, molecular weight 456.Be a kind of triterpene compound that is present in the natural phant, have anti-hepatitis, antitumor, AIDS virus resisting, antisepsis and anti-inflammation, calmness, anti-diabetic, antiulcer agent, etc. the various biological effect.Discovered in recent years, ursolic acid have carcinogenesis, anti-promoting, induce differentiation of F9 teratocarcinoma cell and blood vessel formation against function, very likely become low toxicity new type anticancer and Antihepatitis medicament efficiently.Have important use at aspects such as medicines and health protection, daily-use chemical industry, functional food, become the focus of domestic and international research and development.Because it is pharmacologically active widely, few side effects, toxicity is low, in recent years both at home and abroad to its extraction, assay, number of research projects has been carried out in the pharmacological action aspect, ursolic acid is distributed more widely in vegitabilia, according to incompletely statistics, in existing 34 sections of nature 108 kind of plant, separate and obtain ursolic acid, the distribution of ursolic acid in plant is very wide, different sorts plant ursolic acid content is widely different, mainly be distributed in Glossy Privet Fruit, hawthorn, Agkistrodon, the tongue grass, Sambucus chinensis, Spica Prunellae and skunk bush, leaf of chinese photinia, leaf of Turpinia pomifera (Roxb) D O., in the plants such as cynomorium songaricum, with free form or be combined into glucosides and exist.The content of ursolic acid in above-mentioned plant is respectively 0.29%, 0.46%, 0.38%, 0.42%, 0.35% and 0.21%, 0.41%, 0.0188%, 0.0247%, 0.78%.0.78%; Ji is far away produce complete stool in the narrow baseline Herba Rabdosiae glaucocalycis, and stem in contained ursolic acid be respectively 0.7112%, 1.3634%, 0.4296%, deseed FRUCTUS FORSYTHIAE, Folium Forsythiae, golden bell core ursolic acid content are respectively 0.765%, 1.302%, 0.352%, and ursolic acid content is respectively 0.414% and 0.573% in Rabdosia rubescens herb and the leaf.Existing Chinese patent application provides the method for extracting ursolic acid from plant Loquat Leaf (seeing CN200310122716.0), rhododendron leaves (CN1569885 is open), persimmon leaf (CN200410025770.8 is open), Leaf of Glossy Privet (CN200310111479.8 and CN01138325.9 are open), Folium paulowniae (CN03108037.5 is open), Leaf of Chinese Holly (CN1508149 is open).Ursolic acid content is low in the material plant that these methods are chosen, and all is lower than 1%, and complex process, the cost height, and the product yield is low.
Summary of the invention: at the above-mentioned problems in the prior art, the purpose of this invention is to provide a kind of method by separating and preparing ursolic acid in the carbohydrate gum leaf, ursolic acid content in the selected raw material of this method is higher than in the prior art all as the vegetable drug of the raw material of producing ursolic acid, and this method is water and alcohol other solvent in addition not, technology is simple, with low cost, product yield height is suitable for industrial production.
In order to realize above-mentioned purpose of the present invention, the invention provides following technical scheme:
A kind of preparation method of ursolic acid comprises extraction, separation, purification step, and choosing the carbohydrate gum leaf is raw material, add alcohol, heat is extracted 2-4 time, and united extraction liquid reclaims solvent and gets medicinal extract, add the sour water dissolving then, fully stir, separate aqueous acid and precipitation, get the precipitation part, add dissolve with ethanol, precipitated crystal gets final product in the low temperature.
Among the above-mentioned preparation method, extraction step preferably with the carbohydrate gum leaf pulverized with 1: 3-10 times of V/V industrial alcohol refluxing extraction 4 times, reflux 1-2 hour at every turn.
Separating step preferably adds 0.2-2% hydrochloric acid or sulfuric acid or phosphate aqueous solution and soaks 4 times in medicinal extract, fully stir, and merges the sour water layer, separates aqueous acid and precipitation.
The solution that purification step preferably precipitates after being partly dissolved is placed in 0-5 ℃ of low temperature, carries out precipitated crystal, and can carry out repeatedly recrystallization.
Preferred step be before the common alstonia leaf raw material is carried out ethanol-extracted earlier with the raw material poach to removing water-soluble impurity.
The concrete method of the present invention is: extracting and choosing the carbohydrate gum leaf is raw material, the carbohydrate gum leaf of pulverizing is used earlier poach, after removing water-soluble impurity, with 1: 3-10 times of V/V industrial alcohol refluxing extraction 2-4 time, each reflux 1-2 hour, united extraction liquid, reclaim solvent and get medicinal extract, separation is to add the 0.2-2% aqueous hydrochloric acid to soak 4 times in medicinal extract, fully stir, merge the sour water layer, separate aqueous acid and precipitation, purifying is that the solution add dissolve with ethanol in the precipitation part that separating step obtains after is placed in 0-5 ℃ of low temperature, carries out repeatedly recrystallization.
Technical scheme of the present invention is based on for a long time to be developed the research of different sorts plant ursolic acid content and production method.Ursolic acid content is higher than in the present prior art all and is used as the plant material of producing ursolic acid in the raw material carbohydrate gum leaf of the production ursolic acid that the present invention is selected, and content of ursolic acid is between 2.6-3.3% in the carbohydrate gum leaf.Common alstonia (Alstoniascholaris (L.) R.Br.) belongs to Apocynaceae (Apocynaceae) alstonia yonnanensis platymiscium, the another name Cornus controversa.In Xishuangbanna, Yunnan area the Dai nationality as antitussive and widespread use.Folium Alstoniae Scholaris once recorded in local medicine will as " Luchuan book on Chinese herbal medicine ", " choosing of Yunnan herbal medicine " in, and recorded by " Yunnan Province's drug standard " (1974) and the Pharmacopoeia of the People's Republic of China (version was one one in 1977).Folium Alstoniae Scholaris " but clearing heat, eliminating phlegm, relieving cough is used for the cough due to the accumulation of phlegm-heat in the lung, coughs up phlegm, and chronic bronchitis, Whooping cough is seen above-mentioned patient ".
Compared with prior art, excellent beneficial effect of the present invention is:
1. the raw material of the selected production ursolic acid of the present invention is the carbohydrate gum leaf, and the content of ursolic acid in the carbohydrate gum leaf is higher than that all are as plant materials that ursolic acid is produced at present, and content is between 2.6-3.3%.The purity of the ursolic acid of extraction separation is between 30-98% from the carbohydrate gum leaf.
2. other organic solvent beyond water and the ethanol not in the method for from the carbohydrate gum leaf, extracting ursolic acid provided by the invention, for the industrial production ursolic acid provides a kind of technology simple, with low cost, the method that ursolic acid product yield is high.
Description of drawings:
Fig. 1 is 32% ursolic acid HPLC collection of illustrative plates for purity;
Fig. 2 is 53% ursolic acid HPLC collection of illustrative plates for purity;
Fig. 3 is 98% ursolic acid HPLC collection of illustrative plates for purity.
Embodiment:
Below in conjunction with accompanying drawing, further specify essentiality content of the present invention with embodiments of the invention, but do not limit the present invention with this.
Embodiment 1:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, with the carbohydrate gum leaf 1kg that pulverizes with 1: 3 times of V/V industrial alcohol refluxing extraction 3 times, each reflux 2 hours, united extraction liquid, the recovery solvent obtains carbohydrate gum leaf medicinal extract 230g.Add 0.2% aqueous hydrochloric acid and dissolve in medicinal extract, fully stir, separate aqueous acid and precipitation, shared 0.2% aqueous hydrochloric acid soaks 4 times, merges the sour water layer, is precipitated as ursolic acid crude product 96g.Add ethanol 2L in the precipitation that obtains and dissolve, solution is positioned in 0 ℃ of low temperature and carries out precipitated crystal, and primary crystallization can get the 81g ursolic acid, repeatedly gets purity behind the recrystallization and reaches 98% ursolic acid.
The ursolic acid finished product that obtains is detected used instrument, condition and result:
Instrument: Waters Alliance 2695 type high performance liquid chromatographs, 2996 type DAD penetrate detector.
Chromatographic condition: chromatographic column: Xtrra C18 post (4.6mm * 250mm, 5 μ m); Moving phase: CH
3CN-0.5%H
3PO
4The aqueous solution (80: 20); Flow velocity: 1.0ml/min; Column temperature: 35 ℃;
Through the content detection of HPLC, analyze content of ursolic acid in the scope of 30-98%.It is 42% ursolic acid that primary crystallization gets purity, repeatedly behind the recrystallization purity reach 98% ursolic acid.
Embodiment 2:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, with the carbohydrate gum leaf 1kg that pulverizes with 1: 4 times of (V/V) industrial alcohol refluxing extraction 4 times, each reflux 1.5 hours, united extraction liquid, the recovery solvent obtains carbohydrate gum leaf medicinal extract 228g.Add 2% aqueous sulfuric acid 2L and dissolve in medicinal extract, fully stir, shared 2% aqueous sulfuric acid of medicinal extract soaks 4 times, separates aqueous acid and precipitation.Be precipitated as ursolic acid crude product 90g.Add ethanol 2L in the precipitation and dissolve, solution is positioned over 5 ℃ and carries out precipitated crystal, and through the content detection of HPLC, primary crystallization can get 41% ursolic acid 78g, repeatedly gets purity behind the recrystallization and reaches 98% ursolic acid.
Embodiment 3:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, the carbohydrate gum leaf poach that the carbohydrate gum leaf 1kg that pulverizes is pulverized 3 times, each 1 hour, after removing water-soluble impurity, with 1: 10 times of (V/V) industrial alcohol refluxing extraction 3 times, each reflux 1 hour, united extraction liquid reclaims solvent and obtains carbohydrate gum leaf medicinal extract 220g.Add 2% aqueous hydrochloric acid 2L and dissolve in medicinal extract, fully stir, shared 2% aqueous hydrochloric acid of medicinal extract soaks 4 times, separates aqueous acid and precipitation.Be precipitated as ursolic acid crude product 88g.Add ethanol 2L in the precipitation and dissolve, solution is positioned over 5 ℃ and carries out precipitated crystal, and through the content detection of HPLC, primary crystallization can get 52g ursolic acid crude product, and repeatedly recrystallization can obtain purity＞98% ursolic acid.
Embodiment 4:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, the carbohydrate gum leaf poach that the carbohydrate gum leaf 1kg that pulverizes is pulverized 2 times, each 2 hours, after removing water-soluble impurity, extract 4 times with 1: 5 times of (V/V) methanol eddy, each reflux 2 hours, united extraction liquid reclaims solvent and obtains carbohydrate gum leaf medicinal extract 232g.Add 1.5% aqueous hydrochloric acid 2L and dissolve in medicinal extract, fully stir, shared 1.5% aqueous hydrochloric acid of medicinal extract soaks 4 times, separates aqueous acid and precipitation.Be precipitated as ursolic acid crude product 78g.Add ethanol 2L in the precipitation and dissolve, solution is positioned over 3 ℃ and carries out precipitated crystal, and through the content detection of HPLC, primary crystallization can get 48g ursolic acid crude product, and repeatedly recrystallization can obtain purity＞98% ursolic acid.
Embodiment 5:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, the carbohydrate gum leaf poach that the carbohydrate gum leaf 1kg that pulverizes is pulverized 3 times, each 1 hour, after removing water-soluble impurity, extract 4 times with 1: 8 times of (V/V) methanol eddy, each reflux 2 hours, united extraction liquid reclaims solvent and obtains carbohydrate gum leaf medicinal extract 236g.Add 1% aqueous sulfuric acid 2L and dissolve in medicinal extract, fully stir, shared 1% aqueous sulfuric acid of medicinal extract soaks 4 times, separates aqueous acid and precipitation.Be precipitated as ursolic acid crude product 82g, add ethanol 2L in the precipitation and dissolve, solution is positioned over 5 ℃ and carries out precipitated crystal, and through the content detection of HPLC, primary crystallization can get the 46g ursolic acid, and repeatedly recrystallization can obtain purity＞98% ursolic acid finished product.
Embodiment 6:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, with the carbohydrate gum leaf 1kg poach pulverized 2 times, and each 2 hours, extract 4 times with 1: 5 times of (V/V) methanol eddy, each reflux 1.5 hours, united extraction liquid reclaims solvent and obtains carbohydrate gum leaf medicinal extract 238g.Add 2% phosphate aqueous solution 2L and dissolve in medicinal extract, fully stir, shared 2% phosphate aqueous solution of medicinal extract soaks 4 times, separates aqueous acid and precipitation.Be precipitated as ursolic acid crude product 80g, add ethanol 2L in the precipitation and dissolve, solution is positioned over 0 ℃ and carries out precipitated crystal, and through the content detection of HPLC, primary crystallization can get the 70g ursolic acid, and repeatedly recrystallization can obtain purity＞98% ursolic acid finished product.
Embodiment 7:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, with the carbohydrate gum leaf 1kg poach pulverized 3 times, and each 1 hour, use 1: 4 times of (V/V) methanol eddy to extract again 4 times, each reflux 2 hours, united extraction liquid reclaims solvent and obtains carbohydrate gum leaf medicinal extract 236g.Add 2% aqueous sulfuric acid 2L and dissolve in medicinal extract, fully stir, shared 2% aqueous sulfuric acid of medicinal extract soaks 4 times, separates aqueous acid and precipitation.Be precipitated as ursolic acid crude product 79g, add ethanol 2L in the precipitation and dissolve, solution is positioned over 1 ℃ and carries out precipitated crystal, and through the content detection of HPLC, primary crystallization can get purity and reach 53% ursolic acid, and repeatedly recrystallization can obtain purity＞98% ursolic acid.
Embodiment 8:
Getting carbohydrate gum leaf (Alstonia scholaris) is raw material, with the carbohydrate gum leaf 1kg poach pulverized 3 times, and each 1 hour, with 1: 9 times of (V/V) industrial alcohol refluxing extraction 2 times, each reflux 2 hours, united extraction liquid reclaims solvent and obtains carbohydrate gum leaf medicinal extract 230g.
Add 2% aqueous hydrochloric acid 2L and dissolve in medicinal extract, fully stir, shared 2% aqueous hydrochloric acid of medicinal extract soaks 3 times, separates aqueous acid and precipitation.Be precipitated as ursolic acid crude product 86g, add ethanol 2L in the precipitation and dissolve, solution is positioned over 4 ℃ and carries out precipitated crystal, and through the content detection of HPLC, primary crystallization can get and can obtain 50% ursolic acid, and repeatedly recrystallization can obtain purity＞98% ursolic acid.
Claims (7)
1, a kind of preparation method of ursolic acid comprises extraction, separation, purification step, and it is characterized in that choosing the carbohydrate gum leaf is raw material, add alcohol, heat is extracted 2-4 time, and united extraction liquid reclaims solvent and gets medicinal extract, add the sour water dissolving then, fully stir, separate aqueous acid and precipitation, get the precipitation part, add dissolve with ethanol, precipitated crystal gets final product in the low temperature.
2, method according to claim 1, the carbohydrate gum leaf that it is characterized in that pulverizing is with 1: 3-10 times of V/V industrial alcohol heating and refluxing extraction 4 times, 1-2 hour at every turn.
3, method according to claim 1 is characterized in that adding 0.2-2% hydrochloric acid, sulfuric acid or phosphate aqueous solution immersion and dissolves for 4 times in medicinal extract.
4, method according to claim 1, the solution that it is characterized in that precipitating after being partly dissolved is placed in 0-5 ℃ of low temperature, carries out precipitated crystal.
5, method according to claim 1 is characterized in that precipitated crystal can carry out repeatedly recrystallization.
6, method according to claim 1, it is characterized in that before ethanol-extracted can be earlier with carbohydrate gum leaf poach to removing water-soluble impurity.
7, according to claim 1 or 2 or 3 or 4 or 5 or 6 described preparation method of ursolic acid, it is characterized in that it is raw material that the carbohydrate gum leaf is chosen in extraction, pulverize, poach, use 1 again: 3-10 times of V/V industrial alcohol heating and refluxing extraction 2-4 time, each 1-2 hour, united extraction liquid, reclaim solvent and get medicinal extract, separation is to add 0.2-2% hydrochloric acid in medicinal extract, sulfuric acid or phosphate aqueous solution soak 4 times, fully stir, merge the sour water layer, separate aqueous acid and precipitation, purifying is that the solution add dissolve with ethanol in the precipitation part that separating step obtains after is placed in 0-5 ℃ of low temperature, carries out the one or many recrystallization.
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| CNB2006100486566A CN100526327C (en) | 2006-09-05 | 2006-09-05 | Process for producing ursolic acid |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101643492B (en) * | 2009-08-21 | 2011-06-08 | 山东省中医药研究院 | Method for extracting and preparing ursolic acid from uncaria |
| CN101544679B (en) * | 2008-03-25 | 2011-06-08 | 河南大学 | Method for extracting ursolic acid from vegetable Dian clove |
| US8748658B2 (en) | 2010-03-22 | 2014-06-10 | Council Of Scientific And Industrial Research | Fast isolation method for the natural scaffold ursolic acid from Diospyros melanoxylon |
| CN110551168A (en) * | 2019-07-19 | 2019-12-10 | 湖南先伟实业有限公司 | method for separating and purifying ursolic acid from rosemary |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1128625C (en) * | 2000-08-23 | 2003-11-26 | 云南医药工业股份有限公司 | Dengtai tree extract and its preparation and use |
| CN1152034C (en) * | 2001-10-24 | 2004-06-02 | 太平保健药业（蛇口）有限公司 | Process for extracting active anticancer component from vinca flower |
-
2006
- 2006-09-05 CN CNB2006100486566A patent/CN100526327C/en active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101544679B (en) * | 2008-03-25 | 2011-06-08 | 河南大学 | Method for extracting ursolic acid from vegetable Dian clove |
| CN101643492B (en) * | 2009-08-21 | 2011-06-08 | 山东省中医药研究院 | Method for extracting and preparing ursolic acid from uncaria |
| US8748658B2 (en) | 2010-03-22 | 2014-06-10 | Council Of Scientific And Industrial Research | Fast isolation method for the natural scaffold ursolic acid from Diospyros melanoxylon |
| CN110551168A (en) * | 2019-07-19 | 2019-12-10 | 湖南先伟实业有限公司 | method for separating and purifying ursolic acid from rosemary |
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Effective date of registration: 20190711 Address after: 727000 South Industrial Park, Tongchuan New District, Shaanxi Province, Xingye Six Road (Yao Wang Da Health Industrial Incubation Park) Co-patentee after: Kunming Institute of Botany, Chinese Academy of Sciences Patentee after: Shaanxi Xinfenghe Pharmaceutical Co., Ltd. Address before: 650204 No. 610, Longquan Road, Kunming, Yunnan Patentee before: Kunming Institute of Botany, Chinese Academy of Sciences |