CN102649808A - Method for separating ursolic acid from plantain herb - Google Patents
Method for separating ursolic acid from plantain herb Download PDFInfo
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- CN102649808A CN102649808A CN2012101203926A CN201210120392A CN102649808A CN 102649808 A CN102649808 A CN 102649808A CN 2012101203926 A CN2012101203926 A CN 2012101203926A CN 201210120392 A CN201210120392 A CN 201210120392A CN 102649808 A CN102649808 A CN 102649808A
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Abstract
The invention relates to a method for separating ursolic acid from plantain herb. The method comprises the following steps: extracting the crushed plantain herb by using low-carbon chain alcohol or solution thereof and recycling the solvent to obtain extractum; extracting the extractum by using a medium polar solvent and recycling to obtain a leaching matter; degreasing the leaching matter by using a low-polarity solvent, dissolving the leaching matter into the low-carbon chain alcohol and destaining by using active carbon; recycling the solvent to obtain a white ursolic acid crude product; and recrystallizing the ursolic acid crude product by using the low-carbon chain alcohol, low-carbon alcohol aqueous solution, ethyl acetate or a mixture thereof to obtain a ursolic acid crystal. The raw materials are readily available; the process is simple and practical; the obtained ursolic acid has high purity and is low in cost; and the method is very suitable for large-scale production.
Description
?
Technical field
The invention belongs to natural medicine field, be specifically related to the novel process of isolating active composition ursolic acid from psyllium.
Technical background
Ursolic acid (Ursolic acid) has another name called urson or ursonic acid, belongs to triterpene compound, and molecular formula is C
30H
18O
3, chemical name is 3 beta-hydroxies-black bearberry alkane-12-alkene-28-carboxylic acid.Ursolic acid has pharmaceutical use widely; As treat hepatic fibrosis, treatment amyotrophy, hypertension, atherosclerosis, effect such as anti-oxidant; And it has cell toxicant, induces differentiation and anti-angiogenic formation effect multiple carcinogenic cells; Its anti-cancer and kill cancer action draws attention, becomes the new focus of modern tumour medicine research, and ursolic acid also might become the potential drug of anti-HIV.
Psyllium has another name called wheel dish, pig Auricled Hedyotis Herb, cash strings grass, it is dead to step on, clam ant grass, wild beet, wheel dish etc., is the dry herb of (Plantago asiatica L.) or Plantago depressa Willd (Plantago depressa Willd.) before the Plantaginaceae plant car.Ursolic acid content is higher in the psyllium.Psyllium is abundant in china natural resources, and all there is distribution almost national each province, and it is rapid and cheap to grow, and this provides rich in natural resources for the development and use of psyllium.The raw materials used psyllium of the present invention is exactly the dry herb of psyllium.
Summary of the invention
The object of the invention is to provide a kind of novel method of from psyllium, separating ursolic acid.It is with the psyllium of pulverizing with low carbon chain alcohol or their extraction with aqueous solution, reclaim solvent and get medicinal extract; Medicinal extract extracts with medium polar solvent or extraction, reclaim the leaching thing; This leaching thing with the low polar solvent degreasing after, be dissolved in low carbon chain alcohol and also use activated carbon decolorizing; Reclaim solvent and obtain white ursolic acid bullion; The ursolic acid bullion gets the ursolic acid crystal behind low carbon chain alcohol, low carbon chain alcohol solution, ETHYLE ACETATE or their mixture recrystallizations.
The concrete step of this technology gathers as follows:
The psyllium of 1, learning from else's experience and pulverizing, by liquid-solid ratio mL/g 4/1～20/1 add low carbon chain alcohol be methyl alcohol or ethanol or they arbitrarily than mixture, or their aqueous solution; Volume by volume concentration 50%～100%, under 20-90 ℃, the UW of reflux or power 100～1000w or the microwave-assisted of 100～1000w power extract 1～3 time; Each 0.1～2 hour; Stirring velocity 0～2000r/min, united extraction liquid, normal pressure or decompression and solvent recovery get medicinal extract;
2, get medicinal extract; By liquid-solid ratio mL/g 10/1～100/1 add medium polar solvent methylene dichloride, trichloromethane, ethylene dichloride, ETHYLE ACETATE or they arbitrarily than mixture, under 20-70 ℃, the microwave-assisted of ultrasonic or power 100～1000w of heating and refluxing extraction or power 100～1000w extracts 1～3 time; Each 0.1～2 hour; Stirring velocity 0～2000r/min perhaps is scattered in medicinal extract in the water and extracts 1～3 time water and organic phase volume ratio 1/9～9/1 again with above-mentioned medium polar solvent; United extraction liquid or organic extract liquid, normal pressure or decompression and solvent recovery get medium polar solvent leaching thing;
3, get this medium polar solvent leaching thing, by liquid-solid ratio mL/g 10/1～100/1 add low polar solvent sherwood oil, normal hexane, hexanaphthene, normal heptane or they arbitrarily than mixture, under 20-90 ℃; The microwave of ultrasonic or power 100～1000w of reflux degreasing or power 100～1000w; Auxiliary degreasing 1～3 time, each 0.1～2 hour, stirring velocity 0～2000r/min; Filter or centrifugal, obtain medium polar solvent leaching thing after the degreasing;
4, by liquid-solid ratio mL/g 20/1～200/1 add low carbon chain alcohol be methyl alcohol or ethanol or theirs arbitrarily than mixture or their aqueous solution volume ratio concentration 50%～100%; Medium polar solvent leaching thing dissolves after making degreasing; Under 20-90 ℃; Add gac by 1/10～5/1 of leaching amount g/g, the microwave-assisted decolouring of the power of reflux or ultrasonic 100～1000w or power 100～1000w 1～5 time each 0.1～2 hour, stirring velocity 0～2000r/min; Filtration or centrifugal, normal pressure or decompression and solvent recovery obtain the ursolic acid bullion;
5, get the ursolic acid bullion; By liquid-solid ratio mL/g 20/1～300/1 add low carbon chain alcohol be methyl alcohol or ethanol or theirs arbitrarily than the mixture or their aqueous solution; The mixture of volume by volume concentration 50%～100% or ETHYLE ACETATE or ETHYLE ACETATE and low carbon chain alcohol; Volume ratio 1/9～9/1 is carried out crystallization or recrystallization, filters or the centrifugal ursolic acid crystal that obtains.
Advantage of the present invention is: compare with other plant material, the used psyllium of the present invention distributes extensively in China, is easy to cultivation, and growth is rapid, and this is to the invention provides abundant and inexpensive raw material; Industrial chemicals required for the present invention is easy to get, and can reclaim usefulness again, and therefore " three wastes " treatment capacity is little, and environment is not produced pollution basically; The present invention does not adopt column chromatography technology, but directly adopts technologies such as extraction, extraction, decolouring, crystallization, so easy, the required device of this technology is simple, is fit to very much large-scale production.To sum up state institute, raw material required for the present invention is cheap and easy to get, and environmental pollution is little, and technology is simple and easy to do, and production equipment is simple, so the present invention prepares the lower and very suitable large-scale production of the cost of ursolic acid.
Embodiment
Embodiment 1:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, with 8 times of amount 95% extraction using alcohols 3 times (each 2 hours, 70 ℃, stir rotating speed 800r/min), decompression recycling ethanol obtains Vandyke brown medicinal extract; Ethanol extraction is scattered in the water, gets isopyknic chloroform and extracts respectively 3 times, and the combined chloroform layer reclaims chloroform and obtains chloroform extract; Chloroform extract is sloughed fat-soluble component 3 times (each 1 hour, 60 ℃, stir rotating speed 500r/min) with the sherwood oil (boiling point 60-90 ℃) of 10 times of amounts; Chloroform extract after the degreasing is dissolved in 95% ethanol, adds activated carbon decolorizing 3 times (each 1 hour, 50 ℃, stir rotating speed 500r/min), filters, and merging filtrate reclaims ethanol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with 95% ethyl alcohol recrystallization.
Embodiment 2:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, with 6 times of amount dehydrated alcohol extraction 3 times (each 2 hours, 60 ℃, stir rotating speed 600r/min), decompression recycling ethanol obtains Vandyke brown medicinal extract; Ethanol extraction is scattered in the water, gets isopyknic methylene dichloride and extracts respectively 3 times, and the combined dichloromethane layer reclaims methylene dichloride and obtains dichloromethane extract; Dichloromethane extract is sloughed fat-soluble component 3 times (each 1 hour, 40 ℃, stir rotating speed 500r/min) with the normal hexane of 20 times of amounts; Dichloromethane extract after the degreasing is dissolved in the absolute ethyl alcohol, adds activated carbon decolorizing 3 times (each 1 hour, 60 ℃, stir rotating speed 400r/min), filters, and merging filtrate reclaims ethanol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with the absolute ethyl alcohol recrystallization.
Embodiment 3:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, with 6 times of amount methanol extraction 3 times (each 2 hours, 40 ℃, stir rotating speed 600r/min), reclaim under reduced pressure methyl alcohol obtains Vandyke brown medicinal extract; The methyl alcohol alcohol extract is scattered in the water, gets isopyknic ETHYLE ACETATE and extracts respectively 3 times, and the combined ethyl acetate layer reclaims ETHYLE ACETATE and obtains ethyl acetate extract; Ethyl acetate extract is sloughed fat-soluble component 3 times (each 1 hour, 50 ℃, stir rotating speed 500r/min) with the sherwood oil (boiling point 60-90 ℃) of 20 times of amounts; Ethyl acetate extract after the degreasing is dissolved in the absolute ethyl alcohol, adds activated carbon decolorizing 3 times (each 1 hour, 40 ℃, stir rotating speed 500r/min), filters, and merging filtrate reclaims ethanol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with re-crystallizing in ethyl acetate.
Embodiment 4:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, extract (each 2 hours, 40 ℃, stir rotating speed 600r/min) 3 times with 10 times of amount 60% aqueous ethanolic solutions, decompression and solvent recovery obtains Vandyke brown medicinal extract; Ethanol extraction is scattered in the water, gets isopyknic ETHYLE ACETATE and extracts respectively 3 times, and the combined ethyl acetate layer reclaims ETHYLE ACETATE and obtains ethyl acetate extract; Ethyl acetate extract is sloughed fat-soluble component 3 times (each 1 hour, 40 ℃, stir rotating speed 500r/min) with the normal hexane of 20 times of amounts; Normal hexane extract after the degreasing is dissolved in the methyl alcohol, adds activated carbon decolorizing 3 times (each 1 hour, 40 ℃, stir rotating speed 500r/min), filters, and merging filtrate reclaims methyl alcohol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with recrystallizing methanol.
Embodiment 5:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, with 12 times of amount 95% ethanol ultrasonic assisted extraction 3 times (each 0.5 hour) (can add temperature, rotating speed), decompression recycling ethanol obtains Vandyke brown medicinal extract; Ethanol extraction extracts respectively 3 times with 20 times methylene dichloride, and the combined dichloromethane layer reclaims methylene dichloride and obtains dichloromethane extract; Dichloromethane extract is sloughed fat-soluble component 2 times (each 30 hours, 50 ℃, stir rotating speed 500r/min) with the sherwood oil (boiling point 60-90 ℃) of 30 times of amounts; Dichloromethane extract after the degreasing is dissolved in the absolute ethyl alcohol, adds activated carbon decolorizing 3 times (each 1 hour, 50 ℃, stir rotating speed 600r/min), filters, and merging filtrate reclaims ethanol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with the mixture recrystallization of ethanol and ETHYLE ACETATE.
Embodiment 6:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, extract 3 times (each 0.2 hour) with 12 times of amount 95% ethanol microwave-assisted, decompression recycling ethanol obtains Vandyke brown medicinal extract; Ethanol extraction extracts respectively 3 times with 20 times chloroform, reclaims chloroform and obtains chloroform extract; Chloroform extract is sloughed fat-soluble component 2 times (each 0.5 hour, 50 ℃, stir rotating speed 500r/min) with the sherwood oil (boiling point 60-90 ℃) of 30 times of amounts; Chloroform extract after the degreasing is dissolved in the absolute ethyl alcohol, adds activated carbon decolorizing 3 times (each 1 hour, 50 ℃, stir rotating speed 600r/min), filters, and merging filtrate reclaims ethanol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with ethyl alcohol recrystallization.
Embodiment 7:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, adopt percolation (increasing amount), use 95% extraction using alcohol, decompression recycling ethanol obtains Vandyke brown medicinal extract; Ethanol extraction extracts respectively 3 times with 20 times ethylene dichloride, reclaims ethylene dichloride and obtains the ethylene dichloride extract; The ethylene dichloride extract is sloughed fat-soluble component 2 times (each 0.5 hour, 50 ℃, stir rotating speed 400r/min) with the sherwood oil (boiling point 60-90 ℃) of 20 times of amounts; Ethylene dichloride extract after the degreasing is dissolved in the methyl alcohol, adds activated carbon decolorizing 3 times (each 1 hour, 40 ℃, stir rotating speed 600r/min), and is centrifugal, merges clear liquid, reclaims methyl alcohol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with methyl alcohol and alcohol mixed solution recrystallization.
Embodiment 8:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, with 10 times of amount 95% ethanol ultrasonic assisted extraction 3 times (each 0.5 hour), decompression recycling ethanol obtains Vandyke brown medicinal extract; Ethanol extraction extracts respectively 3 times with 20 times ETHYLE ACETATE, reclaims ETHYLE ACETATE and obtains ethyl acetate extract; Ethyl acetate extract is sloughed fat-soluble component 3 times (each 0.3 hour, 40 ℃, stir rotating speed 500r/min) with the sherwood oil (boiling point 60-90 ℃) of 30 times of amounts; Ethyl acetate extract after the degreasing is dissolved in 95% ethanol, adds activated carbon decolorizing 3 times (each 0.5 hour, 60 ℃, stir rotating speed 400r/min), filters, and merging filtrate reclaims ethanol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with 95% ethyl alcohol recrystallization.
Embodiment 9:
With psyllium nature airing or oven dry, pulverize, get the psyllium fine powder, with 14 times of amount ethanol ultrasonic assisted extraction 3 times (each 0.2 hour), decompression recycling ethanol obtains Vandyke brown medicinal extract; Ethanol extraction extracts respectively 3 times with 20 times chloroform, reclaims chloroform and obtains chloroform extract; Chloroform extract is sloughed fat-soluble component 2 times (each 0.5 hour, 50 ℃, stir rotating speed 500r/min) with the cyclohexane of 30 times of amounts; Chloroform extract after the degreasing is dissolved in the methyl alcohol, adds activated carbon decolorizing 3 times (each 1 hour, 50 ℃, stir rotating speed 600r/min), filters, and merging filtrate reclaims methyl alcohol and obtains white ursolic acid bullion.The ursolic acid bullion obtains the ursolic acid crystal with recrystallizing methanol.
Claims (4)
1. method of from psyllium, separating ursolic acid is characterized in that:
The psyllium of (1) learning from else's experience and pulverizing adds the low carbon chain alcohol or their aqueous solution, volume by volume concentration 50%～100% by liquid-solid ratio mL/g 4/1～20/1; Under 20-90 ℃; The microwave-assisted of the UW of reflux or power 100～1000w or 100～1000w power extracts 1～3 time, and each 0.1～2 hour, stirring velocity 0～2000r/min; United extraction liquid, normal pressure or decompression and solvent recovery get medicinal extract;
(2) get medicinal extract; Add medium polar solvent by liquid-solid ratio mL/g 10/1～100/1, under 20-70 ℃, the microwave-assisted of ultrasonic or power 100～1000w of heating and refluxing extraction or power 100～1000w extracts 1～3 time; Each 0.1～2 hour; Stirring velocity 0～2000r/min perhaps is scattered in medicinal extract in the water and extracts 1～3 time water and organic phase volume ratio 1/9～9/1 again with above-mentioned medium polar solvent; United extraction liquid or organic extract liquid, normal pressure or decompression and solvent recovery get medium polar solvent leaching thing;
(3) get this medium polar solvent leaching thing, add low polar solvent by liquid-solid ratio mL/g 10/1～100/1, under 20-90 ℃; The microwave of ultrasonic or power 100～1000w of reflux degreasing or power 100～1000w; Auxiliary degreasing 1～3 time, each 0.1～2 hour, stirring velocity 0～2000r/min; Filter or centrifugal, obtain medium polar solvent leaching thing after the degreasing;
(4) add the low carbon chain alcohol or their aqueous solution by liquid-solid ratio mL/g 20/1～200/1; Volume by volume concentration 50%～100%; Medium polar solvent leaching thing dissolves after making degreasing, under 20-90 ℃, adds gac by 1/10～5/1 of leaching amount g/g; The microwave-assisted of the power of reflux or ultrasonic 100～1000w or power 100～1000w decolouring 1～5 time is each 0.1～2 hour; Stirring velocity 0～2000r/min, filtration or centrifugal, normal pressure or decompression and solvent recovery obtain the ursolic acid bullion;
(5) get the ursolic acid bullion; Add the low carbon chain alcohol or their aqueous solution by liquid-solid ratio mL/g 20/1～300/1; The mixture of volume by volume concentration 50%～100% or ETHYLE ACETATE or ETHYLE ACETATE and low carbon chain alcohol; Volume ratio 1/9～9/1 is carried out crystallization or recrystallization, filters or the centrifugal ursolic acid crystal that obtains.
2. a kind of method of from psyllium, separating ursolic acid according to claim 1 is characterized in that: said low carbon chain alcohol is a kind of than in the mixture arbitrarily of methyl alcohol, ethanol and they.
3. a kind of method of from psyllium, separating ursolic acid according to claim 1 is characterized in that: said medium polar solvent is a kind of than in the mixture arbitrarily of methylene dichloride, trichloromethane, ethylene dichloride, ETHYLE ACETATE and they.
4. a kind of method of from psyllium, separating ursolic acid according to claim 1 is characterized in that: said low polar solvent is a kind of than in the mixture arbitrarily of sherwood oil, normal hexane, hexanaphthene, normal heptane and they.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103204895A (en) * | 2013-04-08 | 2013-07-17 | 南昌大学 | Method for separating ursolic acid from apple peel |
| CN103694304A (en) * | 2013-12-28 | 2014-04-02 | 湘西自治州奥瑞克医药化工有限责任公司 | Production process for producing high-purity ursolic acid |
| CN108690115A (en) * | 2018-05-28 | 2018-10-23 | 吉林农业科技学院 | The Microwave Extraction technique of ursolic acid in a kind of Asiatic plantain |
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| CN1763072A (en) * | 2004-06-29 | 2006-04-26 | 浙江大学 | Process for extracting active component ursolic acid from persimmon leaf |
| CN101037467A (en) * | 2007-04-10 | 2007-09-19 | 福州大学 | Method for separating purifying ursolic acid from loquat leaf |
| CN101417014A (en) * | 2007-10-23 | 2009-04-29 | 北京亚东生物制药有限公司 | Traditional Chinese medicine composition for treating stramgutia and preparation method and quality control method thereof |
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| CN1763072A (en) * | 2004-06-29 | 2006-04-26 | 浙江大学 | Process for extracting active component ursolic acid from persimmon leaf |
| CN101037467A (en) * | 2007-04-10 | 2007-09-19 | 福州大学 | Method for separating purifying ursolic acid from loquat leaf |
| CN101417014A (en) * | 2007-10-23 | 2009-04-29 | 北京亚东生物制药有限公司 | Traditional Chinese medicine composition for treating stramgutia and preparation method and quality control method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103204895A (en) * | 2013-04-08 | 2013-07-17 | 南昌大学 | Method for separating ursolic acid from apple peel |
| CN103204895B (en) * | 2013-04-08 | 2015-08-12 | 南昌大学 | A kind of method of separating ursolic acid from Pericarpium Mali pumilae |
| CN103694304A (en) * | 2013-12-28 | 2014-04-02 | 湘西自治州奥瑞克医药化工有限责任公司 | Production process for producing high-purity ursolic acid |
| CN108690115A (en) * | 2018-05-28 | 2018-10-23 | 吉林农业科技学院 | The Microwave Extraction technique of ursolic acid in a kind of Asiatic plantain |
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Application publication date: 20120829 |