CN102127140A - Method for combinedly extracting Morroniside, dogwood polysaccharide and ursolic acid from dogwood - Google Patents
Method for combinedly extracting Morroniside, dogwood polysaccharide and ursolic acid from dogwood Download PDFInfo
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- CN102127140A CN102127140A CN2010105581332A CN201010558133A CN102127140A CN 102127140 A CN102127140 A CN 102127140A CN 2010105581332 A CN2010105581332 A CN 2010105581332A CN 201010558133 A CN201010558133 A CN 201010558133A CN 102127140 A CN102127140 A CN 102127140A
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Abstract
The invention relates to a method for combinedly extracting Morroniside, dogwood polysaccharide and ursolic acid from dogwood. The method comprises the following steps of: crushing the dogwood; adding water in an amount which is 10 to 15 times of the weight of the dogwood and performing heating extraction for 2 to 3 times; mixing the extracting liquid; loading the extracting liquid to a macroporous resin column I for adsorption; collecting liquid which flows down the column; eluting by using water and ethanol solution sequentially; mixing the water eluent with the liquid which flows down the column; adding alcohol for precipitation; filtering precipitates out and drying to obtain the dogwood polysaccharide; collecting the alcohol eluent, concentrating until alcohol does not exist, adding water for dispersion, adding isometric n-butyl alcohol for extraction, concentrating an n-butyl alcohol layer to recover the n-butyl alcohol, and drying to obtain the Morroniside; adding alcohol into the residues obtained after water extraction to perform reflux extraction, concentrating the extracting liquid, loading the extracting liquid to a macroporous resin column II for adsorption, eluting by using 90 percent ethanol; and adding active carbon into the eluent to perform reflux decoloring, filtering the active carbon out, cooling naturally for crystallization, filtering out crystals, and drying to obtain the ursolic acid. In the method, toxic reagents do not exist in the preparation process; the process is simple; the utilization ratio of the raw materials is high; cost is low; and the method is suitable for industrialized production.
Description
Technical field:
The invention belongs to the Separation of Natural Products field, especially a kind of method of extracting morroniside, skunk bush polysaccharide and ursolic acid of from skunk bush, uniting.
Background technology:
Skunk bush (Fructus Corni) is the dry pulp of Cornaceae plant skunk bush Cornus Officinalis Sieb.et Zucc., has another name called Fructus Corni, medicine jujube, meat jujube etc.Be a kind of nourishing class rare medicinal herbs, have tonify the liver and kidney, effect that puckery essence is taken off admittedly.Recent study shows, skunk bush has anti-hemorrhagic shock, anticoagulant, immunomodulatory, anti-inflammatory, effect such as hypoglycemic, anti-oxidant, anticancer, antibiotic.Skunk bush mainly contains compositions such as iridoid glycoside, polysaccharide, organic acid, tannin.Iridoids morroniside in the skunk bush is the highest with morroniside content.
China just has skunk bush to be applied to the record of diabetes (traditional Chinese medical science claims " diabetes ") treatment from ancient times, the present pharmaceutical research of lot of domestic and foreign shows, skunk bush iridoid glycosides material is the main reactive site of hypoglycemic, and Xu Huiqin etc. have studied the provide protection that the skunk bush iridoid glycoside becomes experiment type diabetic nephropathy; Pi Wenxia etc. " extraction process of the anti-ageing efficient part of the preferred skunk bush of Orthogonal Method " show the skunk bush iridoid glycosides except have hypoglycemic and the anti-diabetic complication, also have anti-aging effects.Document " progress of skunk bush active chemical (Zhou Jinghua; Li Chunsheng, Li Diandong. Chinese Journal of New Drugs, 2001; 10 (11): 808.) " and " chemical research of skunk bush polysaccharide (Yang Yun; Liu Jianxin, Liu Cuiping, etc. CHINA JOURNAL OF CHINESE MATERIA MEDICA; 1999; 24 (10): 614.) ", clinical study proves that skunk bush is the main Chinese medicinal materials of treatment diabetes, coronary heart disease and essential hypertension.Modern study shows that main component has carbohydrate, organic acid and ester class, tannin class etc. in the skunk bush pulp, wherein polysaccharose substance is the indispensable important substance of life metabolism, have multiple biological activity, skunk bush polysaccharide has immunoregulatory activity and tangible antioxygenation.Ursolic acid is a kind of pentacyclic triterpene acid of low-pole, has obvious anti-inflammatory and anti, lipopenicillinase, falls enzyme and antitumous effect, and be newfound in recent years anticancer active constituent, also be the new focus of modern tumor drug screening.
Existing morroniside separation method mostly adopts water extract-alcohol precipitation and macroporous resin column absorption.As patent " preparation method of Fructus Corni extract morroniside and purposes " (application number is 200410014771.2), the method of this patent disclosure is a skunk bush medicinal material extraction using alcohol, concentrating under reduced pressure, the concentrated solution aqueous precipitation, supernatant liquor carries out column chromatography with macroporous adsorbent resin or gac, water and rare pure flush away impurity, use ethanol elution again, collect elutriant, after concentrating under reduced pressure and the drying, obtain Powdered Fructus Corni extract morroniside through the reverse phase silica gel separation, this method water and rare pure wash-out impurity are used ethanol elution effective constituent, products obtained therefrom purity height again, but loss of effective components is more, thereby has reduced extraction yield.Patent " preparation method of morroniside and new purposes thereof " (application number is 200710113824.X), the preparation method of this patent disclosure is with skunk bush medicinal material water extract-alcohol precipitation, precipitation solution is transferred macroporous resin on twice of the pH to 1-3, water and low-concentration ethanol wash-out, elutriant low-temperature reduced-pressure drying, crystallization promptly gets product, though this method is simple to operate, precipitation solution need add acid and transfer pH, and morroniside belongs to iridoid glycosides, responsive to acid, structure easily changes.
The extracting method of relevant skunk bush polysaccharide reports that seldom method is relatively limited to.Existing method is that raw material degreasing, water are carried, concentrated, washing, drying, obtains product, and as " skunk bush polysaccharide extraction process and physico-chemical property researchs " such as Zhao Xiaohua, sherwood oil is used in degreasing, and consumption is big, toxicity is big; The used organic solvent kind of technology is many, causes effective constituent to run off easily.Zhang Lijuan etc. " the extraction process optimization of skunk bush polysaccharide reaches the cerebral ischemia re-pouring injured provide protection of the local kitchen range of rat "; document disclosed method is that ultrasonic water is carried, concentrated, ultrafiltration, alcohol precipitation, remove albumen, the washing drying obtains skunk bush polysaccharide; the polysaccharide concentrated solution is denseer thick; ultra-filtration membrane is easily stifled; operation is difficulty, and products obtained therefrom purity is not high.Chinese patent " a kind of method of extracting skunk bush polysaccharide by zymohydrolysis " (application number: 200810120569.6), the method of this patent disclosure is to get the broken skunk bush dry powder that makes of skunk bush dried fruit digested tankage, add-on is the distilled water of 15～60 times of amounts of skunk bush dry powder, add enzyme in 35～60 ℃, pH3.5～7.0 time enzymolysis 0.5h～4h, enzyme goes out after enzymolysis finishes, extracting solution concentrates alcohol precipitation, centrifugal drying promptly gets the skunk bush polysaccharide extract, under acidic conditions, may cause the fracture of glycosidic link in the polysaccharide, influence product purity and activity.
At present, the extraction separation of ursolic acid mainly adopts the method for organic solvent extraction and silica gel column chromatography stepwise elution, and the technical process of these methods is long, and yield is low, and uses poisonous organic solvent.In recent years, macroporous adsorbent resin demonstrates more and more important effect in extract drugs is separated, especially nonpolar or low-pole compound are had the good adsorption separation performance, therefore, the present invention adopts macroporous adsorbent resin that the ursolic acid in the skunk bush is separated.
Summary of the invention:
The technical problem to be solved in the present invention provides a kind of method of extracting morroniside, skunk bush polysaccharide and ursolic acid of uniting cheaply from skunk bush.
The present invention realizes by the following technical solutions:
A kind of method of extracting morroniside, skunk bush polysaccharide and ursolic acid of uniting from skunk bush is characterized in that comprising following steps:
1) extract: skunk bush is pulverized, added 10-15 times of water gaging heating and extract 2-3 time, united extraction liquid, the residue after water is carried add 6-8 and doubly measure the extraction of 90% alcohol reflux, and extracting solution concentrates;
2) macroporous resin column I absorption: above-mentioned aqueous extract is added macroporous resin column I absorption, collect lower column liquid, water and ethanolic soln wash-out merge water elution liquid and lower column liquid successively, add the alcohol precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide, collect alcohol eluen, concentrating does not have alcohol, add water-dispersion, add isopyknic n-butanol extraction 2-4 time, butanol extraction liquid concentrates and reclaims propyl carbinol, is drying to obtain morroniside;
3) macroporous resin column II absorption: macroporous resin column II absorption on the above-mentioned alcohol extracting concentrated solution, use 90% ethanol elution, collect elutriant, elutriant adds the gac reflux decolour, and the filtering gac is put cold crystallization, leaches crystallization, is drying to obtain ursolic acid.
Heating temperature is 40-65 ℃ in the step 1), extraction time 2-3 hour.
Step 2) a kind of among the optional HPD100 of macroporous resin I, LSA-20 in and the D101, the used alcohol of wash-out is 70% ethanolic soln.
A kind of among the optional X-5 of macroporous resin II, LSA-20 in the step 3) and the SPD-700.
Gac in the step 3) is a medical injection class gac, and add-on is the 0.5-1% of amount of liquid.
In sum, positively effect of the present invention is: the production range of product is many, quality good, the raw material availability height, and the economic benefit height is an environment-friendly type technique etc.This technology is suitable for middle-size and small-size chemical enterprise industrialization promotion and uses.
Further specify the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to following embodiment.
Embodiment:
Embodiment 1:
Skunk bush is pulverized, got 1kg, add 10L water and be heated to 50 ℃, soak and extracted 3 hours, extract united extraction liquid 2 times, add the absorption of HPD100 macroporous resin column, collect lower column liquid, use earlier the 3L water elution, water elution liquid and lower column liquid are merged, and adding ethanol to concentration is 70%, precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide 13.6g, content is 74.9%, and 3L70% ethanolic soln wash-out is collected alcohol eluen again, concentrate and do not have alcohol, add the 300ml water-dispersion, add isopyknic n-butanol extraction 3 times, butanol extraction liquid concentrates and reclaims propyl carbinol, be drying to obtain morroniside 8.9g, content is 71.2%, and the residue of skunk bush after water is carried adds the 6L90% alcohol reflux and extract, and extracting solution concentrates, last X-5 macroporous resin column absorption, with 3L 90% ethanol elution, collect elutriant, add 15g gac reflux decolour, the filtering gac, put cold crystallization, leach crystallizing and drying and promptly get ursolic acid 2.5g, through high phase Liquid Detection content 64.6%.
Embodiment 2:
Skunk bush is pulverized, got 1kg, add 15L water and be heated to 40 ℃, soak and extracted 2 hours, extract united extraction liquid 3 times, add the absorption of LSA-20 macroporous resin column, collect lower column liquid, use earlier the 3.5L water elution, water elution liquid and lower column liquid are merged, and adding ethanol to concentration is 70%, precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide 11.5g, content is 80.1%, uses 3L70% ethanolic soln wash-out again, collects alcohol eluen, concentrate and do not have alcohol, add the 350ml water-dispersion, add isopyknic n-butanol extraction 4 times, butanol extraction liquid concentrates and reclaims propyl carbinol, be drying to obtain morroniside 9.2g, content is 67.8%, and the residue of skunk bush after water is carried adds the 8L90% alcohol reflux and extract, and extracting solution concentrates, last LSA-10 macroporous resin column absorption, with 4L 90% ethanol elution, collect elutriant, add 20g gac reflux decolour, the filtering gac, put cold crystallization, leach crystallizing and drying and promptly get ursolic acid 1.8g, through high phase Liquid Detection content 67.5%.
Embodiment 3:
Skunk bush is pulverized, got 1kg, add 12L water and be heated to 60 ℃, soak and extracted 3 hours, extract united extraction liquid 2 times, add the absorption of LSA-20 macroporous resin column, collect lower column liquid, use earlier the 4L water elution, water elution liquid and lower column liquid are merged, and adding ethanol to concentration is 70%, precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide 11.7g, content is 72.7%, uses 3L70% ethanolic soln wash-out again, collects alcohol eluen, concentrate and do not have alcohol, add the 400ml water-dispersion, add isopyknic n-butanol extraction 2 times, butanol extraction liquid concentrates and reclaims propyl carbinol, be drying to obtain morroniside 8.1g, content is 69.9%, and the residue of skunk bush after water is carried adds the 7L90% alcohol reflux and extract, and extracting solution concentrates, last LSA-10 macroporous resin column absorption, with 3L 90% ethanol elution, collect elutriant, add 30g gac reflux decolour, the filtering gac, put cold crystallization, leach crystallizing and drying and promptly get ursolic acid 2.1g, through high phase Liquid Detection content 65.6%.
Embodiment 4:
Skunk bush is pulverized, got 5kg, add 55L water and be heated to 50 ℃, soak and extracted 2 hours, extract united extraction liquid 2 times, add the absorption of D101 macroporous resin column, collect lower column liquid, use earlier the 15L water elution, water elution liquid and lower column liquid are merged, and adding ethanol to concentration is 70%, precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide 58.9g, content is 73.4%, uses 15L70% ethanolic soln wash-out again, collects alcohol eluen, concentrate and do not have alcohol, add the 2L water-dispersion, add isopyknic n-butanol extraction 3 times, butanol extraction liquid concentrates and reclaims propyl carbinol, be drying to obtain morroniside 38.4g, content is 63.2%, and the residue of skunk bush after water is carried adds the 32L90% alcohol reflux and extract, and extracting solution concentrates, last HPD-700 macroporous resin column absorption, with 18L 90% ethanol elution, collect elutriant, add 150g gac reflux decolour, the filtering gac, put cold crystallization, leach crystallizing and drying and promptly get ursolic acid 9.3g, through high phase Liquid Detection content 66.6%.
Embodiment 5:
Skunk bush is pulverized, got 10kg, add 100L water and be heated to 65 ℃, soak and extracted 2 hours, extract united extraction liquid 2 times, add the absorption of D101 macroporous resin column, collect lower column liquid, use earlier the 35L water elution, water elution liquid and lower column liquid are merged, and adding ethanol to concentration is 70%, precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide 124.5g, content is 69.9%, uses 40L70% ethanolic soln wash-out again, collects alcohol eluen, concentrate and do not have alcohol, add the 4L water-dispersion, add isopyknic n-butanol extraction 2 times, butanol extraction liquid concentrates and reclaims propyl carbinol, be drying to obtain morroniside 75.8g, content is 60.5%, and the residue of skunk bush after water is carried adds the 70L90% alcohol reflux and extract, and extracting solution concentrates, last X-5 macroporous resin column absorption, with 35L 90% ethanol elution, collect elutriant, add 280g gac reflux decolour, the filtering gac, put cold crystallization, leach crystallizing and drying and promptly get ursolic acid 19.5g, through high phase Liquid Detection content 64.8%.
Embodiment 6:
Skunk bush is pulverized, got 10kg, add 120L water and be heated to 50 ℃, soak and extracted 2 hours, extract united extraction liquid 2 times, add the absorption of HPD100 macroporous resin column, collect lower column liquid, use earlier the 45L water elution, water elution liquid and lower column liquid are merged, and adding ethanol to concentration is 70%, precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide 134.4g, content is 66.3%, uses 50L70% ethanolic soln wash-out again, collects alcohol eluen, concentrate and do not have alcohol, add the 5L water-dispersion, add isopyknic n-butanol extraction 2 times, butanol extraction liquid concentrates and reclaims propyl carbinol, be drying to obtain morroniside 85g, content is 60.8%, and the residue of skunk bush after water is carried adds 65L and doubly measure the extraction of 90% alcohol reflux, and extracting solution concentrates, the resin column absorption of last X-5 hole, with 30L 90% ethanol elution, collect elutriant, add 250g gac reflux decolour, the filtering gac, put cold crystallization, leach crystallizing and drying and promptly get ursolic acid 20.4g, through high phase Liquid Detection content 65.6%.
Claims (5)
1. from skunk bush, unite the method for extracting morroniside, skunk bush polysaccharide and ursolic acid for one kind, it is characterized in that comprising following steps:
1) extract: skunk bush is pulverized, added 10-15 times of water gaging heating and extract 2-3 time, united extraction liquid, the residue after water is carried add 6-8 and doubly measure the extraction of 90% alcohol reflux, and extracting solution concentrates;
2) macroporous resin column I absorption: above-mentioned aqueous extract is added macroporous resin column I absorption, collect lower column liquid, water and ethanolic soln wash-out merge water elution liquid and lower column liquid successively, add the alcohol precipitation, leach precipitation and be drying to obtain skunk bush polysaccharide, collect alcohol eluen, concentrating does not have alcohol, add water-dispersion, add isopyknic n-butanol extraction 2-4 time, butanol extraction liquid concentrates and reclaims propyl carbinol, is drying to obtain morroniside;
3) macroporous resin column II absorption: macroporous resin column II absorption on the above-mentioned alcohol extracting concentrated solution, use 90% ethanol elution, collect elutriant, elutriant adds the gac reflux decolour, and the filtering gac is put cold crystallization, leaches crystallization, is drying to obtain ursolic acid.
2. the method for extracting morroniside, skunk bush polysaccharide and ursolic acid of uniting from skunk bush as claimed in claim 1 is characterized in that Heating temperature is 40-65 ℃ in the described step 1), extraction time 2-3 hour.
3. the method for extracting morroniside, skunk bush polysaccharide and ursolic acid of from skunk bush, uniting as claimed in claim 1, it is characterized in that described step 2) in the optional HPD100 of macroporous resin I, LSA-20 and D101 in a kind of, the used alcohol of wash-out is 70% ethanolic soln.
4. the method for extracting morroniside, skunk bush polysaccharide and ursolic acid of uniting from skunk bush as claimed in claim 1 is characterized in that a kind of among the optional X-5 of macroporous resin II, LSA-20 in the described step 3) and the SPD-700.
5. the method for extracting morroniside, skunk bush polysaccharide and ursolic acid of uniting from skunk bush as claimed in claim 1 is characterized in that the gac in the described step 3) is a medical injection class gac, and add-on is the 0.5-1% of amount of liquid.
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Cited By (11)
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| CN102293250A (en) * | 2011-07-21 | 2011-12-28 | 河南中医学院 | Cornus officinalis sugar-reduced instant milk powder solid beverage |
| CN102293251A (en) * | 2011-07-21 | 2011-12-28 | 河南中医学院 | Cornus officinalis fruit milk |
| CN102614243A (en) * | 2012-04-26 | 2012-08-01 | 西北大学 | Method for extracting common macrocarpium fruit total glycoside and application of common macrocarpium fruit total glycoside to preparation of hypoxia tolerant medicines |
| CN106928376A (en) * | 2017-03-23 | 2017-07-07 | 李春生 | The separation method of skunk bush polysaccharide and its application |
| CN107286211A (en) * | 2017-02-14 | 2017-10-24 | 盐城卫生职业技术学院 | A kind of preparation method of morroniside |
| CN108341845A (en) * | 2018-01-26 | 2018-07-31 | 北京联合大学 | The method that cornel extractive prepares high-purity morroniside |
| CN108467416A (en) * | 2018-06-21 | 2018-08-31 | 长沙爱扬医药科技有限公司 | The method that Fructus Corni extracts morroniside, loganin and ursolic acid |
| CN110623188A (en) * | 2019-10-29 | 2019-12-31 | 西峡县森林家食品有限责任公司 | Method for preparing dogwood alcohol extract particles and corresponding alcohol extract particles |
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| CN102293251A (en) * | 2011-07-21 | 2011-12-28 | 河南中医学院 | Cornus officinalis fruit milk |
| CN102293250A (en) * | 2011-07-21 | 2011-12-28 | 河南中医学院 | Cornus officinalis sugar-reduced instant milk powder solid beverage |
| CN102614243A (en) * | 2012-04-26 | 2012-08-01 | 西北大学 | Method for extracting common macrocarpium fruit total glycoside and application of common macrocarpium fruit total glycoside to preparation of hypoxia tolerant medicines |
| CN107286211A (en) * | 2017-02-14 | 2017-10-24 | 盐城卫生职业技术学院 | A kind of preparation method of morroniside |
| CN106928376B (en) * | 2017-03-23 | 2019-01-15 | 李春生 | The separation method of skunk bush polysaccharide and its application |
| CN106928376A (en) * | 2017-03-23 | 2017-07-07 | 李春生 | The separation method of skunk bush polysaccharide and its application |
| CN108341845B (en) * | 2018-01-26 | 2021-02-26 | 北京联合大学 | Method for preparing morroniside from dogwood extract |
| CN108341845A (en) * | 2018-01-26 | 2018-07-31 | 北京联合大学 | The method that cornel extractive prepares high-purity morroniside |
| CN108467416A (en) * | 2018-06-21 | 2018-08-31 | 长沙爱扬医药科技有限公司 | The method that Fructus Corni extracts morroniside, loganin and ursolic acid |
| CN110623188A (en) * | 2019-10-29 | 2019-12-31 | 西峡县森林家食品有限责任公司 | Method for preparing dogwood alcohol extract particles and corresponding alcohol extract particles |
| CN113861302A (en) * | 2021-10-14 | 2021-12-31 | 西北农林科技大学 | Dogwood polysaccharide component and preparation method and application thereof |
| CN115501293A (en) * | 2022-09-06 | 2022-12-23 | 北京澳特舒尔保健品开发有限公司 | Preparation method of prepared rehmannia root, chinese yam and kudzuvine root hypoglycemic composition |
| CN115501293B (en) * | 2022-09-06 | 2024-01-16 | 北京澳特舒尔保健品开发有限公司 | Preparation method of blood glucose reducing composition containing prepared rehmannia root, chinese yam and kudzuvine root |
| CN117243968A (en) * | 2023-11-13 | 2023-12-19 | 济南舜景医药科技有限公司 | Celecoxib compound preparation and preparation method thereof |
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Application publication date: 20110720 |