CN101412725B - Method for extracting and separating bilobalide B from ginkgo leaf - Google Patents
Method for extracting and separating bilobalide B from ginkgo leaf Download PDFInfo
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- CN101412725B CN101412725B CN2007100502455A CN200710050245A CN101412725B CN 101412725 B CN101412725 B CN 101412725B CN 2007100502455 A CN2007100502455 A CN 2007100502455A CN 200710050245 A CN200710050245 A CN 200710050245A CN 101412725 B CN101412725 B CN 101412725B
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Abstract
The invention discloses a method for extracting and separating ginkgolides B from folium ginkgo, which comprises the following steps: 1) taking the folium ginkgo, carrying out extraction by ethanol with different concentrations from high to low, combining extracting solutions, and reclaiming the ethanol to obtain concentrated extracting solution; 2) adding ethyl acetate into the concentrated extracting solution for extraction, reclaiming organic phase and concentrating the extracting solution into extract; 3) diluting the extract obtained in step 2), putting the extract to preferential polar imperforate adsorption resin, washing the preferential polar imperforate adsorption resin by ethanol, reclaiming the ethanol in eluate, and crystallizing by the ethanol to obtain ginkgolides compounds; 4) putting the ginkgolides compound crystal to silica gel column, washing the silica gel column by miscible liquids of normal hexane and ethyl acetate, and collecting eluate to obtain eluate of ginkgolides B; and 5) reclaiming solvent in eluate collected in step 4), and crystallizing the solvent by ethanol to obtain ginkgolides B monomer. The method has the advantages of simple process, low production cost, high purity of products, and easy industrial production.
Description
(1) technical field:
The present invention relates to from plant, extract the method for effective ingredient, be specifically related to the method for extraction separation Ginkgolide B from Ginkgo Leaf.
(2) background technology:
Ginkgo claims maidenhair tree again, belongs to gymnosperm, is one of the veteran kind of unique existence of Ginkgoaceae Ginkgo, and its leaf and fruit have important pharmaceutical use.What research was maximum at present is Folium Ginkgo extract, and it comprises flavonoid compound and ginkgolide compound.Flavonoid compound has 38 kinds approximately, and total content is 22-27%; Ginkgolide compound comprises bilobalide and bilobalide, and total content is 5.4-6.6%.Bilobalide mainly comprises Ginkgolide A, B, C, J and M monomer; According to the literature, each monomeric pharmic function has certain difference in the bilobalide, wherein, Ginkgolide A, B have significant curative effect to the treatment cardiovascular and cerebrovascular diseases, bilobalide is to treating then drug effect uniqueness of nervous system disorders, in order to improve its medicinal result of treatment, sometimes must be with each monomer separation purifying; Because bilobalide is the sesquiterpene material, and Ginkgolide A, B, C, J, M are the diterpenes materials, and their molecular structure is comparatively similar, and polarity difference is also very little, cause in the bilobalide each monomeric extraction with separate the comparison difficulty.The extracting method of existing Ginkgolide B has a variety of, as microwave extraction method, solution extraction method etc., for example application number is 200510063407.X, name is called the Chinese invention patent of " a kind of novel method of extracting Ginkgolide B from Ginkgo Leaf or Folium Ginkgo extract ", disclose in a kind of Ginkgo Leaf or the Folium Ginkgo extract method of extracting Ginkgolide B, this extracting method step is: 1) get Ginkgo Leaf or Folium Ginkgo extract adds water boil, refrigeration, get supernatant liquid filtering, get filtrate; 2) filtrate extracts with propyl carbinol or similar solubleness to propyl carbinol or polar solvent, divides water-yielding stratum; 3) solvent in the recovery extraction liquid, drying gets dry thing; 4) add ethanol in the dry thing and boil and make its dissolving, refrigeration, suction filtration, wash crystal; 5) add ethanol in the crystal and make its dissolving, refrigeration, suction filtration gets the Ginkgolide B monomer; 6) the Ginkgolide B monomer obtains purity through vacuum-drying and reaches Ginkgolide B monomer more than 90%.
(3) summary of the invention:
The present invention will disclose a kind of high method of extraction separation Ginkgolide B from Ginkgo Leaf of income rate height, purity of extracting.
The method of the present invention's extraction separation Ginkgolide B from Ginkgo Leaf, its step is as follows:
1) get Ginkgo Leaf, extract with Different concentrations of alcohol from high to low, united extraction liquid reclaims ethanol, the extracting solution after obtaining concentrating;
Take by weighing a certain amount of Ginkgo Leaf, can be earlier be that the ethanol of 60-80% extracted 1-3 hour Ginkgo Leaf 50-70 ℃ the time with volumetric concentration, wherein, the weight that Ginkgo Leaf and alcoholic acid proportioning are pressed Ginkgo Leaf: alcoholic acid volume=1: 8-10; Ginkgo Leaf is separated, and is that the ethanol of 30-55% extracted 1-3 hour Ginkgo Leaf 50-70 ℃ the time with volumetric concentration again, wherein, and the weight that Ginkgo Leaf and alcoholic acid proportioning are pressed Ginkgo Leaf: alcoholic acid volume=1: 6-8; Ginkgo Leaf being separated, is that the ethanol of 10-25% extracted 1-3 hour Ginkgo Leaf in the time of 50-70 ℃ with volumetric concentration again, wherein, and the weight that Ginkgo Leaf and alcoholic acid proportioning are pressed Ginkgo Leaf: alcoholic acid volume=1: 5-7; United extraction liquid reclaims ethanol, extracting solution is concentrated into 8-10 times of volume of Ginkgo Leaf weight;
2) add ethyl acetate extraction in the extracting solution after concentrating, be concentrated into medicinal extract after the recovery organic phase;
Can add equal volume of ethyl acetate in concentrated solution, in general, it is better to extract the effect that is reached for 3 times;
3) with step 2) the back selective polarity atresia adsorption resin column of going up of gained medicinal extract dilution, use ethanol elution, the gained elutriant obtains ginkgolide compound with alcohol crystal after reclaiming ethanol again;
The model of described selective polarity atresia adsorption resin column can be ADS-15, or ADS-17, or ADS-F8; With step 2) gained medicinal extract, can wash with water earlier doubly to the water dilution back of its weight upper prop with 50-200, and is colourless until effluent liquid; And then be the ethanol elution of 50-70% with volumetric concentration, the 30-60 that the volumetric usage of described eluent can be above-mentioned medicinal extract weight is doubly; The elutriant that collection is obtained reclaims ethanol, is concentrated into medicinal extract, is that the ethanol of 50-80% is solvent crystallization with volumetric concentration again, and the gained crystallization is ginkgolide compound;
4) with silicagel column in the ginkgolide compound crystallization, with the mixed solution wash-out of normal hexane and ethyl acetate, collect elutriant, obtain the elutriant of enrichment Ginkgolide B;
The volume ratio of normal hexane and ethyl acetate is preferably 9 in the mixed solution of described normal hexane and ethyl acetate: 1-2: 8; In the process of wash-out,, treat that solvent peak the 3rd place, peak after rolling begins to collect elutriant, obtains the elutriant of enrichment Ginkgolide B with the online detection and location of light scattering detector;
5) recycling step 4) in solvent in the elutriant collected, use alcohol crystal again, obtain Ginkgolide B.
Recycling step 4) solvent in the elutriant of collecting in, again with volumetric concentration be the ethanol of 30-70% to its crystallization, the gained crystallization is the Ginkgolide B monomer.
Advantage of the present invention:
The present invention adopts from high to low Different concentrations of alcohol that Ginkgo Leaf is extracted, and the monomeric extraction yield of Ginkgolide B has been improved more than 10%; Also adopted special selective polarity not have macroporous adsorbent resin among the present invention and carried out removal of impurities, can remove most of influences the isolating impurity of silicagel column, realized that upper prop is separablely to obtain the Ginkgolide B monomer, and purity reaches more than 99%; Compared with prior art, method technology provided by the invention is simple, production cost is low, and products obtained therefrom purity height is easier to the production of industrialization.
(4) embodiment:
Embodiment 1
1) getting 10 kilograms of Ginkgo Leaves, is that 80% ethanol extracted 1 hour Ginkgo Leaf in the time of 50 ℃ with 100 liters of volumetric concentrations, with 200 purpose filter clothes Ginkgo Leaf is separated; Being 55% ethanol with 60 liters of volumetric concentrations again extracted 1 hour Ginkgo Leaf 70 ℃ the time, with 200 purpose filter clothes Ginkgo Leaf was separated; Being 25% ethanol with 50 liters of volumetric concentrations again extracted 1 hour Ginkgo Leaf 50 ℃ the time, with 200 purpose filter clothes Ginkgo Leaf was separated; Merge the extracting solution of three extraction gained, reclaim ethanol, extracting solution is concentrated into 100 liters of concentrated solutions;
2) in concentrated solution, add 100 liters of ethyl acetate extractions 3 times, merge the organic phase that extracting and separating goes out, concentrate after the recovery organic phase and obtain 500 gram medicinal extract;
3) with step 2) in gained medicinal extract add 50 times of volume water dilution back and go up the ADS-15 posts, wash with water earlier, colourless until effluent liquid, be 50% ethanol elution again with 15 liters of volumetric concentrations, collect elutriant, reclaim ethanol, be concentrated into medicinal extract, be 50% alcohol crystal again with volumetric concentration, obtain 70 gram ginkgolide compound crystal;
4) with silicagel column in the ginkgolide compound crystallization, carry out gradient elution with the mixed solution of normal hexane and ethyl acetate, wherein, the volume ratio of normal hexane and ethyl acetate is 9: 1-2: 8; In elution process,, treat that solvent peak the 3rd place, peak after rolling begins to collect elutriant, obtains the elutriant of enrichment Ginkgolide B with the online detection and location of light scattering detector;
5) recycling step 4) in solvent in the elutriant collected, again with volumetric concentration be 40% ethanol to its crystallization, obtain Ginkgolide B monomer 4.55 and restrain.
Embodiment 2
1) getting 50 kilograms of Ginkgo Leaves, is that 60% ethanol extracted 3 hours Ginkgo Leaf in the time of 70 ℃ with 400 liters of volumetric concentrations, with 200 purpose filter clothes Ginkgo Leaf is separated; Being 30% ethanol with 400 liters of volumetric concentrations again extracted 3 hours Ginkgo Leaf 70 ℃ the time, with 200 purpose filter clothes Ginkgo Leaf was separated; Being 10% ethanol with 300 liters of volumetric concentrations again extracted 3 hours Ginkgo Leaf 70 ℃ the time, with 200 purpose filter clothes Ginkgo Leaf was separated; Merge the extracting solution of three extraction gained, reclaim ethanol, extracting solution is concentrated into 500 liters of concentrated solutions;
2) in concentrated solution, add 500 liters of ethyl acetate extractions 3 times, merge the organic phase that extracting and separating goes out, concentrate after the recovery organic phase and obtain 1.5 kilograms of medicinal extract;
3) with step 2) in gained medicinal extract add 200 times of volume water dilution back and go up the ADS-17 posts, wash with water earlier, colourless until effluent liquid, be 70% ethanol elution again with 60 liters of volumetric concentrations, collect elutriant, reclaim ethanol, be concentrated into medicinal extract, be 70% alcohol crystal again with volumetric concentration, obtain 233 gram ginkgolide compound crystal;
4) with silicagel column in the ginkgolide compound crystallization, carry out gradient elution with the mixed solution of normal hexane and ethyl acetate, wherein, the volume ratio of normal hexane and ethyl acetate is 9: 1-2: 8; In elution process,, treat that solvent peak the 3rd place, peak after rolling begins to collect elutriant, obtains the elutriant of enrichment Ginkgolide B with the online detection and location of light scattering detector;
5) recycling step 4) in solvent in the elutriant collected, again with volumetric concentration be 30% ethanol to its crystallization, obtain Ginkgolide B monomer 81.90 and restrain.
Embodiment 3
1) getting 40 kilograms of Ginkgo Leaves, is that 70% ethanol extracted 1 hour Ginkgo Leaf in the time of 70 ℃ with 280 liters of volumetric concentrations, with 200 purpose filter clothes Ginkgo Leaf is separated; Being 50% ethanol with 280 liters of volumetric concentrations again extracted 2 hours Ginkgo Leaf 60 ℃ the time, with 200 purpose filter clothes Ginkgo Leaf was separated; Being 20% ethanol with 280 liters of volumetric concentrations again extracted 2 hours Ginkgo Leaf 70 ℃ the time, with 200 purpose filter clothes Ginkgo Leaf was separated; Merge the extracting solution of three extraction gained, reclaim ethanol, extracting solution is concentrated into 400 liters of concentrated solutions;
2) in concentrated solution, add 400 liters of ethyl acetate extractions 3 times, merge the organic phase that extracting and separating goes out, concentrate after the recovery organic phase and obtain 1.2 kilograms of medicinal extract;
3) with step 2) in gained medicinal extract add 100 times of volume water dilution back and go up the ADS-F8 posts, wash with water earlier, colourless until effluent liquid, be 60% ethanol elution again with 70 liters of volumetric concentrations, collect elutriant, reclaim ethanol, be concentrated into medicinal extract, be 80% alcohol crystal again with volumetric concentration, obtain 225 gram ginkgolide compound crystal;
4) with silicagel column in the ginkgolide compound crystallization, carry out gradient elution with the mixed solution of normal hexane and ethyl acetate, wherein, the volume ratio of normal hexane and ethyl acetate is 9: 1-2: 8; In elution process,, treat that solvent peak the 3rd place, peak after rolling begins to collect elutriant, obtains the elutriant of enrichment Ginkgolide B with the online detection and location of light scattering detector;
5) recycling step 4) in solvent in the elutriant collected, again with volumetric concentration be 50% ethanol to its crystallization, obtain Ginkgolide B monomer 16.72 and restrain.
Claims (8)
1. the method for extraction separation Ginkgolide B from Ginkgo Leaf, its step is as follows:
1) get Ginkgo Leaf, extract with Different concentrations of alcohol from high to low, united extraction liquid reclaims ethanol, the extracting solution after obtaining concentrating; Described usefulness Different concentrations of alcohol is from high to low extracted and is meant: be that the ethanol of 60-80% extracts Ginkgo Leaf with volumetric concentration earlier; Be that the ethanol of 30-55% extracts Ginkgo Leaf with volumetric concentration then; Be that the ethanol of 10-25% extracts Ginkgo Leaf with volumetric concentration again;
2) add ethyl acetate extraction in the extracting solution after concentrating, be concentrated into medicinal extract after the recovery organic phase;
3) with step 2) the back selective polarity macroporous adsorptive resins of going up of gained medicinal extract dilution, use ethanol elution, the gained elutriant obtains ginkgolide compound with alcohol crystal after reclaiming ethanol again;
4) with silicagel column in the ginkgolide compound crystallization, with the mixed solution wash-out of normal hexane and ethyl acetate, collect elutriant, obtain the elutriant of enrichment Ginkgolide B; In described normal hexane and the ethyl acetate mixed solution, the volume ratio of normal hexane and ethyl acetate is 9: 1-2: 8;
5) recycling step 4) in solvent in the elutriant collected, use alcohol crystal again, obtain Ginkgolide B.
2. according to claim 1 from Ginkgo Leaf the method for extraction separation Ginkgolide B, it is characterized in that: in the step 1), the temperature of described extraction is 50-70 ℃.
3. according to claim 1 from Ginkgo Leaf the method for extraction separation Ginkgolide B, it is characterized in that: in the step 1), the weight that Ginkgo Leaf and alcoholic acid proportioning are pressed Ginkgo Leaf when extracting for the first time: alcoholic acid volume=1: 8-10; The weight that Ginkgo Leaf and alcoholic acid proportioning are pressed Ginkgo Leaf when extracting for the second time: alcoholic acid volume=1: 6-8; The weight that Ginkgo Leaf and alcoholic acid proportioning are pressed Ginkgo Leaf when extracting for the third time: alcoholic acid volume=1: 5-7.
4. according to claim 1 and 2 from Ginkgo Leaf the method for extraction separation Ginkgolide B, it is characterized in that: step 2) in, the volume of the ethyl acetate of described adding with concentrate after the volume ratio of extracting solution be 1: 1, the number of times of extraction is 3 times.
5. according to claim 1 and 2 from Ginkgo Leaf the method for extraction separation Ginkgolide B, it is characterized in that: in the step 3), described selective polarity macroporous adsorbent resin model is ADS-15, or ADS-17, or ADS-F8.
6. according to claim 1 and 2 from Ginkgo Leaf the method for extraction separation Ginkgolide B, it is characterized in that: in the step 3), described wash-out is 50-70% with the alcoholic acid volumetric concentration.
7. according to claim 1 and 2 from Ginkgo Leaf the method for extraction separation Ginkgolide B, it is characterized in that: in the step 3), described crystallization is 50-80% with the alcoholic acid volumetric concentration.
8. according to claim 1 and 2 from Ginkgo Leaf the method for extraction separation Ginkgolide B, it is characterized in that: in the step 4),, collect elutriant with the online detection and location of light scattering detector.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2007100502455A CN101412725B (en) | 2007-10-15 | 2007-10-15 | Method for extracting and separating bilobalide B from ginkgo leaf |
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| CN2007100502455A CN101412725B (en) | 2007-10-15 | 2007-10-15 | Method for extracting and separating bilobalide B from ginkgo leaf |
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| CN101412725A CN101412725A (en) | 2009-04-22 |
| CN101412725B true CN101412725B (en) | 2010-12-08 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103130817A (en) * | 2013-03-26 | 2013-06-05 | 山东罗欣药业股份有限公司 | New bilobalide B compound and preparation method thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102887909B (en) * | 2012-11-07 | 2014-12-03 | 黑龙江天宏药业股份有限公司 | Method for extracting and separating ginkgolide B from ginkgo leaves |
| CN103130818B (en) * | 2013-03-26 | 2014-03-05 | 山东罗欣药业股份有限公司 | Bilobalide B compound and preparation method thereof |
| CN104447790B (en) * | 2013-09-22 | 2017-05-17 | 江苏康缘药业股份有限公司 | Separation and purification method for ginkgolide B |
| CN104817570B (en) * | 2015-04-23 | 2018-02-13 | 北京汉典制药有限公司 | A kind of ginkolide B preparation method and its ginkolide B being prepared |
| CN113801133B (en) * | 2021-10-28 | 2022-08-19 | 江苏得乐康生物科技有限公司 | Preparation method of ginkgolide and monomer contained in ginkgolide |
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Cited By (1)
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| CN103130817A (en) * | 2013-03-26 | 2013-06-05 | 山东罗欣药业股份有限公司 | New bilobalide B compound and preparation method thereof |
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