CN1530363A - Method of extracting terpene lactone from folium ginkgo leaves and product - Google Patents
Method of extracting terpene lactone from folium ginkgo leaves and product Download PDFInfo
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- CN1530363A CN1530363A CNA031197442A CN03119744A CN1530363A CN 1530363 A CN1530363 A CN 1530363A CN A031197442 A CNA031197442 A CN A031197442A CN 03119744 A CN03119744 A CN 03119744A CN 1530363 A CN1530363 A CN 1530363A
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Abstract
A process for extracting terperiod ginkalide from ginkgo leaf and a product which is prepared by extracting in alcohol and resin concentrating and has high content of ginkalide are disclosed. Its advantages are low cost and less environmental pollution. Said product can be used for treating senile dementia and cardiovascular and cerebrovascular diseases.
Description
[technical field]
The present invention relates to a kind of method of from Ginkgo Leaf, extracting the ginkgo terpene lactone, particularly, the present invention relates to a kind of employing ethanol-extracted, the method for resin concentration, and product and the application thereof of adopting the high content of bilobalide of this method acquisition.
[background technology]
Folium Ginkgo terpene lactones is diterpenoid-lactone with special construction and the sesquiterpene lactones of finding from Ginkgo Leaf.At present, bilobalide (Ginkgolide) A, Ginkgolide B, ginkalide C, bilobalide M, bilobalide J and bilobalide (Bilobalide) from Ginkgo Leaf, have been isolated.This is the confessed a kind of antagonist that special effective platelet activation factor (PAF) acceptor of application prospect is arranged most of current the world of medicine, its specificity height.Up-to-date pharmacological experiments proves: Folium Ginkgo terpene lactones has provide protection to ischemic injuries and central nervous system.
People separate from Ginkgo Leaf very early and have obtained Folium Ginkgo terpene lactones, have also studied the chemical structure of each lactone of ginkgo, have confirmed that the Folium Ginkgo terpene lactones molecule has complicated three-dimensional arrangement, and its synthetic difficulty is very big.People find that Ginkgo Leaf is the major industry raw materials for production that extract the Folium Ginkgo terpene lactones compound.
Since the sixties, the separating and extracting method of Folium Ginkgo terpene lactones has bibliographical information.But because this kind compound content is very low in the Ginkgo Leaf, and has ad hoc structure, the extraction separation step is loaded down with trivial details, and is time-consuming, and yield is low.At present, the extracting method that external general employing organic solvent multi-stage solvent extraction and diatomite, silica gel adsorption-wash-out or charcoal absorption-wash-out combine with the plumbic acetate precipitator method is (referring to day disclosure special permission communique, flat 3-24084 (1991), flat 3-264533 (1991)), but with content of bilobalide in the product of this method final production only is about 3%.The separating and extracting method of Folium Ginkgo terpene lactones also has report (referring to Zhang Diqing, He Zhaofan work, Ginkgo Leaf resource chemical research, China Light Industry Press, August in 1998 the 1st edition, the 129th page) in recent years at home.Its roughly operation be: Ginkgo Leaf is after lixiviate, vat liquor passes through alumina column, again through extraction, by silicagel column and mistake activated carbon column, its solution carries out crystallization and obtains its product, but this technology is loaded down with trivial details time-consuming, and used aluminum oxide, silica gel and gac are difficult for reclaiming, cost is higher, and the lactone loss is serious, and yield only is about 0.4%.Therefore, still need a kind of with low costly, the method that environmental pollution is little adopts this method can obtain the product of high lactone content.
[summary of the invention]
[goal of the invention]
The invention provides a kind of method of from Ginkgo Leaf, extracting the ginkgo terpene lactone.The present invention relates to adopt described method, comprising using the ethanol-extracted Ginkgo Leaf, its extracting solution, obtains content of bilobalide and reaches more than 20% again through the ethyl acetate extraction purifying through the macroporous adsorbent resin enrichment, the total product of lactone more than 50%.Compared with the prior art, production method of the present invention has with low cost, the advantage that the product content of bilobalide is high, and therefore this method is particularly suitable for large-scale industrialization production.
Another object of the present invention is to adopt the prepared product of aforesaid method.
A further object of the invention is the application of product in treatment senile dementia, cardiovascular and cerebrovascular diseases of adopting aforesaid method to obtain.
[technical scheme]
Ginkgo Leaf involved in the present invention is a higher plant, Spermatophyta, and Gymnospermae, Ginkgoaceae GinKgo aceae, ginkgo GinKgo biloba L (deciduous tree) is seven, the August green leaf of plucking gained after drying.
Method of the present invention comprises following each processing step:
(1) the exsiccant ginkgo leaf powder is broken to sheet, place in the refluxing extraction jar, add concentration 40-60 volume % ethanol, its ethanolic soln consumption be make a living by weight dose 5-10 doubly, temperature 75-85 ℃ of following refluxing extraction 3-5 time, each 1-3 hour, need to filter after each the extraction, the merging of these filtrates obtains extracting solution.
(2) described extracting solution≤-0.065Mpa pressure under concentrating under reduced pressure, reclaim its ethanol, this concentrating until the concentrated solution that obtains not having alcohol.
(3) add deionized water and return molten above-mentioned concentrated solution, return molten solution amount and generally be make a living by weight dose 6-10 doubly, return the molten solution left standstill that obtains, filtration.
(4) soup that obtains after filtering adsorbs the weight ratio of crude drug amount and resin demand=1: 0.8-2.0, this precious grace chemical plant, Cangzhou, resin effluent north company limited production with the flow velocity of 1-1.5 times of column volume per hour by nonpolar class macroporous resin column.The absorption back then, with the about 10-20 volume of about 2-6 times column volume % aqueous ethanolic solution wash-out, discards elutriant earlier with 1-4 times of column volume deionized water rinsing, with 2-5 times of column volume 60 volume % aqueous ethanolic solution wash-outs, collects this elutriant again.
(5) with the elutriant collected≤-be evaporated to the medicinal extract that does not have alcohol under the 0.065Mpa pressure, add ethyl acetate extraction 2-5 time then, adding the ethyl acetate total amount is in 0.5-1.0 times of volume of crude drug amount, the combined ethyl acetate extraction liquid washs or does not wash with inorganic or organic sodium salt solution again.Described mineral acid sodium salt is sodium bisulfite, SODIUMNITRATE, SODIUM PHOSPHATE, MONOBASIC etc., and described organic acid sodium salt is sodium-acetate, Trisodium Citrate, sodium oxalate etc.
(6) acetic acid ethyl acetate extract is evaporated to medicinal extract under-0.04Mpa--0.06Mpa pressure, passes through vacuum-drying then, and resulting dry thing is crushed to fine powder and promptly obtains the finished product of the present invention.
(7) detect Folium Ginkgo terpene lactones content in the finished product.
Ginkgo product inspection method of the present invention is as follows:
Chromatographic condition and system suitability test: with octadecylsilane chemically bonded silica is weighting agent; With n-propyl alcohol-tetrahydrofuran (THF)-water mixture (by volume, 1: 15: 84) is moving phase; Detect with light scattering detector; Number of theoretical plate calculates by the bilobalide peak should be not less than 2500; The resolution at bilobalide and ginkalide C peak should be greater than 1.5.
The preparation of reference substance solution: it is an amount of that precision takes by weighing bilobalide, Ginkgolide A, Ginkgolide B and ginkalide C reference substance respectively, adds methyl alcohol and make mixing solutions that every 1ml contains 2mg, 1mg, 1mg, 1mg promptly.
The preparation of need testing solution: precision takes by weighing the about 20mg of product of the present invention, adds dissolve with methanol and is transferred in the 5ml measuring bottle, adds methyl alcohol to scale, shakes up, promptly.
Assay method: accurate respectively reference substance solution 10 μ l, the 15 μ l of drawing, need testing solution 10 μ l inject liquid chromatograph, measure, calculate the content of bilobalide, Ginkgolide A, Ginkgolide B, ginkalide C respectively with external standard two-point method logarithmic equation, promptly.
[beneficial effect] compared with the prior art, method of the present invention has following beneficial effect:
1. operation is simple, and low cost product is carried out the big production of mass-producing easily.
2. bilobalide loses hardly in the whole technology, the content of bilobalide height in the finished product, and content of bilobalide reaches more than 20%, and total lactone is more than 50%.
3. no ginkgolic acid is residual in the product.
4. the organic solvent that uses in the inventive method is few, and environment is not polluted.
[embodiment]
The Ginkgo Leaf (its water-content is less than 10 weight %) that embodiment 1:100kg pulverizes with 50 volume % ethanol 700L in the refluxing extraction jar, be heated to 80 ℃ of temperature, refluxing extraction 2 hours, extracted after-filtration, add 50 volume % aqueous ethanolic solutions again and extract secondary, each 400L extracted 2 hours down for 80 ℃ in temperature, and the merging of filtering filtrate obtains extracting solution.With external circulation evaporator pressure≤-concentrate described extracting solution under the 0.065Mpa, the concentrated solution until obtaining not having alcohol adds deionized water then to 600L, is cooled to room temperature, places 6 hours again, filters.Filtrate is adsorbed by 100kg HPD-100 macroporous resin column with 2L/min speed, this precious grace chemical plant, Cangzhou, resin effluent north company limited produces, after having advanced feed liquid, leave standstill 10min, wash with flow velocity 2L/min with deionized water 200L earlier, use 400L 20 volume % ethanol elutions then, this elutriant discards, immediately following crossing post with 60 volume % ethanol 400L, outlet liquid begins to collect when darkening, and stops until colourless, the elutriant of collecting pressure≤-to concentrate up to proportion under the 0.065Mpa be 1.14, with ethyl acetate extraction three times, each add-on is respectively 30L, 30L, 20L merges three times acetic acid ethyl acetate extract, the extraction liquid reconcentration of this merging to proportion is 1.16, put into vacuum drying oven and be dried to driedly, obtain terpene lactones product 0.612kg of the present invention, its analytical results sees the following form 1.
Embodiment 2: in the refluxing extraction jar, 100kg is ground into flaky Ginkgo Leaf and adds 45 volume % ethanol 650L, be heated to 85 ℃, refluxing extraction 2 hours is filtered, add 45 volume % extraction using alcohol secondaries again, add-on is followed successively by 450L, and 350L extracted 2 hours down at 85 ℃, filter united extraction liquid.With external circulation evaporator pressure≤-0.065Mpa under concentrated extracting solution to 300L, add deionized water to 600L, be cooled to room temperature after, placed 6 hours, filter.Filtrate is crossed 100kg HPD-100 macroporous resin column with 3L/min speed, after having advanced feed liquid, leave standstill 10min, add deionized water 300L and cross post (flow velocity 2L/min), cross post with 400L 15 volume % ethanol again, the outlet effluent liquid discards, and crosses post immediately following 60 volume % ethanol 400L, outlet liquid begins to collect when darkening, and collects until colourless stopping.Elutriant with external circulation evaporator pressure≤-be concentrated into 20L after reclaiming ethanol under the 0.065Mpa, add water to 50L, divide three times and add ethyl acetate extraction, add-on is respectively 30L, 30L, 15L, merges three times acetic acid ethyl fluid, add 4 weight % sodium acetate soln 50L washing, get acetic acid ethyl acetate extract after the layering, again pressure≤-to be concentrated into proportion under the 0.065Mpa be 1.16, put into vacuum drying oven and be dried to dried, get terpene lactones 0.589kg, its product analysis the results are shown in following table.
The finished product detected result
| Sequence number | Bilobalide | Ginkgolide A | Ginkgolide B | Ginkalide C | Total lactone |
| Embodiment 1 | ?20.46％ | 25.12％ | 12.36％ | 6.16％ | 64.1％ |
| Embodiment 2 | ?22.39％ | 26.34％ | 11.56％ | 5.82％ | 66.11％ |
Claims (8)
1, a kind of method of extracting the ginkgo terpene lactone from Ginkgo Leaf is characterized in that this method comprises the steps:
A, with the dry Folium Ginkgo of pulverizing, with concentration 40-60 volume % ethanol, obtain extracting solution temperature 75-85 ℃ of following refluxing extraction,
B, described extracting solution concentrating under reduced pressure, until the concentrated solution that obtains not having alcohol,
C, add deionized water and return molten described concentrated solution, return molten solution amount and generally be make a living by weight dose 6-10 doubly, the solution left standstill that obtains, filtration,
The soup that obtains after D, the filtration adsorbs with nonpolar type macroporous resin column, crude drug amount and resin demand weight ratio=1: 0.8-2.0, then, earlier with the about 20 volume % aqueous ethanolic solution wash-outs of about 2-6 times column volume, discard elutriant, with 2-5 times of column volume 60 volume % aqueous ethanolic solution wash-outs, collect this elutriant again
E, with the elutriant collected≤-0.065Mpa pressure under concentrating under reduced pressure up to obtaining medicinal extract, obtain acetic acid ethyl acetate extract with ethyl acetate extraction then, wash or do not wash with inorganic or organic sodium salt solution again,
F, washing or the acetic acid ethyl acetate extract that do not wash are evaporated to medicinal extract under-0.04Mpa--0.06Mpa pressure, pass through vacuum-drying then, obtain the finished product of the present invention.
2, method according to claim 1 is characterized in that described refluxing extraction carries out 3-5 time, each 1-3 hour.
3, method according to claim 1, it is characterized in that described extracting solution≤-carry out concentrating under reduced pressure under the 0.065Mpa pressure.
4, method according to claim 1 is characterized in that using deionized water rinsing after macroporous resin adsorption.
5, method according to claim 1 is characterized in that using the ethyl acetate extraction in 0.5-0.8 times of volume of crude drug amount.
6, method according to claim 1 is characterized in that the vacuum-drying thing is crushed to more than 80 orders.
7, the product that obtains according to the described method of arbitrary claim among the claim 1-6 is characterized in that content of bilobalide is higher than 20%, and total lactone content is higher than 50%.
8, the application of product in treatment senile dementia, cardiovascular and cerebrovascular diseases that obtains according to the described method of arbitrary claim among the claim 1-6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031197442A CN1301988C (en) | 2003-03-11 | 2003-03-11 | Method of extracting terpene lactone from folium ginkgo leaves and product |
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| CNB031197442A CN1301988C (en) | 2003-03-11 | 2003-03-11 | Method of extracting terpene lactone from folium ginkgo leaves and product |
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| CN1530363A true CN1530363A (en) | 2004-09-22 |
| CN1301988C CN1301988C (en) | 2007-02-28 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1935798B (en) * | 2005-09-23 | 2010-09-08 | 天津天士力制药股份有限公司 | Method for preparing and rographalide |
| CN102416027A (en) * | 2011-12-01 | 2012-04-18 | 徐州医学院 | Gingkgo active ingredient extraction and separation method and use of extracted active matters in medicines for treating cardiovascular and cerebrovascular diseases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1073436C (en) * | 1999-07-05 | 2001-10-24 | 李益农 | Gingko leaf extract preparation |
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2003
- 2003-03-11 CN CNB031197442A patent/CN1301988C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1935798B (en) * | 2005-09-23 | 2010-09-08 | 天津天士力制药股份有限公司 | Method for preparing and rographalide |
| CN102416027A (en) * | 2011-12-01 | 2012-04-18 | 徐州医学院 | Gingkgo active ingredient extraction and separation method and use of extracted active matters in medicines for treating cardiovascular and cerebrovascular diseases |
| CN102416027B (en) * | 2011-12-01 | 2015-11-25 | 徐州医学院 | The application of active substance in treatment cardiovascular and cerebrovascular diseases medicament of Semen Ginkgo active component extraction separating method and extraction |
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| Publication number | Publication date |
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| CN1301988C (en) | 2007-02-28 |
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Application publication date: 20040922 Assignee: Hubei Benxing Chemical Co., Ltd. Assignor: Sanjiangyuan Pharmaceutical Co., Ltd., Suizhou City Contract record no.: 2010420000065 Denomination of invention: Method of extracting terpene lactone from folium ginkgo leaves and product Granted publication date: 20070228 License type: Exclusive License Record date: 20100527 |
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Effective date of registration: 20160603 Address after: 441300, No. 9, hi tech Industrial Park, Hubei, Suizhou Patentee after: Hubei Benxing Chemical Co., Ltd. Address before: 441300 eight mile fork, north of traffic road, Hubei, Suizhou Patentee before: Sanjiangyuan Pharmaceutical Co., Ltd., Suizhou City |
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