CN1594319A - Process for extracting ginkgolide, ginkgolide injection and process for preparing same - Google Patents
Process for extracting ginkgolide, ginkgolide injection and process for preparing same Download PDFInfo
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- CN1594319A CN1594319A CN 200410041120 CN200410041120A CN1594319A CN 1594319 A CN1594319 A CN 1594319A CN 200410041120 CN200410041120 CN 200410041120 CN 200410041120 A CN200410041120 A CN 200410041120A CN 1594319 A CN1594319 A CN 1594319A
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Abstract
The invention discloses a process for extracting ginkgolide, ginkgolide injection and process for preparing same, wherein the extracting process consists of disintegrating the ginkgo leaves, leaching by diluted acetone solution, recovering acetone, removing impurities, extracting and purifying with acetic ether, removing impurities with sodium acetate again, reclaiming acetic ether, recrystallizing in ethanol or methanol, filtering, low temperature drying, solubilizing the bilobalide with hydroxypropyl-beta-cyclodextrin to obtain the bilobalide injection.
Description
Technical field
The invention belongs to field of traditional Chinese medicine pharmacy, particularly relate to a kind of bilobalide extraction process and bilobalide injection and preparation method thereof.
Background technology
Sought potent PAF (platelet activation factor) antagonist and be one of great direction of new drug research since the eighties in last century.PAF participates in many pathophysiological processes in vivo, acts on widely, and activity is very big, has found that PAF plays an important role in the pathologic processes such as shock that thrombosis, asthma, organ-graft refection, acute inflammation, heart allergy, intracellular toxin cause.In the research of PAF antagonist, the ginkgolide compound that screens from natural product is that activity is the strongest, estimate maximum natural products, pharmacology and clinical study also show, ginkgolide compound is state-of-the-art PAF antagonist, and wherein the selectivity of Ginkgolide B antagonism paf receptor and activity are the strongest.Bilobalide is as highly narrow spectrum paf receptor blocker, its active strong and weak IC
50Be respectively: Ginkgolide B 0.25Mm＞Ginkgolide A 0.74Mm＞ginkalide C 7.1Mm.Bilobalide mainly shows as the central nervous system effect can stop the damage that causes after the cerebral ischemia, can obviously improve cerebral ischemic condition, and cerebral edema, electrolyte disturbance, inflammatory cell infiltration that ischemic is caused have remarkable restraining effect.Bilobalide can anticoagulant, and blood viscosity lowering improves ischemic patient's microcirculation, reduces thrombosis; The bilobalide stabilizing cell membrane, the osmosis of minimizing Angiotensin; Have antianaphylaxis, anti-inflammatory, Antishock function, the rejection of ischemic injuries and organ transplantation is also had provide protection.In addition, all right SOD activity improving of bilobalide is eliminated free radical, is delayed senility.But present bilobalide extraction process cost height, yield is low, active substance content is few, and because bilobalide solubleness in water is low, is difficult for making the injection liquid of high density, has limited its effective application.
Summary of the invention
The extraction process that the purpose of this invention is to provide the bilobalide that a kind of cost is low, yield is high.
Another object of the present invention provides the bilobalide injection of a kind of concentration height, Heat stability is good.
A further object of the invention provides the preparation method of above-mentioned bilobalide injection.
Extraction solvent used in the bilobalide extraction process of the present invention is rare acetone solution, ethyl acetate, in the technology with sherwood oil and sodium acetate soln removal of impurities; Use ethyl alcohol recrystallization.This process using solvent method.
The present invention has selected the solubilizing agent of hydroxypropyl-beta-cyclodextrin as bilobalide for use, can improve the solubleness of bilobalide in water greatly, can make transfusion and use, solve the heavy dose of use problem of bilobalide, also make the thermostability of bilobalide in water obtain bigger raising simultaneously.Adding an amount of isotonic regulator in transfusion makes with blood etc. and oozes.For improving the long-term stability of placing of transfusion, can also add an amount of sequestrant.
The present invention is realized by following scheme:
A kind of extraction process of bilobalide is characterized in that comprising the following step:
Take by weighing a certain amount of Ginkgo Leaf, pulverize, the rare acetone solution temperature lixiviate that adds the several times amount is got, and uses the removal of impurities of removal of impurities solvent behind the recovery acetone, the ethyl acetate extraction purifying, and sodium-acetate is removal of impurities again, reclaims vinyl acetic monomer, and recrystallization in ethanol or the methyl alcohol filters cryodrying.
Described extraction process, the rare acetone extraction of Ginkgo Leaf wherein, its concentration is 20%～70%, and it is 30～55 ℃ that temperature is soaked temperature, and the acetone consumption is 2～10 times of crude drug.
Described extraction process, the removal of impurities solvent can be normal hexane, hexanaphthene, chloroform, sherwood oil (30～120 ℃) in its extraction process.
Described extraction process, the abstraction purification solvent is ethyl acetate, 2-15% sodium acetate soln or sodium hydrogen carbonate solution in its extraction process.
Described extraction process, the bilobalide recrystallization solvent is 40～95% ethanol or methyl alcohol in its extraction process, and is dry under the 40-80 ℃ of temperature.
A kind of bilobalide injection, it is the aqueous solution that adopts the hydroxypropyl-beta-cyclodextrin solubilising to make to bilobalide.
Described bilobalide injection, it also contains sequestrant.
Described bilobalide injection, wherein sequestrant can be disodium ethylene diamine tetraacetate or Sormetal.
Described bilobalide injection, it also contains isotonic regulator.
Described bilobalide injection, wherein isotonic regulator can be sodium-chlor or glucose.
Above-mentioned arbitrary bilobalide injection contains in every 100ml preparation:
Bilobalide 0.001-0.1g hydroxypropyl-beta-cyclodextrin 0.01-10g isotonic regulator 0.5-5g sequestrant 0.01-0.05g.
The preparation method of described bilobalide injection, comprise dissolving, activated carbon treatment, coarse filtration, constant volume, smart filter, packing, sterilization process, it is characterized in that hydroxypropyl-beta-cyclodextrin is added in the water for injection, after the stirring and dissolving, add bilobalide again, stir and be heated to dissolving, add isotonic regulator and sequestrant stirring and dissolving then, add coarse filtration after the activated carbon treatment, add smart filter behind the injection water constant volume, packing, pressure sterilizing.
Advantage of the present invention:
Adopt this law production bilobalide advantage as follows:
1, this law adopts solvent method to extract bilobalide, cuts off domestic resin column commonly used at present and other sorbent materials and produces bilobalide.This law is simple to operate, pollute less, cost is low.
2, this law is extracted the bilobalide yield up to more than 0.1%, and only is about 0.07% with other extracting method bilobalide yield.
3, this law extraction bilobalide content reaches more than 90%, and wherein Ginkgolide B content reaches 50%, and Ginkgolide B content can only reach about 30% in the like product.
4, major impurity separating Ginkgo phenolic acids content is less than 5ppm in this law extraction bilobalide, and phenolic acids content is higher than 100ppm in the bilobalide of additive method production.
5, hydroxypropyl-beta-cyclodextrin is a beta-cyclodextrin derivative, and good water solubility is nontoxic non-stimulated, can be used as the used for intravenous injection auxiliary material, and multiple medicine is had solubilising and clathration.The present invention utilizes hydroxypropyl-beta-cyclodextrin to the bilobalide solubilising, not only solved the water-soluble problem of bilobalide under non-alkaline condition, make bilobalide solubleness maximum under non-alkaline condition can reach 1mg/ml, and can improve the thermostability of the bilobalide aqueous solution, make the injection liquid pressure sterilizing become possibility, the injection liquid of preparation is safer, more stable, helps clinical application.
Bilobalide injection of the present invention is according to clinical needs, solved the heavy dose of problem of using of bilobalide, simplified operation, easy to use, avoided extracting the middle-chain of injecting sodium-chlor or glucose infusion liquid by little envelope pin, stop the crossed contamination in the medication process, improved medicine quality, ensured drug safety.Bilobalide transfusion of the present invention can be made all size, directly selects for use for the clinician.
This transfusion appearance colorless is clear and bright, and every index all meets " Chinese Pharmacopoeia version (second one) in 2000 " appendix IB relevant regulations.
6, preparation method's cost of bilobalide injection of the present invention is low, simple.
Embodiment
The invention will be further elaborated by the following examples.
Embodiment 1
The extraction process of bilobalide: take by weighing Ginkgo Leaf 100g and pulverize, the 70% acetone solution temperature lixiviate that adds 4 times of amounts is got, and temperature is 30 ℃, and lixiviate 5 hours was stirred once every 10 minutes, filtered, and got filtrate I.The dregs of a decoction continue 70% acetone solution temperature lixiviate of 4 times of amounts of adding to be got, and temperature is 30 ℃, and lixiviate 1 hour is filtered, and gets filtrate II.The dregs of a decoction continue to add the 70% acetone solution temperature lixiviate of 3 times of amounts to be got, and temperature is 30 ℃, and lixiviate 1 hour is filtered, and gets filtrate II I, and the dregs of a decoction discard.Merge No. three times extracting solution, reclaim 1/4 amount of acetone, place to about cumulative volume.Filter above-mentioned concentrated solution and use sherwood oil (30 ℃, consumption is 2: 1) removal of impurities 4 times, water extracts 3 times with vinyl acetic monomer (consumption is 2: 1); Vinyl acetic monomer liquid reclaims vinyl acetic monomer with 8% sodium acetate soln (consumption is 2: 1) washing, and residue 70% dissolve with ethanol is placed crystallization, filtration, 70 ℃ of vacuum-drying (0.07～0.08MPa), promptly.
Embodiment 2
The extraction process of bilobalide: take by weighing Ginkgo Leaf 200g and pulverize, the 50% acetone solution temperature lixiviate that adds 7 times of amounts is got, and temperature is 40 ℃, and lixiviate 6 hours was stirred once every 10 minutes, filtered, and got filtrate I.The dregs of a decoction continue 50% acetone solution temperature lixiviate of 5 times of amounts of adding to be got, and temperature is 40 ℃, and lixiviate 1 hour is filtered, and gets filtrate II.The dregs of a decoction continue to add the 50% acetone solution temperature lixiviate of 3 times of amounts to be got, and temperature is 40 ℃, and lixiviate 1 hour is filtered, and gets filtrate II I, and the dregs of a decoction discard.Merge No. three times extracting solution, reclaim 1/4 amount of acetone, place to about cumulative volume.Filter above-mentioned concentrated solution and use sherwood oil (120 ℃, consumption is 3: 1) removal of impurities 5 times, water extracts 4 times with vinyl acetic monomer (consumption is 3: 1); Vinyl acetic monomer liquid reclaims vinyl acetic monomer with 10% sodium acetate soln (consumption is 3: 1) washing, and residue 50% dissolve with ethanol is placed crystallization, filtration, 40 ℃ of vacuum-drying (0.07～0.08MPa), promptly.
Embodiment 3
The extraction process of bilobalide: take by weighing Ginkgo Leaf 200g and pulverize, the 60% acetone solution temperature lixiviate that adds 5 times of amounts is got, and temperature is 50 ℃, and lixiviate 8 hours was stirred once every 10 minutes, filtered, and got filtrate I.The dregs of a decoction continue 60% acetone solution temperature lixiviate of 5 times of amounts of adding to be got, and temperature is 50 ℃, and lixiviate 2 hours is filtered, and gets filtrate II.The dregs of a decoction continue to add the 60% acetone solution temperature lixiviate of 4 times of amounts to be got, and temperature is 50 ℃, and lixiviate 2 hours is filtered, and gets filtrate II I, and the dregs of a decoction discard.Merge No. three times extracting solution, reclaim 1/4 amount of acetone, place to about cumulative volume.Filter above-mentioned concentrated solution also with hexanaphthene (consumption is 3: 1) removal of impurities 3 times, water extracts 2 times with vinyl acetic monomer (consumption is 3: 1); Vinyl acetic monomer liquid reclaims vinyl acetic monomer with 15% sodium acetate soln (consumption is 3: 1) washing, and residue 95% dissolve with ethanol is placed crystallization, filtration, 50 ℃ of vacuum-drying (0.07～0.08MPa), promptly.
Embodiment 4
The extraction process of bilobalide: take by weighing Ginkgo Leaf 200g and pulverize, the 20% acetone solution temperature lixiviate that adds 10 times of amounts is got, and temperature is 55 ℃, and lixiviate 6 hours was stirred once every 10 minutes, filtered, and got filtrate I.The dregs of a decoction continue 20% acetone solution temperature lixiviate of 8 times of amounts of adding to be got, and temperature is 55 ℃, and lixiviate 1 hour is filtered, and gets filtrate II.The dregs of a decoction continue to add the 20% acetone solution temperature lixiviate of 6 times of amounts to be got, and temperature is 55 ℃, and lixiviate 1 hour is filtered, and gets filtrate II I, and the dregs of a decoction discard.Merge No. three times extracting solution, reclaim 1/6 amount of acetone, place to about cumulative volume.Filter above-mentioned concentrated solution also with chloroform (consumption is 4: 1) removal of impurities 6 times, water extracts 6 times with vinyl acetic monomer (consumption is 4: 1); Vinyl acetic monomer liquid reclaims vinyl acetic monomer with 2% sodium acetate soln (consumption is 4: 1) washing, and residue 40% dissolve with ethanol is placed crystallization, filtration, 80 ℃ of vacuum-drying (0.07～0.08MPa), promptly.
Embodiment 5
Bilobalide sodium chloride injection and preparation method: take by weighing hydroxypropyl-beta-cyclodextrin 50g and add in the 5000ml water for injection, after the stirring and dissolving, add bilobalide 2.5g according to specification, stir and be heated to dissolving, add sodium-chlor 89g and Sormetal 1g stirring and dissolving, add gac 2.5g, 80 ℃ of insulations were also stirred 10 minutes, and the coarse filtration carbon removal adds the injection water to 10000ml, mixing, with 0.22 μ m filtering with microporous membrane, gained solution is sub-packed in the 100ml infusion bottle, and every bottle contains bilobalide 25mg, sterilized 30 minutes for 115 ℃, promptly get the bilobalide transfusion.
Embodiment 6
Bilobalide glucose injection and preparation method: production technique changes sodium-chlor 89g among the embodiment 5 into glucose 494g with embodiment 5.
Embodiment 7
Bilobalide sodium chloride injection and preparation method: take by weighing hydroxypropyl-beta-cyclodextrin 500g and add in the 5000ml water for injection, after the stirring and dissolving, add bilobalide 5g according to specification, stir and be heated to dissolving, add sodium-chlor 89g and disodium ethylene diamine tetraacetate 1g stirring and dissolving, add gac 2.5g, 80 ℃ of insulations were also stirred 10 minutes, and the coarse filtration carbon removal adds the injection water to 10000ml, mixing, with 0.22 μ m filtering with microporous membrane, gained solution is sub-packed in the 100ml infusion bottle, and every bottle contains bilobalide 50mg, sterilized 30 minutes for 115 ℃, promptly get the bilobalide transfusion.
Embodiment 8
Bilobalide glucose injection and preparation method: production technique changes sodium-chlor 89g among the embodiment 7 into glucose 494g with embodiment 7.
Embodiment 9
Bilobalide sodium chloride injection and preparation method: take by weighing hydroxypropyl-beta-cyclodextrin 800g and add in the 5000ml water for injection, after the stirring and dissolving, add bilobalide 8g according to specification, stir and be heated to dissolving, add sodium-chlor 89g and Sormetal 1g stirring and dissolving, add gac 2.5g, 80 ℃ of insulations were also stirred 10 minutes, and the coarse filtration carbon removal adds the injection water to 10000ml, mixing, with 0.22 μ m filtering with microporous membrane, gained solution is sub-packed in the 100ml infusion bottle, and every bottle contains bilobalide 80mg, sterilized 30 minutes for 115 ℃, promptly get the bilobalide transfusion.
Embodiment 10
Bilobalide glucose injection and preparation method: production technique changes sodium-chlor 89g among the embodiment 9 into glucose 494g with embodiment 9.
Embodiment 11
Bilobalide sodium chloride injection and preparation method: take by weighing hydroxypropyl-beta-cyclodextrin 1000g and add in the 5000ml water for injection, after the stirring and dissolving, add bilobalide 10g according to specification, stir and be heated to dissolving, add sodium-chlor 89g and Sormetal 1g stirring and dissolving, add gac 2.5g, 80 ℃ of insulations were also stirred 10 minutes, and the coarse filtration carbon removal adds the injection water to 10000ml, mixing, with 0.22 μ m filtering with microporous membrane, gained solution is sub-packed in the 100ml infusion bottle, and every bottle contains bilobalide 100mg, sterilized 30 minutes for 115 ℃, promptly get the bilobalide transfusion.
Embodiment 12
Bilobalide glucose injection and preparation method: production technique changes sodium-chlor 89g among the embodiment 11 into glucose 494g with embodiment 11.
Claims (12)
1, a kind of extraction process of bilobalide is characterized in that comprising the following step:
Take by weighing a certain amount of Ginkgo Leaf, pulverize, the rare acetone solution temperature lixiviate that adds the several times amount is got, and uses the removal of impurities of removal of impurities solvent behind the recovery acetone, the ethyl acetate extraction purifying, and sodium-acetate is removal of impurities again, reclaims vinyl acetic monomer, and recrystallization in ethanol or the methyl alcohol filters cryodrying.
2, extraction process according to claim 1 is characterized in that the rare acetone extraction of Ginkgo Leaf, and its concentration is 20%～70%, and it is 30～55 ℃ that temperature is soaked temperature, and the acetone consumption is 2～10 times of crude drug.
3, extraction process according to claim 1 is characterized in that the removal of impurities solvent can be normal hexane, hexanaphthene, chloroform or sherwood oil in the extraction process.
4, extraction process according to claim 1 is characterized in that the abstraction purification solvent is ethyl acetate, 2-15% sodium acetate soln or sodium hydrogen carbonate solution in the extraction process.
5, extraction process according to claim 1 is characterized in that the bilobalide recrystallization solvent is 40～95% ethanol or methyl alcohol in the extraction process, and is dry under the 40-80 ℃ of temperature.
6, a kind of bilobalide injection is characterized in that it is the aqueous solution that adopts the hydroxypropyl-beta-cyclodextrin solubilising to make to bilobalide.
7, bilobalide injection according to claim 6 is characterized in that also containing sequestrant.
8, bilobalide injection according to claim 7 is characterized in that sequestrant can be disodium ethylene diamine tetraacetate or Sormetal.
9, bilobalide injection according to claim 6 is characterized in that also containing isotonic regulator.
10, bilobalide injection according to claim 9 is characterized in that isotonic regulator can be sodium-chlor or glucose.
11,, it is characterized in that containing in every 100ml preparation according to the arbitrary described bilobalide injection of claim 6～10:
Bilobalide 0.001-0.1g hydroxypropyl-beta-cyclodextrin 0.01-10g isotonic regulator 0.5-5g sequestrant 0.01-0.05g.
12, the preparation method of the described bilobalide injection of claim 6～11, comprise dissolving, activated carbon treatment, coarse filtration, constant volume, smart filter, packing, sterilization process, it is characterized in that hydroxypropyl-beta-cyclodextrin is added in the water for injection, after the stirring and dissolving, add bilobalide again, stir and be heated to dissolving, add isotonic regulator and sequestrant stirring and dissolving then, add coarse filtration after the activated carbon treatment, add smart filter behind the injection water constant volume, packing, pressure sterilizing.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1317283C (en) * | 2005-07-29 | 2007-05-23 | 四川恩威中医药研究开发有限公司 | Bilobalide extraction and purification process |
| CN1830981B (en) * | 2006-04-17 | 2010-05-12 | 四川科伦药业股份有限公司 | Emulsum injection for treating cerebrovascular diseases, and its preparation art |
| CN102491983A (en) * | 2011-12-20 | 2012-06-13 | 徐州康泰生物制品有限公司 | Method for preparing high-purity ginkgolides |
| CN103159780A (en) * | 2013-03-27 | 2013-06-19 | 徐州工业职业技术学院 | Method for extracting ginkgolide from gingko velamina |
| US9084755B2 (en) | 2012-04-23 | 2015-07-21 | Chengdu Baiyu Technology Pharmacy Co., Ltd. | Method for extracting and separating ginkgolides |
| CN107773763A (en) * | 2016-08-25 | 2018-03-09 | 江苏康缘药业股份有限公司 | Bilobalide K beta cyclodextrin clathrate and preparation method thereof |
| CN109020993A (en) * | 2018-09-04 | 2018-12-18 | 湖北工程学院 | A method of extracting ginkgolides from ginkgo leaf |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102174052B (en) * | 2011-03-23 | 2014-10-01 | 晨光生物科技集团天津有限公司 | Method for extracting and refining ginkgolide |
-
2004
- 2004-06-30 CN CN 200410041120 patent/CN1263763C/en active Active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1317283C (en) * | 2005-07-29 | 2007-05-23 | 四川恩威中医药研究开发有限公司 | Bilobalide extraction and purification process |
| CN1830981B (en) * | 2006-04-17 | 2010-05-12 | 四川科伦药业股份有限公司 | Emulsum injection for treating cerebrovascular diseases, and its preparation art |
| CN102491983A (en) * | 2011-12-20 | 2012-06-13 | 徐州康泰生物制品有限公司 | Method for preparing high-purity ginkgolides |
| US9084755B2 (en) | 2012-04-23 | 2015-07-21 | Chengdu Baiyu Technology Pharmacy Co., Ltd. | Method for extracting and separating ginkgolides |
| CN103159780A (en) * | 2013-03-27 | 2013-06-19 | 徐州工业职业技术学院 | Method for extracting ginkgolide from gingko velamina |
| CN107773763A (en) * | 2016-08-25 | 2018-03-09 | 江苏康缘药业股份有限公司 | Bilobalide K beta cyclodextrin clathrate and preparation method thereof |
| CN109020993A (en) * | 2018-09-04 | 2018-12-18 | 湖北工程学院 | A method of extracting ginkgolides from ginkgo leaf |
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| CN1263763C (en) | 2006-07-12 |
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