CN101502539A - Method for preparing ginkgo leaf extract cyclodextrin inclusion compound and preparation - Google Patents
Method for preparing ginkgo leaf extract cyclodextrin inclusion compound and preparation Download PDFInfo
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- CN101502539A CN101502539A CNA2009100740005A CN200910074000A CN101502539A CN 101502539 A CN101502539 A CN 101502539A CN A2009100740005 A CNA2009100740005 A CN A2009100740005A CN 200910074000 A CN200910074000 A CN 200910074000A CN 101502539 A CN101502539 A CN 101502539A
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Abstract
The invention relates to a preparation prepared by ginkgo biloba extract, in particular to a ginkgo biloba extract cyclodextrin inclusion compound and a preparation method of the preparation. The problems of poor solubility, low dissolution rate, poor storage performance and the like in a variety of preparations of the ginkgo biloba extract in the prior art can be solved. The method comprises the steps of adding water in 2-hydroxypropyl-beta-cyclodextrin, heating and dissolving to prepare 2-hydroxypropyl-beta-cyclodextrin solution, then using 95 percent ethanol for dissolving the ginkgo biloba extract, dripping ginkgo biloba extract-ethanol solution to the 2-hydroxypropyl-beta-cyclodextrin solution under the stirring state, lasting the process for 1 hour, stopping heating after completing the dripping, continuously stirring for 1-3 hours; stopping stirring, standing reaction liquid and filtering for preparation. The ginkgo biloba extract 2-hydroxypropyl-beta-cyclodextrin inclusion compound and a variety of preparations can greatly improve the problem of small solubility of the ginkgo biloba extract in the water and improve the stability of the ginkgo biloba extract in the water.
Description
Technical field
The present invention relates to a kind of preparation of Folium Ginkgo extract preparation, be specially the preparation method of a kind of ginkgo leaf extract cyclodextrin inclusion compound and preparation.
Background technology
Contain effective ingredient such as a large amount of ginkgetins, Ginkgo biloba terpenes lactone in the Folium Ginkgo, can improve human body respiration, improve sleep quality, life-time service can prevent and treat cardiovascular disease. prevent hypertension that the adult causes because of the vessel aging, apoplexy, diabetes etc., can make the adult especially keep the natural materials of normal cardiac output and normal nervous function period, make the people keep normal cell life cycle as far as possible person in middle and old age.
Modern study is found, flavone compound is for improving the heart, cerebral blood circulation in the Folium Ginkgo extract, reduce serum cholesterol, lax bronchial smooth muscle has better curative effect, and treatment coronary atherosclerotic heart disease, myocardial infarction, expansion of cerebral vascular, cerebral blood flow increasing amount, treatment ischemic encephalopathy are had good effect.The Folium Ginkgo terpene lactones compounds is the strongest PAF (platelet activating factor) antagonist of activity that extracts from natural drug, can stop the damage that causes after the cerebral ischemia to the central nervous system, can obviously improve cerebral ischemic condition.Bilobalide can anticoagulant, and blood viscosity lowering improves ischemia patient's microcirculation, reduces thrombosis, also has antiallergic, antiinflammatory, Antishock function simultaneously, and the rejection of ischemic injuries and organ transplantation is had protective effect.
The preparation that contains Folium Ginkgo extract at present mainly contains tablet, capsule, small-volume injection, the ubiquity water solublity is bad in numerous dosage forms, with precipitation problem such as produce, darken is arranged in the storage process, also have the low problem of dissolution for tablet and capsule.The present invention adopts the 2-HP-that Folium Ginkgo extract is carried out enclose, cooperate each dosage form to add corresponding auxiliary material again and make preparation, thereby improved the dissolubility of preparation in water that contains Folium Ginkgo extract greatly, made the physiologically active of effective ingredient in the product and physicochemical property reliable and stable.
Summary of the invention
The present invention is problem such as the poor solubility, the dissolution that exist in the various preparations of the Folium Ginkgo extract that exists in the prior art are low, poor storage performance and the preparation method of a kind of ginkgo leaf extract cyclodextrin inclusion compound and preparation thereof is provided in order to solve.
The present invention is realized by following technical scheme, a kind of ginkgo leaf extract cyclodextrin inclusion compound is prepared by following method, the 2-HP-added water and be heated to 50-60 ℃ make its whole dissolvings, make 2-HP-solution, mass concentration is 5-10%; Folium Ginkgo extract is used 95% dissolve with ethanol again, under stirring the Folium Ginkgo extract alcoholic solution is added drop-wise in the 2-HP-solution, process continues 1 hour, stops heating after adding, and continues to stir and keeps 1-3 hour; Stop to stir reactant liquor is left standstill, filters promptly.Stir and adopt electric mixing device, rotating speed is 40-80 rev/min, and the mass ratio that feeds intake of Folium Ginkgo extract and 2-HP-is 1:2-4.
Method for preparing obtains the ginkgo leaf extract cyclodextrin inclusion compound pharmaceutical solutions, this pharmaceutical solutions and different pharmaceutic adjuvant preparations, adopt corresponding technology can be prepared into multiple dosage form, as solid preparation (comprising tablet, capsule, granule etc.), injection (comprising small-volume injection, bulk capacity injection, aseptic powder injection, freeze-dried powder etc.).
The present invention has carried out a large amount of tests in inclusion method, influence factor, stability, the safety of research cyclodextrin and Folium Ginkgo extract, now the research situation is summarized as follows:
Determining of cyclodextrin: we from numerous cyclodextrin products, by analysis, screening, test, selected alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin, 2-HP-as main research to picture.Its dissolubility is as shown in the table:
Table 1 alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin, 2-HP-dissolubility
| Title | Alpha-cyclodextrin | Beta-schardinger dextrin- | Gamma-cyclodextrin | The 2-HP- |
| Dissolubility (g/L, 25 ℃) | 145 | 18.5 | 232 | 750 |
As can be seen, the beta-schardinger dextrin-dissolubility is minimum from the dissolubility of alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin, 2-HP-, and the alpha-cyclodextrin supply is less, be difficult to obtain, gamma-cyclodextrin is comparatively desirable, but price is more expensive, and production application is less.Therefore we have selected the 2-HP-to carry out researchs such as inclusion method as the raw material that carries out enclose with Folium Ginkgo extract.
Inclusion method research: the method for cyclodextrin inclusion compound is a lot, and we are actual from producing, and adopts paddling process, supercritical ultrasonics technology, polishing, and three kinds of inclusion methods have been carried out odds.
Paddling process is to use electric mixing device, the 2-HP-added water and be heated to 50-60 ℃ make whole dissolvings, with Folium Ginkgo extract 95% dissolve with ethanol, slowly splash in the 2-HP-solution and stirred 1 hour, stop heating, continue to stir and kept 4 hours, reactant liquor leaves standstill, filters, is drying to obtain.
Supercritical ultrasonics technology is earlier the 2-HP-to be added the water heating to make whole dissolvings, with Folium Ginkgo extract 95% dissolve with ethanol, the two is mixed obtain mixing material, used the ultrasonic disruption instrument then ultrasonic 5 minutes, intensity 14, replace mixing power, stop ultrasonic reactant liquor being left standstill, filter, is drying to obtain.
Polishing is that the 2-HP-is placed mortar, add suitable quantity of water moistening after, add the Folium Ginkgo extract alcoholic solution, fully mixed grinding becomes pasty state, and constantly adds water make dissolving in mortar, and reactant liquor is left standstill, filters, is drying to obtain.
Result of the test, ginkgetin and lactone content in the clathrate that the mensuration distinct methods makes, paddling process〉ultrasonic method〉polishing.Productivity ratio, polishing〉ultrasonic method paddling process.Polishing output is the highest, but drug content is minimum, checks that the 2-HP-that has does not form clathrate, and it is the highest that the clathrate that paddling process makes contains the principal agent amount, and after the balance, we have selected to use paddling process.
Optimum charging ratio is selected: with different rate of charges, adopt paddling process to carry out enclose, with Folium Ginkgo extract: the 2-HP-is 1:1,1:2,1:4,1:8,1:10,1:20 carries out enclose, survey ginkgetin and lactone content in the clathrate, the result is with 1:2, the rate of charge of 1:4 is more suitable, 1:1 feeds intake, it is lower to record content, illustrate that enclose is incomplete, 1:8,1:10,1:20 feeds intake and 1:2,1:4 relatively, content differs and is not clearly, and illustrating feeds intake between the 1:2-1:4 can reach best enclose effect, and changes of contents is not obvious along with the increase of ingredient proportion, declaratives 2-HP-is excessive for feeding intake, have neither part nor lot in enclose, invalid composition, so we have determined that the optimum charging ratio of Folium Ginkgo extract and 2-HP-is 1:2-4.Ginkgetin and lactone amount and inclusion rate are as shown in the table in the different rate of charge clathrates.
Ginkgetin and lactone content and inclusion rate in the different rate of charge clathrates of table 2
The selection of mixing time: paddling process also has much relations with mixing time, we are that 1:2 feeds intake by Folium Ginkgo extract and 2-HP-, adopt stirring means to prepare clathrate, stir 1 respectively, 2,4,5,10 hours, make clathrate and survey ginkgetin and lactone content, the result shows to stir 2-4 hour for well, bilobalide content was low in 1 hour, illustrate and do not have abundant enclose, 5,10 hours content and 2,4 hours content differs very little, illustrates that Folium Ginkgo extract prepares clathrate with stirring means and can finish enclose in 2-4 hour in stirring.
Preparation technology determines: so we have determined that Folium Ginkgo extract and 2-HP-prepare the preparation technology of clathrate: the 2-HP-is added water and be heated to 50-60 ℃ and make its whole dissolvings, make 2-HP-solution, mass concentration is 5-10%; Folium Ginkgo extract is used 95% dissolve with ethanol again, under stirring the Folium Ginkgo extract alcoholic solution is added drop-wise in the 2-HP-solution, process continues 1 hour, stops heating after adding, and continues to stir and keeps 1-3 hour; Stop to stir reactant liquor is left standstill, filters promptly.Stir and adopt electric mixing device, rotating speed is 40-80 rev/min, and the mass ratio that feeds intake of Folium Ginkgo extract and 2-HP-is 1:2-4.
The research of preparation technology's repeatability: we adopt above-mentioned definite preparation technology, with Folium Ginkgo extract and 2-HP-is that 1:2 feeds intake, electronic stirring 4 hours, 60 rev/mins of rotating speeds, 6 batches of clathrates have been prepared, productive rate, active constituent content to clathrate are analyzed, and the result shows that this technology repeatability is good, illustrate that preparation condition is suitable, reliable.Ginkgetin and bilobalide amount and inclusion rate measurement result are as follows in the clathrate.
Ginkgetin and lactone content and inclusion rate in table 3 clathrate
Clathrate and pharmaceutic adjuvant preparation that the present invention adopts above-mentioned preparation method to obtain, and adopt certain method can be prepared into multiple dosage form, as solid preparation (comprising tablet, capsule, granule etc.), injection (comprising small-volume injection, bulk capacity injection, aseptic powder injection, freeze-dried powder etc.).When being used to prepare small-volume injection, bulk capacity injection and lyophilized injectable powder, directly prepare drying-free after can filtering, filtration can be adopted sucking filtration, ultrafiltration or filter with the filter of 0.22 μ m.To carry out drying when being used to prepare solid preparation, injectable powder, dry employing vacuum decompression drying or lyophilization.
The present invention prepares the method for small-volume injection: at first 2-4 part 2-HP-is added the water heating and make whole dissolvings, make 2-HP-solution; Secondly with 1 part of Folium Ginkgo extract 95% dissolve with ethanol, slowly splash in the 2-HP-solution and stirred 1 hour; Stop heating, continue to stir and kept 1-3 hour; Stir and adopt electric mixing device, rotating speed is 40-80 rev/min.Stop to stir reactant liquor was left standstill 2 hours, the filter with 0.22 μ m to the room temperature filters, and adds an amount of medicinal charcoal, adds and prepares required water for injection, and heated and boiled 30 minutes is filtered after the cooling, with the PH regulator pH value is adjusted to 4.5-5.8.After being filtered to clarification, fill is in the cillin bottle of 10ml sterilization, and lid is rolled in lyophilization, that is, or embedding seals in the 10ml ampoule, sterilizes, promptly.
The safety research of injection: injection is the highest to security requirement in multiple dosage form, therefore we make injection with above-mentioned preparation method and have carried out zoopery, by various dose, different way of administration is a laboratory animal with mice, rat, and maximum dose level intraperitoneal and intravenously administrable have reached 10.0g/kg, the behavior of observation animal, dietary habit, nephrotoxicity etc. after the administration, all have no adverse effect, vital sign is normal, illustrates that the injection that this product makes is safe.Its experimental result is as shown in the table.
Table 4 zoopery result
The stability study of injection: in order to verify the stability of the prepared injection of the present invention, we select same batch of injection to test under 60 ℃, 18-26 ℃, 0-4 ℃, 4576lx illumination condition.Result such as following table: table 5 injection stability test result
| Condition | Time (my god) | Clarity | Differentiate | The content of ginkgetin (mg/ml) | The content of bilobalide (mg/ml) |
| 60℃ | 0 30 90 180 | Clarification clarification clarification clarification | Positive | 0.847 0.847 0.845 0.842 | 0.223 0.222 0.220 0.218 |
| 18-26℃ | 0 30 90 180 | Clarification clarification clarification clarification | Positive | 0.848 0.847 0.844 0.842 | 0.224 0.223 0.221 0.220 |
| 0-4℃ | 0 30 90 180 | Clarification clarification clarification clarification | Positive | 0.850 0.848 0.847 0.845 | 0.224 0.223 0.222 0.221 |
| 4576lx | 0 30 90 180 | Clarification clarification clarification clarification | Positive | 0.852 0.850 0.846 0.843 | 0.227 0.225 0.223 0.221 |
Through experimental results show that repeatedly: Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion, improved the very little problem of Folium Ginkgo extract dissolubility in water greatly, and improved the stability of Folium Ginkgo extract in water when making injection.
The specific embodiment
Embodiment 1
Preparation Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion tablet
Folium Ginkgo extract 10g
95% ethanol 10ml
2-HP-20g
Starch 80g
Carboxymethyl starch sodium 10g
10% gelatinized corn starch 200g
Magnesium stearate 5g
Getting 2-HP-20g adds 380g water and is heated to 50 ℃ and make its dissolving, make 2-HP-solution, get Folium Ginkgo extract 10g and be dissolved in the 10ml95% ethanol, then the Folium Ginkgo extract alcoholic solution is slowly splashed in the 2-HP-solution and continue and stirred 1 hour; Stop heating, continue to stir and kept 1-3 hour, stir and adopt electric mixing device, rotating speed is 40-80 rev/min; Stop to stir reactant liquor is left standstill, filter, the vacuum decompression drying promptly gets Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion.
Get 10g Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion, add 80g starch, the 10g carboxymethyl starch sodium, with blender with its mix homogeneously, and add 10% gelatinized corn starch 200g, make soft material, cross 16 mesh sieves and granulate 65-75 ℃ of oven dry, cross 18 mesh sieve granulate, add 5g magnesium stearate tabletting, make 225, get tablet.
Embodiment 2
Preparation Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion granule
Folium Ginkgo extract 10g
95% ethanol 10ml
2-HP-40g
Starch 200g
Icing Sugar 200g
20% gelatinized corn starch 200g
Getting 2-HP-40g adds 360g water and is heated to 55 ℃ and make its dissolving, make 2-HP-solution, get Folium Ginkgo extract 10g and be dissolved in the 10ml95% ethanol, then the Folium Ginkgo extract alcoholic solution is slowly splashed in the 2-HP-solution and stirred 1 hour; Stop heating, continue to stir and kept 1-3 hour, stir and adopt electric mixing device, rotating speed is 40-80 rev/min; Stop to stir reactant liquor is left standstill, filter, the vacuum decompression drying promptly gets Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion.
Get 10g Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion, add 200g starch, the 140g Icing Sugar with its mix homogeneously, and adds 20% gelatinized corn starch 200g with blender, makes soft material, crosses 14 mesh sieves and granulates.The 60g Icing Sugar is made 30% syrup, be sprayed on particle surface, 16 mesh sieve granulate are crossed in 65-75 ℃ of oven dry, and the packing of machine bag is made 225 bags, gets granule.
Embodiment 3
Preparation Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion small-volume injection
Folium Ginkgo extract 10g
95% ethanol 10ml
2-HP-30g
Thiourea 2.5g
Medicinal charcoal 2.5g
Water for injection 2400ml
At first the 30g2-HP-is added 350g water and be heated to 60 ℃ and make whole dissolvings, make 2-HP-solution; Secondly the 10g Folium Ginkgo extract is dissolved with 95% ethanol 10ml, slowly splash in the 2-HP-solution and stirred 1 hour; Stop heating, continue to stir and kept 1-3 hour; Stir and adopt electric mixing device, rotating speed is 40-80 rev/min.Stop to stir reactant liquor was left standstill 2 hours.Getting 100ml Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion to the room temperature filters with the filter of 0.22 μ m, add the 2.5g thiourea, 2.5g medicinal charcoal, add water for injection 1000ml, heated and boiled 30 minutes, filter after the cooling, add residue water for injection, pH value is adjusted to 4.5-5.8 with the PH regulator to 2500ml.After being filtered to clarification, embedding is made 250, promptly in the 10ml ampoule.
Embodiment 4
Preparation Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion bulk capacity injection
Folium Ginkgo extract 10g
95% ethanol 10ml
2-HP-20g
Sodium chloride 22.5g
Thiourea 2.5g
Medicinal charcoal 2.5g
Water for injection 2400ml
At first the 20g2-HP-is added 180g water and be heated to 50 ℃ and make whole dissolvings, make 2-HP-solution; Secondly the 10g Folium Ginkgo extract is dissolved with 95% ethanol 10ml, slowly splash in the 2-HP-solution and stirred 1 hour; Stop heating, continue to stir and kept 1-3 hour; Stir and adopt electric mixing device, rotating speed is 40-80 rev/min.Stop to stir reactant liquor was left standstill 2 hours.Getting 100ml Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion to the room temperature filters with the filter of 0.22 μ m, add the 2.5g thiourea, 2.5g medicinal charcoal, add water for injection 1000ml, heated and boiled 30 minutes, filter after the cooling, add residue water for injection, pH value is adjusted to 4.5-5.8 with the PH regulator to 2500ml.After being filtered to clarification, embedding is made 25 bottles, promptly in the 100ml infusion bottle.
Embodiment 5
Preparation Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion freezing-dried powder injection
Folium Ginkgo extract 10g
95% ethanol 10ml
2-HP-40g
Medicinal charcoal 2.5g
Water for injection 1580ml
At first the 40g2-HP-is added 360g water and be heated to 60 ℃ and make whole dissolvings, make 2-HP-solution; Secondly the 10g Folium Ginkgo extract is dissolved with 95% ethanol 10ml, slowly splash in the 2-HP-solution and stirred 1 hour; Stop heating, continue to stir and kept 1-3 hour; Stir and adopt electric mixing device, rotating speed is 40-80 rev/min.Stop to stir reactant liquor was left standstill 2 hours.Getting 100ml Folium Ginkgo extract 2-hydroxypropyl-beta-cyclodextrin inclusion to the room temperature filters with the filter of 0.22 μ m, 2.5g medicinal charcoal, add water for injection 1000ml, heated and boiled 30 minutes, filter after the cooling, add residue water for injection to 1680ml, pH value is adjusted to 4.5-5.8 with the PH regulator.After being filtered to clarification, sterile filling is in the cillin bottle of 10ml sterilization, and every 3.7ml makes 450, and lyophilization 30-48 hour, lid was rolled in tamponade, promptly.
Claims (3)
1, a kind of ginkgo leaf extract cyclodextrin inclusion compound is characterized in that: be by the 2-HP-being added water and be heated to 50-60 ℃ and make its whole dissolvings of following method preparation, make 2-HP-solution, mass concentration is 5-10%; Folium Ginkgo extract is used 95% dissolve with ethanol again, under stirring the Folium Ginkgo extract alcoholic solution is added drop-wise in the 2-HP-solution, process continues 1 hour, stops heating after adding, and continues to stir and keeps 1-3 hour; Stop to stir reactant liquor is left standstill, filters promptly.
2, ginkgo leaf extract cyclodextrin inclusion compound according to claim 1 is characterized in that: stir and adopt electric mixing device, rotating speed is 40-80 rev/min, and the mass ratio that feeds intake of Folium Ginkgo extract and 2-HP-is 1:2-4.
3, ginkgo leaf extract cyclodextrin inclusion compound according to claim 1 is characterized in that: its dosage form is tablet, capsule, granule, small-volume injection, bulk capacity injection, aseptic powder injection, freeze-dried powder.
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Cited By (4)
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| CN103877130A (en) * | 2013-09-17 | 2014-06-25 | 狄留庆 | Chinese medicinal composition for treating ischemic cerebral paralysis, application thereof to preparation of oral preparation and preparation of Chinese medicinal composition |
| CN107261157A (en) * | 2017-06-14 | 2017-10-20 | 苏州大学 | Inclusion compound of blueberry leaf melanin and its preparation method and application |
| 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 |
| CN109432440A (en) * | 2018-11-30 | 2019-03-08 | 佛山科学技术学院 | A kind of praziquantel hydroxypropyl cyclodextrin inclusion and its preparation method and application |
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| CN1233369C (en) * | 2003-06-23 | 2005-12-28 | 江苏扬子江药业集团有限公司 | Ginkgo leaf powder for injection and its prepn |
| CN1232251C (en) * | 2004-01-14 | 2005-12-21 | 江苏康缘药业股份有限公司 | Gingko lactone powder injection and its preparation method |
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- 2009-03-21 CN CN2009100740005A patent/CN101502539B/en active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103877130A (en) * | 2013-09-17 | 2014-06-25 | 狄留庆 | Chinese medicinal composition for treating ischemic cerebral paralysis, application thereof to preparation of oral preparation and preparation of Chinese medicinal composition |
| 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 |
| CN107261157A (en) * | 2017-06-14 | 2017-10-20 | 苏州大学 | Inclusion compound of blueberry leaf melanin and its preparation method and application |
| CN107261157B (en) * | 2017-06-14 | 2020-01-10 | 苏州大学 | Inclusion compound of vaccinium bracteatum leaf melanin and preparation method and application thereof |
| CN109432440A (en) * | 2018-11-30 | 2019-03-08 | 佛山科学技术学院 | A kind of praziquantel hydroxypropyl cyclodextrin inclusion and its preparation method and application |
| CN109432440B (en) * | 2018-11-30 | 2022-04-26 | 佛山科学技术学院 | Praziquantel hydroxypropyl cyclodextrin inclusion compound and preparation method and application thereof |
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