CN100425603C - Compound with anti cerebralischemia, myo cardialischemia and memory-improving functions, and its preparing method and use - Google Patents
Compound with anti cerebralischemia, myo cardialischemia and memory-improving functions, and its preparing method and use Download PDFInfo
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- CN100425603C CN100425603C CNB2006101137670A CN200610113767A CN100425603C CN 100425603 C CN100425603 C CN 100425603C CN B2006101137670 A CNB2006101137670 A CN B2006101137670A CN 200610113767 A CN200610113767 A CN 200610113767A CN 100425603 C CN100425603 C CN 100425603C
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Abstract
The invention provides a compound for resisting ischemia and myocardial ischemia and improving meromorphic function, adopting the roots of Pterocypsela elata, Pterocypsela laciniata and other Pterocypsela plants as raw materials, soaking with solvent at room temperature, vacuum-distilling the extractive, and making repeated silica gel column chromatography on the obtained extract and making it. And it and the pharmaceutically acceptable carriers can be made into tablets, capsules, soft capsules, pill drops, granules, oval solution, and syrups or injections. And it can reduce the water content of brain tissue, reduce the MDA and NO contents of ischemic brain tissue and the MDA content of meromorphic tissue, and raise their SOD contents, and has good effects of resisting ischemia and myocardial ischemia.
Description
Technical field
The present invention relates to field of medicaments, specifically, relate to a kind of anti-cerebral ischemia, myocardial ischemia and improve compound of memory function and its production and application.
Background technology
Existing anti-cerebral ischemia drugs has a lot, such as thrombolysis, anti-bolt, give methods of treatment such as exogenous neurotrophic factor, though obtain some successful progress aspect treatment, most pharmacological agenies still have many defectives, such as: the drug molecule amount is big, is difficult to see through hemato encephalic barrier and plays a role; Hemorrhage grade for side effect takes place in some medicine easily; Some methods of treatment operation easier is bigger, and curative effect can not be satisfactory etc.In addition, also lack the very effective medicine that resists myocardial ischemia and improve memory function at present.The present invention is intended to seek a kind of anti-cerebral ischemia and the myocardial ischemia effect is strong, use simple and the little active drug of side effect.
Summary of the invention
The purpose of this invention is to provide a kind of anti-cerebral ischemia, myocardial ischemia and improve the compound of memory function.
The present invention also aims to provide the preparation method of this compound.
The present invention also aims to provide this compound at preparation anti-cerebral ischemia and myocardial ischemia and improve application in the memory function medicine.
In order to realize purpose of the present invention, the invention provides a kind of anti-cerebral ischemia, myocardial ischemia and improve the compound of memory function, its general structure is as follows:
Wherein, R is preferably Glc or H; R ' is preferably CH
2OH or CHO.
Described compound and pharmaceutically acceptable carrier are made tablet, capsule, soft capsule, pill, granule, oral liquid, syrup or injection.
The present invention also provides described anti-cerebral ischemia, myocardial ischemia and has improved the preparation method of the compound of memory function, comprise the steps: to get composite family samara Chrysanthemum plant root, after the drying and crushing, every kilogram of medicinal material soaks 1～3 time with 2～5 liters of ethanol, methyl alcohol, 70% aqueous acetone solution or hydroecium temperature, each 3～5 days, the vat liquor underpressure distillation gets the medicinal extract of relative density 1.05～1.25 (30 ℃), with 200-300 order silica gel column chromatography, make eluent with chloroform/methanol (10: 1) mixed solvent, wash-out, promptly.
Described composite family samara Chrysanthemum plant is high samara chrysanthemum or splits the samara chrysanthemum more.
Compound of the present invention can reduce brain water content, prolonging the mouse broken end breathes the time, the MDA content of cerebral tissue MDA and NO content and cardiac muscular tissue behind the reduction ischemic, the two SOD content raises, have and improve the bad effect of Scopolamine induced mice memory acquisition, have the effect of good treating cerebral ischemia and myocardial ischemia.
Embodiment
Following examples are used to illustrate the present invention, but are not used for limiting the scope of the invention.
Embodiment 1
Get drying and pulverize after high samara chrysanthemum root 3kg, with 9L ethanol soaking at room temperature 3 times, each 5 days, the extracting solution underpressure distillation gets medicinal extract 200g, with 200-300 order silica gel column chromatography, chloroform/methanol (10: 1) is made eluent, monitors through thin-layer chromatography, getting structure is the compound 4.5g of following formula, and purity is not less than 99%.
The compound spectroscopic data is as follows:
Unformed powder, molecular formula C
21H
32O
9[α]
D 23+ 22
..62 (c 0.97, CH
3OH);
IR?v
max/cm
-1：3400，1760，1640。
1HNMR(400MHz，CH
3OH)：5.01(1H，dd，J＝11，6Hz，1-H)，4.54(1H，dd，J＝13，7Hz，3-H)，4.94(1H，br?d，J＝10Hz?5-H)，1.21(3H，d，J＝7Hz?13-H)，4.19(1H，br?d，J＝7.6Hz?14-H)，1.65(3H，br?s，15-H)。
13CNMR：(100MHz，CH
3OH)：127.6(C-1)，32.2(C-2)，83.0(C-3)，141.0(C-4)，127.4(C-5)，81.5(C-6)，54.4(C-7)，28.3(C-8)，36.0(C-9)，140.4(C-10)，42.3(C-11)，180.2(C-12)，12.3(C-13)，57.8(C-14)，10.7(C-15)，101.4(C-1’)，74.1(C-2’)，77.0(C-3’)，70.7(C-4’)，77.0(C-5’)，61.8(C-6’)。
Embodiment 2
Tablet: activeconstituents 300mg
Lactose 124mg
MCC 46mg
Magnesium Stearate 4mg
Activeconstituents, lactose, MCC are mixed, use water-wet, the mixture after wetting sieves and is dry, sieves, and adds Magnesium Stearate, mixes compressing tablet.
Embodiment 3
Capsule: activeconstituents 300mg
Lactose 87mg
Magnesium Stearate 5mg
Activeconstituents, lactose are mixed, use water-wet, the mixture after wetting sieves and is dry, sieves, and adds Magnesium Stearate, mixes, and incapsulates.
Embodiment 4
Freeze-dried powder: activeconstituents 70mg
Sodium-chlor 152mg
Activeconstituents and sodium-chlor are dissolved in an amount of water for injection, filter the solution of gained, in the peace of under aseptic condition, packing into the bottle.
Experimental example
1 material and method
1.1 animal and grouping
1.1.1 embodiment 1 described compound is to mouse broken end the breathe laboratory animal and the grouping of time effects
40 of ICR male mices, body weight 18-22g is divided into 4 groups at random, 10 every group.That is: water for injection group, embodiment 1 described compound 12.5mg/kg group, 25mg/kg group, 50mg/kg group all by the 10ml/kg abdominal injection, are injected broken end after 30 minutes, breathe the time with stopwatch numeration mouse.
1.1.2 embodiment 1 described compound is to the laboratory animal and the grouping of acute cerebral ischemia in rats influence
48 of SD male rats, body weight 180-220g is divided into 6 groups at random, 8 every group.That is: sham operated rats (equal-volume water for injection), model group (equal-volume water for injection), positive drug control group (nimodipine 1mg/kg), embodiment 1 described compound 12.5mg/kg group, 25mg/kg group, 50mg/kg organize, all by 20ml/kg, B.i.d, abdominal injection 1 day.
1.1.3 embodiment 1 described compound is to the laboratory animal and the grouping of the influence of rat heart muscle ischemic
40 of SD male rats, body weight 180-220g is divided into 5 groups, 8 every group.That is: model group (Racemic isoproterenol 30mg/kg), blank group (equal-volume water for injection), embodiment 1 described compound 12.5mg/kg group, 25mg/kg group, 50mg/kg organize, all by 20ml/kg, and B.i.d, abdominal injection 1 day.
1.1.4 embodiment 1 described compound is to the laboratory animal and the grouping of mouse memory obstacle improvement effect
60 of ICR kind mouse, male and female half and half, body weight 18-22g, every group 10, be divided into 6 groups at random, promptly blank group (giving equivalent physiological saline), pathological model group (Scopolamine 5mg/kg), positive drug control group (1% Anixidan), embodiment 1 described compound 12.5mg/kg group, 25mg/kg group, 50mg/kg organize, all by 10ml/kg, q.d., continuous 5 days abdominal injections.Choose qualified animal after the disposable training of animal via, test and misregistration number of times, SDL and EL achievement with mouse diving tower instrument.
1.2 experimental technique
1.2.1 preceding cerebral ischemic model is made and tissue treatment methods
Animal is anaesthetized (45mg/kg) with 4% Sodital, neck median incision, separate bilateral carotid, close bilateral common carotid arteries with nothing wound bulldog clamp folder poured into 24 hours in 2 hours again, 2 times/day (all abdominal injections) backs of administration are put to death animal and are taken out cerebral tissue, left side brain claims to do weight in wet base, and right brain is made 10% brain tissue homogenate and centrifuging and taking supernatant liquor-20 ℃ preservation.
1.2.2 treating myocardial ischemia damage Modelling and tissue treatment methods
Animal is anaesthetized with 10% Chloral Hydrate (300mg/kg), tracheostomy tube, separate external jugular vein to be on the waiting list blood, connecting electrocardiograph record limbs II leads, Racemic isoproterenol (isoproterenol, ISO) (30mg/kg), slowly subcutaneous injection, observe ECG change, injection ISO 10min is that visible heart rate and ST-T ripple obviously change.The control group injecting normal saline, each medication group is at injection ISO equal abdominal injection after 20 minutes, put to death animal after 2 hours and take out heart, wash down bloodstain with physiological saline, get 20-30mg cardiac muscular tissue, under 1-4 ℃ of condition, make 10% physiological saline cardiac muscular tissue homogenate, centrifugal then (3000r/min, 10min), get an amount of supernatant liquor and detect myocardial cell MDA and SOD level.
1.2.3 the measuring method of brain water content
After the left side cerebral tissue that takes out weighed with analytical balance, put into 110 ℃ of baking boxs baking 15h and weigh once more, calculate the water content of cerebral tissue then according to formula.Formula is as follows:
Tissue water content (%)=(weight in wet base-dry weight)/weight in wet base * 100%
1.2.4 cerebral tissue and the MDA of cardiac muscular tissue, SOD and NO measure
(1.2.5MDA mda) measuring method: use earlier the experimentize protein quantification of sample of Coomassie brilliant blue, take best sampling amount through experiment then, required each test tube, wortex device mixing are tested in preparation in order, 95 ℃ of water-baths 40 minutes, take out back flowing water cooling, centrifugal 10 minutes (3500-4000 rev/min), it is an amount of to get supernatant liquor, the 532nm place, the 1cm optical path, the distilled water zeroing is surveyed and is respectively managed absorbance.MDA value that last calculation formula according to MDA content in the tissue calculates each group is carried out statistical procedures.
Wherein, nmol/mgprot is sodium mole/milligram albumen.
1.2.6 total SOD (total superoxide-dismutase) measuring method: use the experimentize protein quantification of sample of Coomassie brilliant blue earlier, find out best sampling amount through experiment then, required each test tube is tested in preparation in order, the abundant mixing of wortex device is put 37 ℃ of waters bath with thermostatic control 40 minutes, then each pipe add developer again room temperature placed 10 minutes, in wavelength 550nm place, 1cm optical path cuvette, the distilled water zeroing, numerical value is respectively organized in colorimetric estimation.Calculate corresponding SOD value according to formula then, carry out statistical procedures.
(1.2.7NO nitrogen protoxide) measuring method: use earlier the experimentize protein quantification of sample of Coomassie brilliant blue, find out best sampling amount through experiment then, required each test tube is tested in preparation in order, to reagent two, mixing, 37 ℃ of waters bath with thermostatic control 60 minutes add reagent 3 and reagent 4 again, this moment, abundant mixing was 30 seconds, room temperature left standstill 10 minutes, and 3500-4000 rev/min, centrifugal 10 minutes, get supernatant 0.8ml and add developer 0.6ml, mixing once more, room temperature left standstill 10 minutes, the distilled water zeroing, 550nm, 0.5cm optical path are surveyed and are respectively managed absorbance.Calculate corresponding SOD value according to formula then, calculate according to respective formula and respectively organize the NO value and carry out statistical procedures.
Wherein, μ mol/gprot is a micromoles per gram albumen.
1.3 key instrument and reagent:
101-3 type electric heating air blast thermostatic drying chamber (production of Jintan City, Jiangsu Jiamei instrument plant), FA2004 type electronic balance (going up the flat instrument of current chart company limited produces), T6 type spectrophotometer (Beijing spectrum is analysed universal apparatus limited liability company and produced), TG16-W High Speed microCentrifuges (production of Hunan, Changsha instrument whizzer instrument company limited), the quick vortex vortex mixer of SK-1 type (production of Jintan, Jiangsu Medical Instruments factory), electric-heated thermostatic water bath (Shanghai Medical Apparatus and Instruments Factory's production), manual mouse diving tower instrument (the STT-2 type is by institute of Materia Medica,Chinese Academy of Medical Sciences production), the 5ml glass homogenizer, MDA, SOD, Coomassie brilliant blue, building up bio-engineering research with the NO test kit by Nanjing provides.
1.4 statistical procedures adopts SPSS-10 to carry out statistical procedures, measurement data all uses x ± s to represent, adopts variance analysis, compares in twos, and the neat person of variance adopts the LSD method, and the heterogeneity of variance person adopts the Duttet method, and there is significant difference P＜0.05.
2 results
2.1 embodiment 1 described compound is to the comparative analysis of forebrain ischemic tissue of brain water content influence
Each dosage group of embodiment 1 described compound and model group more all can significantly reduce the water content of cerebral tissue after the cerebral ischemia, are better than the positive drug control group with its high dose group effect of nimodipine group comparison.(seeing Table 1)
The comparison that table 1 embodiment 1 described compound influences forebrain ischemic tissue of brain water content (n=8, x ± s)
Compare with model group
*P＜0.05,
*P＜0.01; Compare with the nimodipine group
#P＜0.05
2.2 embodiment 1 described compound is to the breathe comparative analysis of time effects of mouse broken end
Each dosage group of embodiment 1 described compound and water for injection group relatively all can obviously prolong the mouse broken end and dehisce the time of breathing, and point out this medicine to have the anti-cerebral ischemia anoxia functions.(seeing Table 2)
Table 2 embodiment 1 described compound is to mouse broken end breathe comparison (n=10, the x ± s) of time effects
Compare with the water for injection group
*P＜0.05,
*P＜0.01
2.3 embodiment 1 described compound is to the comparative analysis of preceding cerebral ischemia MDA, SOD and the influence of NO value
Each dosage group of embodiment 1 described compound and model group more all can reduce the content of cerebral tissue MDA and NO after the cerebral ischemia, the content of increased SOD.Point out this medicine to have treating cerebral ischemia.With positive control medicine group relatively, this medicine is better than nimodipine to the reduction effect of NO, MDA, SOD testing index are suitable with the nimodipine effect.(seeing Table 3)
Table 3 embodiment 1 described compound is to the comparison of preceding cerebral ischemia MDA, SOD and NO value influence (n=8, x ± s)
Compare with model group
*P＜0.05,
*P＜0.01; Compare with the nimodipine group
#P＜0.05,
##P＜0.01
2.4 implementing 1 described compound compares the analysis of acute myocardial ischemia MDA, the influence of SOD value
Each dosage group of embodiment 1 described compound and model group more all can reduce the content of cerebral tissue MDA and NO behind the treating myocardial ischemia damage, the content of increased SOD.Point out this medicine to have the anoxia functions of resisting myocardial ischemia.(seeing Table 4)
The comparison that table 4 embodiment 1 described compound influences acute myocardial ischemia MDA, SOD value (n=8, x ± s)
Compare with model group
*P＜0.05,
*P＜0.01
Memory obtains dysgenic comparative analysis 2.5 embodiment 1 described compound is to the Scopolamine induced mice
The paramnesia number of times of each dosage group of embodiment 1 described compound and model group comparison mouse obviously reduces, and the SDL time obviously increases, and the EL time significantly reduces, and points out this medicine to have and improves the bad effect of Scopolamine induced mice memory acquisition.Experiment also shows: this medicine is basic suitable with the effect of positive control medicine.(seeing Table 5)
Table 5 embodiment 1 described compound obtains bad influence (n=10, x ± s) to Scopolamine induced mice memory
Compare with the Scopolamine group
*P＜0.05,
*P＜0.01; Compare with 1% Anixidan group
#P＜0.05,
##P＜0.01
Above-mentioned experiment shows that embodiment 1 described compound can be applied to following field:
1. be used for the treatment of cerebral ischemia and thrombotic diseases due to cerebral vasospasm disease and other reason.
2. be used for the treatment of the myocardial ischemia disease due to a variety of causes.
3. be used to prevent and treat the memory impairment due to senile dementia and the cerebrovascular disease.
This monomeric compound of embodiment 1 described compound can be made oral dosage form patients such as tablet, capsule or oral liquid for above treatment of diseases and use, medicine can oral or intravenously administrable.
Claims (4)
1, a kind of anti-cerebral ischemia, myocardial ischemia and improve the compound of memory function, its structural formula is as follows:
Wherein, R is Glc; R ' is CH
2OH.
2, anti-cerebral ischemia as claimed in claim 1, myocardial ischemia and improve the preparation method of the compound of memory function, comprise the steps: to get composite family samara Chrysanthemum plant root, after the drying and crushing, every kilogram of medicinal material is with 2～5 liters of ethanol, methyl alcohol or 70% aqueous acetone solution soaking at room temperature 1～3 time, each 3～5 days, the medicinal extract of relative density 1.05～1.25 when the vat liquor underpressure distillation gets 30 ℃, with 200-300 order silica gel column chromatography, use chloroform: methyl alcohol is that 10: 1 mixed solvent is made eluent, wash-out.
3, preparation method as claimed in claim 2 is characterized in that described composite family samara Chrysanthemum plant is high samara chrysanthemum or splits the samara chrysanthemum more.
4, compound as claimed in claim 1 is at preparation anti-cerebral ischemia and myocardial ischemia and improve application in the memory function medicine.
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| CN102988351A (en) * | 2012-11-19 | 2013-03-27 | 何晓涛 | Application of Aphanamixoid A for preparing medicine for treating myocardial ischemia |
| CN104095840B (en) * | 2014-06-23 | 2016-04-27 | 西安交通大学 | The application of euparin in preparation treatment ischemic cardio cerebrovascular diseases medicine |
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| CN1194980A (en) * | 1998-04-13 | 1998-10-07 | 中国科学院广州化学研究所 | 1-isopropyl-4-methyl bicyclic [2,2,2] octane-2,3-diacid anhydride and producing process thereof |
| CN1215055A (en) * | 1998-09-08 | 1999-04-28 | 中国科学院昆明植物研究所 | Sesquilterpenic internal ester compound for anti-ulcer of alimentary tract |
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Application publication date: 20070328 Assignee: Xinxiang Zuojinming Pharmaceutical Group Assignor: Yan Fulin|Zhan Heqin Contract record no.: 2013410000048 Denomination of invention: Compound with anti cerebralischemia, myo cardialischemia and memory-improving functions, and its preparing method and use Granted publication date: 20081015 License type: Exclusive License Record date: 20130617 |
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