CN106543133A - Wild anistree new isopentene group replaces C6‑C3Class compound and preparation method thereof, application and its pharmaceutical composition - Google Patents
Wild anistree new isopentene group replaces C6‑C3Class compound and preparation method thereof, application and its pharmaceutical composition Download PDFInfo
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- CN106543133A CN106543133A CN201611024317.4A CN201611024317A CN106543133A CN 106543133 A CN106543133 A CN 106543133A CN 201611024317 A CN201611024317 A CN 201611024317A CN 106543133 A CN106543133 A CN 106543133A
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- C07—ORGANIC CHEMISTRY
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- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
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Abstract
The invention discloses a kind of new isopentene group extracted from wild anise replaces C6‑C3Class compound, and preparation method thereof, and replace C containing new isopentene group6‑C3The pharmaceutical composition of class compound, and the application in nerve protection medicine:Particularly apoplexy.Compound of the present invention has structure described in Formulas I, and pharmacological evaluation shows that the compounds of this invention embodies neuroprotective activity, i.e., in H2O2Damage in primary neuronal models and glutamate induction primary neuron toxic model and be respectively provided with good neuroprotective activity.Formula I.
Description
Technical field
The present invention relates to compound synthesis field, more particularly to wild anistree new isopentene group replacement C6-C3Class compound and its
Preparation method, application and pharmaceutical composition.
Background technology
It is wild anistree（Iliicium simonsii Maxim）For Illicium（Illicium L.）Plant, originates in China Guizhou
The northwestward to the west and south, Sichuan and Yunnan and India, Burma.Leaf, fruit medicine, acrid in the mouth, property heat；Have town to vomit, promoting the circulation of QI to relieve pain,
Granulation promoting synthetism, the effect of delousing parasite killing, can control cold syndrome of the stomach feel sick, bladder hernia, front distending pain, scabies the effects such as.
Apoplexy（cerebral apoplexy）It is the primary cause of disease for causing global human to be disabled, the world's second largest cause of the death.
In some countries and cities, apoplexy even alreadys exceed cardiovascular diseasess, becomes first cause of the death.Developed according to Chinese biological technology
Center sampling investigation data display, the annual morbidity average out to 2,00/,100,000 of Chinese Cerebrovascular Disease, prevalence be 400 ~
700/100000, the annual new carbuncle in the occipital region angiopathy case 2,500,000 in the whole nation, mortality rate is 1,30/,100,000, is China human mortality total dead second
Position reason, alreadys exceed cardiovascular disease and tumor in Beijing, becomes first cause of death.It is national to be used for every year treating brain blood
The expense of pipe disease adds indirect economic loss more than 20,000,000,000 yuan up to more than 10,000,000,000 yuan.As can be seen here, cerebrovascular has become
Have a strong impact on the important public hygiene problem of China's people's livelihood.The theme that world's apoplexy day in 2010 is issued is " 1/6th ", i.e.,
The whole world per 6 people in have 1 people suffer from apoplexy in life；Just there is 1 people to die from apoplexy per 6s；And just have 1 people per 6min
Forever disable because of apoplexy.Apoplexy is one of world today's major disease.It is anti-brain soldier from medium-height grass the effective elements of the medicine
The study hotspot of middle new drug.
The content of the invention
Wild anise ethanol extraction has neuroprotective, and from effective site, isolated 1 new isopentene group takes
For C6-C3Class compound, pharmacodynamic evaluation show which has the effect of good neuroprotective.
An object of the present invention is to provide a kind of wild anistree new isopentene group to replace C6-C3Class compound.
The second object of the present invention there are provided a kind of wild anistree new isopentene group and replace C6-C3The preparation of class compound
Method.
The third object of the present invention there are provided a kind of wild anistree new isopentene group and replace C6-C3It is prepared by class compound
Cerebrovascular disease medicament is treated in prevention（Nerve protection medicine）In application.
The fourth object of the present invention there are provided a kind of pharmaceutical composition, and which contains a new isopentene group and replaces C6-
C3Class compound.
The present invention is achieved by the following technical solutions：Wild anistree new isopentene group replaces C6-C3Class compound, has
Structure shown in formula I
Formula I
The preparation method of compound as shown in formula I, wherein, often prepare this compound 5mg and comprise the following steps：
A. open country anise 10.50 kg of fruit being dried, crushes, is soaked after 2 h with 95% EtOH, 80 L, heating and refluxing extraction 3 times,
2 hours every time, extracting solution concentrating under reduced pressure obtained 261.2 g extractum；
B. extractum is dissolved in methanol, is adsorbed in 500 g kieselguhr, be dried, load apparatus,Soxhlet'ses, successively with petroleum ether,
Ethyl acetate and Soxhlet extraction with methanol are extracted；
C. concentrating under reduced pressure obtains 44.2 g of petroleum ether part, 75.0 g of ethyl acetate extract and methanol position to each extracting solution respectively
133.6 g；
D. to ethyl acetate extract methylene chloride-methanol（Dichloromethane:Methanol=50:1；25:1；10:1；5:1；2:1；1:
1；0:100）It is gradient elution separation to obtain stream part Fr1-Fr7；
E. to Fr4 (8g) by middle compression leg chromatography（The methanol elution gradient of 10-90 % 10 hours）It is divided into 50 stream parts
（500 ml are 1 part）, a new isopentene group replacement C is obtained from Fr. 22-23 by preparing liquid phase6-C3Chemical combination shown in class formula I
Thing（5mg）.
Application of the type I compound in prevention or treatment cerebrovascular disease medicament is prepared；The cerebrovascular disease medicament is
Nerve protection medicine；The cerebrovascular disease is apoplexy, dementia, neuroinflamation, heavy metal poisoning, never poison poisoning；Institute
Apoplexy is stated for cerebral infarction or hemorrhagic apoplexy.
A kind of pharmaceutical composition, wherein, containing acceptable carrier on the compound and pharmacodynamicss shown in formula I.
Thinking of the invention, replaces C to wild anistree new isopentene group6-C3Shown in class formula I, compound has carried out nerve
The related pharmacological evaluation of protection.Oxidative stress is the major reason for causing Neuron Apoptosis to be lost, and is the spy of cerebral infarction
Levy.The reason for causing oxidative stress has many kinds, such as cerebral ischemia, and neuroinflamation, excitatory transmitter discharge reuptake mechanism impediment,
Heavy metal exposes, neurotoxicity agent exposure etc., shows as intracellular free radicals increase, causes lipid peroxidation, mitochondrial function
Obstacle activates apoptosis pathway etc. then.Glutamic acid, H2O2Although causing the mechanism that Neuron Apoptosis are lost to differ, all it is in recent years
Carry out the inducing agent of the neuronal damage model that many Chinese scholars are advocated.Research thinks, intracerebral excitatory transmitter glutamic acid mistake
Amount generally causes nmda receptor excessive activation on neuron membrane, so as to cause neuron oxidative stress to occur and loses, and H2O2It is
A kind of peroxide, based on its inducing nerve cell oxidativestress damage model, discloses clinical effectively medicine effect
Mechanism, can be used as a kind of reliable pharmacology cell model of in-vitro screening anti-oxidation medicine, its mechanism, pathophysiological change
With the performance of patients with cerebral apoplexy intracerebral with similarity.Using glutamic acid, H2O2Make neuronal damage Model Condition and require low, skill
Art is easy to grasp, highly reliable, reproducible, therefore in our current research, H2O2Damage primary neuronal models, glutamate induction
2 external models of primary neuron Apoptosis Model are used as evaluation meanses.
Inventor has found that new isopentene group replaces C6-C3The glutamic acid in vitro of compound shown in class formula I, H2O2What is induced is big
Excellent neuroprotective is shown in the dead test of Mus Cortical Neurons.
Positive control medicine is Edaravone（edaravone）, Edaravone is with free radical scavenging as Main Function machine
The nerve protection medicine of system, effectively can suppress because brain cell caused by cerebral ischemia, vascular endothelial cell, neurocyte oxidation should
Swash and damage.
To H2O2Induction rat cerebral cortex Neuron Apoptosis protective effect in vitro study in, by compound shown in formula I with
Edaravone（300μM）Diluted with neuronal culture, and after rat cerebral cortex neuron temperature incubates 24 hours, mtt assay is determined
Cell survival rate, while carrying out Normal group and positive controls test.Test result indicate that, Normal group adds H2O2
Absorbance at 570 nm afterwards（OD570）Substantially reduce, compound OD shown in positive controls and formula I570Rebound significantly, and according to reaching
La Feng（edaravone）Cell survival rate quite, the cell survival rate of noval chemical compound group is suitable with Edaravone group.
Glutamic acid is induced in the protective effect in vitro study of rat cerebral cortex Neuron Apoptosis, by chemical combination shown in formula I
Thing and glutamic acid（20 mM）Diluted with complete medium, and after rat cerebral cortex neuron temperature incubates 24 hours, mtt assay is determined
Cell survival rate, while carrying out Normal group and positive controls test.Test result indicate that, Normal group adds paddy ammonia
Absorbance at 570 nm after acid（OD570）Substantially reduce, compound OD shown in positive controls and formula I570Rebound significantly, with according to
Da Lafeng（edaravone）Cell survival rate quite, the cell survival rate of noval chemical compound group is suitable with Edaravone group.
Therefore beneficial effects of the present invention：Compound shown in formula I is to can be used to prepare prevention or treat cerebrovascular disease
Medicine（Nerve protection medicine）.Preferred cerebrovascular disease is selected from apoplexy, dementia, neuroinflamation, heavy metal poisoning, Nervous toxicity
Agent is poisoned.Preferred apoplexy is in ischemic cerebral apoplexy and hemorrhagic apoplexy.
Description of the drawings
The extraction flow chart of the wild anise fruits of Fig. 1.
Specific embodiment
The following examples and pharmacologically active experiment further illustrate the present invention, but are not meant to any of the present invention
Limit.
Embodiment 1：Extraction separating experiment combines accompanying drawing 1 and illustrates：Dry open country anise 10.50 kg of fruit, crushes, uses 95%
After 80 L of EtOH soak 2 h, heating and refluxing extraction 3 times, 2 hours every time, extracting solution concentrating under reduced pressure obtained 261.2 g extractum.
Extractum is dissolved in methanol, 500 g kieselguhr are adsorbed in, is dried, load apparatus,Soxhlet'ses, successively with petroleum ether, acetic acid second
Ester and Soxhlet extraction with methanol are extracted.Concentrating under reduced pressure obtains 44.2 g of petroleum ether part, ethyl acetate extract 75.0 to each extracting solution respectively
133.6 g of g and methanol position.To ethyl acetate extract methylene chloride-methanol（Dichloromethane:Methanol=50:1；25:1；10:
1；5:1；2:1；1:1；0:100）It is gradient elution separation to obtain stream part Fr1-Fr7.To Fr4 (8g) by middle compression leg chromatography（10
The methanol elution gradient of -90 % 10 hours）It is divided into 50 stream parts（500 ml are 1 part）, by preparing liquid phase from Fr. 22-23
Obtain a new isopentene group and replace C6-C3Compound shown in class formula I（5mg）.
Isopentene group replaces C6-C3Shown in class formula I, the physics and chemistry of compound, spectral data are as follows:
White powder, ESI-MS m/z283 [M+H]+。1H-NMR (Acetone-d 6 , 500 MHz) δ :5.70 (1H,
m, H-8), 5.49 (1H, s, H-6), 5.04 (2H, m, H-9), 3.78 (3H, s, OCH3-5), 3.37
(1H, m, H-11), 2.59 (1H, dd, J = 13.5 Hz, J = 6.1 Hz, H-10α ), 2.02 (1H,
overlap, H-10β ), 2.10 (1H, d, J = 12.5 Hz, H-3α ), 1.57 (1H, d, J = 12.5 Hz,
H-3β ), 1.45 (2H, d, J = 8.4 Hz, H-7), 1.11 (3H, s, H-13), 1.08 (3H, s, H-
14)。13C-NMR(Acetone-d 6 , 125 MHz）δ : 200.4(C-1), 170.6 (C-5), 135.1 (C-8),
118.4 (C-9), 104.5 (C-6), 94.8 (C-4), 78.6 (C-11), 71.4 (C-12), 56.8 (OCH3-
5), 45.7(C-2), 42.4 (C-3), 42.3 (C-10), 34.9 (C-7), 26.5(C-13), 25.8 (C-14)。
Pharmacological evaluation
Test material 1, by reagent：Monomeric compound of the present invention.2nd, positive control drug：Edaravone, is examined by Chinese food medicine
Academy's offer is provided.HPLC detects purity>98%.3rd, cell：Birth same day rat cerebral cortex neuron.4th, culture medium：
DMEM, FBS, the production of Gibco companies of the U.S.；ES, the production of Hyclone companies of the U.S..5、H2O2By with glutamic acid by Beijing Chemical Plant
There is provided.
Embodiment 2：A kind of pharmaceutical composition, wherein, containing acceptable load on the compound and pharmacodynamicss shown in formula I
Body.Weight content of the compound shown in formula I in its pharmaceutical composition is 0.1%-95%.
Compound shown in formula I or the pharmaceutical composition containing it can be administered in a unit, and route of administration can be intestinal
Road or non-bowel, such as oral, nasal cavity, oral mucosa, skin, peritoneum, rectum etc..
Form of administration can be liquid dosage form, solid dosage formss or semisolid dosage form.Liquid dosage form can be that solution (includes
True solution and colloid solution), Emulsion (include o/w types, w/o types and emulsion), suspensoid, injection (include aqueous injection, powder pin
Agent and transfusion), eye drop, nasal drop, lotion and liniment etc.；Solid dosage formss can be that tablet (includes ordinary tablet, enteric coatel tablets, contains
Piece, dispersible tablet, chewable tablet, effervescent tablet, oral cavity disintegration tablet), capsule (include hard capsule, soft capsule, enteric coated capsule), granule
Agent, powder, micropill, drop pill, suppository, membrane, paster, gas (powder) mist agent, spray etc.；Semisolid dosage form can be ointment,
Gel, paste etc..
Compound shown in formula I can be made ordinary preparation, can also be slow releasing preparation, controlled release preparation, targeting preparation and each
Plant particulate delivery system.
In order to compound shown in formula I is made tablet, various excipient well known in the art can be widely used, including it is dilute
Release agent, adhesive, wetting agent, disintegrating agent, lubricant, fluidizer.Diluent can be starch, dextrin, sucrose, glucose, breast
Sugar, Mannitol, Sorbitol, xylitol, Microcrystalline Cellulose, calcium sulfate, calcium hydrogen phosphate, Calcium Carbonate etc.；Wetting agent can be water, second
Alcohol, isopropanol etc.；Binding agent can be starch slurry, dextrin, syrup, Mel, glucose solution, Microcrystalline Cellulose, arabic gum
Slurry, gelatine size, sodium carboxymethyl cellulose, methylcellulose, hydroxypropyl methyl cellulose, ethyl cellulose, acrylic resin, card
Ripple nurse, polyvinylpyrrolidone, Polyethylene Glycol etc.；Disintegrating agent can be dried starch, Microcrystalline Cellulose, low substituted hydroxy-propyl fiber
Element, crospolyvinylpyrrolidone, Croscarmellose Sodium, carboxymethyl starch sodium, sodium bicarbonate and citric acid, polyoxy second
Alkene sorbitan fatty acid ester, dodecyl sodium sulfate etc.；Lubricant and fluidizer can be Pulvis Talci, silicon dioxide, Hard Fat
Hydrochlorate, tartaric acid, liquid paraffin, Polyethylene Glycol etc..
Tablet further can also be made coated tablet, such as sugar coated tablet, thin membrane coated tablet, ECT, or it is double
Synusia and multilayer tablet.
In order to administration unit is made capsule, compound shown in effective ingredient formula I and diluent, fluidizer can be mixed
Close, during mixture is placed directly within hard capsule or soft capsule.Also can by compound shown in effective ingredient formula I first with diluent, glutinous
Mixture, disintegrating agent make granule or micropill, then are placed in hard capsule or soft capsule.For preparing compound tablet shown in formula I
Each diluent, adhesive, wetting agent, disintegrating agent, fluidizer kind can also be used for the capsule for preparing compound shown in formula I.
It is that compound shown in formula I is made into injection, water, ethanol, isopropanol, Propylene Glycol or their mixture can be used
Make solvent and add appropriate solubilizing agent commonly used in the art, cosolvent, pH adjustment agent, osmotic pressure regulator.Solubilizing agent or hydrotropy
Agent can be poloxamer, lecithin, hydroxypropyl-β- cyclodextrin etc.；PH adjust agent can be phosphate, acetate, hydrochloric acid,
Sodium hydroxide etc.；Osmotic pressure regulator can be Sodium Chloride, Mannitol, glucose, phosphate, acetate etc..Lyophilizing is prepared such as
Injectable powder, can also add Mannitol, glucose etc. as proppant.
Additionally, if desired, coloring agent, preservative, spice, correctivess or other additions can also be added in pharmaceutical preparation
Agent.
To reach medication purpose, strengthen therapeutic effect, the medicine or pharmaceutical composition of the present invention known can be given with any
Prescription method is administered.
The dosage of compound medicine compositionss shown in formula I is according to the property that will prevent or treat disease and serious journey
The individual instances of degree, patient or animal, route of administration and dosage form etc. can have change on a large scale.In general, formula I shownization
The daily Suitable dosage ranges of compound are 0.001-150mg/Kg body weight, preferably 0.1-100mg/Kg body weight, more preferably
For 1-60mg/Kg body weight, most preferably 2-30mg/Kg body weight.Above-mentioned dosage with a dosage unit or can be divided into several doses
Amount unit administration, this depends on the clinical experience of doctor and including the dosage regimen with other treatment meanss.
The compound or compositionss of the present invention individually can be taken, or merge use with other treatment medicine or symptomatic drugs.
When the compound of the present invention has synergism with other medicines, its dosage should be adjusted according to practical situation.
Embodiment 3：Impact of the compound shown in formula I to rat cerebral cortex neuronal survival state and in H2O2Induction
Neuronal apoptotic models in protective effect.
In the influence research of compounds on nerve unit existing state, by original cuiture Cortical Neurons of Rat (DIV-9) point
For matched group and administration group (10 μM), n=6；In compound to H2O2In the protective effect research of induction neuronal apoptotic models,
Original cuiture Cortical Neurons of Rat (DIV-7) is divided into into matched group, H2O2(300 μM) modeling group, H2O2(300 μM)+according to reaching
La Feng (100 μM) administration group, H2O2(300 μM)+compound (10 μM) administration group, n=6.After administration, cell is placed in cell and incubates
Continue culture 24 hours in case, mtt assay (570nm) determines cell survival rate.With matched group absorbance as standard, each group is calculated
The ratio of absorbance and matched group.
Embodiment 4：Protective effect of the compound in the Cortical Neurons of Rat Apoptosis Model that glutamic acid induces
Original cuiture Cortical Neurons of Rat (DIV-9) is divided into into matched group, glutamic acid (20 mM) modeling group, glutamic acid (20
MM)+Edaravone (100 μM) administration group, glutamic acid (20 mM)+compound (10 μM) administration group, n=6 are incubated in cell
After continuing culture in case 24 hours, mtt assay determines cell survival rate.With matched group absorbance as standard, each group absorbance is calculated
With the ratio of matched group.
Table noval chemical compound is in H2O2With the neuroprotective in the primary neuronal cell damage model of glutamate induction
Note：* p<0.05 vs mod, * * p<0.01 vs mod, * * * p<0.001vs mod, ## P ＜ 0.01vs
control.
Test result indicate that：Preliminary cell model screening, chemical combination shown in formula I are entered to compound shown in identified formula I
Thing embodies neuroprotective activity, i.e., in H2O2Damage primary neuronal models and glutamate induction primary neuron toxic model
In be respectively provided with good neuroprotective activity.
The explanation of above example is only intended to help and understands the method for the present invention and its core concept.It should be pointed out that right
For those skilled in the art, under the premise without departing from the principles of the invention, the present invention can also be carried out
Some improvement and modification, these improve and modification is also fallen in the protection domain of the claims in the present invention.
Claims (7)
1. wild anistree new isopentene group replaces C6-C3Class compound, it is characterised in that with structure shown in formula I
Formula I.
2. as shown in claim 1 compound preparation method, it is characterised in that often preparing this compound 5mg includes following step
Suddenly：
A. open country anise 10.50 kg of fruit being dried, crushes, is soaked after 2 h with 95% EtOH, 80 L, heating and refluxing extraction 3 times,
2 hours every time, extracting solution concentrating under reduced pressure obtained 261.2 g extractum；
B. extractum is dissolved in methanol, is adsorbed in 500 g kieselguhr, be dried, load apparatus,Soxhlet'ses, successively with petroleum ether,
Ethyl acetate and Soxhlet extraction with methanol are extracted；
C. concentrating under reduced pressure obtains 44.2 g of petroleum ether part, 75.0 g of ethyl acetate extract and methanol position to each extracting solution respectively
133.6 g；
D. to ethyl acetate extract methylene chloride-methanol（Dichloromethane:Methanol=50:1；25:1；10:1；5:1；2:1；1:
1；0:100）It is gradient elution separation to obtain stream part Fr1-Fr7；
E. to Fr4 (8g) by middle compression leg chromatography（The methanol elution gradient of 10-90 % 10 hours）It is divided into 50 stream parts
（500 ml are 1 part）, a new isopentene group replacement C is obtained from Fr. 22-23 by preparing liquid phase6-C3Chemical combination shown in class formula I
Thing（5mg）.
3. application of the compound as claimed in claim 1 in prevention or treatment cerebrovascular disease medicament is prepared.
4. the application according to claim 3, it is characterised in that the cerebrovascular disease medicament is nerve protection medicine.
5. the application according to claim 3, it is characterised in that the cerebrovascular disease is apoplexy, dementia, neuritiss
Disease, heavy metal poisoning, never poison poisoning.
6. application according to claim 5, it is characterised in that the apoplexy is cerebral infarction or hemorrhagic brain soldier
In.
7. a kind of pharmaceutical composition, it is characterised in that be subjected to containing on the compound and pharmacodynamicss shown in claim 1
Carrier.
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| CN107445840A (en) * | 2017-08-18 | 2017-12-08 | 华北理工大学 | Wild anistree new Phenylpropanoid Glycosides and preparation method thereof, application and pharmaceutical composition |
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