CN107445840A - Wild anistree new Phenylpropanoid Glycosides and preparation method thereof, application and pharmaceutical composition - Google Patents
Wild anistree new Phenylpropanoid Glycosides and preparation method thereof, application and pharmaceutical composition Download PDFInfo
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- CN107445840A CN107445840A CN201710714049.7A CN201710714049A CN107445840A CN 107445840 A CN107445840 A CN 107445840A CN 201710714049 A CN201710714049 A CN 201710714049A CN 107445840 A CN107445840 A CN 107445840A
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- methanol
- compound
- phenylpropanoid glycosides
- extract
- pharmaceutical composition
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
Abstract
The invention discloses a kind of new Phenylpropanoid Glycosides extracted from wild anistree, and preparation method thereof, and the pharmaceutical composition containing new Phenylpropanoid Glycosides, and the application in nerve protection medicine:Particularly cerebral apoplexy.Pharmacological evaluation shows that the compounds of this invention embodies neuroprotective activity, i.e., in H2O2Good neuroprotective activity is respectively provided with damage primary neuronal models and glutamate induction primary neuron toxic model.1。
Description
Technical field
The present invention relates to compound extraction separation field, more particularly to new Phenylpropanoid Glycosides and preparation method thereof, application and medicine
Composition.
Background technology
It is wild anistree（Iliicium simonsii Maxim）For Illicium（Illicium L.）Plant, originate in China Guizhou
The northwestward to the west and south, Sichuan and Yunnan and India, Burma.Leaf, fruit medicine, acrid flavour, property heat；There is town to vomit, promoting qi circulation and relieving pain,
Myogenic synthetism, the effect of delousing desinsection, can control stomach cold feel sick, bladder hernia, front distending pain, scabies and other effects.
Cerebral 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, palsy even alreadys exceed cardiovascular disease, turns into first cause of the death.Developed according to Chinese biological technology
The data of center sampling investigation shows, the annual morbidity average out to 2,00/,100,000 of Chinese Cerebrovascular Disease, illness rate for 400 ~
700/100000, the annual new hair cerebrovascular disease case 2,500,000 in the whole nation, the death rate is 1,30/,100,000, is China human mortality total dead second
Position reason, alreadys exceed angiocardiopathy and tumour in Beijing, turns into first cause of death.It is national to be used to treat brain blood every year
The expense of pipe disease is up to more than 10,000,000,000 yuan, plus indirect economic loss more than 20,000,000,000 yuan.As can be seen here, cerebrovascular disease has become
Have a strong impact on the important public hygiene problem of China's people's livelihood.World's palsy day in 2010 issue theme be " 1 "/6th, i.e.,
There is 1 people to suffer from palsy in life in every 6 people in the whole world；Just there is 1 people to die from palsy per 6s；And just there is 1 people per 6min
Forever disable because of palsy.Cerebral 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 anistree ethanol extract has neuroprotection, isolated 1 new Phenylpropanoid Glycosides, drug effect from active component
Learn evaluation and show that it has the function that good neuroprotection.
Present invention solves the technical problem that it is the provision of a new Phenylpropanoid Glycosides；
Another technical problem that the present invention solves is the provision of the preparation method of a new Phenylpropanoid Glycosides；
The another technical problem that the present invention solves is to provide a kind of pharmaceutical composition, and it contains a new Phenylpropanoid Glycosides；
Present invention solves the technical problem that being to provide a kind of pharmaceutical composition, it contains a new Phenylpropanoid Glycosides as neuroprotection
The application of medicine.
Specifically, compound of the present invention
1
The preparation method of one of the present invention new Phenylpropanoid Glycosides 1, is comprised the following steps that：
A. the wild anistree kg of fruit 10.50 dried, crush, after soaking 2 h with the L of 95% EtOH 80, heating and refluxing extraction 3 times,
2 hours every time, extract solution was concentrated under reduced pressure, and obtained 261.2 g medicinal extract；
B. medicinal extract is dissolved in methanol, is adsorbed in 500 g diatomite, dry, load apparatus,Soxhlet's, successively with petroleum ether,
Ethyl acetate and Soxhlet extraction with methanol extraction；
C. each extract solution is concentrated under reduced pressure to obtain petroleum ether part 44.2 g, the g of ethyl acetate extract 75.0 and methanol position 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, the isolated fraction Fr1-Fr6 of gradient elution；
E. to 6 g, Fr3 is by middle compression leg chromatography, 10-60 % methanol elution gradient, is divided into 40 fractions, and every 500
Ml is 1 part, and new [(5 mg, MeCN-a H of Phenylpropanoid Glycosides 1 is obtained from Fr. 3-1 by preparing liquid phase2O (20:80), t R= 35
min)]。
Application of the described compound in prevention or treatment cerebrovascular disease medicament is prepared.The cerebrovascular disease medicament
For nerve protection medicine.The cranial vascular disease is cerebral apoplexy, dementia, neuroinflamation, heavy metal poisoning, never poison poisoning.
The cerebral apoplexy is cerebral arterial thrombosis or hemorrhagic apoplexy.
Contain acceptable carrier in the compound of neolignan 1 and pharmacodynamics.
According to the thinking of the present invention, the related pharmacological evaluation of neuroprotection has been carried out to wild anistree new Phenylpropanoid Glycosides.Oxidation should
It is the major reason for causing Neuron Apoptosis to be lost to swash, and is the feature of cerebral arterial thrombosis.The reason for causing oxidative stress has very
It is a variety of, such as cerebral ischemia, neuroinflamation, excitatory transmitter release reuptake mechanism impediment, heavy metal exposure, neurotoxicity agent exposure
Deng, show as intracellular free radicals increase, cause lipid peroxidation, mitochondria dysfunction then activates apoptosis pathway etc..Paddy
Propylhomoserin, H2O2All it is the nerve that many domestic and foreign scholars are advocated in recent years although the mechanism for triggering Neuron Apoptosis to lose differs
The inducing agent of first damage model.Research thinks, intracerebral excitatory transmitter glutamic acid excessively generally cause on neuron membrane NMDA by
Body excessive activation, so as to cause neuron that oxidative stress occurs and lose, and H2O2It is a kind of peroxide, with its inducing neural
Based on cellular oxidation stress damage model, clinical effective mechanism of drug action is disclosed, in-vitro screening can be used as anti-oxidant
A kind of reliable pharmacology cell model of medicine, its mechanism, pathophysiological change have with the performance of patients with cerebral apoplexy intracerebral
Similitude.Using glutamic acid, H2O2Make neure damage Model Condition and require low, technology is easy to grasp, highly reliable, repeats
Property is good, therefore in our current research, H2O2It is external to damage primary neuronal models, glutamate induction primary neuron Apoptosis Model 2
Model is as evaluation meanses.
Inventor has found new Phenylpropanoid Glycosides glutamic acid in vitro, H2O2The experiment of the rat cerebral cortex neuronal death of induction
In show excellent neuroprotection.
Positive control medicine is Edaravone（edaravone）, Edaravone is using radicals scavenging as main function machine
The nerve protection medicine of system, the oxidation that can effectively suppress the brain cell caused by cerebral ischemia, vascular endothelial cell, nerve cell are answered
Swash damage.
To H2O2Induce rat cerebral cortex Neuron Apoptosis protective effect in vitro study in, by the compounds of this invention with
Edaravone（300μM）Diluted with neuronal culture, and after rat cerebral cortex neuron temperature incubates 24 hours, mtt assay measure
Cell survival rate, while carry out Normal group and positive controls experiment.Test result indicates that Normal group adds H2O2
Absorbance at 570 nm afterwards（OD570）It is obvious to reduce, positive controls and the compounds of this invention OD570Rebound significantly, with according to up to
La Feng（edaravone）Cell survival rate it is suitable, the cell survival rate of noval chemical compound group is suitable with Edaravone group.
In the protective effect in vitro study for inducing glutamic acid rat cerebral cortex Neuron Apoptosis, by the compounds of this invention
With glutamic acid（20 mM）Diluted with complete medium, and after rat cerebral cortex neuron temperature incubates 24 hours, mtt assay measure is thin
Born of the same parents' survival rate, while carry out Normal group and positive controls experiment.Test result indicates that Normal group adds glutamic acid
Absorbance at 570 nm afterwards（OD570）It is obvious to reduce, positive controls and the compounds of this invention OD570Rebound significantly, with according to up to
La Feng（edaravone）Cell survival rate it is suitable, the cell survival rate of noval chemical compound group is suitable with Edaravone group.
Brief description of the drawings
The extraction flow chart of the wild anistree fruits of Fig. 1.
Embodiment
The following examples and pharmacological activity experiment further illustrate the present invention, but are not meant to any of the present invention
Limitation.
Extract separating experiment（See accompanying drawing 1）
The dry wild anistree kg of fruit 10.50, crush, after soaking 2 h with the L of 95% EtOH 80, heating and refluxing extraction 3 times, often
Secondary 2 hours, extract solution was concentrated under reduced pressure, and obtained 261.2 g medicinal extract.Medicinal extract is dissolved in methanol, is adsorbed in 500 g diatomite,
Dry, load apparatus,Soxhlet's, extracted successively with petroleum ether, ethyl acetate and Soxhlet extraction with methanol.Each extract solution depressurizes respectively
It is concentrated to give petroleum ether part 44.2 g, the g of ethyl acetate extract 75.0 and the g of methanol position 133.6.Wherein ethyl acetate extraction unit
Multiple column chromatography is passed through in position（Positive reverse phase silica gel, gel）, finally purified with HPLC, a new Phenylpropanoid Glycosides 1 obtained, to ethyl acetate
Position methylene chloride-methanol（Dichloromethane:Methanol=50:1；25:1；10:1；5:1；2:1；1:1；0:100）Gradient elution
Isolated fraction Fr1-Fr6.Middle compression leg chromatography is passed through to Fr3 (6 g)（10-60 % methanol elution gradient）It is divided into 40
Individual fraction（500 ml are 1 part）, new [(5 mg, MeCN-a H of Phenylpropanoid Glycosides 1 is obtained from Fr. 3-1 by preparing liquid phase2O
(20:80), t R= 35 min)]。
Physics and chemistry, the spectral data of new Phenylpropanoid Glycosides are as follows:
For colorless oil; [α]20 D+ 17.6 (c 0.50 MeOH); HRESIMS m/z255.08645 [M + H]+
(calcd for C12H15O6, 255.08687)。1H-NMR (CD3OD, 600 MHz) and13C-NMR (CD3OD, 150MHz）
It see the table below
Table 11H and 13C NMR data of compound 1 in CD3OD
Pharmacological evaluation
Test material 1, by reagent：Monomeric compound of the present invention.2nd, positive control drug：Edaravone, examined by Chinese food medicine
Research institute'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 1：Influence of the compounds of this invention to rat cerebral cortex neuronal survival state and in H2O2Induce
Protective effect in neuronal apoptotic models.
In the influence research of compounds on nerve member existing state, by original cuiture Cortical Neurons of Rat (DIV-9) point
For control group and administration group (10 μM), n=6；In compound to H2O2In the protective effect research for inducing neuronal apoptotic models,
Original cuiture Cortical Neurons of Rat (DIV-7) is divided into control group, H2O2 (300 μM) modeling group, H2O2 (300 μM)+according to up to
La Feng (100 μM) administration group, H2O2 (300 μM)+compound (10 μM) administration group, n=6.After administration, cell is placed in cell and incubated
Continue culture 24 hours, mtt assay (570nm) measure cell survival rate in case.Using control group absorbance as standard, each group is calculated
The ratio of absorbance and control group.
Embodiment 2：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 control 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, in thin
After continuing culture in born of the same parents' incubator 24 hours, mtt assay measure cell survival rate.Using control group absorbance as standard, calculate each group and inhale
The ratio of luminosity and control group.
Influence of the compound of table 2 to Cortical Neurons of Rat existing state
The noval chemical compound of table 3 is in H2O2With the neuroprotection 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 indicates that：Preliminary cell model screening is entered to identified compound, compound 1 embodies neural guarantor
Shield activity, i.e., in H2O2There is good neuroprotective activity in damage primary neuronal models, its activity is with being better than Yi Dala
Give.
The invention further relates to the pharmaceutical composition using the compounds of this invention as active component.The pharmaceutical composition can basis
It is prepared by method well known in the art.Can be by by the compounds of this invention and one or more pharmaceutically acceptable solids or liquid
Excipient and/or assistant agent combine, and any formulation used suitable for human or animal is made.The compounds of this invention is in its pharmaceutical composition
In content be usually 0.1-95 weight %.
The compound of the present invention can be administered in a unit containing its pharmaceutical composition, and method of administration can be intestines
Road or non-bowel, such as oral, nasal cavity, oral mucosa, skin, peritonaeum, rectum.
Form of administration can be liquid dosage form, solid dosage forms or semisolid dosage form.Liquid dosage form can be solution (including
True solution and colloidal solution), emulsion (including o/w types, w/o types and emulsion), supensoid agent, injection (including liquid drugs injection, powder pin
Agent and transfusion), eye drops, nasal drop, lotion and liniment etc.；Solid dosage forms can be that tablet (including ordinary tablet, enteric coatel tablets, contains
Piece, dispersible tablet, chewable tablets, effervescent tablet, oral disnitegration tablet), capsule (including hard shell capsules, soft capsule, capsulae enterosolubilis), particle
Agent, powder, micropill, dripping pill, suppository, film, paster, the agent of gas (powder) mist, spray etc.；Semisolid dosage form can be ointment,
Gel, paste etc..
The compound of the present invention can be made ordinary preparation, can also be sustained release preparation, controlled release preparation, targeting preparation and each
Kind particulate delivery system.
In order to which the compounds of this invention is made into tablet, various excipient well known in the art can be widely used, including it is dilute
Release agent, binder, wetting agent, disintegrant, lubricant, glidant.Diluent can be starch, dextrin, sucrose, glucose, breast
Sugar, mannitol, sorbierite, xylitol, microcrystalline cellulose, calcium sulfate, calcium monohydrogen phosphate, calcium carbonate etc.；Wetting agent can be water, second
Alcohol, isopropanol etc.；Adhesive can be starch slurry, dextrin, syrup, honey, glucose solution, microcrystalline cellulose, Arabic gum
Slurry, gelatine size, sodium carboxymethylcellulose, methylcellulose, hydroxypropyl methyl cellulose, ethyl cellulose, acrylic resin, card
Ripple nurse, polyvinylpyrrolidone, polyethylene glycol etc.；Disintegrant can be dried starch, microcrystalline cellulose, low substituted hydroxy-propyl fiber
Element, PVPP, Ac-Di-Sol, sodium carboxymethyl starch, sodium acid carbonate and citric acid, polyoxy second
Alkene sorbitan fatty acid ester, dodecyl sodium sulfate etc.；Lubricant and glidant can be talcum powder, silica, tristearin
Hydrochlorate, tartaric acid, atoleine, polyethylene glycol etc..
Tablet can also be further made to coating tablet, such as sugar coated tablet, thin membrane coated tablet, enteric coated tablets, or it is double
Synusia and multilayer tablet.
In order to which administration unit is made into capsule, active ingredient the compounds of this invention and diluent, glidant can be mixed
Close, mixture is placed directly within hard shell capsules or soft capsule.Also can active ingredient the compounds of this invention is first and diluent, bonding
Particle or micropill is made in agent, disintegrant, then is placed in hard shell capsules or soft capsule.For preparing each dilute of the compounds of this invention tablet
Release agent, binder, wetting agent, disintegrant, glidant kind can also be used for preparing the capsule of the compounds of this invention.
For the compounds of this invention is made into injection, water, ethanol, isopropanol, propane diols or their mixture can be used
Make solvent and add appropriate solubilizer commonly used in the art, cosolvent, pH adjustments agent, osmotic pressure regulator.Solubilizer 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..Such as prepare lyophilized
Powder-injection, it can also add mannitol, glucose etc. and be used as proppant.
In addition, if desired, colouring agent, preservative, spices, flavouring or other additions can also be added into pharmaceutical preparation
Agent.
To reach medication purpose, strengthen therapeutic effect, medicine of the invention or pharmaceutical composition known can be given with any
Prescription method is administered.
The dosage of the compounds of this invention pharmaceutical composition is according to the property and serious journey to be prevented or treated disease
The individual instances of degree, patient or animal, method of administration and formulation etc. can have large-scale change.In general, the present inventionization
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
Unit administration is measured, this depends on the clinical experience of doctor and including the dosage regimen with other treatment means.
The compound or composition of the present invention can individually be taken, or merge use with other treatment medicine or symptomatic drugs.
When the compound of the present invention exists with other medicines to act synergistically, its dosage should be adjusted according to actual conditions.
Claims (7)
1. new Phenylpropanoid Glycosides in wild anise, it is characterised in that there is structure shown in 1
1。
2. the preparation method of compound as shown in claim 1, it is characterised in that include per the mg of prepare compound 1,5 following
Step：
A. the wild anistree kg of fruit 10.50 dried, crush, after soaking 2 h with the L of 95% EtOH 80, heating and refluxing extraction 3 times,
2 hours every time, extract solution was concentrated under reduced pressure, and obtained 261.2 g medicinal extract；
B. medicinal extract is dissolved in methanol, is adsorbed in 500 g diatomite, dry, load apparatus,Soxhlet's, successively with petroleum ether,
Ethyl acetate and Soxhlet extraction with methanol extraction；
C. each extract solution is concentrated under reduced pressure to obtain petroleum ether part 44.2 g, the g of ethyl acetate extract 75.0 and methanol position 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, the isolated fraction Fr1-Fr6 of gradient elution；
E. to 6 g, Fr3 is by middle compression leg chromatography, 10-60 % methanol elution gradient, is divided into 40 fractions, and every 500
Ml is 1 part, and new [(5 mg, MeCN-a H of Phenylpropanoid Glycosides 1 is obtained from Fr. 3-1 by preparing liquid phase2O (20:80), t R= 35
min)]。
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 characterized in that the cerebrovascular disease medicament is nerve protection medicine.
5. the application according to claim 3, it is characterized in that the cranial vascular disease be cerebral apoplexy, dementia, neuroinflamation,
Heavy metal poisoning, never poison poisoning.
6. the application according to claim 5, it is characterized in that the cerebral apoplexy is cerebral arterial thrombosis or hemorrhagic brain soldier
In.
7. a kind of pharmaceutical composition, it is characterised in that containing acceptable in the compound and pharmacodynamics shown in claim 1
Carrier.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710714049.7A CN107445840A (en) | 2017-08-18 | 2017-08-18 | Wild anistree new Phenylpropanoid Glycosides and preparation method thereof, application and pharmaceutical composition |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710714049.7A CN107445840A (en) | 2017-08-18 | 2017-08-18 | Wild anistree new Phenylpropanoid Glycosides and preparation method thereof, application and pharmaceutical composition |
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| Publication Number | Publication Date |
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| CN107445840A true CN107445840A (en) | 2017-12-08 |
Family
ID=60492806
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106543133A (en) * | 2016-11-22 | 2017-03-29 | 华北理工大学 | Wild anistree new isopentene group replaces C6‑C3Class compound and preparation method thereof, application and its pharmaceutical composition |
-
2017
- 2017-08-18 CN CN201710714049.7A patent/CN107445840A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106543133A (en) * | 2016-11-22 | 2017-03-29 | 华北理工大学 | Wild anistree new isopentene group replaces C6‑C3Class compound and preparation method thereof, application and its pharmaceutical composition |
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