CN101845034A - Preparation and application method of scutellarin - Google Patents
Preparation and application method of scutellarin Download PDFInfo
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- CN101845034A CN101845034A CN201010197654A CN201010197654A CN101845034A CN 101845034 A CN101845034 A CN 101845034A CN 201010197654 A CN201010197654 A CN 201010197654A CN 201010197654 A CN201010197654 A CN 201010197654A CN 101845034 A CN101845034 A CN 101845034A
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Abstract
The invention discloses a preparation method of scutellarin, comprising the following steps of: (1) refluxing and extracting a medicinal material of erigeron breviscapus with ethanol; (2) filtering a leaching solution in the last step and carrying out pressure reduction to recover ethanol to obtain extract for later use; (3) respectively extracting with petroleum ether, ethyl acetate and normal butanol to obtain a petroleum ether extraction part, an ethyl acetate extraction part and a normal butanol extraction part; (4) dissolving the ethyl acetate part with ethanol; (5) adding silica gel and stirring, naturally drying, porphyrizing and sieving to obtain fine powder; (6) through gel column chromatography, carrying out gradient elution on the petroleum ether and the ethyl acetate and collecting by section; and (7) carrying out gel column chromatography on the ethyl acetate extraction part and elution by the petroleum ether and isopropanol and checking and combining same speckle parts according to a thin layer to obtain a compound of scutellarin. The scutellarin extract is used as an active component and is used for preparing a medicine for preventing and treating neurodegenerative diseases. The method can be used for preparing the scutellarin the purity of which is as high as 95 percent; and the raw material can be used for preparing a medicine for treating senile dementia and serves the human health.
Description
Technical field
The present invention relates to the preparation of medical material,, also relate to its application method in particular to the preparation method of scutellarin.
Background technology
The Herba Erigerontis (Herba Erigerontis) that mainly is distributed in ground such as Guizhou, Hunan, Guangxi is the dry herb of feverfew Erigeron breviscapus (Vant.) Hand.-Mazz. (Ergeron breviscapus), has expelling wind and cold, an effect of the activating collaterals to relieve pain of invigorating blood circulation.Think that at present Herba Erigerontis and extract thereof can improve the acute cerebral infarction clinical symptom, strengthen the recovery of acute ischemic cerebral apoplexy patient neural function, cerebral ischemia is had obvious provide protection, the glaucoma optic nerve is had provide protection; Coronary artery dilator increases myocardial blood flow, reduces that thrombocyte gathers, microcirculation improvement, improves effect such as coronary heart disease and angina pectoris.
Herba Erigerontis is the clinical single medicinal material of widely using.So far from Herba Erigerontis, separate, identify flavonoid compound, caffeic acid ester compounds, phenolic acid compound and other compounds.The Herba Erigerontis injection main component of using clinically is the water decoction-alcohol sedimentation composition of Erigeron breviscapus (Vant.) Hand.-Mazz. at present, is mainly flavones ingredient and caffeoyl compounds etc., is used for the treatment of hypertension, coronary heart disease etc. more.Breviscarpine is a flavonoids effective constituent, mainly contains scutellarin and breviscapine etc.Breviscarpine has antiplatelet, antithrombotic, and effects such as protection cerebral tissue are widely used in ischemic cardio cerebrovascular diseases and diabetes such as cerebral thrombosis, coronary heart disease, stenocardia.Pharmacological mechanism research to monomer component material in the Herba Erigerontis has at present also obtained certain achievement.Scutellarin (having another name called scutellarin) is considered to the main pharmacological component of Breviscarpine, and energy microcirculation improvement and brain metabolism improve mouse study, memory capability.It can vasodilation, reduce platelet count and suppress platelet aggregation; Hydroxy radical qiao, superoxide anion and hydrogen peroxide there are good scavenging(action), can reduce Ca in damage of rat cerebral cortex cynapse oxidative stress and the cell
2+Level is improved cell membrane fluidity and Na
+/ K
+-atpase activity; Can also dose-dependently ground suppress the generation of lipid peroxidation product mda (MDA), and impel sulfydryl membranin content to descend, the reduction of mitochondrial swelling and membrane potential is had certain restraining effect.In addition, scutellarin can also promote the retinal neuronal cell survival of vitro culture, and liver injury is had significant protective effect.
In recent years, people are in the preparation of studying scutellarin and obtained some achievements aspect the curative effect of disease, for example No. 02116795.8, Chinese patent application part " process for preparing novel medicine with Breviscarpine of function of promoting blood circulation to disperse blood clots ", number 03117754.9 " erigeron breviscapus and preparation method thereof and the application in pharmacy ", number 03130257.2 " preparation of a kind of administrated by injection that contains the scutellarin activeconstituents and preparation method thereof ", number 03135215.4 " preparation method of scutellarin complex salts and preparation thereof ", number 200410000002.7 " a kind of highly purified breviscapine B injection agent nucleic acid isothermal amplification method ", number 200510112608.4 " a kind of preparation method of Herba Erigerontis injection formulations and application thereof ", number 200710024887.8 " being scutellarin prodrug of carrier and preparation method thereof with the poly-aspartate derivant ", number 200710024888.2 " being scutellarin prodrug of carrier and preparation method thereof with the cm-chitosan ", number 200710176662.4 " scutellarin and medical use thereof ", 200710201189.0 number " a kind of treatment diseases of cardiovascular and cerebrovascular systems, the pharmaceutical composition of regulating blood fat ", number 200810010208.6 " new scutellarin compounds and application thereof ", 200810045869.2 number " Scutellarein carbamate derivates, Preparation Method And The Use ".But these patents or application part do not have too many report for the preparation method of scutellarin activeconstituents.
Summary of the invention
The object of the present invention is to provide the preparation method of scutellarin, thus for research and development be that the medicine of raw material provides basic condition with its activeconstituents.
Another purpose of the present invention provides the application method of scutellarin, and it is utilized in pharmaceutical industry.
The contriver is through research repeatedly, and the preparation method of the scutellarin that provides may further comprise the steps:
(1) the Herba Erigerontis medicinal material is leached with alcohol reflux;
(2) leaching liquid with previous step filters, decompression recycling ethanol, and it is standby to get medicinal extract;
(3) use sherwood oil respectively, ethyl acetate, n-butanol extraction gets the petroleum ether extraction part, ethyl acetate extraction part, n-butanol extraction part;
(4) ethyl acetate extraction part dissolve with ethanol;
(5) add silica gel and stir, dry naturally, porphyrize sieves, and obtains fine powder;
(6) through silica gel column chromatography, with sherwood oil, ethyl acetate gradient elution, Fractional Collections;
(7) ethyl acetate extraction part with sherwood oil, Virahol wash-out, merges same blob part according to the thin layer inspection through silica gel column chromatography, makes the compound scutellarin.
The described alcoholic acid massfraction of the 1st step of aforesaid method is 90%, and its consumption is 8 times of quality of medicinal material, leaches each 1.5 hours 3 times.
The pressure-controlling of the described decompression recycling ethanol of the 2nd step of aforesaid method is at 0.08MPa.
The massfraction of the described sherwood oil of the 3rd step of aforesaid method, ethyl acetate, propyl carbinol is respectively 2%, 2%, 3%.
The described alcoholic acid massfraction of the 4th step of aforesaid method is 1.7%, and the ethanol consumption is 10 times of extraction part quality.
The described silica gel of the 5th step of aforesaid method is the normal phase column chromatographic silica gel, and its fineness is 200～300 orders; Consumption is 10 times of quality of medicinal material; Described porphyrize sieves to crossing 8 mesh sieves.
The silica gel fineness is 200～300 orders in the described silica gel column chromatography of the 6th step of aforesaid method; Described with sherwood oil, ethyl acetate gradient elution, the mass ratio of sherwood oil and ethyl acetate is 7: 3～0: 10.
The silica gel fineness is 200～300 orders in the described silica gel column chromatography of the 7th step of aforesaid method; The mass ratio of described sherwood oil, Virahol is 20: 1.
For the scutellarin with method for preparing is applied to treat senile dementia, the contriver has passed through animal experiment study scutellarin neuroprotective mechanism and the effect in senile dementia treatment.Its process comprises:
1, modelling, experiment grouping and pharmacological agent Wistar rat (male and female half and half) all carry out the test of Morris water maze, and ability of learning and memory is suitable.Be divided into normal control group (n=6), sham operated rats (n=6), model group (n=10), Herba Erigerontis group (n=10) and piracetam group (n=10) at random.The three groups of rats in back are used ventricles of the brain orientator fixing head after 10% Chloral Hydrate (0.3g/kg) intraperitoneal anesthesia, with the bregma is coordinate, 3mm behind the bregma, 2mm is opened on the side, dark 3.3mm is the intracerebroventricular injection point, and the back, location is bored with cranial drill and opened skull, the vertical inserting needle of microsyringe, carry out the bilateral intracerebroventricular, slowly inject the inferior maple of diformazan and hatch state of aggregation amyloid-beta (A β) after 72 hours
25-35(5 μ g/ μ L) each 2 μ L, let the acupuncture needle remain at a certain point 10 minutes, sew up a wound, and it is anti-infective to give the external application of Sulphadiazine Sodium powder, and second day after operation gives 1%D-gal 0.72mg/100g/ days abdominal injection, continuous ten days.Sham operated rats simulation model group bilateral intracerebroventricular and abdominal injection equivalent physiological saline.Wherein the Herba Erigerontis group was irritated stomach by 0.5% Herba Erigerontis 2ml/ days after modelling, and the piracetam group is pressed the 64mg/mL suspension equally and irritated stomach in 2mL/ days; All groups are all used the determined with Morris water ability of learning and memory in modelling after 30 days; Test and get blood from rat femoral after 24 hours, blood plasma is drawn in centrifugal back; Take out the left occipital lobe cerebral tissue after the animal sacrificed by exsanguination at low temperatures and put-80 ° of refrigerators standby (mensuration cholinesterase activity).
2, the mensuration water maze of ability of learning and memory is made up of round pool, safety island and register system 3 parts, pool diameter 120cm, and the high 60cm of bucket, the water surface is higher than safety island 3cm, water temperature (20 ± 1) ℃, the peace and quiet of training period environment, the labyrinth object of reference is constant.4 place of entry of pool wall mark are divided into 4 quadrants with the pond, and register system is the study of behaviour detection module of BI2000 system, and experimental rat detects its ability of learning and memory respectively at carrying out constant-bearing navigation and space exploration experiment before and after the drug treatment.That is: carried out the constant-bearing navigation test in 1-4 days: put into water from each place of entry by pool wall by I, II, III, IV quadrant order with rat every day, and rat is escape latency from entry to climbing up platform (being fixed in the I quadrant) required time in the record 60s.Every day, continuously tested was 4 times, continuous 5 days, got its mean value.Removed platform on the 5th day, and carried out the space exploration experiment: the record rat is passed through the number of times that passes former gate position in former platform time and the 1min the 1st time.
3, cerebral tissue and plasma A ChE and BuChE determination of activity rats with left occipital lobe cerebral tissue precision are weighed, add protein lysate in 1: 15 ratio and pour the homogenate of homogenizer ice bath into, 15% brain homogenate for preparing is got supernatant liquor with 12000r/min behind the centrifugal 30min on 4 ℃ of refrigerated centrifuges, press 1: 13 dilution proportion with PBS; With the centrifugal 15min separated plasma of 3000r/min, press 1: 5 dilution proportion after the rat femoral bloodletting with PBS.Press the test kit description operation, the reaction system mixing, room temperature lucifuge reaction 20min, termination reaction is respectively managed absorbancy (returning to zero with PBS) in 412nm wavelength mensuration then, calculates blood plasma and AChE of brain tissue homogenate and BuChE activity by following formula.
(measuring pipe-control tube) * coefficient (0.588) * extension rate
4, histopathology morphological observation
4.1 the normal dyeing ice bath takes out cerebral tissue, sample is taken from the profile apart from centre joint 0.2cm place, after promptly give 4% Paraformaldehyde 96 and fix, conventional dehydration, transparent, waxdip, embedding, section, slice thickness 5 μ m, HE dyeing, light microscopic is the observation morphological changes of various tissue components down.
Paraffin embedding is carried out with ordinary method in the back 4.2 Nissl's staining is drawn materials, and gets the section of 5 μ m thickness, with the dyeing of Nissl method, observes under light microscopic.Choose rat cerebral cortex frontal lobe zone, get (* 400) positive cell number mean value under 8 high power fields at random, carry out statistical procedures.
5, the active mensuration of oxidative stress index S OD and MAO
Ice bath is preparation 10% right side frontal lobe brain tissue homogenate down, and is centrifugal, gets supernatant liquor.Press kit method and measure the SOD activity with xanthine oxidase respectively, wavelength 550nm place measures its light absorption value; With biochemical determination MDA content, wavelength 242nm place measures its light absorption value.
6, apoptosis percentage in the Flow cytometry rat brain rat cortex neural cell group
The rat brain left side temporal lobe that ice bath is taken out is organized and is placed plate immediately, with eye scissors tissue is shredded, and blows and beats to suspension repeatedly with plastics suction nozzle absorption PBS damping fluid again.Suspension in the plate is removed cell mass with clean filtered through gauze, and 5ml test tube collecting cell suspension leaves heart 5min with 1000, abandons supernatant, vibration mixing (if after centrifugal red corpuscle is arranged, then dissolve away red corpuscle with the about 500 μ l of hemolysin, centrifugal wash once again); Getting concentration is 1 * 10
6Cell/ml single cell suspension 50 μ l (every test tube remaining cell suspension is as negative control) add Annexin V, PI dyestuff 5 μ l, behind 4 ℃ of refrigerator lucifuge dyeing 15min, add about 300 μ l buffer diluents respectively to all test tubes to be measured, shake up the back and go up machine testing.Tie detection and interpretation of result with the CellQuest software of U.S. Becton-Dickinson company.
7, the protein expression level of rat cerebral cortex a4, a7 nicotine receptor is measured
With glass homogenizer rat right side frontal lobe is organized in homogenate on ice, and extracts total protein, carry out quantitative back with reference to Guan
[3]Deng method detect α 4, α 7 and β 2nAChR subunit protein level with western trace (Western blotting) method.With the Labworks software analysis as a result the time with β-actin protein band as internal reference, calculate the relative level ratio that protein alpha 4, α 7 and β 2nAChR band and the percent value of β-actin protein band pixel grey scale are expressed as protein alpha 4, α 7 and β 2nAChR.
Studies show that scutellarin improves significantly to the ability of learning and memory of intending the AD rat model, can weaken and intend AD rat model cerebral tissue AChE and the active rising of BuChE; The active cranial nerve cell apoptosis that reduces and weaken plan AD rat model of plasma A ChE and BuChE, the reduction of the enhancing of oxidative stress and cerebral tissue right side frontal lobe α 4 and α 7 nicotine receptor levels.Show that scutellarin can resist the neurotoxic effect of amyloid-beta, has certain neuroprotective.This will play an important role in the treatment of senile dementia.
The application method of scutellarin provided by the invention is that the scutellarin extract is used for preparation at prevention and treatment Alzheimer nerve degenerative diseases medicines such as (being presenile dementia) as activeconstituents.
Method of the present invention can prepare purity up to 95% scutellarin, utilizes this raw material to can be made into the medicine of treatment senile dementia, is the mankind's health service.
Embodiment
Following examples can further specify the present invention, but embodiment not delimit the scope of the invention.
Embodiment
At first, getting Herba Erigerontis medicinal material 15.0kg, is 90% alcohol reflux leaching 3 times with the massfraction of 8 times of amounts, each 1.5 hours.
Then, the leaching liquid filtration with previous step is decompressed to 0.08MPa, reclaims ethanol, obtains medicinal extract, and is standby.
Afterwards, use the sherwood oil of massfraction 2% respectively, the ethyl acetate of massfraction 2%, the medicinal extract of the propyl carbinol system extraction previous step of massfraction 3% gets sherwood oil part 120.0g, ethyl acetate part 180.0g, propyl carbinol part 330.0g.
The ethyl acetate part 180.0g of previous step is 1.7% dissolve with ethanol with a small amount of massfraction;
Add 150.0g 250 purpose silica gel (being the normal phase column chromatographic silica gel) and stir, dry naturally, porphyrize is crossed 80 mesh sieves; Through 1200.0g 300 order silica gel column chromatographies, use sherwood oil again: the ratio of ethyl acetate is to carry out gradient elution, Fractional Collections, 1000mL/ part at 8: 2;
Ethyl acetate part the 1st part, through silica gel column chromatography, use sherwood oil: Virahol is 20: 1 a mixing solutions wash-out, merges the same blob part according to the thin layer inspection, gets the compound scutellarin.
Claims (9)
1. the preparation method of scutellarin, its feature may further comprise the steps:
(1) the Herba Erigerontis medicinal material is leached with alcohol reflux;
(2) leaching liquid with previous step filters, decompression recycling ethanol, and it is standby to get medicinal extract;
(3) use sherwood oil respectively, ethyl acetate, n-butanol extraction gets the petroleum ether extraction part, ethyl acetate extraction part, n-butanol extraction part;
(4) ethyl acetate extraction part dissolve with ethanol;
(5) add silica gel and stir, dry naturally, porphyrize sieves, and obtains fine powder;
(6) through silica gel column chromatography, with sherwood oil, ethyl acetate gradient elution, Fractional Collections;
(7) ethyl acetate extraction part with sherwood oil, Virahol wash-out, merges same blob part according to the thin layer inspection through silica gel column chromatography, makes the compound scutellarin.
2. in accordance with the method for claim 1, it is characterized in that described alcoholic acid massfraction of the 1st step is 90%, its consumption is 8 times of quality of medicinal material, leaches each 1.5 hours 3 times.
3. in accordance with the method for claim 1, it is characterized in that the pressure-controlling of described decompression recycling ethanol of the 2nd step is at 0.08MPa.
4. in accordance with the method for claim 1, it is characterized in that described sherwood oil, the ethyl acetate of method, the massfraction of propyl carbinol are respectively 2%, 2%, 3%.
5. in accordance with the method for claim 1, it is characterized in that described alcoholic acid massfraction of the 4th step is 1.7%, the ethanol consumption is 10 times of extraction part quality.
6. in accordance with the method for claim 1, it is characterized in that described silica gel of the 5th step is the normal phase column chromatographic silica gel, its fineness is 200～300 orders; Consumption is 10 times of quality of medicinal material; Described porphyrize, sieve and be to cross 8 mesh sieves.
7. in accordance with the method for claim 1, it is characterized in that the silica gel fineness is 200～300 orders in the described silica gel column chromatography of the 6th step; Described with sherwood oil, ethyl acetate gradient elution, the mass ratio of sherwood oil and ethyl acetate is 7: 3～0: 10.
8. in accordance with the method for claim 1, it is characterized in that the silica gel fineness is 200～300 orders in the described silica gel column chromatography of the 7th step; The mass ratio of described sherwood oil, Virahol is 20: 1.
9. the application method of the scutellarin that makes according to the described method of claim 1 is characterized in that the scutellarin extract is used for preparation at nerve degenerative diseases medicines such as prevention and treatment Alzheimers as activeconstituents.
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| CN102000101A (en) * | 2010-10-28 | 2011-04-06 | 天津中医药大学 | Application of scutellarin to treatment of microglia-mediated diseases |
| CN102613185A (en) * | 2012-01-16 | 2012-08-01 | 中国科学院昆明植物研究所 | Parahormone promoting plant root elongation and application thereof |
| CN102993249A (en) * | 2011-09-19 | 2013-03-27 | 昆明龙津药业股份有限公司 | Preparation method of breviscapine crude drug |
| CN105925634A (en) * | 2016-05-06 | 2016-09-07 | 浙江工业大学 | Method for preparing scutellarein through biological transformation of scutellarin |
| CN106692289A (en) * | 2015-11-17 | 2017-05-24 | 上海中医药大学 | Medical application of alcohol extract of sculellaria barbata |
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| CN102000101A (en) * | 2010-10-28 | 2011-04-06 | 天津中医药大学 | Application of scutellarin to treatment of microglia-mediated diseases |
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| CN106692289A (en) * | 2015-11-17 | 2017-05-24 | 上海中医药大学 | Medical application of alcohol extract of sculellaria barbata |
| CN106692289B (en) * | 2015-11-17 | 2020-06-26 | 上海中医药大学 | Medical application of barbat skullcap alcohol extract |
| CN105925634A (en) * | 2016-05-06 | 2016-09-07 | 浙江工业大学 | Method for preparing scutellarein through biological transformation of scutellarin |
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Application publication date: 20100929 |