CN1215071C - Erigeron ester B and its preparation method as well as application in pharmacy - Google Patents
Erigeron ester B and its preparation method as well as application in pharmacy Download PDFInfo
- Publication number
- CN1215071C CN1215071C CN 03117753 CN03117753A CN1215071C CN 1215071 C CN1215071 C CN 1215071C CN 03117753 CN03117753 CN 03117753 CN 03117753 A CN03117753 A CN 03117753A CN 1215071 C CN1215071 C CN 1215071C
- Authority
- CN
- China
- Prior art keywords
- erigeroster
- compound
- erigeron
- preparation
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to the erigeron ester B of a new caffeic acid ester component of a structural formula (I), which can be obtained by extraction and separation from a drying whole herb of erigeron fleabane of compositae. The compound (I) has the advantages of anti-platelet aggregation, oxidation resistance and blood vessel activity dilatation, and can be used as a medicament for treating cardiovascular and cerebrovascular diseases.
Description
1, technical field
The present invention relates to a kind of treatment active new compound Erigeroster B of cardiovascular and cerebrovascular diseases (Erigeroster B) that has, the new compound Erigeroster B that specifically from Herba Erigerontis, extracts (Erigeroster B), preparation method and the application in pharmacy.
2, background technology
Cardiovascular and cerebrovascular diseases is increasing, and it is in a bad way, and is first reason that the mankind die of illness, thereby its morbidity also receives the world of medicine and social especially concern with treatment.Economic development in addition, aging population, the elderly's cardiovascular and cerebrovascular diseases is many again, makes problem more sharp-pointed.Herba Erigerontis has another name called Herba Erigerontis, is the dry herb of composite family bitter fleabane platymiscium Erigeron breviscapus (Vant.) Hand.-Mazz. Erigeron breviscapus (Vant.) Hand.-Mazz., has expelling cold and relieving exterior syndrome, dispels rheumatism the effect of activating collaterals to relieve pain.The Zhang Renwei of institute of materia medica, Yunnan etc. is separated to flavonoid activeconstituents scutellarin first from Herba Erigerontis, and be lamp-dish flower acetic that mixture main, that contain a small amount of breviscapine (apigenin glycosides) calls Breviscarpine (breviscapin) [Zhang Renwei, Yang Shengyuan, Lin Yongyue, Acta Pharmaceutica Sinica (1981), 16 (1), 68-6].Except scutellarin, patent CN1136434 discloses two coffic acid quininic acid ester compounds 3,5-two caffeoyl quinic acids and 3,4-two caffeoyl quinic acids (3,4-dicaffeoyl quinic acid)].CN1064236C then discloses Jiao Meikangsuan (promenonic acid) and bitter fleabane glycosides (erigenoide) is being used aspect the treatment cardiovascular and cerebrovascular diseases.Zhang Weidongs etc. have been applied for activeconstituents 1-(2 '-gamma-pyrone)-6-coffee acyl-β-preparation of D-glucoside and preparation method's the patent CN1252276 that are separated to from Herba Erigerontis.More than disclosed be the patent of the new purposes of known compound, do not have the new compound patent.
3, summary of the invention:
The present invention is directed to the blank of prior art, the openly new activeconstituents Erigeroster B of the present invention the invention provides following technical scheme:
Have following structural formula compound Erigeroster B:
Erigoster B
Erigeroster B
The invention provides the method for the compound of preparation claim 1, get the herb or the over-ground part of Herba Erigerontis (Erigeronbrevicapus), pulverize, extract three times with 0-95% aqueous ethanolic solution or 0-95% aqueous acetone solution, merge No. three times extracting solution, concentrating under reduced pressure, macroporous resin chromatography on the concentrated solution, elder generation's water wash-out, use 40% ethanol elution again, collect concentrating under reduced pressure behind 40% ethanol eluate, this part with dextrane gel (Sephdex) HL-20 repeatedly purifying get Erigeroster B (Erigeroster B).
The present invention provides the application of compound Erigeroster B (Erigeroster B) in preparation prevention or treatment cancer drug simultaneously.
The compound structure data are as follows:
Molecular formula, C
26H
24O
13, molecular weight, 544.46, [α]
D,+37.14 ° (0.00175, acetone); IR (KBr compressing tablet): 2970.57-3645.31,1694.68,1632.87,1520.46,1605.84,1283.57,1162.82cm
-1
UVλ
max(MeOH)：330(22018)，302(14620)，244(5966)，218(12267)nm；
1HNMR(500Hz，pyridine-d
5，ppm，J in Hz)：2.84-2.93(2H，m，H-2α，H-2β)，6.03(1H，t，5.1，H-3)，4.72(1H，t，5.1，H-4)，4.93(1H，t，4.3，H-5)，5.07(1H，m，H-6)，5.17(1H，dd，12.3，2.7，H-9a)，6.04(1H，dd，8.8，12.3，H-9b).6.60，7.14(each 1H，d，15.8，H-2’，H-2”)，8.09，8.06(each 1H，d，15.8，H-3’，H-3”)，7.31，7.31(each 1H，dd，8.0，1.5，H-5’，H-5”)，7.18，7.18(each 1H，d，8.0，H-6’，H-6”)，7.80，7.56(each 1H，brs，H-9’，H-9”)。
13CNMR(100.62Hz，pyridine-d
5，ppm)：104.82(C-1)，38.24(C-2)，67.49(C-3)，67.40(C-4)，78.01(C-5)，80.45(C-6)，64.18(C-9)，170.97(C-10)，167.95，167.77(C-1’，C-1”)，115.97，115.23(C-2’，C-2”)，146.25，146.21(C-3’，C-3”)，127.51，127.28(C-4’，C-4”)，122.57，122.31(C-5’，C-5”)，116.84，116.79(C-6’，C-6”)，150.37，150.186(C-7’，C-7”)，147.62，147.59(C-8’，C-8”)，116.13，115.89(C-9’，C-9”)。
This compound has the unique texture skeleton, though all have two coffee acyls, is different from the known caffeoyl quinic acid of structure, is the compound of structure novelty.
The present invention is the preparation method of Erigeroster B openly, gets herb or the over-ground part of Herba Erigerontis (Erigeron brevicapus), pulverizes, and extracts three times with 0-95% aqueous ethanolic solution or aqueous acetone solution, merges No. three times extracting solution, concentrating under reduced pressure.Macroporous resin chromatography on the concentrated solution, first water wash-out uses 40% again, collects concentrating under reduced pressure behind 40% ethanol eluate, and this part is with Sephdex HL-20 just Erigeroster B (Erigeroster B) of purifying repeatedly.
The pharmacology activity research result of the open Erigeroster B of the present invention shows by pharmacological evaluation, and Erigeroster B generates external liver tissue homogenate lipid peroxidation the obvious suppression effect, shows that they have anti-oxidant activity.Induce the platelet aggregation of rat to have certain restraining effect to ADP.Inducing rabbit aorta to shrink to phyenlephrinium has the diastole effect, shows that they have the vasodilation effect.
Table 1. Erigeroster B is to the influence (in vitro) of rat liver homogenate MDA content
| Medicine | Dosage | N | MDA content (nmol/g tissue wet) | Inhibiting rate (%) |
| F (Erigeroster B) | | 32 12 10 10 | 81±21 67±10* 64±11* 52±6** | - 18 22 36 |
* P＜0.05, * * P＜0.01vs blank group.
Table 2. Erigeroster B is induced the effect of rat platelet aggregation to ADP
| Medicine | Dosage (μ g/ml) | n | MA (%) | The maximum inhibiting rate (%) of assembling | Average aggregation rate (%) | The average inhibiting rate (%) of assembling |
| Erigeroster B | Solvent control 250 750 | 7 6 7 | 79±8 75±7 71±9 | 0 5 10 | 71±9 54±18* 48±25* | 24 32 |
P＜0.05, * * P＜0.01vs solvent control group.
The influence that table 3. Erigeroster B induces rabbit aorta to shrink to phyenlephrinium
| Medicine | Concentration μ g/ ml | Sample number | Phyenlephrinium brings out antiotasis (g) | The diastole percentage | |
| Contrast before the administration | After the administration | ||||
| Solvent control F (Erigeroster B) | 100 | 1 5 9 | 4.7±0.78 4.4±0.6 | 4.3±0.6 3. ± 0.6** | 8％ 23％ |
Contrast before * P＜0.01vs administration
In view of Erigeroster B has above pharmacologically active, therefore envisioning Erigeroster B can be used for treating cardiovascular and cerebrovascular diseases.
The compound that the present invention relates to can be separately or with other medicinal permission auxiliary material make oral dosage forms such as tablet, capsule, dripping pill, granule by prior art.Cooperate the back to make injection liquid or freeze-dried separately or with the auxiliary material of other medicinal permission Erigeroster B by existing method.
The oral dosage form preparation method of compound Erigeroster B (Erigeroster B) cooperates the back to make formulations such as tablet, capsule by existing method separately or with the auxiliary material of other medicinal permission extract.
The preparation method of the injection of compound Erigeroster B (Erigeroster B) cooperates the back to make injection liquid or freeze-dried by existing method separately or with the auxiliary material of other medicinal permission extract.
Description of drawings: Fig. 1 is the structure iron of The compounds of this invention Erigeroster B.
In order to understand the present invention better, the present invention further specifies essentiality content of the present invention in conjunction with the embodiments, but content of the present invention is not limited thereto.
Embodiment 1: the extracting and preparing technique of Erigeroster B
Get the herb or the over-ground part 50kg of Herba Erigerontis (Erigeron brevicapus), pulverize, extract three times, merge No. three times extracting solution, concentrating under reduced pressure with 70% aqueous acetone solution.Macroporous resin chromatography on the concentrated solution, first water wash-out uses 40% again, collect 40% ethanol eluate after concentrating under reduced pressure get extract 800g, this part is with Sephdex HL-20 just Erigeroster B (Erigeroster B) 150g of purifying repeatedly.
The preparation technology of the tablet of embodiment 2, Erigeroster B
Tablet formulation
Erigeroster B 10g
Starch 50g
10% starch slurry 10g
Magnesium Stearate 2g
After Erigeroster B and starch mixed, add as 10% starch slurry and make softwood, cross 14 mesh sieves and granulate, dry under 70-80 ℃ of temperature, cross the whole grain of 12 mesh sieves, after adding Magnesium Stearate and mixing, be pressed into 1000, promptly.Every contains effective extract 10mg.
The capsule preparation technology of embodiment 3, Erigeroster B
The capsule prescription
Erigeroster B 10g
Starch 50g
Magnesium Stearate 2g
Add the recipe quantity Erigeroster B, after adding 80 ℃ of exsiccant starch and Magnesium Stearate and mixing, be distributed into 1000 capsules, every capsules contains extract 10mg.
The injection preparation of embodiment 4. Erigeroster Bs
The injection prescription
Erigeroster B 10g
Sodium-chlor 85g
S-WAT 2g
The 10g Erigeroster B is dissolved in the cold distilled water for injection of 5000ml, and 85g sodium-chlor, 2g S-WAT are dissolved in the distilled water for injection of 1000ml heat after mixing.Two kinds of solution are mixed, add water to 10000ml, adjusting pH value is filtered at the 5.0-7.0 filter stick, and membrane filtration adds nitrogen envelope bottle after clarity test is qualified, and at 115 ℃, 10atm pressure was sterilized 25 minutes down.
The freeze-dried preparation of injection of embodiment 5. Erigeroster Bs
Tablet formulation
Erigeroster B 10g
Sodium bicarbonate 2g
N.F,USP MANNITOL 252g
Water for injection adds to 2000ml
Get auxiliary material sodium bicarbonate, sodium-chlor, N.F,USP MANNITOL by prescription, add 1600 milliliters of dissolvings of injection water, add gac 3.2g, adsorb 30 minutes depyrogenations, remove by filter activated carbon, in filtrate, add Erigeroster B, supersound process makes dissolving, and regulating pH with 1N hydrochloric acid is 5.0～7.0, and millipore filtration filters, add the injection water to 2000ml, be packed as 1000, lyophilize, top plug, roll lid, promptly.
Claims (3)
1, have following structural formula compound Erigeroster B:
2, a kind of method for preparing the compound of claim 1, it is characterized in that getting the herb or the over-ground part of Herba Erigerontis, pulverize, extract three times, merge No. three times extracting solution with 0-95% aqueous ethanolic solution or 0-95% aqueous acetone solution, concentrating under reduced pressure, macroporous resin chromatography on the concentrated solution, first water wash-out is used 40% ethanol elution again, collect concentrating under reduced pressure behind 40% ethanol eluate, this part with SephdexHL-20 repeatedly purifying get Erigeroster B.
3, contain the medicinal compositions of the compound of right requirement 1 as the treatment cardiovascular and cerebrovascular diseases of activeconstituents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03117753 CN1215071C (en) | 2003-04-22 | 2003-04-22 | Erigeron ester B and its preparation method as well as application in pharmacy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03117753 CN1215071C (en) | 2003-04-22 | 2003-04-22 | Erigeron ester B and its preparation method as well as application in pharmacy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1462750A CN1462750A (en) | 2003-12-24 |
| CN1215071C true CN1215071C (en) | 2005-08-17 |
Family
ID=29748355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 03117753 Expired - Lifetime CN1215071C (en) | 2003-04-22 | 2003-04-22 | Erigeron ester B and its preparation method as well as application in pharmacy |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1215071C (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101632724B (en) * | 2008-07-25 | 2012-03-28 | 贵州益佰制药股份有限公司 | Application of polygonum orientale and erigeron breviscapus composition in preparing medicaments for treating cerebrovascular disease and correlative diseases |
| CN102079763B (en) * | 2009-11-30 | 2015-01-07 | 天津中医药大学 | Dioxabicyclo-octane compound, preparation method and application thereof |
| CN101974012B (en) * | 2010-10-26 | 2012-01-04 | 云南生物谷灯盏花药业有限公司 | Novel compound ethyl brevicate with pharmaceutical activity |
| CN101974011B (en) * | 2010-10-26 | 2012-01-04 | 云南生物谷灯盏花药业有限公司 | New compound methyl brevicate with medical activity |
| CN101974010B (en) * | 2010-10-26 | 2012-01-04 | 云南生物谷灯盏花药业有限公司 | New compound erigeron breviscapus acid with officinal activity |
| CN102351874B (en) * | 2011-08-24 | 2013-09-11 | 云南生物谷药业股份有限公司 | New erigeroster compound with medicinal activity |
| CN102766179B (en) * | 2012-05-18 | 2013-09-25 | 云南施普瑞生物工程有限公司 | Extraction separation method of Erigeron Breviscapus related substance |
| CN105560227A (en) * | 2015-12-30 | 2016-05-11 | 神威药业集团有限公司 | Neuroprotection use and medicine of Dandengtongnao active component Erigoster B |
-
2003
- 2003-04-22 CN CN 03117753 patent/CN1215071C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1462750A (en) | 2003-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105395919A (en) | Composition containing black fungus extract and having effect of reducing blood fat and preparation method of composition | |
| CN1723981A (en) | Novel use of extractive of Momordica grosvenori as adjuvant drug for preparing medicine | |
| CN1943618A (en) | Red sage root effective part standard extract and its preparing method and use | |
| CN100344642C (en) | Process for preparing flaxseed lignan total glycoside extract and use thereof | |
| CN1215071C (en) | Erigeron ester B and its preparation method as well as application in pharmacy | |
| CN1116894C (en) | Medicine for treating cardiovascular disease and preparation process thereof | |
| CN1462620A (en) | Powder of flenabane and its preparation method as well as application in making drugs | |
| CN1224383C (en) | Blood sugar reducing compound | |
| CN1857472A (en) | Ginsenoside composition preparation and its preparing process | |
| CN1565467A (en) | Use of cornel and its extract in preparation alpha-glucosidase inhibitor medicine | |
| CN1857441A (en) | Preparation and application of total salvianolic acid composition | |
| CN1799582A (en) | Blood sugar- and blood pressure-lowering medicine | |
| CN1887324A (en) | Chinese composition and its prepn process and quality control method | |
| CN1070226C (en) | Gallnut oil and its extraction process and application in pharmacy | |
| CN1560061A (en) | Process for extracting dioscored soap oside from dioscorea | |
| CN1193763C (en) | Rhodiola total tanning matter extract and use for preparing medicine for curing senile dementia | |
| CN1504478A (en) | Burnet general saponin extract , its preparation method and use | |
| CN101342210A (en) | Mother chrysanthemum total flavone buccal tablets and preparation method thereof | |
| CN101658542B (en) | Soft-lithospermum total phenolic acid and use thereof in pharmacy | |
| CN1839956A (en) | Pharmaceutical composition containing curcumin and its formulation | |
| CN101040905B (en) | Medicine made by selfheal for reducing blood sugar | |
| CN1887316A (en) | Chinese medicine composition and its prepn process and application | |
| CN100343266C (en) | Picrorhiza total glycoside extract and its application in preparation of liver disease medicine and preparation method | |
| CN1695649A (en) | Soft capsule of extractive from active ingredient of jingangteng, and preparation method | |
| CN1227013C (en) | Chinese medicinal preparation containing lilyturf root polysaccharide and its preparation method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CX01 | Expiry of patent term | ||
| CX01 | Expiry of patent term |
Granted publication date: 20050817 |