CN105079011B - A kind of preparation and application of the drug with antitumor action - Google Patents
A kind of preparation and application of the drug with antitumor action Download PDFInfo
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- CN105079011B CN105079011B CN201410220592.8A CN201410220592A CN105079011B CN 105079011 B CN105079011 B CN 105079011B CN 201410220592 A CN201410220592 A CN 201410220592A CN 105079011 B CN105079011 B CN 105079011B
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- sinkiangenorin
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Abstract
The present invention relates to the preparations and application of a kind of drug with antitumor action.The drug is Chinese medicine Ferula sinkiangensis seed ethanol extract and (or) isolated 3 diterpene coumarin class compounds from Ferula sinkiangensis seed and a new organic acid glucoside compound.Utilize various chromatographic separation technologies, isolated 4 monomeric compounds from the ethanol extract of Ferula sinkiangensis seed, and use Modern spectroscopy technology (IR, UV, MS, 1D, 2D-NMR) identify its chemical structure, it finally determines that it is umbelliprenin (1), lehmannolone (2), lehmannolol (3) and a noval chemical compound Sinkiangenorin C (4).Experimental studies have found that the ethanol extract and therefrom isolated compound all have preferable antitumor action.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to the preparation method of a kind of drug and in preparation treatment and (or) pre-
Application in preventing tumor drug, the drug be Ferula sinkiangensis seed and (or) seed ethanol extract or (and) therefrom separate
1 in 4 compounds (umbelliprenin, lehmannolone, lehmannolol and SinkiangenorinC) arrived
Or multiple compounds.
Background technique
Ferula sinkiangensis (Ferulasinkiangensis) is Umbelliferae asafoetide platymiscium, and there are about 150 in the platymiscium whole world
It is a variety of, it is distributed in south of europe Mediterranean, Africa the north and the Central Asia and its neighbouring area.There are about 26 kind of 1 mutation in China, wherein
Including Ferula sinkiangensis.Ferula sinkiangensis also known as RESINA FERULAE are distributed mainly on Xinjiang of China arid-desert areas, what Chinese Pharmacopoeia was included
Asafoetide is the resin of Ferula sinkiangensis and Ferula fukanensis K.M.Shen, has effects that disperse accumulation, dissipates ruffian, desinsection, is mainly used for treating in locality
Enterogastric diseases and upper respiratory disease.Ferula sinkiangensis applicating history is long, curative for effect, but active constituent therein and unclear
Chu, therefore in pharmaceutical field it should be understood that its effective substance, and seek new drug candidate.
Summary of the invention
To solve the above problems, by research, the isolated 3 sequiterpene perfume (or spice) from Ferula sinkiangensis seed ethanol extract
Beans chlorins compound (umbelliprenin, lehmannolone, lehmannolo1) and 1 new organic acid glycoside
Object is closed, and is named as Sinkiangenorin C.
Meanwhile according to an aspect of the present invention, the compound has growth inhibition effect to AGS, Hela.
In addition, according to an aspect of the present invention, the ethanol extract of Ferula sinkiangensis seed has antitumor action.
There has been no patent or document reports for the research achievement above so far.
Beneficial effects of the present invention and meaning are: making full use of the plant resources of Ferula sinkiangensis, further investigation exploitation is sought
It looks for unique chemical moieties, the stronger compound of activity, to provide the drug of new antitumoral for clinical research.
Detailed description of the invention:
The chemical structure of compound in Fig. 1 Ferula sinkiangensis with antitumor action
The nuclear magnetic spectrum of Fig. 2 compound 4
The inhibiting effect that Fig. 3 compound various concentration grows AGS, Hela cell
Specific embodiment
Disclosed technology contents, those skilled in the art will be apparent that other embodiments of the invention according to the present invention,
Following embodiments only make example.In the case where not violating present subject matter and range, various changes can be carried out to the present invention
And improvement.These variations should be within protection scope of the present invention.
The preparation of the Ferula sinkiangensis seed ethanol extract of the present invention of case study on implementation one
Ferula sinkiangensis dry seed measures the extraction of 90% alcohol reflux with 3-5 times, and extracting solution is concentrated in vacuo to obtain the final product.
Case study on implementation two: the system of 3 diterpene coumarin compounds of the invention and 1 new organic acid glycoside compounds
It is standby
Ferula sinkiangensis dry seed is extracted 3 times, each 2h with 90% alcohol reflux, combined extract, and leaching is concentrated under reduced pressure to obtain
Cream uses the aqueous solution of petroleum ether, methylene chloride, the total medicinal extract of water saturated extracting n-butyl alcohol respectively, and extract liquor is concentrated under reduced pressure into thick
Paste.Petroleum ether part is separated through silica gel column chromatography, and petroleum ether-ethyl acetate (100: 1 → 0: 1) gradient elution obtains 10
Component (Fr.1~10).Silica gel column chromatography is carried out to Fr.2,15 subgroups are obtained with chloroform-methanol (1: 0 → 0: 1) gradient elution
Divide (Fr.2-1~15), Fr.2-3 obtains compound 1 through SephadexLH-20 column chromatography separating purification.Fr.2-7 flow point is through anti-
Phase high performance liquid chromatography separation obtains compound 2 and 3.Methylene chloride position is first through normal phase silica gel chromatography, methylene chloride-methanol
(1: 0 → 0: 1) gradient elution obtains 20 components (Fr.1~20), and Fr.3 is obtained through SephadexLH-20 column chromatography separating purification
Compound 4.
The characterization of case study on implementation three 3 diterpene coumarin compounds and new organic acid glycoside compounds of the invention
It has been determined that 3 known sequiterpenes are fragrant by the physicochemical property of test compound, spectral data and by consulting literatures
The structure of legumin compound.
Compound 4 is noval chemical compound, and spectral data is shown in Table 1
The 13CATPNMR (CD3OD, 150MHz) and 1H-NMR (CD3OD, 600MHz) data of 1 compound 4 of table
Four invention compound umbelliprenin, lehmannolol and SinkiangenorinC of case study on implementation are right in vitro
Ags cell and lehmannolone are in vitro to the Cell suppression test of Hela cell.
(1) experimental drug: umbelliprenin, lehmannolol, lehmannolone, SinkiangenorinC contain
It measures up to 98% or more.
(2) reagent: human gastric cancer ags cell, human cervical carcinoma Hela cell's (Shanghai cell bank)；Fetal calf serum, RPMIl640
Culture medium (Gibco company, the U.S.)；Dimethyl sulfoxide (Sigma Co., USA)；Taxol (the limited public affairs of the glad medicine company of Shandong Shandong occasion
Department).
(3) method: cell inoculation be 10% containing mass fraction fetal calf serum, mass fraction be 2% glutamine
RPMI l640 culture solution in, at 37 DEG C, CO that volume fraction is 5%2It is cultivated in incubator.Every hole 6 × 104A cell density
It is inoculated in 96 orifice plates, every 10 μ L of hole, 5 various concentration drug (3.125,6.25,12.5,25,50 μ is added after overnight incubation
G/m1) cell mortality is measured respectively at 48h mtt assay.
(4) result: the result shows that, Ferula sinkiangensis seed ethanol extract and other 4 compounds are thin to above-mentioned tumour
Born of the same parents have different degrees of growth inhibition effect (Fig. 3): umbelliprenin, lehmannolol, SinkiangenorinC couple
The IC50 of ags cell is respectively 4.6 μ g/ml, 10.3 μ g/ml, 12.4 μ g/ml；IC50 of the lehmannolone to Hela cell
For 31.6 μ g/ml.
Claims (4)
1. a kind of compound with antitumor action, it is characterised in that: the compound is Sinkiangenorin C, described
The structure of Sinkiangenorin C is as follows:
2.Sinkiangenorin C application in preparation of anti-tumor drugs, the structure of the Sinkiangenorin C is such as
Under:
3. Sinkiangenorin C application in preparation of anti-tumor drugs according to claim 2, it is characterised in that:
The drug is capsule, granule, tablet, solution, pill or injection type.
4. Sinkiangenorin C application in preparation of anti-tumor drugs according to claim 2, it is characterised in that:
The drug is soft capsule, dry outstanding mixture, dispersible tablet, effervescent tablet, chewable tablets, oral disintegrating tablet, syrup, condensed pill, dripping pill or pellet.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201410220592.8A CN105079011B (en) | 2014-05-21 | 2014-05-21 | A kind of preparation and application of the drug with antitumor action |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201410220592.8A CN105079011B (en) | 2014-05-21 | 2014-05-21 | A kind of preparation and application of the drug with antitumor action |
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| Publication Number | Publication Date |
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| CN105079011A CN105079011A (en) | 2015-11-25 |
| CN105079011B true CN105079011B (en) | 2019-07-23 |
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| CN201410220592.8A Expired - Fee Related CN105079011B (en) | 2014-05-21 | 2014-05-21 | A kind of preparation and application of the drug with antitumor action |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105878312B (en) * | 2014-09-04 | 2020-05-01 | 中国医学科学院药用植物研究所 | Application of medicine with anti-influenza virus effect in ferula sinkiangensis seeds |
| CN109223772B (en) * | 2017-07-11 | 2021-04-06 | 中国医学科学院药用植物研究所 | Application of terpene coumarin compounds in treating gastric cancer |
| CN111646965B (en) * | 2020-06-03 | 2023-05-09 | 中国医学科学院药用植物研究所 | Compound Sinkiangenol E and application thereof in preparation of antitumor drugs |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102885864A (en) * | 2011-07-21 | 2013-01-23 | 新疆维吾尔自治区中药民族药研究所 | Application of Chinese asafoetida seed extract to preparation of antitumor medicament |
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2014
- 2014-05-21 CN CN201410220592.8A patent/CN105079011B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102885864A (en) * | 2011-07-21 | 2013-01-23 | 新疆维吾尔自治区中药民族药研究所 | Application of Chinese asafoetida seed extract to preparation of antitumor medicament |
Non-Patent Citations (3)
| Title |
|---|
| Umbelliprenin is cytotoxic against QU-DB large cell lung cancer cell line but anti-proliferative against A549 adenocarcinoma cells;Narges Khaghanzadeh等;《DARU Journal of Pharmaceutical Sciences》;20121030;第20卷(第69期);第1-6页 * |
| 新疆阿魏种子化学成分的系统预实验;王月娥等;《第六届肉苁蓉暨沙生药用植物学术研讨会论文集》;20120625;第205-209页 * |
| 臭阿魏、新疆阿魏和多伞阿魏化学成分研究;杨俊荣;《中国协和医科大学硕士学位论文 万方数据》;20061117;摘要 * |
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