CN105079011A - Preparation and application of anti-tumor medicament - Google Patents
Preparation and application of anti-tumor medicament Download PDFInfo
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- CN105079011A CN105079011A CN201410220592.8A CN201410220592A CN105079011A CN 105079011 A CN105079011 A CN 105079011A CN 201410220592 A CN201410220592 A CN 201410220592A CN 105079011 A CN105079011 A CN 105079011A
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Abstract
The invention relates to preparation and application of an anti-tumor medicament. The medicament is composed of Ferula sinkiangensis seed ethanol extract and/or three sesquiterpenoids compounds and a novel organic acid glycoside compound separated from Ferula sinkiangensis seeds. Four monomeric compounds are separated from the ethanol extract of the Ferula sinkiangensis seeds by various chromatographic separation techniques, and their chemical structures are identified by a modern spectroscopic technique (IR, UV, MS, 1D and 2D-NMR); finally, three compounds being umbelliprenin (1), lehmannolone (2), lehmannolol (3) and a novel compound being Sinkiangenorin C (4) are determined. Experimental researches show that all of the ethanol extract and the compounds separated from the ethanol extract are better in anti-tumor action.
Description
Technical field
The invention belongs to medical art, be specifically related to a kind of preparation method of medicine and the application in preparation treatment and (or) prophylaxis of tumours medicine, this medicine be Ferula sinkiangensisK.M.Shen seed and (or) seed ethanol extraction or (with) be therefrom separated 4 the compound (umbelliprenin obtained, lehmannolone, lehmannolol and SinkiangenorinC) in one or more compounds.
Background technology
Ferula sinkiangensisK.M.Shen (Ferulasinkiangensis) about has kind more than 150 for Umbelliferae Ferula plant, this platymiscium whole world, is distributed in south of europe Mediterranean, the north, Africa and the Central Asia and neighbouring area thereof.About there be 26 kind of 1 mutation in China, comprising Ferula sinkiangensisK.M.Shen.Ferula sinkiangensisK.M.Shen has another name called RESINA FERULAE, mainly be distributed in Xinjiang of China arid-desert areas, the Resina Ferulae that Chinese Pharmacopoeia is included is the resin of Ferula sinkiangensisK.M.Shen and Ferula fukanensis K.M.Shen, and it has effect of removing food stagnancy, loose painful abdominal mass, parasite killing, is mainly used in treatment gastroenteropathy and upper respiratory disease in locality.Ferula sinkiangensisK.M.Shen applicating history is long, determined curative effect, but active component wherein unclear, therefore need to understand its effective substance at pharmaceutical field, and seek new drug candidate.
Summary of the invention
For solving the problem, by research, be separated from Ferula sinkiangensisK.M.Shen seed ethanol extraction and obtain 3 diterpene coumarin compounds (umbelliprenin, lehmannolone, lehmannolo1) and 1 new organic acid glucoside compound, and called after SinkiangenorinC.
Meanwhile, according to an aspect of the present invention, described compound has growth inhibited effect to AGS, Hela.
In addition, according to an aspect of the present invention, the ethanol extraction of Ferula sinkiangensisK.M.Shen seed has antitumor action.
Above achievement in research not yet has patent or bibliographical information up to now.
Beneficial effect of the present invention and meaning are: the plant resources making full use of Ferula sinkiangensisK.M.Shen, and further investigation exploitation, finds and have unique chemical moieties, and active stronger compound, to providing the medicine of new antitumoral for clinical research.
Accompanying drawing explanation
There is in Fig. 1 Ferula sinkiangensisK.M.Shen the chemical constitution of the compound of antitumor action
The nuclear magnetic spectrum of Fig. 2 compound 4
Fig. 3 compound variable concentrations is to the inhibitory action of AGS, Hela Growth of Cells
Detailed description of the invention
Technology contents disclosed according to the present invention, very clear other embodiments of the present invention of those skilled in the art, following embodiment only makes example.When not violating purport of the present invention and scope, various changes and improvements can be carried out to the present invention.These changes should within protection scope of the present invention.
The preparation of case study on implementation one Ferula sinkiangensisK.M.Shen seed of the present invention ethanol extraction
Ferula sinkiangensisK.M.Shen dry seed and 3-5 times amount 90%7 alcohol reflux extract, extracting solution vacuum concentration and get final product.
Case study on implementation two: the preparation of the present invention's 3 diterpene coumarin compounds and 1 new organic acid glycoside compounds
Ferula sinkiangensisK.M.Shen dry seed 90% alcohol reflux 3 times, each 2h, merge extractive liquid, concentrating under reduced pressure obtains extractum, and use the aqueous solution of petroleum ether, dichloromethane, the total extractum of water saturated n-butanol extraction respectively, extract is evaporated to paste.Petroleum ether part is separated through silica gel column chromatography, petroleum ether-ethyl acetate (100: 1 → 0: 1) gradient elution, obtains 10 components (Fr.1 ~ 10).Carry out silica gel column chromatography to Fr.2, obtain 15 subfractions (Fr.2-1 ~ 15) with chloroform-methanol (1: 0 → 0: 1) gradient elution, Fr.2-3 obtains compound 1 through SephadexLH-20 column chromatography separating purification.Fr.2-7 flow point is separated through reversed-phase high-performance liquid chromatography, obtains compound 2 and 3.Dichloromethane position is first through normal phase silica gel chromatography, and methylene chloride-methanol (1: 0 → 0: 1) gradient elution, obtain 20 components (Fr.1 ~ 20), Fr.3 obtains compound 4 through SephadexLH-20 column chromatography separating purification.
The sign of case study on implementation three the present invention 3 diterpene coumarin compounds and new organic acid glycoside compounds
Through the physicochemical property of test compounds, spectral data determined the structure of 3 known diterpene coumarin compounds by By consulting literatures.
Compound 4 is noval chemical compound, and its spectral data is in table 1
Table 1 compound 4
13cATPNMR (CD
3oD, 150MHz) and
1h-NMR (CD
3oD, 600MHz) data
Umbelliprenin, lehmannolol and SinkiangenorinC are external to ags cell for case study on implementation four invention compound, and the external Cell suppression test room to Hela cell of lehmannolone.
(1) Experimental agents: umbelliprenin, lehmannolol, lehmannolone, SinkiangenorinC content reaches more than 98%.
(2) reagent: people's gastric cancer ags cell, human cervical carcinoma Hela cell's (Shanghai cell bank); Hyclone, RPMIl640 culture medium (Gibco company of the U.S.); Dimethyl sulfoxide (Sigma Co., USA); Paclitaxel (Shandong Lukang Cisen Pharmaceutical Co., Ltd).
(3) method: hyclone, mass fraction that it is 10% that cell is seeded in containing mass fraction are in the RPMll640 culture fluid of the glutamine of 2%, and at 37 DEG C, volume fraction is the CO of 5%
2cultivate in incubator.Every hole 6 × 10
4individual cell density is inoculated in 96 orifice plates, every hole 10 μ L, adds 5 and measure cell mortality without acute drug (3.125,6.25,12.5,25,50 μ g/m1) respectively at 48h mtt assay after overnight incubation.
(4) result: result shows, Ferula sinkiangensisK.M.Shen seed ethanol extraction and other 4 compounds all have growth inhibited effect (Fig. 3) in various degree to above-mentioned tumor cell: umbelliprenin, lehmannolol, the IC50 of SinkiangenorinC to ags cell is respectively 4.6 μ g/ml, 10.3 μ g/ml, 12.4 μ g/ml; Lehmannolone is 31.6 μ g/ml to the IC50 of Hela cell.
Claims (6)
1. the present invention relates to a kind of medicine with antitumor action, it is characterized in that: this medicine be Ferula sinkiangensisK.M.Shen seed and (or) seed ethanol extraction or (with) one or more compounds in 3 diterpene coumarin compounds and (or) a new organic acid glucoside compound.
2. according to the diterpene coumarin of 3 described in claim l and 1 new organic acid glucosides constituents, it is characterized in that: these compounds are be separated in the alcohol extract of Ferula sinkiangensisK.M.Shen seed to obtain, be respectively umbelliprenin (1), lehmannolone (2), lehmannolol (3), SinkiangenorinC (4); Compound 4 is white amorphous powder, HR-ESI-MSm/z355.1160 (calcdforC
14h
27o
10[M+H
2o]
-, 355.1160);
uV (MeOH) λ
max(log ε) 202 (2.01) nm; IR (film) v
max1739cm
-1.
3. a kind of medicine with antitumor action according to right l, it is characterized in that: the capsule (soft capsule) that described medicine can be processed into for Ferula sinkiangensisK.M.Shen seed and Ferula sinkiangensisK.M.Shen seed extract, granule (dry outstanding mixture), tablet (dispersible tablet, effervescent tablet, chewable tablet, oral cavity disintegration tablet), solution (syrup), pill (concentrated pill, drop pill, micropill), or be injection type.
4. described in claim 1 ~ 2 is Ferula sinkiangensisK.M.Shen seed ethanol extraction and (or) umbelliprenin, ehmannolone, lehmannolol, the anti-tumor activity of the one or more compounds in SinkiangenorinC4 compound.
5. described in claim l ~ 2 is Ferula sinkiangensisK.M.Shen seed ethanol extraction and (or) umbelliprenin, one or more compounds in lehmannolone, lehmannolol and SinkiangenorinC4 compound are preparing the application in clinical antitumor agents.
6. described in claim 1 ~ 2 is Ferula sinkiangensisK.M.Shen seed ethanol extraction and (or) umbelliprenin, the application of one or more compounds in lehmannolone, lehmannolol and SinkiangenorinC4 compound in the health product of preparation auxiliary treatment clinical antineoplastic.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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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| 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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| CN105079011A true CN105079011A (en) | 2015-11-25 |
| CN105079011B CN105079011B (en) | 2019-07-23 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105878312A (en) * | 2014-09-04 | 2016-08-24 | 中国医学科学院药用植物研究所 | Application of a medicine with anti-influenza virus effect in ferula sinkiangensis seeds |
| CN109223772A (en) * | 2017-07-11 | 2019-01-18 | 中国医学科学院药用植物研究所 | Application of the terpene coumarin kind compound in terms for the treatment of gastric cancer |
| CN111646965A (en) * | 2020-06-03 | 2020-09-11 | 中国医学科学院药用植物研究所 | Compound Sinkiangel 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 |
-
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 |
|---|
| NARGES KHAGHANZADEH等: "Umbelliprenin is cytotoxic against QU-DB large cell lung cancer cell line but anti-proliferative against A549 adenocarcinoma cells", 《DARU JOURNAL OF PHARMACEUTICAL SCIENCES》 * |
| 杨俊荣: "臭阿魏、新疆阿魏和多伞阿魏化学成分研究", 《中国协和医科大学硕士学位论文 万方数据》 * |
| 王月娥等: "新疆阿魏种子化学成分的系统预实验", 《第六届肉苁蓉暨沙生药用植物学术研讨会论文集》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105878312A (en) * | 2014-09-04 | 2016-08-24 | 中国医学科学院药用植物研究所 | Application of a medicine with anti-influenza virus effect in ferula sinkiangensis seeds |
| CN109223772A (en) * | 2017-07-11 | 2019-01-18 | 中国医学科学院药用植物研究所 | Application of the terpene coumarin kind compound in terms for the treatment of gastric cancer |
| 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 |
| CN111646965A (en) * | 2020-06-03 | 2020-09-11 | 中国医学科学院药用植物研究所 | Compound Sinkiangel E and application thereof in preparation of antitumor drugs |
| 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 |
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| Publication number | Publication date |
|---|---|
| CN105079011B (en) | 2019-07-23 |
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