CN101774959A - Preparation method and application of bromine-containing indole alkaloid - Google Patents
Preparation method and application of bromine-containing indole alkaloid Download PDFInfo
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- CN101774959A CN101774959A CN200910256555A CN200910256555A CN101774959A CN 101774959 A CN101774959 A CN 101774959A CN 200910256555 A CN200910256555 A CN 200910256555A CN 200910256555 A CN200910256555 A CN 200910256555A CN 101774959 A CN101774959 A CN 101774959A
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- bromine
- indole alkaloid
- containing indole
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Abstract
The invention relates to a preparation method and application of bromine-containing indole alkaloid. The preparation method comprises the following steps of: washing nodular cartilage laurencia by using water, pulverizing, leaching by using an ethanol water solution, then leaching by using the mixed liquid of chloroform and methanol, mixing the two obtained leaching solutions, decompressing and concentrating to obtain a crude extract; and diluting the crude extract by using the water, then extracting by using ethyl acetate, obtaining an ethyl acetate phase extract after decompressing and concentrating the obtained extraction liquid, and carrying out silicagel column decompressing chromatography to obtain the bromine-containing indole alkaloid by repeated silicagel column normal-pressure chromatography and Sephadex LH-20 gel column chromatography. The bromine-containing indole alkaloid prepared by the invention has stronger suppression activity to chronic myelogenous primary leukaemia cells K562, human stomach cancer cells SGC-7901 and human liver cancer cells SMMC-7721 and can be used as an anti-tumor medicine. Raw materials are easy to obtain, and the application prospect is extensive.
Description
Technical field
The present invention relates to a kind of preparation method and application with bromine-containing indole alkaloid compound of anti-tumor activity.
Background technology
Warty cartilage concave crown algae [Chondrophycus papillous (C.Agardh) Garbary et Harper] belongs to rhodophyta (Rhodophyta), Rhodophyceae (Rhodophyceae), Ceramiale (Ceramiales), Rhodomelaceae (Rhodomelaceae), the subgenus in the Laurencia (Laurencia).In recent years chemistry and pharmacological research show, contain the compound of abundant structures novelty in the concave crown algae, and these compounds have the unique biological activity, and be antiviral as antitumor, anti-inflammatory or antimycotic etc.Bromine-containing indole alkaloid is exactly wherein a kind of, and its research will be played significant role at medicine and association area.
Summary of the invention
The object of the present invention is to provide a kind of preparation method and its application in the preparation antitumor drug of bromine-containing indole alkaloid, it can remedy the demand of prior art.
A kind of preparation method of bromine-containing indole alkaloid is characterized in that warty cartilage concave crown algae water is cleaned, and pulverizes, and uses the aqueous ethanolic solution lixiviate, uses the mixed solution lixiviate of chloroform and methyl alcohol again, and with two kinds of vat liquors mixing of gained, concentrating under reduced pressure obtains crude extract; With this crude extract dilute with water, use ethyl acetate extraction again, behind gained extraction liquid concentrating under reduced pressure, get ethyl acetate phase medicinal extract, carry out silicagel column decompression chromatography,, obtain the bromine-containing indole alkaloid compound through silicagel column normal pressure chromatography and Sephadex LH-20 gel filtration chromatography repeatedly.
The application of above-mentioned bromine-containing indole alkaloid in the preparation antitumor drug.
The bromine-containing indole alkaloid compound of the present invention's preparation has stronger inhibition activity to the former leukemia cell K562 of chronic marrow, gastric carcinoma cells SGC-7901 and human liver cancer cell SMMC-7721, can be used as antitumor drug.Raw material is easy to get, and has a extensive future.
Embodiment
When preparing compound of the present invention,
(1) the warty cartilage concave crown algae [Chondrophycus papillous (C.Agardh)] that will pick up from plum mountain and sea territory, Sanya, Hainan is cleaned with tap water, remove silt, after this warty cartilage concave crown algae sample pulverizing, with the aqueous ethanolic solution lixiviate of 95% (percent by volume) 3 times, and then with the mixed solution lixiviate of chloroform and methyl alcohol 3 times.Merge two kinds of vat liquors, concentrating under reduced pressure gets crude extract.After the dilution of this crude extract usefulness 500mL water, use equal volume of ethyl acetate again 6 times, gained extraction liquid concentrating under reduced pressure is obtained ethyl acetate phase medicinal extract, and the volume ratio of chloroform and methyl alcohol is 1 in the mixed solution of described chloroform and methyl alcohol: 1-2, present embodiment are 1: 1.Sealing is stored in 4 ℃ of refrigerators standby.
(2) above-mentioned ethyl acetate phase medicinal extract (50.5g) process decompression silica gel column chromatography (VLC), and the petroleum ether-ethyl acetate gradient (100: 0,90: 10,80: 20,60: 40,50: 50,30: 70,0: 100) wash-out, it is divided into 7 components (Fr.1～Fr.7) according to the polarity size.Fr.2 (5.0g, petroleum ether-ethyl acetate 90: 10) through silica gel column chromatography, use the petroleum ether-ethyl acetate gradient elution, (Fr.2-1～Fr.2-4), Fr.2-2 is through silica gel column chromatography and Sephadex LH-20 gel filtration chromatography get 2 repeatedly to obtain 4 components, 3,5,6-tetrabromo-1-skatole (25.0mg) and 2,3,5,6-tetrabromo indoles (90.0mg).The structural formula of compound that makes is:
R is CH in the formula
3The time, this compound is 2,3,5,6-tetrabromo-1-skatole, and when R was H, this compound was 2,3,5,6-tetrabromo indoles.
The anti tumor activity in vitro shaker test and the result thereof of the above-mentioned bromine-containing indole alkaloid that makes
(1) anti-tumor activity test
Adopt the micro-enzyme reaction colorimetry of tetramethyl-azo azoles salt (MTT), the anti tumor activity in vitro of the former leukemia cell K562 of chronic marrow, gastric carcinoma cells SGC-7901 and human liver cancer cell SMMC-7721 cell strain is tested.
(2) activity test method
The experiment establish negative control group (water), DMSO solvent control group, positive controls (ametycin) and 8 different concns (0.2,0.4,0.8,1.6,3.2,6.4,12.8,25.6) the testing sample group, each concentration establish 3 parallel.Choose the logarithmic phase cell, make single-cell suspension liquid with the RPMI1640 perfect medium, with the blood counting chamber counting, inoculate 90 μ L in the flat Tissue Culture Plate in 96 holes by 50000/mL, placing volume fraction is 5%CO
2, humidity more than 90%, cultivate in 37 ℃ of incubators.Take out behind the 24h, add the 1mg testing sample, take out after continuing to cultivate 72h, place microscopically to observe every porocyte form, record cellular form changing conditions.Every then hole adds the MTT solution 50 μ L of 5mg/mL, behind 37 ℃ of reaction 4h, inhales and abandons supernatant liquor, add 100 μ L DMSO to each hole again, fully dissolving places Tissue Culture Plate on the MK3 microplate reader, with the absorbancy (A) in each hole of 570nm wavelength measurement, by the following formula long inhibiting rate of seeking survival:
The relation of concentration and inhibiting rate per sample, obtaining inhibiting rate is the half-inhibition concentration (IC of 50% o'clock sample
50), the active result of sample is promptly with IC
50Expression.
(3) active testing result
Test-results shows that the bromine-containing indole alkaloid of the present invention's preparation can effectively suppress the growth of the former leukemia cell K562 of chronic marrow, gastric carcinoma cells SGC-7901 and human liver cancer cell SMMC-7721.Bromine-containing indole alkaloid is to suppressing the IC of tumor cell line
50Value (μ g/mL) sees Table 1.
Anti tumor activity in vitro (the IC of two kinds of compounds of table 1 the present invention preparation
50, μ g/mL)
Annotate: Mitomycin C, positive contrast medicine.
Claims (2)
1. the preparation method of a bromine-containing indole alkaloid is characterized in that warty cartilage concave crown algae water is cleaned, and pulverizes, and uses the aqueous ethanolic solution lixiviate, uses the mixed solution lixiviate of chloroform and methyl alcohol again, and with two kinds of vat liquors mixing of gained, concentrating under reduced pressure obtains crude extract; With this crude extract dilute with water, use ethyl acetate extraction again, behind gained extraction liquid concentrating under reduced pressure, get ethyl acetate phase medicinal extract, carry out silicagel column decompression chromatography,, obtain bromine-containing indole alkaloid through silicagel column normal pressure chromatography and SephadexLH-20 gel filtration chromatography repeatedly.
2. the application of the described bromine-containing indole alkaloid of claim 1 in the preparation antitumor drug.
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| Application Number | Priority Date | Filing Date | Title |
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| CN200910256555A CN101774959A (en) | 2009-12-24 | 2009-12-24 | Preparation method and application of bromine-containing indole alkaloid |
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| CN200910256555A CN101774959A (en) | 2009-12-24 | 2009-12-24 | Preparation method and application of bromine-containing indole alkaloid |
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| CN101774959A true CN101774959A (en) | 2010-07-14 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113533786A (en) * | 2021-01-24 | 2021-10-22 | 大理大学 | Method for researching anti-pollution action mechanism of diindole alkaloid on Nitzschia closterium based on electron microscopic imaging technology |
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2009
- 2009-12-24 CN CN200910256555A patent/CN101774959A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113533786A (en) * | 2021-01-24 | 2021-10-22 | 大理大学 | Method for researching anti-pollution action mechanism of diindole alkaloid on Nitzschia closterium based on electron microscopic imaging technology |
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Application publication date: 20100714 |