Preparation method of monoterpenoid indole alkaloid compound and application thereof

A technology of indole alkaloids and compounds, which can be used in drug combination, organic chemistry, antineoplastic drugs, etc., and can solve the problem of rare rose trees

Active Publication Date: 2017-06-13
HAINAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are few reports on the chemical constituents and pharmacological activity of rose tree, mainly focusing on finding alkaloid compounds with anti-tumor activity therefrom [Zhang B.J, Yan J.M, Wu Z.K, etal.Alkaloids from Ochrosia borbonica .Helv.Chim.Acta 2013,96:2288-2298.;Svoboda G,Poore G,Montfrot M.L.Alkal

Method used

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  • Preparation method of monoterpenoid indole alkaloid compound and application thereof
  • Preparation method of monoterpenoid indole alkaloid compound and application thereof
  • Preparation method of monoterpenoid indole alkaloid compound and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Embodiment one: the preparation method of compound ochroelline (one)

[0019] 1. After the pulverized rose branches and leaves dried in the shade (28.2kg, Guangdong) were extracted by cold soaking with 3 times the concentration of 90% ethanol solution for 3 times, each extraction was performed for one week, filtered, and the extract was concentrated under reduced pressure to obtain 1286.3g of ethanol extract;

[0020] 2. Add water to the ethanol extract to make a suspension, extract with an equal volume of petroleum ether and an equal volume of ethyl acetate successively, each extracting 3 times, to obtain a petroleum ether extract; the petroleum ether extract is concentrated under reduced pressure, Obtain petroleum ether extract 280.8g;

[0021] 3. Purify the petroleum ether extract by column chromatography: the petroleum ether extract is separated by silica gel column chromatography, and petroleum ether-acetone gradient elution (95:5, 90:10, 80:20, 70:30, 60 :40, 50:...

Embodiment 2

[0026] Embodiment two: the preparation method of compound ochroelline (two)

[0027] 1. After the pulverized rose branches and leaves dried in the shade (9.8kg, Hainan) were extracted by cold soaking with 4 times the amount of methanol for 4 times, each time for 3 days, filtered, the extract was concentrated under reduced pressure to obtain a methanol extract (528.2g).

[0028] 2. Add water to the methanol extract to make a suspension, sequentially extract with equal volumes of petroleum ether and equal volumes of ethyl acetate, and extract 4 times each to obtain petroleum ether extracts; concentrate the petroleum ether extracts under reduced pressure to obtain petroleum ether extracts. ether extract (102.6 g);

[0029] 3. Separation and purification of the petroleum ether extract by column chromatography: segment the petroleum ether extract by silica gel column chromatography, and gradient elution of petroleum ether-acetone (95:5, 90:10, 80:20, 70:30, 60:40, 50:50), collect ...

Embodiment 3

[0031] Example 3: Research on the antitumor activity of the compound ochroelline

[0032] 1. Experimental method: Four common tumor cell lines K562, SPCA-1, SGC-7901 and BEL-7402 were respectively used in RPMI-1640 medium containing 10% calf serum at 37°C and 5% CO 2 cultured in an incubator. The MTT method was used to carry out the cell proliferation inhibition test. The main operation was: take the tumor cell line in the logarithmic growth phase, digest it with 0.25% trypsin, and prepare 5×10 RPMI-1640 culture solution with 10% newborn calf serum 4 cells / mL of cell suspension, inoculated in 96-well plate, inoculated 180 μL per well. at 37°C, 5% CO 2 Cultivate for 8-10 hours under saturated humidity conditions, and when they adhere to the wall, add a sample solution prepared with PBS to each well so that the final concentrations of the samples are 0.1, 1, and 10 μg / mL, respectively. For each concentration, 3 wells were paralleled, and after 44 hours of continuous culture, ...

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Abstract

The invention discloses a preparation method of a monoterpenoid indole alkaloid compound with a novel chemical structure from ochrosia borbonica and a medical application of the compound in preparation of a targeted anti-tumor drug by employing protein tyrosine kinase as a target. The compound is a novel monoterpenoid indole alkaloid compound. The compound has significant anti-tumor activity, has protein tyrosine kinase-inhibition activity equivalent to a positive control drug, and has the prospect of being developed into the targeted anti-tumor drug by employing the protein tyrosine kinase as the target.

Description

technical field [0001] The invention belongs to the field of natural medicine preparation, and relates to an alkaloid compound with a novel structure derived from rose tree, in particular to a preparation method of a monoterpene indole alkaloid compound and its application in the preparation of targeted antitumor drugs Applications. Background technique [0002] Malignant tumor is a frequently-occurring disease with a high mortality rate. It is currently seriously threatening human life and health, and is gradually surpassing cardiovascular disease to become the number one killer threatening human life and health. With the continuous elucidation of the mechanism of tumorigenesis and the discovery of anti-tumor targets, the discovery of multi-target anti-tumor drugs has become an important direction for the development of new anti-tumor drugs. Compared with single-target drugs and multiple single-target drug combinations, multi-target drugs can effectively avoid drug interac...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61P35/00
CPCC07D471/14
Inventor 付艳辉刘艳萍陈阿红柳庆龙马延蕾蒋芝华唐进英
Owner HAINAN NORMAL UNIVERSITY
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