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Epoxy type annonaceous acetogenin compound with antitumor activity and preparation method and application thereof

An annua lactone and anti-tumor activity technology, applied in the field of medicine, can solve the problems of large toxic and side effects, high price, limited anti-tumor activity, etc., and achieve the effect of strong anti-tumor activity and low toxicity

Inactive Publication Date: 2017-03-29
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In many countries including China, especially moderately developed countries, the death caused by malignant tumors accounts for the first or second place among all causes of death, and the incidence rate is still on the rise worldwide. Among the four major therapies of chemotherapy, chemotherapy and biological therapy, chemotherapy is still the main treatment method, but as we all know, the existing chemotherapy drugs have limited anti-tumor activity, high toxicity and side effects, poor patient tolerance, and high prices

Method used

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  • Epoxy type annonaceous acetogenin compound with antitumor activity and preparation method and application thereof
  • Epoxy type annonaceous acetogenin compound with antitumor activity and preparation method and application thereof
  • Epoxy type annonaceous acetogenin compound with antitumor activity and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of embodiment 1 epoxy-type annona lactone compound (diprotexinine B)

[0035] Take 10kg of dried custard apple seeds, percolate with chloroform after crushing, reclaim and combine the percolation liquid, filter, and reclaim the filtrate under reduced pressure to obtain 1 kg of concentrated solution, the concentrated solution is separated by column chromatography with normal phase silica gel, and separated by petroleum ether-ethyl acetate -Methanol gradient elution, a total of 500 fractions were collected and combined into twelve fractions (F1-F12) according to the thin-layer chromatography. F3 (178.8 g) was separated by normal phase silica gel column chromatography and eluted with petroleum ether-ethyl acetate (20:1-0:1) gradient to obtain diproticinine B (1). The purity was 98.3% by HPLC detection.

[0036] Structural analysis: white powder, molecular formula: C 35 h 60 o 4 ; Melting point: 60-62℃; Optical rotation: [α] 25 D +13.0(c 0.1,EtOH); UV:...

Embodiment 2

[0039] Example 2. Acute toxicity test of epoxy type annona lactone compound (diprotecinine B).

[0040] Calculate the half lethal dose LD of mice according to Bliss method 50 value, and the results are as follows:

[0041] Table 2. Acute toxicity test data

[0042]

[0043]

[0044] LD obtained from experiment 50 The value shows that the acute toxicity of diproticinine B is low. Among the three routes of administration, the toxicity of oral administration is the least. Because the drug reaches the various organs quickly by intravenous injection, it presents a more sensitive dose-effect (death) relationship. .

Embodiment 3

[0045] Example 3: Inhibitory effect on human tumor cells in vitro.

[0046] Drug-resistant tumor strains: human breast cancer (MCF-7 / ADR), human liver cancer (SMMC-7721 / T), human lung cancer (A549 / T) three tumor strains, using thiazolium blue reduction method (MTT) for in vitro anti- In the tumor experiment, 6 concentrations of diproticinine B prepared in Example 1 were set, cisplatin was used as the positive control group, and dimethyl sulfoxide, the solvent of the sample, was used as the negative control group. As can be seen from the experimental results in Table 3, diproticinin B shows different inhibitory effects on 3 strains of human tumor cells, and the anti-tumor experimental data in vitro shows that diproticinin B provided by the present invention has a higher inhibitory effect than the positive drug cisplatin. Stronger cell selective inhibitory activity.

[0047] Table 3 Inhibitory effect of diproticinine B on 3 strains of drug-resistant tumor cells.

[0048]

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Abstract

The invention discloses an epoxy type annonaceous acetogenin compound with antitumor activity; through systematic deep research on the chemical composition of Annona squamosa seeds, wave spectral and mass spectral data analysis indicates the novel epoxy annonaceous acetogenin compound is isolated from Annona squamosa seeds, in-vivo and in-vitro antitumor activity researches indicate that epoxy type annonaceous acetogenins provided herein show high antitumor activity to various tumor cells, such as lung cancer cells, breast cancer cells, and liver cancer cells and show significant inhibitory activity to the solid tumors of mouse implanted hepatic tumor HepG2 and mouse sarcoma S180, and toxicity experiment researches indicate that the epoxy type annonaceous acetogenin compound provided herein has low toxicity and is a good antitumor compound.

Description

technical field [0001] The invention relates to a compound with anti-tumor activity, in particular to a novel epoxy type annona lactone compound with anti-tumor activity and its application in preventing and treating tumor diseases, belonging to the technical field of medicine. Background technique [0002] Malignant tumors are frequent and common diseases that seriously endanger human health and life. As early as 2000-3000 years ago, there were records about tumors in Egypt and my country. In many countries including China, especially moderately developed countries, the death caused by malignant tumors accounts for the first or second place among all causes of death, and the incidence rate is still on the rise worldwide. Among the four major therapies of chemotherapy, chemotherapy, and biological therapy, chemotherapy is still the main treatment method, but as we all know, the existing chemotherapy drugs have limited anti-tumor activity, large toxic and side effects, poor p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/14A61K31/365A61P35/00
CPCA61K36/185C07D407/14
Inventor 李祥马程遥陈建伟
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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