O-bis-tetrahydrofuran type annonaceous acetogenins compound having antitumor activity, preparation method, and application thereof

A technology of tetrahydrofuran type and annua lactone, which is applied in the directions of antitumor drugs, organic active ingredients, and medical preparations containing active ingredients, etc., can solve the problems of poor patient tolerance, limited antitumor activity, and large toxic and side effects. , to achieve the effect of strong anti-tumor activity, low toxicity and high purity

Inactive Publication Date: 2017-05-31
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 therap

Method used

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  • O-bis-tetrahydrofuran type annonaceous acetogenins compound having antitumor activity, preparation method, and application thereof
  • O-bis-tetrahydrofuran type annonaceous acetogenins compound having antitumor activity, preparation method, and application thereof
  • O-bis-tetrahydrofuran type annonaceous acetogenins compound having antitumor activity, preparation method, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 Preparation of o-bistetrahydrofuran type annona lactone compound (Annona syringa)

[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. F10 (23.7 g) was separated by medium-pressure column chromatography on reverse-phase silica gel, and was eluted with methanol-water (20:1-1:0) gradient, and should be divided into 8 parts (F13-F21) ). The precipitate of F19 was recrystallized from ethyl acetate-methanol to obtain the compound Annona sativa (1). The purity was 99.1% by HPLC detection.

[0...

Embodiment 2

[0040] Example 2. Acute toxicity test of o-bistetrahydrofuran type annona lactone compound (Annona sativa).

[0041] Calculate the half lethal dose LD of mice according to Bliss method 50 value, and the results are as follows:

[0042] Table 2. Acute toxicity test data

[0043]

[0044] LD obtained from experiment 50 The value shows that the acute toxicity of citrus annus is low, and among the three routes of administration, the toxicity of oral administration is the least, and the intravenous injection presents a more sensitive dose-effect (death) relationship due to the rapid arrival of the drug into various organs.

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- For the tumor experiment, 6 concentrations of the custard apple 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. From the experimental results in Table 3, it can be seen that the anti-tumor effect of the custard apple on 3 strains of human tumor cells is different, and the anti-tumor experimental data in vitro shows that the cisplatin cisplatin provided by the present invention is stronger than the positive drug cisplatin. cell selective inhibitory activity.

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

[0048]

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Abstract

The invention discloses an o-bis-tetrahydrofuran type annonaceous acetogenins compound having antitumor activity. Through systemically deep researching on chemical ingredients of seeds of annona squamosa, wave spectrum and mass spectrum data analysis proves that the novel o-bis-tetrahydrofuran type annonaceous acetogenins compound can be separated from the seeds of annona squamosa. In-vivo and in-vitro antitumor activity researching proves that the o-bis-tetrahydrofuran type annonaceous acetogenins has strong antitumor activity on various tumor cells, such as lung cancer cells, breast cancer cells, liver cancer cells, etc., and also has significant inhibition activity on mouse transplanted liver tumor HepG2 and mouse sarcoma S180 solid tumor. Toxicity tests prove that the o-bis-tetrahydrofuran type annonaceous acetogenins compound has low toxicity and is an excellent antitumor compound.

Description

technical field [0001] The invention relates to a compound with antitumor activity, in particular to a new o-bistetrahydrofuran type anemone lactone compound with antitumor activity and its use 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, po...

Claims

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Application Information

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IPC IPC(8): C07D307/58A61K31/365A61P35/00
CPCC07D307/58
Inventor 李祥马程遥陈建伟
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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