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Triterpenoid compound, preparation method thereof and application thereof in preparing anticancer drugs

A technology of anticancer drugs and compounds, applied in the directions of steroids, chemical instruments and methods, antitumor drugs, etc., can solve the problems of few types and unsatisfactory anticancer activity, and achieve the inhibition of volume growth and great medicinal value. , non-toxic side effects and drug dependence effect

Active Publication Date: 2019-01-25
HEBEI UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] One of the purposes of the present invention is to provide a triterpenoid compound, to solve the problem that there are few types of triterpenoid compounds with anticancer activity in the prior art, and the problem of unsatisfactory anticancer activity

Method used

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  • Triterpenoid compound, preparation method thereof and application thereof in preparing anticancer drugs
  • Triterpenoid compound, preparation method thereof and application thereof in preparing anticancer drugs
  • Triterpenoid compound, preparation method thereof and application thereof in preparing anticancer drugs

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Effect test

Embodiment 1

[0039] The raw material medicine of the present invention is the fruit body of Ganoderma lucidum produced in Hainan, and the fruit body is chopped and ground for extraction.

[0040] The ethanol extraction method adopted in the preparation method of the present invention can be percolation method, dipping method or reflux extraction method. As a preference, the preparation method of the present invention preferably uses ethanol reflux to extract the raw material drug, and the operation steps are further preferably:

[0041]Use 50-100% ethanol, more preferably 95% ethanol, which is 5-7 times the total weight of the raw material drug, and reflux the raw material drug for 3-4 times, 60 min each time. Below 60°C, the filtrate obtained after ethanol extraction is concentrated into a thick paste of crude extract. The crude extract was subjected to normal phase silica gel chromatography (CHCl 3 / MeOH 9:1-3:1, v / v) after gradient elution, point plate and combine samples to obtain Fra...

Embodiment 2

[0052] The present invention provides a compound 26-O-β-D-glucopyranosyl-Ganodecalone A (Ganodecalone A has poor water solubility), which has good anticancer activity and excellent solubility, and is more suitable for preparing water-soluble anticancer drugs. Its structure is as follows:

[0053]

[0054] Its synthesis method is as follows:

[0055]

[0056] (a) TMSOTf,CH 2 Cl 2 ,-30℃, 89%; (b)CH 3 ONa,CH 3 OH:CH 2 Cl 2 =1:1,95%.

[0057] Under argon protection, compound 1, Ganodecalone A (91 mg, 0.20 mmol) and 2,3,4,6-tetra-acetyl-α-D-glucopyranose trichloroimidate donor 2 (280 mg , 0.26mmol, 1.30equiv.) dissolved in 4mL of anhydrous CH 2 Cl 2 to which was added the dry Molecular sieves (300mg), stirred at -30°C for 30min, added trifluoromethylsilyl trifluoromethanesulfonate (TMSOTf) (7μL, 0.04mmol, 0.2equiv.), stirred at -30°C for 4h, TLC showed that the reaction was complete, Triethylamine quenched the reaction, filtered, concentrated, and flash column chro...

Embodiment 3

[0061] Growth inhibitory activity of compounds Ganodecalone A and 26-O-β-D-glucopyranosyl-Ganodecalone A on tumor cells in vitro.

[0062] The detection method is as follows:

[0063] (1) Cell plating

[0064] The cells were subcultured, and when the cell fusion rate reached about 80%, the old medium was discarded and washed with phosphate buffered saline (PBS, pH7.4) to remove residues, and then 1 mL of 0.5‰ (w / v) trypsin was added to decompose the cells. Digestion, when about 80% of the cells become round, add serum-containing medium to stop digestion, blow the wall of the suction bottle with a pipette gun, blow off the adherent cells as much as possible, add the cell suspension to the centrifuge tube and place it in the centrifuge , centrifuged at 1000rpm for 5min, discarded the supernatant, resuspended the cells with fresh medium, blown and sucked with a pipette gun to disperse the cells as much as possible, counted, and diluted the cell suspension to 5×104 cells / mL. Add...

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Abstract

The invention provides a triterpenoid compound, a preparation method thereof and application thereof in preparing the anticancer drugs. The triterpenoid compound has a structure represented by the formula (I), R is one of COCH3, COCH2CH3, COAr, One of CH3, CH2CH3, CH2Ar, gamma-D-glucose and gamma-D-galactose, and Ar is a benzene ring. The triterpenoids compound has inhibitory activity against human tumor cells in vitro, the inhibitory effects on tumor cells of the human lung cancer, breast cancer, gastric cancer and the like are more obvious, and the IC50 is lower. The inhibitory effect of thecompound on the tumor cells has a certain broad spectrum in mammals. In addition, the compound has almost no inhibitory activity against 293T of normal human human renal epithelial cells, and it is proved that the compound is less toxic to normal cells and has great medicinal value.

Description

technical field [0001] The present invention relates to a triterpenoid compound, in particular to a triterpenoid compound and its preparation method and application in the preparation of anticancer drugs. Background technique [0002] Malignant tumor, commonly known as cancer, refers to a mass that can infect and spread due to abnormal proliferation of local tissue cells under the action of various tumorigenic factors. Malignant tumors can destroy the structure and function of tissues and organs, cause necrosis, hemorrhage and infection, and are diseases that seriously threaten human health and social development. With the development of my country's economy and the improvement of people's material and cultural living standards, people's lifestyles have undergone tremendous changes. At the same time, problems such as air and environmental pollution in my country have become increasingly prominent, and the population is gradually aging. These have led to cancer in China. incr...

Claims

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Application Information

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IPC IPC(8): C07J17/00C07J9/00A61P35/00
CPCA61P35/00C07J9/00C07J17/005Y02P20/55
Inventor 罗都强赵友兴周丽曼罗应泽宋小妹陈朋伟孔凡栋马青云黄圣卓谢晴宜
Owner HEBEI UNIVERSITY
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