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Withanolide compound as well as preparation method and application thereof

A technology for ester compounds and ashwagandha, which is applied in the field of ashwagandha lactones and their preparation, can solve the problems of normal cytotoxicity of ashwagandha lactone compounds without antitumor activity reported in the literature, and achieves significant inhibitory activity, saving Production cost, the effect of novel structure

Active Publication Date: 2021-03-12
ZHEJIANG CHINESE MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] So far, although a series of withanide compounds have been isolated from Solanaceae plants, there are no literature reports on the antitumor activity of withanolide compounds containing seven-membered S, O heterocycles and their effects on normal cells. Toxicity

Method used

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  • Withanolide compound as well as preparation method and application thereof
  • Withanolide compound as well as preparation method and application thereof
  • Withanolide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1: the preparation of formula (Ia) compound

[0066] (1) Extraction: Dragon Ball medicinal material (dried whole herb of Dragon Ball) is ground into coarse powder. Take 4 kg of coarse powder of Dragon Ball medicinal material, add appropriate amount of 95% ethanol to cold soak for 24 hours, then extract by percolation, and collect percolation liquid. The volume of the total solvent extracted is equivalent to 20 times of the quality of the medicinal material (a total of 80 L of 95% ethanol is used).

[0067] (2) Extraction: Concentrate the percolation liquid obtained in step (1) under reduced pressure until it has no alcohol smell, add water to suspend the obtained extract to about 1.6L, extract with 1.6L of ethyl acetate, extract 4 times, and combine the extracts , to obtain the Dragon Ball ethyl acetate extract. The solvent was recovered under reduced pressure and concentrated to obtain 116.15 g of dragon pearl ethyl acetate extract.

[0068] (3) Normal-ph...

Embodiment 2

[0070] Embodiment 2: the structural identification of the formula (Ia) compound that embodiment 1 makes:

[0071] Take about 7.8 mg of the compound, and use CDCl 3 dissolve, test its 1 H NMR spectrum, 13 C NMR spectrum, 2D NMR spectrum; Take an appropriate amount of compound to test its HR-MS spectrum, IR spectrum, and test its specific rotation.

[0072] figure 2 It is the proton nuclear magnetic resonance spectrum of the compound of formula (Ia) structure of the present invention.

[0073] image 3 It is the carbon nuclear magnetic resonance spectrum of the compound of the formula (Ia) structure of the present invention.

[0074] Figure 4 is the DEPT spectrum of the compound of formula (Ia) structure of the present invention.

[0075] Figure 5 Is the compound of formula (Ia) structure of the present invention 1 H- 1 H CSOY spectrum.

[0076] Figure 6 is the HSQC spectrum of the compound of formula (Ia) structure of the present invention.

[0077] Figure 7 ...

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Abstract

The invention discloses a withanolide compound as well as a preparation method and application thereof. The structure of the withanolide compound is shown as a formula (I) or (Ia), and the withanolidecompound has a good effect of inhibiting proliferation of human-derived triple-negative breast cancer cells in vitro, has no cytotoxicity to normal human mammary epithelial cells, and has good development and application prospects. The invention also provides a preparation method of the withanolide compound, and the preparation method is simple to operate and low in production cost.

Description

technical field [0001] The invention relates to the technical field of natural medicinal chemistry, in particular to a withanolalide compound and its preparation method and application. Background technique [0002] According to the 2018 global cancer statistics (Global cancer statistics 2018) released by WHO, breast cancer has the highest incidence rate of female cancer worldwide, and the incidence rate is second only to lung cancer. According to the latest statistics from the Hejie academician team, breast cancer is the cancer with the highest incidence rate among Chinese women. Triple-negative breast cancer (Triple-negative breast cancer, hereinafter referred to as TNBC) accounts for about 12% to 17% of breast cancer. Significant rejuvenation trend. [0003] Currently, there is no molecularly targeted chemotherapy drug for TNBC. After conventional chemotherapy, the recurrence rate of TNBC is very high. It is of great significance to screen high-efficiency, low-toxicit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61P35/00A61K31/585
CPCA61P35/00C07J71/0089
Inventor 杨波赵华军寿泮婷魏莹莹
Owner ZHEJIANG CHINESE MEDICAL UNIVERSITY