Eremophil dilactone with tumour cell growth inhibiting activity and its use

A technology of lactone and cancer cells, applied in the field of natural medicinal chemistry and pharmacology, can solve the problems that the research of biological activity has not been reported yet

Inactive Publication Date: 2008-08-13
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the chemical constituents and biological activity of Ligularia black purple

Method used

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  • Eremophil dilactone with tumour cell growth inhibiting activity and its use
  • Eremophil dilactone with tumour cell growth inhibiting activity and its use
  • Eremophil dilactone with tumour cell growth inhibiting activity and its use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of Compound 1-A1

[0027] Take 5.0 kg of dry underground part of Ligularia atroviblacea (Franch.) Hand.-Mazz., pulverize into powder, add 50 liters of 95% ethanol to soak. Soak 3 times at room temperature, 7 days each time. The ethanol extracts were combined, and the solvent was recovered under reduced pressure to dryness to obtain 462 grams of extract, dispersed with 3 liters of water, and then extracted with 60-90° petroleum ether, ethyl acetate, and n-butanol in sequence. The ethyl acetate extract was recovered under reduced pressure to obtain 89.0 g of extract. The extract was chromatographed on 800 g of 100-200 mesh silica gel column, and chloroform-methanol (50:0-0:1) gradient eluted. Thin-layer chromatography detection combined the same fractions, and the part of the extract containing compound 1-A1 was purified by preparative thin layer (60-90° petroleum ether-ethyl acetate 4:1) followed by Sephadex LH-20 column chromatography ( elutin...

Embodiment 2

[0029] Example 2: Preparation of compound 1-A2

[0030] With embodiment 1, obtain 89.0 gram ethyl acetate extracts from 5.0 kilograms of drying Heiziwu. The extract was chromatographed on 800 g of 100-200 mesh silica gel column, and chloroform-methanol (50:0-0:1) gradient eluted. Thin-layer chromatography detection merged the same fractions, and the partial extract (4.8 grams) containing compound 1-A2 was subjected to 200-300 mesh silica gel (90 grams) column chromatography, and was mixed with 60-90° petroleum ether-ethyl acetate 8 :1-2:1 gradient elution, followed by preparative TLC (60-90° petroleum ether-ethyl acetate 6:1) purification to finally obtain compound 1-A2 (17 mg).

[0031] Physical and spectral data of compound 1-A2: colorless needles; melting point: 167-169°C; [α] D 20 : +41.0°(chloroform; c0.25); UVλ max (Chloroform) nm: 219; IR v max KBr (cm -1 ): 1777, 1741, 1679; Electrospray mass spectrometry ESI-MS (m / z): 291 [M+H] + ; High-resolution electrospr...

Embodiment 3

[0032] Example 3: Preparation of Compound 1-B1

[0033] With embodiment 1, obtain 89.0 gram ethyl acetate extracts from 5.0 kilograms of drying Heiziwu. The extract was chromatographed on 800 g of 100-200 mesh silica gel column, and chloroform-methanol (50:0-0:1) gradient eluted. The same fractions were combined by thin-layer chromatography detection, and the part of the extract containing compound 1-B1 was purified by preparative thin layer (60-90° petroleum ether-ethyl acetate 4:1) followed by Sephadex LH-20 column chromatography ( Methanol elution) to finally obtain compound 1-B1 (23mg).

[0034] Colorless needle crystals; melting point: 172-174°C; [α] D 20 : -62.0° (acetone; c0.20); UVλ max (Acetone) nm: 222; IRv max KBr (cm -1 ): 3325, 1774, 1745, 1671, 1428; Electrospray mass spectrometry ESI-MS (m / z): 277 [M+H] + ; High-resolution electrospray mass spectrometry HR-ESI-MS (m / z): 277.1050 (calculated value [C 15 h 16 o 5 +H] + 277.1031); 13 C and 1 The H N...

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Abstract

This invention relates to Ailinofen bi lactone and its medical used salt or solvate. This invention also relates its preparation method and its medical combination and medical application. The compound in this invention can in vitro prevent six kinds of human body tumor cells activity as human original medullary cell leukemia cell(HL-60), nasopharyngeal carcinoma cell(CNE), oral epithelium cancer cell(KB), human lung cancer cell(549), human hepatic carcinoma cell(BEL-7404) and human uterus neck cancer cell(Hela). It can be developed as anti tumor medicine application.

Description

technical field [0001] The invention belongs to the technical field of natural medicinal chemistry and pharmacology. Specifically, the present invention relates to the preparation of a class of erimorphine dilactone natural products and the effects of these natural products on six kinds of human tumor cell lines such as human myeloid leukemia cells (HL-60), nasopharyngeal carcinoma cells ( CNE), oral epithelial cancer cells (KB), human lung cancer cells (A549), human liver cancer cells (BEL-7404) and human cervical cancer cells (Hela) tumor cell growth inhibitory activity screening. These natural products have been found to have a certain activity of inhibiting the growth of tumor cells, and can be expected to be used as antitumor drugs. technical background [0002] At present, due to environmental pollution and other problems brought about by industrial development, the quality of human living environment is continuously declining, and the incidence and mortality of tumor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/06A61K31/365A61P35/00
Inventor 赵昱黄可新王晓雨施树云孙莲莉王利霞杨雷香
Owner WENZHOU MEDICAL UNIV
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