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Euphorbia lathyris large ring diterpenoid compound and application thereof

A technology of diterpenoids and compounds, applied in the field of macrocyclic diterpenoids of capers

Inactive Publication Date: 2013-05-22
CHENGDU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There is no report on the macrocyclic diterpenoids as shown in the structural formula (I) extracted and isolated from capers

Method used

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  • Euphorbia lathyris large ring diterpenoid compound and application thereof
  • Euphorbia lathyris large ring diterpenoid compound and application thereof
  • Euphorbia lathyris large ring diterpenoid compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take 2000g of caperia sativa fruit, grind it, and extract it twice with 5000 ml of ethanol at 80°C under reflux, each time for 3 hours, to obtain an ethanol extract; recover ethanol from the ethanol extract under reduced pressure to obtain an ethanol extract. Disperse the ethanol extract in 3000ml of water, extract twice with 3000ml of petroleum ether to obtain a petroleum ether extract, concentrate the petroleum ether extract under reduced pressure, recover petroleum ether, and obtain a petroleum ether extract. The petroleum ether extract was chromatographed on a silica gel column and eluted with a gradient of petroleum ether-acetone in different proportions. Crystals were precipitated in the eluent with a ratio of petroleum ether:acetone of 5:1, and a large number of crystals were precipitated after concentration. According to the NMR test, the crystal is the compound shown in the above formula (II), and the molecular formula is C 38 h 42 o 9 , colorless, its NMR da...

Embodiment 2

[0034] 1000 mg of the compound prepared in Example 1 was dissolved in 100 ml of methanol solution saturated with sodium hydroxide, and refluxed in a water bath at 60° C. for 12 hours. Concentrate under reduced pressure to remove methanol, add ethyl acetate to dissolve, then wash away water-soluble substances such as sodium hydroxide with water to obtain ethyl acetate liquid, concentrate the ethyl acetate liquid to 10ml, leave it for a period of time, until crystals are precipitated, and filter to obtain crystals , the crystal was tested by proton nuclear magnetic spectrum, showing that there were no acetate groups and benzoate groups, and then tested by mass spectrometry, its molecular formula was C 20 h 30 o 5 , the structural formula is shown in formula (Ⅲ).

Embodiment 3

[0036] Anticancer activity test of the compound of embodiment 1

[0037] The inhibitory effect of compounds on cells was determined by XTT method.

[0038] Prepare XTT into a 1g / L solution with serum-free RPMI-1640 medium, and filter to sterilize with a 0.22 μm filter membrane. Preparation of PMS: PBS (containing 8.0 grams of sodium chloride per liter, 0.20 grams of potassium chloride, 1.44 grams of sodium dihydrogen phosphate, 0.24 grams of potassium dihydrogen phosphate, pH 7.4) was used to prepare a 5 mmol / L PMS stock solution, 0.22 Sterilize with a μm filter membrane and store in the dark at 4°C. Add 50μL of PMS to every 10mL of newly prepared XTT (1g / L), and mix well to get the XTT-PMS use solution, which is ready for immediate use.

[0039] Determination method: take SMMC-7221, L in the logarithmic growth phase 342 , MCc80-3 cells were blown into a single cell suspension, and counted by trypan blue staining (the percentage of viable cells > 95%), and the cells were co...

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PUM

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Abstract

The invention discloses an euphorbia lathyris large ring diterpenoid compound and an application of the euphorbia lathyris large ring diterpenoid compound in preparation of drugs used for treating liver cancer, lung cancer and stomach cancer. The euphorbia lathyris large ring diterpenoid compound is prepared by extracting euphorbia lathyris fruits, and a chromatographic process identifies that the disclosed by the invention is a novel euphorbia lathyris large ring diterpenoid compound. Experiments show that the euphorbia lathyris large ring diterpenoid compound has the effect of strongly inhibiting liver cancer (SMMC-7221), lung adenocarcinoma (L342) and gastric adenocarcinoma (MCc80-3).

Description

technical field [0001] The present invention relates to a macrocyclic diterpenoid compound of capers and its application. Background technique [0002] According to the latest data, the top five cancers in males in my country are lung cancer, gastric cancer, liver cancer, (color) rectal cancer, and esophageal cancer. The top five cancers for women are lung cancer, breast cancer, gastric cancer, (color) rectal cancer, and liver cancer. Lung cancer, gastric cancer, and liver cancer rank among the forefront of tumor incidence. [0003] Euphorbia lathyris is a species of Euphorbia, distributed in more than 10 provinces and cities in my country, and is a traditional Chinese medicinal material. "Compendium of Materia Medica" and other records that the plant has the effects of "dispelling water to reduce swelling, breaking silt and killing insects". The literature reports that the active ingredients in this plant are mainly macrocyclic diterpenoids. The results of pharmacologic...

Claims

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Application Information

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IPC IPC(8): C07C69/78C07C67/48C07C49/743C07C45/61A61K31/235A61K31/122A61P35/00
Inventor 陈封政苟小军郭晓强颜军宋芹何钢刘嵬
Owner CHENGDU UNIV
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