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Carbon-drop guaiane sesquiterpene lactone compound and preparation method thereof

A technology of ester compound and guaiacol, applied in the field of medicine, can solve the problems of increasing the cytotoxicity of macrophages and the like

Active Publication Date: 2019-05-17
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When interferon or the second signal acts alone, macrophages are induced to synthesize low amounts of NO and in many cases, there is no direct cytotoxic effect, but interferon and the second signal can significantly increase the production of NO and increase Cytotoxicity of macrophages

Method used

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  • Carbon-drop guaiane sesquiterpene lactone compound and preparation method thereof
  • Carbon-drop guaiane sesquiterpene lactone compound and preparation method thereof
  • Carbon-drop guaiane sesquiterpene lactone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] a. Take 5 kg of the whole Achillea sylvestris, crush it and extract it with 50L of 50% ethanol-water solution at room temperature, then evaporate the solvent under reduced pressure to obtain a crude extract of the Achills sylvestris;

[0039] b. Disperse the crude extract obtained in step a with water, add petroleum ether, ethyl acetate, and n-butanol to extract 3 times in sequence, combine the ethyl acetate layers and evaporate to dryness under reduced pressure to obtain the ethyl acetate layer extract extract;

[0040] c. Separate the extract from the ethyl acetate layer obtained in step b with a normal phase silica gel column, and perform gradient elution with petroleum ether-ethyl acetate in a volume ratio of 50:1-0:1, and the fractions are passed through a thin silica gel layer Chromatographic analysis, the same fractions were combined to obtain 9 components F1-F9; the component F4 was separated by Sephadex LH-20 gel column and eluted with chloroform-methanol with a volu...

Embodiment 2

[0042] a. Take 5 kg of Achillea sylvestris whole plant, crush it and extract with 40L of 95% ethanol-water solution at a temperature of 80°C under reflux, and evaporate the solvent under reduced pressure to obtain a crude extract of Achills sylvestris whole plant;

[0043] b. Disperse the crude extract obtained in step a with water, sequentially add n-hexane, dichloromethane and n-butanol for extraction 4 times, combine the dichloromethane layers, and evaporate to dryness under reduced pressure to obtain a dichloromethane extract extract;

[0044] c. Separate the dichloromethane extract obtained in step b with a normal phase silica gel column, perform gradient elution with n-hexane-acetone with a volume ratio of 100:1-0:1, and analyze the fraction by silica gel thin layer chromatography , The same fractions were combined to obtain 9 components F1-F9; the component F4 was separated by Sephadex LH-20 gel column, and eluted with chloroform-methanol with a volume ratio of 1:1 to obtain ...

Embodiment 3

[0046] a. Take 5kg of the whole Chiba Achillea, pulverize and extract with 40L of absolute ethanol at room temperature, and evaporate the solvent under reduced pressure to obtain a crude extract of the whole Chiba Achillea;

[0047] b. Disperse the crude extract obtained in step a with water, sequentially add cyclohexane, ethyl acetate, and n-butanol for extraction 5 times, combine the ethyl acetate layers and evaporate to dryness under reduced pressure to obtain ethyl acetate extract extract;

[0048] c. Separate the ethyl acetate extract obtained in step b with a normal phase silica gel column, and perform gradient elution with cyclohexane-acetone with a volume ratio of 50:1-0:1, and the fractions are subjected to silica gel thin-layer chromatography Analyze and combine the same fractions to obtain 9 components F1-F9; separate component F4 through an ODS reverse phase column, eluting with a methanol-water solution gradient with a concentration of 40%-100%, and collect 60% methanol...

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Abstract

The invention relates to a carbon-drop guaiane sesquiterpene lactone compound and a preparation method thereof. The carbon-drop guaiane sesquiterpene lactone compound is characterized in that three new carbon-drop guaiane sesquiterpene lactone monomer compounds are obtained from the whole herb of achillea millefolium L. through adopting a thin layer chromatography method and an analytical type high performance liquid chromatography method for detection and analysis, using organic solvent for extraction, and then performing separation by four to five methods of a solvent extraction method, a normal phase slica column chromatography method, a pinhole resin column chromatography method, a sephadex LH-20 gel column chromatography method and a semi-preparation high performance liquid chromatography method; and the three monomer compounds are determined as the new carbon-drop guaiane sesquiterpene lactone compounds through methods of a high resolution mass spectrum, a nuclear magnetic resonance spectrum and the like, and are subjected to structure identification. In addition, anti-inflammatory activity measurement is carried out; and it is indicated, by a result, that the three new carbon-drop guaiane sesquiterpene lactone compounds have different degrees of anti-inflammatory activity, and can be used for preparing anti-inflammatory medicines.

Description

Technical field [0001] The present invention relates to the technical field of medicine, in particular to a carbon-reducing guaiacol sesquiterpene lactone compound and a preparation method thereof. Background technique [0002] Terpenoids are an important part of natural organic compounds. They are made up of several isoamylenes connected end to end. Among them, three isoamylenes are sesquiterpenes. The sesquiterpene lactone is a lactone compound whose basic skeleton is composed of three isoamylene units. Guaianes-type sesquiterpene lactones are a very important class of sesquiterpenes that exist in nature. Its molecular skeleton is composed of a typical [5,7] complex ring structure and has a variety of biological activities, including anti- Inflammation, antibacterial, anti-tumor, etc. At present, there are hundreds of guaianese-type sesquiterpenes that have been isolated and identified in nature. The reason for their rich structure is that they often have various substituents...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/34A61P29/00
Inventor 阿吉艾克拜尔·艾萨李红亮李俊
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI