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Carbon-reducing guaiacane-type sesquiterpene lactone compound and preparation method thereof

An ester compound, guaiacane technology, applied in the field of medicine, can solve the problem of increasing the cytotoxicity of macrophages

Active Publication Date: 2021-06-29
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-reducing guaiacane-type sesquiterpene lactone compound and preparation method thereof
  • Carbon-reducing guaiacane-type sesquiterpene lactone compound and preparation method thereof
  • Carbon-reducing guaiacane-type sesquiterpene lactone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] a. Take 5 kg of the whole yarrow herb, crush it, use 50 L of ethanol-water solution with a concentration of 50% to extract by cold soaking at room temperature, and evaporate the solvent to dryness under reduced pressure to obtain the crude extract of the whole yarrow plant;

[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 layer and evaporate to dryness under reduced pressure to obtain the ethyl acetate layer extract extract;

[0040] c. The ethyl acetate layer extract extract obtained in step b is separated with a normal phase silica gel column, and gradient elution is carried out with petroleum ether-ethyl acetate with a volume ratio of 50:1-0:1, and the fraction passes through a silica gel thin layer For chromatographic analysis, the same fractions were combined to obtain 9 fractions F1-F9; fraction F4 was separated by Sephadex LH-20 gel colu...

Embodiment 2

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

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

[0044] c. Separate the dichloromethane extract extract obtained in step b with a normal-phase silica gel column, carry out gradient elution with n-hexane-acetone with a volume ratio of 100:1-0:1, and analyze the flow points by silica gel thin-layer chromatography , combined the same fractions to obtain 9 fractions F1-F9; fraction 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 5 kg of the whole plant of Achillea miltiorrhiza, grind it and extract it by percolating with 40 L of absolute ethanol at room temperature, and evaporate the solvent to dryness under reduced pressure to obtain the crude extract of the whole plant of Achillea miltifolia;

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

[0048] c. Separate the ethyl acetate extract extract obtained in step b with a normal-phase silica gel column, carry out gradient elution with cyclohexane-acetone with a volume ratio of 50:1-0:1, and flow through silica gel thin-layer chromatography Analysis, combined the same fractions to obtain 9 fractions F1-F9; fraction F4 was separated by ODS reverse-phase column, eluted with methanol-water solution gradient with a concent...

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Abstract

The present invention relates to a carbon-reduced guaiac-type sesquiterpene lactone compound and a preparation method thereof. The carbon-reduced guaiac-type sesquiterpene lactone compound is obtained from Achillea phyllo ( Achillea millefolium L.) The whole herb is detected and analyzed by thin layer chromatography and analytical high performance liquid chromatography, extracted with organic solvent, and then through solvent extraction, normal phase silica gel column chromatography, small pore resin column chromatography , Sephadex LH-20 gel column chromatography, semi-preparative high-performance liquid chromatography in four to five methods for separation, to obtain three new decarburized guaiacane-type sesquiterpene lactones The three monomer compounds were identified as new decarburized guaiac-type sesquiterpene lactone compounds by high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy, and their structures were identified. The anti-inflammatory activity was measured, and the results showed that: the three new decarburized guaiac-type sesquiterpene lactone compounds all have different degrees of anti-inflammatory activity and can be used to prepare anti-inflammatory drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a carbon-reduced guaiac-type sesquiterpene lactone compound and a preparation method thereof. Background technique [0002] Terpenoids are an important part of natural organic compounds, which are formed by connecting several isopentenes end to end, of which three isopentenes are sesquiterpenes. Sesquiterpene lactones are lactone compounds whose basic skeleton is composed of three isopentenyl units. Guaiac-type sesquiterpene lactones are a very important class of sesquiterpenes that exist in nature. Inflammatory, antibacterial, antitumor, etc. At present, there are hundreds of guaiacane-type sesquiterpenes that have been isolated and identified in nature. The reason for their rich structure is that their skeletons often have various substituents, such as hydroxyl, acetyloxy, propionyloxy , Isobutyryloxy, etc. The positions, numbers and configurations of these substituents on...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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
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