Dammarane type triterpenoid saponin compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs

A technology of triterpene saponins and dammarane, which is applied in the preparation of sugar derivatives, chemical instruments and methods, anti-inflammatory agents, etc., and can solve problems such as adverse reactions

Active Publication Date: 2020-02-04
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these two types of anti-inflammatory drugs have good clinical anti-inflammatory effects, long-term large-scale use will produce a series of adverse reactions and tolerance, such as gastric mucosal damage, liver damage, kidney damage, etc.

Method used

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  • Dammarane type triterpenoid saponin compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs
  • Dammarane type triterpenoid saponin compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs
  • Dammarane type triterpenoid saponin compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The method for preparing the dammarane type triterpene saponins compound of structure (1-11) as shown in formula (I), comprises the steps:

[0064] 1-1) Heat and extract Cyclocarya paliurus leaves with 12 times the amount of 50% ethanol for 3 times, each time for 2 hours, filter, concentrate the filtrate, recover ethanol to obtain a crude extract;

[0065] 1-2) Take the crude extract obtained in step 1-1) and mix the sample with 80-100 mesh silica gel at a mass ratio of 1:1.4, separate by silica gel column chromatography, and use a dichloromethane-methanol mixed solution for gradient Elution, the volume ratio of dichloromethane-methanol is (100:0-0:100), the eluted fractions are analyzed and combined by thin-layer chromatography, and the volume ratio of dichloromethane-methanol is collected as (10-5) : 1 elution position, the crude product after silica gel column chromatography separation;

[0066] 1-3) the crude product obtained in step 1-2) after separation by silica...

Embodiment 2

[0071] The method for preparing the dammarane type triterpene saponins compound of structure (1-11) as shown in formula (I), comprises the steps:

[0072] 2-1) Heat and extract Cyclocarya paliurus leaves with 12 times the amount of 50% ethanol for 3 times, each time for 2 hours, filter, concentrate the filtrate, recover the ethanol to obtain the extract, suspend the crude extract in water, and first use petroleum Ether extraction, extraction with ethyl acetate, recovery of the solvent, to obtain the extract;

[0073]2-2) Take the crude extract obtained in step 2-1) and mix the sample with 80-100 mesh silica gel at a mass ratio of 1:1.3, separate by silica gel column chromatography, and use a dichloromethane-methanol mixed solution for gradient Elution; the dichloromethane-methanol volume ratio is (100:0-0:100), and the eluted fractions are combined with thin-layer chromatography analysis, and the dichloromethane-methanol volume ratio is collected as (10-5) : 1 elution positio...

Embodiment 3

[0078] The method for preparing the dammarane type triterpene saponins compound of structure (1-11) as shown in formula (I), comprises the steps:

[0079] 3-1) Heat and extract Cyclocarya paliurus leaves with 13 times the amount of 75% ethanol for 3 times, each time for 3 hours, filter, concentrate the filtrate, recover the ethanol to obtain the extract;

[0080] 3-2) Take the crude extract obtained in step 3-1) and mix the sample with 80-100 mesh silica gel at a mass ratio of 1:1.3, separate by silica gel column chromatography, and use a dichloromethane-methanol mixed solution for gradient Elution; the dichloromethane-methanol volume ratio is (100:0-0:100), and the eluted fractions are combined with thin-layer chromatography analysis, and the dichloromethane-methanol volume ratio is collected as (10-5) : 1 elution position, the crude product after silica gel column chromatography separation;

[0081] 3-3) the crude product obtained in step 3-2) after separation by silica gel...

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Abstract

The invention discloses a dammarane type triterpenoid saponin compound, a preparation method thereof and application thereof in preparation of anti-inflammatory drugs. The dammarane type triterpenoidsaponin compound is obtained by separation of cyclocarya paliurus leaves. The preparation method comprises steps of S1, extracting the cyclocarya paliurus leaves by using an alcohol solvent to obtainan extract, wherein the mass ratio of the cyclocarya paliurus leaves to the alcohol solvent is 1: (10-15); S2, separating the extract prepared in the step S1) sequentially by using silica gel column chromatography, MCI gel column choromatography, reversed-phase column choromatography, gel column choromatography and preparation type high performance liquid chromatography to obtain the compound. Thenew compound prepared by the method can suppress release of NO, TNF-alpha, PGE2 and IL-6 in LPS induced RAW264.7 cells, can reduce expression of iNOS, COX-2 and NF-KB / P65 protein, can take on good anti-inflammatory activity and can be used for developing related anti-inflammatory drugs.

Description

technical field [0001] The invention relates to chemical synthesis, in particular to extracting and separating dammarane-type triterpene saponins from leaves of Cyclocarya paliurus and its preparation method and application. Background technique [0002] Cyclocarya paliurus (Batal) Iljinsk (Juglandaceae) is a plant of the Juglandaceae Cyclocarya paliurus (Batal) Iljinsk (Juglandaceae) plant. Guangxi, Guizhou, Hunan, Hubei, Sichuan, Fujian, Jiangxi, Zhejiang, Anhui and other places have a long history of medication and are commonly used Chinese herbal medicines in my country. [0003] The main chemical constituents of Cyclocarya paliurus are triterpenoids, mainly including dammarane triterpenoid saponins, flavonoids, phenolic acids and so on. Modern pharmacological studies have shown that the crude extract of Cyclocarya paliurus has the functions of lowering blood sugar, blood pressure, blood fat, anti-inflammation, anti-tumor, anti-oxidation, and antibacterial. [0004] Mac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/256C07H1/08A61P29/00A61K31/704
CPCC07H15/256C07H1/08A61P29/00C07C2603/16Y02A50/30
Inventor 李俊刘威黄锡山邓胜平李陈国黄艳张艳军
Owner GUANGXI NORMAL UNIV
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