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Pseudoginsenoside Pdq and its semi-synthesis process and medicine use

A ginsenoside, semi-synthetic technology, applied in the direction of steroids, organic chemistry, etc., to achieve significant curative effect

Active Publication Date: 2005-12-14
李平亚
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no report on the synthesis method and compound of pseudo-ginsenoside-Pdq. This compound is a new compound and is the first synthesis; the new drug use of this compound is the first discovery

Method used

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  • Pseudoginsenoside Pdq and its semi-synthesis process and medicine use
  • Pseudoginsenoside Pdq and its semi-synthesis process and medicine use
  • Pseudoginsenoside Pdq and its semi-synthesis process and medicine use

Examples

Experimental program
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Effect test

Embodiment 1

[0075] a. Semi-synthetic method, take 1.0g 20(S)-protopanaxadiol saponin, dissolve it in 50ml 1,4-dioxane, and add H 2 SO 4 Adjust the pH value to 3, add 5 ml of m-chloroperbenzoic acid dropwise with stirring, heat to reflux at 75°C for 90 minutes, after cooling, adjust the pH to 7.0 with 0.1M NaOH aqueous solution, filter, and concentrate the filtrate to dryness to obtain crude Ginsenoside-Pdq 0.9g;

[0076] b. Purification of pseudo-ginsenoside-Pdq, the crude pseudo-ginsenoside-Pdq obtained in the previous step is subjected to silica gel column chromatography to obtain pure pseudo-ginsenoside-Pdq: 0.7g.

Embodiment 2

[0078] a. Semi-synthetic method, take 1.0g 20(S)-protopanaxadiol saponin and dissolve it in 50ml CHCl 3 Medium, enriched H 2 SO 4 Adjust the pH value to 4, add 5ml of p-chloroperbenzoic acid dropwise with stirring, heat to reflux at 80°C for 90 minutes, after cooling, adjust the pH to 7.0 with 0.1M NaOH aqueous solution, filter, and concentrate the filtrate to dryness to obtain crude Ginsenoside-Pdq 0.8g.

[0079] b. Purification of pseudo-ginsenoside-Pdq: the crude pseudo-ginsenoside Pdq obtained in the previous step is dissolved in water, extracted with n-butanol, and purified to obtain pure pseudo-ginsenoside-Pdq: 0.6g.

Embodiment 3

[0081] a. Semi-synthetic method, take 1.0g 20(S)-protopanaxadiol saponin, dissolve it in 50ml 1,4-dioxane, and add H 2 SO 4 Adjust the pH value to 5, add H dropwise under stirring 2 O 2 5ml, heated to reflux at 85°C for 90 minutes, after cooling, adjust the pH to 7.0 with 0.1M NaOH aqueous solution, filter, and concentrate the filtrate to dryness to obtain 0.7g of crude pseudo-ginsenoside-Pdq;

[0082] b. Purification of pseudo-ginsenoside-Pdq, the crude pseudo-ginsenoside-Pdq obtained in the previous step is subjected to silica gel column chromatography to obtain pure pseudo-ginsenoside-Pdq: 0.5g.

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Abstract

The present invention relates to pseudoginseenoside-Pdq and its semi-synthesis process and medicinal use, and belongs to the field of new compound and its synthesis and medicinal use. The material 20(S)-protopanoxadiol saponin or 20(R)-protopanoxadiol saponin is processed through oxidation, cyclization and other steps under acid condition to produce pseudoginseenoside-Pdq as one new compound, named chemically as damar-20S, 20R-epoxy-3beta, 12beta, 25-triol. Pseudoginseenoside-Pdq has wide application in preparing medicine for treating coronary heart disease, myocardial ischemia, ischemic shock, arrhythmia, etc.

Description

Technical field [0001] The invention relates to pseudo-ginsenoside-Pdq and a semi-synthetic method thereof, and its application in preparing medicines for treating myocardial ischemia, ischemic shock, arrhythmia and reperfusion injury. Background technique [0002] Since ginsenosides were confirmed as the main active ingredients in ginseng and American ginseng, chemists have devoted themselves to the synthesis of certain monomeric saponins and the conversion of effective monomers. At present, there are mainly the following methods in research and application, such as acid hydrolysis, alkaline hydrolysis, enzymatic hydrolysis, condensation, etc. The first three methods are mainly between total glycosides and monomer saponins, by hydrolyzing a certain part or several parts of the molecule to realize the conversion of a certain monomer saponins or children's monomer saponins; the latter is through sugar and The aglycon can obtain a certain monomer compound through the glycoside reac...

Claims

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Application Information

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IPC IPC(8): C07J17/00
Inventor 李平亚刘金平
Owner 李平亚
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