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Fatty acid ester compounds of ginsenoside secondary glycoside compound K and method for preparing same

A technology of stearate and protopanaxadiol, which is applied in the fields of medical preparations containing active ingredients, sugar derivatives, organic chemistry, etc., and can solve problems such as no artificial synthetic products reported in the literature

Active Publication Date: 2007-02-14
JILIN YATAI PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] No literature reports on the above artificially synthesized products were found after searching

Method used

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  • Fatty acid ester compounds of ginsenoside secondary glycoside compound K and method for preparing same
  • Fatty acid ester compounds of ginsenoside secondary glycoside compound K and method for preparing same
  • Fatty acid ester compounds of ginsenoside secondary glycoside compound K and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] Take M130g and dissolve in 1000ml ethyl acetate, add 1000ml water-saturated sodium bicarbonate under stirring condition, add oleic acid chloride or stearic acid chloride 720g under ice-water bath condition, stir overnight at room temperature. Then use a separatory funnel to separate the ethyl acetate layer from the water layer, and repeatedly extract the water layer with ethyl acetate, combine the ethyl acetate, centrifuge (3000rpm), and wash the supernatant with water repeatedly, and the ethyl acetate is at low temperature (20 -30°C) for recovery under reduced pressure, the residue was dissolved in methanol, filtered, and the methanol solution was concentrated under reduced pressure to obtain dry matter.

Embodiment 2

[0126] Take M140g and dissolve in 1200ml ethyl acetate, add 1000ml water-saturated sodium bicarbonate under stirring condition, add oleic acid chloride or stearic acid chloride 700g under ice-water bath condition, stir overnight at room temperature. Then use a separatory funnel to separate the ethyl acetate layer from the water layer, and repeatedly extract the water layer with ethyl acetate, combine the ethyl acetate, centrifuge (3000rpm), wash the supernatant with water repeatedly, and store the ethyl acetate at a low temperature of 20°C ) under reduced pressure recovery, the residue was dissolved in methanol, filtered, and the methanol solution was concentrated under reduced pressure to obtain dry matter.

Embodiment 3

[0128] Take M150g and dissolve in 1500ml ethyl acetate, add 1500ml water-saturated sodium bicarbonate under stirring condition, add oleic acid chloride or stearic acid chloride 720g under ice-water bath condition, stir overnight at room temperature. Then use a separatory funnel to separate the ethyl acetate layer from the water layer, and repeatedly extract the water layer with ethyl acetate, combine the ethyl acetate, centrifuge (3000rpm), and wash the supernatant with water repeatedly. Recover under reduced pressure, dissolve the residue with methanol, filter, and concentrate the methanol solution under reduced pressure to obtain dry matter.

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PUM

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Abstract

The invention discloses a fatty acid ester compounds of ginsenoside secondary glycoside compound K and method for preparing same, wherein the compound includes two derivatized compounds OM1 and SM1 having the structural formula disclosed in the specification, wherein R is oleoyl or stearoyl, and they are all esters formed by compound K with aliphatic acid. The invention also provides the method for synthesizing compound K and aliphatic acid, the pharmaceutical composition using the compositions as active composition, and the use of the compounds and pharmaceutical composition in preparing medicament for treating tumor.

Description

Technical field: [0001] The invention relates to a fatty acid ester compound of ginsenoside secondary glycoside compound K, discloses the molecular structure of the compound, a synthesis method and a pharmaceutical composition using the compound as an active ingredient, and belongs to the technical field of semi-synthesis of active ingredients of traditional Chinese medicine. Background technique: [0002] The ginsenoside secondary glycoside compound K (hereinafter referred to as M1) involved in the present invention is a metabolic product of intestinal bacteria of ginsenoside, and M1 has strong anticancer activity. M1 forms fatty acid esters (EM1) with fatty acids in the liver, which takes longer than M1 to accumulate in the liver. Moreover, through the pharmacokinetic study of M1 and EM1, it was found that esterification of M1 fatty acid to form EM1 improved its anti-tumor activity in vivo and reduced cytotoxicity. Therefore, the anticancer activity of ginseng originates ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/20A61K31/7032A61P35/00
Inventor 郑毅男弓晓杰
Owner JILIN YATAI PHARM CO LTD
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