Semi-synthetic method of pseudo-ginsenoside F11

A technology for simulating ginsenosides and ginsenosides, applied in the directions of steroids, organic chemistry, etc., can solve the problems such as no reports on the semi-synthetic method of ginsenoside F11, and achieve the effects of significant curative effect, improvement of mood, and ease of reaction conditions.

Active Publication Date: 2009-09-02
李平亚
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There is no report on the semi-synthetic method of pseudo-ginsenoside F11

Method used

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  • Semi-synthetic method of pseudo-ginsenoside F11

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] a. Add 5.0g ginsenoside Rg2 to 50ml 1,4-dioxane, add concentrated H 2 SO 4 Adjust the pH value to 3-5, add 20ml of p-chloroperbenzoic acid dropwise under stirring, heat and reflux at 85°C for 20 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 pseudo-ginsenoside-F11: 3.0g;

[0015] b. Purification of pseudo-ginsenoside F11: take crude pseudo-ginsenoside F11 and carry out silica gel column chromatography, the eluent is n-butanol: ethyl acetate: water = 65:35:10, and n-butanol solvent extraction method can also be used Purification was carried out to obtain pure pseudoginsenoside-F11: 2.5g.

[0016] Ginsenoside Rg2 can be obtained by conventional methods in the prior art, for example:

[0017] Take 5.0g ginsenoside Re, add 22g NaOH, dissolve in 50ml 1,2-propanediol, heat to reflux for 5h, and cool at room temperature. After adding 1.5 times of water to dilute, use concentrated...

Embodiment 2

[0019] Get 5.0g ginsenoside Rg2 and add in 50ml cyclohexane, add concentrated H 2 SO 4 Adjust the pH to 5, add m-chloroperbenzoic acid 20ml dropwise under stirring, heat and reflux at 85°C for 30 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 F11: 3.1g.

Embodiment 3

[0021] Take 5.0g ginsenoside Rg2 and add it to 50ml 1,4-dioxane, add concentrated H 2 SO 4 Adjust the pH to 4, add 20ml of peracetic acid dropwise under stirring, heat and reflux at 80°C for 20 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 pseudoginsenoside F11 : 3.7g.

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Abstract

The invention relates to a semi-synthetic method of pseudo-ginsenoside F11. The method adopts ginsenoside Rg2 as raw material and synthesizes the pseudo-ginsenoside F11 compound by the steps of oxidation and cyclization and the like under acid condition; and the chemical name thereof is 6-O-Alpha-L-rhamnopyranosyl(1-2)-Beta-D-glucopyranosyl-dammar-20S, 24S-epoxy-3Beta, 6Alpha, 12Beta, 25-tetrahydric alcohol. The method has convenient source of materials, mild reaction condition, simple and convenient operation, high yield and short production period and is suitable for realizing industrial production.

Description

technical field [0001] The invention relates to a semi-synthetic method for pseudoginsenoside F11. Background technique [0002] Since ginsenosides were confirmed as the main active ingredients in ginseng and American ginseng, chemists and medical scientists have devoted themselves to the synthesis of certain monomeric saponins and the transformation or structural modification of effective monomers to improve their chemical properties and enhance their biological properties. active purpose. At present, there are mainly the following methods in research and application, such as acid hydrolysis, alkali hydrolysis, enzymatic hydrolysis, condensation, oxidative cyclization, etc. [0003] In 1982, Hart B H first reported the degradation of ginsenoside under mild acid conditions and determined the structure of the degradation products. For example, ginsenoside-Rg1 was treated with 0.1M HCl at 37°C with no interval time to obtain the degradation product ginsenoside Rh1. Rg3 (Pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00
Inventor 李平亚刘金平
Owner 李平亚
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