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Method for preparing 20(R)-25-hydroxy-dammarane type-3beta,12beta,20-triols

A technology of dammarane type and hydroxyl group, which is applied in the field of preparation of 20(R)-25-hydroxy-dammarane type-3β,12β,20-triol, and can solve problems such as difficulty in obtaining a large amount of

Active Publication Date: 2012-11-14
辽宁新中现代医药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the difficulty in obtaining a large amount of C-K and protopanaxadiol, the preclinical evaluation of these two compounds has not been systematically reported.

Method used

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  • Method for preparing 20(R)-25-hydroxy-dammarane type-3beta,12beta,20-triols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Preparation of 20(R)-25-OH-PPD by silica gel chromatography

[0019] 5kg dried Araliaceae ginseng fresh ginseng fruit was extracted with 70% ethanol, passed through a D101 macroporous adsorption resin column (provided by Tianjin Chemical Co., Ltd.), washed with water and eluted from the column with 70% ethanol to separate and purify it , After drying, the total saponins of ginseng fruit are obtained. Take 10 g of total saponins from ginseng fruit, extract with chloroform, and separate the chloroform extract by silica gel column chromatography. 7 fractions are obtained by gradient elution of chloroform: methanol (30: 1-5: 1), and fraction 5 is passed through a reverse-phase silica gel column layer. 20(R)-25-OH-PPD was obtained after separation by precipitation, elution with acetonitrile: water (80:20), and recrystallization from ethyl acetate in a yield of 0.18%.

Embodiment 2

[0020] Example 2: 20(R)-25-OH-PPD was prepared by alkaline hydrolysis

[0021] 10 g of total ginsenosides were weighed, dissolved in 1000 ml of 95% ethanol solution, filtered to remove insoluble matter to obtain a filtrate. The prepared 0.5% (W / V) sodium hydroxide ethanol solution was added to the above-mentioned filtrate under stirring, kept at rest, filtered, washed with water and precipitated to neutrality. The dried precipitate was separated by silica gel column chromatography, and 8 fractions were obtained by gradient elution of petroleum:ethyl acetate (30:1-1:1). Fraction 5 was recrystallized from ethyl acetate to give 20(R) -25-OH-PPD white crystal, yield 1.2%.

Embodiment 3

[0022] Example 3: Preparation of 20(R)-25-OH-PPD by Sodium Hydroxide Hydrolysis

[0023] Weigh 10 g of total saponins from ginseng fruit, dissolve it in 1000 ml of methanol aqueous solution with a sodium hydroxide concentration of 2.5 mol / L and a concentration of 80% for 24 h, neutralize the reaction solution with 2.5 mol / L hydrochloric acid, recover methanol under reduced pressure, and extract with chloroform The reaction solution, the chloroform phase was washed with water, dried over anhydrous sodium sulfate, evaporated to dryness to collect the residue, separated by silica gel column chromatography, and eluted with a petroleum:ethyl acetate (50:1-2:1) gradient to obtain 8 fractions, Fraction 5 was recrystallized from ethyl acetate to obtain 20(R)-25-OH-PPD white crystals in a yield of 1.4%.

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Abstract

The invention provides a method for preparing protopanoxadiol derivatives of a formula below, namely 20(R)-25-hydroxy-dammarane type-3beta,12beta,20-triols[abbreviated as 20(R)-25-OH-PPD]. The protopanoxadiol derivatives are obtained by hydrolyzing total ginsenoside, wherein the method for hydrolyzing the total ginsenoside comprises a basic hydrolysis process, an acid hydrolysis process I and an acid hydrolysis process II. The structure of the 20(R)-25-hydroxy-dammarane type-3beta,12beta,20-triols is determined by nuclear magnetic resonance spectrum. The method is high in yield and purity, ensures stable product quality and can realize industrial production and can meet the needs for development of new antitumor medicines.

Description

[0001] The application number is 200610047404.1 filed by Liaoning Xinzhong Modern Medicine Co., Ltd. on August 7, 2006, and the name of the invention is "20(R)-25-hydroxy-dammarane type-3β, 12β, 20-triol Preparation method" divisional application. technical field [0002] The invention relates to a preparation method of a protopanaxadiol derivative 20(R)-25-hydroxy-dammarane type-3β, 12β, 20-triol [referred to as 20(R)-25-OH-PPD] of structural formula . The preparation method includes A: silica gel chromatography; B: alkaline hydrolysis method, after acid neutralization, organic solvent extraction and silica gel column chromatography separation, 20(R)-25-OH-PPD white crystals are obtained; C, acid hydrolysis Method I, 20(R)-25-OH-PPD is obtained after alkali neutralization, organic solvent extraction and separation by silica gel column chromatography; D, acid hydrolysis method II, precipitation by adding water, washing with water until the neutral precipitation passes through...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
Inventor 赵余庆关健孙宝山
Owner 辽宁新中现代医药有限公司
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