Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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

A dammarane-type, hydroxyl-based technology, applied in the direction of preparation of steroids, methods based on microorganisms, biochemical equipment and methods, etc., can solve problems such as difficulties in obtaining large quantities

Inactive Publication Date: 2008-02-13
辽宁新中现代医药有限公司
View PDF0 Cites 7 Cited by
  • Summary
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 20(R)-25-hydroxy-dammarane type-3beta,12beta,20-triol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 20(R)-25-OH-PPD by silica gel chromatography

[0018] After the fresh ginseng fruit of Araliaceae Panax plant of 5kg drying is extracted with 70% ethanol, after passing through the D101 macroporous adsorption resin column (provided by Tianjin Chemical Co., Ltd.), after washing, use 70% ethanol to elute from the column to separate and purify it and drying to obtain total saponins of ginseng fruit. Take 10 g of total saponins of ginseng fruit, extract with chloroform, carry out silica gel column chromatography to separate the chloroform extract, and obtain 7 fractions by chloroform:methanol (30:1-5:1) gradient elution, and fraction 5 is passed through the reverse phase silica gel column layer After separation, acetonitrile: water (80:20) elution and ethyl acetate recrystallization, 20(R)-25-OH-PPD was obtained with a yield of 0.18%.

Embodiment 2

[0019] Example 2: Preparation of 20(R)-25-OH-PPD by alkaline hydrolysis

[0020] Weigh 10 g of total ginsenosides, dissolve in 1000 ml of 95% ethanol solution, filter, remove insoluble matter, and obtain a filtrate. Add the prepared 0.5% (W / V) sodium hydroxide ethanol solution into the above filtrate under stirring, let it stand still, filter, and wash the precipitate with water until neutral. 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), and fraction 5 was recrystallized from ethyl acetate to obtain 20(R) -25-OH-PPD white crystal, yield 1.2%.

Embodiment 3

[0021] Example 3: Preparation of 20(R)-25-OH-PPD by hydrolysis of sodium hydroxide

[0022] Weigh 10 g of total saponins of ginseng fruit, dissolve in 1000 ml of 2.5 mol / L sodium hydroxide and 80% methanol aqueous solution and hydrolyze for 24 hours, neutralize the reaction solution with 2.5 mol / L hydrochloric acid, recover methanol under reduced pressure, and extract with chloroform The reaction solution and the chloroform phase were washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness to collect the residue, which was separated by silica gel column chromatography and gradient eluted with petroleum: ethyl acetate (50:1-2:1) to obtain 8 fractions. Fraction 5 was recrystallized from ethyl acetate to obtain white crystals of 20(R)-25-OH-PPD with a yield of 1.4%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a preparation method of the original protopanaxadiol derivative with the structure as 20 (R)-25-hydroxy-dammarane-3beta, 12beta, 20- triol [for short 20 (R)-25-OH-PPD]. The silica gel chromatography and the total ginsenoside hydrolysis are used to make the original protopanaxadiol derivative; therein, the ginsenoside hydrolysis includes the alkali water hydrolysis the acid hydrolysis I and the acid hydrolysis II. The NMR spectrum is used to determine the structure. The method is of the high collection rate, the high purity and the stable quality of the products; the invention can realize the industrial production, and can meet the development requirements of the novel anti-tumor drugs.

Description

technical field [0001] The present invention relates to a preparation method of protopanaxadiol derivative 20(R)-25-hydroxyl-dammarane type-3β,12β,20-triol [20(R)-25-OH-PPD for short] . Its preparation method includes A: silica gel chromatography; B: alkali 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 silica gel column chromatography separation; D, acid hydrolysis method II, add water to precipitate, wash with water until the neutral precipitate passes through the silica gel column layer After analysis and separation, white crystals of 20(R)-25-OH-PPD were obtained. Background technique [0002] In 1979, Japanese scholar Odashima and others discovered ginsenoside Rh 2 In vitro, it can inhibit the proliferation of lung cancer cells 3LL (m...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07J9/00C07J75/00C12P33/00C12R1/745
Inventor 孙宝山赵余庆
Owner 辽宁新中现代医药有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products