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Process for preparing 20(R)-ginsenoside Rh2

A technology of ginsenosides and total saponins, which is applied in the directions of medical preparations, pharmaceutical formulations, and pills containing active ingredients, can solve problems such as unfavorable industrial production, increased steps for separation and purification of saponins, and increased reaction product components.

Active Publication Date: 2004-12-29
云南白药集团天然药物研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] It should be emphasized that the above method is not conducive to 20(R)-ginsenoside Rh 2 The industrialized production of this group, its major defect is at first must obtain protopanaxadiol group saponin, has increased the step of the separation and purification of this group saponin, has gone through the preparation of 20(R&S)-ginsenoside Rg3 in the conversion preparation, acetylation, catalytic hydrolysis Such complicated reaction steps lead to an increase in the reaction product components, and the resulting product is 20(R&S)-ginsenoside Rh 2 , it is difficult to obtain pure 20(R)-ginsenoside Rh 2 and increase productivity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Prepare 100 ml of 60% acetic acid aqueous solution, add 20 grams of ginsengdiol group saponin dry powder, under 0.1 MPa pressure, stir and heat, and carry out hydrolysis reaction at 100°C for 2 hours. After the reaction is completed, wash the reaction mixture with water until it reaches the middle. After filtration, the filtrate was dried at 100°C to obtain 12 grams of hydrolysate. Purified by silica gel column chromatography, the eluent was chloroform:methanol:ethyl acetate:water=2:2:4:1 (volume ratio), and the eluate was collected and recrystallized in methanol-water to obtain 20 ( R)-Ginsenoside Rh 2 The white crystals of 983 mg, the yield is 4.92%. The crystal purity was determined to be 97.6% by HPLC method. After TLC, MS, 13 C-NMR, 1 H-NMR, 13 C- 1 HCOSY, 1 H- 1 HCOSY, specific rotation and melting point determination, and with 20(R)-ginsenoside Rh 2 Verification of the literature data confirms that the white crystal is 20(R)-ginsenoside Rh 2 .

Embodiment 2

[0016] Add 60ml of glacial acetic acid to 40ml of 95% ethanol, add 20g of ginsengdiol group saponins dry powder, stir and heat under a pressure of 0.1 MPa, and carry out the hydrolysis reaction at 75°C for 1.5 hours. After the reaction is complete, keep it hot Pour into 400 ml of water at 25°C to dilute, and recover ethanol under reduced pressure. The reactant was continuously washed with water to neutrality, filtered, and the filtrate was dried at 80° C. to obtain 13.6 g of hydrolysate. Purified by silica gel column chromatography, the eluent was chloroform:methanol:ethyl acetate:water=2:2:4:1 (volume ratio), and the eluate was collected and recrystallized in methanol-water to obtain 20 ( R)-Ginsenoside Rh 2 1082 mg of white crystals, yield 7.95%. Its purity was determined to be 95.3% by HPLC method. After TLC, MS, 13 C-NMR, 1 H-NMR, 13 C- 1 H COSY, 1 H- 1 HCOSY, specific rotation and melting point determination, and with 20(R)-ginsenoside Rh 2 Verification of the literature data...

Embodiment 3

[0018] Dissolve 10 ml of 36% hydrochloric acid in water to make 100 ml, add 20 g of ginsengdiol group saponins dry powder, stir and heat under a pressure of 0.1 MPa, and carry out the hydrolysis reaction at 100°C for 1.5 hours. After the reaction is complete, The reaction mixture was washed with water to neutrality, filtered, and the filtrate was dried at 100°C to obtain 11.4 g of the hydrolyzate. Purified by silica gel column chromatography, the eluent was chloroform:methanol:ethyl acetate:water=2:2:4:1 (volume ratio), and the eluate was collected and recrystallized in methanol-water to obtain 20 ( R)-Ginsenoside Rh 2 869 mg of white crystals, yield 4.35%. Its purity was determined to be 96.2% by HPLC method. After TLC, MS, 13 C-NMR, 1 H-NMR, 13 C- 1 HCOSY, 1 H- 1 HCOSY. Specific rotation and melting point determination, and 20(R)-ginsenoside Rh 2 Verification of the literature data confirms that the white crystal is 20(R)-ginsenoside Rh 2 .

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PUM

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Abstract

The present invention is the preparation process of 20(R)-ginsenoside Rh2 with panax leaf and stem total saponin or protopanoxadiol saponin as initial material. The preparation process includes dissolving the material in the water solution or alcohol solution of organic acid or inorganic acid for acid hydrolysis and collecting the reaction product. The product may be silica gel chromatographic column separated and re-crystallized to purify. The acid hydrolysis is completed at 30-100 deg.c and 0.05-1 MPa, and the organic acid and the inorganic acid include formic acid, acetic acid, hydrochloric acid, sulfuric acid and nitric acid. In addition, the prepare process of medicine composition with 20(R)-ginsenoside Rh2 is also disclosed. The present invention has reasonable technological process and high yield.

Description

Technical field [0001] The present invention relates to 20(R)-ginsenoside Rh 2 The preparation method. Background technique [0002] Cancer is a disease that seriously endangers human health. According to statistics from the World Health Organization (WHO), there are approximately 10 million cancers worldwide and approximately 7 million deaths each year. It has become the second killer of humans after cardiovascular diseases. At present, most of the anti-cancer drugs in clinical use have relatively large side effects. Therefore, it is very urgent to develop new drugs for the treatment of cancer. In particular, finding safe and efficient anti-cancer active ingredients from traditional Chinese botanicals has always been a hot spot for drug researchers. [0003] In the 1980s, a large number of research reports showed that ginsenosides have certain anti-tumor activities, especially the Japanese scholar Kitagawa Ho (Pharmaceutical Journal [Japanese] 1983.103; 612) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/08A61K9/20A61K9/48A61K31/704A61P35/00C07J9/00C07J63/00
CPCY02P20/582
Inventor 高崇昆杨晓源董汛唐文旭
Owner 云南白药集团天然药物研究院
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