Pseuoginsenoside-Rh 2 and application to preparation of tumor treating medicine

A technology for simulating ginsenosides and antitumor drugs, applied in the field of traditional Chinese medicine, can solve problems such as different side chain structures, and achieve the effect of obvious curative effect

Inactive Publication Date: 2012-03-28
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0025] The task of the present invention is to use protopanaxadiol type saponins or protopanaxadiol group saponins to convert new compounds, which are similar in structure to ginsenoside Rh2, and are also tetracyclic triterpene compounds. The 3-position is also connected to a glucose, only the side chain The structure is different, and the relevant documents have not been reported after searching

Method used

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  • Pseuoginsenoside-Rh 2 and application to preparation of tumor treating medicine
  • Pseuoginsenoside-Rh 2 and application to preparation of tumor treating medicine
  • Pseuoginsenoside-Rh 2 and application to preparation of tumor treating medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Preparation and Structure Identification of Pseudoginsenoside-Rh2

[0069] Preparation

[0070] Take 60g of American ginseng stem and leaf diol group saponins and dissolve them in 800mL of 95% ethanol, and then add 800mL of 4% sulfuric acid aqueous solution. After mixing evenly, heat to 90°C and reflux for 5h to terminate the reaction. Adjust pH=6~8 with NaOH. The solvent was recovered, filtered, and the precipitate was dissolved in 95% ethanol, filtered, and evaporated to dryness to obtain 24 g of the converted product.

[0071] Take 24 g of the total conversion product, and use column chromatography silica gel dry packing. With eluent CHCl 3 -MeOH-EtOAc-H 2 O (2:2:4:1, lower layer) was eluted, and the received effluent was detected by thin-layer chromatography, and the corresponding effluents were combined, concentrated to dryness, and then silica gel column chromatography was performed, and CHCl 3 -MeOH-EtOAc-H 2 O (1.5:2:4:1, lower layer) was eluted, and th...

Embodiment 2

[0094] Dissolve 10g of ginsenoside Rb1 in 100mL of methanol, and then add 100mL of 5% aqueous hydrochloric acid. After mixing evenly, heat to 80°C and reflux for 6h to terminate the reaction. Adjust pH=6~8 with NaOH. The solvent was recovered, filtered, and the precipitate was dissolved in 95% ethanol, filtered, and evaporated to dryness to obtain 3.8 g of the converted product.

[0095] Take 3.8 g of the above-mentioned conversion product and pack it into a column with silica gel for column chromatography. With eluent CHCl 3 -MeOH-EtOAc-H 2 O (2:2:4:1, the lower layer) elutes, and the received effluent is detected by thin-layer chromatography, combined with the corresponding effluent, concentrated to dryness, and then silica gel column chromatography, and CHCl 3 -MeOH-EtOAc-H 2 O (1.5:2:4:1, lower layer) was eluted, and the received effluent was detected by thin-layer chromatography, and the corresponding effluents were combined and concentrated to dryness. Component I ...

Embodiment 3

[0097] Take 20g of panaxadiol group saponins and dissolve in 300mL of dioxane, then add 300mL of 5% sulfuric acid aqueous solution. After mixing evenly, heat to 100°C and reflux for 4h to terminate the reaction. Adjust pH=6~8 with NaOH. The solvent was recovered, filtered, and the precipitate was dissolved in 95% ethanol, filtered, and evaporated to dryness to obtain 7.9 g of the converted product.

[0098] Take 7.9 g of the total conversion product, and use column chromatography silica gel dry packing. With eluent CHCl 3 -MeOH-EtOAc-H 2 O (1.5:2.2:4:1, lower layer) was eluted, and the received effluent was detected by thin-layer chromatography, and the corresponding effluents were combined, concentrated to dryness, and then carried out by silica gel column chromatography, and analyzed with CHCl 3 -MeOH-EtOAc-H 2 O (1.5:2:4:1, lower layer) was eluted, and the received effluent was detected by thin-layer chromatography, and the corresponding effluents were combined and con...

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PUM

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Abstract

The invention discloses a new compound pseuoginsenoside-Rh2, a preparation method of the compound and an application of the compound to preparation of a tumor treating medicine. Both the compound and the ginsenoside-Rh2 are tetracyclic triterpenoid compounds; beta-D-glucopyranose is boned at the positions 3 of the compound and the ginsenoside-Rh2 respectively; the structures of the lateral chains are different; and both the compound and the ginsenoside-Rh2 have degradation products of panoxadiol saponin and have an anticancer effect.

Description

technical field [0001] The invention discloses a new compound pseudo-ginsenoside-Rh2, and provides a preparation method of the compound; meanwhile, it also discloses the use of the compound in preparing antitumor drugs, belonging to the technical field of traditional Chinese medicine. Background technique [0002] Research on ginsenosides began in the early 1960s. Ginsenoside Ra has been isolated from the roots, stems, leaves, flowers, and fruits of Araliaceae plants such as ginseng, American ginseng, and Panax notoginseng. 1 、Ra 2 、Ra 3 , Rb 1 , Rb 2 , Rb 3 , Rc, Rd, Re, Rg 1 , Rg 2 , Rg 3 , Rf , F 1 , F 2 , Rh 1 、Rh 2 More than 50 kinds of tetracyclic triterpenoid ginsenosides. According to the different saponins of compounds, they are divided into several categories, among which Ra 1 、Ra 2 , Ra, Rb 1 , Rb 2 , Rb 3 , Rc, Rd, Rg 3 、Rh 2 Their saponins are 20(S)-protopanaxadiol, so they belong to protopanaxadiol type saponins; and Re, Rg 1 , Rg 2 , Rf, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00A61P35/00A61P35/02
Inventor 睢大筼陈燕萍于晓风王志才曲绍春马兴元曲相如
Owner JILIN UNIV
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