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Methods for sulphation modification of 20(S)- ginsenoside Rh2, and separation and identification of sodium sulfovinate produced thereby

A technology of ginsenoside and sodium sulfate, which is applied in the fields of material separation, material analysis, organic chemistry, etc., can solve the problems that are difficult to modify and have not yet seen the sulfation modification method of saponins

Inactive Publication Date: 2009-05-27
韦旭斌 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to find more active drugs from ginsenosides and modify their molecular structure, aglycones are relatively stable cycloalkane structures, which are difficult to modify, but it is easier and possible to chemically modify their sugars or sugar chains
Saponins and Rh 2 The report of the sulfation modification method

Method used

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  • Methods for sulphation modification of 20(S)- ginsenoside Rh2, and separation and identification of sodium sulfovinate produced thereby
  • Methods for sulphation modification of 20(S)- ginsenoside Rh2, and separation and identification of sodium sulfovinate produced thereby
  • Methods for sulphation modification of 20(S)- ginsenoside Rh2, and separation and identification of sodium sulfovinate produced thereby

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 2 mL of pre-cooled anhydrous pyridine into a flask equipped with a stirring device and a condensing device, place the flask in an ice-salt water bath, stir vigorously, and then add 84 μL of chlorosulfonic acid dropwise, and a pale yellow color appears Solid, end of preparation of esterifying agent. Accurately weigh 20(S)-ginsenoside Rh 2 200mg, dissolved in 2mL of anhydrous pyridine. Pour into the flask with the esterification reagent, place it at room temperature and stir continuously, and react for 3 hours.

[0040] The reactant was neutralized to pH 7.0 with 1mol / L NaOH in an ice bath. A white precipitate was precipitated, filtered under reduced pressure, and the filtrate was dried to obtain 310 mg. With the expansion system (CHCl 3 —AcOEt—MeOH—H 2 O (15:40:22:10) to take the water phase) for TLC analysis, divided into I, II, III substances. Mix the sample with 2 times of silica gel, separate by silica gel column chromatography (silica gel 100-200 mesh, 1.5...

Embodiment 2

[0044] Add 2 mL of pre-cooled anhydrous pyridine into a flask equipped with a stirring device and a condensing device, place the flask in an ice-salt water bath, stir vigorously, and then add 21 μL of chlorosulfonic acid dropwise, and a pale yellow color appears Solid, end of preparation of esterifying agent. Accurately weigh 20(S)-ginsenoside Rh 2 100mg, dissolved in 2mL of anhydrous pyridine. Pour it into the flask with the esterification reagent, place it at room temperature and stir continuously, react for 3 hours, then heat to 30 and 40°C, and react for 3 hours each.

[0045] The reactant was neutralized to pH 7.5 with 1mol / L NaOH in an ice bath. A white precipitate was precipitated, filtered under reduced pressure, and the filtrate was dried to obtain 150 mg. With the expansion system (CHCl 3 —AcOEt—MeOH—H 2 O (15:40:22:10) to take the water phase) for TLC analysis, divided into I, II, III substances. Mix the sample with 2 times of silica gel, separate by silica ge...

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Abstract

The invention relates to a method for chemical modifying of ginsenoside and separating identification of a ginsenoside derivative, in particular to a method for sulfation modifying of 20(S)-ginsenoside Rh2 and a method for separating identification of 20(S)-ginsenoside Rh2 sodium sulfovinate generated from 20(S)-ginsenoside Rh2. The invention is characterized in that the prepared chlorosulfonic acid-pyridine esterifying agent is reacted with 20(S)-ginsenoside Rh2; and by the column chromatography separation technique, two target compounds of the 20(S)-ginsenoside Rh2 sodium sulfovinate are obtained. The spectroscopy proves that except keeping infrared spectrum characteristic peak, the number of sulfuric ester bonds of the target compositions is increased, the molecular weights are both 724, H of -OH of a Rh2 molecular replaces a -SO3Na group, and the two target compounds are a pair of isomers. The aim of the invention is to provide a sulfation modifying method for reconstructing molecular structure of the ginsenoside, provide scientific base and new research thought for finding ginsenoside derivatives with stronger biological activity, and provide though for deeply developing ginsenoside compound.

Description

technical field [0001] The method relates to a method for the separation and identification of ginsenoside chemical modification and its derivatives, especially 20(S)-ginsenoside Rh 2 Sulfation modification method and 20(S)-ginsenoside Rh produced therefrom 2 Separation and identification method of sodium sulfate. Background technique [0002] Ginsenosides (Ginsenosides) are one of the main active ingredients of Panax ginseng, American ginseng, Panax notoginseng, etc. Its structure is composed of aglycone and sugar or sugar chains, and it is a dammarane-type tetracyclic triterpenoid compound. It can be seen from its structure-activity relationship that the biological activity of ginsenosides is related to the sugar contained in it (Dou Deqiang, Jin Ling, Chen Yingjie. Research progress and prospect of chemical components and pharmacological activities of ginseng. Journal of Shenyang Pharmaceutical University, 1999, 16(2):151~156), such as Rh 2 than Rg 3 One less sugar, a...

Claims

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Application Information

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IPC IPC(8): C07J17/00G01N30/00G01N21/35G01N24/08G01N21/3563
Inventor 韦旭斌王鲁付本懂申海清许小琴褚秀玲
Owner 韦旭斌
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